5-[(3aR,4S,5R,7aR)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3H-inden-4-yl]-3-methylidene-4-oxopentanoic acid

Details

• Internal ID: f34c3a80-8c07-428d-8ace-a0a544472588
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: 5-[(3aR,4S,5R,7aR)-2-formyl-1,4,5,7a-tetramethyl-3a,5,6,7-tetrahydro-3H-inden-4-yl]-3-methylidene-4-oxopentanoic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)CC(=O)C(=C)CC(=O)O)CC(=C2C)C=O)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CC(=O)C(=C)CC(=O)O)CC(=C2C)C=O)C
• InChI: InChI=1S/C20H28O4/c1-12(8-18(23)24)16(22)10-20(5)13(2)6-7-19(4)14(3)15(11-21)9-17(19)20/h11,13,17H,1,6-10H2,2-5H3,(H,23,24)/t13-,17+,19+,20+/m1/s1
• InChI Key: GEYOTLVJLLCPMD-IKTSWFPUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.95
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9880	98.80%
Caco-2	+	0.5513	55.13%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6366	63.66%
OATP2B1 inhibitior	-	0.8630	86.30%
OATP1B1 inhibitior	+	0.8222	82.22%
OATP1B3 inhibitior	+	0.8850	88.50%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	-	0.6230	62.30%
P-glycoprotein inhibitior	-	0.6426	64.26%
P-glycoprotein substrate	-	0.7579	75.79%
CYP3A4 substrate	+	0.5799	57.99%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.9056	90.56%
CYP3A4 inhibition	-	0.7168	71.68%
CYP2C9 inhibition	-	0.9239	92.39%
CYP2C19 inhibition	-	0.9593	95.93%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.8656	86.56%
CYP2C8 inhibition	-	0.7136	71.36%
CYP inhibitory promiscuity	-	0.9480	94.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.6908	69.08%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.8874	88.74%
Skin irritation	+	0.6657	66.57%
Skin corrosion	-	0.9662	96.62%
Ames mutagenesis	-	0.7844	78.44%
Human Ether-a-go-go-Related Gene inhibition	+	0.6701	67.01%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5358	53.58%
skin sensitisation	+	0.5112	51.12%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7066	70.66%
Acute Oral Toxicity (c)	III	0.7305	73.05%
Estrogen receptor binding	+	0.6286	62.86%
Androgen receptor binding	+	0.5341	53.41%
Thyroid receptor binding	+	0.6728	67.28%
Glucocorticoid receptor binding	+	0.6688	66.88%
Aromatase binding	+	0.7479	74.79%
PPAR gamma	+	0.6464	64.64%
Honey bee toxicity	-	0.9011	90.11%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9964	99.64%

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	92.68%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.07%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.68%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	86.97%	91.19%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.72%	91.11%
CHEMBL5028	O14672	ADAM10	82.67%	97.50%
CHEMBL233	P35372	Mu opioid receptor	81.83%	97.93%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.79%	93.03%
CHEMBL221	P23219	Cyclooxygenase-1	81.77%	90.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.67%	95.50%

Plants that contains it

• Callicarpa pentandra

Cross-Links

• PubChem: 10688029
• LOTUS: LTS0170776
• wikiData: Q105007412