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Record Information
Version2.0
Created at2022-09-08 03:35:42 UTC
Updated at2022-09-08 03:35:43 UTC
NP-MRD IDNP0261212
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,10s)-5-[(1s,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,4,6,14-tetrahydroxy-10-(3-methylbut-2-en-1-yl)-9,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-3,5,7,11,13,15-hexaen-2-one
DescriptionSanggenon O 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. (1r,10s)-5-[(1s,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,4,6,14-tetrahydroxy-10-(3-methylbut-2-en-1-yl)-9,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-3,5,7,11,13,15-hexaen-2-one is found in Morus alba, Morus cathayana and Morus mongolica. (1r,10s)-5-[(1s,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,4,6,14-tetrahydroxy-10-(3-methylbut-2-en-1-yl)-9,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-3,5,7,11,13,15-hexaen-2-one was first documented in 2012 (PMID: 21612567). Based on a literature review a small amount of articles have been published on sanggenon O (PMID: 29191050) (PMID: 31920173) (PMID: 30953888) (PMID: 25187688).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC40H36O12
Average Mass708.7160 Da
Monoisotopic Mass708.22068 Da
IUPAC Name(1R,10S)-5-[(1S,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,4,6,14-tetrahydroxy-10-(3-methylbut-2-en-1-yl)-9,17-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-3,5,7,11,13,15-hexaen-2-one
Traditional Name(1R,10S)-5-[(1S,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,4,6,14-tetrahydroxy-10-(3-methylbut-2-en-1-yl)-9,17-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-3,5,7,11,13,15-hexaen-2-one
CAS Registry NumberNot Available
SMILES
CC(C)=CC[C@@]12OC3=CC(O)=C([C@H]4C=C(C)C[C@@H]([C@H]4C(=O)C4=CC=C(O)C=C4O)C4=CC=C(O)C=C4O)C(O)=C3C(=O)[C@]1(O)OC1=CC(O)=CC=C21
InChI Identifier
InChI=1S/C40H36O12/c1-18(2)10-11-39-27-9-6-22(43)16-31(27)52-40(39,50)38(49)35-32(51-39)17-30(46)34(37(35)48)26-13-19(3)12-25(23-7-4-20(41)14-28(23)44)33(26)36(47)24-8-5-21(42)15-29(24)45/h4-10,13-17,25-26,33,41-46,48,50H,11-12H2,1-3H3/t25-,26+,33-,39+,40+/m1/s1
InChI KeyXETHJOZXBVWLLM-HCAFVXMDSA-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
Morus albaLOTUS Database
Morus cathayanaLOTUS Database
Morus mongolicaLOTUS 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
  • Alkyl-phenylketone
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Phenylketone
  • Coumaran
  • Resorcinol
  • Aryl ketone
  • Aryl alkyl ketone
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP7.85ChemAxon
pKa (Strongest Acidic)7.26ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area214.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity190.35 m³·mol⁻¹ChemAxon
Polarizability72 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00008107
Chemspider ID23327615
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15479637
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Hu X, Yu MH, Yan GR, Wang HY, Hou AJ, Lei C: Isoprenylated phenolic compounds with tyrosinase inhibition from Morus nigra. J Asian Nat Prod Res. 2018 May;20(5):488-493. doi: 10.1080/10286020.2017.1350653. Epub 2017 Nov 30. [PubMed:29191050 ]
  2. Yadav R, Selvaraj C, Aarthy M, Kumar P, Kumar A, Singh SK, Giri R: Investigating into the molecular interactions of flavonoids targeting NS2B-NS3 protease from ZIKA virus through in-silico approaches. J Biomol Struct Dyn. 2021 Jan;39(1):272-284. doi: 10.1080/07391102.2019.1709546. Epub 2020 Jan 10. [PubMed:31920173 ]
  3. Li ZR, Ma T, Guo YJ, Hu B, Niu SH, Suo FZ, Du LN, You YH, Kang WT, Liu S, Mamun M, Song QM, Pang JR, Zheng YC, Liu HM: Sanggenon O induced apoptosis of A549 cells is counterbalanced by protective autophagy. Bioorg Chem. 2019 Jun;87:688-698. doi: 10.1016/j.bioorg.2019.03.072. Epub 2019 Apr 4. [PubMed:30953888 ]
  4. Qamar MT, Mumtaz A, Naseem R, Ali A, Fatima T, Jabbar T, Ahmad Z, Ashfaq UA: Molecular Docking Based Screening of Plant Flavonoids as Dengue NS1 Inhibitors. Bioinformation. 2014 Jul 22;10(7):460-5. doi: 10.6026/97320630010460. eCollection 2014. [PubMed:25187688 ]
  5. Dat NT, Binh PT, Quynh le TP, Huong HT, Minh CV: Sanggenon C and O inhibit NO production, iNOS expression and NF-kappaB activation in LPS-induced RAW264.7 cells. Immunopharmacol Immunotoxicol. 2012 Feb;34(1):84-8. doi: 10.3109/08923973.2011.580755. Epub 2011 May 26. [PubMed:21612567 ]
  6. LOTUS database [Link]