4-O-[5-[5-(acetyloxymethyl)-3,7-dihydroxy-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enyl] 1-O-methyl butanedioate

Details

• Internal ID: 74b41699-cf93-4574-a4c8-275dc349841b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 4-O-[5-[5-(acetyloxymethyl)-3,7-dihydroxy-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enyl] 1-O-methyl butanedioate
• SMILES (Canonical): CC1=C(C2(CC(CC(C2CC1O)(C)COC(=O)C)O)C)CCC(=CCOC(=O)CCC(=O)OC)C
• SMILES (Isomeric): CC1=C(C2(CC(CC(C2CC1O)(C)COC(=O)C)O)C)CCC(=CCOC(=O)CCC(=O)OC)C
• InChI: InChI=1S/C27H42O8/c1-17(11-12-34-25(32)10-9-24(31)33-6)7-8-21-18(2)22(30)13-23-26(4,16-35-19(3)28)14-20(29)15-27(21,23)5/h11,20,22-23,29-30H,7-10,12-16H2,1-6H3
• InChI Key: OIQLMPQXNLUPFH-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₂O₈
• Molecular Weight: 494.60 g/mol
• Exact Mass: 494.28796829 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.64
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9698	96.98%
Caco-2	-	0.6892	68.92%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8748	87.48%
OATP2B1 inhibitior	-	0.5711	57.11%
OATP1B1 inhibitior	+	0.8569	85.69%
OATP1B3 inhibitior	+	0.8965	89.65%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6114	61.14%
BSEP inhibitior	+	0.9824	98.24%
P-glycoprotein inhibitior	+	0.7382	73.82%
P-glycoprotein substrate	+	0.5458	54.58%
CYP3A4 substrate	+	0.6908	69.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8465	84.65%
CYP3A4 inhibition	-	0.7843	78.43%
CYP2C9 inhibition	-	0.9243	92.43%
CYP2C19 inhibition	-	0.9193	91.93%
CYP2D6 inhibition	-	0.9174	91.74%
CYP1A2 inhibition	-	0.8659	86.59%
CYP2C8 inhibition	+	0.6274	62.74%
CYP inhibitory promiscuity	-	0.9142	91.42%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6847	68.47%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.8990	89.90%
Skin irritation	-	0.5646	56.46%
Skin corrosion	-	0.9755	97.55%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6927	69.27%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.6447	64.47%
skin sensitisation	-	0.8481	84.81%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.5777	57.77%
Acute Oral Toxicity (c)	III	0.7285	72.85%
Estrogen receptor binding	+	0.6737	67.37%
Androgen receptor binding	+	0.5524	55.24%
Thyroid receptor binding	-	0.5381	53.81%
Glucocorticoid receptor binding	+	0.7356	73.56%
Aromatase binding	+	0.6811	68.11%
PPAR gamma	+	0.5915	59.15%
Honey bee toxicity	-	0.6289	62.89%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9877	98.77%

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	97.84%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.98%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.97%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	94.38%	91.19%
CHEMBL3437	Q16853	Amine oxidase, copper containing	89.64%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.32%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	89.18%	94.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.00%	96.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.54%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	88.46%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.98%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.41%	96.38%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.51%	97.21%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.44%	91.07%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.11%	95.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.82%	96.90%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.35%	86.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.89%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.75%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.60%	100.00%
CHEMBL299	P17252	Protein kinase C alpha	80.00%	98.03%

Plants that contains it

• Acamptopappus sphaerocephalus

Cross-Links

• PubChem: 163092219
• LOTUS: LTS0251587
• wikiData: Q105192673