NP-MRD: Showing NP-Card for 20-acetoxy-19-hydroxyspongia-13(16),14-diene (NP0033780)

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Record Information

Version

2.0

Created at

2021-06-20 17:42:06 UTC

Updated at

2021-06-30 00:03:46 UTC

NP-MRD ID

NP0033780

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20-acetoxy-19-hydroxyspongia-13(16),14-diene

Provided By

JEOL Database JEOL Logo

Description

CHEMBL512825 belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton. 20-acetoxy-19-hydroxyspongia-13(16),14-diene is found in Spongia sp. 20-acetoxy-19-hydroxyspongia-13(16),14-diene was first documented in 2008 (Carroll, A. R., et al.). Based on a literature review very few articles have been published on CHEMBL512825.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119423D          

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     RDKit          3D

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  Mrv1652306202119423D          

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    1.8684    0.5950    2.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6465   -0.0936    0.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6929   -0.3446    2.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2787   -2.3268    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6283   -2.4478    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2923   -1.8451   -1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738   -3.1815   -0.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3609   -2.4799   -1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6690   -0.9381   -2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -0.9900   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163   -2.9333    0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0343   -2.0995    1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2228   -1.6424    1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5864    0.4736   -0.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9693    1.1567    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0058    1.0253   -0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198    3.3430   -0.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792    2.7633   -1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917    4.2497    2.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9514    3.6255    3.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2600    2.5603    2.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6966    5.8454   -0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2586    6.6562    0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7532    4.2494    2.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8479    3.4332    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0629    2.7963    3.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2038    1.7547    2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    2.0124    0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 19  1  0  0  0  0
  8  9  1  0  0  0  0
  8  7  1  0  0  0  0
  9 10  1  0  0  0  0
  6 26  1  0  0  0  0
 14 15  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  1  0  0  0
 16 17  1  0  0  0  0
  6  5  1  1  0  0  0
 26 17  1  0  0  0  0
 10 12  1  1  0  0  0
 10 14  1  0  0  0  0
 10 11  1  0  0  0  0
  6  7  1  0  0  0  0
 14 44  1  6  0  0  0
  6 14  1  0  0  0  0
 26 58  1  6  0  0  0
  5  4  1  0  0  0  0
 26 25  1  0  0  0  0
  4  2  1  0  0  0  0
 17 19  1  0  0  0  0
  2  1  1  0  0  0  0
 23 24  1  0  0  0  0
  2  3  2  0  0  0  0
 24 25  1  0  0  0  0
 12 13  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
  7 32  1  0  0  0  0
  7 33  1  0  0  0  0
 15 45  1  0  0  0  0
 15 46  1  0  0  0  0
 16 47  1  0  0  0  0
 16 48  1  0  0  0  0
 24 54  1  0  0  0  0
 24 55  1  0  0  0  0
 25 56  1  0  0  0  0
 25 57  1  0  0  0  0
 20 52  1  0  0  0  0
 22 53  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 18 51  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 11 38  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
 13 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033780

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])OC(=O)C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])C4=C([H])OC([H])=C4[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O4/c1-15(24)26-14-22-9-4-8-20(2,13-23)18(22)7-10-21(3)17-12-25-11-16(17)5-6-19(21)22/h11-12,18-19,23H,4-10,13-14H2,1-3H3/t18-,19-,20+,21-,22+/m0/s1

> <INCHI_KEY>
SMXDQQCBDPYKBT-BIRZXAFVSA-N

> <FORMULA>
C22H32O4

> <MOLECULAR_WEIGHT>
360.494

> <EXACT_MASS>
360.23005951

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.64221843468193

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,2S,6S,7S,10R)-6-(hydroxymethyl)-6,10-dimethyl-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-11,14-dien-2-yl]methyl acetate

