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Record Information
Version2.0
Created at2022-09-02 14:00:07 UTC
Updated at2022-09-02 14:00:07 UTC
NP-MRD IDNP0156749
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-mucronulatol
DescriptionMucronulatol belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. Thus, mucronulatol is considered to be a flavonoid. Mucronulatol 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. (-)-mucronulatol is found in Astragalus cicer, Centrolobium sclerophyllum, Dalbergia ecastaphyllum, Dalbergia odorifera, Dalbergia parviflora, Indigofera aspalathoides and Robinia pseudoacacia. (-)-mucronulatol was first documented in 2000 (PMID: 21214467). Based on a literature review very few articles have been published on mucronulatol (PMID: 18538108).
Structure
Thumb
Synonyms
ValueSource
(-)-MucronulatolChEBI
3',7-Dihydroxy-2',4'-dimethoxyisoflavanMeSH
Chemical FormulaC17H18O5
Average Mass302.3260 Da
Monoisotopic Mass302.11542 Da
IUPAC Name(3S)-3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
Traditional Name(-)-mucronulatol
CAS Registry NumberNot Available
SMILES
COC1=CC=C([C@H]2COC3=CC(O)=CC=C3C2)C(OC)=C1O
InChI Identifier
InChI=1S/C17H18O5/c1-20-14-6-5-13(17(21-2)16(14)19)11-7-10-3-4-12(18)8-15(10)22-9-11/h3-6,8,11,18-19H,7,9H2,1-2H3/t11-/m1/s1
InChI KeyNUNFZNIXYWTZMW-LLVKDONJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent3'-hydroxy,4'-methoxyisoflavonoids
Alternative Parents
Substituents
  • 3'-hydroxy,4'-methoxyisoflavonoid
  • 2p-methoxyisoflavonoid-skeleton
  • Isoflavanol
  • Hydroxyisoflavonoid
  • Isoflavan
  • Benzopyran
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Chromane
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.76ALOGPS
logP2.88ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.25ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.15 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity81.89 m³·mol⁻¹ChemAxon
Polarizability32.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002551
Chemspider ID391133
KEGG Compound IDC10507
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442811
PDB IDNot Available
ChEBI ID7014
Good Scents IDNot Available
References
General References
  1. Diaz-Carballo D, Freista Hler M, Malak S, Bardenheuer W, Reusch HP: Mucronulatol from Caribbean propolis exerts cytotoxic effects on human tumor cell lines. Int J Clin Pharmacol Ther. 2008 May;46(5):226-35. doi: 10.5414/cpp46226. [PubMed:18538108 ]
  2. Tian F, McLaughlin JL: Bioactive flavonoids from the black locust tree, robinia pseudoacacia. Pharm Biol. 2000;38(3):229-34. doi: 10.1076/1388-0209(200007)3831-SFT229. [PubMed:21214467 ]
  3. LOTUS database [Link]