NP-MRD: Showing NP-Card for 17a-Estradiol (NP0001300)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:22:21 UTC

NP-MRD ID

NP0001300

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17a-Estradiol

Description

17A-estradiol is found in the estrogen patch. The estrogen patch is a delivery system for estradiol used as hormone replacement therapy to treat the symptoms of menopause, such as hot flashes and vaginal dryness, and to prevent osteoporosis. Originally marketed as Vivelle (Novartis), it was discontinued in 2003 and reintroduced in a smaller form as Vivelle-Dot. Although the estrogen is given transdermally rather than in the standard oral tablets, the estrogen patch carries similar risks and benefits as more conventional forms of estrogen-only hormone replacement therapy. 17A-Estradiol is found to be associated with glutaryl-CoA dehydrogenase deficiency (GDHD), which is an inborn error of metabolism.

Structure

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

HMDB0000429
     RDKit          3D
17alpha-Estradiol
 44 47  0  0  0  0  0  0  0  0999 V2000
   -2.1765    1.9777    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399    0.5640    0.6965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3563    0.4055    1.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118    0.5640    1.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582   -0.2295    0.6232 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0858   -0.1391    0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9256    0.2084    1.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.2922    1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518    0.0242    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130    0.1003   -0.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0155   -0.3290   -1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6530   -0.4037   -0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.7851   -1.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.2648   -1.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    0.1306   -0.6041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5175   -0.3933   -0.3326 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4818   -0.3359   -1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8227   -0.1626   -0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268    0.0318    0.7348 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6013   -1.2165    1.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3706    2.6057    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    1.9463   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1633    2.4116    0.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285   -0.5750    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050    1.1796    2.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872    0.2977    2.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3419    1.6447    1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4043   -1.3092    0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953    0.4376    2.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9775    0.5631    2.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7942   -0.7025   -0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4891   -0.5308   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -0.3902   -2.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -1.9012   -2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -1.0781   -2.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960    0.5580   -2.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    1.2590   -0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -1.3797    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5177   -1.3494   -1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908    0.3911   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2786    0.7632   -1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851   -1.0388   -0.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2691    0.7448    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661   -1.8550    0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  1  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  1
  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  6
 16 38  1  1
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  1
 20 44  1  0
M  END

17a-Estradiol.mol
  Mrv1652304202019422D          

 23 26  0  0  0  0            999 V2000
   -2.0637   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782   -1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -0.5198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5086   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2933   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933    0.9727    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5482    1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086    0.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5086    1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6348   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    0.3052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  1  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  0  0  0  0
  6 20  2  0  0  0  0
 19 21  1  6  0  0  0
  9 22  1  1  0  0  0
 10 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0001300

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1

> <INCHI_KEY>
VOXZDWNPVJITMN-SFFUCWETSA-N

> <FORMULA>
C18H24O2

> <MOLECULAR_WEIGHT>
272.382

> <EXACT_MASS>
272.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.927942457761795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.745501328333334

