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Showing NP-Card for 16-O-Methylcafestol (NP0046600)

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Record Information
Version2.0
Created at2022-03-17 20:08:32 UTC
Updated at2022-03-17 20:08:33 UTC
NP-MRD IDNP0046600
Secondary Accession NumbersNone
Natural Product Identification
Common Name16-O-Methylcafestol
Description 16-O-Methylcafestol is found in Coffea arabica and Coffea liberica.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046600 (16-O-Methylcafestol)


  Mrv0541 02241212512D          

 24 28  0  0  1  0            999 V2000
    2.1777    0.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1862   -0.3534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4710    0.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7572   -0.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7587   -1.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4739   -1.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876   -1.1784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9035   -1.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6242   -1.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6766   -0.3605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9075    0.0812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8851    0.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6427    1.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3761    0.9098    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9681    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9741    0.2873    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5645   -0.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6306    0.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3915    0.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7416   -0.0153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3038   -2.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4835   -2.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -1.7340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8633   -0.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 10 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 16 20  1  6  0  0  0
  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
  5 23  1  0  0  0  0
 20 24  1  0  0  0  0
M  END
Download

3D MOL for NP0046600 (16-O-Methylcafestol)

Download
3D SDF for NP0046600 (16-O-Methylcafestol)

  Mrv0541 02241212512D          

 24 28  0  0  1  0            999 V2000
    2.1777    0.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1862   -0.3534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4710    0.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7572   -0.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7587   -1.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4739   -1.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876   -1.1784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9035   -1.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6242   -1.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6766   -0.3605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9075    0.0812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8851    0.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6427    1.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3761    0.9098    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9681    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9741    0.2873    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5645   -0.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6306    0.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3915    0.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7416   -0.0153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3038   -2.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4835   -2.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -1.7340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8633   -0.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 10 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 16 20  1  6  0  0  0
  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
  5 23  1  0  0  0  0
 20 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046600

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@]1(CO)C[C@]23C[C@H]1CC[C@H]2[C@]1(C)CCC2=C(C=CO2)[C@H]1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O3/c1-19-8-6-17-15(7-10-24-17)16(19)5-9-20-11-14(3-4-18(19)20)21(12-20,13-22)23-2/h7,10,14,16,18,22H,3-6,8-9,11-13H2,1-2H3/t14-,16-,18+,19-,20+,21+/m1/s1

> <INCHI_KEY>
BDVVNPOGDNWUOI-GVOJMRIRSA-N

> <FORMULA>
C21H30O3

> <MOLECULAR_WEIGHT>
330.4611

> <EXACT_MASS>
330.219494826

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
38.31128282148644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,4S,12S,13R,16R,17R)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methanol

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
3.3201542879999995

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.358205957739795

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2006155930528615

> <JCHEM_POLAR_SURFACE_AREA>
42.6

> <JCHEM_REFRACTIVITY>
93.3013

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.30e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,4S,12S,13R,16R,17R)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methanol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0046600 (16-O-Methylcafestol)
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PDB for NP0046600 (16-O-Methylcafestol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.065   0.880   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.081  -0.660   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.746   0.108   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.413  -0.664   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.416  -2.204   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.751  -2.972   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.084  -2.200   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.420  -3.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.765  -2.245   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.863  -0.673   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.427   0.152   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.386   1.793   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.800   2.554   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.169   1.698   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.407   0.544   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.285   0.536   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.520  -0.895   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.510   1.469   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.931   0.874   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.718  -0.029   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.434  -4.479   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.903  -4.643   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.274  -3.237   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.945  -1.552   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7   21                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15   17                                             
CONECT   11   10    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14   17   18   20                                             
CONECT   17   16   10                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   16   24                                                       
CONECT   21    6   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    5                                                       
CONECT   24   20                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

Download
3D PDB for NP0046600 (16-O-Methylcafestol)
Download
SMILES for NP0046600 (16-O-Methylcafestol)
CO[C@]1(CO)C[C@]23C[C@H]1CC[C@H]2[C@]1(C)CCC2=C(C=CO2)[C@H]1CC3
Download
INCHI for NP0046600 (16-O-Methylcafestol)
InChI=1S/C21H30O3/c1-19-8-6-17-15(7-10-24-17)16(19)5-9-20-11-14(3-4-18(19)20)21(12-20,13-22)23-2/h7,10,14,16,18,22H,3-6,8-9,11-13H2,1-2H3/t14-,16-,18+,19-,20+,21+/m1/s1
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View in JSmol
Synonyms
ValueSource
16-OMC compoundMeSH
Chemical FormulaC21H30O3
Average Mass330.4611 Da
Monoisotopic Mass330.21949 Da
IUPAC Name[(1S,4S,12S,13R,16R,17R)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methanol
Traditional Name[(1S,4S,12S,13R,16R,17R)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6-dien-17-yl]methanol
CAS Registry NumberNot Available
SMILES
CO[C@]1(CO)C[C@]23C[C@H]1CC[C@H]2[C@]1(C)CCC2=C(C=CO2)[C@H]1CC3
InChI Identifier
InChI=1S/C21H30O3/c1-19-8-6-17-15(7-10-24-17)16(19)5-9-20-11-14(3-4-18(19)20)21(12-20,13-22)23-2/h7,10,14,16,18,22H,3-6,8-9,11-13H2,1-2H3/t14-,16-,18+,19-,20+,21+/m1/s1
InChI KeyBDVVNPOGDNWUOI-GVOJMRIRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Coffea arabicaLOTUS Database
Coffea arabica L.FooDB
Coffea canephoraFooDB
Coffea libericaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon  made up of two fused benzene rings.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassNaphthofurans  
Sub ClassNot Available
Direct ParentNaphthofurans  
Alternative Parents
Substituents
  • Naphthofuran
    • 

  • Benzofuran
    • 

  • Heteroaromatic compound
    • 

  • Furan
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • 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
logP3.64ALOGPS
logP3.32ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)14.36ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area42.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.3 m³·mol⁻¹ChemAxon
Polarizability38.31 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005152  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link16-O-Methylcafestol  
METLIN IDNot Available
PubChem Compound68103163  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available