3-[(2S,5aR,6S,7S,9aR,9bR)-2-hydroperoxy-6,9a,9b-trimethyl-7-prop-1-en-2-yl-1,2,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

Details

• Internal ID: b24553eb-e308-4098-902c-828a19663618
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Carbocyclic fatty acids
• IUPAC Name: 3-[(2S,5aR,6S,7S,9aR,9bR)-2-hydroperoxy-6,9a,9b-trimethyl-7-prop-1-en-2-yl-1,2,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
• SMILES (Canonical): CC(=C)C1CCC2(C(C1(C)CCC(=O)O)CCC3=CC(CC32C)OO)C
• SMILES (Isomeric): CC(=C)[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CCC(=O)O)CCC3=C[C@H](C[C@]32C)OO)C
• InChI: InChI=1S/C22H34O4/c1-14(2)17-8-11-21(4)18(20(17,3)10-9-19(23)24)7-6-15-12-16(26-25)13-22(15,21)5/h12,16-18,25H,1,6-11,13H2,2-5H3,(H,23,24)/t16-,17+,18-,20+,21-,22-/m1/s1
• InChI Key: JKZVRJBVBMTFCW-CHBSCGLWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₄
• Molecular Weight: 362.50 g/mol
• Exact Mass: 362.24570956 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 5.45
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9916	99.16%
Caco-2	+	0.7690	76.90%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6943	69.43%
OATP2B1 inhibitior	-	0.8666	86.66%
OATP1B1 inhibitior	+	0.8433	84.33%
OATP1B3 inhibitior	+	0.8208	82.08%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6791	67.91%
P-glycoprotein inhibitior	-	0.7246	72.46%
P-glycoprotein substrate	-	0.6128	61.28%
CYP3A4 substrate	+	0.6684	66.84%
CYP2C9 substrate	-	0.5886	58.86%
CYP2D6 substrate	-	0.8706	87.06%
CYP3A4 inhibition	-	0.6657	66.57%
CYP2C9 inhibition	-	0.8656	86.56%
CYP2C19 inhibition	-	0.8995	89.95%
CYP2D6 inhibition	-	0.9425	94.25%
CYP1A2 inhibition	-	0.8972	89.72%
CYP2C8 inhibition	+	0.5196	51.96%
CYP inhibitory promiscuity	-	0.8493	84.93%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6441	64.41%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9227	92.27%
Skin irritation	+	0.5507	55.07%
Skin corrosion	-	0.9247	92.47%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5310	53.10%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.6698	66.98%
skin sensitisation	-	0.7520	75.20%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.8370	83.70%
Acute Oral Toxicity (c)	III	0.4971	49.71%
Estrogen receptor binding	+	0.5301	53.01%
Androgen receptor binding	+	0.6517	65.17%
Thyroid receptor binding	+	0.7418	74.18%
Glucocorticoid receptor binding	+	0.8070	80.70%
Aromatase binding	+	0.7080	70.80%
PPAR gamma	+	0.6845	68.45%
Honey bee toxicity	-	0.8494	84.94%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7755	77.55%
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	98.25%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.22%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.15%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.21%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.65%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	88.45%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.80%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.16%	97.09%
CHEMBL5028	O14672	ADAM10	82.62%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.66%	95.56%

Plants that contains it

• Commiphora kua

Cross-Links

• PubChem: 162975301
• LOTUS: LTS0254436
• wikiData: Q105130596