NP-MRD: Showing NP-Card for (1r,3as,3bs,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate (NP0161063)

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Record Information

Version

2.0

Created at

2022-09-02 19:09:35 UTC

Updated at

2022-09-02 19:09:35 UTC

NP-MRD ID

NP0161063

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,3bs,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate

Description

(1S,2R,9R,10S,11S,14R,15R,16R,17R)-9-(acetyloxy)-14-[(1S)-1-[(1S,3R,5R)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]Octan-3-yl]ethyl]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,6-dien-16-yl acetate belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. (1r,3as,3bs,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate is found in Petunia integrifolia. Based on a literature review very few articles have been published on (1S,2R,9R,10S,11S,14R,15R,16R,17R)-9-(acetyloxy)-14-[(1S)-1-[(1S,3R,5R)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]Octan-3-yl]ethyl]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,6-dien-16-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022221092D          

 44 49  0  0  1  0            999 V2000
    1.6463   -8.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -8.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251   -7.3258    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0294   -7.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3874   -6.3989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2124   -6.3989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6249   -5.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6249   -7.1133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2893   -7.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9024   -8.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6169   -8.0066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4015   -8.2615    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0146   -7.7095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8431   -6.9025    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4562   -6.3505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0585   -6.6475    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8870   -5.8406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -5.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3285   -4.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2847   -5.5435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4454   -7.1996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1904   -6.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7992   -7.9644    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6277   -7.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4123   -7.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1970   -7.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3685   -8.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1531   -8.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7554   -9.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9708   -8.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3577   -9.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5731   -9.0685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9600   -9.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1315  -10.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5184  -10.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9161  -10.6824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0294   -5.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251   -5.4720    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0416   -4.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4569   -6.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -5.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2242   -6.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -5.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -6.8114    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  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  1  0  0  0
  8  6  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 12 11  1  1  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 11 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 13 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
  5 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
  3 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
  3 44  1  0  0  0  0
M  END


  Mrv1652309022221092D          

 44 49  0  0  1  0            999 V2000
    1.6463   -8.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -8.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251   -7.3258    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0294   -7.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3874   -6.3989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2124   -6.3989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6249   -5.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6249   -7.1133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2893   -7.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9024   -8.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6169   -8.0066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4015   -8.2615    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0146   -7.7095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8431   -6.9025    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4562   -6.3505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0585   -6.6475    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8870   -5.8406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -5.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3285   -4.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2847   -5.5435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4454   -7.1996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1904   -6.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7992   -7.9644    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6277   -7.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4123   -7.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1970   -7.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3685   -8.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1531   -8.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7554   -9.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9708   -8.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3577   -9.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5731   -9.0685    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9600   -9.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1315  -10.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5184  -10.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9161  -10.6824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0294   -5.6556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251   -5.4720    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0416   -4.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4569   -6.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -5.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2242   -6.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -5.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801   -6.8114    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  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  1  0  0  0
  8  6  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 12 11  1  1  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 11 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 13 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
  5 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
  3 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
  3 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0161063

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12OC(C)(C)[C@@](C)(C[C@@H](O1)[C@@H](C)[C@H]1CC[C@H]3[C@@H]4[C@@H](CC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O)[C@H](OC(C)=O)[C@]13C)OC(C)=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C35H50O9/c1-10-35-42-26(17-33(8,44-35)31(5,6)43-35)18(2)23-11-12-24-27-25(40-19(3)36)16-21-15-22(38)13-14-32(21,7)28(27)29(39)30(34(23,24)9)41-20(4)37/h13-15,18,23-30,39H,10-12,16-17H2,1-9H3/t18-,23+,24-,25+,26+,27+,28+,29+,30-,32-,33+,34+,35-/m0/s1

> <INCHI_KEY>
HRENIFXKDLEZQP-YAVJBICVSA-N

> <FORMULA>
C35H50O9

> <MOLECULAR_WEIGHT>
614.776

> <EXACT_MASS>
614.34548319

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
67.61065118368668

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,9R,10S,11S,14R,15R,16R,17R)-9-(acetyloxy)-14-[(1S)-1-[(1S,3R,5R)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-16-yl acetate

