NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate (NP0316437)

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Record Information

Version

2.0

Created at

2022-09-11 15:38:14 UTC

Updated at

2022-09-11 15:38:14 UTC

NP-MRD ID

NP0316437

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate

Description

Stigmasta-5-ene-3beta-yl 6-O-(1-oxo-9,12-octadecadienyl)-beta-D-glucopyranoside belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. [(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate is found in Actaea racemosa. Based on a literature review very few articles have been published on Stigmasta-5-ene-3beta-yl 6-O-(1-oxo-9,12-octadecadienyl)-beta-D-glucopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112217382D          

 60 64  0  0  1  0            999 V2000
  -13.5749  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737  -10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -9.4875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -9.4875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -9.4875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868  -11.5500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868  -10.7250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -11.5500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4694  -11.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -11.9625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1728  -12.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9933  -12.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3289  -12.1020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1358  -11.9305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6879  -12.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3908  -11.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1977  -10.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4527  -10.1897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2597  -10.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5146   -9.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9007   -9.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0937   -9.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1556   -8.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289  -10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -10.7250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -10.3125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289  -10.7250    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  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 34 33  1  6  0  0  0
 34 35  1  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
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 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 38 43  1  0  0  0  0
 43 44  1  1  0  0  0
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 48 49  1  0  0  0  0
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 31 54  1  0  0  0  0
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 22 59  1  0  0  0  0
 59 60  1  6  0  0  0
M  END

     RDKit          3D

150154  0  0  0  0  0  0  0  0999 V2000
   17.0302    0.2675   -0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0013    1.0070   -1.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8003    1.8016   -1.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5299    1.0767   -2.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0460    0.2928   -0.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6961   -0.3430   -1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6603   -0.0458   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2995   -0.5785   -0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3342    0.5445   -0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6235    0.5422   -1.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6392    1.5445   -2.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3475    2.6571   -1.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7810    2.3171   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4682    1.5259   -0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4802    2.3506   -0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1048    1.8642   -1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7914    0.6500   -1.8648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2304   -0.6608   -1.3739 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6558   -2.1710    2.0504 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2727   -0.2167   -0.8974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5746   -0.5141   -0.1910 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1117   -1.8750   -0.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2690   -0.3889    1.2842 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.6620   -0.5260    1.8318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3555    0.5402    0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5895    0.5840   -0.3591 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5314    0.3837   -1.4875 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8278    0.2279   -2.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3832    1.6026   -1.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.9373   -0.8353   -0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.2455    0.6233    0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.0292    0.4616    0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
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   17.2558    0.3099   -2.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
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   15.6742    2.5614   -1.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309112217382D          

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M  END
> <DATABASE_ID>
NP0316437

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C\C\C=C\CCCCCCCC(=O)OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C)[C@H]4CC[C@]5(C)[C@H](CC[C@H]5[C@@H]4CC=C3C2)[C@H](C)CC[C@@H](CC)C(C)C)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C53H90O7/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-47(54)58-36-46-48(55)49(56)50(57)51(60-46)59-41-31-33-52(6)40(35-41)27-28-42-44-30-29-43(53(44,7)34-32-45(42)52)38(5)25-26-39(9-2)37(3)4/h13-14,16-17,27,37-39,41-46,48-51,55-57H,8-12,15,18-26,28-36H2,1-7H3/b14-13+,17-16+/t38-,39-,41+,42+,43-,44+,45+,46-,48-,49+,50-,51-,52+,53-/m1/s1

> <INCHI_KEY>
LGOFPEZSCRRDEE-SCUISTCVSA-N

> <FORMULA>
C53H90O7

> <MOLECULAR_WEIGHT>
839.296

> <EXACT_MASS>
838.668655238

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
150

> <JCHEM_AVERAGE_POLARIZABILITY>
104.56754186877635

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9E,12E)-octadeca-9,12-dienoate