> <ALOGPS_LOGP>
4.39

> <JCHEM_LOGP>
3.6313883356666663

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.59229261395794

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2136693862064978

> <JCHEM_POLAR_SURFACE_AREA>
59.67

> <JCHEM_REFRACTIVITY>
99.72239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2S,6S,7S,10R)-6-(hydroxymethyl)-6,10-dimethyl-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-11,14-dien-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
   -0.2713    1.2791    6.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5860    0.6022    5.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5927   -0.0430    5.2727 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0751    0.8137    3.7738 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8400    0.2376    2.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1950    0.5237    1.3213 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0427   -0.4186    1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -1.8944    0.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2459   -2.1110   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5579   -1.2864   -0.1237 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2521   -1.4250   -1.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5068   -1.9409    0.9107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -1.1751    1.1101 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756    0.2247    0.1170 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3465    1.2304    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8511    2.6716   -0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8533    3.1182    1.0162 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6221    3.3868    2.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869    4.4324    0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7121    5.5683    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450    6.5230   -0.0819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3971    6.0047    0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894    4.7230    0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1549    3.7620    1.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460    2.5271    2.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2946    2.0271    1.1338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2889    2.3561    5.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1461    1.1034    7.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2827    0.8664    6.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722   -0.8338    2.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8684    0.5950    2.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6465   -0.0936    0.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6929   -0.3446    2.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2787   -2.3268    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6283   -2.4478    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2923   -1.8451   -1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738   -3.1815   -0.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3609   -2.4799   -1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6690   -0.9381   -2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -0.9900   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163   -2.9333    0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0343   -2.0995    1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2228   -1.6424    1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5864    0.4736   -0.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9693    1.1567    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0058    1.0253   -0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198    3.3430   -0.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792    2.7633   -1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917    4.2497    2.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9514    3.6255    3.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2600    2.5603    2.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6966    5.8454   -0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2586    6.6562    0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7532    4.2494    2.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8479    3.4332    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0629    2.7963    3.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2038    1.7547    2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    2.0124    0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 19  1  0
  8  9  1  0
  8  7  1  0
  9 10  1  0
  6 26  1  0
 14 15  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 15 16  1  0
 17 18  1  1
 16 17  1  0
  6  5  1  1
 26 17  1  0
 10 12  1  1
 10 14  1  0
 10 11  1  0
  6  7  1  0
 14 44  1  6
  6 14  1  0
 26 58  1  6
  5  4  1  0
 26 25  1  0
  4  2  1  0
 17 19  1  0
  2  1  1  0
 23 24  1  0
  2  3  2  0
 24 25  1  0
 12 13  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
  7 32  1  0
  7 33  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 20 52  1  0
 22 53  1  0
 18 49  1  0
 18 50  1  0
 18 51  1  0
  5 30  1  0
  5 31  1  0
 12 41  1  0
 12 42  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 13 43  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      -0.271   1.279   6.042  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.586   0.602   5.018  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.593  -0.043   5.273  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.075   0.814   3.774  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.840   0.238   2.708  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.195   0.524   1.321  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.043  -0.419   1.170  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.700  -1.894   0.966  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.246  -2.111  -0.208  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.558  -1.286  -0.124  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.252  -1.425  -1.508  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.507  -1.941   0.911  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.683  -1.175   1.110  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.176   0.225   0.117  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.346   1.230   0.082  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.851   2.672  -0.077  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.853   3.118   1.016  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.622   3.387   2.333  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.187   4.432   0.629  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.712   5.568   0.051  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.245   6.523  -0.082  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.397   6.005   0.417  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.189   4.723   0.871  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.155   3.762   1.465  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.446   2.527   2.058  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.295   2.027   1.134  0.00  0.00           C+0
HETATM   27  H   UNK     0      -0.289   2.356   5.857  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.146   1.103   7.038  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.283   0.866   6.010  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.872  -0.834   2.905  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.868   0.595   2.763  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.647  -0.094   0.312  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.693  -0.345   2.050  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.279  -2.327   1.879  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.628  -2.448   0.778  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.292  -1.845  -1.129  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.474  -3.182  -0.291  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.361  -2.480  -1.788  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.669  -0.938  -2.298  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.256  -0.990  -1.514  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.816  -2.933   0.560  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.034  -2.099   1.879  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.223  -1.642   1.771  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.586   0.474  -0.783  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.969   1.157   0.976  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.006   1.025  -0.767  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.720   3.343  -0.100  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.379   2.763  -1.066  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.292   4.250   2.220  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.951   3.626   3.164  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.260   2.560   2.640  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.697   5.845  -0.300  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.259   6.656   0.373  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.753   4.249   2.243  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.848   3.433   0.681  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.063   2.796   3.047  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.204   1.755   2.216  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.765   2.012   0.134  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4   30   31                                             
CONECT    6   26    5    7   14                                             
CONECT    7    8    6   32   33                                             
CONECT    8    9    7   34   35                                             
CONECT    9    8   10   36   37                                             
CONECT   10    9   12   14   11                                             
CONECT   11   10   38   39   40                                             
CONECT   12   10   13   41   42                                             
CONECT   13   12   43                                                       
CONECT   14   15   10   44    6                                             
CONECT   15   14   16   45   46                                             
CONECT   16   15   17   47   48                                             
CONECT   17   18   16   26   19                                             
CONECT   18   17   49   50   51                                             
CONECT   19   23   20   17                                                  
CONECT   20   19   21   52                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   53                                                  
CONECT   23   19   22   24                                                  
CONECT   24   23   25   54   55                                             
CONECT   25   26   24   56   57                                             
CONECT   26    6   17   58   25                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    5                                                            
CONECT   31    5                                                            
CONECT   32    7                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   11                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   16                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   20                                                            
CONECT   53   22                                                            
CONECT   54   24                                                            
CONECT   55   24                                                            
CONECT   56   25                                                            
CONECT   57   25                                                            
CONECT   58   26                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  122    0
END

