NP-MRD: Showing NP-Card for Estrone (NP0001273)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:39:12 UTC

NP-MRD ID

NP0001273

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Estrone

Description

Estrone is a major mammalian estrogen. The conversion of the natural C19 steroids, testosterone and androstenedione into estrone is dependent on a complex key reaction catalyzed by the cytochrome P450 aromatase (EC 1.14.14.1, Unspecific monooxygenase), which is expressed in many tissues of the adult human (e.G. Ovary, fat tissue), but not in the liver. The ovaries after menopause continue to produce androstenedione and testosterone in significant amounts and these androgens are converted in fat, muscle, and skin into estrone. When women between the ages of 45 and 64 years have prophylactic oophorectomy (when hysterectomy is performed for benign disease to prevent the development of ovarian cancer), evidence suggests that oophorectomy increases the subsequent risk of coronary heart disease (CHD) and osteoporosis. Whereas 14,000 women die of ovarian cancer every year nearly 490,000 women die of heart disease and 48,000 women die within 1 year after hip fracture. Therefore, the decision to perform prophylactic oophorectomy should be approached with great caution for the majority of women who are at low risk of developing ovarian cancer. Steroid sulfatase (EC 3.1.6.2, STS) hydrolyzes steroid sulfates, such as estrone sulfate to estrone which can be converted to steroids with potent estrogenic properties, that is, estradiol; STS activity is much higher in breast tumors and high levels of STS mRNA expression in tumors are associated with a poor prognosis. The biological roles of estrogens in tumorigenesis are certainly different between the endometrium and breast, although both are considered "estrogen-dependent tissues". 17Beta-hydroxysteroid dehydrogenases (EC 1.1.1.62, 17-HSDs) are enzymes involved in the formation of active sex steroids. Estrone is interconverted by two enzymes 17-HSD types. Type 1 converts estrone to estradiol and Type 2 catalyzes the reverse reaction. (PMID: 17653961 , 17513923 , 17470679 , 17464097 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000145
     RDKit          3D
Estrone
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.4507   -0.5081    1.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688   -0.7693    0.2945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4724   -1.9846    0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -1.8188   -0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4582   -0.4674   -0.5702 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9112   -0.2898   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7331   -1.3689   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1032   -1.3188   -0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531   -0.1422    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359   -0.0339    0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    0.9413    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623    0.8859    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194    2.0889    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2899    1.9703   -0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3464    0.6585    0.0993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7086    0.4491   -0.4120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7368    1.4652   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0294    0.6604   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6284   -0.7660   -0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2643   -1.7118   -0.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -0.5144    2.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0253   -1.4059    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976    0.3544    1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5683   -2.6410    0.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981   -2.5892   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267   -2.5095   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129   -2.2068    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3109   -0.2918   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3511   -2.3230   -0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435   -2.1691   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3381   -0.2918    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2439    1.8818    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4140    2.1096    1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1419    3.0224    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461    2.0060   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    2.8274    0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    0.5735    1.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6998    0.2039   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650    2.2630   -0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7170    1.9745    0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3575    0.8387   -1.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7938    0.9471    0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  1
 16 38  1  6
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
M  END


  Mrv1652310301918522D          

 23 26  0  0  0  0            999 V2000
10001.446810001.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1679 9998.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0195 9998.9603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.731110000.1943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.4468 9998.9603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0192 9999.7809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0192 9998.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7337 9998.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7337 9999.3684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.732510001.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.018010000.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5939 9999.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8795 9999.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8795 9998.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5939 9998.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3084 9998.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3084 9999.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.231610000.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.447010000.6136    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4470 9999.7886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2316 9999.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.716510000.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.486510001.6532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11  6  1  0  0  0  0
  6  3  1  6  0  0  0
  9  4  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
 14  2  1  0  0  0  0
  6 17  1  0  0  0  0
 16  7  1  0  0  0  0
 18 19  1  0  0  0  0
 18 22  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
 18 23  2  0  0  0  0
 20  5  1  6  0  0  0
  9 20  1  0  0  0  0
 10 19  1  0  0  0  0
 19  1  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0001273

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1

> <INCHI_KEY>
DNXHEGUUPJUMQT-CBZIJGRNSA-N

> <FORMULA>
C18H22O2

> <MOLECULAR_WEIGHT>
270.3661

> <EXACT_MASS>
270.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.24404121393373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

