Progesterone

Details

• Internal ID: ce160985-4f69-4c40-b05e-df0c91636007
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Pregnane steroids > Gluco/mineralocorticoids, progestogins and derivatives
• IUPAC Name: (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• SMILES (Canonical): CC(=O)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
• SMILES (Isomeric): CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
• InChI: InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1
• InChI Key: RJKFOVLPORLFTN-LEKSSAKUSA-N
• Popularity: 120,599 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.50 g/mol
• Exact Mass: 314.224580195 g/mol
• Topological Polar Surface Area (TPSA): 34.10 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.72
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 57-83-0
• Pregn-4-ene-3,20-dione
• Agolutin
• Crinone
• 4-Pregnene-3,20-dione
• Utrogestan
• Prometrium
• Syngesterone
• Luteol
• Cyclogest
• Gestormone
• Glanducorpin
• Pregnenedione
• Progestasert
• Progesterol
• Progesteronum
• Progestin
• Progestone
• Progestron
• Corlutin
• Gestone
• Hormoflaveine
• Lutociclina
• Methylpregnone
• Progestosol
• Progestronol
• Syngestrets
• Corlutina
• Corluvite
• Corporin
• Flavolutan
• Fologenon
• Gesterol
• Gestron
• Gynlutin
• Gynolutone
• Hormoluton
• Lingusorbs
• Lucorteum
• Luteodyn
• Luteogan
• Luteopur
• Luteosan
• Luteostab
• Luteovis
• Lutidon
• Lutocyclin
• Lutocylin
• Lutoform
• Lutogyl
• Lutromone
• Membrettes
• Nalutron
• Piaponon
• Primolut
• Progekan
• Prolets
• Prolidon
• Proluton
• Protormone
• Syntolutan
• Lutren
• Lucorteum Sol
• Bio-luton
• Lutocyclin M
• Lipo-Lutin
• Luteocrin normale
• Luteinique
• Prochieve
• Prolutone
• Lutex
• Lutin
• 17alpha-Progesterone
• Synovex S
• Gynoluton
• Projestaject
• Percutacrine Luteinique
• Gesterol 100
• Akrolutin
• Gesterol 50
• Pregnene-3,20-dione
• Cyclogesterin
• Endometrin
• Progesteron
• Progestogel
• Progeston
• Prolutin
• (S)-Progesterone
• 3,20-Pregnene-4
• Gelbkoerperhormon
• Colprosterone
• Gestiron
• Progestol
• Crinone progesterone gel
• Lugesteron
• Vitarrine
• Luteum
• Luteol (VAN)
• NSC-9704
• Lutocuclin M
• (S)-4-Pregnene-3,20-dione
• Delta(4)-pregnene-3,20-dione
• (S)-Pregn-4-en-3,20-dione
• .beta.-Progesterone
• delta(sup 4)-Pregnene-3,20-dione
• Percutacrine
• Progesterona
• Progeffik
• Utrogest
• Progesteronum [INN-Latin]
• Progesterona [INN-Spanish]
• CCRIS 533
• HSDB 3389
• AI3-51682
• Prontogest
• Lipolutin
• Lutogynon
• Progestan
• Estima
• Progesterone, micronized
• 17.alpha.-Progesterone
• CHEBI:17026
• 6alpha-Methylpregn-4-en-17alpha-ol-3,20-dione
• Progesterone [Progestins]
• beta-Progesterone
• NSC 9704
• 17alpha-Hydroxy-6alpha-methylpregn-4-ene-3,20-dione
• Prometrium (TN)
• EINECS 200-350-6
• Pregn-4-en-3,20-dione
• UNII-4G7DS2Q64Y
• NSC 64377
• NSC-64377
• Crinone (TN)
• Pregn-4-ene-3,20-dione, 17alpha-hydroxy-6alpha-methyl-
• MILPROSA
• 4G7DS2Q64Y
• DTXSID3022370
• .delta.4-Pregnene-3,20-dione
• NSC9704
• delta(Sup4)-pregnene-3,20-dione
• NSC64377
• component of Cyclogesterin
• U 3672
• 4-Pregnen-3,20-dione
• .delta.(sup4)-Pregnene-3,20-dione
• CHEMBL103
• D4-Pregnene-3,20-dione
• lugesterone
• Progesterone [INN:BAN:JAN]
• MLS000028517
• DTXCID902370
• EC 200-350-6
• Progesterone [USP:INN:BAN:JAN]
• BIJUVA COMPONENT PROGESTERONE
• PROGESTERONE COMPONENT OF BIJUVA
• NCGC00015785-04
• SMR000058345
• PROGESTERONE (MART.)
