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Record Information
Version1.0
Created at2020-10-14 21:10:02 UTC
Updated at2021-03-18 16:11:39 UTC
NP-MRD IDNP0001742
Secondary Accession NumbersNone
Natural Product Identification
Common NameAmorfrutin A
Description3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid, also known as amorfrutin a, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. It was first documented in 2021 (PMID: 34404060). Based on a literature review very few articles have been published on 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid (PMID: 34404046) (PMID: 34404029) (PMID: 34404018) (PMID: 34404014) (PMID: 34404010) (PMID: 34404008).
Structure
Thumb
Synonyms
ValueSource
3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylateGenerator
Amorfrutin aHMDB
Chemical FormulaC21H24O4
Average Mass340.4129 Da
Monoisotopic Mass340.16746 Da
IUPAC Name2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid
Traditional Name2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(CCC2=CC=CC=C2)=C(C(O)=O)C(O)=C1CC=C(C)C
InChI Identifier
InChI=1S/C21H24O4/c1-14(2)9-12-17-18(25-3)13-16(19(20(17)22)21(23)24)11-10-15-7-5-4-6-8-15/h4-9,13,22H,10-12H2,1-3H3,(H,23,24)
InChI KeyCTNFTPUIYFUXBE-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 400Mz, CHCL3(Solvent-Peak), simulated)Rgf8b2020-10-14View Spectrum
Species
Species of Origin
Species NameSourceReference
Amorpha fruticosaKNApSAcK Database
Cajanus cajanKNApSAcK Database
Glycyrrhiza acanthocarpaKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • P-methoxybenzoic acid or derivatives
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • Benzoic acid or derivatives
  • Benzoic acid
  • Anisole
  • Methoxybenzene
  • Phenoxy compound
  • Phenol ether
  • Benzoyl
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
logP10(4.37) g/LALOGPS
logP10(6.08) g/LChemAxon
logS10(-4.5) g/LALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.34 m³·mol⁻¹ChemAxon
Polarizability37.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0302011
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001743
KNApSAcK IDC00015437
Chemspider ID16430153
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound17950432
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yu H, Gild P, Pompe RS, Vetterlein MW, Ludwig TA, Soave A, Kolker M, Maurer V, Marks P, Becker A, Punke MA, Fisch M, Rink M, Dahlem R, Meyer CP: Anesthetic Technique (Spinal vs. General Anesthesia) in Holmium Laser Enucleation of the Prostate: Retrospective Analysis of Procedural and Functional Outcomes among 1,159 Patients. Urol Int. 2021 Aug 17:1-8. doi: 10.1159/000517542. [PubMed:34404060 ]
  2. Al Riyees L, Al Madani W, Firwana N, Balkhy HH, Ferwana M, Alkhudhayri A: Antibiotic Prophylaxis against Surgical Site Infection after Open Hernia Surgery: A Systematic Review and Meta-Analysis. Eur Surg Res. 2021 Aug 17:1-13. doi: 10.1159/000517404. [PubMed:34404046 ]
  3. Geer MJ, Foucar CE, Devata S, Benitez L, Perissinotti AJ, Marini BL, Bixby D: Clinical Availability of ATRA for Patients With Suspected Acute Promyelocytic Leukemia: Why Guidelines May Not Be Followed. J Natl Compr Canc Netw. 2021 Aug 17. pii: jnccn20455. doi: 10.6004/jnccn.2021.7013. [PubMed:34404029 ]
  4. Enwemeka CS, Bumah VV, Mokili JL: Pulsed blue light inactivates two strains of human coronavirus. J Photochem Photobiol B. 2021 Aug 8;222:112282. doi: 10.1016/j.jphotobiol.2021.112282. [PubMed:34404018 ]
