NP-MRD: Showing NP-Card for acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+ (NP0037980)

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Record Information

Version

2.0

Created at

2021-06-20 20:47:00 UTC

Updated at

2021-06-30 00:10:30 UTC

NP-MRD ID

NP0037980

Secondary Accession Numbers

None

Natural Product Identification

Common Name

acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+

Provided By

JEOL Database JEOL Logo

Description

(1R)-1,2-(Methyleneoxycarbonyl)-4alpha,9beta-diacetoxy-4balpha,8,8,10aalpha-tetramethyl-1,4,4abeta,4b,5,6,7,8,8abeta,9,10,10a-dodecahydrophenanthrene-1beta-ol belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+ is found in Dysidea cf. arenaria. acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+ was first documented in 2009 (Agena, M., et al.). Based on a literature review very few articles have been published on (1R)-1,2-(Methyleneoxycarbonyl)-4alpha,9beta-diacetoxy-4balpha,8,8,10aalpha-tetramethyl-1,4,4abeta,4b,5,6,7,8,8abeta,9,10,10a-dodecahydrophenanthrene-1beta-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122473D          

 65 68  0  0  0  0            999 V2000
    0.1247   -0.6130   -5.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757    0.0120   -4.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2080    1.0573   -4.3420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3994   -0.7534   -3.1766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -0.2710   -1.9620 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4742   -0.7339   -1.9985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3128   -0.4096   -0.7380 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6551    1.0989   -0.7567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5104   -0.8367    0.5611 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3572   -0.7004    1.8903 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2841    0.6296    2.4194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2002    0.7478    3.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1264    2.1951    4.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1798   -0.1760    4.5722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8273   -0.9872    1.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3690   -1.2289    0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7999   -1.4286    0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6826   -1.6112    1.0477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9494   -1.4066   -1.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7414   -0.9050   -1.7334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6280   -1.2775   -0.7638 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2754   -2.6594   -0.9685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906   -0.3530    0.6207 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8394    1.1806    0.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3192   -1.0496    1.8410 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1998   -0.9295    1.8793 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8332   -1.4486    0.6012 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2988   -0.7930   -0.7002 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9196   -1.6264   -1.8541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8587    0.6338   -0.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2838   -0.8625   -0.7106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2361   -1.6344   -5.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0939   -0.0375   -6.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -0.6063   -5.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9487    0.8200   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9731   -0.3231   -2.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559   -1.8163   -2.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1840    1.3760   -1.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2855    1.3972    0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4150   -1.9316    0.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9570   -1.4297    2.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1162    2.2840    5.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2081    2.6351    3.7555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0033    2.7241    3.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4547   -0.9669    2.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8887    0.1660   -1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6239   -1.3966   -2.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0928   -3.1888   -1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6465    1.7086   -0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7156    1.6572    1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181    1.4460    1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5727   -2.1182    1.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158   -0.6420    2.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5136    0.1015    2.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5789   -1.5135    2.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9213   -1.3199    0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4185   -2.5940   -1.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8862   -1.1022   -2.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9812   -1.8299   -1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4485    1.1390   -1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6645    1.2592    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9488    0.6120   -0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4825   -1.9467   -0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
  7 21  1  0  0  0  0
 28 29  1  6  0  0  0
 16 15  2  0  0  0  0
 28 30  1  0  0  0  0
 15 10  1  0  0  0  0
 26 27  1  0  0  0  0
 26 25  1  0  0  0  0
 23 24  1  1  0  0  0
  2  3  2  0  0  0  0
 31 65  1  6  0  0  0
 16 21  1  0  0  0  0
  2  1  1  0  0  0  0
  4  2  1  0  0  0  0
 27 28  1  0  0  0  0
 23  9  1  0  0  0  0
 21 20  1  0  0  0  0
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 19 17  1  0  0  0  0
 17 16  1  0  0  0  0
 31  5  1  0  0  0  0
 17 18  2  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  1  0  0  0
  6  7  1  0  0  0  0
 10 11  1  0  0  0  0
  9  7  1  0  0  0  0
 11 12  1  0  0  0  0
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 12 13  1  0  0  0  0
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 21 22  1  6  0  0  0
  9 10  1  0  0  0  0
  9 41  1  6  0  0  0
  5  4  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
 26 55  1  0  0  0  0
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 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
  5 35  1  1  0  0  0
  6 36  1  0  0  0  0
  6 37  1  0  0  0  0
 15 46  1  0  0  0  0
 10 42  1  1  0  0  0
 24 50  1  0  0  0  0
 24 51  1  0  0  0  0
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 29 59  1  0  0  0  0
 29 60  1  0  0  0  0
 29 61  1  0  0  0  0
 30 62  1  0  0  0  0
 30 63  1  0  0  0  0
 30 64  1  0  0  0  0
 20 47  1  0  0  0  0
 20 48  1  0  0  0  0
  8 38  1  0  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
 13 45  1  0  0  0  0
 22 49  1  0  0  0  0
M  END

