Add isomeric smiles

MassBank · Jun 5, 2024 · 5f60e25 · 5f60e25
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diff --git a/MSSJ/MSBNK-MSSJ-MSJ00683.txt b/MSSJ/MSBNK-MSSJ-MSJ00683.txt
@@ -13,7 +13,7 @@ CH$NAME: Citric acid-[1-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C6H8O7
 CH$EXACT_MASS: 192.02701
-CH$SMILES: C(C(=O)O)C(CC(=O)O)(C(=O)O)O
+CH$SMILES: C(C(=O)O)C(C[13C](=O)O)(C(=O)O)O
 CH$IUPAC: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/i3+1
 CH$LINK: CHEMSPIDER 8165754
 CH$LINK: INCHIKEY KRKNYBCHXYNGOX-LBPDFUHNSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00684.txt b/MSSJ/MSBNK-MSSJ-MSJ00684.txt
@@ -1,5 +1,5 @@
 ACCESSION: MSBNK-MSSJ-MSJ00684
-RECORD_TITLE: Citric acid-[5-13C]; GC-EI-Q; MS; POSITIVE; 4TMS-derivative
+RECORD_TITLE: Citric acid-[1-13C]; GC-EI-Q; MS; POSITIVE; 4TMS-derivative
 DATE: 2021.08.26
 AUTHORS: Nobuyuki Okahashi and Fumio Matsuda, Osaka University
 LICENSE: CC BY
@@ -9,11 +9,11 @@ COMMENT: The sample analyzed is labeled with 13C at the carbon atom 5. Carbon at
 COMMENT: DERIVATIVE_TYPE 4TMS; DERIVATIVE_FORMULA C18H40O7Si4; DERIVATIVE_MASS 481.18847 (13C-labeled)
 COMMENT: Annotation of fragment ions (PK$ANNOTATION) is based on Fig.2(b) and Table 1, and Supplemental material page 3 of the publication.
 COMMENT: This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 21HP8020 to the Mass Spectrometry Society of Japan.
-CH$NAME: Citric acid-[5-13C]
+CH$NAME: Citric acid-[1-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C6H8O7
 CH$EXACT_MASS: 192.027005
-CH$SMILES: OC(=O)CC(O)(CC(O)=O)C(O)=O
+CH$SMILES: C(C(=O)O)C(C[13C](=O)O)(C(=O)O)O
 CH$IUPAC: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/i3+1
 CH$LINK: CHEMSPIDER 8165754
 CH$LINK: INCHIKEY KRKNYBCHXYNGOX-LBPDFUHNSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00685.txt b/MSSJ/MSBNK-MSSJ-MSJ00685.txt
@@ -13,7 +13,7 @@ CH$NAME: Citric acid-[6-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C6H8O7
 CH$EXACT_MASS: 192.027005
-CH$SMILES: OC(=O)CC(O)(CC(O)=O)C(=O)O
+CH$SMILES: C(C(=O)O)C(CC(=O)O)([13C](=O)O)O
 CH$IUPAC: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/i5+1
 CH$LINK: INCHIKEY KRKNYBCHXYNGOX-HOSYLAQJSA-N
 AC$INSTRUMENT: GCMS-QP2010 Ultra (Shimadzu, Kyoto, Japan)

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00686.txt b/MSSJ/MSBNK-MSSJ-MSJ00686.txt
@@ -13,7 +13,7 @@ CH$NAME: Citric acid-[1,2,3,4,5,6-13C6]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C6H8O7
 CH$EXACT_MASS: 192.027005
-CH$SMILES: OC(=O)CC(O)(CC(O)=O)C(=O)O
+CH$SMILES: [13CH2]([13C](=O)O)[13C]([13CH2][13C](=O)O)([13C](=O)O)O
 CH$IUPAC: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/i1+1,2+1,3+1,4+1,5+1,6+1
 CH$LINK: CAS 287389-42-8
 CH$LINK: CHEMSPIDER 17345064

