14-Hydro-15-hydroxyajugapitin

Details

• Internal ID: 57907b11-613a-49b4-ae4d-a8155188c532
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(1R,2S,3R,4aR,5S,6R,8S,8aR)-5-[(2S,3aS,6aR)-5-hydroxy-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-2-yl]-8-acetyloxy-8a-(acetyloxymethyl)-3-hydroxy-5,6-dimethylspiro[3,4,4a,6,7,8-hexahydro-2H-naphthalene-1,2'-oxirane]-2-yl] 2-methylbutanoate
• InChI: InChI=1S/C29H44O11/c1-7-14(2)25(34)40-24-19(32)11-20-27(6,21-9-18-10-23(33)39-26(18)38-21)15(3)8-22(37-17(5)31)28(20,12-35-16(4)30)29(24)13-36-29/h14-15,18-24,26,32-33H,7-13H2,1-6H3/t14?,15-,18+,19-,20-,21+,22+,23?,24+,26-,27+,28+,29-/m1/s1
• InChI Key: SAENNVULKVVZSO-ZDEAQARGSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₄O₁₁
• Molecular Weight: 568.70 g/mol
• Exact Mass: 568.28836222 g/mol
• Topological Polar Surface Area (TPSA): 150.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.09
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• CHEBI:67471
• 14-hydro-2,15-dihydroxy-3beta-isobutyryloxyclerodin
• Q27135939
• (1R,2S,3R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5-[(2S,3aS,6aR)-5-hydroxyhexahydrofuro[2,3-b]furan-2-yl]-5,6-dimethyloctahydro-2H-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylbutanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9630	96.30%
Caco-2	-	0.7725	77.25%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7101	71.01%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8682	86.82%
OATP1B3 inhibitior	+	0.9110	91.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7732	77.32%
P-glycoprotein inhibitior	+	0.6746	67.46%
P-glycoprotein substrate	+	0.6066	60.66%
CYP3A4 substrate	+	0.6740	67.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8620	86.20%
CYP3A4 inhibition	+	0.5261	52.61%
CYP2C9 inhibition	-	0.7944	79.44%
CYP2C19 inhibition	-	0.8073	80.73%
CYP2D6 inhibition	-	0.9484	94.84%
CYP1A2 inhibition	-	0.9166	91.66%
CYP2C8 inhibition	+	0.4846	48.46%
CYP inhibitory promiscuity	-	0.8561	85.61%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5108	51.08%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9139	91.39%
Skin irritation	-	0.6558	65.58%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	-	0.5937	59.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5859	58.59%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.5983	59.83%
skin sensitisation	-	0.8937	89.37%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5401	54.01%
Acute Oral Toxicity (c)	I	0.5502	55.02%
Estrogen receptor binding	+	0.7848	78.48%
Androgen receptor binding	+	0.7056	70.56%
Thyroid receptor binding	-	0.5865	58.65%
Glucocorticoid receptor binding	+	0.6656	66.56%
Aromatase binding	+	0.7040	70.40%
PPAR gamma	+	0.6567	65.67%
Honey bee toxicity	-	0.7306	73.06%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6855	68.55%
Fish aquatic toxicity	+	0.9813	98.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.99%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.94%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.92%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.37%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.24%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	94.27%	97.79%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	93.98%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	92.51%	91.19%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	90.66%	95.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.48%	96.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.45%	96.47%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.31%	97.21%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	89.31%	82.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	89.29%	89.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.22%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.95%	82.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.43%	85.14%
CHEMBL299	P17252	Protein kinase C alpha	88.32%	98.03%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	87.87%	89.05%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.43%	96.61%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.36%	91.24%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.98%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.98%	96.77%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	83.12%	92.86%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.61%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	82.42%	92.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.13%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.08%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.14%	92.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.98%	91.07%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.42%	97.28%

Plants that contains it

• Ajuga chamaepitys

Cross-Links

• PubChem: 70697927
• LOTUS: LTS0270601
• wikiData: Q27135939