• PROGESTERONE [MART.]
• (8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one
• PROGESTERONE (USP-RS)
• PROGESTERONE [USP-RS]
• 6.alpha.-Methylpregn-4-en-17.alpha.-ol-3,20-dione
• (8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• 17.alpha.-Hydroxy-6.alpha.-methylpregn-4-ene-3,20-dione
• PROGESTERONE (EP MONOGRAPH)
• PROGESTERONE [EP MONOGRAPH]
• Pregn-4-ene-3,20-dione, 17.alpha.-hydroxy-6.alpha.-methyl-
• PROGESTERONE (USP MONOGRAPH)
• PROGESTERONE [USP MONOGRAPH]
• SMR000653542
• delta4-Pregnene-3,20-dione
• Progesterone (Prometrium)
• WLN: L E5 B666 OV MUTJ A1 E1 FV1
• SR-01000000088
• SR-01000076054
• Pregn-4-ene-3, 17.alpha.-hydroxy-6.alpha.-methyl-
• BHR-100
• Duraprogen
• Progestrel
• Lutinus
• Gelbkorperhormon
• progesteron-
• Lutocylin M
• Progesterone??
• 1dbb
• 17a-Progesterone
• CAS-57-83-0
• racemic progesterone
• Crinone 8%
• Prestwick_411
• Natural Progesterone
• MFCD00003658
• CIDR
• mpp22
• Micronized Progesterone
• Therapeutic Progesterone
• 2aa6
• 4bb2
• Opera_ID_292
• Progesterone, >=99%
• Prestwick0_000477
• Prestwick1_000477
• Prestwick2_000477
• Prestwick3_000477
• Spectrum5_002053
• PROGESTERONE [MI]
• Cyclogesterin (Salt/Mix)
• PROGESTERONE [INN]
• PROGESTERONE [JAN]
• bmse000482
• D07BSQ
• Epitope ID:116051
• PROGESTERONE [HSDB]
• PROGESTERONE [INCI]
• Pregn-4-ne-3,20-ione
• SCHEMBL7671
• PROGESTERONE [VANDF]
• BIDD:PXR0094
• Lopac0_000895
• BSPBio_000614
• MLS000758277
• MLS001074187
• MLS001423982
• MLS002222367
• BIDD:ER0547
• P0130_SIGMA
• PROGESTERONE [WHO-DD]
• PROGESTERONE [WHO-IP]
• Progesterone [BAN:INN:JAN]
• SPBio_002553
• .delta.-Pregnene-3,20-dione
• BDBM8903
• BPBio1_000676
• delta-4-pregnene-3,20-dione
• GTPL2377
• Hydroxyprogesterone Caproic acid
• LPCN-1107
• Progesterone (JP17/USP/INN)
• BHR-310
• ETI-411
• G03DA04
• PROGESTERONE [GREEN BOOK]
• 1a28
• 1h60
• HMS1569O16
• HMS2051O05
• HMS2090J07
• HMS2096O16
• HMS2230F23
• HMS2233P11
• HMS3262D12
• HMS3713O16
• Pregnene, 3,20-dione-delta^4-
• PROGESTERONE [ORANGE BOOK]
• Progesterone (oral, preterm labor)
• BCP22000
• HY-N0437
• Tox21_113157
• Tox21_201792
• Tox21_300307
• Tox21_500895
• AC-700
• CMC_13406
• LMST02030159
• LS-234
• PROGESTERONUM [WHO-IP LATIN]
• s1705
• AKOS015894908
• Progesterone; 4-Pregnene-3,20-dione
• CCG-100766
• CS-1937
• DB00396
• DR-2011
• FD12045
• LP00895
• NC00016
• SDCCGSBI-0050870.P002
• Progesterone 1.0 mg/ml in Acetonitrile
• NCGC00022185-03
• NCGC00022185-04
• NCGC00022185-05
• NCGC00022185-06
• NCGC00022185-07
• NCGC00022185-08
• NCGC00022185-09
• NCGC00022185-10
• NCGC00022185-11
• NCGC00022185-12
• NCGC00022185-14
• NCGC00022185-21
• NCGC00090798-01
• NCGC00090798-02
• NCGC00254120-01
• NCGC00259341-01
• NCGC00261580-01
• (1S,10S,11S,14S,15S,2R)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0<2,7>.0 <11,15>]heptadec-6-ene
• (8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
• AS-12660
• CPD000058345
• NCI60_042166
• FE-999913
• EU-0100895
• P0478
• Progesterone (oral, preterm labor), Lipocine
• Progesterone, meets USP testing specifications
• Progesterone, Vetec(TM) reagent grade, 98%
• C00410
• D00066
• P 0130
• Q26963