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00688.txt b/MSSJ/MSBNK-MSSJ-MSJ00688.txt
@@ -13,7 +13,7 @@ CH$NAME: alpha-ketoglutaric acid-[1,2,3,4-13C4]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C5H6O5
 CH$EXACT_MASS: 146.02152
-CH$SMILES: C(CC(=O)O)C(=O)C(=O)O
+CH$SMILES: [13CH2]([13CH2][13C](=O)[13C](=O)O)C(=O)O
 CH$IUPAC: InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/i1+1,2+1,3+1,5+1
 CH$LINK: INCHIKEY KPGXRSRHYNQIFN-SAXDBNRNSA-N
 CH$LINK: PUBCHEM CID:91971603

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00689.txt b/MSSJ/MSBNK-MSSJ-MSJ00689.txt
@@ -13,7 +13,7 @@ CH$NAME: alpha-ketoglutaric acid-[1,2,3,4,5-13C5]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C5H6O5
 CH$EXACT_MASS: 146.02152
-CH$SMILES: C(CC(=O)O)C(=O)C(=O)O
+CH$SMILES: [13CH2]([13CH2][13C](=O)O)[13C](=O)[13C](=O)O
 CH$IUPAC: InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/i1+1,2+1,3+1,4+1,5+1
 CH$LINK: CHEMSPIDER 71078928
 CH$LINK: INCHIKEY KPGXRSRHYNQIFN-CVMUNTFWSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00691.txt b/MSSJ/MSBNK-MSSJ-MSJ00691.txt
@@ -13,7 +13,7 @@ CH$NAME: Succinic acid-[1,2,3,4-13C4]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O4
 CH$EXACT_MASS: 118.02661
-CH$SMILES: OC(=O)CCC(O)=O
+CH$SMILES: [13CH2]([13CH2][13C](=O)O)[13C](=O)O
 CH$IUPAC: InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)/i1+1,2+1,3+1,4+1
 CH$LINK: CAS 201595-67-7
 CH$LINK: CHEMSPIDER 17341241

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00693.txt b/MSSJ/MSBNK-MSSJ-MSJ00693.txt
@@ -12,7 +12,7 @@ CH$NAME: Fumaric acid-[1,2,3,4-13C4]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H4O4
 CH$EXACT_MASS: 116.01096
-CH$SMILES: O=C(O)/C=C/C(=O)O
+CH$SMILES: [13CH](=[13CH]/[13C](=O)O)\[13C](=O)O
 CH$IUPAC: InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+/i1+1,2+1,3+1,4+1
 CH$LINK: CAS 110-17-8
 CH$LINK: CHEMSPIDER 48063181

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00695.txt b/MSSJ/MSBNK-MSSJ-MSJ00695.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[1-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.021523
-CH$SMILES: C(C(C(=O)O)O)C(=O)O
+CH$SMILES: C(C([13C](=O)O)O)C(=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i4+1
 CH$LINK: CAS 180991-05-3
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-AZXPZELESA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00696.txt b/MSSJ/MSBNK-MSSJ-MSJ00696.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[2-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.021523
-CH$SMILES: C(C(C(=O)O)O)C(=O)O
+CH$SMILES: C([13CH](C(=O)O)O)C(=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i2+1
 CH$LINK: CHEMSPIDER 49071373
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-VQEHIDDOSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00697.txt b/MSSJ/MSBNK-MSSJ-MSJ00697.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[3-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.021523
-CH$SMILES: C(C(C(=O)O)O)C(=O)O
+CH$SMILES: [13CH2](C(C(=O)O)O)C(=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i1+1
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-OUBTZVSYSA-N
 CH$LINK: PUBCHEM CID:153695700

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00698.txt b/MSSJ/MSBNK-MSSJ-MSJ00698.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[4-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.021523
-CH$SMILES: C(C(C(=O)O)O)C(=O)O
+CH$SMILES: C(C(C(=O)O)O)[13C](=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i3+1
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-LBPDFUHNSA-N
 AC$INSTRUMENT: GCMS-QP2010 Ultra (Shimadzu, Kyoto, Japan)

