NP-MRD: Showing NP-Card for [(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol (NP0320271)

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Record Information

Version

2.0

Created at

2022-09-11 21:49:40 UTC

Updated at

2022-09-11 21:49:40 UTC

NP-MRD ID

NP0320271

Secondary Accession Numbers

None

Natural Product Identification

Common 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),6,10-trien-17-yl]methanol

Description

16-O-Methylkahweol 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. [(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol is found in Coffea stenophylla. [(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol was first documented in 2018 (PMID: 29329870). Based on a literature review a small amount of articles have been published on 16-O-Methylkahweol (PMID: 32767433) (PMID: 32497844).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112223492D          

 24 28  0  0  1  0            999 V2000
    0.9880    1.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5243    0.7470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8834    0.0043    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1071   -0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0392   -1.0869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6222    0.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3308   -0.0855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7982    0.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6245    0.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0324   -0.1184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8574   -0.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4092    0.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1630    0.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0771   -0.6606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2702   -0.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8579   -1.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0329   -1.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202   -0.8330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2164   -1.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7749   -0.8532    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3535   -1.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4937   -1.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888   -0.8341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7519   -0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  6  0  0  0
  7 24  1  6  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    4.6638    0.3105   -1.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4578   -0.3196   -1.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8446   -0.4173   -0.0547 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7225   -1.1696    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9202   -2.4474    0.3086 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4854   -1.0694   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4816    0.0508   -0.4658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1628   -0.1940   -1.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6456   -0.4331   -1.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2355   -0.5029   -0.4145 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6243   -0.9225   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4172   -1.7471   -1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6049   -1.9356   -0.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5030   -1.2553    0.7426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3599   -0.6317    0.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613    0.2710    1.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5905    0.8063    1.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856    0.6064    0.4456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8790    1.9556   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    0.3250    0.7531 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3062    1.3399    1.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7768    0.9251    1.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573    0.9608    0.4148 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4000    1.2708   -0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0208    0.2986   -2.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6890    1.3676   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4816   -0.1921   -0.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7032   -0.7343    1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2846   -1.3756    1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1768   -2.3132   -0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5149   -1.8225   -0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2038   -1.5824    0.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    0.5734   -2.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2969   -1.1288   -2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229   -1.3593   -2.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1388    0.4051   -2.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6589   -1.4316    0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2281   -2.1998   -2.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4559   -2.5300   -0.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3537    0.4657    2.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295    1.4521    2.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5807    2.7212    0.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3443    1.9418   -1.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9614    2.0843   -0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3551   -0.6374    1.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1728    2.3779    1.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0796    1.2441    2.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3058    1.5662    2.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466   -0.0915    2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2798    1.6977    0.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8012    1.2061   -1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9065    2.2200   -0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  3  6  1  0
  7  6  1  1
  7 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  6
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
 23  3  1  0
 10 18  1  0
 20  7  1  0
 14 15  1  0
  8  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
 24 51  1  0
 24 52  1  0
 23 50  1  1
 22 48  1  0
 22 49  1  0
 21 46  1  0
 21 47  1  0
 20 45  1  1
 19 42  1  0
 19 43  1  0
 19 44  1  0
 17 41  1  0
 16 40  1  0
 12 38  1  0
 13 39  1  0
 10 37  1  1
  9 35  1  0
  9 36  1  0
  8 33  1  0
  8 34  1  0
M  END


  Mrv1652309112223492D          

 24 28  0  0  1  0            999 V2000
    0.9880    1.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5243    0.7470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8834    0.0043    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1071   -0.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0392   -1.0869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6222    0.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3308   -0.0855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7982    0.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6245    0.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0324   -0.1184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8574   -0.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4092    0.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1630    0.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0771   -0.6606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2702   -0.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8579   -1.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0329   -1.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202   -0.8330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2164   -1.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7749   -0.8532    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3535   -1.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4937   -1.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888   -0.8341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7519   -0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  6  0  0  0
  7 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0320271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@]1(CO)C[C@]23C[C@H]1CC[C@H]2[C@]1(C)C=CC2=C(C=CO2)[C@H]1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O3/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/h6-8,10,14,16,18,22H,3-5,9,11-13H2,1-2H3/t14-,16-,18+,19-,20+,21+/m1/s1