• S00293
• Progesterone, VETRANAL(TM), analytical standard
• Q-201624
• SR-01000000088-5
• SR-01000000088-6
• SR-01000076054-1
• SR-01000076054-4
• BRD-K64994968-001-03-6
• 32104FB6-BF81-4F6E-83C2-024DEEAEB272
• Z1501485353
• Progesterone, British Pharmacopoeia (BP) Reference Standard
• Progesterone, powder, BioReagent, suitable for cell culture
• Progesterone, European Pharmacopoeia (EP) Reference Standard
• Progesterone, gamma-irradiated, BioXtra, suitable for cell culture
• Progesterone, United States Pharmacopeia (USP) Reference Standard
• Progesterone-Water Soluble, powder, BioReagent, suitable for cell culture
• Progesterone for peak identification, European Pharmacopoeia (EP) Reference Standard
• Progesterone for system suitability, European Pharmacopoeia (EP) Reference Standard
• Progesterone, Pharmaceutical Secondary Standard; Certified Reference Material
• (1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadec-6-en-5-one
• 137940-28-4
• 753497-20-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8534	85.34%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6698	66.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7650	76.50%
OATP1B3 inhibitior	+	0.9819	98.19%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	+	0.8000	80.00%
BSEP inhibitior	+	0.9001	90.01%
P-glycoprotein inhibitior	+	0.9518	95.18%
P-glycoprotein substrate	-	0.9309	93.09%
CYP3A4 substrate	+	0.7980	79.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8713	87.13%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.6514	65.14%
CYP2D6 inhibition	-	0.9533	95.33%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9229	92.29%
CYP inhibitory promiscuity	-	0.8203	82.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Warning	0.4528	45.28%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9704	97.04%
Skin irritation	+	0.6173	61.73%
Skin corrosion	-	0.9668	96.68%
Ames mutagenesis	-	0.9574	95.74%
Human Ether-a-go-go-Related Gene inhibition	-	0.4103	41.03%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.9500	95.00%
skin sensitisation	+	0.6755	67.55%
Respiratory toxicity	+	0.9667	96.67%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8418	84.18%
Acute Oral Toxicity (c)	III	0.8127	81.27%
Estrogen receptor binding	+	0.9117	91.17%
Androgen receptor binding	+	0.8747	87.47%
Thyroid receptor binding	+	0.8460	84.60%
Glucocorticoid receptor binding	+	0.9162	91.62%
Aromatase binding	+	0.7294	72.94%
PPAR gamma	-	0.6860	68.60%
Honey bee toxicity	-	0.8469	84.69%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9910	99.10%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	17000 nM	IC50	PMID: 3100794
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1871	P10275	Androgen Receptor	37 nM; 8.5 nM; 37 nM; 37 nM; 37 nM; 37 nM	IC50; Ki; IC50; IC50; IC50; IC50	PMID: 9784110; via Super-PRED; PMID: 9464360; PMID: 8627601; PMID: 12781197; PMID: 12954062
CHEMBL2421	P08185	Corticosteroid binding globulin	41.69 nM	Ki	PMID: 15139751
CHEMBL3397	P11712	Cytochrome P450 2C9	5500 nM	Ki	PMID: 14761192
