(1R,3S,4R,7S,8R,13R)-4-hydroxy-3,7-dimethyl-14-methylidene-15-oxo-16-oxatetracyclo[11.3.1.02,11.03,8]heptadec-2(11)-ene-7-carboxylic acid

Details

• Internal ID: a05ce89c-0a1c-4519-90b5-6c90711da6ca
• Taxonomy: Organoheterocyclic compounds > Lactones > Delta valerolactones
• IUPAC Name: (1R,3S,4R,7S,8R,13R)-4-hydroxy-3,7-dimethyl-14-methylidene-15-oxo-16-oxatetracyclo[11.3.1.02,11.03,8]heptadec-2(11)-ene-7-carboxylic acid
• SMILES (Canonical): CC1(CCC(C2(C1CCC3=C2C4CC(C3)C(=C)C(=O)O4)C)O)C(=O)O
• SMILES (Isomeric): C[C@@]1(CC[C@H]([C@]2([C@H]1CCC3=C2[C@H]4C[C@@H](C3)C(=C)C(=O)O4)C)O)C(=O)O
• InChI: InChI=1S/C20H26O5/c1-10-12-8-11-4-5-14-19(2,18(23)24)7-6-15(21)20(14,3)16(11)13(9-12)25-17(10)22/h12-15,21H,1,4-9H2,2-3H3,(H,23,24)/t12-,13-,14+,15-,19+,20-/m1/s1
• InChI Key: CGFRNNVBYXSTHE-POLNXRMTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₅
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.17802393 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.84
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9726	97.26%
Caco-2	+	0.5242	52.42%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8366	83.66%
OATP2B1 inhibitior	-	0.8642	86.42%
OATP1B1 inhibitior	+	0.8816	88.16%
OATP1B3 inhibitior	+	0.8731	87.31%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5832	58.32%
BSEP inhibitior	-	0.6471	64.71%
P-glycoprotein inhibitior	-	0.7352	73.52%
P-glycoprotein substrate	-	0.7368	73.68%
CYP3A4 substrate	+	0.6656	66.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8817	88.17%
CYP3A4 inhibition	-	0.5289	52.89%
CYP2C9 inhibition	-	0.9382	93.82%
CYP2C19 inhibition	-	0.9480	94.80%
CYP2D6 inhibition	-	0.9373	93.73%
CYP1A2 inhibition	-	0.8152	81.52%
CYP2C8 inhibition	-	0.6089	60.89%
CYP inhibitory promiscuity	-	0.9716	97.16%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6488	64.88%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.8791	87.91%
Skin irritation	+	0.5654	56.54%
Skin corrosion	-	0.9185	91.85%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6329	63.29%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5700	57.00%
skin sensitisation	-	0.7169	71.69%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6986	69.86%
Acute Oral Toxicity (c)	III	0.5975	59.75%
Estrogen receptor binding	+	0.7141	71.41%
Androgen receptor binding	+	0.5799	57.99%
Thyroid receptor binding	+	0.6477	64.77%
Glucocorticoid receptor binding	+	0.7746	77.46%
Aromatase binding	+	0.5820	58.20%
PPAR gamma	-	0.5872	58.72%
Honey bee toxicity	-	0.7882	78.82%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9935	99.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.78%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.09%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.85%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.82%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.05%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.02%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.53%	89.00%
CHEMBL1902	P62942	FK506-binding protein 1A	81.38%	97.05%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.05%	95.56%
CHEMBL5028	O14672	ADAM10	81.00%	97.50%

Plants that contains it

• Adenostemma brasilianum

Cross-Links

• PubChem: 162949801
• LOTUS: LTS0062687
• wikiData: Q104957611