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Showing NP-Card for Estrone sulfate (NP0334067)

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Record Information
Version2.0
Created at2024-09-09 22:00:53 UTC
Updated at2024-09-09 22:00:53 UTC
NP-MRD IDNP0334067
Secondary Accession NumbersNone
Natural Product Identification
Common NameEstrone sulfate
DescriptionEstrone sulfate is a sulfated estrone derivative. Estrone sulfate acts as a long-lived reservoir that can be converted as needed to the more active estradiol (from estrone via 17 beta-hydroxysteroid dehydrogenase). Estrone Sulfate (E1S) is the most abundant circulating estrogen in non-pregnant women as well as normal men. Estrone is primarily synthesized from estrone sulfate. Estrone is an estrogenic hormone secreted by the ovaries and adipose tissues. Estrone is one of the three estrogens found in humans. The other two are estriol and estradiol. Estrone is the least prevalent of the three. Estradiol plays a critical role on reproductive and sexual functioning in women and it also affects other organs including the bones. Estriol is an estrogen that is prevalent primarily during pregnancy. [HMDB]
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334067 (Estrone sulfate)


  Mrv2104 05252300332D          

 24 27  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
   -0.8637    0.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9005    3.3652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3961    2.3090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8443    2.8696    0.0000 O   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
    5.6202    2.5893    0.0000 S   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 23  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 19  2  0  0  0  0
 20 24  1  0  0  0  0
 21 24  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
Download

3D MOL for NP0334067 (Estrone sulfate)

Download
3D SDF for NP0334067 (Estrone sulfate)

  Mrv2104 05252300332D          

 24 27  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
   -0.8637    0.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9005    3.3652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3961    2.3090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8443    2.8696    0.0000 O   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
    5.6202    2.5893    0.0000 S   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 23  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 19  2  0  0  0  0
 20 24  1  0  0  0  0
 21 24  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334067

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3C(CCC4=CC(OS(O)(=O)=O)=CC=C34)C1CCC2=O

> <INCHI_IDENTIFIER>
InChI=1/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)

> <INCHI_KEY>
JKKFKPJIXZFSSB-UHFFFAOYNA-N

> <FORMULA>
C18H22O5S

> <MOLECULAR_WEIGHT>
350.43

> <EXACT_MASS>
350.118794982

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
36.451118263893115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{11a-methyl-1-oxo-2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl}oxidanesulfonic acid

> <JCHEM_LOGP>
3.8337156876666674

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.7480068663945283

> <JCHEM_PKA_STRONGEST_BASIC>
-7.475652910099836

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
89.07419999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
estrogenic substances

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0334067 (Estrone sulfate)
Download
PDB for NP0334067 (Estrone sulfate)
HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-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      -1.612   0.593   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.014   6.282   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      11.939   4.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.043   5.357   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.968   3.385   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0      10.491   4.833   0.000  0.00  0.00           S+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   23                                                  
CONECT   13    5   11   14                                                  
CONECT   14    8   13   15                                                  
CONECT   15    4   14   16                                                  
CONECT   16    6   15   18                                                  
CONECT   17    7   18   19                                                  
CONECT   18    1    9   16   17                                             
CONECT   19   17                                                            
CONECT   20   24                                                            
CONECT   21   24                                                            
CONECT   22   24                                                            
CONECT   23   12   24                                                       
CONECT   24   20   21   22   23                                             
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

Download
3D PDB for NP0334067 (Estrone sulfate)
Download
SMILES for NP0334067 (Estrone sulfate)
CC12CCC3C(CCC4=CC(OS(O)(=O)=O)=CC=C34)C1CCC2=O
Download
INCHI for NP0334067 (Estrone sulfate)
InChI=1/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)
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View in JSmol
Synonyms
ValueSource
Estrone sulfuric acidGenerator
Estrone sulphateGenerator
Estrone sulphuric acidGenerator
Chemical FormulaC18H22O5S
Average Mass350.4300 Da
Monoisotopic Mass350.11879 Da
IUPAC Name{11a-methyl-1-oxo-2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl}oxidanesulfonic acid
Traditional Nameestrogenic substances
CAS Registry NumberNot Available
SMILES
CC12CCC3C(CCC4=CC(OS(O)(=O)=O)=CC=C34)C1CCC2=O
InChI Identifier
InChI=1/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)
InChI KeyJKKFKPJIXZFSSB-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 sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassSulfated steroids  
Direct ParentSulfated steroids  
Alternative Parents
Substituents
  • Sulfated steroid skeleton
    • 