  5. Wang Y, Liu X, Yu L, Hong X, Zhao J, Zhu J, Yuan J, Li W, Zhu X: Identification and analysis of novel microRNAs provide insights to reproductive capacity of the cultured Asian yellow pond turtle Mauremys mutica. Comp Biochem Physiol Part D Genomics Proteomics. 2021 Aug 8;40:100890. doi: 10.1016/j.cbd.2021.100890. [PubMed:34404014 ]
  6. Yang K, Li CY, An JP, Wang DR, Wang X, Wang CK, You CX: The C2H2-type zinc finger transcription factor MdZAT10 negatively regulates drought tolerance in apple. Plant Physiol Biochem. 2021 Aug 10;167:390-399. doi: 10.1016/j.plaphy.2021.08.014. [PubMed:34404010 ]
  7. Dai L, Yang H, Zhao X, Wang L: Identification of cis conformation natural rubber and proteins in Ficus altissima Blume latex. Plant Physiol Biochem. 2021 Aug 10;167:376-384. doi: 10.1016/j.plaphy.2021.08.015. [PubMed:34404008 ]
  8. Wang LJ, Gao X, Jia GX: Stomata and ROS changes during Botrytis elliptica infection in diploid and tetraploid Lilium rosthornii Diels. Plant Physiol Biochem. 2021 Aug 6;167:366-375. doi: 10.1016/j.plaphy.2021.08.008. [PubMed:34404007 ]
  9. Sawczuk R, Karpinska J, Filipowska D, Bajguz A, Hryniewicka M: Evaluation of total phenols content, anti-DPPH activity and the content of selected antioxidants in the honeybee drone brood homogenate. Food Chem. 2021 Aug 3;368:130745. doi: 10.1016/j.foodchem.2021.130745. [PubMed:34404004 ]
  10. Jiang B, Liu R, Fang X, Tong C, Chen H, Gao H: Effects of salicylic acid treatment on fruit quality and wax composition of blueberry (Vaccinium virgatum Ait). Food Chem. 2021 Aug 3;368:130757. doi: 10.1016/j.foodchem.2021.130757. [PubMed:34404000 ]
  11. Wen M, Han Z, Cui Y, Ho CT, Wan X, Zhang L: Identification of 4-O-p-coumaroylquinic acid as astringent compound of Keemun black tea by efficient integrated approaches of mass spectrometry, turbidity analysis and sensory evaluation. Food Chem. 2021 Aug 8;368:130803. doi: 10.1016/j.foodchem.2021.130803. [PubMed:34403995 ]
  12. Liang N, Hennebelle M, Gaul S, Johnson CD, Zhang Z, Kirpich IA, McClain CJ, Feldstein AE, Ramsden CE, Taha AY: Feeding mice a diet high in oxidized linoleic acid metabolites does not alter liver oxylipin concentrations. Prostaglandins Leukot Essent Fatty Acids. 2021 Jun 24;172:102316. doi: 10.1016/j.plefa.2021.102316. [PubMed:34403987 ]
  13. Amgoud Y, Senbel A, Bouhadoun A, Abdelazeem H, Ozen G, Savane I, Manikpurage HD, Mani S, Tran-Dinh A, Castier Y, Guyard A, Longrois D, Silverstein AM, Norel X: In search of pulmonary hypertension treatments: Effect of 17beta-estradiol on PGI2 pathway in human pulmonary artery. Prostaglandins Leukot Essent Fatty Acids. 2021 Aug 9;172:102321. doi: 10.1016/j.plefa.2021.102321. [PubMed:34403986 ]
  14. Xu Y, Liu Y, He T, Zhang Y, Wang M, Yuan H, Yang M: Biguanides decorated albumin nanoparticles loading nintedanib for synergic enhanced hepatocellular carcinoma therapy. Colloids Surf B Biointerfaces. 2021 Aug 4;207:112020. doi: 10.1016/j.colsurfb.2021.112020. [PubMed:34403984 ]
  15. Liu T, Song Y, Huang Z, Pu X, Wang Y, Yin G, Gou L, Weng J, Meng X: Photothermal photodynamic therapy and enhanced radiotherapy of targeting copolymer-coated liquid metal nanoparticles on liver cancer. Colloids Surf B Biointerfaces. 2021 Aug 5;207:112023. doi: 10.1016/j.colsurfb.2021.112023. [PubMed:34403983 ]