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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:20:56 UTC
Update Date2022-03-07 02:56:01 UTC
HMDB IDHMDB0039001
Secondary Accession Numbers
  • HMDB39001
Metabolite Identification
Common NamePurothionin AII
DescriptionPurothionin AII belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated. Purothionin AII has been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, common wheats (Triticum aestivum), and wheats (Triticum). This could make purothionin aii a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Purothionin AII.
Structure
Data?1563863294
Synonyms
ValueSource
a1-PurothioninHMDB
Antimycin a3HMDB
BlastmycinHMDB
BlastomycinHMDB
Peptide SP2HMDB
N-[(3S,4R,7R,8R,9S)-7-Butyl-4,9-dimethyl-8-[(3-methylbutanoyl)oxy]-2,6-dioxo-1,5-dioxonan-3-yl]-2-hydroxy-3-[(hydroxymethylidene)amino]benzene-1-carboximidateGenerator
ANTIMYCIN a(3)MeSH
Chemical FormulaC26H36N2O9
Average Molecular Weight520.572
Monoisotopic Molecular Weight520.24208076
IUPAC Name(2R,3S,6S,7R,8R)-8-butyl-3-(3-formamido-2-hydroxybenzamido)-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl 3-methylbutanoate
Traditional Name(2R,3S,6S,7R,8R)-8-butyl-3-(3-formamido-2-hydroxybenzamido)-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl 3-methylbutanoate
CAS Registry Number58239-09-1
SMILES
CCCC[C@@H]1[C@@H](OC(=O)CC(C)C)[C@H](C)OC(=O)[C@@H](NC(=O)C2=C(O)C(NC=O)=CC=C2)[C@@H](C)OC1=O
InChI Identifier
InChI=1S/C26H36N2O9/c1-6-7-9-18-23(37-20(30)12-14(2)3)16(5)36-26(34)21(15(4)35-25(18)33)28-24(32)17-10-8-11-19(22(17)31)27-13-29/h8,10-11,13-16,18,21,23,31H,6-7,9,12H2,1-5H3,(H,27,29)(H,28,32)/t15-,16+,18-,21+,23+/m1/s1
InChI KeyPVEVXUMVNWSNIG-PDPGNHKXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAcylaminobenzoic acid and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Acylaminobenzoic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Salicylamide
  • Salicylic acid or derivatives
  • Benzamide
  • Anilide
  • Tricarboxylic acid or derivatives
  • Benzoyl
  • N-arylamide
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Fatty acyl
  • Vinylogous acid
  • Carboxamide group
  • Carboxylic acid ester
  • Lactone
  • Secondary carboxylic acid amide
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
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 Solubility0.096 g/LALOGPS
logP2.88ALOGPS
logP4.06ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.51ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area157.33 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity132.68 m³·mol⁻¹ChemAxon
Polarizability54.24 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+221.40531661259
DarkChem[M-H]-215.84231661259
DeepCCS[M+H]+230.530932474
DeepCCS[M-H]-228.67530932474
DeepCCS[M-2H]-261.91630932474
DeepCCS[M+Na]+236.10630932474
AllCCS[M+H]+224.132859911
AllCCS[M+H-H2O]+222.632859911
AllCCS[M+NH4]+225.532859911
AllCCS[M+Na]+225.832859911
AllCCS[M-H]-214.332859911
AllCCS[M+Na-2H]-216.432859911
AllCCS[M+HCOO]-218.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Purothionin AIICCCC[C@@H]1[C@@H](OC(=O)CC(C)C)[C@H](C)OC(=O)[C@@H](NC(=O)C2=C(O)C(NC=O)=CC=C2)[C@@H](C)OC1=O4860.4Standard polar33892256
Purothionin AIICCCC[C@@H]1[C@@H](OC(=O)CC(C)C)[C@H](C)OC(=O)[C@@H](NC(=O)C2=C(O)C(NC=O)=CC=C2)[C@@H](C)OC1=O3492.1Standard non polar33892256
Purothionin AIICCCC[C@@H]1[C@@H](OC(=O)CC(C)C)[C@H](C)OC(=O)[C@@H](NC(=O)C2=C(O)C(NC=O)=CC=C2)[C@@H](C)OC1=O3872.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Purothionin AII,1TMS,isomer #1CCCC[C@H]1C(=O)O[C@H](C)[C@H](NC(=O)C2=CC=CC(NC=O)=C2O[Si](C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3858.3Semi standard non polar33892256
Purothionin AII,1TMS,isomer #2CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(NC=O)=C2O)[Si](C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3706.1Semi standard non polar33892256
Purothionin AII,1TMS,isomer #3CCCC[C@H]1C(=O)O[C@H](C)[C@H](NC(=O)C2=CC=CC(N(C=O)[Si](C)(C)C)=C2O)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3661.8Semi standard non polar33892256
Purothionin AII,2TMS,isomer #1CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(NC=O)=C2O[Si](C)(C)C)[Si](C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3729.3Semi standard non polar33892256
Purothionin AII,2TMS,isomer #1CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(NC=O)=C2O[Si](C)(C)C)[Si](C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3507.2Standard non polar33892256
Purothionin AII,2TMS,isomer #2CCCC[C@H]1C(=O)O[C@H](C)[C@H](NC(=O)C2=CC=CC(N(C=O)[Si](C)(C)C)=C2O[Si](C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3713.6Semi standard non polar33892256
Purothionin AII,2TMS,isomer #2CCCC[C@H]1C(=O)O[C@H](C)[C@H](NC(=O)C2=CC=CC(N(C=O)[Si](C)(C)C)=C2O[Si](C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3469.5Standard non polar33892256
Purothionin AII,2TMS,isomer #3CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(N(C=O)[Si](C)(C)C)=C2O)[Si](C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3551.8Semi standard non polar33892256
