NP-MRD: Showing NP-Card for (1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid (NP0239313)

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Record Information

Version

2.0

Created at

2022-09-06 22:53:05 UTC

Updated at

2022-09-06 22:53:05 UTC

NP-MRD ID

NP0239313

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid

Description

(1S,2S,3R,4aS,4bR,6aS,7S,10aS,10bR,12S,12aS)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3S)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-octadecahydrochrysene-1-carboxylic acid belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. (1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid is found in Phyllospongia papyracea. Based on a literature review very few articles have been published on (1S,2S,3R,4aS,4bR,6aS,7S,10aS,10bR,12S,12aS)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3S)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-octadecahydrochrysene-1-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072200532D          

 42 45  0  0  1  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7599   -5.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2902   -4.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
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 36 37  2  0  0  0  0
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 35 39  1  0  0  0  0
  9 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
M  END

     RDKit          3D

 96 99  0  0  0  0  0  0  0  0999 V2000
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    4.0778    2.4328    1.0321 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1730    1.1442    1.5480 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8846    2.4969    0.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9919    1.5279   -1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368    1.7311   -1.9926 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2605    0.3610   -0.9874 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3161   -0.6109   -2.0446 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8522   -0.6760   -2.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
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 41 96  1  0
 38 92  1  0
M  END


  Mrv1652309072200532D          

 42 45  0  0  1  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7599   -5.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2902   -4.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777   -4.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 26 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 11 33  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  6  0  0  0
 12 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 35 39  1  0  0  0  0
  9 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0239313

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](O)CC(=O)O[C@@H]1C[C@H]2[C@]3(C)CC[C@H]4[C@@](C)(CC)CCC[C@]4(C)[C@H]3C[C@H](OC(C)=O)[C@]2(C)[C@H]([C@@H]1C(C)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H54O8/c1-9-21(37)16-27(38)42-22-17-25-33(7)15-12-23-31(5,10-2)13-11-14-32(23,6)24(33)18-26(41-20(4)36)34(25,8)29(30(39)40)28(22)19(3)35/h21-26,28-29,37H,9-18H2,1-8H3,(H,39,40)/t21-,22+,23-,24+,25-,26-,28+,29+,31-,32-,33+,34+/m0/s1

> <INCHI_KEY>
VFBXOXMDEZSTGF-GFABKKOPSA-N

> <FORMULA>
C34H54O8

> <MOLECULAR_WEIGHT>
590.798

> <EXACT_MASS>
590.381868699

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
66.80310439970117

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3R,4aS,4bR,6aS,7S,10aS,10bR,12S,12aS)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3S)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-octadecahydrochrysene-1-carboxylic acid

> <JCHEM_LOGP>
5.152142437333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.009055952151495

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.201520030251295

> <JCHEM_PKA_STRONGEST_BASIC>
-2.794810775933845

> <JCHEM_POLAR_SURFACE_AREA>
127.20000000000002

> <JCHEM_REFRACTIVITY>
156.85630000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,4aS,4bR,6aS,7S,10aS,10bR,12S,12aS)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3S)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670  -8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.004 -12.320   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669 -10.780   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.152 -10.277   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.142  -8.563   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.625  -8.295   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      17.338  -6.930   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      16.004  -9.240   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      17.338  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   39                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   33                                                  
CONECT   12   11   13   14   35                                             
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22   23   30                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   30                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   26   21   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   11   20   34                                             
CONECT   34   33                                                            
CONECT   35   12   36   39                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   35    9   40                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,3R,4AS,4BR,6as,7S,10as,10BR,12S,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3S)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-octadecahydrochrysene-1-carboxylate	Generator

Chemical Formula

C₃₄H₅₄O₈

Average Mass

590.7980 Da

Monoisotopic Mass

590.38187 Da

IUPAC Name

(1S,2S,3R,4aS,4bR,6aS,7S,10aS,10bR,12S,12aS)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3S)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-octadecahydrochrysene-1-carboxylic acid

Traditional Name

(1S,2S,3R,4aS,4bR,6aS,7S,10aS,10bR,12S,12aS)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3S)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC[C@H](O)CC(=O)O[C@@H]1C[C@H]2[C@]3(C)CC[C@H]4[C@@](C)(CC)CCC[C@]4(C)[C@H]3C[C@H](OC(C)=O)[C@]2(C)[C@H]([C@@H]1C(C)=O)C(O)=O

InChI Identifier

InChI=1S/C34H54O8/c1-9-21(37)16-27(38)42-22-17-25-33(7)15-12-23-31(5,10-2)13-11-14-32(23,6)24(33)18-26(41-20(4)36)34(25,8)29(30(39)40)28(22)19(3)35/h21-26,28-29,37H,9-18H2,1-8H3,(H,39,40)/t21-,22+,23-,24+,25-,26-,28+,29+,31-,32-,33+,34+/m0/s1

InChI Key

VFBXOXMDEZSTGF-GFABKKOPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phyllospongia papyracea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
Oxosteroid
17-oxosteroid
15-hydroxysteroid
Hydroxysteroid
Steroid
Tricarboxylic acid or derivatives
Gamma-keto acid
Beta-hydroxy acid
Fatty acid ester
Fatty acyl
Hydroxy acid
Keto acid
Carboxylic acid ester
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
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	5.15	ChemAxon
pKa (Strongest Acidic)	4.2	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	127.2 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	156.86 m³·mol⁻¹	ChemAxon
Polarizability	66.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

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DrugBank ID

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Phenol Explorer Compound ID

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FoodDB ID

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KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

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BioCyc ID

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BiGG ID

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Wikipedia Link

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METLIN ID

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PubChem Compound

162893890

PDB ID

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ChEBI ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid (NP0239313)

MOL for NP0239313 ((1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid)

3D MOL for NP0239313 ((1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid)

3D SDF for NP0239313 ((1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid)

3D-SDF for NP0239313 ((1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid)

PDB for NP0239313 ((1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid)

3D PDB for NP0239313 ((1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid)

SMILES for NP0239313 ((1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid)

INCHI for NP0239313 ((1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid)

Structure for NP0239313 ((1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid)

3D Structure for NP0239313 ((1s,2s,3r,4as,4br,6as,7s,10as,10br,12s,12as)-2-acetyl-12-(acetyloxy)-7-ethyl-3-{[(3s)-3-hydroxypentanoyl]oxy}-4b,7,10a,12a-tetramethyl-tetradecahydrochrysene-1-carboxylic acid)