NP-MRD: Showing NP-Card for 4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one (NP0215423)

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Record Information

Version

2.0

Created at

2022-09-05 15:02:47 UTC

Updated at

2022-09-05 15:02:47 UTC

NP-MRD ID

NP0215423

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one

Description

Himbacine 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. 4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one is found in Galbulimima baccata. 4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one was first documented in 2010 (PMID: 20940295). Based on a literature review a significant number of articles have been published on Himbacine (PMID: 34491059) (PMID: 32691184) (PMID: 29860464) (PMID: 28844401) (PMID: 27366081) (PMID: 26932831).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052217022D          

 25 28  0  0  0  0            999 V2000
    1.5983   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -0.4834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  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  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  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
 21 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 25  1  0  0  0  0
  2 25  1  0  0  0  0
  6 25  1  0  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    5.4584   -0.1592    0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9688   -0.1134    0.7057 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4952    1.2854    0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0270    1.9789   -0.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0368    1.1207   -1.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6010   -0.2796   -1.2772 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0918   -0.3150   -1.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3965   -0.2370   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936   -0.2735   -0.1374 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6232    1.0557    0.3971 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8631    1.9380   -0.7960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7900    3.0690   -0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9911    2.7162    0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5241    2.0426    1.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567    0.7606    1.1891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7547   -0.1555    0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1255   -1.5221    0.4007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1196   -2.1453   -0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1289   -2.2310   -1.7084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8452   -2.6040   -1.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1618   -2.7026   -0.0376 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7360   -3.8690    0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6205   -1.4387    0.6652 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1755   -0.9114   -0.1541 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9213   -2.1194   -0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6479    0.1497   -0.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8582   -1.1613    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9554    0.5709    1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9389   -0.6050    1.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370    1.3267    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3699    1.8720    1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9553    2.2912   -0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6076    2.9177   -0.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0078    1.1748   -2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    1.5700   -2.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8761   -0.8838   -2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193   -0.4075   -2.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9740   -0.1444    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4284   -0.4297   -1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8481    1.4855    1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1887    1.3178   -1.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8735    2.3590   -1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3186    3.9685   -0.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2002    3.3937   -1.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6529    2.0147   -0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5113    3.6331    0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7450    2.7092    2.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3869    1.8828    2.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5583    0.2117    2.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7153   -0.2361    0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9005    0.1551   -0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5831   -2.1942    1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0652   -2.7532   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7371   -3.7299    1.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006   -4.7970    0.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8131   -4.0111    0.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753   -1.4074    1.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2519   -2.5811    0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684   -2.7970   -1.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8090   -1.7559   -1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2 24  1  0
 24 25  1  0
  9 23  1  0
 23 21  1  0
 23 17  1  0
 10 15  1  0
 24  6  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 21 53  1  6
 17 52  1  1
 16 50  1  0
 16 51  1  0
 15 49  1  1
 14 47  1  0
 14 48  1  0
 13 45  1  0
 13 46  1  0
 12 43  1  0
 12 44  1  0
 11 41  1  0
 11 42  1  0
 10 40  1  1
  9 39  1  6
  8 38  1  0
  7 37  1  0
  6 36  1  6
  5 34  1  0
  5 35  1  0
  4 32  1  0
  4 33  1  0
  3 30  1  0
  3 31  1  0
  2 29  1  1
  1 26  1  0
  1 27  1  0
  1 28  1  0
 25 58  1  0
 25 59  1  0
 25 60  1  0
 23 57  1  1
M  END


  Mrv1652309052217022D          

 25 28  0  0  0  0            999 V2000
    1.5983   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -0.4834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -6.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  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  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  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
 21 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 14 25  1  0  0  0  0
  2 25  1  0  0  0  0
  6 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215423

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(=O)C2CC3CCCCC3C(\C=C\C3CCCC(C)N3C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H35NO2/c1-14-7-6-9-17(23(14)3)11-12-19-18-10-5-4-8-16(18)13-20-21(19)15(2)25-22(20)24/h11-12,14-21H,4-10,13H2,1-3H3/b12-11+

> <INCHI_KEY>
FMPNFDSPHNUFOS-VAWYXSNFSA-N

> <FORMULA>
C22H35NO2

> <MOLECULAR_WEIGHT>
345.527

> <EXACT_MASS>
345.266779371

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
41.50971496792548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(E)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-dodecahydronaphtho[2,3-c]furan-1-one

> <JCHEM_LOGP>
4.467864856

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.96236309926919

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
102.2695

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(E)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3H-naphtho[2,3-c]furan-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.983  -6.323   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.554  -3.613   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.983  -0.902   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.925  -9.773   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.925 -11.313   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.591 -12.083   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.258 -11.313   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.924 -12.083   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       6.258  -9.773   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       4.924  -9.003   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   17   24                                                  
CONECT   24   23                                                            
CONECT   25   14    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₅NO₂

