Ajugaciliatin B

Details

• Internal ID: a744858c-6ae1-4604-b661-124d1bdf960b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1S)-2-[(1S,2R,4S,4aR,5R,8R,8aR)-4,8-diacetyloxy-4a-(acetyloxymethyl)-5-(chloromethyl)-5-hydroxy-1,2-dimethyl-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-1-(5-oxo-2H-furan-3-yl)ethyl] (2S)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC(CC1(C(CC(C2(C1C(CCC2(CCl)O)OC(=O)C)COC(=O)C)OC(=O)C)C)C)C3=CC(=O)OC3
• SMILES (Isomeric): CC[C@H](C)C(=O)O[C@@H](C[C@]1([C@@H](C[C@@H]([C@@]2([C@@H]1[C@@H](CC[C@@]2(CCl)O)OC(=O)C)COC(=O)C)OC(=O)C)C)C)C3=CC(=O)OC3
• InChI: InChI=1S/C31H45ClO11/c1-8-17(2)28(37)43-24(22-12-26(36)39-14-22)13-29(7)18(3)11-25(42-21(6)35)31(16-40-19(4)33)27(29)23(41-20(5)34)9-10-30(31,38)15-32/h12,17-18,23-25,27,38H,8-11,13-16H2,1-7H3/t17-,18+,23+,24-,25-,27+,29-,30-,31+/m0/s1
• InChI Key: LMCZPZLFURXAIA-JKZOSZDYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₅ClO₁₁
• Molecular Weight: 629.10 g/mol
• Exact Mass: 628.2650399 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.66
• H-Bond Acceptor: 11
• H-Bond Donor: 1
• Rotatable Bonds: 11

Synonyms

• CHEBI:69861
• CHEMBL1813850
• Q27138201
• (12S,2'''S)-1beta,6alpha,19-triacetoxy-18-chloro-4alpha-hydroxy-12-(2-methylbutanoyloxy)-neo-clerod-13-en-15,16-olide
• (1S)-2-[(1S,2R,4S,4aR,5R,8R,8aR)-4,8-bis(acetyloxy)-4a-[(acetyloxy)methyl]-5-(chloromethyl)-5-hydroxy-1,2-dimethyldecahydronaphthalen-1-yl]-1-(5-oxo-2,5-dihydrofuran-3-yl)ethyl (2S)-2-methylbutanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	-	0.7720	77.20%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7631	76.31%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.8591	85.91%
OATP1B3 inhibitior	+	0.9139	91.39%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9909	99.09%
P-glycoprotein inhibitior	+	0.8396	83.96%
P-glycoprotein substrate	+	0.6629	66.29%
CYP3A4 substrate	+	0.7055	70.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9120	91.20%
CYP3A4 inhibition	-	0.5201	52.01%
CYP2C9 inhibition	-	0.7419	74.19%
CYP2C19 inhibition	-	0.7510	75.10%
CYP2D6 inhibition	-	0.8921	89.21%
CYP1A2 inhibition	-	0.8146	81.46%
CYP2C8 inhibition	+	0.5758	57.58%
CYP inhibitory promiscuity	-	0.7972	79.72%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5343	53.43%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9159	91.59%
Skin irritation	+	0.5505	55.05%
Skin corrosion	-	0.9272	92.72%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7435	74.35%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5274	52.74%
skin sensitisation	-	0.9028	90.28%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.5758	57.58%
Acute Oral Toxicity (c)	III	0.5111	51.11%
Estrogen receptor binding	+	0.8269	82.69%
Androgen receptor binding	+	0.7295	72.95%
Thyroid receptor binding	+	0.5571	55.71%
Glucocorticoid receptor binding	+	0.8123	81.23%
Aromatase binding	+	0.7535	75.35%
PPAR gamma	+	0.6994	69.94%
Honey bee toxicity	-	0.6881	68.81%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9961	99.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.61%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.54%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.76%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.01%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.51%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.54%	82.69%
CHEMBL221	P23219	Cyclooxygenase-1	90.62%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.18%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.60%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.77%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.60%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.10%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.99%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.89%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.54%	96.77%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.96%	97.28%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.89%	97.14%
CHEMBL5255	O00206	Toll-like receptor 4	83.20%	92.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.97%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.85%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.69%	93.56%
CHEMBL4040	P28482	MAP kinase ERK2	82.62%	83.82%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.35%	89.50%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.90%	89.05%

Plants that contains it

• Ajuga ciliata

Cross-Links

• PubChem: 53465564
• LOTUS: LTS0247948
• wikiData: Q27138201