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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 01:15:31 UTC
Update Date2022-03-07 02:49:31 UTC
HMDB IDHMDB0006345
Secondary Accession Numbers
  • HMDB06345
Metabolite Identification
Common NameL-Citramalyl-CoA
DescriptionL-Citramalyl-CoA is an intermediate in C5-Branched dibasic acid metabolism. L-Citramalyl-CoA is the 3rd to last step in the synthesis of (R)-Acetoin and is converted from L-Citramalate via the enzyme citramalate CoA-transferase (EC 2.8.3.7). It is then converted to Pyruvate via the enzyme citramalate-CoA lyase (EC 4.1.3.25).
Structure
Data?1582752381
Synonyms
ValueSource
(3S)-Citramalyl-CoAHMDB
(3S)-Citramalyl-coenzyme AHMDB
(2S)-4-({2-[(3-{[(2R)-4-({[({[(2R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-hydroxy-2-methyl-4-oxobutanoateGenerator, HMDB
(2S)-4-({2-[(3-{[(2R)-4-({[({[(2R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-2-hydroxy-2-methyl-4-oxobutanoateGenerator, HMDB
(2S)-4-({2-[(3-{[(2R)-4-({[({[(2R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-2-hydroxy-2-methyl-4-oxobutanoic acidGenerator, HMDB
Chemical FormulaC26H42N7O20P3S
Average Molecular Weight897.633
Monoisotopic Molecular Weight897.141817045
IUPAC Name(2S)-4-[(2-{3-[(2R)-3-[({[({[(2R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-2-hydroxy-2-methyl-4-oxobutanoic acid
Traditional Name(2S)-4-[(2-{3-[(2R)-3-{[({[(2R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-2-hydroxy-2-methyl-4-oxobutanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(C(=O)NCCC(=O)NCCSC(=O)C[C@](C)(O)C(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@@H](O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C26H42N7O20P3S/c1-25(2,19(37)22(38)29-5-4-14(34)28-6-7-57-15(35)8-26(3,41)24(39)40)10-50-56(47,48)53-55(45,46)49-9-13-18(52-54(42,43)44)17(36)23(51-13)33-12-32-16-20(27)30-11-31-21(16)33/h11-13,17-19,23,36-37,41H,4-10H2,1-3H3,(H,28,34)(H,29,38)(H,39,40)(H,45,46)(H,47,48)(H2,27,30,31)(H2,42,43,44)/t13-,17+,18?,19+,23-,26+/m1/s1
InChI KeyXYGOWHUIVNMEIA-KKAINBEZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-hydroxyacyl coas. These are organic compounds containing a 3-hydroxyl acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent3-hydroxyacyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Hydroxy fatty acid
  • Monoalkyl phosphate
  • Thia fatty acid
  • Imidolactam
  • Fatty amide
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Alkyl phosphate
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Tertiary alcohol
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Carbothioic s-ester
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Secondary alcohol
  • Carboxamide group
  • Thiocarboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Sulfenyl compound
  • Organoheterocyclic compound
  • Azacycle
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid
  • Oxacycle
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Carbonyl group
  • Primary amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.2 g/LALOGPS
logP-0.48ALOGPS
logP-7.4ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.96ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area421.16 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity189.15 m³·mol⁻¹ChemAxon
Polarizability78.31 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+241.75630932474
DeepCCS[M-H]-239.29330932474
DeepCCS[M-2H]-273.56330932474
DeepCCS[M+Na]+248.93830932474
AllCCS[M+H]+260.332859911
AllCCS[M+H-H2O]+260.832859911
AllCCS[M+NH4]+259.732859911
AllCCS[M+Na]+259.532859911
AllCCS[M-H]-263.732859911
AllCCS[M+Na-2H]-268.032859911
AllCCS[M+HCOO]-272.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-Citramalyl-CoA[H][C@](O)(C(=O)NCCC(=O)NCCSC(=O)C[C@](C)(O)C(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@@H](O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N5918.9Standard polar33892256
L-Citramalyl-CoA[H][C@](O)(C(=O)NCCC(=O)NCCSC(=O)C[C@](C)(O)C(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@@H](O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N4444.7Standard non polar33892256
L-Citramalyl-CoA[H][C@](O)(C(=O)NCCC(=O)NCCSC(=O)C[C@](C)(O)C(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@@H](O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N6803.0Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Citramalyl-CoA 10V, Positive-QTOFsplash10-000i-1922000140-82bee10a39ad1b208bc62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Citramalyl-CoA 20V, Positive-QTOFsplash10-000i-0924000000-5db48af43ffd7e5df2672017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Citramalyl-CoA 40V, Positive-QTOFsplash10-000i-1911000000-fff0268fffc54c593b852017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Citramalyl-CoA 10V, Negative-QTOFsplash10-005i-9810030360-9d923718cb8b8990c1652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Citramalyl-CoA 20V, Negative-QTOFsplash10-0040-6910120020-c06ba8a9737269fa05d82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Citramalyl-CoA 40V, Negative-QTOFsplash10-057i-5900100000-220fc3c23724941ebc4d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Citramalyl-CoA 10V, Positive-QTOFsplash10-0002-0000000090-a716efa11b6399f050d22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Citramalyl-CoA 20V, Positive-QTOFsplash10-01p9-0710001290-28f2989034ca83d12f2c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Citramalyl-CoA 40V, Positive-QTOFsplash10-0006-0249000100-2853a668fea2caf8835f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Citramalyl-CoA 10V, Negative-QTOFsplash10-0006-0000000090-ae0b14e6c1e325212c9c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Citramalyl-CoA 20V, Negative-QTOFsplash10-015c-7900001370-40675a0b527b9b5dc1512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Citramalyl-CoA 40V, Negative-QTOFsplash10-002b-7304705930-7637808ffdd9f7e1f74a2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023897
KNApSAcK IDNot Available
Chemspider ID35015991
KEGG Compound IDC01011
BioCyc IDNot Available
BiGG ID36606
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477827
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDCITMCOA_L
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available