caucanolide F

Details

• Internal ID: cdfdc92c-604c-49cc-b0f3-e7ebdb3b756d
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: 2-[2-[(2R)-2-[(2S,3Z)-2-methoxy-2-methyl-3-(4-methyl-5-oxofuran-2-ylidene)propyl]-5-oxo-2H-furan-4-yl]ethyl]-3-methylbut-2-enal
• SMILES (Canonical): CC1=CC(=CC(C)(CC2C=C(C(=O)O2)CCC(=C(C)C)C=O)OC)OC1=O
• SMILES (Isomeric): CC1=C/C(=C/[C@](C)(C[C@@H]2C=C(C(=O)O2)CCC(=C(C)C)C=O)OC)/OC1=O
• InChI: InChI=1S/C21H26O6/c1-13(2)16(12-22)7-6-15-9-18(27-20(15)24)11-21(4,25-5)10-17-8-14(3)19(23)26-17/h8-10,12,18H,6-7,11H2,1-5H3/b17-10-/t18-,21+/m0/s1
• InChI Key: MSDPTAGLGJLKRT-GQQAKVJGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₆
• Molecular Weight: 374.40 g/mol
• Exact Mass: 374.17293854 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.34
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 8

Synonyms

• CHEMBL516681

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	+	0.5522	55.22%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7171	71.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8417	84.17%
OATP1B3 inhibitior	+	0.8669	86.69%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.9063	90.63%
P-glycoprotein inhibitior	+	0.5894	58.94%
P-glycoprotein substrate	-	0.6222	62.22%
CYP3A4 substrate	+	0.6324	63.24%
CYP2C9 substrate	+	0.5991	59.91%
CYP2D6 substrate	-	0.8760	87.60%
CYP3A4 inhibition	-	0.8455	84.55%
CYP2C9 inhibition	-	0.8046	80.46%
CYP2C19 inhibition	-	0.8063	80.63%
CYP2D6 inhibition	-	0.9452	94.52%
CYP1A2 inhibition	-	0.7416	74.16%
CYP2C8 inhibition	+	0.4441	44.41%
CYP inhibitory promiscuity	-	0.8751	87.51%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8428	84.28%
Carcinogenicity (trinary)	Non-required	0.5637	56.37%
Eye corrosion	-	0.9734	97.34%
Eye irritation	-	0.9371	93.71%
Skin irritation	-	0.5961	59.61%
Skin corrosion	-	0.9253	92.53%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4904	49.04%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5531	55.31%
skin sensitisation	-	0.7280	72.80%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	-	0.6222	62.22%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.6767	67.67%
Acute Oral Toxicity (c)	III	0.6002	60.02%
Estrogen receptor binding	+	0.5491	54.91%
Androgen receptor binding	+	0.5846	58.46%
Thyroid receptor binding	+	0.6100	61.00%
Glucocorticoid receptor binding	+	0.7697	76.97%
Aromatase binding	-	0.5898	58.98%
PPAR gamma	+	0.6492	64.92%
Honey bee toxicity	-	0.4818	48.18%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9420	94.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.14%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.00%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.94%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.71%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	92.22%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.76%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.13%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.76%	85.14%
CHEMBL1902	P62942	FK506-binding protein 1A	85.67%	97.05%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.42%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.03%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.37%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.00%	99.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11552520
• LOTUS: LTS0107946
• wikiData: Q105171110