Ajugasterone C

Details

• Internal ID: 088f94f5-f1f4-4727-8f69-d58decac3ccd
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives
• IUPAC Name: (2S,3R,5R,9R,10R,11R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,3,11,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• SMILES (Canonical): CC(C)CCC(C(C)(C1CCC2(C1(CC(C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)O)C)O)O)O
• SMILES (Isomeric): CC(C)CC[C@H]([C@@](C)([C@H]1CC[C@@]2([C@@]1(C[C@H]([C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)O)C)O)O)O
• InChI: InChI=1S/C27H44O7/c1-14(2)6-7-22(32)26(5,33)21-8-9-27(34)16-11-17(28)15-10-18(29)19(30)12-24(15,3)23(16)20(31)13-25(21,27)4/h11,14-15,18-23,29-34H,6-10,12-13H2,1-5H3/t15-,18+,19-,20+,21-,22+,23+,24-,25+,26+,27+/m0/s1
• InChI Key: LQGNCUXDDPRDJH-UKTRSHMFSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₇
• Molecular Weight: 480.60 g/mol
• Exact Mass: 480.30870374 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.71
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• 23044-80-6
• (+)-Ajugasterone C
• Cholest-7-en-6-one, 2,3,11,14,20,22-hexahydroxy-, (2beta,3beta,5beta,11alpha,22R)-
• C08811
• CHEBI:2528
• CHEMBL3793486
• DTXSID80945728
• HY-N2196
• AKOS032946017
• CS-0019504
• 2,3,11,14,20,22-Hexahydroxycholest-7-en-6-one
• Q27105705

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.5232	52.32%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8310	83.10%
OATP2B1 inhibitior	-	0.7187	71.87%
OATP1B1 inhibitior	+	0.9164	91.64%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.5551	55.51%
P-glycoprotein inhibitior	-	0.6685	66.85%
P-glycoprotein substrate	+	0.5941	59.41%
CYP3A4 substrate	+	0.7074	70.74%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8690	86.90%
CYP2C19 inhibition	-	0.8364	83.64%
CYP2D6 inhibition	-	0.9516	95.16%
CYP1A2 inhibition	-	0.9278	92.78%
CYP2C8 inhibition	-	0.6902	69.02%
CYP inhibitory promiscuity	-	0.8761	87.61%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6900	69.00%
Eye corrosion	-	0.9944	99.44%
Eye irritation	-	0.9420	94.20%
Skin irritation	+	0.6543	65.43%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3941	39.41%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.5143	51.43%
skin sensitisation	-	0.7034	70.34%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.9050	90.50%
Acute Oral Toxicity (c)	III	0.5365	53.65%
Estrogen receptor binding	+	0.7560	75.60%
Androgen receptor binding	+	0.7290	72.90%
Thyroid receptor binding	+	0.5783	57.83%
Glucocorticoid receptor binding	+	0.7361	73.61%
Aromatase binding	+	0.6186	61.86%
PPAR gamma	-	0.5452	54.52%
Honey bee toxicity	-	0.8318	83.18%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9934	99.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.54%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.49%	97.25%
CHEMBL2581	P07339	Cathepsin D	98.19%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.30%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.37%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.71%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.57%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.93%	94.45%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	92.49%	94.78%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.34%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.85%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.51%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.49%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.10%	96.61%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.87%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.82%	93.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.24%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.04%	91.07%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.64%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.54%	89.34%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.32%	96.90%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.91%	90.24%

Plants that contains it

• Ajuga integrifolia
• Ajuga nipponensis
• Bellis perennis
• Cyanotis arachnoidea
• Euphorbia hirta
• Gentiana crassicaulis
• Gentiana dahurica
• Gentiana macrophylla
• Gentiana straminea
• Gomphrena haageana
• Klasea centauroides subsp. strangulata
• Rhaponticum carthamoides subsp. carthamoides
• Serratula coronata
• Vitex madiensis
• Vitex polygama
• Vitex scabra
• Vitex strickeri
• Vitex tripinnata

Cross-Links

• PubChem: 441826
• NPASS: NPC217201
• ChEMBL: CHEMBL3793486
• LOTUS: LTS0011944
• wikiData: Q105255990