> <ALOGPS_LOGP>
4.03

> <JCHEM_LOGP>
4.309029034000001

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.957534565528498

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.32695754200012

> <JCHEM_PKA_STRONGEST_BASIC>
-5.448299376893847

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
79.0824

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000145
     RDKit          3D
Estrone
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.4507   -0.5081    1.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688   -0.7693    0.2945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4724   -1.9846    0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -1.8188   -0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4582   -0.4674   -0.5702 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9112   -0.2898   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7331   -1.3689   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1032   -1.3188   -0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531   -0.1422    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359   -0.0339    0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    0.9413    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623    0.8859    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194    2.0889    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2899    1.9703   -0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3464    0.6585    0.0993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7086    0.4491   -0.4120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7368    1.4652   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0294    0.6604   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6284   -0.7660   -0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2643   -1.7118   -0.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -0.5144    2.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0253   -1.4059    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976    0.3544    1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5683   -2.6410    0.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981   -2.5892   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267   -2.5095   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129   -2.2068    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3109   -0.2918   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3511   -2.3230   -0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435   -2.1691   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3381   -0.2918    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2439    1.8818    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4140    2.1096    1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1419    3.0224    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461    2.0060   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    2.8274    0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    0.5735    1.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6998    0.2039   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650    2.2630   -0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7170    1.9745    0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3575    0.8387   -1.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7938    0.9471    0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  1
 16 38  1  6
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
M  END

HEADER    PROTEIN                                 30-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-OCT-19         0                                  
HETATM    1  C   UNK     0    8669.3678669.359   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8661.3808663.167   0.000  0.00  0.00           O+0
HETATM    3  H   UNK     0    8666.7038664.726   0.000  0.00  0.00           H+0
HETATM    4  H   UNK     0    8668.0318667.029   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8669.3678664.726   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    8666.7038666.258   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8666.7038663.178   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.0368663.947   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8668.0368665.488   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.0348668.582   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.7008667.812   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.0428666.256   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.7088665.486   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.7088663.946   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.0428663.176   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.3768663.946   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.3768665.486   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.8328668.288   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8669.3688667.812   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.3688666.272   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8670.8328665.796   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8671.7378667.042   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8671.3088669.753   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   14                                                            
CONECT    3    6                                                            
CONECT    4    9                                                            
CONECT    5   20                                                            
CONECT    6    9   11    3   17                                             
CONECT    7    8   16                                                       
CONECT    8    7    9                                                       
CONECT    9    6    8    4   20                                             
CONECT   10   11   19                                                       
CONECT   11   10    6                                                       
CONECT   12   13   17                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15    2                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17    7                                                  
CONECT   17   16   12    6                                                  
CONECT   18   19   22   23                                                  
CONECT   19   18   20   10    1                                             
CONECT   20   19   21    5    9                                             
CONECT   21   20   22                                                       
CONECT   22   18   21                                                       
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0000145
HETATM    1  C1  UNL     1      -2.451  -0.508   1.787  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.269  -0.769   0.294  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.472  -1.985   0.055  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.037  -1.819  -0.232  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.458  -0.467  -0.570  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.911  -0.290  -0.313  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.733  -1.369  -0.557  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.103  -1.319  -0.353  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.653  -0.142   0.110  1.00  0.00           C  
HETATM   10  O1  UNL     1       6.036  -0.034   0.335  1.00  0.00           O  
HETATM   11  C10 UNL     1       3.826   0.941   0.355  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.462   0.886   0.150  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.619   2.089   0.432  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.290   1.970  -0.322  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.346   0.659   0.099  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.709   0.449  -0.412  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.737   1.465  -0.154  1.00  0.00           C  
HETATM   18  C17 UNL     1      -4.029   0.660  -0.368  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.628  -0.766  -0.290  1.00  0.00           C  
HETATM   20  O2  UNL     1      -4.264  -1.712  -0.626  1.00  0.00           O  
HETATM   21  H1  UNL     1      -1.505  -0.514   2.337  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.025  -1.406   2.163  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.098   0.354   1.982  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.568  -2.641   0.973  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.998  -2.589  -0.744  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.227  -2.509  -1.089  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.613  -2.207   0.610  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.311  -0.292  -1.660  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.351  -2.323  -0.924  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.744  -2.169  -0.547  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.338  -0.292   1.285  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.244   1.882   0.723  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.414   2.110   1.516  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.142   3.022   0.166  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.446   2.006  -1.401  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.325   2.827   0.018  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.227   0.574   1.179  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.700   0.204  -1.496  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.665   2.263  -0.946  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.717   1.975   0.804  1.00  0.00           H  
HETATM   41  H21 UNL     1      -4.358   0.839  -1.429  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.794   0.947   0.364  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   16   19
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   15   28
CONECT    6    7    7   12
CONECT    7    8   29
CONECT    8    9    9   30
CONECT    9   10   11
CONECT   10   31
CONECT   11   12   12   32
CONECT   12   13
CONECT   13   14   33   34
CONECT   14   15   35   36
CONECT   15   16   37
CONECT   16   17   38
CONECT   17   18   39   40
CONECT   18   19   41   42
CONECT   19   20   20
END

