Curcumanolide B

Details

• Internal ID: 8b5c3374-cf61-4e61-afed-8aae9b1a5990
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (5R,6S,9R)-6-methyl-3-propan-2-ylidene-9-prop-1-en-2-yl-1-oxaspiro[4.4]nonan-2-one
• SMILES (Canonical): CC1CCC(C12CC(=C(C)C)C(=O)O2)C(=C)C
• SMILES (Isomeric): C[C@H]1CC[C@@H]([C@@]12CC(=C(C)C)C(=O)O2)C(=C)C
• InChI: InChI=1S/C15H22O2/c1-9(2)12-8-15(17-14(12)16)11(5)6-7-13(15)10(3)4/h11,13H,3,6-8H2,1-2,4-5H3/t11-,13+,15+/m0/s1
• InChI Key: KHOTZHZBHNDKOB-NJZAAPMLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33 g/mol
• Exact Mass: 234.161979940 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.63
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• Curcumanolides B
• CHEMBL2332434

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9926	99.26%
Caco-2	+	0.8322	83.22%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5378	53.78%
OATP2B1 inhibitior	-	0.8497	84.97%
OATP1B1 inhibitior	+	0.9337	93.37%
OATP1B3 inhibitior	-	0.2538	25.38%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.8126	81.26%
P-glycoprotein inhibitior	-	0.9023	90.23%
P-glycoprotein substrate	-	0.8927	89.27%
CYP3A4 substrate	+	0.5360	53.60%
CYP2C9 substrate	-	0.6075	60.75%
CYP2D6 substrate	-	0.8830	88.30%
CYP3A4 inhibition	-	0.8083	80.83%
CYP2C9 inhibition	-	0.9201	92.01%
CYP2C19 inhibition	+	0.5442	54.42%
CYP2D6 inhibition	-	0.9483	94.83%
CYP1A2 inhibition	+	0.6102	61.02%
CYP2C8 inhibition	-	0.9201	92.01%
CYP inhibitory promiscuity	-	0.9288	92.88%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5661	56.61%
Eye corrosion	-	0.9539	95.39%
Eye irritation	+	0.7611	76.11%
Skin irritation	+	0.6259	62.59%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.7070	70.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5366	53.66%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	+	0.5844	58.44%
skin sensitisation	+	0.6637	66.37%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	-	0.7111	71.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	+	0.9034	90.34%
Acute Oral Toxicity (c)	III	0.7308	73.08%
Estrogen receptor binding	-	0.6684	66.84%
Androgen receptor binding	-	0.5348	53.48%
Thyroid receptor binding	-	0.6023	60.23%
Glucocorticoid receptor binding	-	0.7488	74.88%
Aromatase binding	-	0.7934	79.34%
PPAR gamma	-	0.7533	75.33%
Honey bee toxicity	-	0.9165	91.65%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9863	98.63%

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	96.00%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	91.95%	91.49%
CHEMBL2581	P07339	Cathepsin D	91.93%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.69%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.66%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.61%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.31%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.24%	96.09%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.51%	97.33%
CHEMBL299	P17252	Protein kinase C alpha	81.10%	98.03%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.86%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.77%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.00%	97.09%

Plants that contains it

• Curcuma heyneana
• Curcuma zedoaria

Cross-Links

• PubChem: 14191394
• NPASS: NPC53581
• LOTUS: LTS0154162
• wikiData: Q104376016