NP-MRD: Showing NP-Card for 2-Hydroxyestrone sulfate (NP0339071)

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Record Information

Version

2.0

Created at

2024-09-11 19:33:05 UTC

Updated at

2024-09-11 19:33:05 UTC

NP-MRD ID

NP0339071

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Hydroxyestrone sulfate

Description

2-Hydroxyestrone sulfate belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. 2-Hydroxyestrone sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208082D          

 25 28  0  0  1  0            999 V2000
   15.3146  -12.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7834  -11.4138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3709  -12.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5459  -12.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1334  -11.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5459  -10.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1334   -9.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3084   -9.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8959  -10.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0709  -10.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6584  -11.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8334  -11.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4209  -10.6993    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1353  -10.2868    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.7064  -11.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0084   -9.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0709  -12.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6584  -12.8428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8959  -12.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3084  -11.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3709  -10.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9229  -10.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6766  -10.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5904  -11.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2034  -11.7943    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 21  1  0  0  0  0
  2 24  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 20  1  0  0  0  0
  6  7  1  0  0  0  0
  6 21  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 20  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 17  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 16  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  CHG  1  14  -1
M  END


  Mrv0541 02251208082D          

 25 28  0  0  1  0            999 V2000
   15.3146  -12.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7834  -11.4138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3709  -12.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5459  -12.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1334  -11.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5459  -10.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1334   -9.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3084   -9.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8959  -10.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0709  -10.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6584  -11.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8334  -11.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4209  -10.6993    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1353  -10.2868    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.7064  -11.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0084   -9.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0709  -12.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6584  -12.8428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8959  -12.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3084  -11.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3709  -10.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9229  -10.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6766  -10.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5904  -11.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2034  -11.7943    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 21  1  0  0  0  0
  2 24  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 20  1  0  0  0  0
  6  7  1  0  0  0  0
  6 21  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 20  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 17  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 16  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  CHG  1  14  -1
M  END
> <DATABASE_ID>
NP0339071

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CCC3C(CCC4=C3C=C(O)C(OS([O-])(=O)=O)=C4)C1CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O6S/c1-18-7-6-11-12(14(18)4-5-17(18)20)3-2-10-8-16(24-25(21,22)23)15(19)9-13(10)11/h8-9,11-12,14,19H,2-7H2,1H3,(H,21,22,23)/p-1/t11?,12?,14?,18-/m0/s1

> <INCHI_KEY>
DTMWSKSAMRZGQH-PEDDLLMLSA-M

> <FORMULA>
C18H21O6S

> <MOLECULAR_WEIGHT>
365.421

> <EXACT_MASS>
365.105884094

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.273401370236236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(15S)-4-hydroxy-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl sulfate

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
4.180150366000001

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.547445172363899

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.9028893074543571

> <JCHEM_PKA_STRONGEST_BASIC>
-4.376507922696352

> <JCHEM_POLAR_SURFACE_AREA>
103.73000000000002

> <JCHEM_REFRACTIVITY>
89.93339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(15S)-4-hydroxy-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl sulfate

> <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      28.587 -22.484   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.596 -21.306   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.826 -22.639   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.286 -22.639   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.516 -21.306   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.286 -19.972   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.516 -18.638   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.976 -18.638   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.206 -19.972   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.666 -19.972   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.896 -21.306   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      18.356 -21.306   0.000  0.00  0.00           O+0
HETATM   13  S   UNK     0      17.586 -19.972   0.000  0.00  0.00           S+0
HETATM   14  O   UNK     0      18.919 -19.202   0.000  0.00  0.00           O-1
HETATM   15  O   UNK     0      16.252 -20.742   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      16.816 -18.638   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      20.666 -22.639   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      19.896 -23.973   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      22.206 -22.639   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.976 -21.306   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.826 -19.972   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.856 -18.828   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      29.263 -19.454   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.102 -20.986   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      30.246 -22.016   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21   24                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17   11   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20    5    9   19                                                  
CONECT   21    2    6   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24    2   23   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxyestrone sulfuric acid	Generator
2-Hydroxyestrone sulphate	Generator
2-Hydroxyestrone sulphuric acid	Generator
1,3,5(10)-Triene-2,3-diol-17-one 3-sulfate	HMDB
1,3,5(10)-Triene-2,3-diol-17-one 3-sulphate	HMDB
2,3-Dihydroxyestra-1,3,5(10)-trien-17-one 3-sulfate	HMDB
2,3-Dihydroxyestra-1,3,5(10)-trien-17-one 3-sulphate	HMDB
2HEn-3S	HMDB
Catecholestrogen sulfate	HMDB
Catecholestrogen sulphate	HMDB

Chemical Formula

C₁₈H₂₁O₆S

Average Mass

365.4210 Da

Monoisotopic Mass

365.10588 Da

IUPAC Name

(15S)-4-hydroxy-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl sulfate

Traditional Name

(15S)-4-hydroxy-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl sulfate

CAS Registry Number

Not Available

SMILES

C[C@]12CCC3C(CCC4=C3C=C(O)C(OS([O-])(=O)=O)=C4)C1CCC2=O

InChI Identifier

InChI=1S/C18H22O6S/c1-18-7-6-11-12(14(18)4-5-17(18)20)3-2-10-8-16(24-25(21,22)23)15(19)9-13(10)11/h8-9,11-12,14,19H,2-7H2,1H3,(H,21,22,23)/p-1/t11?,12?,14?,18-/m0/s1

InChI Key

DTMWSKSAMRZGQH-PEDDLLMLSA-M

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 sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Sulfated steroids

Direct Parent

Sulfated steroids

Alternative Parents

Substituents

Sulfated steroid skeleton
Estrane-skeleton
2-hydroxysteroid
Hydroxysteroid
Oxosteroid
17-oxosteroid
Phenanthrene
Arylsulfate
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Ketone
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic anion
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	2.48	ALOGPS
logP	4.18	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	-1.9	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.73 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.93 m³·mol⁻¹	ChemAxon
Polarizability	37.27 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

FDB029153

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

53481500

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Hydroxyestrone sulfate (NP0339071)

MOL for NP0339071 (2-Hydroxyestrone sulfate)

3D MOL for NP0339071 (2-Hydroxyestrone sulfate)

3D SDF for NP0339071 (2-Hydroxyestrone sulfate)

3D-SDF for NP0339071 (2-Hydroxyestrone sulfate)

PDB for NP0339071 (2-Hydroxyestrone sulfate)

3D PDB for NP0339071 (2-Hydroxyestrone sulfate)

SMILES for NP0339071 (2-Hydroxyestrone sulfate)

INCHI for NP0339071 (2-Hydroxyestrone sulfate)

Structure for NP0339071 (2-Hydroxyestrone sulfate)

3D Structure for NP0339071 (2-Hydroxyestrone sulfate)