NP-MRD: Showing NP-Card for Estrogen (NP0333857)

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Record Information

Version

2.0

Created at

2024-09-09 20:58:32 UTC

Updated at

2024-09-09 20:58:33 UTC

NP-MRD ID

NP0333857

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Estrogen

Description

A steroid hormone that stimulates or controls the development and maintenance of female sex characteristics in mammals by binding to oestrogen receptors. The oestrogens are named for their importance in the oestrous cycle. (ChEBI). Estrogen is found in date and apricot.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533007131513462D          

 20 21  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 15 10  1  0  0  0  0
 16 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17  3  1  0  0  0  0
 17 13  1  0  0  0  0
 18  4  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  2  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333857

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C(=C(\CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+

> <INCHI_KEY>
RGLYKWWBQGJZGM-ISLYRVAYSA-N

> <FORMULA>
C18H20O2

> <MOLECULAR_WEIGHT>
268.356

> <EXACT_MASS>
268.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.683957430730576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
5.193882748

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.231491526289268

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.629198524189572

> <JCHEM_PKA_STRONGEST_BASIC>
-6.456792337140983

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
83.2406

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
estrogen

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1   17                                                       
CONECT    4    2   18                                                       
CONECT    5    9   13                                                       
CONECT    6   10   13                                                       
CONECT    7   11   14                                                       
CONECT    8   12   14                                                       
CONECT    9    5   15                                                       
CONECT   10    6   15                                                       
CONECT   11    7   16                                                       
CONECT   12    8   16                                                       
CONECT   13    5    6   17                                                  
CONECT   14    7    8   18                                                  
CONECT   15    9   10   19                                                  
CONECT   16   11   12   20                                                  
CONECT   17    3   13   18                                                  
CONECT   18    4   14   17                                                  
CONECT   19   15                                                            
CONECT   20   16                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
(e)-3,4-Bis(4-hydroxyphenyl)-3-hexene	ChEBI
(e)-4,4'-(1,2-Diethyl-1,2-ethenediyl)bisphenol	ChEBI
4,4'-Dihydroxy-alpha,beta-diethylstilbene	ChEBI
alpha,Alpha'-diethyl-(e)-4,4'-stilbenediol	ChEBI
DES	ChEBI
Diethylstilbestrolum	ChEBI
Dietilestilbestrol	ChEBI
Distilbene	ChEBI
trans-4,4'-(1,2-Diethyl-1,2-ethenediyl)bisphenol	ChEBI
trans-Diethylstilbesterol	ChEBI
trans-Diethylstilbestrol	ChEBI
trans-Diethylstilboesterol	ChEBI
Stilbestrol	Kegg
4,4'-Dihydroxy-a,b-diethylstilbene	Generator
4,4'-Dihydroxy-α,β-diethylstilbene	Generator
a,Alpha'-diethyl-(e)-4,4'-stilbenediol	Generator
Α,alpha'-diethyl-(e)-4,4'-stilbenediol	Generator
Tampovagan	MeSH
co Pharma brand OF diethylstilbestrol	MeSH
Diethylstilbestrol, (Z)-isomer	MeSH
Gerda brand OF diethylstilbestrol	MeSH
APS brand OF diethylstilbestrol	MeSH
Apstil	MeSH
Agostilben	MeSH
Stilbene estrogen	MeSH
CO-Pharma brand OF diethylstilbestrol	MeSH
Estrogen, stilbene	MeSH
Diethylstilbestrol, disodium salt	MeSH

Chemical Formula

C₁₈H₂₀O₂

Average Mass

268.3560 Da

Monoisotopic Mass

268.14633 Da

IUPAC Name

4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

Traditional Name

estrogen

CAS Registry Number

Not Available

SMILES

CC\C(=C(\CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+

InChI Key

RGLYKWWBQGJZGM-ISLYRVAYSA-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 stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Phenylpropane
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

polyphenol (CHEBI:41922 )

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	4.62	ALOGPS
logP	5.19	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	8.63	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.24 m³·mol⁻¹	ChemAxon
Polarizability	30.68 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB006560

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C07620

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diethylstilbestrol

METLIN ID

Not Available

PubChem Compound

448537

PDB ID

Not Available

ChEBI ID

41922

Good Scents ID

Not Available

References

General References

Dobrydneva Y, Williams RL, Katzenellenbogen JA, Ratz PH, Blackmore PF: Diethylstilbestrol and tetrahydrochrysenes are calcium channel blockers in human platelets: relationship to the stilbene pharmacophore. Thromb Res. 2003 Apr 15;110(1):23-31. doi: 10.1016/s0049-3848(03)00110-5. [PubMed:12877905 ]
Clemons J, Glode LM, Gao D, Flaig TW: Low-dose diethylstilbestrol for the treatment of advanced prostate cancer. Urol Oncol. 2013 Feb;31(2):198-204. doi: 10.1016/j.urolonc.2010.12.004. Epub 2011 Jul 27. [PubMed:21795073 ]
Authors unspecified: Diethylstilbestrol. Rep Carcinog. 2011;12:159-61. [PubMed:21852823 ]
Grenader T, Plotkin Y, Gips M, Cherny N, Gabizon A: Diethylstilbestrol for the treatment of patients with castration-resistant prostate cancer: retrospective analysis of a single institution experience. Oncol Rep. 2014 Jan;31(1):428-34. doi: 10.3892/or.2013.2852. Epub 2013 Nov 14. [PubMed:24247716 ]
Stoeckelhuber M, Noegel AA, Eckerskorn C, Kohler J, Rieger D, Schleicher M: Structure/function studies on the pH-dependent actin-binding protein hisactophilin in Dictyostelium mutants. J Cell Sci. 1996 Jul;109 ( Pt 7):1825-35. doi: 10.1242/jcs.109.7.1825. [PubMed:8832405 ]

Showing NP-Card for Estrogen (NP0333857)

MOL for NP0333857 (Estrogen)

3D MOL for NP0333857 (Estrogen)

3D SDF for NP0333857 (Estrogen)

3D-SDF for NP0333857 (Estrogen)

PDB for NP0333857 (Estrogen)

3D PDB for NP0333857 (Estrogen)

SMILES for NP0333857 (Estrogen)

INCHI for NP0333857 (Estrogen)

Structure for NP0333857 (Estrogen)

3D Structure for NP0333857 (Estrogen)