NP-MRD: Showing NP-Card for 7a,12a-Dihydroxy-5a-cholestan-3-one (NP0334771)

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Record Information

Version

2.0

Created at

2024-09-10 19:53:29 UTC

Updated at

2024-09-10 19:53:29 UTC

NP-MRD ID

NP0334771

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7a,12a-Dihydroxy-5a-cholestan-3-one

Description

7A,12a-Dihydroxy-5a-cholestan-3-one belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. 7A,12a-Dihydroxy-5a-cholestan-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa). The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. 7Alpha,12alpha-Dihydroxy-5alpha-cholestan-3-one is an intermediate in bile acid biosynthesis. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231220542D          

 33 36  0  0  1  0            999 V2000
   12.7330  -10.4070    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9974   -9.1049    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1525  -10.4667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5390   -5.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1800   -5.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0561   -7.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4252   -9.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7131   -8.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6701   -6.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4771   -6.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4152   -7.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8382   -9.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3533   -9.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9962  -10.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7107   -9.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7107  -11.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1396  -11.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1396   -8.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7320   -5.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6082   -7.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4252  -10.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9962  -10.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3533   -8.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5686   -9.6753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1396   -9.6753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8541  -10.9128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8541   -8.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8541  -10.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4252  -10.0878    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5686   -8.8503    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2818  -11.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5686  -11.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8541   -7.6128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4 19  1  0  0  0  0
  5 19  1  0  0  0  0
  6 20  1  0  0  0  0
 29  7  1  1  0  0  0
 30  8  1  1  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 19  1  0  0  0  0
 11 20  1  0  0  0  0
 12 23  1  0  0  0  0
 12 13  1  0  0  0  0
 13 24  1  0  0  0  0
 14 15  1  0  0  0  0
 14 22  1  0  0  0  0
 15 29  1  0  0  0  0
 16 22  1  0  0  0  0
 21 16  1  0  0  0  0
 17 21  1  0  0  0  0
 17 26  1  0  0  0  0
 18 25  1  0  0  0  0
 18 27  1  0  0  0  0
 20 23  1  0  0  0  0
 21 29  1  0  0  0  0
 22 31  2  0  0  0  0
 23 30  1  0  0  0  0
 24 28  1  0  0  0  0
 24 30  1  0  0  0  0
 25 28  1  0  0  0  0
 25 29  1  0  0  0  0
 26 28  1  0  0  0  0
 26 32  1  6  0  0  0
 27 33  1  1  0  0  0
 27 30  1  0  0  0  0
 25  3  1  6  0  0  0
 27  2  1  6  0  0  0
 24  1  1  6  0  0  0
M  END


  Mrv0541 02231220542D          

 33 36  0  0  1  0            999 V2000
   12.7330  -10.4070    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9974   -9.1049    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1525  -10.4667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5390   -5.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1800   -5.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0561   -7.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4252   -9.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7131   -8.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6701   -6.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4771   -6.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4152   -7.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8382   -9.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3533   -9.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9962  -10.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7107   -9.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7107  -11.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1396  -11.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1396   -8.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7320   -5.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6082   -7.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4252  -10.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9962  -10.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3533   -8.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5686   -9.6753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1396   -9.6753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8541  -10.9128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8541   -8.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8541  -10.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4252  -10.0878    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5686   -8.8503    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2818  -11.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5686  -11.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8541   -7.6128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4 19  1  0  0  0  0
  5 19  1  0  0  0  0
  6 20  1  0  0  0  0
 29  7  1  1  0  0  0
 30  8  1  1  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 19  1  0  0  0  0
 11 20  1  0  0  0  0
 12 23  1  0  0  0  0
 12 13  1  0  0  0  0
 13 24  1  0  0  0  0
 14 15  1  0  0  0  0
 14 22  1  0  0  0  0
 15 29  1  0  0  0  0
 16 22  1  0  0  0  0
 21 16  1  0  0  0  0
 17 21  1  0  0  0  0
 17 26  1  0  0  0  0
 18 25  1  0  0  0  0
 18 27  1  0  0  0  0
 20 23  1  0  0  0  0
 21 29  1  0  0  0  0
 22 31  2  0  0  0  0
 23 30  1  0  0  0  0
 24 28  1  0  0  0  0
 24 30  1  0  0  0  0
 25 28  1  0  0  0  0
 25 29  1  0  0  0  0
 26 28  1  0  0  0  0
 26 32  1  6  0  0  0
 27 33  1  1  0  0  0
 27 30  1  0  0  0  0
 25  3  1  6  0  0  0
 27  2  1  6  0  0  0
 24  1  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0334771

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC(C(C)CCCC(C)C)[C@@]1(C)C([H])(O)C[C@@]1([H])C2[C@H](O)CC2CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-18,20-25,29-30H,6-15H2,1-5H3/t17?,18?,20?,21-,22-,23+,24+,25?,26-,27+/m0/s1

