NP-MRD: Showing NP-Card for (4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid (NP0154964)

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Record Information

Version

2.0

Created at

2022-09-02 11:57:01 UTC

Updated at

2022-09-02 11:57:01 UTC

NP-MRD ID

NP0154964

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid

Description

Vouacapan belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid is found in Pterodon emarginatus. (4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid was first documented in 2018 (PMID: 29723629). Based on a literature review a small amount of articles have been published on Vouacapan (PMID: 34994338) (PMID: 33142344) (PMID: 32962444) (PMID: 30798128).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022213572D          

 25 28  0  0  1  0            999 V2000
   -0.6302   -2.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807   -3.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -2.2077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0584   -1.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -2.3529    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705   -1.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -1.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -1.3611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -1.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -2.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -2.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -3.2741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7114   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1796   -4.6807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5235   -4.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -3.1289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0872   -3.7596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3675   -4.5355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -3.6143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7433   -4.2451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -2.8384    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 20 16  1  6  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 25 23  1  1  0  0  0
  2 25  1  0  0  0  0
  7 25  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.4347    1.7863    0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8821    0.3528    0.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4608   -0.3903   -0.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470   -0.3270    1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3397   -0.5909    2.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -0.8097    2.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6297   -0.6824    0.6601 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9984   -1.9904    0.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8410   -0.4943    0.5243 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5908   -1.8365    0.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357   -1.5505    0.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0633   -2.3599    0.5218 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2045   -1.7205    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9203   -0.4191   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5506   -0.3166    0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6925    0.8635   -0.2768 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2173    1.7399   -1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4965    2.9522   -1.0994 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4255    1.2500   -2.5964 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149    0.2948   -0.6243 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4464    1.4192   -1.0615 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9250    1.9892   -2.2095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9541    0.8184   -1.2555 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7956    1.6571   -1.9319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3985    0.4793    0.1407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9112    1.9821   -0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2143    1.9268    0.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6635    2.5340    0.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6921   -0.7663   -1.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0945   -1.2596   -0.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1460    0.2390   -1.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1559    0.3252    1.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9123   -1.2759    1.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3694    0.2314    3.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6814   -1.4943    3.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2378   -0.0981    2.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5573   -1.8261    2.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0451   -2.2715    0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6803   -2.0566   -1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4109   -2.7831    0.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355   -0.0068    1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3015   -2.3786   -0.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245   -2.4334    1.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2145   -2.1121    0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6440    0.3373   -0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6181    1.4253    0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3642    1.3603   -2.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841   -0.3851   -1.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3476    2.1448   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7203    2.9753   -2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7559   -0.1533   -1.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2483    2.3399   -2.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148    1.3649    0.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 15  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 15 16  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 16 17  1  0
 17 19  1  0
 17 18  2  0
 25  2  1  0
 25  7  1  0
 20  9  1  0
 12 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  1
 10 42  1  0
 10 43  1  0
 14 45  1  0
 13 44  1  0
 16 46  1  1
 20 48  1  6
 21 49  1  1
 22 50  1  0
 23 51  1  6
 24 52  1  0
 25 53  1  1
 19 47  1  0
M  END


  Mrv1652309022213572D          

 25 28  0  0  1  0            999 V2000
   -0.6302   -2.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807   -3.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -2.2077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0584   -1.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -2.3529    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705   -1.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -1.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -1.3611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -1.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -2.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -2.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -3.2741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7114   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1796   -4.6807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5235   -4.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -3.1289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0872   -3.7596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3675   -4.5355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -3.6143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7433   -4.2451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -2.8384    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 20 16  1  6  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 25 23  1  1  0  0  0
  2 25  1  0  0  0  0
  7 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154964

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@]2(C)[C@H]3CC4=C(C=CO4)[C@H]([C@@H]3[C@@H](O)[C@H](O)[C@@H]12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O5/c1-19(2)6-4-7-20(3)11-9-12-10(5-8-25-12)13(18(23)24)14(11)15(21)16(22)17(19)20/h5,8,11,13-17,21-22H,4,6-7,9H2,1-3H3,(H,23,24)/t11-,13+,14+,15+,16-,17-,20+/m0/s1

> <INCHI_KEY>
GHQBUKANOGSFQS-WENPLGDPSA-N

> <FORMULA>
C20H28O5

> <MOLECULAR_WEIGHT>
348.439

> <EXACT_MASS>
348.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.089437839299016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,7S,8R,9R,10R,11S)-8,9-dihydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylic acid