> <INCHI_KEY>
OHVRXOLZRGEGJQ-GVOJMRIRSA-N

> <FORMULA>
C21H28O3

> <MOLECULAR_WEIGHT>
328.452

> <EXACT_MASS>
328.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.595092899804

> <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[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6,10-trien-17-yl]methanol

> <JCHEM_LOGP>
3.196840091333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.358205734399508

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7744782844910354

> <JCHEM_POLAR_SURFACE_AREA>
42.6

> <JCHEM_REFRACTIVITY>
94.26389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,4S,12S,13R,16R,17R)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6,10-trien-17-yl]methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       1.844   2.668   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.979   1.394   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.649   0.008   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.200  -0.513   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.073  -2.029   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.028   0.864   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.351  -0.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.223   1.152   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.766   1.130   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.527  -0.221   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.067  -0.220   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.097   0.924   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.504   0.298   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.344  -1.233   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.838  -1.554   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.068  -2.888   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.528  -2.888   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.758  -1.555   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.004  -2.898   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.180  -1.593   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.393  -3.034   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.788  -2.984   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.032  -1.557   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.270  -0.940   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6   23                                             
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   20   24                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    7   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23    7                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₃

Average Mass

328.4520 Da

Monoisotopic Mass

328.20384 Da

IUPAC Name

[(1S,4S,12S,13R,16R,17R)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6,10-trien-17-yl]methanol

Traditional Name

[(1S,4S,12S,13R,16R,17R)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6,10-trien-17-yl]methanol

CAS Registry Number

Not Available

SMILES

CO[C@]1(CO)C[C@]23C[C@H]1CC[C@H]2[C@]1(C)C=CC2=C(C=CO2)[C@H]1CC3

InChI Identifier

InChI=1S/C21H28O3/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/h6-8,10,14,16,18,22H,3-5,9,11-13H2,1-2H3/t14-,16-,18+,19-,20+,21+/m1/s1

InChI Key

OHVRXOLZRGEGJQ-GVOJMRIRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coffea stenophylla	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Heteroaromatic compound
Furan
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.2	ChemAxon
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	42.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.26 m³·mol⁻¹	ChemAxon
Polarizability	37.6 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68103165

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guercia E, Colomban S, Navarini L: 16-O-Methylated diterpenes in green Coffea arabica: ultra-high-performance liquid chromatography-tandem mass spectrometry method optimization and validation. J Mass Spectrom. 2020 Nov;55(11):e4636. doi: 10.1002/jms.4636. Epub 2020 Aug 6. [PubMed:32767433 ]
Portaluri V, Thomas F, Guyader S, Jamin E, Bertrand B, Remaud GS, Schievano E, Mammi S, Guercia E, Navarini L: Limited genotypic and geographic variability of 16-O-methylated diterpene content in Coffea arabica green beans. Food Chem. 2020 Nov 1;329:127129. doi: 10.1016/j.foodchem.2020.127129. Epub 2020 May 27. [PubMed:32497844 ]
Gunning Y, Defernez M, Watson AD, Beadman N, Colquhoun IJ, Le Gall G, Philo M, Garwood H, Williamson D, Davis AP, Kemsley EK: 16-O-methylcafestol is present in ground roast Arabica coffees: Implications for authenticity testing. Food Chem. 2018 May 15;248:52-60. doi: 10.1016/j.foodchem.2017.12.034. Epub 2017 Dec 11. [PubMed:29329870 ]
LOTUS database [Link]

Showing NP-Card for [(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol (NP0320271)

MOL for NP0320271 ([(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol)

3D MOL for NP0320271 ([(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol)

3D SDF for NP0320271 ([(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol)

3D-SDF for NP0320271 ([(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol)

PDB for NP0320271 ([(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol)

3D PDB for NP0320271 ([(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol)

SMILES for NP0320271 ([(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol)

INCHI for NP0320271 ([(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol)

Structure for NP0320271 ([(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol)

3D Structure for NP0320271 ([(1s,4s,12s,13r,16r,17r)-17-methoxy-12-methyl-8-oxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁵,⁹]nonadeca-5(9),6,10-trien-17-yl]methanol)