NP-MRD: Showing NP-Card for 4-Methoxy-17beta-estradiol (NP0339089)

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Record Information

Version

2.0

Created at

2024-09-11 19:37:55 UTC

Updated at

2024-09-11 19:37:55 UTC

NP-MRD ID

NP0339089

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Methoxy-17beta-estradiol

Description

4-Methoxy-17beta-estradiol belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. 4-Methoxy-17beta-estradiol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208092D          

 22 25  0  0  1  0            999 V2000
   10.6475  -15.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3654  -15.4108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3723  -14.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6615  -14.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9439  -14.5735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6687  -13.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3867  -12.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0976  -13.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8156  -12.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8227  -12.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5404  -11.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2513  -12.1364    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4029  -11.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0382  -11.8879    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.6560  -11.3412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5173  -12.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0266  -13.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2444  -12.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5263  -13.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5192  -14.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8012  -14.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0904  -14.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 22  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 22  1  0  0  0  0
  9 10  1  0  0  0  0
  9 19  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 12 18  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  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  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339089

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2CCC3C4CC[C@H](O)[C@@]4(C)CCC3C2=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O3/c1-19-10-9-12-11-5-7-16(20)18(22-2)14(11)4-3-13(12)15(19)6-8-17(19)21/h5,7,12-13,15,17,20-21H,3-4,6,8-10H2,1-2H3/t12?,13?,15?,17-,19-/m0/s1

> <INCHI_KEY>
BCWZIZLVBYHFES-BHFCKAAKSA-N

> <FORMULA>
C19H26O3

> <MOLECULAR_WEIGHT>
302.4079

> <EXACT_MASS>
302.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.89470781241338

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(14S,15S)-6-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
3.587830062666667

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.377692236649462

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.337683878037284

> <JCHEM_PKA_STRONGEST_BASIC>
-0.883954578812724

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
86.36789999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(14S,15S)-6-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol

> <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      19.875 -29.525   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      21.215 -28.767   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      21.228 -27.228   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.901 -26.446   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      18.562 -27.204   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      19.915 -24.906   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.255 -24.148   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.582 -24.929   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.922 -24.171   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.936 -22.631   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.275 -21.873   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.602 -22.655   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.885 -21.140   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.071 -22.191   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      29.225 -21.170   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      28.966 -23.444   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.050 -24.683   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.590 -24.193   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.249 -24.952   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.236 -26.492   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.896 -27.251   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.569 -26.469   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   18                                             
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   12   17   19                                                  
CONECT   19    9   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22    3    8   21                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
4-Methoxy-17b-estradiol	Generator
4-Methoxy-17β-estradiol	Generator
3,17beta-Dihydroxy-4-methoxy-1,3,5[10]-estratriene	HMDB
3,4,17beta-Trihydroxy-1,3,5[10]-estratriene 4-methyl ether	HMDB
4-MeOE2	HMDB
4-Methoxy-1,3,5[10]-estratriene-3,17beta-diol	HMDB
4-Methoxy-3,17beta-dihydroxy-1,3,5[10]-estratriene	HMDB
4-Methoxyestradiol	HMDB

Chemical Formula

C₁₉H₂₆O₃

Average Mass

302.4079 Da

Monoisotopic Mass

302.18819 Da

IUPAC Name

(14S,15S)-6-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol

Traditional Name

(14S,15S)-6-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol

CAS Registry Number

Not Available

SMILES

COC1=C2CCC3C4CC[C@H](O)[C@@]4(C)CCC3C2=CC=C1O

InChI Identifier

InChI=1S/C19H26O3/c1-19-10-9-12-11-5-7-16(20)18(22-2)14(11)4-3-13(12)15(19)6-8-17(19)21/h5,7,12-13,15,17,20-21H,3-4,6,8-10H2,1-2H3/t12?,13?,15?,17-,19-/m0/s1

InChI Key

BCWZIZLVBYHFES-BHFCKAAKSA-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 estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens and derivatives

Alternative Parents

Substituents

Estrogen-skeleton
3-hydroxysteroid
17-hydroxysteroid
Hydroxysteroid
Phenanthrene
Tetralin
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Cyclic alcohol
Secondary alcohol
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	3.65	ALOGPS
logP	3.59	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	10.34	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.37 m³·mol⁻¹	ChemAxon
Polarizability	34.89 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029173

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

53481522

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-Methoxy-17beta-estradiol (NP0339089)

MOL for NP0339089 (4-Methoxy-17beta-estradiol)

3D MOL for NP0339089 (4-Methoxy-17beta-estradiol)

3D SDF for NP0339089 (4-Methoxy-17beta-estradiol)

3D-SDF for NP0339089 (4-Methoxy-17beta-estradiol)

PDB for NP0339089 (4-Methoxy-17beta-estradiol)

3D PDB for NP0339089 (4-Methoxy-17beta-estradiol)

SMILES for NP0339089 (4-Methoxy-17beta-estradiol)

INCHI for NP0339089 (4-Methoxy-17beta-estradiol)

Structure for NP0339089 (4-Methoxy-17beta-estradiol)

3D Structure for NP0339089 (4-Methoxy-17beta-estradiol)