NP-MRD: Showing NP-Card for (1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate (NP0165855)

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Record Information

Version

2.0

Created at

2022-09-03 01:05:57 UTC

Updated at

2022-09-03 01:05:58 UTC

NP-MRD ID

NP0165855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate

Description

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-8-yl hexadecanoate 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. (1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate is found in Dracaena draco and Ligularia przewalskii. Based on a literature review very few articles have been published on (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-8-yl hexadecanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032203052D          

 59 63  0  0  1  0            999 V2000
    6.4302  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.9000    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
    8.5737   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.1473   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4328   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7184   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.1473   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.5762   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5762   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.0052   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052   -9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.7197   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341   -9.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.1878   -9.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197  -10.3125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.8912  -11.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7117  -11.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0472  -10.4520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.8542  -10.2805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.4062  -10.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1091   -9.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9161   -9.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1710   -8.5397    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.9780   -8.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2330   -7.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6190   -7.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8120   -8.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8740   -7.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052   -9.9000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2907  -10.3125    0.0000 C   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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  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  1  1  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  1  0  0  0
 22 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 20 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  1  0  0  0
 42 44  1  0  0  0  0
 44 45  1  1  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 42 47  1  0  0  0  0
 47 48  1  1  0  0  0
 48 49  1  1  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 52 51  1  6  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 52 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  1  0  0  0  0
 44 58  1  0  0  0  0
 39 58  1  0  0  0  0
 58 59  1  6  0  0  0
 19 59  1  0  0  0  0
M  END

     RDKit          3D

149153  0  0  0  0  0  0  0  0999 V2000
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   -4.1896   -5.3990    6.9764 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7840   -5.8177    6.9909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4571   -4.4954    7.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1988   -3.4009    6.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0286   -3.7885    5.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3601   -2.8029    4.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7011   -2.5162    3.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2145   -1.4992    2.6690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763   -1.2192    1.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621   -2.4495    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4702   -3.0274    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9090   -4.0449   -1.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5444   -3.0647   -2.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4499   -1.0561   -6.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0239    0.6861   -4.7919 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4228    1.9879   -5.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8245    3.0860   -4.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6609    2.9291   -4.4050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2334    3.4169   -5.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1050    1.4950   -4.2005 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5699    1.7218   -4.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362    2.7910   -3.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4661    0.5162   -5.0803 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.5365   -4.6613    8.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309032203052D          

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M  END
> <DATABASE_ID>
NP0165855

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(=O)OC1=C2C[C@H](CC[C@]2(C)[C@H]2CC[C@]3(C)[C@H](CC[C@H]3[C@@H]2C1)[C@H](C)CC[C@@H](CC)C(C)C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C51H90O8/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-45(53)58-43-32-38-40-26-25-39(35(5)23-24-36(9-2)34(3)4)50(40,6)30-28-41(38)51(7)29-27-37(31-42(43)51)57-49-48(56)47(55)46(54)44(33-52)59-49/h34-41,44,46-49,52,54-56H,8-33H2,1-7H3/t35-,36-,37+,38+,39-,40+,41+,44-,46-,47+,48-,49-,50-,51-/m1/s1

> <INCHI_KEY>
HRUUTUFAJCLFFC-XAGKEMRUSA-N

> <FORMULA>
C51H90O8

> <MOLECULAR_WEIGHT>
831.273

> <EXACT_MASS>
830.663569858

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
149

> <JCHEM_AVERAGE_POLARIZABILITY>
104.53358979708499

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-8-yl hexadecanoate

> <ALOGPS_LOGP>
9.08

> <JCHEM_LOGP>
11.637641575333339

> <ALOGPS_LOGS>
-6.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200090020620166

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210561269738086

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835428539715

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
237.81710000000012

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.59e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-8-yl hexadecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      12.003 -19.250   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337 -18.480   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.670 -19.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.004 -18.480   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.338 -19.250   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.005 -19.250   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.339 -18.480   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.673 -19.250   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.006 -18.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.340 -19.250   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.674 -18.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.007 -19.250   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.341 -18.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.675 -19.250   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.008 -18.480   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      32.008 -16.940   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      33.342 -19.250   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      34.676 -18.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.676 -16.940   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      33.342 -16.170   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      33.342 -14.630   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      32.008 -13.860   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      32.008 -12.320   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      30.675 -11.550   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      30.675 -10.010   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      29.341  -9.240   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      29.341  -7.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      32.008  -9.240   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      32.008  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      33.342 -10.010   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      34.676  -9.240   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      33.342 -11.550   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      34.676 -12.320   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      34.676 -13.860   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      36.009 -14.630   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      36.009 -16.170   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      37.343 -15.400   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      37.343 -16.940   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      38.677 -16.170   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      40.010 -16.940   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      40.010 -18.480   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      41.417 -17.854   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      38.677 -19.250   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      38.997 -20.756   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      40.528 -20.917   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      41.155 -19.510   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      42.661 -19.190   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      43.692 -20.335   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      43.137 -17.726   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      44.643 -17.405   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      45.119 -15.941   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      46.626 -15.621   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      47.102 -14.156   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      44.089 -14.796   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      42.582 -15.117   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      44.565 -13.332   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      37.343 -18.480   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      36.009 -19.250   0.000  0.00  0.00           C+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   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   59                                                  
CONECT   20   19   21   37                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   24   34                                                  
CONECT   34   33                                                            
CONECT   35   22   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   20   38   39                                             
CONECT   38   37                                                            
CONECT   39   37   40   58                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44   47                                             
CONECT   43   42                                                            
CONECT   44   42   45   58                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   42   48                                                  
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53   55                                                  
CONECT   53   52   54                                                       
CONECT   54   53                                                            
CONECT   55   52   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55                                                            
CONECT   58   44   39   59                                                  
CONECT   59   58   19                                                       
MASTER        0    0    0    0    0    0    0    0   59    0  126    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-Ethyl-6-methylheptan-2-yl]-2,15-dimethyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0,.0,]heptadec-7-en-8-yl hexadecanoic acid	Generator

Chemical Formula

C₅₁H₉₀O₈

Average Mass

831.2730 Da

Monoisotopic Mass

830.66357 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)OC1=C2C[C@H](CC[C@]2(C)[C@H]2CC[C@]3(C)[C@H](CC[C@H]3[C@@H]2C1)[C@H](C)CC[C@@H](CC)C(C)C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C51H90O8/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-45(53)58-43-32-38-40-26-25-39(35(5)23-24-36(9-2)34(3)4)50(40,6)30-28-41(38)51(7)29-27-37(31-42(43)51)57-49-48(56)47(55)46(54)44(33-52)59-49/h34-41,44,46-49,52,54-56H,8-33H2,1-7H3/t35-,36-,37+,38+,39-,40+,41+,44-,46-,47+,48-,49-,50-,51-/m1/s1

InChI Key

HRUUTUFAJCLFFC-XAGKEMRUSA-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
Dracaena draco	LOTUS Database	35616633
Ligularia przewalskii	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
Steroid ester
Delta-5-steroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Enol ester
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Polyol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Alcohol
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	9.08	ALOGPS
logP	11.64	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	237.82 m³·mol⁻¹	ChemAxon
Polarizability	104.53 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

162890277

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate (NP0165855)

MOL for NP0165855 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate)

3D MOL for NP0165855 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate)

3D SDF for NP0165855 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate)

3D-SDF for NP0165855 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate)

PDB for NP0165855 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate)

3D PDB for NP0165855 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate)

SMILES for NP0165855 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate)

INCHI for NP0165855 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate)

Structure for NP0165855 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate)

3D Structure for NP0165855 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl hexadecanoate)