4,5-dihydroxy-3,9-dimethyl-6-methylidene-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione

Details

• Internal ID: f75eeaf0-28b8-43c3-9e45-fd195e839b3e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 4,5-dihydroxy-3,9-dimethyl-6-methylidene-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione
• SMILES (Canonical): CC1C2C(CC1=O)C(=C)C(C(C3C2OC(=O)C3C)O)O
• SMILES (Isomeric): CC1C2C(CC1=O)C(=C)C(C(C3C2OC(=O)C3C)O)O
• InChI: InChI=1S/C15H20O5/c1-5-8-4-9(16)6(2)10(8)14-11(13(18)12(5)17)7(3)15(19)20-14/h6-8,10-14,17-18H,1,4H2,2-3H3
• InChI Key: ZIYAVSIQJMDPSW-UHFFFAOYSA-N
• Popularity: 0 references 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): 83.80 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.30
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9224	92.24%
Caco-2	-	0.6060	60.60%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5707	57.07%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.9021	90.21%
OATP1B3 inhibitior	+	0.9457	94.57%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9532	95.32%
P-glycoprotein inhibitior	-	0.8996	89.96%
P-glycoprotein substrate	-	0.8732	87.32%
CYP3A4 substrate	+	0.5234	52.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8421	84.21%
CYP3A4 inhibition	-	0.8256	82.56%
CYP2C9 inhibition	-	0.8117	81.17%
CYP2C19 inhibition	-	0.7568	75.68%
CYP2D6 inhibition	-	0.9233	92.33%
CYP1A2 inhibition	-	0.6774	67.74%
CYP2C8 inhibition	-	0.9392	93.92%
CYP inhibitory promiscuity	-	0.9415	94.15%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5451	54.51%
Eye corrosion	-	0.9661	96.61%
Eye irritation	-	0.5676	56.76%
Skin irritation	-	0.5753	57.53%
Skin corrosion	-	0.8332	83.32%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7194	71.94%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.6533	65.33%
skin sensitisation	-	0.7760	77.60%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5495	54.95%
Acute Oral Toxicity (c)	II	0.3542	35.42%
Estrogen receptor binding	-	0.6342	63.42%
Androgen receptor binding	-	0.5406	54.06%
Thyroid receptor binding	+	0.5624	56.24%
Glucocorticoid receptor binding	-	0.5459	54.59%
Aromatase binding	-	0.7360	73.60%
PPAR gamma	-	0.8487	84.87%
Honey bee toxicity	-	0.7954	79.54%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5550	55.50%
Fish aquatic toxicity	+	0.9517	95.17%

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	91.39%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.91%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.01%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	86.31%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.17%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.74%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.35%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.29%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.22%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.15%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.00%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.59%	95.89%

Plants that contains it

• Volutaria tubuliflora

Cross-Links

• PubChem: 162980027
• LOTUS: LTS0206660
• wikiData: Q105377666