NP-MRD: Showing NP-Card for (1r,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol (NP0330804)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 16:31:07 UTC

Updated at

2022-09-12 16:31:07 UTC

NP-MRD ID

NP0330804

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol

Description

(1R,2R,5S,8R,10S,11S,12S,13R,14R,15R)-5-{[(2S,3R,4S,5R)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-14-[(2R,5R,7S)-7-hydroxy-5-(propan-2-yl)octan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-6-ene-8,10,12,13-tetrol 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,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol is found in Henricia sanguinolenta. Based on a literature review very few articles have been published on (1R,2R,5S,8R,10S,11S,12S,13R,14R,15R)-5-{[(2S,3R,4S,5R)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-14-[(2R,5R,7S)-7-hydroxy-5-(propan-2-yl)octan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-6-ene-8,10,12,13-tetrol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122218312D          

 46 50  0  0  1  0            999 V2000
   -8.1062    3.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3611    2.2406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1681    2.0691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.4230    1.2845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8710    0.6714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0640    0.8429    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8091    1.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0021    1.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7472    2.5837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2992    3.1968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9402    2.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3882    2.1421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1332    2.9267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812    2.3136    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1687    3.0281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5042    3.7818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3617    2.8566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7486    3.4086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2755    2.0361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5610    1.6236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5610    0.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8465    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1321    1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176    2.0361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2969    1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0114    2.0361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7258    1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0114    2.8611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176    2.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2969    3.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1321    3.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0291    1.7005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4161    1.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    0.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911    0.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6431    1.3575    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4501    1.1859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8980    0.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7050    0.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5120    0.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2300    1.1129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7820    1.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5271    2.5107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.0791    3.1237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7201    2.6822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.4652    3.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  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  6  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  1  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 19 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36 35  1  6  0  0  0
 12 36  1  0  0  0  0
 36 37  1  0  0  0  0
  8 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
  6 40  1  0  0  0  0
  4 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  1  0  0  0
 43 45  1  0  0  0  0
  3 45  1  0  0  0  0
 45 46  1  6  0  0  0
M  END


  Mrv1652309122218312D          

 46 50  0  0  1  0            999 V2000
   -8.1062    3.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3611    2.2406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1681    2.0691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.4230    1.2845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8710    0.6714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0640    0.8429    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8091    1.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0021    1.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7472    2.5837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2992    3.1968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9402    2.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3882    2.1421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1332    2.9267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5812    2.3136    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1687    3.0281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5042    3.7818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3617    2.8566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7486    3.4086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2755    2.0361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5610    1.6236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5610    0.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8465    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1321    1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176    2.0361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2969    1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0114    2.0361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7258    1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0114    2.8611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176    2.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2969    3.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1321    3.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0291    1.7005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4161    1.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841    0.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911    0.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6431    1.3575    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4501    1.1859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8980    0.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7050    0.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5120    0.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2300    1.1129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7820    1.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5271    2.5107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.0791    3.1237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7201    2.6822    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.4652    3.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  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  6  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  1  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 19 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36 35  1  6  0  0  0
 12 36  1  0  0  0  0
 36 37  1  0  0  0  0
  8 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
  6 40  1  0  0  0  0
  4 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  1  0  0  0
 43 45  1  0  0  0  0
  3 45  1  0  0  0  0
 45 46  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0330804

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@H](O[C@H]2CC[C@]3(C)[C@H]4CC[C@]5(C)[C@@H]([C@H](C)CC[C@H](C[C@H](C)O)C(C)C)[C@@H](O)[C@@H](O)[C@H]5[C@]4(O)C[C@@H](O)C3=C2)OC[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C36H62O10/c1-18(2)21(14-20(4)37)9-8-19(3)27-29(41)30(42)32-35(27,6)13-11-26-34(5)12-10-22(15-23(34)24(38)16-36(26,32)43)46-33-31(44-7)28(40)25(39)17-45-33/h15,18-22,24-33,37-43H,8-14,16-17H2,1-7H3/t19-,20+,21-,22+,24-,25-,26-,27+,28+,29-,30-,31-,32-,33+,34+,35-,36+/m1/s1

> <INCHI_KEY>
ZPVNGJGUGQFSPC-AOZDQXPJSA-N

> <FORMULA>
C36H62O10

> <MOLECULAR_WEIGHT>
654.882

> <EXACT_MASS>
654.434298196

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
108

> <JCHEM_AVERAGE_POLARIZABILITY>
75.62640519125895

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,8R,10S,11S,12S,13R,14R,15R)-5-{[(2S,3R,4S,5R)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-14-[(2R,5R,7S)-7-hydroxy-5-(propan-2-yl)octan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-8,10,12,13-tetrol

