NP-MRD: Showing NP-Card for 19-Oxo-deoxycorticosterone (NP0339070)

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Record Information

Version

2.0

Created at

2024-09-11 19:32:47 UTC

Updated at

2024-09-11 19:32:48 UTC

NP-MRD ID

NP0339070

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19-Oxo-deoxycorticosterone

Description

19-Oxo-deoxycorticosterone 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. 19-Oxo-deoxycorticosterone is an extremely weak basic (essentially neutral) compound (based on its pKa). 2) That potassium secretion mediated by aldoster-one-type I receptor interactions in discrete nephron target segments can be influenced by a steroid-sensitive potassium-recycling system in a more distal nephron site. It is possible, however, that 19-nor-deoxycorticosterone is formed at peripheral sites from the oxygenated deoxycorticosterone precursors.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208082D          

 25 28  0  0  1  0            999 V2000
   14.4507  -18.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3422  -19.3368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.6104  -18.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9145  -19.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9504  -20.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6823  -20.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7182  -21.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0228  -21.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2910  -21.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5951  -21.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8633  -21.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1680  -21.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8273  -20.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5232  -20.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2551  -20.6665    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1826  -19.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4671  -19.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3782  -20.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1729  -20.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6283  -19.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1146  -19.0481    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4387  -18.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9322  -17.5988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2557  -18.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5660  -17.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  2 21  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 15  1  0  0  0  0
  6  7  1  0  0  0  0
  6 18  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 15  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END


  Mrv0541 02251208082D          

 25 28  0  0  1  0            999 V2000
   14.4507  -18.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3422  -19.3368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.6104  -18.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9145  -19.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9504  -20.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6823  -20.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7182  -21.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0228  -21.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2910  -21.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5951  -21.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8633  -21.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1680  -21.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8273  -20.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5232  -20.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2551  -20.6665    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1826  -19.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4671  -19.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3782  -20.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1729  -20.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6283  -19.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1146  -19.0481    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4387  -18.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9322  -17.5988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2557  -18.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5660  -17.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  2 21  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 15  1  0  0  0  0
  6  7  1  0  0  0  0
  6 18  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 15  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339070

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CCC3C(CCC4=CC(=O)CC[C@]34C=O)C1CC[C@@H]2C(=O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O4/c1-20-8-7-17-15(16(20)4-5-18(20)19(25)11-22)3-2-13-10-14(24)6-9-21(13,17)12-23/h10,12,15-18,22H,2-9,11H2,1H3/t15?,16?,17?,18-,20+,21-/m1/s1

> <INCHI_KEY>
PDNIPWXQYQYCSU-RJPFGDFGSA-N

> <FORMULA>
C21H28O4

> <MOLECULAR_WEIGHT>
344.4446

> <EXACT_MASS>
344.198759384

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.10330345913816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,14S,15S)-14-(2-hydroxyacetyl)-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-2-carbaldehyde

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
2.364432701333334

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.28815712931711

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.86471012998819

> <JCHEM_PKA_STRONGEST_BASIC>
-3.29531787424248

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
95.19929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,14S,15S)-14-(2-hydroxyacetyl)-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-2-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      26.975 -34.569   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.772 -36.095   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.406 -35.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.107 -36.212   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.174 -37.751   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.540 -38.462   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.607 -40.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.309 -40.827   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.943 -40.116   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.644 -40.944   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.278 -40.233   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      18.980 -41.059   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      20.211 -38.694   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.510 -37.866   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.876 -38.577   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.741 -36.818   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      21.405 -35.991   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      26.839 -37.634   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.323 -38.045   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.173 -36.762   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.214 -35.556   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.819 -34.066   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      27.873 -32.851   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      30.344 -33.854   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      30.923 -32.428   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18   21                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15    5    9   14   16                                             
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    2    6   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21    2   20   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
21-Hydroxy-19-oxopregn-4-ene-3,20-dione	HMDB
19-oxo-Deoxycorticosterone	MeSH
21-Hydroxy-4-pregnen-3,19,20-trione	MeSH

Chemical Formula

C₂₁H₂₈O₄

Average Mass

344.4446 Da

Monoisotopic Mass

344.19876 Da

IUPAC Name

(2S,14S,15S)-14-(2-hydroxyacetyl)-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-2-carbaldehyde

Traditional Name

(2S,14S,15S)-14-(2-hydroxyacetyl)-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-2-carbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@]12CCC3C(CCC4=CC(=O)CC[C@]34C=O)C1CC[C@@H]2C(=O)CO

InChI Identifier

InChI=1S/C21H28O4/c1-20-8-7-17-15(16(20)4-5-18(20)19(25)11-22)3-2-13-10-14(24)6-9-21(13,17)12-23/h10,12,15-18,22H,2-9,11H2,1H3/t15?,16?,17?,18-,20+,21-/m1/s1

InChI Key

PDNIPWXQYQYCSU-RJPFGDFGSA-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 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
20-oxosteroid
19-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Ketone
Cyclic ketone
Primary alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Aldehyde
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	2.57	ALOGPS
logP	2.36	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.2 m³·mol⁻¹	ChemAxon
Polarizability	38.1 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

HMDB0012614

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029152

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

53481499

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 19-Oxo-deoxycorticosterone (NP0339070)

MOL for NP0339070 (19-Oxo-deoxycorticosterone)

3D MOL for NP0339070 (19-Oxo-deoxycorticosterone)

3D SDF for NP0339070 (19-Oxo-deoxycorticosterone)

3D-SDF for NP0339070 (19-Oxo-deoxycorticosterone)

PDB for NP0339070 (19-Oxo-deoxycorticosterone)

3D PDB for NP0339070 (19-Oxo-deoxycorticosterone)

SMILES for NP0339070 (19-Oxo-deoxycorticosterone)

INCHI for NP0339070 (19-Oxo-deoxycorticosterone)

Structure for NP0339070 (19-Oxo-deoxycorticosterone)

3D Structure for NP0339070 (19-Oxo-deoxycorticosterone)