Np mrd loader

Record Information
Version2.0
Created at2022-09-04 22:29:53 UTC
Updated at2022-09-04 22:29:53 UTC
NP-MRD IDNP0203114
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethyl-2-propanoylcyclohexa-2,4-dien-1-one
DescriptionAspidin PB belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 4-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethyl-2-propanoylcyclohexa-2,4-dien-1-one is found in Dryopteris fragrans. 4-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethyl-2-propanoylcyclohexa-2,4-dien-1-one was first documented in 2006 (PMID: 17039877). Based on a literature review a significant number of articles have been published on Aspidin PB (PMID: 30450082) (PMID: 26596576) (PMID: 26181229) (PMID: 26054450) (PMID: 24530873) (PMID: 23178381).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC24H30O8
Average Mass446.4960 Da
Monoisotopic Mass446.19407 Da
IUPAC Name4-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethyl-2-propanoylcyclohexa-2,4-dien-1-one
Traditional Name4-[(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylphenyl)methyl]-3,5-dihydroxy-6,6-dimethyl-2-propanoylcyclohexa-2,4-dien-1-one
CAS Registry NumberNot Available
SMILES
CCCC(=O)C1=C(O)C(CC2=C(O)C(C)(C)C(=O)C(C(=O)CC)=C2O)=C(O)C(C)=C1OC
InChI Identifier
InChI=1S/C24H30O8/c1-7-9-15(26)16-19(28)12(18(27)11(3)21(16)32-6)10-13-20(29)17(14(25)8-2)23(31)24(4,5)22(13)30/h27-30H,7-10H2,1-6H3
InChI KeyVVTPVUMYNQURDS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Dryopteris fragransLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • Methoxyphenol
  • Phenoxy compound
  • O-cresol
  • P-cresol
  • Phenol ether
  • Resorcinol
  • Anisole
  • Methoxybenzene
  • Aryl alkyl ketone
  • Benzoyl
  • Alkyl aryl ether
  • Toluene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Cyclic ketone
  • Ether
  • Enol
  • Organic oxide
  • Hydrocarbon derivative
  • 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
logP4.42ChemAxon
pKa (Strongest Acidic)3.8ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area141.36 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity121.64 m³·mol⁻¹ChemAxon
Polarizability46.51 ųChemAxon
Number of Rings2ChemAxon
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 IDNot Available
Chemspider ID157839
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound181448
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ye L, Lin P, Du W, Wang Y, Tang C, Shen Z: Preparation, Antidermatophyte Activity, and Mechanism of Methylphloroglucinol Derivatives. Front Microbiol. 2018 Nov 2;9:2262. doi: 10.3389/fmicb.2018.02262. eCollection 2018. [PubMed:30450082 ]
  2. Gao C, Guo N, Li N, Peng X, Wang P, Wang W, Luo M, Fu YJ: Investigation of antibacterial activity of aspidin BB against Propionibacterium acnes. Arch Dermatol Res. 2016 Mar;308(2):79-86. doi: 10.1007/s00403-015-1603-x. Epub 2015 Nov 23. [PubMed:26596576 ]
  3. Wan D, Jiang C, Hua X, Wang T, Chai Y: Cell cycle arrest and apoptosis induced by aspidin PB through the p53/p21 and mitochondria-dependent pathways in human osteosarcoma cells. Anticancer Drugs. 2015 Oct;26(9):931-41. doi: 10.1097/CAD.0000000000000269. [PubMed:26181229 ]
  4. Song R, Li G, Li S: Aspidin PB, a novel natural anti-fibrotic compound, inhibited fibrogenesis in TGF-beta1-stimulated keloid fibroblasts via PI-3K/Akt and Smad signaling pathways. Chem Biol Interact. 2015 Aug 5;238:66-73. doi: 10.1016/j.cbi.2015.06.005. Epub 2015 Jun 6. [PubMed:26054450 ]
  5. Yang MH, Kim J, Khan IA, Walker LA, Khan SI: Nonsteroidal anti-inflammatory drug activated gene-1 (NAG-1) modulators from natural products as anti-cancer agents. Life Sci. 2014 Apr 1;100(2):75-84. doi: 10.1016/j.lfs.2014.01.075. Epub 2014 Feb 12. [PubMed:24530873 ]
  6. Sun Y, Gao C, Luo M, Wang W, Gu C, Zu Y, Li J, Efferth T, Fu Y: Aspidin PB, a phloroglucinol derivative, induces apoptosis in human hepatocarcinoma HepG2 cells by modulating PI3K/Akt/GSK3beta pathway. Chem Biol Interact. 2013 Jan 25;201(1-3):1-8. doi: 10.1016/j.cbi.2012.11.005. Epub 2012 Nov 21. [PubMed:23178381 ]
  7. Shen ZB, Luo WY, Yan YS, Zhu JF: [Studies on phloroglucinol derivatives of Dryopteris fragrans L]. Zhong Yao Cai. 2006 Jun;29(6):560-1. [PubMed:17039877 ]
  8. LOTUS database [Link]