[(1S,4aR,6R,6aR,8R,10R,10aS,10bS)-6-acetyloxy-8-ethenyl-1,6a-dihydroxy-4,4,8,10b-tetramethyl-3,7-dioxo-4a,5,6,9,10,10a-hexahydro-1H-benzo[h]isochromen-10-yl] benzoate

Details

• Internal ID: 52f1d537-9b7c-4a30-ab7e-d9bebc018ec7
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: [(1S,4aR,6R,6aR,8R,10R,10aS,10bS)-6-acetyloxy-8-ethenyl-1,6a-dihydroxy-4,4,8,10b-tetramethyl-3,7-dioxo-4a,5,6,9,10,10a-hexahydro-1H-benzo[h]isochromen-10-yl] benzoate
• SMILES (Canonical): CC(=O)OC1CC2C(C(=O)OC(C2(C3C1(C(=O)C(CC3OC(=O)C4=CC=CC=C4)(C)C=C)O)C)O)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@@]([C@@H]3[C@@]1(C(=O)[C@@](C[C@H]3OC(=O)C4=CC=CC=C4)(C)C=C)O)([C@H](OC(=O)C2(C)C)O)C
• InChI: InChI=1S/C28H34O9/c1-7-26(5)14-17(36-21(30)16-11-9-8-10-12-16)20-27(6)18(25(3,4)23(32)37-24(27)33)13-19(35-15(2)29)28(20,34)22(26)31/h7-12,17-20,24,33-34H,1,13-14H2,2-6H3/t17-,18+,19-,20-,24+,26+,27+,28+/m1/s1
• InChI Key: YWQLMKNFNDFXOQ-QKHVDKSASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₉
• Molecular Weight: 514.60 g/mol
• Exact Mass: 514.22028266 g/mol
• Topological Polar Surface Area (TPSA): 136.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9484	94.84%
Caco-2	-	0.7411	74.11%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6188	61.88%
OATP2B1 inhibitior	-	0.8543	85.43%
OATP1B1 inhibitior	+	0.8673	86.73%
OATP1B3 inhibitior	+	0.8441	84.41%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8307	83.07%
P-glycoprotein inhibitior	+	0.7697	76.97%
P-glycoprotein substrate	-	0.6034	60.34%
CYP3A4 substrate	+	0.6824	68.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8772	87.72%
CYP3A4 inhibition	+	0.5818	58.18%
CYP2C9 inhibition	-	0.8256	82.56%
CYP2C19 inhibition	-	0.8376	83.76%
CYP2D6 inhibition	-	0.9213	92.13%
CYP1A2 inhibition	-	0.7005	70.05%
CYP2C8 inhibition	+	0.6713	67.13%
CYP inhibitory promiscuity	-	0.9055	90.55%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5871	58.71%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9233	92.33%
Skin irritation	-	0.6764	67.64%
Skin corrosion	-	0.9046	90.46%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7264	72.64%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.7561	75.61%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.6986	69.86%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.7402	74.02%
Androgen receptor binding	+	0.6440	64.40%
Thyroid receptor binding	+	0.6406	64.06%
Glucocorticoid receptor binding	+	0.6734	67.34%
Aromatase binding	+	0.6287	62.87%
PPAR gamma	+	0.6201	62.01%
Honey bee toxicity	-	0.7636	76.36%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9925	99.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.09%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.43%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.53%	91.11%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	91.75%	94.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.52%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	90.40%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	90.26%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.01%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.28%	94.62%
CHEMBL2581	P07339	Cathepsin D	87.07%	98.95%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.92%	83.00%
CHEMBL5028	O14672	ADAM10	84.86%	97.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.49%	95.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.29%	96.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.14%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.47%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.21%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.21%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.81%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.65%	91.07%

Plants that contains it

• Orthosiphon aristatus
• Orthosiphon aristatus var. aristatus

Cross-Links

• PubChem: 163081099
• LOTUS: LTS0205133
• wikiData: Q105367065