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
    0.1247   -0.6130   -5.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757    0.0120   -4.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2080    1.0573   -4.3420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3994   -0.7534   -3.1766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -0.2710   -1.9620 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4742   -0.7339   -1.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3128   -0.4096   -0.7380 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6551    1.0989   -0.7567 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2841    0.6296    2.4194 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9494   -1.4066   -1.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2754   -2.6594   -0.9685 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2838   -0.8625   -0.7106 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.9487    0.8200   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6593   -2.5329    0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4185   -2.5940   -1.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4485    1.1390   -1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6645    1.2592    0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9488    0.6120   -0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4825   -1.9467   -0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
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 13 43  1  0
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 13 45  1  0
 22 49  1  0
M  END


  Mrv1652306202122473D          

 65 68  0  0  0  0            999 V2000
    0.1247   -0.6130   -5.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757    0.0120   -4.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2080    1.0573   -4.3420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3994   -0.7534   -3.1766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -0.2710   -1.9620 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0037980

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12C(=C([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]3([H])[C@@]4(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]4([H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@@]13C([H])([H])[H])C(=O)OC2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O7/c1-13(25)30-16-10-15-20(27)29-12-24(15,28)23(6)11-17(31-14(2)26)18-21(3,4)8-7-9-22(18,5)19(16)23/h10,16-19,28H,7-9,11-12H2,1-6H3/t16-,17-,18-,19+,22-,23+,24-/m0/s1

> <INCHI_KEY>
PLZQGNUEUWYONM-VAXCZNHBSA-N

> <FORMULA>
C24H34O7

> <MOLECULAR_WEIGHT>
434.529

> <EXACT_MASS>
434.230453435

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.145717336789545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,7S,8S,10R,11R,17S)-8-(acetyloxy)-11-hydroxy-2,6,6,10-tetramethyl-14-oxo-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-15-en-17-yl acetate

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
2.403800139666667

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.74584586289263

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7847670195707623

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
111.07490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,7S,8S,10R,11R,17S)-8-(acetyloxy)-11-hydroxy-2,6,6,10-tetramethyl-14-oxo-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-15-en-17-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
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  8 38  1  0
  8 39  1  0
  8 40  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 22 49  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       0.125  -0.613  -5.457  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.576   0.012  -4.289  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.208   1.057  -4.342  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.399  -0.753  -3.177  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.008  -0.271  -1.962  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.474  -0.734  -1.999  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.313  -0.410  -0.738  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.655   1.099  -0.757  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.510  -0.837   0.561  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.357  -0.700   1.890  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.284   0.630   2.419  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.200   0.748   3.773  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.126   2.195   4.152  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.180  -0.176   4.572  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.827  -0.987   1.714  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.369  -1.229   0.516  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.800  -1.429   0.233  0.00  0.00           C+0
HETATM   18  O   UNK     0      -7.683  -1.611   1.048  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.949  -1.407  -1.123  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.741  -0.905  -1.733  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.628  -1.278  -0.764  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.275  -2.659  -0.969  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.991  -0.353   0.621  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.839   1.181   0.803  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.319  -1.050   1.841  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.200  -0.930   1.879  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.833  -1.449   0.601  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.299  -0.793  -0.700  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.920  -1.626  -1.854  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.859   0.634  -0.844  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.284  -0.863  -0.711  0.00  0.00           C+0
HETATM   32  H   UNK     0      -0.236  -1.634  -5.603  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.094  -0.038  -6.361  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.204  -0.606  -5.288  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.949   0.820  -1.951  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.973  -0.323  -2.886  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.456  -1.816  -2.183  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.184   1.376  -1.675  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.769   1.733  -0.750  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.285   1.397   0.085  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.415  -1.932   0.458  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.957  -1.430   2.606  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.116   2.284   5.242  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.208   2.635   3.756  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.003   2.724   3.770  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.455  -0.967   2.603  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.889   0.166  -1.889  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.624  -1.397  -2.704  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.093  -3.189  -1.021  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.647   1.709  -0.132  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.716   1.657   1.236  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.018   1.446   1.474  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.573  -2.118   1.837  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.716  -0.642   2.778  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.514   0.102   2.067  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.579  -1.514   2.727  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.659  -2.533   0.555  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.921  -1.320   0.671  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.419  -2.594  -1.965  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.886  -1.102  -2.813  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.981  -1.830  -1.665  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.448   1.139  -1.724  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.665   1.259   0.028  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.949   0.612  -0.965  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.483  -1.947  -0.753  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    3    1    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5   31    6    4   35                                             
CONECT    6    5    7   36   37                                             
CONECT    7   21    8    6    9                                             
CONECT    8    7   38   39   40                                             
CONECT    9   23    7   10   41                                             
CONECT   10   15   11    9   42                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12   43   44   45                                             
CONECT   14   12                                                            
CONECT   15   16   10   46                                                  
CONECT   16   15   21   17                                                  
CONECT   17   19   16   18                                                  
CONECT   18   17                                                            
CONECT   19   20   17                                                       
CONECT   20   21   19   47   48                                             
CONECT   21    7   16   20   22                                             
CONECT   22   21   49                                                       
CONECT   23   24    9   25   31                                             
CONECT   24   23   50   51   52                                             
CONECT   25   26   23   53   54                                             
CONECT   26   27   25   55   56                                             
CONECT   27   26   28   57   58                                             
CONECT   28   29   30   27   31                                             
CONECT   29   28   59   60   61                                             
CONECT   30   28   62   63   64                                             
CONECT   31   65    5   28   23                                             
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    5                                                            
CONECT   36    6                                                            
CONECT   37    6                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   13                                                            
CONECT   46   15                                                            
CONECT   47   20                                                            
CONECT   48   20                                                            
CONECT   49   22                                                            
CONECT   50   24                                                            
CONECT   51   24                                                            
CONECT   52   24                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   26                                                            
CONECT   57   27                                                            
CONECT   58   27                                                            
CONECT   59   29                                                            
CONECT   60   29                                                            
CONECT   61   29                                                            
CONECT   62   30                                                            
CONECT   63   30                                                            
CONECT   64   30                                                            
CONECT   65   31                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  136    0
END