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00699.txt b/MSSJ/MSBNK-MSSJ-MSJ00699.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[1,2,3,4-13C4]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.021525
-CH$SMILES: C(C(C(=O)O)O)C(=O)O
+CH$SMILES: [13CH2]([13CH]([13C](=O)O)O)[13C](=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i1+1,2+1,3+1,4+1
 CH$LINK: CHEMSPIDER 48060182
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-JCDJMFQYSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00701.txt b/MSSJ/MSBNK-MSSJ-MSJ00701.txt
@@ -13,7 +13,7 @@ CH$NAME: Citric acid-[1-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C6H8O7
 CH$EXACT_MASS: 192.02700
-CH$SMILES: OC(=O)CC(O)(CC(O)=O)C(=O)O
+CH$SMILES: C(C(=O)O)C(CC(=O)O)([13C](=O)O)O
 CH$IUPAC: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/i5+1
 CH$LINK: CHEMSPIDER 8165754
 CH$LINK: INCHIKEY KRKNYBCHXYNGOX-HOSYLAQJSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00702.txt b/MSSJ/MSBNK-MSSJ-MSJ00702.txt
@@ -1,5 +1,5 @@
 ACCESSION: MSBNK-MSSJ-MSJ00702
-RECORD_TITLE: Citric acid-[5-13C]; GC-EI-Q; MS; POSITIVE; 4TBDMS-derivative
+RECORD_TITLE: Citric acid-[1-13C]; GC-EI-Q; MS; POSITIVE; 4TBDMS-derivative
 DATE: 2021.10.04
 AUTHORS: Nobuyuki Okahashi and Fumio Matsuda, Osaka University
 LICENSE: CC BY
@@ -9,11 +9,11 @@ COMMENT: The sample analyzed is labeled with 13C at the carbon atom 5.
 COMMENT: DERIVATIVE_TYPE 4TBDMS; DERIVATIVE_FORMULA C30H64O7Si4; DERIVATIVE_MASS 649.37627 (13C-labeled)
 COMMENT: Annotation of fragment ions (PK$ANNOTATION) is based on Table 1 and Supplemental material page 8 of the publication.
 COMMENT: This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 21HP8020 to the Mass Spectrometry Society of Japan.
-CH$NAME: Citric acid-[5-13C]
+CH$NAME: Citric acid-[1-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C6H8O7
 CH$EXACT_MASS: 192.02700
-CH$SMILES: OC(=O)CC(O)(CC(O)=O)C(=O)O
+CH$SMILES: C(C(=O)O)C(C[13C](=O)O)(C(=O)O)O
 CH$IUPAC: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/i3+1
 CH$LINK: CHEMSPIDER 8165754
 CH$LINK: INCHIKEY KRKNYBCHXYNGOX-LBPDFUHNSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00703.txt b/MSSJ/MSBNK-MSSJ-MSJ00703.txt
@@ -13,7 +13,7 @@ CH$NAME: Citric acid-[6-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C6H8O7
 CH$EXACT_MASS: 192.02700
-CH$SMILES: OC(=O)CC(O)(CC(O)=O)C(=O)O
+CH$SMILES: C(C(=O)O)C(CC(=O)O)([13C](=O)O)O
 CH$IUPAC: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/i5+1
 CH$LINK: INCHIKEY KRKNYBCHXYNGOX-HOSYLAQJSA-N
 AC$INSTRUMENT: GCMS-QP2010 Ultra (Shimadzu, Kyoto, Japan)

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00704.txt b/MSSJ/MSBNK-MSSJ-MSJ00704.txt
@@ -13,7 +13,7 @@ CH$NAME: Citric acid-[1,5-13C2]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C6H8O7
 CH$EXACT_MASS: 192.02700
-CH$SMILES: OC(=O)CC(O)(CC(O)=O)C(=O)O
+CH$SMILES: C([13C](=O)O)C(C[13C](=O)O)(C(=O)O)O
 CH$IUPAC: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/i3+1,4+1
 CH$LINK: CHEMSPIDER 8488970
 CH$LINK: INCHIKEY KRKNYBCHXYNGOX-CQDYUVAPSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00705.txt b/MSSJ/MSBNK-MSSJ-MSJ00705.txt
@@ -13,7 +13,7 @@ CH$NAME: Citric acid-[1,2,3,4,5,6-13C6]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C6H8O7
 CH$EXACT_MASS: 192.02700
-CH$SMILES: OC(=O)CC(O)(CC(O)=O)C(=O)O
+CH$SMILES: [13CH2]([13C](=O)O)[13C]([13CH2][13C](=O)O)([13C](=O)O)O
 CH$IUPAC: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/i1+1,2+1,3+1,4+1,5+1,6+1
 CH$LINK: CHEMSPIDER 17345064
 CH$LINK: INCHIKEY KRKNYBCHXYNGOX-IDEBNGHGSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00707.txt b/MSSJ/MSBNK-MSSJ-MSJ00707.txt
@@ -12,7 +12,7 @@ CH$NAME: alpha-Ketoglutaric acid-[1,2,3,4-13C4]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C5H6O5
 CH$EXACT_MASS: 146.02152
-CH$SMILES: C(CC(=O)O)C(=O)C(=O)O
+CH$SMILES: [13CH2]([13CH2][13C](=O)[13C](=O)O)C(=O)O
 CH$IUPAC: InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/i1+1,2+1,3+1,5+1
 CH$LINK: INCHIKEY KPGXRSRHYNQIFN-SAXDBNRNSA-N
 CH$LINK: PUBCHEM CID:91971603

