NP-MRD: Showing NP-Card for 15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid (NP0031856)

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Record Information

Version

2.0

Created at

2021-06-19 22:49:02 UTC

Updated at

2021-06-30 00:00:42 UTC

NP-MRD ID

NP0031856

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid

Provided By

JEOL Database JEOL Logo

Description

CHEMBL481445, also known as 15,16-emc CPD, 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. 15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid is found in Baccharis gaudichaudiana. 15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid was first documented in 2006 (Guo, Y., et al.). Based on a literature review very few articles have been published on CHEMBL481445.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100493D          

 59 61  0  0  0  0            999 V2000
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    4.5978    2.7101    2.9877 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6778    3.0863    1.6129 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9570    1.8072    1.9979 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8139    1.4409    1.0481 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202100493D          

 59 61  0  0  0  0            999 V2000
    5.3428    3.0484    4.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7957    2.7760    5.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2796    2.4846    4.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5815    4.1163    4.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    4.5189    2.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3651    2.9430    0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9514    3.8652    1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872    0.9867    2.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    2.2557    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299    1.3625    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046    0.2055    2.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9030   -0.6638    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4718   -2.0572    0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7652   -2.5234    0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4938   -1.6902    2.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8707    1.6478    0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172    1.1652    2.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6541    1.5817    2.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3039   -0.1051    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    1.1426   -0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044   -0.5744   -0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5338    1.2705   -2.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7668    0.0656   -2.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0738   -2.3794   -2.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6091   -2.9751   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538   -2.3752   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266    0.3766   -6.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5466   -0.7548   -4.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8644   -0.3017   -2.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7524   -2.0210   -2.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3040   -2.4501   -1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3809   -1.2261   -0.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    0.5346   -1.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5057    1.2327    4.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5436    2.6013    3.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 24  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  0  0  0  0
 20 16  2  0  0  0  0
 16 14  1  0  0  0  0
 24 25  1  0  0  0  0
 25  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
 23 22  1  0  0  0  0
 16 17  1  0  0  0  0
 23  8  1  0  0  0  0
 17 18  2  0  0  0  0
 14 13  1  0  0  0  0
 17 19  1  0  0  0  0
 13 12  1  0  0  0  0
  5  6  1  0  0  0  0
 12 10  1  0  0  0  0
 23 57  1  6  0  0  0
 10  8  1  0  0  0  0
  3  2  1  0  0  0  0
 23 14  1  0  0  0  0
 14 15  1  1  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  7  6  1  0  0  0  0
 10 11  1  0  0  0  0
  2  1  1  0  0  0  0
 21 53  1  0  0  0  0
 21 54  1  0  0  0  0
 20 52  1  0  0  0  0
 22 55  1  0  0  0  0
 22 56  1  0  0  0  0
 13 46  1  0  0  0  0
 13 47  1  0  0  0  0
 12 44  1  0  0  0  0
 12 45  1  0  0  0  0
 10 40  1  6  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
  5 32  1  1  0  0  0
 24 58  1  0  0  0  0
 24 59  1  0  0  0  0
  3 29  1  6  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
 19 51  1  0  0  0  0
  6 33  1  0  0  0  0
  6 34  1  0  0  0  0
 15 48  1  0  0  0  0
 15 49  1  0  0  0  0
 15 50  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
 11 41  1  0  0  0  0
 11 42  1  0  0  0  0
 11 43  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031856

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O4/c1-14-8-10-21(3)16(19(22)23)6-5-7-17(21)20(14,2)11-9-15-12-18(24-4)25-13-15/h6,14-15,17-18H,5,7-13H2,1-4H3,(H,22,23)/t14-,15+,17-,18-,20+,21+/m1/s1

> <INCHI_KEY>
AGZLUBWOHWIZBV-WMPOZFHUSA-N

> <FORMULA>
C21H34O4

> <MOLECULAR_WEIGHT>
350.499

> <EXACT_MASS>
350.245709575

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
40.613624950682095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,5S,6R,8aR)-5-{2-[(3S,5R)-5-methoxyoxolan-3-yl]ethyl}-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

