NP-MRD: Showing NP-Card for isoscopariusin O (NP0043161)

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Record Information

Version

2.0

Created at

2021-06-21 00:38:42 UTC

Updated at

2021-06-30 00:18:41 UTC

NP-MRD ID

NP0043161

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isoscopariusin O

Provided By

JEOL Database JEOL Logo

Description

Isoscoparin O 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. isoscopariusin O is found in Isodon scoparius. isoscopariusin O was first documented in 2013 (Zhou, M., et al.). Based on a literature review very few articles have been published on Isoscoparin O.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102383D          

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     RDKit          3D

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  Mrv1652306212102383D          

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    2.2389    1.9946    5.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3340    2.5235    4.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092    0.7975    4.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4828    1.9045    2.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9556    2.7318    2.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1705    0.9013    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4973   -0.2621    2.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802    1.3364    1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5191   -2.0051    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9109   -2.6165    1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8241   -2.6797    0.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026   -0.8214   -1.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590    1.9550   -0.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588    1.5331   -0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7909    1.5981   -4.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875    0.0009   -3.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3826    0.8757   -2.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182    2.8780   -2.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7097    3.9299   -5.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3993   -1.8349   -3.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892   -0.1579   -2.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034   -1.5249   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2278    0.2167    0.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5948   -1.7930    0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558   -2.8089    0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -1.5764   -0.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2177   -0.9990    2.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8242   -2.0349    2.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267   -0.2208    4.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947    0.9831    3.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4177   -1.0638    5.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7048   -1.2344    3.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8551   -2.0430    3.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  3  2  1  0  0  0  0
  2 25  1  0  0  0  0
  9 10  1  0  0  0  0
 14 13  1  0  0  0  0
 13 11  2  0  0  0  0
 11 10  1  0  0  0  0
  6  5  1  0  0  0  0
 11 12  1  0  0  0  0
  6  7  1  0  0  0  0
 14 15  2  0  0  0  0
 25 24  1  0  0  0  0
  2  1  2  3  0  0  0
 24 23  1  0  0  0  0
  7  8  1  6  0  0  0
 23 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21  7  1  0  0  0  0
 14 16  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  1  0  0  0
  7  9  1  0  0  0  0
  6 35  1  6  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  2  0  0  0  0
  4  3  1  0  0  0  0
 18 19  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
 24 56  1  0  0  0  0
 24 57  1  0  0  0  0
 23 54  1  0  0  0  0
 23 55  1  0  0  0  0
 21 50  1  6  0  0  0
  9 39  1  6  0  0  0
 13 45  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
 12 44  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
  8 38  1  0  0  0  0
 22 51  1  0  0  0  0
 22 52  1  0  0  0  0
 22 53  1  0  0  0  0
 16 46  1  0  0  0  0
 26 58  1  0  0  0  0
 26 59  1  0  0  0  0
 26 60  1  0  0  0  0
 19 47  1  0  0  0  0
 19 48  1  0  0  0  0
 19 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043161

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(/C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]1(C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2(C(=C([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O4/c1-14(13-20(24)25)12-19(26-17(4)23)22(6)16(3)10-11-21(5)15(2)8-7-9-18(21)22/h13,16,18-19H,2,7-12H2,1,3-6H3,(H,24,25)/b14-13+/t16-,18+,19+,21+,22+/m1/s1

> <INCHI_KEY>
IGGKHPWWCRUXBE-PXTCAXQFSA-N

> <FORMULA>
C22H34O4

> <MOLECULAR_WEIGHT>
362.51

> <EXACT_MASS>
362.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
41.33574352232327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,5S)-5-[(1S,2R,4aR,8aS)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]-5-(acetyloxy)-3-methylpent-2-enoic acid