Average Mass

345.5270 Da

Monoisotopic Mass

345.26678 Da

IUPAC Name

4-[(E)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-dodecahydronaphtho[2,3-c]furan-1-one

Traditional Name

4-[(E)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3H-naphtho[2,3-c]furan-1-one

CAS Registry Number

Not Available

SMILES

CC1OC(=O)C2CC3CCCCC3C(\C=C\C3CCCC(C)N3C)C12

InChI Identifier

InChI=1S/C22H35NO2/c1-14-7-6-9-17(23(14)3)11-12-19-18-10-5-4-8-16(18)13-20-21(19)15(2)25-22(20)24/h11-12,14-21H,4-10,13H2,1-3H3/b12-11+

InChI Key

FMPNFDSPHNUFOS-VAWYXSNFSA-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
Galbulimima baccata	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
Gamma butyrolactone
Piperidine
Tetrahydrofuran
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4.47	ChemAxon
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	102.27 m³·mol⁻¹	ChemAxon
Polarizability	41.51 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00002343

Chemspider ID

4508517

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Himbacine

METLIN ID

Not Available

PubChem Compound

5351501

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chaudhary NK, Taylor WC, Mander LN, Karuso P: Isolation and Structure Elucidation of Additional Alkaloids from the Tropical Rainforest Tree Galbulimima baccata. J Nat Prod. 2021 Sep 24;84(9):2525-2535. doi: 10.1021/acs.jnatprod.1c00537. Epub 2021 Sep 7. [PubMed:34491059 ]
Chen Y, Gao F, Zheng G, Gao S: Enantioselective synthesis of a chiral intermediate of himbacine analogs by Burkholderia cepacia lipase A. Biotechnol Lett. 2020 Dec;42(12):2643-2651. doi: 10.1007/s10529-020-02969-z. Epub 2020 Jul 20. [PubMed:32691184 ]
Carr BJ, Mihara K, Ramachandran R, Saifeddine M, Nathanson NM, Stell WK, Hollenberg MD: Myopia-Inhibiting Concentrations of Muscarinic Receptor Antagonists Block Activation of Alpha2A-Adrenoceptors In Vitro. Invest Ophthalmol Vis Sci. 2018 Jun 1;59(7):2778-2791. doi: 10.1167/iovs.17-22562. [PubMed:29860464 ]
Sugiyama K, Kawanishi S, Oki Y, Kamiya M, Hanada R, Egi M, Akai S: Lipase-catalyzed asymmetric synthesis of naphtho[2,3-c]furan-1(3H)-one derivatives by a one-pot dynamic kinetic resolution/intramolecular Diels-Alder reaction: Total synthesis of (-)-himbacine. Bioorg Med Chem. 2018 Apr 1;26(7):1378-1386. doi: 10.1016/j.bmc.2017.08.019. Epub 2017 Aug 16. [PubMed:28844401 ]
Cheng JW: Impact of selective platelet inhibition in reducing cardiovascular risk - role of vorapaxar. Vasc Health Risk Manag. 2016 Jun 14;12:263-8. doi: 10.2147/VHRM.S81342. eCollection 2016. [PubMed:27366081 ]
Knight E, Robinson E, Smoktunowicz N, Chambers RC, Aliev AE, Inglis GG, Chudasama V, Caddick S: Synthesis of novel and potent vorapaxar analogues. Org Biomol Chem. 2016 Mar 28;14(12):3264-74. doi: 10.1039/c5ob02541a. [PubMed:26932831 ]
Tantry US, Liu F, Chen G, Gurbel PA: Vorapaxar in the secondary prevention of atherothrombosis. Expert Rev Cardiovasc Ther. 2015 Dec;13(12):1293-305. doi: 10.1586/14779072.2015.1109447. Epub 2015 Nov 12. [PubMed:26559689 ]
Riddy DM, Valant C, Rueda P, Charman WN, Sexton PM, Summers RJ, Christopoulos A, Langmead CJ: Label-Free Kinetics: Exploiting Functional Hemi-Equilibrium to Derive Rate Constants for Muscarinic Receptor Antagonists. Mol Pharmacol. 2015 Oct;88(4):779-90. doi: 10.1124/mol.115.100545. Epub 2015 Aug 4. [PubMed:26243731 ]
Authors unspecified: Retraction of "Biomimetic Total Synthesis of Himbacine". Org Lett. 2015 Jun 19;17(12):3190. doi: 10.1021/acs.orglett.5b01596. [PubMed:26087894 ]
Rivas-Ramirez P, Cadaveira-Mosquera A, Lamas JA, Reboreda A: Muscarinic modulation of TREK currents in mouse sympathetic superior cervical ganglion neurons. Eur J Neurosci. 2015 Jul;42(2):1797-807. doi: 10.1111/ejn.12930. Epub 2015 May 19. [PubMed:25899939 ]
