NP-MRD: Showing NP-Card for Divinatorin C (NP0026573)

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Record Information

Version

2.0

Created at

2021-06-19 18:25:19 UTC

Updated at

2021-06-29 23:52:11 UTC

NP-MRD ID

NP0026573

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Divinatorin C

Provided By

JEOL Database JEOL Logo

Description

Divinatorin C is found in Salvia divinorum. Divinatorin C was first documented in 2003 (Bigham, A. K., et al.). Based on a literature review very few articles have been published on Divinatorin C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120253D          

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   -1.8614    4.8965    0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6523    4.6129   -1.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538    3.0156   -1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7913    3.2296   -2.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2686    7.5922   -0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7058    4.8440   -1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7525    2.5989   -2.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0638    2.4244   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5638    0.7157   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6215    1.6275   -2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7760    2.3084    0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1626    0.2761   -1.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5606    1.1362   -1.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -0.4882   -0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4396   -0.7590    0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7523   -1.0374    1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5936    0.5006    2.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.5487    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2696   -1.8472    4.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9398   -4.0487    4.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3080   -1.9100    1.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  1  0  0  0
 15 11  2  0  0  0  0
 21 22  1  0  0  0  0
 11  9  1  0  0  0  0
 22 23  1  0  0  0  0
 23 27  2  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  0  0  0  0
  9  8  1  0  0  0  0
  8  7  1  0  0  0  0
 27 26  1  0  0  0  0
 26 25  1  0  0  0  0
 25 24  2  0  0  0  0
 24 23  1  0  0  0  0
  7  6  1  0  0  0  0
  9 10  1  6  0  0  0
  6 19  1  0  0  0  0
  6  5  1  0  0  0  0
 18  9  1  0  0  0  0
 19 20  1  0  0  0  0
 11 12  1  0  0  0  0
  6 33  1  1  0  0  0
 18 47  1  1  0  0  0
 12 14  1  0  0  0  0
  5  4  1  0  0  0  0
 16 15  1  0  0  0  0
  4  2  1  0  0  0  0
 12 13  2  0  0  0  0
  2  1  1  0  0  0  0
 16 17  1  0  0  0  0
  2  3  2  0  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 15 42  1  0  0  0  0
 17 45  1  0  0  0  0
 17 46  1  0  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
 14 41  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
 22 53  1  0  0  0  0
 22 54  1  0  0  0  0
 27 57  1  0  0  0  0
 25 56  1  0  0  0  0
 24 55  1  0  0  0  0
 10 38  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
  5 31  1  0  0  0  0
  5 32  1  0  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
 20 50  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026573

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])([H])C([H])([H])[C@@]2([H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])OC(=O)C([H])([H])[H])[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])C1=C([H])OC([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-15(23)27-14-17-8-11-22(3)18(20(24)25)5-4-6-19(22)21(17,2)10-7-16-9-12-26-13-16/h5,9,12-13,17,19H,4,6-8,10-11,14H2,1-3H3,(H,24,25)/t17-,19+,21-,22-/m0/s1

> <INCHI_KEY>
CSQRHRPGMJMXPY-TZEULACYSA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.477

> <EXACT_MASS>
374.209324066

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.31081524083729

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,5R,6R,8aR)-6-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,8a-dimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

