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Showing NP-Card for Myricanone (NP0073083)

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Record Information
Version2.0
Created at2022-04-28 18:20:39 UTC
Updated at2022-04-28 18:20:39 UTC
NP-MRD IDNP0073083
Secondary Accession NumbersNone
Natural Product Identification
Common NameMyricanone
DescriptionMulberranol belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position. Mulberranol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Mulberranol has been detected, but not quantified in, fruits. Myricanone is found in Morella cerifera, Morella esculenta, Morella nana, Myrica rubra , Myrica gale, Myrica nagi and Nageia nagi. This could make mulberranol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0073083 (Myricanone)


  Mrv0541 05061305302D          

 26 28  0  0  0  0            999 V2000
   -1.2169    2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2169    1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314    0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314    0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2169   -0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -1.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0709   -1.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6134   -2.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6421   -1.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3848   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698    0.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244    0.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555    2.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410    2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410    1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265    0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    2.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410    3.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265    3.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265    2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2121    2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2121    1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4656   -1.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 24  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 25  2  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 21  2  0  0  0  0
 15 16  2  0  0  0  0
 16 23  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 26  1  0  0  0  0
 26 10  1  0  0  0  0
M  END
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3D MOL for NP0073083 (Myricanone)

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3D SDF for NP0073083 (Myricanone)

  Mrv0541 05061305302D          

 26 28  0  0  0  0            999 V2000
   -1.2169    2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2169    1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314    0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314    0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2169   -0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -1.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0709   -1.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6134   -2.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6421   -1.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3848   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698    0.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244    0.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3555    2.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410    2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410    1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265    0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    2.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410    3.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265    3.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9265    2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2121    2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2121    1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4656   -1.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 24  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 25  2  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 21  2  0  0  0  0
 15 16  2  0  0  0  0
 16 23  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 26  1  0  0  0  0
 26 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073083

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(=O)CCCC2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O5/c1-25-20-17-12-14(19(24)21(20)26-2)5-3-4-6-15(22)9-7-13-8-10-18(23)16(17)11-13/h8,10-12,23-24H,3-7,9H2,1-2H3

> <INCHI_KEY>
ZTSNTUQTNQSIDC-UHFFFAOYSA-N

> <FORMULA>
C21H24O5

> <MOLECULAR_WEIGHT>
356.4123

> <EXACT_MASS>
356.162373878

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.67042342492958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,15-dihydroxy-16,17-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one

> <ALOGPS_LOGP>
3.95

> <JCHEM_LOGP>
4.3047404789999995

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.286591601076227

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.980231858557207

> <JCHEM_PKA_STRONGEST_BASIC>
-4.638350841654973

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
100.00899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,15-dihydroxy-16,17-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0073083 (Myricanone)
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PDB for NP0073083 (Myricanone)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  O   UNK     0      -2.272   4.013   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.272   2.473   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.605   1.703   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.605   0.163   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.272  -0.607   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.873  -2.094   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.132  -1.970   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.145  -4.571   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.199  -3.032   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.585  -0.763   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.864   0.062   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.152   1.384   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.397   4.783   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.063   4.013   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.063   2.473   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.729   1.703   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.938   4.783   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.938   6.323   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.063   7.093   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.729   6.323   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.729   4.783   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.396   4.013   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.396   2.473   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.938   1.703   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.938   0.163   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.736  -2.415   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    9                                                       
CONECT    8    9                                                            
CONECT    9    7    8   26                                                  
CONECT   10   11   26                                                       
CONECT   11   10   12                                                       
CONECT   12   11   15                                                       
CONECT   13   14                                                            
CONECT   14   13   15   21                                                  
CONECT   15   12   14   16                                                  
CONECT   16   15   23                                                       
CONECT   17   18   22                                                       
CONECT   18   17                                                            
CONECT   19   20                                                            
CONECT   20   19   21                                                       
CONECT   21   14   20   22                                                  
CONECT   22   17   21   23                                                  
CONECT   23   16   22   24                                                  
CONECT   24    2   23   25                                                  
CONECT   25    5   24                                                       
CONECT   26    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

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3D PDB for NP0073083 (Myricanone)
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SMILES for NP0073083 (Myricanone)
COC1=C(O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(=O)CCCC2)=C1
Download
INCHI for NP0073083 (Myricanone)
InChI=1S/C21H24O5/c1-25-20-17-12-14(19(24)21(20)26-2)5-3-4-6-15(22)9-7-13-8-10-18(23)16(17)11-13/h8,10-12,23-24H,3-7,9H2,1-2H3
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Synonyms
ValueSource
MyricanoneMeSH
Chemical FormulaC21H24O5
Average Mass356.4123 Da
Monoisotopic Mass356.16237 Da
IUPAC Name3,15-dihydroxy-16,17-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one
Traditional Name3,15-dihydroxy-16,17-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one
CAS Registry NumberNot Available
SMILES
COC1=C(O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(=O)CCCC2)=C1
InChI Identifier
InChI=1S/C21H24O5/c1-25-20-17-12-14(19(24)21(20)26-2)5-3-4-6-15(22)9-7-13-8-10-18(23)16(17)11-13/h8,10-12,23-24H,3-7,9H2,1-2H3
InChI KeyZTSNTUQTNQSIDC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Morella ceriferaLOTUS Database
Morella esculentaLOTUS Database
Morella nanaLOTUS Database
Morella rubraPlant
Myrica galeLOTUS Database
Myrica nagiPlant
Nageia nagiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 6-position.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavones  
Direct Parent6-prenylated flavones  
Alternative Parents
Substituents
  • 6-prenylated flavone
    • 

  • 3-prenylated flavone
    • 

  • Furanoflavone
    • 

  • Furanoflavonoid or dihydroflavonoid
    • 

  • 4'-hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • Hydroxyflavonoid
    • 

  • Furanochromone
    • 

  • Chromone
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Coumaran
    • 

  • Resorcinol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • Pyranone
    • 

  • Monocyclic benzene moiety
    • 

  • Pyran
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Tertiary alcohol
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • 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
logP3.95ALOGPS
logP4.3ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)8.98ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity100.01 m³·mol⁻¹ChemAxon
Polarizability37.67 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0030797  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002737  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71438979  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available