CHEMBL340	P08684	Cytochrome P450 3A4	3981.1 nM; 3981.1 nM; 3981.1 nM; 3981.1 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL4879	P12104	Fatty acid binding protein intestinal	20000 nM	Ki	PMID: 18533710
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	2770 nM	EC50	PMID: 18307294
CHEMBL2034	P04150	Glucocorticoid receptor	330 nM; 30.5 nM	IC50; Ki	via CMAUP; via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM; 14125.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	39810.7 nM	Potency	via CMAUP
CHEMBL1994	P08235	Mineralocorticoid receptor	0.39 nM; 14 nM; 14 nM; 14 nM; 14 nM	Kd; IC50; IC50; IC50; IC50	via Super-PRED; PMID: 9784110; PMID: 12781197; PMID: 9464360; PMID: 12954062
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	10000 nM	Potency	via CMAUP
CHEMBL4302	P08183	P-glycoprotein 1	48977.88 nM; 192200 nM; 88100 nM; 96200 nM; 47863.01 nM; 47863.01 nM	IC50; IC50; IC50; IC50; IC50; IC50	PMID: 17890094; PMID: 11716514; PMID: 11716514; PMID: 11716514; PMID: 18678495; PMID: 17890094
CHEMBL1293235	P02545	Prelamin-A/C	35481.3 nM; 35481.3 nM; 10000 nM; 6309.6 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL208	P06401	Progesterone receptor	0.1 nM; 5 nM; 17 nM; 3.5 nM; 0.2 nM	EC50; IC50; IC50; IC50; IC50	via Super-PRED; PMID: 8523399; PMID: 8523400; PMID: 11859003; PMID: 24900290
CHEMBL287	Q99720	Sigma opioid receptor	3055 nM	IC50	via CMAUP
CHEMBL5685	O15245	Solute carrier family 22 member 1	3050 nM	IC50	PMID: 12110607
CHEMBL1743122	O15244	Solute carrier family 22 member 2	26700 nM	IC50	PMID: 12110607
CHEMBL2073673	O75751	Solute carrier family 22 member 3	4280 nM	IC50	PMID: 12110607
CHEMBL1293232	Q16637	Survival motor neuron protein	15848.9 nM; 14125.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3305	P04278	Testis-specific androgen-binding protein	114.82 nM	Kd	via Super-PRED
CHEMBL1293256	P40225	Thrombopoietin	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	10000 nM; 25118.9 nM; 25118.9 nM; 10000 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.70%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.80%	91.11%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	92.38%	85.30%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	90.04%	94.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.45%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	86.92%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.63%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.48%	94.45%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.78%	93.04%
CHEMBL1940	Q13936	Voltage-gated L-type calcium channel alpha-1C subunit	82.75%	86.00%
CHEMBL2581	P07339	Cathepsin D	81.86%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.29%	89.00%

Plants that contains it

• Actinoscirpus grossus var. kysoor
• Alangium ridleyi
• Conioselinum anthriscoides
• Cota palaestina
• Hedysarum denticulatum
• Helichrysum nitens
• Jacobaea erucifolia subsp. argunensis
• Juglans regia
• Ligularia songarica
• Linum usitatissimum
• Lonicera japonica
• Mangifera indica
• Perilla frutescens
• Platypodium elegans
• Reseda luteola
• Senecio nemorensis
• Vitex agnus-castus

Cross-Links

• PubChem: 5994
• NPASS: NPC307176
• ChEMBL: CHEMBL103
• LOTUS: LTS0238391
• wikiData: Q26963