[(1R,2R,3E,5S,8E)-5-hydroxy-5,9-dimethyl-2-propan-2-ylcyclodeca-3,8-dien-1-yl] 4-hydroxybenzoate

Details

• Internal ID: b293493e-493c-495c-8e0f-dbbcf7bb987d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Germacrane sesquiterpenoids
• IUPAC Name: [(1R,2R,3E,5S,8E)-5-hydroxy-5,9-dimethyl-2-propan-2-ylcyclodeca-3,8-dien-1-yl] 4-hydroxybenzoate
• SMILES (Canonical): CC1=CCCC(C=CC(C(C1)OC(=O)C2=CC=C(C=C2)O)C(C)C)(C)O
• SMILES (Isomeric): C/C/1=C\CC[C@](/C=C/[C@H]([C@@H](C1)OC(=O)C2=CC=C(C=C2)O)C(C)C)(C)O
• InChI: InChI=1S/C22H30O4/c1-15(2)19-11-13-22(4,25)12-5-6-16(3)14-20(19)26-21(24)17-7-9-18(23)10-8-17/h6-11,13,15,19-20,23,25H,5,12,14H2,1-4H3/b13-11+,16-6+/t19-,20+,22-/m0/s1
• InChI Key: AVRRAMZPNSQDIW-SADMIFJPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₄
• Molecular Weight: 358.50 g/mol
• Exact Mass: 358.21440943 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.63
• H-Bond Acceptor: 4
• 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	+	0.9973	99.73%
Caco-2	+	0.6282	62.82%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8835	88.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8866	88.66%
OATP1B3 inhibitior	+	0.8829	88.29%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.5603	56.03%
P-glycoprotein inhibitior	-	0.6000	60.00%
P-glycoprotein substrate	-	0.5895	58.95%
CYP3A4 substrate	+	0.6434	64.34%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8387	83.87%
CYP3A4 inhibition	-	0.6383	63.83%
CYP2C9 inhibition	-	0.7167	71.67%
CYP2C19 inhibition	-	0.7259	72.59%
CYP2D6 inhibition	-	0.9363	93.63%
CYP1A2 inhibition	-	0.6445	64.45%
CYP2C8 inhibition	+	0.6513	65.13%
CYP inhibitory promiscuity	-	0.8770	87.70%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8282	82.82%
Carcinogenicity (trinary)	Non-required	0.6447	64.47%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9253	92.53%
Skin irritation	-	0.5627	56.27%
Skin corrosion	-	0.9775	97.75%
Ames mutagenesis	-	0.6670	66.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7158	71.58%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5805	58.05%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6366	63.66%
Acute Oral Toxicity (c)	III	0.5369	53.69%
Estrogen receptor binding	+	0.7128	71.28%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.7429	74.29%
Glucocorticoid receptor binding	+	0.6866	68.66%
Aromatase binding	+	0.6630	66.30%
PPAR gamma	+	0.5328	53.28%
Honey bee toxicity	-	0.8581	85.81%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5350	53.50%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.77%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.35%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	95.31%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.82%	91.11%
CHEMBL4208	P20618	Proteasome component C5	91.79%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.58%	95.89%
CHEMBL2996	Q05655	Protein kinase C delta	90.24%	97.79%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	90.06%	94.97%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.70%	97.25%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	89.60%	97.53%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.57%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	84.47%	90.17%
CHEMBL242	Q92731	Estrogen receptor beta	84.29%	98.35%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.66%	85.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.00%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.87%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	81.56%	91.19%
CHEMBL2535	P11166	Glucose transporter	81.49%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.45%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.31%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.89%	91.07%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.84%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.64%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.53%	90.71%

Plants that contains it

• Ferula pallida

Cross-Links

• PubChem: 6351580
• LOTUS: LTS0006522
• wikiData: Q104919762