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00708.txt b/MSSJ/MSBNK-MSSJ-MSJ00708.txt
@@ -13,7 +13,7 @@ CH$NAME: alpha-ketoglutaric acid-[1,2,3,4,5-13C5]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C5H6O5
 CH$EXACT_MASS: 146.02152
-CH$SMILES: C(CC(=O)O)C(=O)C(=O)O
+CH$SMILES: [13CH2]([13CH2][13C](=O)O)[13C](=O)[13C](=O)O
 CH$IUPAC: InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/i1+1,2+1,3+1,4+1,5+1
 CH$LINK: CHEMSPIDER 71078928
 CH$LINK: INCHIKEY KPGXRSRHYNQIFN-CVMUNTFWSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00710.txt b/MSSJ/MSBNK-MSSJ-MSJ00710.txt
@@ -12,7 +12,7 @@ CH$NAME: Succinic acid-[1,2,3,4-13C4]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O4
 CH$EXACT_MASS: 118.02661
-CH$SMILES: O=C(O)CCC(=O)O
+CH$SMILES: [13CH2]([13CH2][13C](=O)O)[13C](=O)O
 CH$IUPAC: InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)/i1+1,2+1,3+1,4+1
 CH$LINK: CAS 201595-67-7
 CH$LINK: CHEMSPIDER 17341241

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00712.txt b/MSSJ/MSBNK-MSSJ-MSJ00712.txt
@@ -12,7 +12,7 @@ CH$NAME: Fumaric acid-[1,2,3,4-13C4]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H4O4
 CH$EXACT_MASS: 116.01096
-CH$SMILES: C(=C/C(=O)O)\C(=O)O
+CH$SMILES: [13CH](=[13CH]/[13C](=O)O)\[13C](=O)O
 CH$IUPAC: InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+/i1+1,2+1,3+1,4+1
 CH$LINK: CHEMSPIDER 48063181
 CH$LINK: INCHIKEY VZCYOOQTPOCHFL-BHBLSLFXSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00714.txt b/MSSJ/MSBNK-MSSJ-MSJ00714.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[1-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.02153
-CH$SMILES: O=C(O)C(O)CC(=O)O
+CH$SMILES: C(C([13C](=O)O)O)C(=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i4+1
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-AZXPZELESA-N
 CH$LINK: PUBCHEM CID:25214506

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00715.txt b/MSSJ/MSBNK-MSSJ-MSJ00715.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[2-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.02152
-CH$SMILES: O=C(O)C(O)CC(=O)O
+CH$SMILES: C([13CH](C(=O)O)O)C(=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i2+1
 CH$LINK: CHEMSPIDER 49071373
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-VQEHIDDOSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00716.txt b/MSSJ/MSBNK-MSSJ-MSJ00716.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[3-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.02153
-CH$SMILES: O=C(O)C(O)CC(=O)O
+CH$SMILES: [13CH2](C(C(=O)O)O)C(=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i1+1
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-OUBTZVSYSA-N
 CH$LINK: PUBCHEM CID:153695700

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00717.txt b/MSSJ/MSBNK-MSSJ-MSJ00717.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[4-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.02153
-CH$SMILES: O=C(O)C(O)CC(=O)O
+CH$SMILES: C(C(C(=O)O)O)[13C](=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i3+1
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-LBPDFUHNSA-N
 AC$INSTRUMENT: GCMS-QP2010 Ultra (Shimadzu, Kyoto, Japan)

