NP-MRD: Showing NP-Card for 3b,17a,21-Trihydroxypregnenone (NP0334632)

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Record Information

Version

2.0

Created at

2024-09-10 19:13:52 UTC

Updated at

2024-09-10 19:13:52 UTC

NP-MRD ID

NP0334632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3b,17a,21-Trihydroxypregnenone

Description

3B,17a,21-Trihydroxypregnenone belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Based on a literature review very few articles have been published on 3b,17a,21-Trihydroxypregnenone.

Structure

MOL SDF PDB SMILES InChI

3b,17a,21-Trihydroxypregnenone.mol
  Mrv2104 05252321462D          

 28 31  0  0  0  0            999 V2000
   -2.4157   -1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4157   -0.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7012   -0.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7012   -2.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9867   -1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2723   -2.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4422   -1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4422   -0.8108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1567   -0.3983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9413   -0.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4262    0.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9413    0.6816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7417    1.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3333    2.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1567    0.4267    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1567    1.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4422    0.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2723    0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2723   -0.3983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9867   -0.8108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9867    0.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1301    1.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6890    1.0303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301   -2.0483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7012    0.4267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2723   -1.2233    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4422    0.0142    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1567   -1.2233    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  1  0  0  0
 14 22  1  0  0  0  0
 12 23  1  6  0  0  0
  1 24  1  0  0  0  0
  3 25  2  0  0  0  0
 19 26  1  6  0  0  0
  8 27  1  1  0  0  0
  9 28  1  6  0  0  0
M  END

3b,17a,21-Trihydroxypregnenone.mol
  Mrv2104 05252321462D          

 28 31  0  0  0  0            999 V2000
   -2.4157   -1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4157   -0.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7012   -0.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7012   -2.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9867   -1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2723   -2.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4422   -1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4422   -0.8108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1567   -0.3983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9413   -0.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4262    0.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9413    0.6816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7417    1.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3333    2.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1567    0.4267    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1567    1.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4422    0.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2723    0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2723   -0.3983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9867   -0.8108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9867    0.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1301    1.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6890    1.0303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301   -2.0483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7012    0.4267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2723   -1.2233    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4422    0.0142    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1567   -1.2233    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  1  0  0  0
 14 22  1  0  0  0  0
 12 23  1  6  0  0  0
  1 24  1  0  0  0  0
  3 25  2  0  0  0  0
 19 26  1  6  0  0  0
  8 27  1  1  0  0  0
  9 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0334632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@](O)(CCO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1/C21H32O4/c1-19-7-5-17-15(16(19)6-8-21(19,25)9-10-22)4-3-13-11-14(23)12-18(24)20(13,17)2/h12-13,15-17,22-23,25H,3-11H2,1-2H3/t13?,15-,16-,17-,19-,20-,21-/s2

> <INCHI_KEY>
RJKJQHWLCLYSHD-IXAXXIATNA-N

> <FORMULA>
C21H32O4

> <MOLECULAR_WEIGHT>
348.483

> <EXACT_MASS>
348.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.95129208651872

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3aS,3bS,9aS,9bS,11aS)-1,7-dihydroxy-1-(2-hydroxyethyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,5aH,6H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-9-one

> <JCHEM_LOGP>
2.387887568

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.27511566017067

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.1374621931587985

> <JCHEM_PKA_STRONGEST_BASIC>
-2.413699285728761

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
97.84179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3aS,3bS,9aS,9bS,11aS)-1,7-dihydroxy-1-(2-hydroxyethyl)-9a,11a-dimethyl-2H,3H,3aH,3bH,4H,5H,5aH,6H,9bH,10H,11H-cyclopenta[a]phenanthren-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3b,17a,21-Trihydroxypregnenone.mol                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0      -4.509  -3.053   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.509  -1.513   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.176  -0.743   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.176  -3.823   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.842  -3.053   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.508  -3.823   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.825  -3.053   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.825  -1.513   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.159  -0.743   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.624  -1.219   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.529   0.027   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.624   1.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.251   2.767   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.355   3.823   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.159   0.797   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.159   2.337   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.825   1.567   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.508   0.797   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.508  -0.743   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.842  -1.513   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.842   0.027   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.843   3.425   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.019   1.923   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.843  -3.823   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.176   0.797   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0      -0.508  -2.283   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.825   0.027   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.159  -2.283   0.000  0.00  0.00           H+0
CONECT    1    2    4   24                                                  
CONECT    2    1    3                                                       
CONECT    3    2   20   25                                                  
CONECT    4    1    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19   27                                             
CONECT    9    8   10   15   28                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15   23                                             
CONECT   13   12   14                                                       
CONECT   14   13   22                                                       
CONECT   15   12    9   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    8   20   26                                             
CONECT   20   19    3    5   21                                             
CONECT   21   20                                                            
CONECT   22   14                                                            
CONECT   23   12                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26   19                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₄

Average Mass

348.4830 Da

Monoisotopic Mass

348.23006 Da

IUPAC Name

(1S,3aS,3bS,9aS,9bS,11aS)-1,7-dihydroxy-1-(2-hydroxyethyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,5aH,6H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-9-one

Traditional Name

(1S,3aS,3bS,9aS,9bS,11aS)-1,7-dihydroxy-1-(2-hydroxyethyl)-9a,11a-dimethyl-2H,3H,3aH,3bH,4H,5H,5aH,6H,9bH,10H,11H-cyclopenta[a]phenanthren-9-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@](O)(CCO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C

InChI Identifier

InChI=1/C21H32O4/c1-19-7-5-17-15(16(19)6-8-21(19,25)9-10-22)4-3-13-11-14(23)12-18(24)20(13,17)2/h12-13,15-17,22-23,25H,3-11H2,1-2H3/t13?,15-,16-,17-,19-,20-,21-/s2

InChI Key

RJKJQHWLCLYSHD-IXAXXIATNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

Progestogin-skeleton
21-hydroxysteroid
Pregnane-skeleton
3-hydroxysteroid
1-oxosteroid
Oxosteroid
17-hydroxysteroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Vinylogous acid
Ketone
Enol
Primary alcohol
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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	2.39	ChemAxon
pKa (Strongest Acidic)	6.14	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.84 m³·mol⁻¹	ChemAxon
Polarizability	39.95 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3b,17a,21-Trihydroxypregnenone (NP0334632)

MOL for NP0334632 (3b,17a,21-Trihydroxypregnenone)

3D MOL for NP0334632 (3b,17a,21-Trihydroxypregnenone)

3D SDF for NP0334632 (3b,17a,21-Trihydroxypregnenone)

3D-SDF for NP0334632 (3b,17a,21-Trihydroxypregnenone)

PDB for NP0334632 (3b,17a,21-Trihydroxypregnenone)

3D PDB for NP0334632 (3b,17a,21-Trihydroxypregnenone)

SMILES for NP0334632 (3b,17a,21-Trihydroxypregnenone)

INCHI for NP0334632 (3b,17a,21-Trihydroxypregnenone)

Structure for NP0334632 (3b,17a,21-Trihydroxypregnenone)

3D Structure for NP0334632 (3b,17a,21-Trihydroxypregnenone)