RDKit          3D

65 68  0  0  0  0  0  0  0  0999 V2000
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  7 21  1  0
 28 29  1  6
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 15 10  1  0
 26 27  1  0
 26 25  1  0
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  2  3  2  0
 31 65  1  6
 16 21  1  0
  2  1  1  0
  4  2  1  0
 27 28  1  0
 23  9  1  0
 21 20  1  0
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 17 16  1  0
 31  5  1  0
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  9  7  1  0
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  1 32  1  0
  1 33  1  0
  1 34  1  0
 26 55  1  0
 26 56  1  0
 27 57  1  0
 27 58  1  0
 25 53  1  0
 25 54  1  0
  5 35  1  1
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  6 37  1  0
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 30 64  1  0
 20 47  1  0
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  8 38  1  0
  8 39  1  0
  8 40  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 22 49  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1R)-1,2-(Methyleneoxycarbonyl)-4a,9b-diacetoxy-4balpha,8,8,10aalpha-tetramethyl-1,4,4abeta,4b,5,6,7,8,8abeta,9,10,10a-dodecahydrophenanthrene-1b-ol	Generator
(1R)-1,2-(Methyleneoxycarbonyl)-4α,9β-diacetoxy-4balpha,8,8,10aalpha-tetramethyl-1,4,4abeta,4b,5,6,7,8,8abeta,9,10,10a-dodecahydrophenanthrene-1β-ol	Generator

Chemical Formula

C₂₄H₃₄O₇

Average Mass

434.5290 Da

Monoisotopic Mass

434.23045 Da

IUPAC Name

(1R,2S,7S,8S,10R,11R,17S)-8-(acetyloxy)-11-hydroxy-2,6,6,10-tetramethyl-14-oxo-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-15-en-17-yl acetate

Traditional Name

(1R,2S,7S,8S,10R,11R,17S)-8-(acetyloxy)-11-hydroxy-2,6,6,10-tetramethyl-14-oxo-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-15-en-17-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]12C(=C([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]3([H])[C@@]4(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]4([H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@@]13C([H])([H])[H])C(=O)OC2([H])[H]

InChI Identifier

InChI=1S/C24H34O7/c1-13(25)30-16-10-15-20(27)29-12-24(15,28)23(6)11-17(31-14(2)26)18-21(3,4)8-7-9-22(18,5)19(16)23/h10,16-19,28H,7-9,11-12H2,1-6H3/t16-,17-,18-,19+,22-,23+,24-/m0/s1

InChI Key

PLZQGNUEUWYONM-VAXCZNHBSA-N

Experimental Spectra

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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dysidea cf. arenaria	JEOL database	Agena, M., et al, Tetrahedron 65, 1495 (2009)

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.94	ALOGPS
logP	2.4	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	12.75	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111.07 m³·mol⁻¹	ChemAxon
Polarizability	46.15 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

27023998

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25215192

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Agena, M., et al. (2009). Agena, M., et al, Tetrahedron 65, 1495 (2009). Tetrahedron.

Showing NP-Card for acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+ (NP0037980)

MOL for NP0037980 (acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+)

3D MOL for NP0037980 (acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+)

3D SDF for NP0037980 (acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+)

3D-SDF for NP0037980 (acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+)

PDB for NP0037980 (acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+)

3D PDB for NP0037980 (acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+)

SMILES for NP0037980 (acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+)

INCHI for NP0037980 (acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+)

Structure for NP0037980 (acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+)

3D Structure for NP0037980 (acetic acid 10-acetoxy-3a-hydroxy-3b,6,6,9a-tetramethyl-1-oxo-1,3,3a,3b,4+)