> <ALOGPS_LOGP>
5.13

> <JCHEM_LOGP>
4.395921178

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.851608116637617

> <JCHEM_PKA_STRONGEST_BASIC>
-4.005826932261765

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
98.38059999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.27e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,5S,6R,8aR)-5-{2-[(3S,5R)-5-methoxyoxolan-3-yl]ethyl}-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
    5.3428    3.0484    4.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5978    2.7101    2.9877 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3776    3.4441    2.9125 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6778    3.0863    1.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9570    1.8072    1.9979 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8139    1.4409    1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361    0.1205    1.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694   -0.3670    0.5484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4745   -1.7339    1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2561    0.6614    0.6375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8602    0.8261    2.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867    0.3504   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8944    0.2762   -1.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7779   -0.7727   -2.0284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3755   -2.1968   -1.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1659   -0.6517   -3.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0512   -0.3799   -4.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2347   -0.6508   -4.6912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4220    0.2574   -5.6073 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1504   -0.8326   -3.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1663   -1.1466   -2.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5798   -1.3951   -1.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6365   -0.4813   -0.9696 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5290    2.1244    3.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800    3.0562    3.9588 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7957    2.7760    5.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2796    2.4846    4.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5815    4.1163    4.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    4.5189    2.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3651    2.9430    0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9514    3.8652    1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872    0.9867    2.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    2.2557    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299    1.3625    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046    0.2055    2.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9030   -0.6638    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4718   -2.0572    0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7652   -2.5234    0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4938   -1.6902    2.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8707    1.6478    0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172    1.1652    2.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6541    1.5817    2.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3039   -0.1051    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    1.1426   -0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044   -0.5744   -0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5338    1.2705   -2.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7668    0.0656   -2.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0738   -2.3794   -2.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6091   -2.9751   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538   -2.3752   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266    0.3766   -6.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5466   -0.7548   -4.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8644   -0.3017   -2.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7524   -2.0210   -2.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3040   -2.4501   -1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3809   -1.2261   -0.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    0.5346   -1.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5057    1.2327    4.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5436    2.6013    3.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 24  1  0
 21 20  1  0
 21 22  1  0
 20 16  2  0
 16 14  1  0
 24 25  1  0
 25  3  1  0
  3  4  1  0
  4  5  1  0
 23 22  1  0
 16 17  1  0
 23  8  1  0
 17 18  2  0
 14 13  1  0
 17 19  1  0
 13 12  1  0
  5  6  1  0
 12 10  1  0
 23 57  1  6
 10  8  1  0
  3  2  1  0
 23 14  1  0
 14 15  1  1
  8  7  1  1
  8  9  1  0
  7  6  1  0
 10 11  1  0
  2  1  1  0
 21 53  1  0
 21 54  1  0
 20 52  1  0
 22 55  1  0
 22 56  1  0
 13 46  1  0
 13 47  1  0
 12 44  1  0
 12 45  1  0
 10 40  1  6
  7 35  1  0
  7 36  1  0
  5 32  1  1
 24 58  1  0
 24 59  1  0
  3 29  1  6
  4 30  1  0
  4 31  1  0
 19 51  1  0
  6 33  1  0
  6 34  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       5.343   3.048   4.149  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.598   2.710   2.988  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.378   3.444   2.913  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.678   3.086   1.613  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.957   1.807   1.998  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.814   1.441   1.048  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.136   0.121   1.444  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.069  -0.367   0.548  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.474  -1.734   1.155  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.256   0.661   0.638  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.860   0.826   2.039  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.387   0.350  -0.355  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.894   0.276  -1.799  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.778  -0.773  -2.028  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.376  -2.197  -1.954  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.166  -0.652  -3.440  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.051  -0.380  -4.603  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.235  -0.651  -4.691  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.422   0.257  -5.607  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.150  -0.833  -3.674  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.166  -1.147  -2.621  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.580  -1.395  -1.230  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.637  -0.481  -0.970  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.529   2.124   3.423  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.480   3.056   3.959  0.00  0.00           O+0
HETATM   26  H   UNK     0       4.796   2.776   5.056  0.00  0.00           H+0
HETATM   27  H   UNK     0       6.280   2.485   4.130  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.582   4.116   4.157  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.583   4.519   2.971  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.365   2.943   0.774  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.951   3.865   1.351  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.687   0.987   2.019  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.083   2.256   1.034  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.230   1.363   0.038  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.205   0.206   2.482  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.903  -0.664   1.477  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.472  -2.057   0.860  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.765  -2.523   0.890  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.494  -1.690   2.251  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.871   1.648   0.349  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.117   1.165   2.766  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.654   1.582   2.026  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.304  -0.105   2.405  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.145   1.143  -0.298  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.904  -0.574  -0.080  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.534   1.270  -2.097  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.767   0.066  -2.428  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.074  -2.379  -2.780  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.609  -2.975  -2.020  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.954  -2.375  -1.050  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.127   0.377  -6.276  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.547  -0.755  -4.685  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.864  -0.302  -2.568  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.752  -2.021  -2.926  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.304  -2.450  -1.132  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.381  -1.226  -0.505  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.293   0.535  -1.224  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.506   1.233   4.057  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.544   2.601   3.462  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1                                                       
CONECT    3   25    4    2   29                                             
CONECT    4    3    5   30   31                                             
CONECT    5   24    4    6   32                                             
CONECT    6    5    7   33   34                                             
CONECT    7    8    6   35   36                                             
CONECT    8   23   10    7    9                                             
CONECT    9    8   37   38   39                                             
CONECT   10   12    8   11   40                                             
CONECT   11   10   41   42   43                                             
CONECT   12   13   10   44   45                                             
CONECT   13   14   12   46   47                                             
CONECT   14   16   13   23   15                                             
CONECT   15   14   48   49   50                                             
CONECT   16   20   14   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   51                                                       
CONECT   20   21   16   52                                                  
CONECT   21   20   22   53   54                                             
CONECT   22   21   23   55   56                                             
CONECT   23   22    8   57   14                                             
CONECT   24    5   25   58   59                                             
CONECT   25   24    3                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    9                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   15                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   24                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  122    0
END