  • Estrane-skeleton
    • 

  • 17-oxosteroid
    • 

  • Oxosteroid
    • 

  • Phenanthrene
    • 

  • Arylsulfate
    • 

  • Tetralin
    • 

  • Benzenoid
    • 

  • Sulfuric acid ester
    • 

  • Sulfuric acid monoester
    • 

  • Sulfate-ester
    • 

  • Organic sulfuric acid or derivatives
    • 

  • Ketone
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
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
logP3.83ChemAxon
pKa (Strongest Acidic)-1.7ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.07 m³·mol⁻¹ChemAxon
Polarizability36.45 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 LinkEstrone sulfate  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Bone C, Squires EJ: Hepatic Gene Expression and Metabolite Profiles of Androstenone and Skatole Relative to Plasma Estrone Sulfate Levels in Boars. Biomolecules. 2024 Jul 15;14(7):850. doi: 10.3390/biom14070850. [PubMed:39062564  ] 
  2. Balasubramonian B, Selcer KW: Steroid sulfatase in mouse liver and testis: Characterization, ontogeny and localization. Steroids. 2024 Oct;210:109483. doi: 10.1016/j.steroids.2024.109483. Epub 2024 Jul  23. [PubMed:39053631  ] 
  3. Sinokki A, Miinalainen A, Kiander W, Kidron H: Preincubation-dependent inhibition of organic anion transporting polypeptide 2B1. Eur J Pharm Sci. 2024 Sep 1;200:106852. doi: 10.1016/j.ejps.2024.106852. Epub  2024 Jul 15. [PubMed:39019347  ] 
  4. Hetemaki N, Robciuc A, Vihma V, Haanpaa M, Hamalainen E, Tikkanen MJ, Mikkola TS, Savolainen-Peltonen H: Adipose Tissue Sex Steroids in Postmenopausal Women with and without Menopausal Hormone Therapy. J Clin Endocrinol Metab. 2024 Jul 10:dgae458. doi: 10.1210/clinem/dgae458. [PubMed:38986008  ] 
  5. Frederiksen H, Johannsen TH, Andersen SE, Petersen JH, Busch AS, Ljubicic ML, Fischer MB, Upners EN, Hagen CP, Main KM, Aksglaede L, Jorgensen N, Lund Karhus L, Linneberg A, Andersson AM, Fluck CE, Juul A: Sex- and age-specific reference intervals of 16 steroid metabolites quantified simultaneously by LC-MS/MS in sera from 2458 healthy subjects aged 0 to 77 years. Clin Chim Acta. 2024 Aug 15;562:119852. doi: 10.1016/j.cca.2024.119852. Epub 2024  Jul 6. [PubMed:38977173  ] 
  6. Kulkarni CP, Yang J, Koleske ML, Lara G, Alam K, Raw A, Rege B, Zhao L, Lu D, Zhang L, Yu LX, Lionberger RA, Giacomini KM, Kroetz DL, Yee SW: Effect of Antioxidants in Medicinal Products on Intestinal Drug Transporters. Pharmaceutics. 2024 May 10;16(5):647. doi: 10.3390/pharmaceutics16050647. [PubMed:38794309  ] 
  7. Yu Z, You G: Topotecan and Ginkgolic Acid Inhibit the Expression and Transport Activity of Human Organic Anion Transporter 3 by Suppressing SUMOylation of the Transporter. Pharmaceutics. 2024 May 9;16(5):638. doi: 10.3390/pharmaceutics16050638. [PubMed:38794300  ] 
  8. Wang X, Zhang Y, Peng J, Zhang H, Jiang T, Zhang Z, Yin T, Su X, Zhang T, Shen L, He S, Wang X, Li D, Yue X, Ji D, Zhang D, Dong R, Zou W, Liang D, Liu Y, Du Y, Zhang Z, Cao Y, Liang C, Ji D: Association Between Exposure to Multiple Toxic Metals in Follicular Fluid and the Risk of PCOS Among Infertile Women: The Mediating Effect of Metabolic Markers. Biol Trace Elem Res. 2024 May 24. doi: 10.1007/s12011-024-04236-y. [PubMed:38789898  ] 
  9. Won JY, Louis JM, Roh ES, Cha SH, Han JH: Functional characterization of Clonorchis sinensis choline transporter. Parasites Hosts Dis. 2023 Nov;61(4):428-438. doi: 10.3347/PHD.23082. Epub 2023  Nov 28. [PubMed:38043538  ] 
  10. Singh A, Kinnebrew G, Hsu PC, Weng DY, Song MA, Reisinger SA, McElroy JP, Keller-Hamilton B, Ferketich AK, Freudenheim JL, Shields PG: Untargeted Metabolomics and Body Mass in Adolescents: A Cross-Sectional and Longitudinal Analysis. Metabolites. 2023 Jul 30;13(8):899. doi: 10.3390/metabo13080899. [PubMed:37623843  ] 
  11. Zhang S, Li J, Li Y, Jiang L, Zhao Y, Jiang X, Zhang X, Shi W: Assimilation behaviors and metabolite formations of estrone sulfate sodium (E1-3S) and 17beta-estradiol-3-O-sulfate sodium (E2-3S) in the wheat. J Environ Manage. 2023 Nov 1;345:118666. doi: 10.1016/j.jenvman.2023.118666. Epub  2023 Jul 26. [PubMed:37506444  ] 
  12. Cao N, Wang Y, Bao B, Wang M, Li J, Dang W, Hua B, Song L, Li H, Li W: 12,13-diHOME and noradrenaline are associated with the occurrence of acute myocardial infarction in patients with type 2 diabetes mellitus. Diabetol Metab Syndr. 2023 Jun 29;15(1):142. doi: 10.1186/s13098-023-01115-9. [PubMed:37386486  ]