> <ALOGPS_LOGP>
5.01

> <JCHEM_LOGP>
4.689899327666666

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.772288783962594

> <JCHEM_PKA_STRONGEST_BASIC>
-7.004518817441152

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
102.58819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,5S)-5-[(1S,2R,4aR,8aS)-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]-5-(acetyloxy)-3-methylpent-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
    1.1777    2.1378    5.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4479    1.3486    4.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0325    1.6229    4.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959    1.7996    2.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9174    0.6333    1.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6038    0.3742    1.9660 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2239   -0.6544    0.9117 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5725   -2.0573    1.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -0.1828   -0.5980 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3692    1.2892   -0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3743    1.6230   -2.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    0.9918   -3.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4381    2.4502   -2.8902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933    2.8342   -4.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9120    2.4366   -5.2719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910    3.7422   -4.4255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4017   -0.3476   -0.9649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942   -1.1852   -1.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698   -1.1697   -2.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060   -1.8624   -2.6242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814   -0.7564    1.1789 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5260   -1.7940    0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1270   -1.0257    2.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5273    0.0195    3.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9864    0.1417    3.4832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3527   -1.1153    4.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7249    2.9654    5.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389    1.9946    5.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3340    2.5235    4.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092    0.7975    4.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4828    1.9045    2.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9556    2.7318    2.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1705    0.9013    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4973   -0.2621    2.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802    1.3364    1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5191   -2.0051    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9109   -2.6165    1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8241   -2.6797    0.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026   -0.8214   -1.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590    1.9550   -0.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588    1.5331   -0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7909    1.5981   -4.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875    0.0009   -3.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3826    0.8757   -2.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182    2.8780   -2.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7097    3.9299   -5.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3993   -1.8349   -3.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892   -0.1579   -2.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034   -1.5249   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2278    0.2167    0.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5948   -1.7930    0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558   -2.8089    0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -1.5764   -0.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2177   -0.9990    2.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8242   -2.0349    2.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267   -0.2208    4.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947    0.9831    3.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4177   -1.0638    5.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7048   -1.2344    3.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8551   -2.0430    3.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  3  2  1  0
  2 25  1  0
  9 10  1  0
 14 13  1  0
 13 11  2  0
 11 10  1  0
  6  5  1  0
 11 12  1  0
  6  7  1  0
 14 15  2  0
 25 24  1  0
  2  1  2  3
 24 23  1  0
  7  8  1  6
 23 21  1  0
 21 22  1  0
 21  7  1  0
 14 16  1  0
  6 25  1  0
 25 26  1  1
  7  9  1  0
  6 35  1  6
  9 17  1  0
 17 18  1  0
 18 20  2  0
  4  3  1  0
 18 19  1  0
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
  5 33  1  0
  5 34  1  0
 24 56  1  0
 24 57  1  0
 23 54  1  0
 23 55  1  0
 21 50  1  6
  9 39  1  6
 13 45  1  0
 10 40  1  0
 10 41  1  0
 12 42  1  0
 12 43  1  0
 12 44  1  0
  1 27  1  0
  1 28  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 16 46  1  0
 26 58  1  0
 26 59  1  0
 26 60  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       1.178   2.138   5.108  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.448   1.349   4.298  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.032   1.623   4.141  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.396   1.800   2.676  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.917   0.633   1.810  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.604   0.374   1.966  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.224  -0.654   0.912  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.573  -2.057   1.028  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.993  -0.183  -0.598  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.369   1.289  -0.895  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.374   1.623  -2.382  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.486   0.992  -3.179  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.438   2.450  -2.890  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.293   2.834  -4.306  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.912   2.437  -5.272  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.691   3.742  -4.426  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.402  -0.348  -0.965  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.694  -1.185  -1.996  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.170  -1.170  -2.253  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.106  -1.862  -2.624  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.781  -0.756   1.179  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.526  -1.794   0.321  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.127  -1.026   2.651  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.527   0.020   3.582  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.986   0.142   3.483  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.353  -1.115   4.129  0.00  0.00           C+0
HETATM   27  H   UNK     0       0.725   2.965   5.648  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.239   1.995   5.276  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.334   2.523   4.690  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.609   0.798   4.574  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.483   1.905   2.578  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.956   2.732   2.299  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.171   0.901   0.784  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.497  -0.262   2.054  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.080   1.336   1.720  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.519  -2.005   1.070  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.911  -2.616   1.899  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.824  -2.680   0.161  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.603  -0.821  -1.242  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.659   1.955  -0.390  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.359   1.533  -0.496  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.791   1.598  -4.035  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.188   0.001  -3.534  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.383   0.876  -2.560  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.318   2.878  -2.238  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.710   3.930  -5.387  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.399  -1.835  -3.091  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.489  -0.158  -2.516  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.703  -1.525  -1.368  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.228   0.217   0.939  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.595  -1.793   0.566  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.156  -2.809   0.495  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.456  -1.576  -0.747  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.218  -0.999   2.776  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.824  -2.035   2.947  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.827  -0.221   4.611  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.995   0.983   3.337  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.418  -1.064   5.224  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.705  -1.234   3.877  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.855  -2.043   3.855  0.00  0.00           H+0
CONECT    1    2   27   28                                                  
CONECT    2    3   25    1                                                  
CONECT    3    2    4   29   30                                             
CONECT    4    5    3   31   32                                             
CONECT    5    4    6   33   34                                             
CONECT    6    5    7   25   35                                             
CONECT    7    6    8   21    9                                             
CONECT    8    7   36   37   38                                             
CONECT    9   10    7   17   39                                             
CONECT   10    9   11   40   41                                             
CONECT   11   13   10   12                                                  
CONECT   12   11   42   43   44                                             
CONECT   13   14   11   45                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   46                                                       
CONECT   17    9   18                                                       
CONECT   18   17   20   19                                                  
CONECT   19   18   47   48   49                                             
CONECT   20   18                                                            
CONECT   21   23   22    7   50                                             
CONECT   22   21   51   52   53                                             
CONECT   23   24   21   54   55                                             
CONECT   24   25   23   56   57                                             
CONECT   25    2   24    6   26                                             
CONECT   26   25   58   59   60                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   16                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  122    0
END

