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Record Information
Version2.0
Created at2022-09-09 12:43:22 UTC
Updated at2022-09-09 12:43:22 UTC
NP-MRD IDNP0284829
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1e,4e,6e)-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
Description1,7-Bis (4-hydroxyphenyl)-1,4,6-heptatrien-3-one, also known as 1,7-bishpho, belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. 1,7-Bis (4-hydroxyphenyl)-1,4,6-heptatrien-3-one 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. (1e,4e,6e)-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one is found in Curcuma longa, Curcuma mangga, Curcuma zedoaria, Dioscorea oppositifolia and Etlingera elatior. (1e,4e,6e)-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one was first documented in 2005 (PMID: 16038556). Based on a literature review a small amount of articles have been published on 1,7-bis (4-hydroxyphenyl)-1,4,6-heptatrien-3-one (PMID: 15730265) (PMID: 25273391) (PMID: 34705327) (PMID: 24027439).
Structure
Thumb
Synonyms
ValueSource
1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-oneMeSH
1,7-BisHPHOMeSH
Chemical FormulaC19H16O3
Average Mass292.3340 Da
Monoisotopic Mass292.10994 Da
IUPAC Name(1E,4E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
Traditional Name(1E,4E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
CAS Registry NumberNot Available
SMILES
OC1=CC=C(\C=C\C=C\C(=O)\C=C\C2=CC=C(O)C=C2)C=C1
InChI Identifier
InChI=1S/C19H16O3/c20-17(10-7-16-8-13-19(22)14-9-16)4-2-1-3-15-5-11-18(21)12-6-15/h1-14,21-22H/b3-1+,4-2+,10-7+
InChI KeyPALMCMYYFAHUGA-BPTNNVFMSA-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
Curcuma longaLOTUS Database
Curcuma manggaLOTUS Database
Curcuma zedoariaLOTUS Database
Dioscorea oppositifoliaLOTUS Database
Etlingera elatiorLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentLinear diarylheptanoids
Alternative Parents
Substituents
  • Linear 1,7-diphenylheptane skeleton
  • Hydroxycinnamic acid or derivatives
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP4.75ChemAxon
pKa (Strongest Acidic)8.77ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity91.31 m³·mol⁻¹ChemAxon
Polarizability32.83 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 ID8622469
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10447050
PDB IDNot Available
ChEBI ID65502
Good Scents IDNot Available
References
General References
  1. Abas F, Lajis NH, Shaari K, Israf DA, Stanslas J, Yusuf UK, Raof SM: A labdane diterpene glucoside from the rhizomes of Curcuma mangga. J Nat Prod. 2005 Jul;68(7):1090-3. doi: 10.1021/np0500171. [PubMed:16038556 ]
  2. Mohamad H, Lajis NH, Abas F, Ali AM, Sukari MA, Kikuzaki H, Nakatani N: Antioxidative constituents of Etlingera elatior. J Nat Prod. 2005 Feb;68(2):285-8. doi: 10.1021/np040098l. [PubMed:15730265 ]
  3. Yang MH, Chin YW, Chae HS, Yoon KD, Kim J: Anti-adipogenic constituents from Dioscorea opposita in 3T3-L1 cells. Biol Pharm Bull. 2014;37(10):1683-8. doi: 10.1248/bpb.b14-00216. [PubMed:25273391 ]
  4. Thanh Huong L, Anh Thu P, Thi Dao P, Thi Mai Huong D, Van Cuong P, Hai Dang N: Anti-Inflammatory Properties of Longifuran A, a New Benzofuran from the Stems of Amomum longiligulare. Chem Biodivers. 2021 Dec;18(12):e2100518. doi: 10.1002/cbdv.202100518. Epub 2021 Nov 16. [PubMed:34705327 ]
  5. Lo CY, Liu PL, Lin LC, Chen YT, Hseu YC, Wen ZH, Wang HM: Antimelanoma and antityrosinase from Alpinia galangal constituents. ScientificWorldJournal. 2013 Aug 21;2013:186505. doi: 10.1155/2013/186505. eCollection 2013. [PubMed:24027439 ]
  6. LOTUS database [Link]