Purothionin AII,2TMS,isomer #3CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(N(C=O)[Si](C)(C)C)=C2O)[Si](C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3472.5Standard non polar33892256
Purothionin AII,3TMS,isomer #1CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(N(C=O)[Si](C)(C)C)=C2O[Si](C)(C)C)[Si](C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3630.5Semi standard non polar33892256
Purothionin AII,3TMS,isomer #1CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(N(C=O)[Si](C)(C)C)=C2O[Si](C)(C)C)[Si](C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3493.9Standard non polar33892256
Purothionin AII,1TBDMS,isomer #1CCCC[C@H]1C(=O)O[C@H](C)[C@H](NC(=O)C2=CC=CC(NC=O)=C2O[Si](C)(C)C(C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C4050.9Semi standard non polar33892256
Purothionin AII,1TBDMS,isomer #2CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(NC=O)=C2O)[Si](C)(C)C(C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3891.9Semi standard non polar33892256
Purothionin AII,1TBDMS,isomer #3CCCC[C@H]1C(=O)O[C@H](C)[C@H](NC(=O)C2=CC=CC(N(C=O)[Si](C)(C)C(C)(C)C)=C2O)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3850.1Semi standard non polar33892256
Purothionin AII,2TBDMS,isomer #1CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(NC=O)=C2O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C4106.4Semi standard non polar33892256
Purothionin AII,2TBDMS,isomer #1CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(NC=O)=C2O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3862.4Standard non polar33892256
Purothionin AII,2TBDMS,isomer #2CCCC[C@H]1C(=O)O[C@H](C)[C@H](NC(=O)C2=CC=CC(N(C=O)[Si](C)(C)C(C)(C)C)=C2O[Si](C)(C)C(C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C4053.9Semi standard non polar33892256
Purothionin AII,2TBDMS,isomer #2CCCC[C@H]1C(=O)O[C@H](C)[C@H](NC(=O)C2=CC=CC(N(C=O)[Si](C)(C)C(C)(C)C)=C2O[Si](C)(C)C(C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3792.3Standard non polar33892256
Purothionin AII,2TBDMS,isomer #3CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(N(C=O)[Si](C)(C)C(C)(C)C)=C2O)[Si](C)(C)C(C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3930.9Semi standard non polar33892256
Purothionin AII,2TBDMS,isomer #3CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(N(C=O)[Si](C)(C)C(C)(C)C)=C2O)[Si](C)(C)C(C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3806.5Standard non polar33892256
Purothionin AII,3TBDMS,isomer #1CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(N(C=O)[Si](C)(C)C(C)(C)C)=C2O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C4112.7Semi standard non polar33892256
Purothionin AII,3TBDMS,isomer #1CCCC[C@H]1C(=O)O[C@H](C)[C@H](N(C(=O)C2=CC=CC(N(C=O)[Si](C)(C)C(C)(C)C)=C2O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[C@@H](C)[C@@H]1OC(=O)CC(C)C3974.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Purothionin AII GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bt9-9700210000-0f27e6fd1b3c102c5d092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Purothionin AII GC-MS (1 TMS) - 70eV, Positivesplash10-0a4u-9020220000-150700649fbb4b6131d52017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Purothionin AII , positive-QTOFsplash10-000i-0190000000-467b420d231bf8ba876c2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purothionin AII 10V, Positive-QTOFsplash10-059f-4012940000-8581ff50d1e55da487c72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purothionin AII 20V, Positive-QTOFsplash10-0btl-9311310000-409e1abbdc89f28cebe52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purothionin AII 40V, Positive-QTOFsplash10-07e1-8890000000-f40f2175de649fda6ed52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purothionin AII 10V, Negative-QTOFsplash10-02di-5290230000-6eae5c2de6216aea03842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purothionin AII 20V, Negative-QTOFsplash10-0gdj-4590300000-487bb79b742abf667f9a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purothionin AII 40V, Negative-QTOFsplash10-002f-9710000000-de46145a0f711c0b699e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purothionin AII 10V, Positive-QTOFsplash10-02g9-1400940000-a88b30ccafd3365ba9fa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purothionin AII 20V, Positive-QTOFsplash10-03du-3901100000-221b4772ad6699860da02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purothionin AII 40V, Positive-QTOFsplash10-000f-6911000000-9e1c4405bd53654f0fc02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purothionin AII 10V, Negative-QTOFsplash10-014i-0000690000-82aa77d650ed9aeb79e02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purothionin AII 20V, Negative-QTOFsplash10-0006-9216400000-581e8cf4db7a34bcd4742021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Purothionin AII 40V, Negative-QTOFsplash10-0006-9430000000-db6c61ee25563ccc7ecc2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB018492
KNApSAcK IDNot Available
Chemspider ID215110
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound245869
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .