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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:06:51 UTC
Update Date2021-09-26 23:02:42 UTC
HMDB IDHMDB0250956
Secondary Accession NumbersNone
Metabolite Identification
Common NameDehydromonocrotaline
Description5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹⁶]hexadeca-10(16),11-diene-3,7-dione belongs to the class of organic compounds known as pyrrolizines. Pyrrolizines are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring. Based on a literature review very few articles have been published on 5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0¹³,¹⁶]hexadeca-10(16),11-diene-3,7-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dehydromonocrotaline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dehydromonocrotaline 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
SynonymsNot Available
Chemical FormulaC16H21NO6
Average Molecular Weight323.345
Monoisotopic Molecular Weight323.1368874
IUPAC Name5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^{13,16}]hexadeca-10(16),11-diene-3,7-dione
Traditional Name5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^{13,16}]hexadeca-10(16),11-diene-3,7-dione
CAS Registry NumberNot Available
SMILES
CC1C(=O)OC2CCN3C=CC(COC(=O)C(C)(O)C1(C)O)=C23
InChI Identifier
InChI=1S/C16H21NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,6,9,11,20-21H,5,7-8H2,1-3H3
InChI KeyZONSVLURFASOJK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolizines. Pyrrolizines are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolizines
Sub ClassNot Available
Direct ParentPyrrolizines
Alternative Parents
Substituents
  • Pyrrolizine
  • Dicarboxylic acid or derivatives
  • Pyrrole
  • Tertiary alcohol
  • Heteroaromatic compound
  • 1,2-diol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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(0.99) g/LALOGPS
logP10(0.45) g/LChemAxon
logS10(-2) g/LALOGPS
pKa (Strongest Acidic)11.49ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.57 m³·mol⁻¹ChemAxon
Polarizability31.7 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DehydromonocrotalineCC1C(=O)OC2CCN3C=CC(COC(=O)C(C)(O)C1(C)O)=C233597.0Standard 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.
DehydromonocrotalineCC1C(=O)OC2CCN3C=CC(COC(=O)C(C)(O)C1(C)O)=C232275.9Standard 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.
DehydromonocrotalineCC1C(=O)OC2CCN3C=CC(COC(=O)C(C)(O)C1(C)O)=C232638.2Semi 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 ID501684
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound577090
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 ]