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00718.txt b/MSSJ/MSBNK-MSSJ-MSJ00718.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[1,2,3,4-13C4]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.02153
-CH$SMILES: O=C(O)C(O)CC(=O)O
+CH$SMILES: [13CH2]([13CH]([13C](=O)O)O)[13C](=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i1+1,2+1,3+1,4+1
 CH$LINK: CHEMSPIDER 48060182
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-JCDJMFQYSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00720.txt b/MSSJ/MSBNK-MSSJ-MSJ00720.txt
@@ -12,7 +12,7 @@ CH$NAME: Citric acid-[1,2,3,4,5,6-13C6]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C6H8O7
 CH$EXACT_MASS: 192.02701
-CH$SMILES: OC(=O)CC(O)(CC(O)=O)C(=O)O
+CH$SMILES: [13CH2]([13C](=O)O)[13C]([13CH2][13C](=O)O)([13C](=O)O)O
 CH$IUPAC: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/i1+1,2+1,3+1,4+1,5+1,6+1
 CH$LINK: CHEMSPIDER 17345064
 CH$LINK: INCHIKEY KRKNYBCHXYNGOX-IDEBNGHGSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00722.txt b/MSSJ/MSBNK-MSSJ-MSJ00722.txt
@@ -12,7 +12,7 @@ CH$NAME: Citric acid-[1,2,3,4,5,6-13C6]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C6H8O7
 CH$EXACT_MASS: 192.02701
-CH$SMILES: OC(=O)CC(O)(CC(O)=O)C(=O)O
+CH$SMILES: [13CH2]([13C](=O)O)[13C]([13CH2][13C](=O)O)([13C](=O)O)O
 CH$IUPAC: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/i1+1,2+1,3+1,4+1,5+1,6+1
 CH$LINK: CHEMSPIDER 17345064
 CH$LINK: INCHIKEY KRKNYBCHXYNGOX-IDEBNGHGSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00724.txt b/MSSJ/MSBNK-MSSJ-MSJ00724.txt
@@ -12,7 +12,7 @@ CH$NAME: Citric acid-[1,2,3,4,5,6-13C6]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C6H8O7
 CH$EXACT_MASS: 192.02701
-CH$SMILES: OC(=O)CC(O)(CC(O)=O)C(=O)O
+CH$SMILES: [13CH2]([13C](=O)O)[13C]([13CH2][13C](=O)O)([13C](=O)O)O
 CH$IUPAC: InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/i1+1,2+1,3+1,4+1,5+1,6+1
 CH$LINK: CHEMSPIDER 17345064
 CH$LINK: INCHIKEY KRKNYBCHXYNGOX-IDEBNGHGSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00726.txt b/MSSJ/MSBNK-MSSJ-MSJ00726.txt
@@ -12,7 +12,7 @@ CH$NAME: alpha-Ketoglutaric acid-[1,2,3,4-13C4]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C5H6O5
 CH$EXACT_MASS: 146.02152
-CH$SMILES: OC(=O)C(=O)CCC(=O)O
+CH$SMILES: [13CH2]([13CH2][13C](=O)[13C](=O)O)C(=O)O
 CH$IUPAC: InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/i1+1,2+1,3+1,5+1
 CH$LINK: INCHIKEY KPGXRSRHYNQIFN-SAXDBNRNSA-N
 CH$LINK: PUBCHEM CID:91971603

