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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:07:05 UTC
Update Date2021-09-26 23:02:42 UTC
HMDB IDHMDB0250960
Secondary Accession NumbersNone
Metabolite Identification
Common NameDehydrotumulosic acid
DescriptionDehydrotumulosic acid, also known as dehydrotumulosate, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Dehydrotumulosic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Dehydrotumulosic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dehydrotumulosic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
DehydrotumulosateGenerator
Dehydrotumulosic acid, (3alpha,16alpha)-isomerMeSH
2-{5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-dien-14-yl}-6-methyl-5-methylideneheptanoateGenerator
Chemical FormulaC31H48O4
Average Molecular Weight484.721
Monoisotopic Molecular Weight484.355260026
IUPAC Name2-{5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-dien-14-yl}-6-methyl-5-methylideneheptanoic acid
Traditional Name2-{5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-dien-14-yl}-6-methyl-5-methylideneheptanoic acid
CAS Registry NumberNot Available
SMILES
CC(C)C(=C)CCC(C1C(O)CC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3=CCC12C)C(O)=O
InChI Identifier
InChI=1S/C31H48O4/c1-18(2)19(3)9-10-20(27(34)35)26-23(32)17-31(8)22-11-12-24-28(4,5)25(33)14-15-29(24,6)21(22)13-16-30(26,31)7/h11,13,18,20,23-26,32-33H,3,9-10,12,14-17H2,1-2,4-8H3,(H,34,35)
InChI KeyLADJWZMBZBVBSB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Ergosterol-skeleton
  • Ergostane-skeleton
  • Dihydroxy bile acid, alcohol, or derivatives
  • Steroid acid
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 16-hydroxysteroid
  • Delta-7-steroid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Fatty acyl
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(6.2) g/LALOGPS
logP10(5.32) g/LChemAxon
logS10(-4.9) g/LALOGPS
pKa (Strongest Acidic)4.75ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity142.42 m³·mol⁻¹ChemAxon
Polarizability57.87 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dehydrotumulosic acidCC(C)C(=C)CCC(C1C(O)CC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3=CCC12C)C(O)=O4542.7Standard polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Dehydrotumulosic acidCC(C)C(=C)CCC(C1C(O)CC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3=CCC12C)C(O)=O3224.4Standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Dehydrotumulosic acidCC(C)C(=C)CCC(C1C(O)CC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3=CCC12C)C(O)=O3898.1Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22134159
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]