[(1R,3R,3aS,4S,6R,8aR)-1,8-diacetyloxy-3,6-dihydroxy-6,8a-dimethyl-3-propan-2-yl-2,3a,4,5-tetrahydro-1H-azulen-4-yl] 4-methoxybenzoate

Details

• Internal ID: 4fedb04b-09ea-4ece-a670-b4b16f8308f2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,3R,3aS,4S,6R,8aR)-1,8-diacetyloxy-3,6-dihydroxy-6,8a-dimethyl-3-propan-2-yl-2,3a,4,5-tetrahydro-1H-azulen-4-yl] 4-methoxybenzoate
• SMILES (Canonical): CC(C)C1(CC(C2(C1C(CC(C=C2OC(=O)C)(C)O)OC(=O)C3=CC=C(C=C3)OC)C)OC(=O)C)O
• SMILES (Isomeric): CC(C)[C@@]1(C[C@H]([C@]2([C@H]1[C@H](C[C@@](C=C2OC(=O)C)(C)O)OC(=O)C3=CC=C(C=C3)OC)C)OC(=O)C)O
• InChI: InChI=1S/C27H36O9/c1-15(2)27(32)14-22(35-17(4)29)26(6)21(34-16(3)28)13-25(5,31)12-20(23(26)27)36-24(30)18-8-10-19(33-7)11-9-18/h8-11,13,15,20,22-23,31-32H,12,14H2,1-7H3/t20-,22+,23+,25+,26-,27+/m0/s1
• InChI Key: RZXUNWTYRWPUFW-UVWVJSBOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆O₉
• Molecular Weight: 504.60 g/mol
• Exact Mass: 504.23593272 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.17
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9926	99.26%
Caco-2	-	0.6198	61.98%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7105	71.05%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.8806	88.06%
OATP1B3 inhibitior	+	0.8615	86.15%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9106	91.06%
P-glycoprotein inhibitior	+	0.8353	83.53%
P-glycoprotein substrate	+	0.5316	53.16%
CYP3A4 substrate	+	0.6606	66.06%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8407	84.07%
CYP3A4 inhibition	-	0.7471	74.71%
CYP2C9 inhibition	-	0.6572	65.72%
CYP2C19 inhibition	-	0.6629	66.29%
CYP2D6 inhibition	-	0.9359	93.59%
CYP1A2 inhibition	-	0.5429	54.29%
CYP2C8 inhibition	+	0.4822	48.22%
CYP inhibitory promiscuity	-	0.9069	90.69%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8836	88.36%
Carcinogenicity (trinary)	Non-required	0.5577	55.77%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9123	91.23%
Skin irritation	-	0.6144	61.44%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6463	64.63%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.5551	55.51%
skin sensitisation	-	0.7457	74.57%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6075	60.75%
Acute Oral Toxicity (c)	II	0.4282	42.82%
Estrogen receptor binding	+	0.7765	77.65%
Androgen receptor binding	+	0.7121	71.21%
Thyroid receptor binding	+	0.6165	61.65%
Glucocorticoid receptor binding	+	0.7646	76.46%
Aromatase binding	+	0.6188	61.88%
PPAR gamma	+	0.6664	66.64%
Honey bee toxicity	-	0.8263	82.63%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9958	99.58%

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	99.19%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.85%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	94.64%	90.17%
CHEMBL4208	P20618	Proteasome component C5	94.35%	90.00%
CHEMBL2581	P07339	Cathepsin D	91.31%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.37%	97.09%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	88.35%	94.97%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.51%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	85.96%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.58%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.37%	96.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.33%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.46%	95.56%
CHEMBL1907	P15144	Aminopeptidase N	84.08%	93.31%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.64%	82.69%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.24%	94.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.18%	90.24%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.12%	97.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.90%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.70%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.68%	95.89%
CHEMBL2535	P11166	Glucose transporter	80.97%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.46%	97.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.42%	96.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.27%	93.99%

Plants that contains it

• Ferula vesceritensis

Cross-Links

• PubChem: 163020808
• LOTUS: LTS0014736
• wikiData: Q105248698