> <INCHI_KEY>
HHVQPBXBALLUDF-BNGOGRIJSA-N

> <FORMULA>
C27H46O3

> <MOLECULAR_WEIGHT>
418.6523

> <EXACT_MASS>
418.344695338

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
51.19850468154798

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,9R,11S,15R)-9,16-dihydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

> <ALOGPS_LOGP>
4.73

> <JCHEM_LOGP>
5.186393449666669

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.986676644374217

> <JCHEM_PKA_STRONGEST_BASIC>
-0.17839052846966374

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
121.84639999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,9R,11S,15R)-9,16-dihydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  H   UNK     0      23.768 -19.426   0.000  0.00  0.00           H+0
HETATM    2  H   UNK     0      22.395 -16.996   0.000  0.00  0.00           H+0
HETATM    3  H   UNK     0      20.818 -19.538   0.000  0.00  0.00           H+0
HETATM    4  C   UNK     0      30.873 -10.690   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.336  -9.866   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.371 -13.436   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.460 -17.291   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.731 -15.004   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.384 -12.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.891 -12.475   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.908 -14.260   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.831 -17.291   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.926 -18.536   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.793 -18.831   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.127 -18.061   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.127 -21.141   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.794 -21.141   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.794 -16.521   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.366 -11.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.402 -14.580   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.460 -20.371   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.793 -20.371   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.926 -16.045   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.461 -18.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.794 -18.061   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.128 -20.371   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.128 -15.751   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.128 -18.831   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      19.460 -18.831   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.461 -16.521   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      15.459 -21.141   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      23.461 -21.141   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      22.128 -14.211   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2   27                                                            
CONECT    3   25                                                            
CONECT    4   19                                                            
CONECT    5   19                                                            
CONECT    6   20                                                            
CONECT    7   29                                                            
CONECT    8   30                                                            
CONECT    9   10   11                                                       
CONECT   10    9   19                                                       
CONECT   11    9   20                                                       
CONECT   12   23   13                                                       
CONECT   13   12   24                                                       
CONECT   14   15   22                                                       
CONECT   15   14   29                                                       
CONECT   16   22   21                                                       
CONECT   17   21   26                                                       
CONECT   18   25   27                                                       
CONECT   19    4    5   10                                                  
CONECT   20    6   11   23                                                  
CONECT   21   16   17   29                                                  
CONECT   22   14   16   31                                                  
CONECT   23   12   20   30                                                  
CONECT   24   13   28   30    1                                             
CONECT   25   18   28   29    3                                             
CONECT   26   17   28   32                                                  
CONECT   27   18   33   30    2                                             
CONECT   28   24   25   26                                                  
CONECT   29    7   15   21   25                                             
CONECT   30    8   23   24   27                                             
CONECT   31   22                                                            
CONECT   32   26                                                            
CONECT   33   27                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₆O₃

Average Mass

418.6523 Da

Monoisotopic Mass

418.34470 Da

IUPAC Name

(1S,2S,9R,11S,15R)-9,16-dihydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

Traditional Name

(1S,2S,9R,11S,15R)-9,16-dihydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(C(C)CCCC(C)C)[C@@]1(C)C([H])(O)C[C@@]1([H])C2[C@H](O)CC2CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C27H46O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-18,20-25,29-30H,6-15H2,1-5H3/t17?,18?,20?,21-,22-,23+,24+,25?,26-,27+/m0/s1

InChI Key

HHVQPBXBALLUDF-BNGOGRIJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
3-oxosteroid
12-hydroxysteroid
Hydroxysteroid
Oxosteroid
7-hydroxysteroid
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	4.73	ALOGPS
logP	5.19	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	19.99	ChemAxon
pKa (Strongest Basic)	-0.18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.85 m³·mol⁻¹	ChemAxon
Polarizability	51.2 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	No	ChemAxon

External Links

HMDB ID

HMDB0006886

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB024133

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05458

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477902

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 7a,12a-Dihydroxy-5a-cholestan-3-one (NP0334771)

MOL for NP0334771 (7a,12a-Dihydroxy-5a-cholestan-3-one)

3D MOL for NP0334771 (7a,12a-Dihydroxy-5a-cholestan-3-one)

3D SDF for NP0334771 (7a,12a-Dihydroxy-5a-cholestan-3-one)

3D-SDF for NP0334771 (7a,12a-Dihydroxy-5a-cholestan-3-one)

PDB for NP0334771 (7a,12a-Dihydroxy-5a-cholestan-3-one)

3D PDB for NP0334771 (7a,12a-Dihydroxy-5a-cholestan-3-one)

SMILES for NP0334771 (7a,12a-Dihydroxy-5a-cholestan-3-one)

INCHI for NP0334771 (7a,12a-Dihydroxy-5a-cholestan-3-one)

Structure for NP0334771 (7a,12a-Dihydroxy-5a-cholestan-3-one)

3D Structure for NP0334771 (7a,12a-Dihydroxy-5a-cholestan-3-one)