NP-MRD: Showing NP-Card for (1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate (NP0223564)

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Record Information

Version

2.0

Created at

2022-09-06 01:41:53 UTC

Updated at

2022-09-06 01:41:53 UTC

NP-MRD ID

NP0223564

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate

Description

Agosterol C belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. (1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate was first documented in 2003 (PMID: 14510593). Based on a literature review very few articles have been published on Agosterol C.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062203412D          

 37 40  0  0  1  0            999 V2000
   -0.0184   -8.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5337   -9.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2787  -10.1537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3407   -9.1975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5956   -8.4129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0436   -7.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2985   -7.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1055   -6.8437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3604   -6.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8084   -5.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0014   -5.6175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1729   -4.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7465   -6.4021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0785   -6.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3335   -5.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340   -5.1326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3340   -4.3076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3805   -3.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0484   -3.8951    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0484   -3.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7629   -4.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4774   -3.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918   -4.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9063   -3.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918   -5.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575   -7.4568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9124   -6.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4645   -7.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0165   -7.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7616   -8.6830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3136   -9.2961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9546   -8.8545    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6997   -9.6391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2517  -10.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9968  -11.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0587  -10.0807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4026   -8.2414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  7  1  6  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  6  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 37 32  1  6  0  0  0
  5 37  1  0  0  0  0
 26 37  1  0  0  0  0
M  END


  Mrv1652309062203412D          

 37 40  0  0  1  0            999 V2000
   -0.0184   -8.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5337   -9.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2787  -10.1537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3407   -9.1975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5956   -8.4129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0436   -7.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2985   -7.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1055   -6.8437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3604   -6.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8084   -5.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0014   -5.6175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1729   -4.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7465   -6.4021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0785   -6.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3335   -5.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340   -5.1326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3340   -4.3076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3805   -3.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0484   -3.8951    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0484   -3.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7629   -4.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4774   -3.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918   -4.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9063   -3.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918   -5.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575   -7.4568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9124   -6.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4645   -7.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0165   -7.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7616   -8.6830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3136   -9.2961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9546   -8.8545    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6997   -9.6391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2517  -10.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9968  -11.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0587  -10.0807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4026   -8.2414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  7  1  6  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  6  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 37 32  1  6  0  0  0
  5 37  1  0  0  0  0
 26 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223564

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC[C@@H](O)[C@@H](C)[C@H]1CC[C@H]2C3=C[C@H](OC(C)=O)[C@H]4[C@@H](OC(C)=O)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C31H50O6/c1-17(2)8-11-25(34)18(3)22-9-10-23-21-16-27(36-19(4)32)28-29(37-20(5)33)26(35)13-15-31(28,7)24(21)12-14-30(22,23)6/h16-18,22-29,34-35H,8-15H2,1-7H3/t18-,22+,23-,24-,25+,26-,27-,28-,29-,30+,31+/m0/s1

> <INCHI_KEY>
TYLRRLLZCVWGTR-PHIAUZCSSA-N

> <FORMULA>
C31H50O6

> <MOLECULAR_WEIGHT>
518.735

> <EXACT_MASS>
518.36073933

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
60.572674626529455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,6R,7S,8S,11R,14R,15R)-6-(acetyloxy)-5-hydroxy-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-yl acetate

> <JCHEM_LOGP>
4.500170837333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.47784993703201

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.16077420659985

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8401878522618776

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
143.21319999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,6R,7S,8S,11R,14R,15R)-6-(acetyloxy)-5-hydroxy-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.034 -16.344   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.996 -17.489   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.520 -18.954   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.503 -17.169   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.978 -15.704   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.948 -14.560   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.424 -13.095   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.930 -12.775   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.406 -11.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.376 -10.166   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.869 -10.486   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.189  -8.980   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.393 -11.951   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.147 -11.951   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.622 -10.486   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.623  -9.581   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.623  -8.041   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.710  -7.271   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.957  -7.271   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.957  -5.731   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.291  -8.041   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.624  -7.271   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.958  -8.041   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.292  -7.271   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.958  -9.581   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.961 -13.919   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.437 -12.455   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.467 -13.599   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.497 -14.744   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.022 -16.208   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.052 -17.353   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.515 -16.528   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.039 -17.993   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.070 -19.137   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.594 -20.602   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.576 -18.817   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.485 -15.384   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   16                                             
CONECT   12   11                                                            
CONECT   13   11    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    8   27   28   37                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   32    5   26                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₅₀O₆

Average Mass

518.7350 Da

Monoisotopic Mass

518.36074 Da

IUPAC Name

(1R,2R,5S,6R,7S,8S,11R,14R,15R)-6-(acetyloxy)-5-hydroxy-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-yl acetate

Traditional Name

(1R,2R,5S,6R,7S,8S,11R,14R,15R)-6-(acetyloxy)-5-hydroxy-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)CC[C@@H](O)[C@@H](C)[C@H]1CC[C@H]2C3=C[C@H](OC(C)=O)[C@H]4[C@@H](OC(C)=O)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C31H50O6/c1-17(2)8-11-25(34)18(3)22-9-10-23-21-16-27(36-19(4)32)28-29(37-20(5)33)26(35)13-15-31(28,7)24(21)12-14-30(22,23)6/h16-18,22-29,34-35H,8-15H2,1-7H3/t18-,22+,23-,24-,25+,26-,27-,28-,29-,30+,31+/m0/s1

InChI Key

TYLRRLLZCVWGTR-PHIAUZCSSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholesterol-skeleton
Cholestane-skeleton
Dihydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
Steroid ester
3-hydroxy-delta-7-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
Oxosteroid
16-oxosteroid
Hydroxysteroid
Delta-7-steroid
Dicarboxylic acid or derivatives
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.5	ChemAxon
pKa (Strongest Acidic)	14.16	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	143.21 m³·mol⁻¹	ChemAxon
Polarizability	60.57 Å³	ChemAxon
Number of Rings	4	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

C00029650

Chemspider ID

8589719

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10414285

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tsukamoto S, Tatsuno M, van Soest RW, Yokosawa H, Ohta T: New polyhydroxy sterols: proteasome inhibitors from a marine sponge Acanthodendrilla sp. J Nat Prod. 2003 Sep;66(9):1181-5. doi: 10.1021/np030120v. [PubMed:14510593 ]
LOTUS database [Link]

Showing NP-Card for (1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate (NP0223564)

MOL for NP0223564 ((1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate)

3D MOL for NP0223564 ((1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate)

3D SDF for NP0223564 ((1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate)

3D-SDF for NP0223564 ((1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate)

PDB for NP0223564 ((1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate)

3D PDB for NP0223564 ((1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate)

SMILES for NP0223564 ((1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate)

INCHI for NP0223564 ((1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate)

Structure for NP0223564 ((1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate)

3D Structure for NP0223564 ((1r,3ar,5s,5as,6r,7s,9ar,9br,11ar)-6-(acetyloxy)-7-hydroxy-1-[(2s,3r)-3-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-yl acetate)