NP-MRD: Showing NP-Card for Estrone-2,3-quinone (NP0339128)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 19:49:03 UTC

Updated at

2024-09-11 19:49:03 UTC

NP-MRD ID

NP0339128

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Estrone-2,3-quinone

Description

Estrone-2,3-quinone belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Estrone-2,3-quinone is an extremely weak basic (essentially neutral) compound (based on its pKa). Moreover, estrone-3,4-quinone, but not. Tumors may arise in cells covalently damaged by the free radicals or by the quinones and stimulated to proliferate by hormone receptor-mediated.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303262014172D          

 21 24  0  0  1  0            999 V2000
   14.9409  -11.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4096  -11.0361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9971  -11.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1721  -11.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7596  -11.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1721  -10.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7596   -9.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9346   -9.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5221  -10.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6971  -10.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2846  -11.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4596  -11.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6971  -11.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2846  -12.4650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5221  -11.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9346  -11.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9971  -10.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5492   -9.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3029  -10.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2167  -10.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8298  -11.4166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2 17  1  0  0  0  0
  2 20  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 16  1  0  0  0  0
  6  7  1  0  0  0  0
  6 17  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  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  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339128

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CCC3C(CCC4=CC(=O)C(=O)C=C34)C1CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14H,2-7H2,1H3/t11?,12?,14?,18-/m0/s1

> <INCHI_KEY>
WFPLOQDPWXNOST-PEDDLLMLSA-N

> <FORMULA>
C18H20O3

> <MOLECULAR_WEIGHT>
284.3496

> <EXACT_MASS>
284.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.260076818988736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,6-diene-4,5,14-trione

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
3.4277205510000006

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.392798621017317

> <JCHEM_PKA_STRONGEST_BASIC>
-7.459250302087497

> <JCHEM_POLAR_SURFACE_AREA>
51.21

> <JCHEM_REFRACTIVITY>
80.70409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,6-diene-4,5,14-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0      27.890 -21.779   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.898 -20.601   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.128 -21.934   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.588 -21.934   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.818 -20.601   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.588 -19.267   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.818 -17.933   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.278 -17.933   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.508 -19.267   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.968 -19.267   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.198 -20.601   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      17.658 -20.601   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      19.968 -21.934   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      19.198 -23.268   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      21.508 -21.934   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.278 -20.601   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.128 -19.267   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.159 -18.123   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.565 -18.749   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.405 -20.281   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      29.549 -21.311   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17   20                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16    5    9   15                                                  
CONECT   17    2    6   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20    2   19   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Value	Source
Catecholestrogen quinone	HMDB

Chemical Formula

C₁₈H₂₀O₃

Average Mass

284.3496 Da

Monoisotopic Mass

284.14124 Da

IUPAC Name

(15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,6-diene-4,5,14-trione

Traditional Name

(15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,6-diene-4,5,14-trione

CAS Registry Number

Not Available

SMILES

C[C@]12CCC3C(CCC4=CC(=O)C(=O)C=C34)C1CCC2=O

InChI Identifier

InChI=1S/C18H20O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14H,2-7H2,1H3/t11?,12?,14?,18-/m0/s1

InChI Key

WFPLOQDPWXNOST-PEDDLLMLSA-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
2-oxosteroid
Oxosteroid
17-oxosteroid
3-oxosteroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	2.62	ALOGPS
logP	3.43	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.39	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	51.21 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.7 m³·mol⁻¹	ChemAxon
Polarizability	31.26 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

HMDB0012941

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029219

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

53481559

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Estrone-2,3-quinone (NP0339128)

MOL for NP0339128 (Estrone-2,3-quinone)

3D MOL for NP0339128 (Estrone-2,3-quinone)

3D SDF for NP0339128 (Estrone-2,3-quinone)

3D-SDF for NP0339128 (Estrone-2,3-quinone)

PDB for NP0339128 (Estrone-2,3-quinone)

3D PDB for NP0339128 (Estrone-2,3-quinone)

SMILES for NP0339128 (Estrone-2,3-quinone)

INCHI for NP0339128 (Estrone-2,3-quinone)

Structure for NP0339128 (Estrone-2,3-quinone)

3D Structure for NP0339128 (Estrone-2,3-quinone)