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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:14:00 UTC
Update Date2022-03-07 02:56:18 UTC
HMDB IDHMDB0039702
Secondary Accession Numbers
  • HMDB39702
Metabolite Identification
Common NameOryzalexin E
DescriptionOryzalexin E belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation. Oryzalexin E has been detected, but not quantified in, rice (Oryza sativa). This could make oryzalexin e a potential biomarker for the consumption of these foods. Oryzalexin E is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Oryzalexin E.
Structure
Data?1563863423
Synonyms
ValueSource
3alpha,9beta-Dihydroxy-ent-sandaracopimaradieneChEBI
ent-Sandaracopimaradien-3alpha,7beta-diolChEBI
3a,9b-Dihydroxy-ent-sandaracopimaradieneGenerator
3Α,9β-dihydroxy-ent-sandaracopimaradieneGenerator
ent-Sandaracopimaradien-3a,7b-diolGenerator
ent-Sandaracopimaradien-3α,7β-diolGenerator
Chemical FormulaC20H32O2
Average Molecular Weight304.4669
Monoisotopic Molecular Weight304.240230268
IUPAC Name(2R,4aR,4bS,7S,10aR)-7-ethenyl-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene-2,4b-diol
Traditional Name(2R,4aR,4bS,7S,10aR)-7-ethenyl-1,1,4a,7-tetramethyl-2,3,4,5,6,9,10,10a-octahydrophenanthrene-2,4b-diol
CAS Registry Number150943-96-7
SMILES
[H][C@]12CCC3=C[C@@](C)(CC[C@@]3(O)[C@]1(C)CC[C@@H](O)C2(C)C)C=C
InChI Identifier
InChI=1S/C20H32O2/c1-6-18(4)11-12-20(22)14(13-18)7-8-15-17(2,3)16(21)9-10-19(15,20)5/h6,13,15-16,21-22H,1,7-12H2,2-5H3/t15-,16-,18-,19-,20+/m1/s1
InChI KeyRGLTYROISYBKIW-BDUQCRIQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassHydrophenanthrenes
Direct ParentHydrophenanthrenes
Alternative Parents
Substituents
  • Hydrophenanthrene
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point123 - 124 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0097 g/LALOGPS
logP3.81ALOGPS
logP3.64ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.019ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.51 m³·mol⁻¹ChemAxon
Polarizability36.29 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.89731661259
DarkChem[M-H]-169.92431661259
DeepCCS[M-2H]-215.64430932474
DeepCCS[M+Na]+190.6430932474
AllCCS[M+H]+178.332859911
AllCCS[M+H-H2O]+175.232859911
AllCCS[M+NH4]+181.132859911
AllCCS[M+Na]+181.932859911
AllCCS[M-H]-183.732859911
AllCCS[M+Na-2H]-184.332859911
AllCCS[M+HCOO]-185.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Oryzalexin E[H][C@]12CCC3=C[C@@](C)(CC[C@@]3(O)[C@]1(C)CC[C@@H](O)C2(C)C)C=C2793.8Standard polar33892256
Oryzalexin E[H][C@]12CCC3=C[C@@](C)(CC[C@@]3(O)[C@]1(C)CC[C@@H](O)C2(C)C)C=C2304.0Standard non polar33892256
Oryzalexin E[H][C@]12CCC3=C[C@@](C)(CC[C@@]3(O)[C@]1(C)CC[C@@H](O)C2(C)C)C=C2404.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oryzalexin E,1TMS,isomer #1C=C[C@@]1(C)C=C2CC[C@@H]3C(C)(C)[C@H](O)CC[C@@]3(C)[C@]2(O[Si](C)(C)C)CC12402.8Semi standard non polar33892256
Oryzalexin E,1TMS,isomer #2C=C[C@@]1(C)C=C2CC[C@@H]3C(C)(C)[C@H](O[Si](C)(C)C)CC[C@@]3(C)[C@]2(O)CC12402.1Semi standard non polar33892256
Oryzalexin E,2TMS,isomer #1C=C[C@@]1(C)C=C2CC[C@@H]3C(C)(C)[C@H](O[Si](C)(C)C)CC[C@@]3(C)[C@]2(O[Si](C)(C)C)CC12384.1Semi standard non polar33892256
Oryzalexin E,1TBDMS,isomer #1C=C[C@@]1(C)C=C2CC[C@@H]3C(C)(C)[C@H](O)CC[C@@]3(C)[C@]2(O[Si](C)(C)C(C)(C)C)CC12634.9Semi standard non polar33892256
Oryzalexin E,1TBDMS,isomer #2C=C[C@@]1(C)C=C2CC[C@@H]3C(C)(C)[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@]3(C)[C@]2(O)CC12662.2Semi standard non polar33892256
Oryzalexin E,2TBDMS,isomer #1C=C[C@@]1(C)C=C2CC[C@@H]3C(C)(C)[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@]3(C)[C@]2(O[Si](C)(C)C(C)(C)C)CC12831.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oryzalexin E GC-MS (Non-derivatized) - 70eV, Positivesplash10-002r-0690000000-f5370294d497f51a221f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oryzalexin E GC-MS (2 TMS) - 70eV, Positivesplash10-003r-7053900000-647da576f4de0583fcc22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oryzalexin E GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oryzalexin E 10V, Positive-QTOFsplash10-052r-0092000000-24eb84409ea59729c4252016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oryzalexin E 20V, Positive-QTOFsplash10-05n0-6291000000-b1aa0995efc8649a656f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oryzalexin E 40V, Positive-QTOFsplash10-0udi-9130000000-d6c3dd4714c155fd19bd2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oryzalexin E 10V, Negative-QTOFsplash10-0udi-0049000000-adca20b041c8925611032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oryzalexin E 20V, Negative-QTOFsplash10-0udr-0097000000-1e9e9416d4f667152ee02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oryzalexin E 40V, Negative-QTOFsplash10-0fe0-2090000000-b963004147828af19ec72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oryzalexin E 10V, Negative-QTOFsplash10-0udi-0009000000-f9d10b76ade80bd401ad2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oryzalexin E 20V, Negative-QTOFsplash10-0udi-0019000000-97dc9de2ef2dab255fc52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oryzalexin E 40V, Negative-QTOFsplash10-0udi-1029000000-02a4e499444e8891ce432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oryzalexin E 10V, Positive-QTOFsplash10-0ap0-0093000000-007a2a1ef25dcc9f84152021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oryzalexin E 20V, Positive-QTOFsplash10-052r-0692000000-362a90923765bfcd7c432021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oryzalexin E 40V, Positive-QTOFsplash10-000i-5790000000-4f838ce109643df337ff2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB019331
KNApSAcK IDC00034093
Chemspider ID30777361
KEGG Compound IDNot Available
BioCyc IDCPD-16611
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound86289490
PDB IDNot Available
ChEBI ID78259
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.. .