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Showing NP-Card for 18-Hydroxy-11-dehydrotetrahydrocorticosterone (NP0339199)

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Record Information
Version2.0
Created at2024-09-11 20:22:00 UTC
Updated at2024-09-11 20:22:00 UTC
NP-MRD IDNP0339199
Secondary Accession NumbersNone
Natural Product Identification
Common Name18-Hydroxy-11-dehydrotetrahydrocorticosterone
Description18-Hydroxy-11-dehydrotetrahydrocorticosterone, also known as 3-hydroxy-9(Z)-octadecenoylcarnitine, 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. 18-Hydroxy-11-dehydrotetrahydrocorticosterone is a major urinary metabolite of 18-hydroxycorticosterone and is used to monitor 18-hydroxycorticosterone secretion rate. 18-Hydroxy-11-dehydrotetrahydrocorticosterone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339199 (18-Hydroxy-11-dehydrotetrahydrocorticosterone)


  Mrv0541 02251208172D          

 26 29  0  0  1  0            999 V2000
   12.8960  -13.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9074  -13.8937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1871  -13.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4789  -13.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4905  -14.7391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2101  -15.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9189  -14.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6392  -15.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3481  -14.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3365  -13.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6162  -13.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6048  -12.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8845  -12.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3136  -12.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0340  -12.6267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0454  -13.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8331  -13.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3087  -13.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8145  -12.3606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9744  -11.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7552  -11.2851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3534  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5133  -10.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1668  -11.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5282  -11.2904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7820  -15.1614    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  7  1  0  0  0  0
  2 11  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 26  1  6  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
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
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 15 19  1  0  0  0  0
 15 24  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
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 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
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3D MOL for NP0339199 (18-Hydroxy-11-dehydrotetrahydrocorticosterone)

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3D SDF for NP0339199 (18-Hydroxy-11-dehydrotetrahydrocorticosterone)

  Mrv0541 02251208172D          

 26 29  0  0  1  0            999 V2000
   12.8960  -13.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9074  -13.8937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1871  -13.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4789  -13.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4905  -14.7391    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2101  -15.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9189  -14.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6392  -15.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3481  -14.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3365  -13.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6162  -13.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6048  -12.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8845  -12.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3136  -12.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0340  -12.6267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0454  -13.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8331  -13.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3087  -13.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8145  -12.3606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9744  -11.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7552  -11.2851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3534  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5133  -10.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1668  -11.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5282  -11.2904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7820  -15.1614    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  7  1  0  0  0  0
  2 11  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 26  1  6  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
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 19  1  0  0  0  0
 15 24  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339199

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@@H](O)CC1CCC1C3CC[C@H](C(=O)CO)[C@@]3(CO)CC(=O)C21

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h12-16,19,22-24H,2-11H2,1H3/t12?,13-,14?,15?,16-,19?,20+,21-/m1/s1

> <INCHI_KEY>
UQRPWWKJWZFNAE-HATFOLNYSA-N

> <FORMULA>
C21H32O5

> <MOLECULAR_WEIGHT>
364.4758

> <EXACT_MASS>
364.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.3771177937666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5R,14S,15R)-5-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
0.9656681880000002

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.080406489435422

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.836275522771423

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569619583776276

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
97.05089999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5R,14S,15R)-5-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339199 (18-Hydroxy-11-dehydrotetrahydrocorticosterone)
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PDB for NP0339199 (18-Hydroxy-11-dehydrotetrahydrocorticosterone)
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      24.073 -24.395   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.094 -25.935   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.749 -25.184   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.427 -25.972   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.449 -27.513   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.792 -28.264   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.115 -27.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.460 -28.227   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.783 -27.439   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.761 -25.898   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.417 -25.147   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.396 -23.607   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      24.051 -22.855   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      26.719 -22.818   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.063 -23.570   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.085 -25.110   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.555 -25.566   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.443 -24.306   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.520 -23.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.819 -21.562   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      31.276 -21.066   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      28.660 -20.548   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      28.958 -19.038   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      28.311 -22.050   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      27.119 -21.075   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      20.126 -28.301   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11    2   10   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   19   24                                             
CONECT   16   10   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   15   18   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   15   25                                                       
CONECT   25   24                                                            
CONECT   26    5                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

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3D PDB for NP0339199 (18-Hydroxy-11-dehydrotetrahydrocorticosterone)
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SMILES for NP0339199 (18-Hydroxy-11-dehydrotetrahydrocorticosterone)
C[C@]12CC[C@@H](O)CC1CCC1C3CC[C@H](C(=O)CO)[C@@]3(CO)CC(=O)C21
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INCHI for NP0339199 (18-Hydroxy-11-dehydrotetrahydrocorticosterone)
InChI=1S/C21H32O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h12-16,19,22-24H,2-11H2,1H3/t12?,13-,14?,15?,16-,19?,20+,21-/m1/s1
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Synonyms
ValueSource
18-Hydroxy-11-dehydrotetrahydrocorticosteroneMeSH
18-Hydroxytetrahydro-11-dehydrocorticosteroneMeSH
HTDHCMeSH
Chemical FormulaC21H32O5
Average Mass364.4758 Da
Monoisotopic Mass364.22497 Da
IUPAC Name(2S,5R,14S,15R)-5-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one
Traditional Name(2S,5R,14S,15R)-5-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one
CAS Registry NumberNot Available
SMILES
C[C@]12CC[C@@H](O)CC1CCC1C3CC[C@H](C(=O)CO)[C@@]3(CO)CC(=O)C21
InChI Identifier
InChI=1S/C21H32O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h12-16,19,22-24H,2-11H2,1H3/t12?,13-,14?,15?,16-,19?,20+,21-/m1/s1
InChI KeyUQRPWWKJWZFNAE-HATFOLNYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot 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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassHydroxysteroids  
Direct Parent21-hydroxysteroids  
Alternative Parents
Substituents
  • Progestogin-skeleton
    • 

  • 21-hydroxysteroid
    • 

  • 20-oxosteroid
    • 

  • Pregnane-skeleton
    • 

  • 18-hydroxysteroid
    • 

  • 3-hydroxysteroid
    • 

  • 11-oxosteroid
    • 

  • Oxosteroid
    • 

  • 3-alpha-hydroxysteroid
    • 

  • Cyclic alcohol
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Secondary alcohol
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Primary alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.66ALOGPS
logP0.97ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.05 m³·mol⁻¹ChemAxon
Polarizability40.38 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013157  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029313  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481635  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available