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.37769223665565

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.327060716263132

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8839974156894889

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
79.90469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.13e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000429
     RDKit          3D
17alpha-Estradiol
 44 47  0  0  0  0  0  0  0  0999 V2000
   -2.1765    1.9777    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399    0.5640    0.6965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3563    0.4055    1.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118    0.5640    1.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582   -0.2295    0.6232 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0858   -0.1391    0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9256    0.2084    1.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.2922    1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518    0.0242    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130    0.1003   -0.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0155   -0.3290   -1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6530   -0.4037   -0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.7851   -1.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.2648   -1.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    0.1306   -0.6041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5175   -0.3933   -0.3326 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4818   -0.3359   -1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8227   -0.1626   -0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268    0.0318    0.7348 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6013   -1.2165    1.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3706    2.6057    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    1.9463   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1633    2.4116    0.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285   -0.5750    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050    1.1796    2.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872    0.2977    2.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3419    1.6447    1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4043   -1.3092    0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953    0.4376    2.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9775    0.5631    2.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7942   -0.7025   -0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4891   -0.5308   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -0.3902   -2.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -1.9012   -2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -1.0781   -2.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960    0.5580   -2.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    1.2590   -0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -1.3797    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5177   -1.3494   -1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908    0.3911   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2786    0.7632   -1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851   -1.0388   -0.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2691    0.7448    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661   -1.8550    0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  1  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  1
  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  6
 16 38  1  1
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  1
 20 44  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 17a-Estradiol.mol                                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      -3.852  -2.510   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.186  -3.280   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.852  -0.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.519  -0.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.519  -3.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.185  -2.510   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.149  -3.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.483  -2.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.483  -0.970   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.816  -0.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.281  -0.676   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.186   0.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.281   1.816   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.757   3.280   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.816   1.340   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.816   2.880   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.483   2.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.149   1.340   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.149  -0.200   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.185  -0.970   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       0.149  -1.740   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.483   0.570   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.816  -1.740   0.000  0.00  0.00           H+0
CONECT    1    2    3    5                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3   20                                                       
CONECT    5    1    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   19   22                                             
CONECT   10    9   11   15   23                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   10   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    9   20   21                                             
CONECT   20   19    4    6                                                  
CONECT   21   19                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0000429
HETATM    1  C1  UNL     1      -2.176   1.978   0.179  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.140   0.564   0.697  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.356   0.405   1.949  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.112   0.564   1.771  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.658  -0.230   0.623  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.086  -0.139   0.440  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.926   0.208   1.463  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.312   0.292   1.272  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.852   0.024   0.044  1.00  0.00           C  
HETATM   10  O1  UNL     1       6.213   0.100  -0.168  1.00  0.00           O  
HETATM   11  C10 UNL     1       4.015  -0.329  -1.004  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.653  -0.404  -0.787  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.807  -0.785  -1.932  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.422  -0.265  -1.903  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.145   0.131  -0.604  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.517  -0.393  -0.333  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.482  -0.336  -1.434  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.823  -0.163  -0.760  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.527   0.032   0.735  1.00  0.00           C  
HETATM   20  O2  UNL     1      -3.601  -1.216   1.349  1.00  0.00           O  
HETATM   21  H1  UNL     1      -1.371   2.606   0.613  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.109   1.946  -0.924  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.163   2.412   0.461  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.629  -0.575   2.405  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.705   1.180   2.684  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.587   0.298   2.753  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.342   1.645   1.626  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.404  -1.309   0.840  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.595   0.438   2.466  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.978   0.563   2.067  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.794  -0.703  -0.029  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.489  -0.531  -1.954  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.314  -0.390  -2.861  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.832  -1.901  -2.094  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.247  -1.078  -2.322  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.296   0.558  -2.671  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.217   1.259  -0.591  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.472  -1.380   0.144  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.518  -1.349  -1.932  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.291   0.391  -2.231  1.00  0.00           H  
HETATM   41  H21 UNL     1      -4.279   0.763  -1.167  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.485  -1.039  -0.876  1.00  0.00           H  
HETATM   43  H23 UNL     1      -4.269   0.745   1.132  1.00  0.00           H  
HETATM   44  H24 UNL     1      -4.166  -1.855   0.864  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   43
CONECT   20   44
END

HMDB0000429
     RDKit          3D
17alpha-Estradiol
 44 47  0  0  0  0  0  0  0  0999 V2000
   -2.1765    1.9777    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399    0.5640    0.6965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3563    0.4055    1.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118    0.5640    1.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582   -0.2295    0.6232 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0858   -0.1391    0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9256    0.2084    1.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3124    0.2922    1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518    0.0242    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130    0.1003   -0.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0155   -0.3290   -1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6530   -0.4037   -0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.7851   -1.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.2648   -1.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    0.1306   -0.6041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5175   -0.3933   -0.3326 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4818   -0.3359   -1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8227   -0.1626   -0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268    0.0318    0.7348 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6013   -1.2165    1.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3706    2.6057    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087    1.9463   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1633    2.4116    0.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285   -0.5750    2.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050    1.1796    2.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872    0.2977    2.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3419    1.6447    1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4043   -1.3092    0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953    0.4376    2.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9775    0.5631    2.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7942   -0.7025   -0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4891   -0.5308   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -0.3902   -2.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -1.9012   -2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -1.0781   -2.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960    0.5580   -2.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    1.2590   -0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720   -1.3797    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5177   -1.3494   -1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908    0.3911   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2786    0.7632   -1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851   -1.0388   -0.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2691    0.7448    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1661   -1.8550    0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  1  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  1
  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  6
 16 38  1  1
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  1
 20 44  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(17alpha)-Estra-1,3,5(10)-triene-3,17-diol	ChEBI
1,3,5-Estratriene-3,17alpha-diol	ChEBI
13beta-Methyl-1,3,5(10)-gonatriene-3,17alpha-diol	ChEBI
17-Epiestradiol	ChEBI
17alpha-Oestradiol	ChEBI
3,17alpha-Dihydroxyestra-1,3,5(10)-triene	ChEBI
3,17alpha-Dihydroxyoestra-1,3,5(10)-triene	ChEBI
Alfatradiol	ChEBI
Alfatradiolum	ChEBI
alpha-Estradiol	ChEBI
Epiestradiol	ChEBI
Epiestrol	ChEBI
Estra-1,3,5(10)-triene-3,17alpha-diol	ChEBI
Estra-1,3,5(10)trien-3,17alpha-diol	ChEBI
Estradiol-17alpha	ChEBI
Oestra-1,3,5(10)-triene-3,17alpha-diol	ChEBI
(17a)-Estra-1,3,5(10)-triene-3,17-diol	Generator
(17Α)-estra-1,3,5(10)-triene-3,17-diol	Generator
1,3,5-Estratriene-3,17a-diol	Generator
1,3,5-Estratriene-3,17α-diol	Generator
13b-Methyl-1,3,5(10)-gonatriene-3,17a-diol	Generator
13Β-methyl-1,3,5(10)-gonatriene-3,17α-diol	Generator
17a-Oestradiol	Generator
17Α-oestradiol	Generator
3,17a-Dihydroxyestra-1,3,5(10)-triene	Generator
3,17Α-dihydroxyestra-1,3,5(10)-triene	Generator
3,17a-Dihydroxyoestra-1,3,5(10)-triene	Generator
3,17Α-dihydroxyoestra-1,3,5(10)-triene	Generator
a-Estradiol	Generator
Α-estradiol	Generator
Estra-1,3,5(10)-triene-3,17a-diol	Generator
Estra-1,3,5(10)-triene-3,17α-diol	Generator
Estra-1,3,5(10)trien-3,17a-diol	Generator
Estra-1,3,5(10)trien-3,17α-diol	Generator
Estradiol-17a	Generator
Estradiol-17α	Generator
Oestra-1,3,5(10)-triene-3,17a-diol	Generator
Oestra-1,3,5(10)-triene-3,17α-diol	Generator
17a-Estradiol	Generator
17Α-estradiol	Generator
3,17-Dihydroxyestratriene	HMDB
17alpha-Estradiol	KEGG

