Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0648)
Drug Name
Estrone
Synonyms
Endofolliculina; Estron; Estrone-A; Estrugenone; Estrusol; Femidyn; Folikrin; Folipex; Folisan; Follestrine; Follestrol; Folliculine; Aquacrine; Cristallovar; Crystogen; Destrone; Disynformon; Follicunodis; Glandubolin; Hiestrone; Hormestrin; Hormovarine; Kestrone; Ketodestrin; Ketohydroxyestrin; Ketohydroxyoestrin; Kolpon; Menagen; Menformon; Mestronaq; OESTRONE; Oestrin; Oestroform; Oestronum; Oestroperos; Ovifollin; Perlatan; Solliculin; Theelin; Thelykinin; Thynestron; Wynestron; estrone; estrovarin; follicular hormone; folliculin; 53-16-7; Unden
Indication Menopausal disorder [ICD11: GA30] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 270.4 Topological Polar Surface Area 37.3
Heavy Atom Count 20 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
5870
PubChem SID
2687 ; 3751 ; 613807 ; 841396 ; 855919 ; 3133155 ; 7847135 ; 7979191 ; 8144215 ; 8153628 ; 11466942 ; 11468062 ; 11486713 ; 14714953 ; 14750534 ; 14774967 ; 17405076 ; 24278427 ; 24715020 ; 24870303 ; 24894399 ; 26512283 ; 26751561 ; 26751562 ; 29224898 ; 46505916 ; 46517467 ; 47213246 ; 47275539 ; 47424227 ; 47646545 ; 47646546 ; 47646547 ; 47720600 ; 47943749 ; 48094530 ; 48243347 ; 48318399 ; 48421873 ; 49684201 ; 49699003 ; 49965933 ; 50104169 ; 50104170 ; 50124146 ; 50124147 ; 50124148 ; 50967133 ; 53777619 ; 53787846
ChEBI ID
ChEBI:17263
CAS Number
53-16-7
TTD Drug ID
D00ZFP
Formula
C18H22O2
Canonical SMILES
CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)O
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
InChIKey
DNXHEGUUPJUMQT-CBZIJGRNSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
15alpha-OH-estrone DM000902
154699586
Unclear 1 [14]
16alpha-OH-estrone DM000903
154700061
Oxidation - Hydroxylation 1 [14]
16beta-OH-estrone DM000904
154700060
Oxidation - Hydroxylation 1 [14]
2-hydroxyestrone DM000871
440623
Oxidation - Hydroxylation 1 [5]
2-hydroxyestrone DM000871
440623
Oxidation - 2-Hydroxylation 1 [5]
2-hydroxyestrone sulfate DM000895
53481500
Unclear 1 [6]
4-hydroxyestrone DM000876
53477797
Oxidation - 4-Hydroxylation 1 [5]
4-hydroxyestrone sulfate DM000896
53481520
Unclear 1 [6]
4-OH-estrone DM000898
9971251
Oxidation - Hydroxylation 1 [14]
6alpha-OH-estrone DM000899
21122975
Oxidation - Hydroxylation 1 [14]
6beta-estrone DM000900
22295472
Unclear 1 [14]
7alpha-OH-estrone DM000901
154699807
Unclear 1 [14]
Estrone glucuronide DM000894
115255
Conjugation - Glucuronidation 1 [6]
Estrone sulfate DM003063
3001028
Unclear 1 [6]
2-hydroxyestrone-3-methyl DM000892
163196404
Unclear 2 [2]
2-methoxyestrone DM000872
440624
Unclear 2 [2]
4-methoxyestrone DM000893
194066
Unclear 2 [2]
⏷ Show the Full List of 17  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002696 Estrone 2-hydroxyestrone Oxidation - 2-Hydroxylation CYP1A2 ... [5]
MR002697 Estrone 4-hydroxyestrone Oxidation - 4-Hydroxylation CYP3A4 [5]
MR002698 Estrone Estrone glucuronide Conjugation - Glucuronidation Unclear [6]
MR002699 Estrone 2-hydroxyestrone sulfate Unclear Unclear [6]
MR002700 Estrone 4-hydroxyestrone sulfate Unclear Unclear [6]
MR002701 Estrone 4-OH-estrone Oxidation - Hydroxylation CYP1A1 ... [14]
MR002702 Estrone 6alpha-OH-estrone Oxidation - Hydroxylation CYP1A1 ... [14]
MR002703 Estrone 6beta-estrone Unclear CYP3A4 ... [14]
MR002704 Estrone 7alpha-OH-estrone Unclear CYP1A1 [14]
MR002705 Estrone 15alpha-OH-estrone Unclear CYP1A1 ... [14]
MR002706 Estrone 16alpha-OH-estrone Oxidation - Hydroxylation CYP1A1 ... [14]