RDKit          3D

60 61  0  0  0  0  0  0  0  0999 V2000
    1.1777    2.1378    5.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4479    1.3486    4.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0325    1.6229    4.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959    1.7996    2.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9174    0.6333    1.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6038    0.3742    1.9660 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2239   -0.6544    0.9117 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5725   -2.0573    1.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -0.1828   -0.5980 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3692    1.2892   -0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3743    1.6230   -2.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    0.9918   -3.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4381    2.4502   -2.8902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933    2.8342   -4.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9120    2.4366   -5.2719 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4017   -0.3476   -0.9649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942   -1.1852   -1.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1698   -1.1697   -2.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060   -1.8624   -2.6242 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814   -0.7564    1.1789 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5260   -1.7940    0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1270   -1.0257    2.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5273    0.0195    3.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9864    0.1417    3.4832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3527   -1.1153    4.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7249    2.9654    5.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389    1.9946    5.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3340    2.5235    4.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092    0.7975    4.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4828    1.9045    2.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9556    2.7318    2.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1705    0.9013    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4973   -0.2621    2.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802    1.3364    1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5191   -2.0051    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9109   -2.6165    1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8241   -2.6797    0.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026   -0.8214   -1.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590    1.9550   -0.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588    1.5331   -0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7909    1.5981   -4.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875    0.0009   -3.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3826    0.8757   -2.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182    2.8780   -2.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7097    3.9299   -5.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3993   -1.8349   -3.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892   -0.1579   -2.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034   -1.5249   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2278    0.2167    0.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5948   -1.7930    0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558   -2.8089    0.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -1.5764   -0.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2177   -0.9990    2.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8242   -2.0349    2.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267   -0.2208    4.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947    0.9831    3.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4177   -1.0638    5.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7048   -1.2344    3.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8551   -2.0430    3.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  3  2  1  0
  2 25  1  0
  9 10  1  0
 14 13  1  0
 13 11  2  0
 11 10  1  0
  6  5  1  0
 11 12  1  0
  6  7  1  0
 14 15  2  0
 25 24  1  0
  2  1  2  3
 24 23  1  0
  7  8  1  6
 23 21  1  0
 21 22  1  0
 21  7  1  0
 14 16  1  0
  6 25  1  0
 25 26  1  1
  7  9  1  0
  6 35  1  6
  9 17  1  0
 17 18  1  0
 18 20  2  0
  4  3  1  0
 18 19  1  0
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
  5 33  1  0
  5 34  1  0
 24 56  1  0
 24 57  1  0
 23 54  1  0
 23 55  1  0
 21 50  1  6
  9 39  1  6
 13 45  1  0
 10 40  1  0
 10 41  1  0
 12 42  1  0
 12 43  1  0
 12 44  1  0
  1 27  1  0
  1 28  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 16 46  1  0
 26 58  1  0
 26 59  1  0
 26 60  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₄

Average Mass

362.5100 Da

Monoisotopic Mass

362.24571 Da

IUPAC Name

(2E,5S)-5-[(1S,2R,4aR,8aS)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]-5-(acetyloxy)-3-methylpent-2-enoic acid

Traditional Name

(2E,5S)-5-[(1S,2R,4aR,8aS)-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]-5-(acetyloxy)-3-methylpent-2-enoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(\[H])=C(/C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]1(C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2(C(=C([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]12[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H34O4/c1-14(13-20(24)25)12-19(26-17(4)23)22(6)16(3)10-11-21(5)15(2)8-7-9-18(21)22/h13,16,18-19H,2,7-12H2,1,3-6H3,(H,24,25)/b14-13+/t16-,18+,19+,21+,22+/m1/s1

InChI Key

IGGKHPWWCRUXBE-PXTCAXQFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isodon scoparius	JEOL database	Zhou, M., et al, Org. Lett.,15 314 (2013)

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
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Fatty acyl
Fatty acid
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.01	ALOGPS
logP	4.69	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.77	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	102.59 m³·mol⁻¹	ChemAxon
Polarizability	41.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71520187

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhou, M., et al. (2013). Zhou, M., et al, Org. Lett.,15 314 (2013). Org. Lett..

Showing NP-Card for isoscopariusin O (NP0043161)

MOL for NP0043161 (isoscopariusin O)

3D MOL for NP0043161 (isoscopariusin O)

3D SDF for NP0043161 (isoscopariusin O)

3D-SDF for NP0043161 (isoscopariusin O)

PDB for NP0043161 (isoscopariusin O)

3D PDB for NP0043161 (isoscopariusin O)

SMILES for NP0043161 (isoscopariusin O)

INCHI for NP0043161 (isoscopariusin O)

Structure for NP0043161 (isoscopariusin O)

3D Structure for NP0043161 (isoscopariusin O)