Chemical Formula

C₁₈H₂₄O₂

Average Mass

272.3820 Da

Monoisotopic Mass

272.17763 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

57-91-0

SMILES

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

InChI Identifier

InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1

InChI Key

VOXZDWNPVJITMN-SFFUCWETSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, 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	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, 252 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	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, 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	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, 101 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	¹H NMR Spectrum (1D, 900 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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Animalia

Plantae

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
17-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

17alpha-hydroxy steroid (CHEBI:17160 )
3-hydroxy steroid (CHEBI:17160 )
estradiol (CHEBI:17160 )
C18 steroids (estrogens) and derivatives (C02537 )
Estrane and derivatives (C02537 )
C18 steroids (estrogens) and derivatives (LMST02010029 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	216 - 219 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0039 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	3.57	ALOGPS
logP	3.75	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.9 m³·mol⁻¹	ChemAxon
Polarizability	31.93 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

HMDB0000429

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB112198

KNApSAcK ID

Not Available

Chemspider ID

61840

KEGG Compound ID

C02537

BioCyc ID

CPD-351

BiGG ID

Not Available

Wikipedia Link

17%CE%B1-Estradiol

METLIN ID

5418

PubChem Compound

68570

PDB ID

Not Available

ChEBI ID

17160

Good Scents ID

Not Available

References

General References

Corbier P, Roffi J, Rhoda J, Valens M: [Female sex behavior of male rats castrated at birth and given female sex hormones: effects of hour of castration]. C R Seances Acad Sci III. 1981 Nov 23;293(11):649-54. [PubMed:6800584 ]
Vic P, Garcia M, Andre J, Humeau C, Rochefort H: [Early effect of estradiol on ultrastructure of chromatin in the endometrium and hormone-dependent mammary tumors]. C R Acad Sci Hebd Seances Acad Sci D. 1978 Jul 17;287(3):141-4. [PubMed:100250 ]
Salat-Baroux J, Scemama-Kestenberg H, Couturier JY, Firmin C, Agnes E, Levy G, Vuillard E: [Postovulatory hormones in plasma, peritoneal and follicular compartments]. J Gynecol Obstet Biol Reprod (Paris). 1982;11(4):447-56. [PubMed:6292281 ]
Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637. [PubMed:17852390 ]
Colazo MG, Ambrose DJ, Kastelic JP, Small JA: Comparison of 2 enzyme immunoassays and a radioimmunoassay for measurement of progesterone concentrations in bovine plasma, skim milk, and whole milk. Can J Vet Res. 2008 Jan;72(1):32-6. [PubMed:18214159 ]

Showing NP-Card for 17a-Estradiol (NP0001300)

MOL for NP0001300 (17a-Estradiol)

3D MOL for NP0001300 (17a-Estradiol)

3D SDF for NP0001300 (17a-Estradiol)

3D-SDF for NP0001300 (17a-Estradiol)

PDB for NP0001300 (17a-Estradiol)

3D PDB for NP0001300 (17a-Estradiol)

SMILES for NP0001300 (17a-Estradiol)

INCHI for NP0001300 (17a-Estradiol)

Structure for NP0001300 (17a-Estradiol)

3D Structure for NP0001300 (17a-Estradiol)