Zedoalactone B

Details

• Internal ID: da3fa7a4-e3b7-4578-9834-836249e14b24
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (5R,5aR,8S,8aR)-5,5a,8-trihydroxy-1,5,8-trimethyl-6,7,8a,9-tetrahydroazuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1=C2CC3C(CCC3(C(C=C2OC1=O)(C)O)O)(C)O
• SMILES (Isomeric): CC1=C2C[C@@H]3[C@@](CC[C@@]3([C@](C=C2OC1=O)(C)O)O)(C)O
• InChI: InChI=1S/C15H20O5/c1-8-9-6-11-13(2,17)4-5-15(11,19)14(3,18)7-10(9)20-12(8)16/h7,11,17-19H,4-6H2,1-3H3/t11-,13+,14-,15-/m1/s1
• InChI Key: HPNXJLIPUVXDNH-FAAHXZRKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.79
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• 170384-81-3
• CHEMBL2386514
• AKOS040735584
• E83701

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9521	95.21%
Caco-2	+	0.6468	64.68%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	-	0.8520	85.20%
OATP1B1 inhibitior	+	0.9158	91.58%
OATP1B3 inhibitior	+	0.9428	94.28%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6821	68.21%
BSEP inhibitior	-	0.8030	80.30%
P-glycoprotein inhibitior	-	0.9237	92.37%
P-glycoprotein substrate	-	0.8962	89.62%
CYP3A4 substrate	+	0.5677	56.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8796	87.96%
CYP3A4 inhibition	-	0.7646	76.46%
CYP2C9 inhibition	-	0.6374	63.74%
CYP2C19 inhibition	-	0.5739	57.39%
CYP2D6 inhibition	-	0.9417	94.17%
CYP1A2 inhibition	+	0.6353	63.53%
CYP2C8 inhibition	-	0.8812	88.12%
CYP inhibitory promiscuity	-	0.9582	95.82%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5231	52.31%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.7560	75.60%
Skin irritation	+	0.5659	56.59%
Skin corrosion	-	0.9102	91.02%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4905	49.05%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5504	55.04%
skin sensitisation	-	0.8332	83.32%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.4831	48.31%
Acute Oral Toxicity (c)	III	0.3007	30.07%
Estrogen receptor binding	+	0.7902	79.02%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6946	69.46%
Glucocorticoid receptor binding	+	0.5570	55.70%
Aromatase binding	-	0.6178	61.78%
PPAR gamma	+	0.6123	61.23%
Honey bee toxicity	-	0.9169	91.69%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9637	96.37%

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	93.38%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.25%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.44%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.17%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.71%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.04%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.87%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.99%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.33%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.24%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.52%	89.00%

Plants that contains it

• Curcuma aeruginosa
• Curcuma phaeocaulis
• Curcuma zedoaria

Cross-Links

• PubChem: 15226640
• NPASS: NPC40821
• ChEMBL: CHEMBL2386514
• LOTUS: LTS0236768
• wikiData: Q105031779