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Showing Compound 15-Acetoxyscirpen-3,4-diol (FDB014626)

Record Information
Version1.0
Creation date2010-04-08 22:11:23 UTC
Update date2015-07-20 23:09:36 UTC
Primary IDFDB014626
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name15-Acetoxyscirpen-3,4-diol
DescriptionErgocristine belongs to the class of organic compounds known as ergotamines, dihydroergotamines, and derivatives. These are organic compounds containing an ergotamine moiety, which is structurally characterized by a benzyl substituent attached to the piperazine ring of the ergopeptine backbone. Ingestion of ergoline alkaloids is known to cause the disease ergotism. Ergocristine is a very strong basic compound (based on its pKa). Ergocristine is a potentially toxic compound. Ergocristine is an alkaloid of the ergoline family. Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Ergometrine is also known to have a non-receptor specific oxytocic activity. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade.
CAS Number2623-22-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
15-Acetoxyscirpen-3,4-diolHMDB
15-AcetoxyscirpendiolHMDB
15-AcetoxyscirpenolHMDB
15-AcetylscirpenetriolHMDB
15-mono-O-AcetylscirpenolHMDB
15-O-AcetylscirpenetriolHMDB
4-DeacetylanguidinHMDB
ANGUIDINE, desacetyl(15-acetoxyscirpene-3,4-diol-BL5732)HMDB
DeacetylanguidinHMDB
DesacetylanguidineHMDB
{10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-yl}methyl acetic acidGenerator
MonoacetoxyscirpenolMeSH
(3a,4b)-15-Acetoxyscirpen-3,4-diolmanual
15-Mono-O-acetylscirpenolbiospider
ANGUIDINE, desacetyl(15-acetoxyscirpene-3,4-diol-bl5732)HMDB
Predicted Properties
PropertyValueSource
Water Solubility4.4 g/LALOGPS
logP0.57ALOGPS
logP-0.064ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)12.98ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area88.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.95 m³·mol⁻¹ChemAxon
Polarizability33.22 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H24O6
IUPAC name10',11'-dihydroxy-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate
InChI IdentifierInChI=1S/C17H24O6/c1-9-4-5-16(7-21-10(2)18)11(6-9)23-14-12(19)13(20)15(16,3)17(14)8-22-17/h6,11-14,19-20H,4-5,7-8H2,1-3H3
InChI KeyIRXDUBNENLKYTC-UHFFFAOYSA-N
Isomeric SMILESCC(=O)OCC12CCC(C)=CC1OC1C(O)C(O)C2(C)C11CO1
Average Molecular Weight324.3689
Monoisotopic Molecular Weight324.1572885
Classification
Description Belongs to the class of organic compounds known as ergotamines, dihydroergotamines, and derivatives. These are organic compounds containing an ergotamine moiety, which is structurally characterized by a benzyl substituent attached to the piperazine ring of the ergopeptine backbone.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassErgoline and derivatives
Sub ClassLysergic acids and derivatives
Direct ParentErgotamines, dihydroergotamines, and derivatives
Alternative Parents
Substituents
  • Ergotamine
  • Hybrid peptide
  • Alpha-dipeptide
  • Lysergic acid amide
  • Indoloquinoline
  • Benzoquinoline
  • Quinoline-3-carboxamide
  • N-acyl-alpha amino acid or derivatives
  • Pyrroloquinoline
  • Quinoline
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Isoindole or derivatives
  • Aralkylamine
  • N-alkylpiperazine
  • Monocyclic benzene moiety
  • 1,4-diazinane
  • Benzenoid
  • Oxazolidinone
  • Piperazine
  • Pyrrole
  • Pyrrolidine
  • Heteroaromatic compound
  • Oxazolidine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Tertiary amine
  • Amino acid or derivatives
  • Lactam
  • Tertiary aliphatic amine
  • Secondary carboxylic acid amide
  • Orthocarboxylic acid derivative
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Alkanolamine
  • Oxacycle
  • Azacycle
  • Organooxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Amine
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Environmental role:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.95%; H 7.46%; O 29.59%DFC
Melting PointMp 172-173°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -25 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4l-7910000000-ee625a230f247ef2a1b9Spectrum
Predicted GC-MS15-Acetoxyscirpen-3,4-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-8983000000-2b3ece0fc071e0a02ae9Spectrum
Predicted GC-MS15-Acetoxyscirpen-3,4-diol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uml-9457500000-f0e1f929dc06f83e63b1Spectrum
Predicted GC-MS15-Acetoxyscirpen-3,4-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS15-Acetoxyscirpen-3,4-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00or-1069000000-8a4acc9ad6cac1bfcdabSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-1692000000-99bcb7b55345010c80a6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014m-9750000000-f52ad6fdbbd8ca8364c1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3029000000-24597e127f3228e2aac5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9445000000-1e097d94c61293160ccaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1001-9800000000-44db093f8409c92cb252Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0092000000-b8bd80fe17ca733ae85aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1091000000-e2b4db216b5792f8eeaeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adl-3795000000-3e73cb01a148dd3b7cacSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-2094000000-79008c91e52055b40fa5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-8090000000-2d13b1b0a398f7c82ecbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-9cebaa91e008a1743094Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
ChemSpider ID380266
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID429922
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35848
CRC / DFC (Dictionary of Food Compounds) IDJPF97-A:JSZ59-H
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00012643
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference