Dehydrozaluzanin C

Details

• Internal ID: d491269f-104d-4c64-9bb4-85593412d446
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6aR,9aR,9bS)-3,6,9-trimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2,8-dione
• SMILES (Canonical): C=C1CCC2C(C3C1CC(=O)C3=C)OC(=O)C2=C
• SMILES (Isomeric): C=C1CC[C@@H]2[C@@H]([C@@H]3[C@H]1CC(=O)C3=C)OC(=O)C2=C
• InChI: InChI=1S/C15H16O3/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h10-11,13-14H,1-6H2/t10-,11-,13-,14-/m0/s1
• InChI Key: KNQLJJDOGQIMMT-IMIFBBOLSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₃
• Molecular Weight: 244.28 g/mol
• Exact Mass: 244.109944368 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.20
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• CHEMBL2270297
• SCHEMBL17214360
• (3aS,6aR,9aR,9bS)-3,6,9-trimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2,8-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6360	63.60%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.8982	89.82%
OATP1B3 inhibitior	+	0.9468	94.68%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.8844	88.44%
P-glycoprotein inhibitior	-	0.8948	89.48%
P-glycoprotein substrate	-	0.8858	88.58%
CYP3A4 substrate	-	0.5465	54.65%
CYP2C9 substrate	-	0.8201	82.01%
CYP2D6 substrate	-	0.8449	84.49%
CYP3A4 inhibition	-	0.8765	87.65%
CYP2C9 inhibition	-	0.9105	91.05%
CYP2C19 inhibition	-	0.7754	77.54%
CYP2D6 inhibition	-	0.9288	92.88%
CYP1A2 inhibition	-	0.6039	60.39%
CYP2C8 inhibition	-	0.8513	85.13%
CYP inhibitory promiscuity	-	0.9206	92.06%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.6465	64.65%
Eye corrosion	-	0.6193	61.93%
Eye irritation	+	0.8654	86.54%
Skin irritation	-	0.6544	65.44%
Skin corrosion	-	0.9299	92.99%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6372	63.72%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.9250	92.50%
skin sensitisation	-	0.5757	57.57%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.7576	75.76%
Acute Oral Toxicity (c)	III	0.5604	56.04%
Estrogen receptor binding	-	0.6158	61.58%
Androgen receptor binding	+	0.5656	56.56%
Thyroid receptor binding	-	0.7131	71.31%
Glucocorticoid receptor binding	-	0.5338	53.38%
Aromatase binding	-	0.8208	82.08%
PPAR gamma	-	0.7481	74.81%
Honey bee toxicity	-	0.6648	66.48%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.9635	96.35%

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	92.48%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.74%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.68%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.36%	99.23%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.29%	96.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.11%	92.94%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.62%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.07%	95.89%
CHEMBL1978	P11511	Cytochrome P450 19A1	80.14%	91.76%

Plants that contains it

• Brachylaena discolor var. transvaalensis
• Cyanthillium patulum
• Munnozia maronii
• Paralychnophora bicolor
• Saussurea involucrata

Cross-Links

• PubChem: 10538257
• NPASS: NPC208223
• LOTUS: LTS0232564
• wikiData: Q105143527