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Showing NP-Card for Dexamethasone (NP0333810)

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Record Information
Version2.0
Created at2024-09-09 20:39:02 UTC
Updated at2024-09-09 20:39:02 UTC
NP-MRD IDNP0333810
Secondary Accession NumbersNone
Natural Product Identification
Common NameDexamethasone
DescriptionGlucocorticoid with potent antiinflammatory props. Not FDA approved for use in food-producing animals, but may be used illegally Dexamethasone and its derivatives, dexamethasone sodium phosphate and dexamethasone acetate, are synthetic glucocorticoids. It is used for its antiinflammatory or immunosuppressive properties and ability to penetrate the CNS, dexamethasone is used alone to manage cerebral edema and with tobramycin to treat corticosteroid-responsive inflammatory ocular conditions.; Dexamethasone can be used in the context of congenital adrenal hyperplasia, to prevent virilisation of a female fetus. If one or both parents are carriers of mutations to the CYP21 (CYP21A2) gene, the mother may start dexamethasone treatment within 7 weeks of conception. At the 12th week, a chorionic villus sample will determine whether the fetus is male (in which case the dexamethasone is stopped) or female. Subsequent DNA analysis can then reveal whether the female fetus is a carrier of the mutation, in which case dexamethasone treatment must continue until birth. The side-effects for the mother can be severe and the long-term impact on the child is not clear.; Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid hormones. It acts as an anti-inflammatory and immunosuppressant. Its potency is about 20-30 times that of hydrocortisone and 4-5 times of prednisone.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0333810 (Dexamethasone)


  Mrv2104 05242323112D          

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M  END
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3D MOL for NP0333810 (Dexamethasone)

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3D SDF for NP0333810 (Dexamethasone)

  Mrv2104 05242323112D          

 28 31  0  0  0  0            999 V2000
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   -0.3365    0.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1358    0.5367    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5846    0.2731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 19  1  0  0  0  0
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  7 19  1  0  0  0  0
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  8 16  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0333810

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2C3CCC4=CC(=O)C=CC4(C)C3(F)C(O)CC2(C)C1(O)C(=O)CO

> <INCHI_IDENTIFIER>
InChI=1/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3

> <INCHI_KEY>
UREBDLICKHMUKA-UHFFFAOYNA-N

> <FORMULA>
C22H29FO5

> <MOLECULAR_WEIGHT>
392.467

> <EXACT_MASS>
392.199902197

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.009755317475765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9b-fluoro-1,10-dihydroxy-1-(2-hydroxyacetyl)-2,9a,11a-trimethyl-2H,3H,3aH,3bH,4H,5H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one

> <JCHEM_LOGP>
1.6815696796666673

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.482283372225584

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.424778249663545

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3301756738658193

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
102.49289999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
betamethasone

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0333810 (Dexamethasone)
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PDB for NP0333810 (Dexamethasone)
HEADER    PROTEIN                                 24-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-MAY-23         0                                  
HETATM    1  C   UNK     0       6.812   4.048   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.628   1.361   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.068   0.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.682   5.435   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.834   5.164   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.660   1.903   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.144   1.632   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.089   4.389   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.191   4.528   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.404   0.818   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.975   0.326   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.364   3.525   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.675   4.257   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.183   3.351   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.357   3.715   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.873   3.444   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.888   1.089   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.452   1.775   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.151   2.809   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.396   1.996   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.365   2.538   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.936   2.046   0.000  0.00  0.00           C+0
HETATM   23  F   UNK     0       0.253   1.002   0.000  0.00  0.00           F+0
HETATM   24  O   UNK     0       8.491   0.055   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -5.699   3.622   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.105  -0.088   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       7.444   2.952   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.825   0.510   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4    5   13                                                       
CONECT    5    4   15                                                       
CONECT    6    7   14                                                       
CONECT    7    6   19                                                       
CONECT    8   12   16                                                       
CONECT    9   13   14                                                       
CONECT   10   17   20                                                       
CONECT   11   18   24                                                       
CONECT   12    1    8   22                                                  
CONECT   13    4    9   19                                                  
CONECT   14    6    9   25                                                  
CONECT   15    5   16   21                                                  
CONECT   16    8   15   20                                                  
CONECT   17   10   21   26                                                  
CONECT   18   11   22   27                                                  
CONECT   19    2    7   13   21                                             
CONECT   20    3   10   16   22                                             
CONECT   21   15   17   19   23                                             
CONECT   22   12   18   20   28                                             
CONECT   23   21                                                            
CONECT   24   11                                                            
CONECT   25   14                                                            
CONECT   26   17                                                            
CONECT   27   18                                                            
CONECT   28   22                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

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3D PDB for NP0333810 (Dexamethasone)
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SMILES for NP0333810 (Dexamethasone)
CC1CC2C3CCC4=CC(=O)C=CC4(C)C3(F)C(O)CC2(C)C1(O)C(=O)CO
Download
INCHI for NP0333810 (Dexamethasone)
InChI=1/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC22H29FO5
Average Mass392.4670 Da
Monoisotopic Mass392.19990 Da
IUPAC Name9b-fluoro-1,10-dihydroxy-1-(2-hydroxyacetyl)-2,9a,11a-trimethyl-2H,3H,3aH,3bH,4H,5H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
Traditional Namebetamethasone
CAS Registry NumberNot Available
SMILES
CC1CC2C3CCC4=CC(=O)C=CC4(C)C3(F)C(O)CC2(C)C1(O)C(=O)CO
InChI Identifier
InChI=1/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3
InChI KeyUREBDLICKHMUKA-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
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
logP1.68ChemAxon
pKa (Strongest Acidic)12.42ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity102.49 m³·mol⁻¹ChemAxon
Polarizability41.01 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External LinksNot Available
References
General ReferencesNot Available