RDKit          3D

59 61  0  0  0  0  0  0  0  0999 V2000
    5.3428    3.0484    4.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5978    2.7101    2.9877 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3776    3.4441    2.9125 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6778    3.0863    1.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9570    1.8072    1.9979 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8139    1.4409    1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361    0.1205    1.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694   -0.3670    0.5484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4745   -1.7339    1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2561    0.6614    0.6375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8602    0.8261    2.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867    0.3504   -0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8944    0.2762   -1.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7779   -0.7727   -2.0284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3755   -2.1968   -1.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1659   -0.6517   -3.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0512   -0.3799   -4.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2347   -0.6508   -4.6912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4220    0.2574   -5.6073 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1504   -0.8326   -3.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1663   -1.1466   -2.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5798   -1.3951   -1.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6365   -0.4813   -0.9696 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5290    2.1244    3.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800    3.0562    3.9588 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7957    2.7760    5.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2796    2.4846    4.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5815    4.1163    4.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    4.5189    2.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3651    2.9430    0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9514    3.8652    1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872    0.9867    2.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0829    2.2557    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299    1.3625    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046    0.2055    2.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9030   -0.6638    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4718   -2.0572    0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7652   -2.5234    0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4938   -1.6902    2.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8707    1.6478    0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1172    1.1652    2.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6541    1.5817    2.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3039   -0.1051    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    1.1426   -0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044   -0.5744   -0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5338    1.2705   -2.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7668    0.0656   -2.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0738   -2.3794   -2.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6091   -2.9751   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538   -2.3752   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266    0.3766   -6.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5466   -0.7548   -4.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8644   -0.3017   -2.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7524   -2.0210   -2.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3040   -2.4501   -1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3809   -1.2261   -0.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    0.5346   -1.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5057    1.2327    4.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5436    2.6013    3.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 24  1  0
 21 20  1  0
 21 22  1  0
 20 16  2  0
 16 14  1  0
 24 25  1  0
 25  3  1  0
  3  4  1  0
  4  5  1  0
 23 22  1  0
 16 17  1  0
 23  8  1  0
 17 18  2  0
 14 13  1  0
 17 19  1  0
 13 12  1  0
  5  6  1  0
 12 10  1  0
 23 57  1  6
 10  8  1  0
  3  2  1  0
 23 14  1  0
 14 15  1  1
  8  7  1  1
  8  9  1  0
  7  6  1  0
 10 11  1  0
  2  1  1  0
 21 53  1  0
 21 54  1  0
 20 52  1  0
 22 55  1  0
 22 56  1  0
 13 46  1  0
 13 47  1  0
 12 44  1  0
 12 45  1  0
 10 40  1  6
  7 35  1  0
  7 36  1  0
  5 32  1  1
 24 58  1  0
 24 59  1  0
  3 29  1  6
  4 30  1  0
  4 31  1  0
 19 51  1  0
  6 33  1  0
  6 34  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
15,16-EMC CPD	MeSH
15,16-Epoxy-15alpha-methoxy-ent-clerod-3-en-18-Oic acid	MeSH

Chemical Formula

C₂₁H₃₄O₄

Average Mass

350.4990 Da

Monoisotopic Mass

350.24571 Da

IUPAC Name

(4aR,5S,6R,8aR)-5-{2-[(3S,5R)-5-methoxyoxolan-3-yl]ethyl}-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

Traditional Name

(4aR,5S,6R,8aR)-5-{2-[(3S,5R)-5-methoxyoxolan-3-yl]ethyl}-5,6,8a-trimethyl-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])[H])[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])C([H])([H])O[C@@]([H])(OC([H])([H])[H])C1([H])[H]

InChI Identifier

InChI=1S/C21H34O4/c1-14-8-10-21(3)16(19(22)23)6-5-7-17(21)20(14,2)11-9-15-12-18(24-4)25-13-15/h6,14-15,17-18H,5,7-13H2,1-4H3,(H,22,23)/t14-,15+,17-,18-,20+,21+/m1/s1

InChI Key

AGZLUBWOHWIZBV-WMPOZFHUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Baccharis gaudichaudiana	JEOL database	Guo, Y., et al, J. Nat. Prod. 69, 274 (2006)

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
Oxolane
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	5.13	ALOGPS
logP	4.4	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.85	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.38 m³·mol⁻¹	ChemAxon
Polarizability	40.61 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	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

9683358

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11508562

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guo, Y., et al. (2006). Guo, Y., et al, J. Nat. Prod. 69, 274 (2006). J. Nat. Prod..

Showing NP-Card for 15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid (NP0031856)

MOL for NP0031856 (15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid )

3D MOL for NP0031856 (15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid )

3D SDF for NP0031856 (15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid )

3D-SDF for NP0031856 (15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid )

PDB for NP0031856 (15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid )

3D PDB for NP0031856 (15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid )

SMILES for NP0031856 (15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid )

INCHI for NP0031856 (15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid )

Structure for NP0031856 (15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid )

3D Structure for NP0031856 (15,16-epoxy-15alpha-methoxy-ent-clerod-3-en-18-oic acid )