HMDB0000145
     RDKit          3D
Estrone
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.4507   -0.5081    1.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688   -0.7693    0.2945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4724   -1.9846    0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -1.8188   -0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4582   -0.4674   -0.5702 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9112   -0.2898   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7331   -1.3689   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1032   -1.3188   -0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531   -0.1422    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359   -0.0339    0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    0.9413    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623    0.8859    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6194    2.0889    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2899    1.9703   -0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3464    0.6585    0.0993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7086    0.4491   -0.4120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7368    1.4652   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0294    0.6604   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6284   -0.7660   -0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2643   -1.7118   -0.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -0.5144    2.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0253   -1.4059    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976    0.3544    1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5683   -2.6410    0.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981   -2.5892   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2267   -2.5095   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129   -2.2068    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3109   -0.2918   -1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3511   -2.3230   -0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435   -2.1691   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3381   -0.2918    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2439    1.8818    0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4140    2.1096    1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1419    3.0224    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4461    2.0060   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    2.8274    0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269    0.5735    1.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6998    0.2039   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6650    2.2630   -0.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7170    1.9745    0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3575    0.8387   -1.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7938    0.9471    0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  6
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  1
 16 38  1  6
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-Hydroxy-1,3,5(10)-estratrien-17-one	ChEBI
Follicular hormone	ChEBI
Folliculin	ChEBI
Oestrone	ChEBI
(+)-Estrone	HMDB
1,3,5(10)-Estratrien-3-ol-17-one	HMDB
3-Hydroxy-17-keto-estra-1,3,5-triene	HMDB
3-Hydroxyestra-1,3,5(10)-trien-17-one	HMDB
3-Hydroxyestra-1,3,5(10)-triene-17-one	HMDB
3-Hydroxyoestra-1,3,5(10)-trien-17-one	HMDB
D1,3,5(10)-Estratrien-3-ol-17-one	HMDB
Estrone, (+-)-isomer	HMDB
Hyrex brand OF estrone	HMDB
Estrone, (9 beta)-isomer	HMDB
Estrovarin	HMDB
Kestrone	HMDB
Wehgen	HMDB
Estrone, (8 alpha)-isomer	HMDB
Hauck brand OF estrone	HMDB
Unigen	HMDB
Vortech brand OF estrone	HMDB

Chemical Formula

C₁₈H₂₂O₂

Average Mass

270.3661 Da

Monoisotopic Mass

270.16198 Da

IUPAC Name

(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

Traditional Name

(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

CAS Registry Number

53-16-7

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3

InChI Identifier

InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1

InChI Key

DNXHEGUUPJUMQT-CBZIJGRNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Malus pumila	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Olea europaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Perilla frutescens	LOTUS Database	35616633
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phoenix dactylifera	KNApSAcK Database	22123792
Prunus armeniaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Psidium guajava	LOTUS Database	35616633
Punica granatum	KNApSAcK Database	22123792
Solanum glaucophyllum	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Hydroxysteroid
17-oxosteroid
Oxosteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Ketone
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

17-oxo steroid (CHEBI:17263 )
3-hydroxy steroid (CHEBI:17263 )
estrane (C00468 )
C18 steroids (estrogens) and derivatives (C00468 )
Estrane and derivatives (C00468 )
Estrogens (C00468 )
C18 steroids (estrogens) and derivatives (LMST02010004 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	258 - 260 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.03 mg/mL	Not Available
LogP	3.13	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	0.0039 g/L	ALOGPS
logP	4.03	ALOGPS
logP	4.31	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.08 m³·mol⁻¹	ChemAxon
Polarizability	31.24 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000145

DrugBank ID

DB00655

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17263

Good Scents ID

rw1369041

References

General References

Pfeiffer E, Graf E, Gerstner S, Metzler M: Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? Mol Nutr Food Res. 2006 Apr;50(4-5):385-9. [PubMed:16598814 ]
Czernik PJ, Little JM, Barone GW, Raufman JP, Radominska-Pandya A: Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. Drug Metab Dispos. 2000 Oct;28(10):1210-6. [PubMed:10997942 ]
Kuhl H, Wiegratz I: Can 19-nortestosterone derivatives be aromatized in the liver of adult humans? Are there clinical implications? Climacteric. 2007 Aug;10(4):344-53. [PubMed:17653961 ]
Parker WH, Broder MS, Liu Z, Shoupe D, Farquhar C, Berek JS: Ovarian conservation at the time of hysterectomy for benign disease. Clin Obstet Gynecol. 2007 Jun;50(2):354-61. [PubMed:17513923 ]
Stanway SJ, Delavault P, Purohit A, Woo LW, Thurieau C, Potter BV, Reed MJ: Steroid sulfatase: a new target for the endocrine therapy of breast cancer. Oncologist. 2007 Apr;12(4):370-4. [PubMed:17470679 ]
Ito K: Hormone replacement therapy and cancers: the biological roles of estrogen and progestin in tumorigenesis are different between the endometrium and breast. Tohoku J Exp Med. 2007 May;212(1):1-12. [PubMed:17464097 ]

Showing NP-Card for Estrone (NP0001273)

MOL for NP0001273 (Estrone)

3D MOL for NP0001273 (Estrone)

3D SDF for NP0001273 (Estrone)

3D-SDF for NP0001273 (Estrone)

PDB for NP0001273 (Estrone)

3D PDB for NP0001273 (Estrone)

SMILES for NP0001273 (Estrone)

INCHI for NP0001273 (Estrone)

Structure for NP0001273 (Estrone)

3D Structure for NP0001273 (Estrone)