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00727.txt b/MSSJ/MSBNK-MSSJ-MSJ00727.txt
@@ -12,7 +12,7 @@ CH$NAME: alpha-Ketoglutaric acid-[1,2,3,4,5-13C5]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C5H6O5
 CH$EXACT_MASS: 146.02153
-CH$SMILES: OC(=O)C(=O)CCC(=O)O
+CH$SMILES: [13CH2]([13CH2][13C](=O)O)[13C](=O)[13C](=O)O
 CH$IUPAC: InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/i1+1,2+1,3+1,4+1,5+1
 CH$LINK: CHEMSPIDER 71078928
 CH$LINK: INCHIKEY KPGXRSRHYNQIFN-CVMUNTFWSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00729.txt b/MSSJ/MSBNK-MSSJ-MSJ00729.txt
@@ -12,7 +12,7 @@ CH$NAME: Succinic acid-[1,2,3,4-13C4]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O4
 CH$EXACT_MASS: 118.02661
-CH$SMILES: OC(=O)CCC(O)=O
+CH$SMILES: [13CH2]([13CH2][13C](=O)O)[13C](=O)O
 CH$IUPAC: InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)/i1+1,2+1,3+1,4+1
 CH$LINK: CHEMSPIDER 17341241
 CH$LINK: INCHIKEY KDYFGRWQOYBRFD-JCDJMFQYSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00731.txt b/MSSJ/MSBNK-MSSJ-MSJ00731.txt
@@ -12,7 +12,7 @@ CH$NAME: Fumaric acid-[1,2,3,4-13C4]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H4O4
 CH$EXACT_MASS: 116.01096
-CH$SMILES: C(=C/C(=O)O)\C(=O)O
+CH$SMILES: [13CH](=[13CH]/[13C](=O)O)\[13C](=O)O
 CH$IUPAC: InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+/i1+1,2+1,3+1,4+1
 CH$LINK: CHEMSPIDER 48063181
 CH$LINK: INCHIKEY VZCYOOQTPOCHFL-BHBLSLFXSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00733.txt b/MSSJ/MSBNK-MSSJ-MSJ00733.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[1-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.021525
-CH$SMILES: C(C(C(=O)O)O)C(=O)O
+CH$SMILES: C(C([13C](=O)O)O)C(=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i4+1
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-AZXPZELESA-N
 CH$LINK: PUBCHEM CID:25214506

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00734.txt b/MSSJ/MSBNK-MSSJ-MSJ00734.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[3-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.02152
-CH$SMILES: C(C(C(=O)O)O)C(=O)O
+CH$SMILES: [13CH2](C(C(=O)O)O)C(=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i1+1
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-OUBTZVSYSA-N
 CH$LINK: PUBCHEM CID:153695700

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00735.txt b/MSSJ/MSBNK-MSSJ-MSJ00735.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[4-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.02153
-CH$SMILES: C(C(C(=O)O)O)C(=O)O
+CH$SMILES: C(C(C(=O)O)O)[13C](=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i3+1
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-LBPDFUHNSA-N
 AC$INSTRUMENT: GCMS-TQ8040 (Shimadzu, Kyoto, Japan)

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00736.txt b/MSSJ/MSBNK-MSSJ-MSJ00736.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[1,2,3,4-13C4]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.02152
-CH$SMILES: C(C(C(=O)O)O)C(=O)O
+CH$SMILES: [13CH2]([13CH]([13C](=O)O)O)[13C](=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i1+1,2+1,3+1,4+1
 CH$LINK: CHEMSPIDER 48060182
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-JCDJMFQYSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00738.txt b/MSSJ/MSBNK-MSSJ-MSJ00738.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[1-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.02152
-CH$SMILES: C(C(C(=O)O)O)C(=O)O
+CH$SMILES: C(C([13C](=O)O)O)C(=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i4+1
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-AZXPZELESA-N
 CH$LINK: PUBCHEM CID:25214506

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00739.txt b/MSSJ/MSBNK-MSSJ-MSJ00739.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[2-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.02153
-CH$SMILES: C(C(C(=O)O)O)C(=O)O
+CH$SMILES: C([13CH](C(=O)O)O)C(=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i2+1
 CH$LINK: CHEMSPIDER 49071373
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-VQEHIDDOSA-N

diff --git a/MSSJ/MSBNK-MSSJ-MSJ00740.txt b/MSSJ/MSBNK-MSSJ-MSJ00740.txt
@@ -12,7 +12,7 @@ CH$NAME: Malic acid-[3-13C]
 CH$COMPOUND_CLASS: In vitro synthetic compound
 CH$FORMULA: C4H6O5
 CH$EXACT_MASS: 134.02153
-CH$SMILES: C(C(C(=O)O)O)C(=O)O
+CH$SMILES: [13CH2](C(C(=O)O)O)C(=O)O
 CH$IUPAC: InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/i1+1
 CH$LINK: INCHIKEY BJEPYKJPYRNKOW-OUBTZVSYSA-N
 CH$LINK: PUBCHEM CID:153695700