Guggulsterone

Details

• Internal ID: 181873ad-4dff-4e41-956e-6208e8e29ceb
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Androstane steroids > Androgens and derivatives
• IUPAC Name: (8R,9S,10R,13S,14S,17Z)-17-ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione
• SMILES (Canonical): CC=C1C(=O)CC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
• SMILES (Isomeric): C/C=C/1\C(=O)C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
• InChI: InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4+/t15-,17+,18+,20+,21-/m1/s1
• InChI Key: WDXRGPWQVHZTQJ-OSJVMJFVSA-N
• Popularity: 438 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.40 g/mol
• Exact Mass: 312.208930132 g/mol
• Topological Polar Surface Area (TPSA): 34.10 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.64
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Z-Guggulsterone
• Guggulsterone
• 39025-23-5
• 95975-55-6
• Guggulsterones Z
• GUGGULSTERONE Z
• Guggulsterone, (Z)-
• Guggulsterone E&Z
• Cis-Guggulsterone
• UNII-6CST3U34GN
• 6CST3U34GN
• DTXSID1033539
• (Z)-Pregna-4,17(20)-diene-3,16-dione
• Z/E-Guggulsterone
• Pregna-4,17(20)-diene-3,16-dione, (17Z)-
• Pregna-4,17(20)-diene-3,16-dione
• (8R,9S,10R,13S,14S,17Z)-17-ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione
• Gugulsterone
• (17Z)-Guggulsterone
• (17Z)-Pregna-4,17(20)-diene-3,16-dione
• 4,17(20)-cis-Pregnadiene-3,6-dione
• Guggulsterones E&Z
• GS
• (17Z)-pregna-4,17-diene-3,16-dione
• (E&Z)-Guggulsterone
• GUGGULSTERONE Z-FORM
• SCHEMBL141657
• CHEMBL410683
• DTXCID9013539
• BDBM21725
• GUGGULSTERONE Z [USP-RS]
• CHEBI:135338
• GUGGULSTERONE Z-FORM [MI]
• WDXRGPWQVHZTQJ-OSJVMJFVSA-N
• BCP18087
• Tox21_202518
• AKOS015963432
• (Z)-Guggulsterone, analytical standard
• AC-6215
• CCG-267610
• NCGC00091910-01
• NCGC00260067-01
• AC-28813
• AS-79083
• pregna-4,17Z(20)-diene-3,16-dione
• CAS-39025-23-5
• HY-107738
• CS-0029421
• S3792
• (Z)-Guggulsterone, >=89% (HPLC), powder
• 2-(2-Aminothiazol-3(2H)-yl)-1-phenylethanone
• BRD-K26674531-001-01-3
• GUGGULSTERONE Z (CONSTITUENT OF GUGGUL) [DSC]
• Q27264514
• Guggulsterone Z, United States Pharmacopeia (USP) Reference Standard
• (1S,2R,10R,11S,14Z,15S)-14-ethylidene-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,13-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8896	88.96%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6698	66.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8600	86.00%
OATP1B3 inhibitior	+	0.9819	98.19%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.8000	80.00%
BSEP inhibitior	+	0.7908	79.08%
P-glycoprotein inhibitior	+	0.9250	92.50%
P-glycoprotein substrate	-	0.8749	87.49%
CYP3A4 substrate	+	0.6680	66.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8716	87.16%
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	-	0.8277	82.77%
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	-	0.9716	97.16%
Skin irritation	+	0.6173	61.73%
Skin corrosion	-	0.9668	96.68%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6932	69.32%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.7805	78.05%
skin sensitisation	+	0.6755	67.55%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7152	71.52%
Acute Oral Toxicity (c)	III	0.8127	81.27%
Estrogen receptor binding	+	0.8426	84.26%
Androgen receptor binding	+	0.8504	85.04%
Thyroid receptor binding	+	0.8461	84.61%
Glucocorticoid receptor binding	+	0.8229	82.29%
Aromatase binding	+	0.6028	60.28%
PPAR gamma	-	0.5859	58.59%
Honey bee toxicity	-	0.7000	70.00%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.9910	99.10%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	28183.8 nM	Potency	via CMAUP
CHEMBL1871	P10275	Androgen Receptor	660 nM	IC50	PMID: 16250653
CHEMBL2047	Q96RI1	Bile acid receptor FXR	89360 nM; 100000 nM; 89400 nM; 12000 nM; 12000 nM; 10000 nM	IC50; IC50; IC50; IC50; IC50; IC50	PMID: 24513188; PMID: 16250653; PMID: 26337021; PMID: 23688559; PMID: 17292610; PMID: 16905319
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	316.2 nM	Potency	via Super-PRED
CHEMBL2034	P04150	Glucocorticoid receptor	6060 nM	IC50	PMID: 16250653
CHEMBL1293224	P10636	Microtubule-associated protein tau	100 nM	Potency	via Super-PRED
CHEMBL1994	P08235	Mineralocorticoid receptor	1880 nM	IC50	PMID: 16250653
CHEMBL3401	O75469	Pregnane X receptor	2.4 nM	IC50	PMID: 16250653
CHEMBL208	P06401	Progesterone receptor	740 nM	IC50	PMID: 16250653
CHEMBL1293232	Q16637	Survival motor neuron protein	15848.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1994	P08235	Mineralocorticoid receptor	96.28%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.94%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.85%	96.09%
CHEMBL1871	P10275	Androgen Receptor	92.50%	96.43%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.02%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.46%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.51%	93.40%
CHEMBL1902	P62942	FK506-binding protein 1A	89.27%	97.05%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	88.40%	94.78%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	84.81%	85.30%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.14%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.95%	82.69%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.96%	97.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.89%	86.33%
CHEMBL2581	P07339	Cathepsin D	80.41%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	80.35%	94.75%

Plants that contains it

• Abutilon indicum
• Angylocalyx oligophyllus
• Commiphora wightii
• Hedera rhombea
• Tricalysia okelensis

Cross-Links

• PubChem: 6450278
• NPASS: NPC2634
• ChEMBL: CHEMBL410683
• LOTUS: LTS0054235
• wikiData: Q27264514