[(1S,3R,4S,5S,6S)-4-[(1S,3aR,7aR)-1-hydroxy-7,7-dimethyl-1,3,4,5,6,7a-hexahydro-2-benzofuran-3a-yl]-5-formyl-3-hydroxy-7-methylidene-6-bicyclo[3.2.1]octanyl] acetate

Details

• Internal ID: bffeeed2-8c05-4aa6-8e63-a8dc7e5788fe
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Kaurane diterpenoids
• IUPAC Name: [(1S,3R,4S,5S,6S)-4-[(1S,3aR,7aR)-1-hydroxy-7,7-dimethyl-1,3,4,5,6,7a-hexahydro-2-benzofuran-3a-yl]-5-formyl-3-hydroxy-7-methylidene-6-bicyclo[3.2.1]octanyl] acetate
• SMILES (Canonical): CC(=O)OC1C(=C)C2CC(C(C1(C2)C=O)C34CCCC(C3C(OC4)O)(C)C)O
• SMILES (Isomeric): CC(=O)O[C@H]1C(=C)[C@@H]2C[C@H]([C@H]([C@]1(C2)C=O)[C@]34CCCC([C@H]3[C@H](OC4)O)(C)C)O
• InChI: InChI=1S/C22H32O6/c1-12-14-8-15(25)16(22(9-14,10-23)18(12)28-13(2)24)21-7-5-6-20(3,4)17(21)19(26)27-11-21/h10,14-19,25-26H,1,5-9,11H2,2-4H3/t14-,15-,16+,17-,18+,19+,21-,22+/m1/s1
• InChI Key: QJZOXQHFHPMHSM-YOCKPUNUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₆
• Molecular Weight: 392.50 g/mol
• Exact Mass: 392.21988874 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.22
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9902	99.02%
Caco-2	-	0.6017	60.17%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8354	83.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7996	79.96%
OATP1B3 inhibitior	+	0.8783	87.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8407	84.07%
BSEP inhibitior	-	0.6411	64.11%
P-glycoprotein inhibitior	-	0.6652	66.52%
P-glycoprotein substrate	-	0.5813	58.13%
CYP3A4 substrate	+	0.7099	70.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8626	86.26%
CYP3A4 inhibition	-	0.7052	70.52%
CYP2C9 inhibition	-	0.6082	60.82%
CYP2C19 inhibition	-	0.8189	81.89%
CYP2D6 inhibition	-	0.9447	94.47%
CYP1A2 inhibition	-	0.7872	78.72%
CYP2C8 inhibition	+	0.5245	52.45%
CYP inhibitory promiscuity	-	0.8779	87.79%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5792	57.92%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9447	94.47%
Skin irritation	-	0.5510	55.10%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6774	67.74%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8451	84.51%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.8289	82.89%
Acute Oral Toxicity (c)	I	0.5593	55.93%
Estrogen receptor binding	+	0.7624	76.24%
Androgen receptor binding	+	0.6453	64.53%
Thyroid receptor binding	+	0.6025	60.25%
Glucocorticoid receptor binding	+	0.7886	78.86%
Aromatase binding	+	0.6255	62.55%
PPAR gamma	-	0.4851	48.51%
Honey bee toxicity	-	0.6272	62.72%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.61%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.58%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.63%	96.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.88%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.15%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.05%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	86.45%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.59%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.22%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.12%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.09%	95.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.82%	95.71%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.76%	89.34%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.72%	98.75%
CHEMBL5028	O14672	ADAM10	82.96%	97.50%
CHEMBL259	P32245	Melanocortin receptor 4	82.75%	95.38%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.66%	82.50%
CHEMBL1937	Q92769	Histone deacetylase 2	82.16%	94.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.11%	89.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.10%	82.69%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.77%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.76%	96.77%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.47%	97.28%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	81.15%	94.97%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.41%	91.24%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.40%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.16%	97.09%

Plants that contains it

• Isodon sculponeatus

Cross-Links

• PubChem: 101536711
• LOTUS: LTS0265170
• wikiData: Q105222990