> <ALOGPS_LOGP>
4.53

> <JCHEM_LOGP>
4.159713603333333

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.167112848469646

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7841228429356955

> <JCHEM_POLAR_SURFACE_AREA>
76.74000000000001

> <JCHEM_REFRACTIVITY>
102.07979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,5R,6R,8aR)-6-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -3.5963    1.3551    5.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443    0.7741    4.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8189    0.1154    4.5207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680    1.0961    3.2517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8451    0.5954    2.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7337    1.5559    1.5700 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3596    2.9230    1.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3217    3.9636    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4693    3.5453   -0.4011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3328    3.5894   -1.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6926    4.5299   -0.6477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4634    5.9910   -0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6005    6.5719   -0.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5791    6.6675   -0.1618 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    4.1204   -1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2928    2.6932   -1.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1323    1.7027   -1.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1482    2.1257   -0.0726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8489    0.9900    0.3971 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7402    0.4642   -0.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466   -0.2767    0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0129   -0.0516    1.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -1.3424    2.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0959   -2.0925    3.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9023   -3.2019    3.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376   -3.1886    2.7157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298   -2.0604    1.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6128    2.4450    5.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951    1.0799    6.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6129    0.9546    5.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6390    0.5185    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4852   -0.4215    2.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0764    1.7519    2.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8846    3.3121    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1242    2.8179    0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655    4.1642    1.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8614    4.8965    0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6523    4.6129   -1.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538    3.0156   -1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7913    3.2296   -2.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2686    7.5922   -0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7058    4.8440   -1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7525    2.5989   -2.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0638    2.4244   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5638    0.7157   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6215    1.6275   -2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7760    2.3084    0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1626    0.2761   -1.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5606    1.1362   -1.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -0.4882   -0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4396   -0.7590    0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7523   -1.0374    1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5936    0.5006    2.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.5487    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2696   -1.8472    4.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9398   -4.0487    4.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3080   -1.9100    1.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  1
 15 11  2  0
 21 22  1  0
 11  9  1  0
 22 23  1  0
 23 27  2  0
 18 17  1  0
 18 19  1  0
  9  8  1  0
  8  7  1  0
 27 26  1  0
 26 25  1  0
 25 24  2  0
 24 23  1  0
  7  6  1  0
  9 10  1  6
  6 19  1  0
  6  5  1  0
 18  9  1  0
 19 20  1  0
 11 12  1  0
  6 33  1  1
 18 47  1  1
 12 14  1  0
  5  4  1  0
 16 15  1  0
  4  2  1  0
 12 13  2  0
  2  1  1  0
 16 17  1  0
  2  3  2  0
 16 43  1  0
 16 44  1  0
 15 42  1  0
 17 45  1  0
 17 46  1  0
  8 36  1  0
  8 37  1  0
  7 34  1  0
  7 35  1  0
 14 41  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 27 57  1  0
 25 56  1  0
 24 55  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
  5 31  1  0
  5 32  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.596   1.355   5.576  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.844   0.774   4.418  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.819   0.115   4.521  0.00  0.00           O+0
HETATM    4  O   UNK     0      -3.468   1.096   3.252  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.845   0.595   2.054  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.734   1.556   1.570  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.360   2.923   1.235  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.322   3.964   0.821  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.469   3.545  -0.401  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.333   3.589  -1.683  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.693   4.530  -0.648  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.463   5.991  -0.489  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.601   6.572  -0.600  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.579   6.668  -0.162  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.912   4.120  -1.055  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.293   2.693  -1.296  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.132   1.703  -1.184  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.148   2.126  -0.073  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.849   0.990   0.397  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.740   0.464  -0.755  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.047  -0.277   0.894  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.013  -0.052   1.984  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.564  -1.342   2.494  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.096  -2.092   3.609  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.902  -3.202   3.699  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.838  -3.189   2.716  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.630  -2.060   1.990  0.00  0.00           C+0
HETATM   28  H   UNK     0      -3.613   2.445   5.497  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.095   1.080   6.509  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.613   0.955   5.597  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.639   0.519   1.303  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.485  -0.422   2.232  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.076   1.752   2.426  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.885   3.312   2.117  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.124   2.818   0.458  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.666   4.164   1.679  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.861   4.896   0.624  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.652   4.613  -1.913  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.254   3.016  -1.603  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.791   3.230  -2.563  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.269   7.592  -0.078  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.706   4.844  -1.234  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.753   2.599  -2.287  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.064   2.424  -0.563  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.564   0.716  -0.996  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.622   1.628  -2.150  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.776   2.308   0.815  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.163   0.276  -1.665  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.561   1.136  -1.003  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.213  -0.488  -0.485  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.440  -0.759   0.035  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.752  -1.037   1.250  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.594   0.501   2.830  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.841   0.549   1.592  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.270  -1.847   4.264  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.940  -4.049   4.370  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.308  -1.910   1.162  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4   31   32                                             
CONECT    6    7   19    5   33                                             
CONECT    7    8    6   34   35                                             
CONECT    8    9    7   36   37                                             
CONECT    9   11    8   10   18                                             
CONECT   10    9   38   39   40                                             
CONECT   11   15    9   12                                                  
CONECT   12   11   14   13                                                  
CONECT   13   12                                                            
CONECT   14   12   41                                                       
CONECT   15   11   16   42                                                  
CONECT   16   15   17   43   44                                             
CONECT   17   18   16   45   46                                             
CONECT   18   17   19    9   47                                             
CONECT   19   21   18    6   20                                             
CONECT   20   19   48   49   50                                             
CONECT   21   19   22   51   52                                             
CONECT   22   21   23   53   54                                             
CONECT   23   22   27   24                                                  
CONECT   24   25   23   55                                                  
CONECT   25   26   24   56                                                  
CONECT   26   27   25                                                       
CONECT   27   23   26   57                                                  
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    5                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38   10                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   17                                                            
CONECT   47   18                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   22                                                            
CONECT   54   22                                                            
CONECT   55   24                                                            
CONECT   56   25                                                            
CONECT   57   27                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