> <ALOGPS_LOGP>
4.32

> <JCHEM_LOGP>
4.458208629333331

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.7052579128626

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.860931845229103

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2967004828329385

> <JCHEM_POLAR_SURFACE_AREA>
117.59

> <JCHEM_REFRACTIVITY>
162.8187

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,9R,10S,11S,14R,15R,16R,17R)-9-(acetyloxy)-14-[(1S)-1-[(1S,3R,5R)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-16-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       3.073 -16.224   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.944 -15.176   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.287 -13.675   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.788 -13.332   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.456 -11.945   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.996 -11.945   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.766 -10.611   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.766 -13.278   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.140 -14.685   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.285 -15.716   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.618 -14.946   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.083 -15.421   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.227 -14.391   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.907 -12.885   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.052 -11.854   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.442 -12.409   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.122 -10.902   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.267  -9.872   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.947  -8.366   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.731 -10.348   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.298 -13.439   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.822 -11.975   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.692 -14.867   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.372 -13.361   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.836 -13.836   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.301 -14.312   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.621 -15.819   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      17.086 -16.295   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.477 -16.849   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.012 -16.373   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.868 -17.404   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.403 -16.928   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.259 -17.958   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.579 -19.465   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.434 -20.495   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.043 -19.940   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.788 -10.557   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.287 -10.214   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.944  -8.713   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.719 -11.945   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.083 -11.175   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.418 -11.517   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.415  -9.787   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       1.083 -12.715   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   40   44                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13   32                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   11    8   22                                             
CONECT   22   21                                                            
CONECT   23   13   24   25   30                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   23   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   12   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37    5   38                                                       
CONECT   38   37   39   40   41                                             
CONECT   39   38                                                            
CONECT   40   38    3                                                       
CONECT   41   38   42   43   44                                             
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   41    3                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,9R,10S,11S,14R,15R,16R,17R)-9-(Acetyloxy)-14-[(1S)-1-[(1S,3R,5R)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadeca-3,6-dien-16-yl acetic acid	Generator

Chemical Formula

C₃₅H₅₀O₉

Average Mass

614.7760 Da

Monoisotopic Mass

614.34548 Da

IUPAC Name

(1S,2R,9R,10S,11S,14R,15R,16R,17R)-9-(acetyloxy)-14-[(1S)-1-[(1S,3R,5R)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-16-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@@]12OC(C)(C)[C@@](C)(C[C@@H](O1)[C@@H](C)[C@H]1CC[C@H]3[C@@H]4[C@@H](CC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O)[C@H](OC(C)=O)[C@]13C)OC(C)=O)O2

InChI Identifier

InChI=1S/C35H50O9/c1-10-35-42-26(17-33(8,44-35)31(5,6)43-35)18(2)23-11-12-24-27-25(40-19(3)36)16-21-15-22(38)13-14-32(21,7)28(27)29(39)30(34(23,24)9)41-20(4)37/h13-15,18,23-30,39H,10-12,16-17H2,1-9H3/t18-,23+,24-,25+,26+,27+,28+,29+,30-,32-,33+,34+,35-/m0/s1

InChI Key

HRENIFXKDLEZQP-YAVJBICVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Petunia integrifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
Steroid ester
3-oxo-delta-1,4-steroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
11-beta-hydroxysteroid
11-hydroxysteroid
Delta-1,4-steroid
1,3-dioxepane
Carboxylic acid orthoester
Ortho ester
Dioxepane
Meta-dioxane
Dicarboxylic acid or derivatives
Cyclic alcohol
Meta-dioxolane
Ketone
Orthocarboxylic acid derivative
Secondary alcohol
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen compound
Organic oxide
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	4.32	ALOGPS
logP	4.46	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	117.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	162.82 m³·mol⁻¹	ChemAxon
Polarizability	67.61 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

162923503

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,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate (NP0161063)

MOL for NP0161063 ((1r,3as,3bs,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D MOL for NP0161063 ((1r,3as,3bs,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D SDF for NP0161063 ((1r,3as,3bs,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D-SDF for NP0161063 ((1r,3as,3bs,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

PDB for NP0161063 ((1r,3as,3bs,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D PDB for NP0161063 ((1r,3as,3bs,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

SMILES for NP0161063 ((1r,3as,3bs,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

INCHI for NP0161063 ((1r,3as,3bs,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

Structure for NP0161063 ((1r,3as,3bs,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D Structure for NP0161063 ((1r,3as,3bs,4r,9ar,9bs,10r,11r,11ar)-4-(acetyloxy)-1-[(1s)-1-[(1s,3r,5r)-1-ethyl-5,6,6-trimethyl-2,7,8-trioxabicyclo[3.2.1]octan-3-yl]ethyl]-10-hydroxy-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)