> <JCHEM_LOGP>
1.6778899449999987

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.458510777868508

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.733854894778442

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5393961596694812

> <JCHEM_POLAR_SURFACE_AREA>
169.29999999999998

> <JCHEM_REFRACTIVITY>
173.0168

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,8R,10S,11S,12S,13R,14R,15R)-5-{[(2S,3R,4S,5R)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-14-[(2R,5R,7S)-7-hydroxy-5-isopropyloctan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-8,10,12,13-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0     -15.132   5.647   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -15.607   4.182   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -17.114   3.862   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -17.590   2.398   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0     -16.559   1.253   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0     -15.053   1.573   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -14.577   3.038   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -13.071   3.358   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.595   4.823   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0     -13.625   5.967   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0     -11.088   5.143   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.058   3.999   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -9.582   5.463   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -8.552   4.319   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.782   5.652   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -8.408   7.059   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -6.275   5.332   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.131   6.363   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.114   3.801   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.781   3.031   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.781   1.491   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.447   3.801   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.113   3.031   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.780   3.801   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.554   3.031   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.888   3.801   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.222   3.031   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.888   5.341   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.780   5.341   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.554   6.111   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.113   6.111   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -7.521   3.174   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.377   2.144   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.997   1.710   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -9.503   1.390   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -10.534   2.534   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -12.040   2.214   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -11.010   1.069   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -12.516   0.749   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -14.022   0.429   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0     -19.096   2.077   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0     -20.126   3.222   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -19.651   4.687   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0     -20.681   5.831   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0     -18.144   5.007   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0     -17.668   6.471   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   45                                                  
CONECT    4    3    5   41                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   40                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   37                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   36                                             
CONECT   13   12                                                            
CONECT   14   12   15   32                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   32                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   19   14   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   12   37                                                  
CONECT   37   36    8   38   39                                             
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39    6                                                       
CONECT   41    4   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43    3   46                                                  
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₆₂O₁₀

Average Mass

654.8820 Da

Monoisotopic Mass

654.43430 Da

IUPAC Name

Traditional Name

(1R,2R,5S,8R,10S,11S,12S,13R,14R,15R)-5-{[(2S,3R,4S,5R)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-14-[(2R,5R,7S)-7-hydroxy-5-isopropyloctan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-8,10,12,13-tetrol

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@H](O[C@H]2CC[C@]3(C)[C@H]4CC[C@]5(C)[C@@H]([C@H](C)CC[C@H](C[C@H](C)O)C(C)C)[C@@H](O)[C@@H](O)[C@H]5[C@]4(O)C[C@@H](O)C3=C2)OC[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C36H62O10/c1-18(2)21(14-20(4)37)9-8-19(3)27-29(41)30(42)32-35(27,6)13-11-26-34(5)12-10-22(15-23(34)24(38)16-36(26,32)43)46-33-31(44-7)28(40)25(39)17-45-33/h15,18-22,24-33,37-43H,8-14,16-17H2,1-7H3/t19-,20+,21-,22+,24-,25-,26-,27+,28+,29-,30-,31-,32-,33+,34+,35-,36+/m1/s1

InChI Key

ZPVNGJGUGQFSPC-AOZDQXPJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Henricia sanguinolenta	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

Triterpenoid
Stigmastane-skeleton
Steroidal glycoside
6-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
16-hydroxysteroid
16-beta-hydroxysteroid
Delta-4-steroid
Glycosyl compound
O-glycosyl compound
Fatty alcohol
Oxane
Monosaccharide
Fatty acyl
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Ether
Dialkyl ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
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	1.68	ChemAxon
pKa (Strongest Acidic)	12.73	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	169.3 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	173.02 m³·mol⁻¹	ChemAxon
Polarizability	75.63 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

162888999

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol (NP0330804)

MOL for NP0330804 ((1r,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol)

3D MOL for NP0330804 ((1r,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol)

3D SDF for NP0330804 ((1r,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol)

3D-SDF for NP0330804 ((1r,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol)

PDB for NP0330804 ((1r,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol)

3D PDB for NP0330804 ((1r,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol)

SMILES for NP0330804 ((1r,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol)

INCHI for NP0330804 ((1r,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol)

Structure for NP0330804 ((1r,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol)

3D Structure for NP0330804 ((1r,2r,3s,3as,3bs,5r,7s,9ar,9br,11ar)-7-{[(2s,3r,4s,5r)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy}-1-[(2r,5r,7s)-7-hydroxy-5-isopropyloctan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,3,3b,5-tetrol)