> <JCHEM_LOGP>
13.159989065333338

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.21480817275626

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.212166672319515

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490850980813834

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
247.20600000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9E,12E)-octadeca-9,12-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0     -25.340 -22.330   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -24.006 -21.560   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -22.673 -22.330   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -21.339 -21.560   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -20.005 -22.330   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -18.672 -21.560   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -17.338 -22.330   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -16.004 -21.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -16.004 -20.020   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -14.670 -19.250   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -14.670 -17.710   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -12.003 -17.710   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.336 -17.710   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668 -17.710   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.335 -15.400   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.001 -17.710   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334 -17.710   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.000 -16.940   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334 -17.710   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667 -16.940   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001 -17.710   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668 -17.710   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335 -20.020   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668 -22.330   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.002 -20.020   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.336 -19.250   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.669 -20.020   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.076 -20.934   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.336 -22.330   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.656 -23.836   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      11.188 -23.997   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      11.814 -22.590   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      13.320 -22.270   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      14.351 -23.415   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      13.796 -20.806   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      15.302 -20.485   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      15.778 -19.021   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      17.285 -18.701   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      17.761 -17.236   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      14.748 -17.876   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      13.242 -18.197   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      15.224 -16.412   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       2.667 -20.020   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       0.000 -20.020   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       0.000 -21.560   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      -1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      -2.667 -20.020   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   59                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   55                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   54                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   35                                             
CONECT   30   29                                                            
CONECT   31   29   32   54                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   40                                                  
CONECT   35   34   29   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40   43                                             
CONECT   39   38                                                            
CONECT   40   38   34   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   38   44                                                  
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   51                                                  
CONECT   49   48   50                                                       
CONECT   50   49                                                            
CONECT   51   48   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51                                                            
CONECT   54   31   26                                                       
CONECT   55   24   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   22   60                                                  
CONECT   60   59                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  128    0
END

View in JSmol

Synonyms

Value	Source
Stigmasta-5-ene-3b-yl 6-O-(1-oxo-9,12-octadecadienyl)-b-D-glucopyranoside	Generator
Stigmasta-5-ene-3β-yl 6-O-(1-oxo-9,12-octadecadienyl)-β-D-glucopyranoside	Generator

Chemical Formula

C₅₃H₉₀O₇

Average Mass

839.2960 Da

Monoisotopic Mass

838.66866 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-6-{[(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9E,12E)-octadeca-9,12-dienoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCCC\C=C\C\C=C\CCCCCCCC(=O)OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C)[C@H]4CC[C@]5(C)[C@H](CC[C@H]5[C@@H]4CC=C3C2)[C@H](C)CC[C@@H](CC)C(C)C)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C53H90O7/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-47(54)58-36-46-48(55)49(56)50(57)51(60-46)59-41-31-33-52(6)40(35-41)27-28-42-44-30-29-43(53(44,7)34-32-45(42)52)38(5)25-26-39(9-2)37(3)4/h13-14,16-17,27,37-39,41-46,48-51,55-57H,8-12,15,18-26,28-36H2,1-7H3/b14-13+,17-16+/t38-,39-,41+,42+,43-,44+,45+,46-,48-,49+,50-,51-,52+,53-/m1/s1

InChI Key

LGOFPEZSCRRDEE-SCUISTCVSA-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
Actaea racemosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Stigmastane-skeleton
Triterpenoid
Steroidal glycoside
Saccharolipid
Delta-5-steroid
Octadecanoid
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	13.16	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	247.21 m³·mol⁻¹	ChemAxon
Polarizability	104.57 Å³	ChemAxon
Number of Rings	5	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

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

71696418

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate (NP0316437)

MOL for NP0316437 ([(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate)

3D MOL for NP0316437 ([(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate)

3D SDF for NP0316437 ([(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate)

3D-SDF for NP0316437 ([(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate)

PDB for NP0316437 ([(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate)

3D PDB for NP0316437 ([(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate)

SMILES for NP0316437 ([(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate)

INCHI for NP0316437 ([(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate)

Structure for NP0316437 ([(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate)

3D Structure for NP0316437 ([(2r,3s,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (9e,12e)-octadeca-9,12-dienoate)