Record Information
Version1.0
Creation date2010-04-08 22:12:00 UTC
Update date2019-11-26 03:12:04 UTC
Primary IDFDB015696
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBryonolic acid
DescriptionBryonolic acid, also known as bryonolate, belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. Bryonolic acid has been detected, but not quantified in, several different foods, such as calabashes (Lagenaria siceraria), fruits, olives (Olea europaea), towel gourds (Luffa aegyptiaca), and watermelons (Citrullus lanatus). This could make bryonolic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Bryonolic acid.
CAS Number24480-45-3
Structure
Thumb
Synonyms
SynonymSource
BryonolateGenerator
3beta-Hydroxy-D-C-friedoolean-8-en-29-Oic acidMeSH
10-Hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylateGenerator
Bryonolic acidMeSH
3beta-Hydroxy-D-C-friedoolean-8-en-29-oic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.0019 g/LALOGPS
logP6.46ALOGPS
logP6.55ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity133.36 m³·mol⁻¹ChemAxon
Polarizability55.31 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC30H48O3
IUPAC name10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylic acid
InChI IdentifierInChI=1S/C30H48O3/c1-25(2)21-9-8-20-19(28(21,5)12-11-23(25)31)10-13-30(7)22-18-27(4,24(32)33)15-14-26(22,3)16-17-29(20,30)6/h21-23,31H,8-18H2,1-7H3,(H,32,33)
InChI KeyBHVJSLPLFOAMEV-UHFFFAOYSA-N
Isomeric SMILESCC1(C)C(O)CCC2(C)C1CCC1=C2CCC2(C)C3CC(C)(CCC3(C)CCC12C)C(O)=O
Average Molecular Weight456.7003
Monoisotopic Molecular Weight456.360345402
Classification
Description Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentCyclic alcohols and derivatives
Alternative Parents
Substituents
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.90%; H 10.59%; O 10.51%DFC
Melting PointMp 300-303°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +24 (c, 2.53 in Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBryonolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-054o-0006900000-47c5495138a6a3d22434Spectrum
Predicted GC-MSBryonolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1000390000-ed6c99826cbc411f97a3Spectrum
Predicted GC-MSBryonolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0001900000-5b6fbd935c1a2451f22f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p6-0017900000-3a4e1d2d76fe46c4366b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7x-1239200000-40b041b6d83945f91acd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-12a0901f1a3a919049d72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fu-0003900000-ceee18003722bfcf79d12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-1009800000-72ad4e1761ea26570ae52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-0d11296813b631a2140f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-0d11296813b631a2140f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0000900000-1dfe2becea314522f6532021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-8b863856556753a398952021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052v-1119500000-c9ca7ec153e935bc21e72021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bi-3932200000-1a368c6b10899c831a402021-09-23View Spectrum
NMRNot Available
ChemSpider ID437577
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID500182
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36757
CRC / DFC (Dictionary of Food Compounds) IDJPG66-V:KGG47-Q
EAFUS IDNot Available
Dr. Duke IDBRYONOLIC-ACID
BIGG IDNot Available
KNApSAcK IDC00029859
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 / Bioactivities
DescriptorIDDefinitionReference
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti anaphylactic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.