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Showing NP-Card for Epiestradiol (NP0333942)

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Record Information
Version2.0
Created at2024-09-09 21:21:54 UTC
Updated at2024-09-09 21:21:54 UTC
NP-MRD IDNP0333942
Secondary Accession NumbersNone
Natural Product Identification
Common NameEpiestradiol
Description17A-estradiol is found in the estrogen patch. The estrogen patch is a delivery system for estradiol used as hormone replacement therapy to treat the symptoms of menopause, such as hot flashes and vaginal dryness, and to prevent osteoporosis. Originally marketed as Vivelle (Novartis), it was discontinued in 2003 and reintroduced in a smaller form as Vivelle-Dot. Although the estrogen is given transdermally rather than in the standard oral tablets, the estrogen patch carries similar risks and benefits as more conventional forms of estrogen-only hormone replacement therapy.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0333942 (Epiestradiol)


  Mrv2104 05242323542D          

 20 23  0  0  0  0            999 V2000
    0.1073    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596    1.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    0.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    0.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2  4  1  0  0  0  0
  2 11  1  0  0  0  0
  3  5  1  0  0  0  0
  3 12  2  0  0  0  0
  4 15  1  0  0  0  0
  5 13  2  0  0  0  0
  6  7  1  0  0  0  0
  6 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  9 18  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
M  END
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3D MOL for NP0333942 (Epiestradiol)

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3D SDF for NP0333942 (Epiestradiol)

  Mrv2104 05242323542D          

 20 23  0  0  0  0            999 V2000
    0.1073    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596    1.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    0.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    0.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2  4  1  0  0  0  0
  2 11  1  0  0  0  0
  3  5  1  0  0  0  0
  3 12  2  0  0  0  0
  4 15  1  0  0  0  0
  5 13  2  0  0  0  0
  6  7  1  0  0  0  0
  6 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  9 18  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333942

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3C(CCC4=CC(O)=CC=C34)C1CCC2O

> <INCHI_IDENTIFIER>
InChI=1/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3

> <INCHI_KEY>
VOXZDWNPVJITMN-UHFFFAOYNA-N

> <FORMULA>
C18H24O2

> <MOLECULAR_WEIGHT>
272.388

> <EXACT_MASS>
272.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.04291268651912

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-diol

> <JCHEM_LOGP>
3.745501328333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.37769223665565

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.327060716263132

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8839974156894889

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
79.90469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
estradiol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0333942 (Epiestradiol)
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PDB for NP0333942 (Epiestradiol)
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       0.200   0.373   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.950   5.197   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.929   1.666   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.434   4.926   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.413   1.394   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.179   4.152   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.095   3.288   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.381   0.852   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.865   0.581   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.459   4.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.943   4.020   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.452   3.114   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.420   2.572   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.904   2.301   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.911   3.478   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.395   3.207   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.667   1.809   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.872   1.759   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.968   3.385   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.612   0.593   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    4   11                                                       
CONECT    3    5   12                                                       
CONECT    4    2   15                                                       
CONECT    5    3   13                                                       
CONECT    6    7   16                                                       
CONECT    7    6   17                                                       
CONECT    8    9   14                                                       
CONECT    9    8   18                                                       
CONECT   10   11   12                                                       
CONECT   11    2   10   13                                                  
CONECT   12    3   10   19                                                  
CONECT   13    5   11   14                                                  
CONECT   14    8   13   15                                                  
CONECT   15    4   14   16                                                  
CONECT   16    6   15   18                                                  
CONECT   17    7   18   20                                                  
CONECT   18    1    9   16   17                                             
CONECT   19   12                                                            
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

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3D PDB for NP0333942 (Epiestradiol)
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SMILES for NP0333942 (Epiestradiol)
CC12CCC3C(CCC4=CC(O)=CC=C34)C1CCC2O
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INCHI for NP0333942 (Epiestradiol)
InChI=1/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC18H24O2
Average Mass272.3880 Da
Monoisotopic Mass272.17763 Da
IUPAC Name11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-diol
Traditional Nameestradiol
CAS Registry NumberNot Available
SMILES
CC12CCC3C(CCC4=CC(O)=CC=C34)C1CCC2O
InChI Identifier
InChI=1/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3
InChI KeyVOXZDWNPVJITMN-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassEstrane steroids  
Direct ParentEstrogens and derivatives  
Alternative Parents
Substituents
  • Estrogen-skeleton
    • 

  • 17-hydroxysteroid
    • 

  • Hydroxysteroid
    • 

  • 3-hydroxysteroid
    • 

  • Phenanthrene
    • 

  • Tetralin
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
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
logP3.75ChemAxon
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.9 m³·mol⁻¹ChemAxon
Polarizability32.04 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link17α-Estradiol  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Sneitz N, Vahermo M, Mosorin J, Laakkonen L, Poirier D, Finel M: Regiospecificity and stereospecificity of human UDP-glucuronosyltransferases in the glucuronidation of estriol, 16-epiestriol, 17-epiestriol, and 13-epiestradiol. Drug Metab Dispos. 2013 Mar;41(3):582-91. doi: 10.1124/dmd.112.049072. Epub 2013  Jan 3. [PubMed:23288867  ] 
  2. Manevski N, Troberg J, Svaluto-Moreolo P, Dziedzic K, Yli-Kauhaluoma J, Finel M: Albumin stimulates the activity of the human UDP-glucuronosyltransferases 1A7, 1A8, 1A10, 2A1 and 2B15, but the effects are enzyme and substrate dependent. PLoS One. 2013;8(1):e54767. doi: 10.1371/journal.pone.0054767. Epub 2013 Jan 23. [PubMed:23372764  ] 
  3. Sneitz N, Krishnan K, Covey DF, Finel M: Glucuronidation of the steroid enantiomers ent-17beta-estradiol, ent-androsterone and ent-etiocholanolone by the human UDP-glucuronosyltransferases. J Steroid Biochem Mol Biol. 2011 Nov;127(3-5):282-8. doi:  10.1016/j.jsbmb.2011.08.008. Epub 2011 Aug 27. [PubMed:21899827  ] 
  4. Itaaho K, Mackenzie PI, Ikushiro S, Miners JO, Finel M: The configuration of the 17-hydroxy group variably influences the glucuronidation of beta-estradiol and epiestradiol by human UDP-glucuronosyltransferases. Drug Metab Dispos. 2008 Nov;36(11):2307-15. doi: 10.1124/dmd.108.022731. Epub  2008 Aug 21. [PubMed:18719240  ]