Curcumenolactone B

Details

• Internal ID: 98ddefad-cf9d-41b3-8585-c161971eeb6f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4aR,5R,5aS,6aR)-3,5a-dimethyl-5-(3-oxobutyl)-4a,5,6,6a-tetrahydro-4H-cyclopropa[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=C2CC3C(C3(CC2OC1=O)C)CCC(=O)C
• SMILES (Isomeric): CC1=C2C[C@@H]3[C@H]([C@@]3(C[C@H]2OC1=O)C)CCC(=O)C
• InChI: InChI=1S/C15H20O3/c1-8(16)4-5-11-12-6-10-9(2)14(17)18-13(10)7-15(11,12)3/h11-13H,4-7H2,1-3H3/t11-,12-,13-,15+/m1/s1
• InChI Key: LWEBVMKVDYHHRS-BHPKHCPMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.64
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• (4Ar,5R,5aS,6aR)-3,5a-dimethyl-5-(3-oxobutyl)-4a,5,6,6a-tetrahydro-4H-cyclopropa[f][1]benzofuran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	+	0.8041	80.41%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6904	69.04%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.9075	90.75%
OATP1B3 inhibitior	+	0.9657	96.57%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.8612	86.12%
P-glycoprotein inhibitior	-	0.7612	76.12%
P-glycoprotein substrate	-	0.8344	83.44%
CYP3A4 substrate	+	0.5939	59.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9062	90.62%
CYP3A4 inhibition	-	0.7551	75.51%
CYP2C9 inhibition	-	0.8690	86.90%
CYP2C19 inhibition	-	0.8054	80.54%
CYP2D6 inhibition	-	0.9506	95.06%
CYP1A2 inhibition	+	0.5693	56.93%
CYP2C8 inhibition	-	0.8805	88.05%
CYP inhibitory promiscuity	-	0.8132	81.32%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5858	58.58%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.7628	76.28%
Skin irritation	+	0.5281	52.81%
Skin corrosion	-	0.8933	89.33%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3656	36.56%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.5783	57.83%
skin sensitisation	-	0.6313	63.13%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5805	58.05%
Acute Oral Toxicity (c)	III	0.6318	63.18%
Estrogen receptor binding	-	0.5829	58.29%
Androgen receptor binding	+	0.5433	54.33%
Thyroid receptor binding	-	0.5376	53.76%
Glucocorticoid receptor binding	+	0.5817	58.17%
Aromatase binding	-	0.8244	82.44%
PPAR gamma	-	0.6147	61.47%
Honey bee toxicity	-	0.8685	86.85%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9933	99.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.17%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.25%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.48%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.56%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.38%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	84.00%	91.19%
CHEMBL2581	P07339	Cathepsin D	83.62%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.25%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	81.90%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.01%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.48%	97.09%

Plants that contains it

• Curcuma zedoaria

Cross-Links

• PubChem: 10264037
• NPASS: NPC303728
• LOTUS: LTS0121928
• wikiData: Q105158229