RDKit          3D

57 59  0  0  0  0  0  0  0  0999 V2000
   -3.5963    1.3551    5.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443    0.7741    4.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8189    0.1154    4.5207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680    1.0961    3.2517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8451    0.5954    2.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7337    1.5559    1.5700 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3596    2.9230    1.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3217    3.9636    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4693    3.5453   -0.4011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3328    3.5894   -1.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6926    4.5299   -0.6477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4634    5.9910   -0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6005    6.5719   -0.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5791    6.6675   -0.1618 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    4.1204   -1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2928    2.6932   -1.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1323    1.7027   -1.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1482    2.1257   -0.0726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8489    0.9900    0.3971 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7402    0.4642   -0.7548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466   -0.2767    0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0129   -0.0516    1.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -1.3424    2.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0959   -2.0925    3.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9023   -3.2019    3.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376   -3.1886    2.7157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298   -2.0604    1.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6128    2.4450    5.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951    1.0799    6.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6129    0.9546    5.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6390    0.5185    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4852   -0.4215    2.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0764    1.7519    2.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8846    3.3121    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1242    2.8179    0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6655    4.1642    1.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8614    4.8965    0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6523    4.6129   -1.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538    3.0156   -1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7913    3.2296   -2.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2686    7.5922   -0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7058    4.8440   -1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7525    2.5989   -2.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0638    2.4244   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5638    0.7157   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6215    1.6275   -2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7760    2.3084    0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1626    0.2761   -1.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5606    1.1362   -1.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -0.4882   -0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4396   -0.7590    0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7523   -1.0374    1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5936    0.5006    2.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.5487    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2696   -1.8472    4.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9398   -4.0487    4.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3080   -1.9100    1.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  1
 15 11  2  0
 21 22  1  0
 11  9  1  0
 22 23  1  0
 23 27  2  0
 18 17  1  0
 18 19  1  0
  9  8  1  0
  8  7  1  0
 27 26  1  0
 26 25  1  0
 25 24  2  0
 24 23  1  0
  7  6  1  0
  9 10  1  6
  6 19  1  0
  6  5  1  0
 18  9  1  0
 19 20  1  0
 11 12  1  0
  6 33  1  1
 18 47  1  1
 12 14  1  0
  5  4  1  0
 16 15  1  0
  4  2  1  0
 12 13  2  0
  2  1  1  0
 16 17  1  0
  2  3  2  0
 16 43  1  0
 16 44  1  0
 15 42  1  0
 17 45  1  0
 17 46  1  0
  8 36  1  0
  8 37  1  0
  7 34  1  0
  7 35  1  0
 14 41  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 27 57  1  0
 25 56  1  0
 24 55  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
  5 31  1  0
  5 32  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₅

Average Mass

374.4770 Da

Monoisotopic Mass

374.20932 Da

IUPAC Name

(4aR,5R,6R,8aR)-6-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,8a-dimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

Traditional Name

(4aR,5R,6R,8aR)-6-[(acetyloxy)methyl]-5-[2-(furan-3-yl)ethyl]-5,8a-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])C([H])([H])C([H])([H])[C@@]2([H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])OC(=O)C([H])([H])[H])[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])C1=C([H])OC([H])=C1[H]

InChI Identifier

InChI=1S/C22H30O5/c1-15(23)27-14-17-8-11-22(3)18(20(24)25)5-4-6-19(22)21(17,2)10-7-16-9-12-26-13-16/h5,9,12-13,17,19H,4,6-8,10-11,14H2,1-3H3,(H,24,25)/t17-,19+,21-,22-/m0/s1

InChI Key

CSQRHRPGMJMXPY-TZEULACYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Salvia divinorum	JEOL database	Bigham, A. K., et al, J. Nat. Prod. 66, 1242 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Dicarboxylic acid or derivatives
Heteroaromatic compound
Furan
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.53	ALOGPS
logP	4.16	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.74 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	102.08 m³·mol⁻¹	ChemAxon
Polarizability	41.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

9958361

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11783681

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bigham, A. K., et al. (2003). Bigham, A. K., et al, J. Nat. Prod. 66, 1242 (2003). J. Nat. Prod..

Showing NP-Card for Divinatorin C (NP0026573)

MOL for NP0026573 (Divinatorin C)

3D MOL for NP0026573 (Divinatorin C)

3D SDF for NP0026573 (Divinatorin C)

3D-SDF for NP0026573 (Divinatorin C)

PDB for NP0026573 (Divinatorin C)

3D PDB for NP0026573 (Divinatorin C)

SMILES for NP0026573 (Divinatorin C)

INCHI for NP0026573 (Divinatorin C)

Structure for NP0026573 (Divinatorin C)

3D Structure for NP0026573 (Divinatorin C)