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Record Information
Version2.0
Created at2020-12-09 00:57:09 UTC
Updated at2021-07-15 16:47:25 UTC
NP-MRD IDNP0003804
Secondary Accession NumbersNone
Natural Product Identification
Common NameTerphenyllin
Provided ByNPAtlasNPAtlas Logo
DescriptionTerphenyllin 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. Terphenyllin is found in Aspergillus, Aspergillus campestris and Aspergillus candidus. Terphenyllin was first documented in 1975 (PMID: 1150533). Based on a literature review a small amount of articles have been published on terphenyllin (PMID: 21486068) (PMID: 22196792) (PMID: 1011375) (PMID: 613931).
Structure
Data?1624573904
SynonymsNot Available
Chemical FormulaC20H18O5
Average Mass338.3590 Da
Monoisotopic Mass338.11542 Da
IUPAC Name4-(4-hydroxyphenyl)-3,6-dimethoxy-[1,1'-biphenyl]-2,4'-diol
Traditional Name4-(4-hydroxyphenyl)-3,6-dimethoxy-[1,1'-biphenyl]-2,4'-diol
CAS Registry NumberNot Available
SMILES
COC1=C(C(O)=C(OC)C(=C1)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C20H18O5/c1-24-17-11-16(12-3-7-14(21)8-4-12)20(25-2)19(23)18(17)13-5-9-15(22)10-6-13/h3-11,21-23H,1-2H3
InChI KeyYNEMPXKRLPZFAX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
AspergillusNPAtlas
Aspergillus campestrisLOTUS Database
Aspergillus candidusLOTUS Database
Species Where Detected
Species NameSourceReference
Aspergillus candidus NRCC 14509KNApSAcK Database
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as p-terphenyls. These are terphenyls with a structure containing the 1,4-diphenylbenzene skeleton.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassTerphenyls
Direct ParentP-terphenyls
Alternative Parents
Substituents
  • Para-terphenyl
  • Biphenyl
  • P-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP3.61ALOGPS
logP4.04ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.19ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.15 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.2 m³·mol⁻¹ChemAxon
Polarizability36.53 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA021154
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00018046
Chemspider ID90750
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID67537
Good Scents IDNot Available
References
General References
  1. Marchelli R, Vining LC: Terphenyllin, a novel p-terphenyl metabolite from aspergillus candidus. J Antibiot (Tokyo). 1975 Apr;28(4):328-31. doi: 10.7164/antibiotics.28.328. [PubMed:1150533 ]
  2. Cai S, Sun S, Zhou H, Kong X, Zhu T, Li D, Gu Q: Prenylated Polyhydroxy-p-terphenyls from Aspergillus taichungensis ZHN-7-07. J Nat Prod. 2011 May 27;74(5):1106-10. doi: 10.1021/np2000478. Epub 2011 Apr 12. [PubMed:21486068 ]
  3. Guo ZK, Yan T, Guo Y, Song YC, Jiao RH, Tan RX, Ge HM: p-Terphenyl and diterpenoid metabolites from endophytic Aspergillus sp. YXf3. J Nat Prod. 2012 Jan 27;75(1):15-21. doi: 10.1021/np200321s. Epub 2011 Dec 23. [PubMed:22196792 ]
  4. Ohtsubo K, Horiuchi T, Hatanaka Y, Saito M: Hepato- and cardiotoxicity of xanthoascin, a new metabolite of A. candidus Link, to mice. I. Blood chemistry and histological changes in mice. Jpn J Exp Med. 1976 Oct;46(5):277-87. [PubMed:1011375 ]
  5. Ohtsubo K, Saito M: Hepato-and cardiotoxicity of xanthoascin, a new xanthocillin analogue produced by Aspergillus candidus. II. A preliminary electron microscopic observation of the heart and lung with intranuclear myelin-like figures. Ann Nutr Aliment. 1977;31(4-6):771-80. [PubMed:613931 ]