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.1328816216666664

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.625611065033922

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.714435360296638

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8237506636039447

> <JCHEM_POLAR_SURFACE_AREA>
90.9

> <JCHEM_REFRACTIVITY>
91.6948

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,7S,8R,9R,10R,11S)-8,9-dihydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.176  -5.291   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.341  -5.027   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.337  -6.567   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.182  -3.579   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.810  -2.402   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.326  -2.673   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.850  -4.121   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.842  -2.944   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.366  -4.392   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.358  -3.215   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.874  -3.486   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.090  -2.541   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.365  -3.405   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.937  -4.884   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.398  -4.934   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.405  -6.112   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.928  -7.560   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.935  -8.737   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.444  -7.831   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.889  -5.841   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.896  -7.018   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.419  -8.466   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.380  -6.747   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.387  -7.924   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.857  -5.298   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   25                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   25                                             
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11                                                       
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   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16    9   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
6-alpha-7beta-Dihydroxyvouacapan-17-beta-Oate	MeSH

Chemical Formula

C₂₀H₂₈O₅

Average Mass

348.4390 Da

Monoisotopic Mass

348.19367 Da

IUPAC Name

(1S,2R,7S,8R,9R,10R,11S)-8,9-dihydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylic acid

Traditional Name

(1S,2R,7S,8R,9R,10R,11S)-8,9-dihydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]2(C)[C@H]3CC4=C(C=CO4)[C@H]([C@@H]3[C@@H](O)[C@H](O)[C@@H]12)C(O)=O

InChI Identifier

InChI=1S/C20H28O5/c1-19(2)6-4-7-20(3)11-9-12-10(5-8-25-12)13(18(23)24)14(11)15(21)16(22)17(19)20/h5,8,11,13-17,21-22H,4,6-7,9H2,1-3H3,(H,23,24)/t11-,13+,14+,15+,16-,17-,20+/m0/s1

InChI Key

GHQBUKANOGSFQS-WENPLGDPSA-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
Pterodon emarginatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Naphthofuran
Benzofuran
Cyclic alcohol
Heteroaromatic compound
Furan
1,2-diol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
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	2.4	ALOGPS
logP	2.13	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.71	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.69 m³·mol⁻¹	ChemAxon
Polarizability	38.09 Å³	ChemAxon
Number of Rings	4	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

142619

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ortiz-Zamora L, Ferreira JV, de Oliveira NKS, de Molfetta FA, Hage-Melim LIS, Fernandes CP, Oliveira AEMFM: Potential Implications of Vouacapan Compounds for Insecticidal Activity: An In Silico Study. Recent Pat Biotechnol. 2022;16(2):155-173. doi: 10.2174/1872208316666220106110902. [PubMed:34994338 ]
Basting RT, de Oliveira Sousa IM, Butterweck V, Foglio MA: Antiproliferative Effects of Pterodon pubescens Extract and Isolated Diterpenes in HaCaT Cells. Planta Med. 2021 Mar;87(3):218-224. doi: 10.1055/a-1279-0645. Epub 2020 Nov 3. [PubMed:33142344 ]
Souza VHDS, Basting RT, Sousa IMO, Queiroz NCA, Carvalho JE, Foglio MA: Evaluation of non-clinical toxicity of extract and vouacapans from fruits of Pterodon pubescens Benth. Drug Chem Toxicol. 2022 May;45(3):1325-1338. doi: 10.1080/01480545.2020.1822858. Epub 2020 Sep 23. [PubMed:32962444 ]
Basting RT, Spindola HM, Sousa IMO, Queiroz NCA, Trigo JR, de Carvalho JE, Foglio MA: Pterodon pubescens and Cordia verbenacea association promotes a synergistic response in antinociceptive model and improves the anti-inflammatory results in animal models. Biomed Pharmacother. 2019 Apr;112:108693. doi: 10.1016/j.biopha.2019.108693. Epub 2019 Feb 21. [PubMed:30798128 ]
Dos Santos CBR, da Silva Ramos R, Ortiz BLS, da Silva GM, Giuliatti S, Balderas-Lopez JL, Navarrete A, Carvalho JCT: Oil from the fruits of Pterodon emarginatus Vog.: A traditional anti-inflammatory. Study combining in vivo and in silico. J Ethnopharmacol. 2018 Aug 10;222:107-120. doi: 10.1016/j.jep.2018.04.041. Epub 2018 Apr 30. [PubMed:29723629 ]
LOTUS database [Link]

Showing NP-Card for (4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid (NP0154964)

MOL for NP0154964 ((4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid)

3D MOL for NP0154964 ((4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid)

3D SDF for NP0154964 ((4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid)

3D-SDF for NP0154964 ((4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid)

PDB for NP0154964 ((4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid)

3D PDB for NP0154964 ((4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid)

SMILES for NP0154964 ((4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid)

INCHI for NP0154964 ((4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid)

Structure for NP0154964 ((4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid)

3D Structure for NP0154964 ((4as,5r,6r,6ar,7s,11as,11br)-5,6-dihydroxy-4,4,11b-trimethyl-1h,2h,3h,4ah,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-7-carboxylic acid)