Diaz-Ricart M, Escolar G: Vorapaxar for the reduction of atherothrombotic events. Drugs Today (Barc). 2014 Nov;50(11):747-56. doi: 10.1358/dot.2014.50.11.2225852. [PubMed:25525635 ]
Chelliah MV, Eagen K, Guo Z, Chackalamannil S, Xia Y, Tsai H, Greenlee WJ, Ahn HS, Kurowski S, Boykow G, Hsieh Y, Chintala M: Himbacine-derived thrombin receptor antagonists: c7-spirocyclic analogues of vorapaxar. ACS Med Chem Lett. 2014 Mar 11;5(5):561-5. doi: 10.1021/ml500008w. eCollection 2014 May 8. [PubMed:24900880 ]
Chelliah MV, Chackalamannil S, Xia Y, Greenlee WJ, Ahn HS, Kurowski S, Boykow G, Hsieh Y, Chintala M: Himbacine-derived thrombin receptor antagonists: c7-aminomethyl and c9a-hydroxy analogues of vorapaxar. ACS Med Chem Lett. 2013 Dec 18;5(2):183-7. doi: 10.1021/ml400452v. eCollection 2014 Feb 13. [PubMed:24900795 ]
Chen SR, Chen H, Yuan WX, Wess J, Pan HL: Differential regulation of primary afferent input to spinal cord by muscarinic receptor subtypes delineated using knockout mice. J Biol Chem. 2014 May 16;289(20):14321-30. doi: 10.1074/jbc.M114.550384. Epub 2014 Apr 2. [PubMed:24695732 ]
Du W, Guo Y, Yuan W: [Role of muscarinic cholinergic receptor subtypes in regulating glutamatergic synaptic transmission in rat spinal dorsal horn]. Nan Fang Yi Ke Da Xue Xue Bao. 2013 Jun;33(6):838-41. [PubMed:23803193 ]
Chelliah MV, Chackalamannil S, Xia Y, Eagen K, Greenlee WJ, Ahn HS, Agans-Fantuzzi J, Boykow G, Hsieh Y, Bryant M, Chan TM, Chintala M: Discovery of nor-seco himbacine analogs as thrombin receptor antagonists. Bioorg Med Chem Lett. 2012 Apr 1;22(7):2544-9. doi: 10.1016/j.bmcl.2012.01.138. Epub 2012 Feb 16. [PubMed:22405832 ]
White CW, Short JL, Haynes JM, Matsui M, Ventura S: Contractions of the mouse prostate elicited by acetylcholine are mediated by M(3) muscarinic receptors. J Pharmacol Exp Ther. 2011 Dec;339(3):870-7. doi: 10.1124/jpet.111.186841. Epub 2011 Sep 1. [PubMed:21885618 ]
Cao XH, Byun HS, Chen SR, Pan HL: Diabetic neuropathy enhances voltage-activated Ca2+ channel activity and its control by M4 muscarinic receptors in primary sensory neurons. J Neurochem. 2011 Nov;119(3):594-603. doi: 10.1111/j.1471-4159.2011.07456.x. Epub 2011 Sep 21. [PubMed:21883220 ]
Gonzalez JC, Albinana E, Baldelli P, Garcia AG, Hernandez-Guijo JM: Presynaptic muscarinic receptor subtypes involved in the enhancement of spontaneous GABAergic postsynaptic currents in hippocampal neurons. Eur J Neurosci. 2011 Jan;33(1):69-81. doi: 10.1111/j.1460-9568.2010.07475.x. Epub 2010 Nov 23. [PubMed:21091801 ]
Chen SR, Chen H, Yuan WX, Wess J, Pan HL: Dynamic control of glutamatergic synaptic input in the spinal cord by muscarinic receptor subtypes defined using knockout mice. J Biol Chem. 2010 Dec 24;285(52):40427-37. doi: 10.1074/jbc.M110.176966. Epub 2010 Oct 12. [PubMed:20940295 ]
LOTUS database [Link]

Showing NP-Card for 4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one (NP0215423)

MOL for NP0215423 (4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one)

3D MOL for NP0215423 (4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one)

3D SDF for NP0215423 (4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one)

3D-SDF for NP0215423 (4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one)

PDB for NP0215423 (4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one)

3D PDB for NP0215423 (4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one)

SMILES for NP0215423 (4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one)

INCHI for NP0215423 (4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one)

Structure for NP0215423 (4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one)

3D Structure for NP0215423 (4-[(1e)-2-(1,6-dimethylpiperidin-2-yl)ethenyl]-3-methyl-decahydro-3h-naphtho[2,3-c]furan-1-one)