NP-MRD: Showing NP-Card for 19-Oic-deoxycorticosterone (NP0339069)

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Record Information

Version

2.0

Created at

2024-09-11 19:32:32 UTC

Updated at

2024-09-11 19:32:32 UTC

NP-MRD ID

NP0339069

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19-Oic-deoxycorticosterone

Description

19-Oic-deoxycorticosterone, also known as deoxycorticosterone-19-oic or 19-oic-DOC, 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-Oic-deoxycorticosterone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208082D          

 26 29  0  0  1  0            999 V2000
   14.7938  -17.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6656  -18.1424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9429  -17.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2373  -18.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2534  -18.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9760  -19.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9921  -20.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2859  -20.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5637  -20.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8575  -20.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1348  -20.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4292  -20.7011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1188  -19.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8250  -19.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5472  -19.4219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2761  -18.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7635  -18.0416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5538  -18.3280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6816  -18.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4711  -19.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9426  -18.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4451  -17.8717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8174  -17.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3429  -16.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6390  -16.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9861  -16.2471    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 19  1  0  0  0  0
  2 22  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 19  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  1  0  0  0  0
 16 18  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END


  Mrv0541 02251208082D          

 26 29  0  0  1  0            999 V2000
   14.7938  -17.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6656  -18.1424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9429  -17.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2373  -18.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2534  -18.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9760  -19.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9921  -20.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2859  -20.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5637  -20.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8575  -20.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1348  -20.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4292  -20.7011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1188  -19.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8250  -19.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5472  -19.4219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2761  -18.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7635  -18.0416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5538  -18.3280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6816  -18.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4711  -19.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9426  -18.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4451  -17.8717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8174  -17.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3429  -16.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6390  -16.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9861  -16.2471    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 19  1  0  0  0  0
  2 22  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 19  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  1  0  0  0  0
 16 18  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339069

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O5/c1-20-8-7-16-14(15(20)4-5-17(20)18(24)11-22)3-2-12-10-13(23)6-9-21(12,16)19(25)26/h10,14-17,22H,2-9,11H2,1H3,(H,25,26)/t14?,15?,16?,17-,20+,21-/m1/s1

> <INCHI_KEY>
RUPOMAOZPOVHQZ-TTYNRZOGSA-N

> <FORMULA>
C21H28O5

> <MOLECULAR_WEIGHT>
360.444

> <EXACT_MASS>
360.193674006

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
38.96521453878634

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <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-carboxylic acid

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
2.5230489536666663

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.864718530037528

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.249824156986669

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2953178742425218

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
96.12469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e-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-carboxylic acid

> <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      27.615 -32.344   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.376 -33.866   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.027 -33.123   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.710 -33.918   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.740 -35.458   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.089 -36.201   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.119 -37.741   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.800 -38.537   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.452 -37.793   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.134 -38.590   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.785 -37.846   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      19.468 -38.642   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      20.755 -36.306   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.073 -35.510   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.421 -36.254   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.915 -34.919   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      23.825 -33.678   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      21.567 -34.212   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      27.406 -35.406   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.879 -35.852   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      29.760 -34.589   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.831 -33.361   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      29.526 -31.862   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      28.640 -30.603   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      31.059 -31.725   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      31.707 -30.328   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   19                                                  
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   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    2    6   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22    2   21   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
21-Hydroxy-3,20-dioxopregn-4-en-19-Oate	HMDB
21-Hydroxy-3,20-dioxopregn-4-en-19-Oic acid	HMDB
21-Hydroxy-3,20-dioxopregn-4-en-19-Oic acid anion	HMDB
19-Oic-11-deoxycorticosterone	MeSH
19-Oic-21-hydroxy-4-pregnen-3,20-dione	MeSH
Deoxycorticosterone-19-oic	MeSH
19-Oic-DOC	MeSH
(2S,14S,15S)-14-(2-Hydroxyacetyl)-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-2-carboxylate	Generator
19-Oic-deoxycorticosterone	MeSH

Chemical Formula

C₂₁H₂₈O₅

Average Mass

360.4440 Da

Monoisotopic Mass

360.19367 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H28O5/c1-20-8-7-16-14(15(20)4-5-17(20)18(24)11-22)3-2-12-10-13(23)6-9-21(12,16)19(25)26/h10,14-17,22H,2-9,11H2,1H3,(H,25,26)/t14?,15?,16?,17-,20+,21-/m1/s1

InChI Key

RUPOMAOZPOVHQZ-TTYNRZOGSA-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
Cyclic ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	2.83	ALOGPS
logP	2.52	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.12 m³·mol⁻¹	ChemAxon
Polarizability	38.97 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

HMDB0012613

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029151

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

53481498

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 19-Oic-deoxycorticosterone (NP0339069)

MOL for NP0339069 (19-Oic-deoxycorticosterone)

3D MOL for NP0339069 (19-Oic-deoxycorticosterone)

3D SDF for NP0339069 (19-Oic-deoxycorticosterone)

3D-SDF for NP0339069 (19-Oic-deoxycorticosterone)

PDB for NP0339069 (19-Oic-deoxycorticosterone)

3D PDB for NP0339069 (19-Oic-deoxycorticosterone)

SMILES for NP0339069 (19-Oic-deoxycorticosterone)

INCHI for NP0339069 (19-Oic-deoxycorticosterone)

Structure for NP0339069 (19-Oic-deoxycorticosterone)

3D Structure for NP0339069 (19-Oic-deoxycorticosterone)