MR002707 Estrone 16beta-OH-estrone Oxidation - Hydroxylation CYP2C8 ... [14]
MR002708 Estrone Estrone sulfate Unclear Unclear [6]
MR002693 2-hydroxyestrone 2-methoxyestrone Unclear COMT [2]
MR002694 2-hydroxyestrone 2-hydroxyestrone-3-methyl Unclear COMT [2]
MR002695 4-hydroxyestrone 4-methoxyestrone Unclear COMT [2]
⏷ Show the Full List of 16 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Catechol O-methyltransferase (COMT) DME0043 Homo sapiens
COMT_HUMAN
2.1.1.6
[2]
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[4]
Cytochrome P450 1B1 (CYP1B1) DME0023 Homo sapiens
CP1B1_HUMAN
1.14.14.1
[3]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[6]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[7]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[6]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[8]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[9]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[10]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[6]
Estradiol 17-beta-dehydrogenase 1 (HSD17B1) DME0420 Homo sapiens
DHB1_HUMAN
1.1.1.62
[11]
Estradiol 17-beta-dehydrogenase 2 (HSD17B2) DME0422 Homo sapiens
DHB2_HUMAN
1.1.1.62
[11]
Farnesol dehydrogenase (AKR1B15) DME0399 Homo sapiens
AK1BF_HUMAN
1.1.1.54
[12]
Keto-steroid reductase (HSD17B7) DME0424 Homo sapiens
DHB7_HUMAN
1.1.1.270
[11]
Ketoacyl-CoA reductase (HSD17B12) DME0421 Homo sapiens
DHB12_HUMAN
1.1.1.330
[13]
Lauric acid omega-hydroxylase (CYP4A11) DME0029 Homo sapiens
CP4AB_HUMAN
1.14.15.3
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[6]
Peroxisomal multifunctional enzyme 2 (HSD17B4) DME0263 Homo sapiens
DHB4_HUMAN
4.2.1.119
[11]
⏷ Show the Full List of 20  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Farnesol dehydrogenase (AKR1B15) DME0399 Km = 0.0035 microM
AK1BF_HUMAN
[12]
Ketoacyl-CoA reductase (HSD17B12) DME0421 Km = 0.0025 microM
DHB12_HUMAN
[13]
References
1 Estrone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Evaluation of electrospray ionization and atmospheric pressure chemical ionization for simultaneous detection of estrone and its metabolites using high-performance liquid chromatography/tandem mass spectrometry J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Dec 1;860(1):49-56. doi: 10.1016/j.jchromb.2007.10.014.
3 A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio. Clin Chem Lab Med. 2005;43(7):702-6.
4 A transgenic mouse expressing human CYP1A2 in the pancreas. Biochem Pharmacol. 2000 Sep 15;60(6):857-63.
5 Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98.
6 DrugBank(Pharmacology-Metabolism)Estrone
7 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
8 Novel metabolic pathway of estrone and 17beta-estradiol catalyzed by cytochrome P-450. Drug Metab Dispos. 2000 Feb;28(2):110-2.
9 Regioselective hydroxylation of steroid hormones by human cytochromes P450. Drug Metab Rev. 2015 May;47(2):89-110.
10 16Alpha-hydroxylation of estrone by human cytochrome P4503A4/5. Carcinogenesis. 1998 May;19(5):867-72.
11 Steroid signalling in the ovarian surface epithelium. Trends Endocrinol Metab. 2005 Sep;16(7):327-33.
12 Aldo-keto Reductase 1B15 (AKR1B15): a mitochondrial human aldo-keto reductase with activity toward steroids and 3-keto-acyl-CoA conjugates. J Biol Chem. 2015 Mar 6;290(10):6531-45.
13 Characterization of type 12 17beta-hydroxysteroid dehydrogenase, an isoform of type 3 17beta-hydroxysteroid dehydrogenase responsible for estradiol formation in women. Mol Endocrinol. 2006 Feb;20(2):437-43.
14 Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.