RDKit          3D

58 61  0  0  0  0  0  0  0  0999 V2000
   -0.2713    1.2791    6.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5860    0.6022    5.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5927   -0.0430    5.2727 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0751    0.8137    3.7738 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8400    0.2376    2.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1950    0.5237    1.3213 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0427   -0.4186    1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -1.8944    0.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2459   -2.1110   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5579   -1.2864   -0.1237 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2521   -1.4250   -1.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5068   -1.9409    0.9107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -1.1751    1.1101 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756    0.2247    0.1170 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3465    1.2304    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8511    2.6716   -0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8533    3.1182    1.0162 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6221    3.3868    2.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1869    4.4324    0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7121    5.5683    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450    6.5230   -0.0819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3971    6.0047    0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894    4.7230    0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1549    3.7620    1.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4460    2.5271    2.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2946    2.0271    1.1338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2889    2.3561    5.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1461    1.1034    7.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2827    0.8664    6.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722   -0.8338    2.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8684    0.5950    2.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6465   -0.0936    0.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6929   -0.3446    2.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2787   -2.3268    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6283   -2.4478    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2923   -1.8451   -1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738   -3.1815   -0.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3609   -2.4799   -1.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6690   -0.9381   -2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -0.9900   -1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8163   -2.9333    0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0343   -2.0995    1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2228   -1.6424    1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5864    0.4736   -0.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9693    1.1567    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0058    1.0253   -0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198    3.3430   -0.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792    2.7633   -1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917    4.2497    2.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9514    3.6255    3.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2600    2.5603    2.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6966    5.8454   -0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2586    6.6562    0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7532    4.2494    2.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8479    3.4332    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0629    2.7963    3.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2038    1.7547    2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    2.0124    0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 19  1  0
  8  9  1  0
  8  7  1  0
  9 10  1  0
  6 26  1  0
 14 15  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 15 16  1  0
 17 18  1  1
 16 17  1  0
  6  5  1  1
 26 17  1  0
 10 12  1  1
 10 14  1  0
 10 11  1  0
  6  7  1  0
 14 44  1  6
  6 14  1  0
 26 58  1  6
  5  4  1  0
 26 25  1  0
  4  2  1  0
 17 19  1  0
  2  1  1  0
 23 24  1  0
  2  3  2  0
 24 25  1  0
 12 13  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
  7 32  1  0
  7 33  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 20 52  1  0
 22 53  1  0
 18 49  1  0
 18 50  1  0
 18 51  1  0
  5 30  1  0
  5 31  1  0
 12 41  1  0
 12 42  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 13 43  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₄

Average Mass

360.4940 Da

Monoisotopic Mass

360.23006 Da

IUPAC Name

[(1S,2S,6S,7S,10R)-6-(hydroxymethyl)-6,10-dimethyl-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-11,14-dien-2-yl]methyl acetate

Traditional Name

[(1S,2S,6S,7S,10R)-6-(hydroxymethyl)-6,10-dimethyl-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-11,14-dien-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])OC(=O)C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])C4=C([H])OC([H])=C4[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]12[H]

InChI Identifier

InChI=1S/C22H32O4/c1-15(24)26-14-22-9-4-8-20(2,13-23)18(22)7-10-21(3)17-12-25-11-16(17)5-6-19(21)22/h11-12,18-19,23H,4-10,13-14H2,1-3H3/t18-,19-,20+,21-,22+/m0/s1

InChI Key

SMXDQQCBDPYKBT-BIRZXAFVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₆D₆, 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
Spongia sp.	JEOL database	Carroll, A. R., et al, J. Nat. Prod. 71, 884 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Isocopalane and spongiane diterpenoids

Alternative Parents

Substituents

Spongiane diterpenoid
Furan
Heteroaromatic compound
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	4.39	ALOGPS
logP	3.63	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	18.59	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.72 m³·mol⁻¹	ChemAxon
Polarizability	40.64 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24716204

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24878743

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Carroll, A. R., et al. (2008). Carroll, A. R., et al, J. Nat. Prod. 71, 884 (2008) . J. Nat. Prod..

Showing NP-Card for 20-acetoxy-19-hydroxyspongia-13(16),14-diene (NP0033780)

MOL for NP0033780 (20-acetoxy-19-hydroxyspongia-13(16),14-diene)

3D MOL for NP0033780 (20-acetoxy-19-hydroxyspongia-13(16),14-diene)

3D SDF for NP0033780 (20-acetoxy-19-hydroxyspongia-13(16),14-diene)

3D-SDF for NP0033780 (20-acetoxy-19-hydroxyspongia-13(16),14-diene)

PDB for NP0033780 (20-acetoxy-19-hydroxyspongia-13(16),14-diene)

3D PDB for NP0033780 (20-acetoxy-19-hydroxyspongia-13(16),14-diene)

SMILES for NP0033780 (20-acetoxy-19-hydroxyspongia-13(16),14-diene)

INCHI for NP0033780 (20-acetoxy-19-hydroxyspongia-13(16),14-diene)

Structure for NP0033780 (20-acetoxy-19-hydroxyspongia-13(16),14-diene)

3D Structure for NP0033780 (20-acetoxy-19-hydroxyspongia-13(16),14-diene)