4-hydroxy-9-methyl-3,6-dimethylidene-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 595dddb1-3937-48ba-b8ca-e4e0ac6d0f1d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 4-hydroxy-9-methyl-3,6-dimethylidene-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one
• InChI: InChI=1S/C21H30O9/c1-7-4-11(23)15-9(3)20(27)30-19(15)14-8(2)12(5-10(7)14)28-21-18(26)17(25)16(24)13(6-22)29-21/h8,10-19,21-26H,1,3-6H2,2H3
• InChI Key: RCVYIXYBIBLTSJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₉
• Molecular Weight: 426.50 g/mol
• Exact Mass: 426.18898253 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.14
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7585	75.85%
Caco-2	-	0.7969	79.69%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6357	63.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7955	79.55%
OATP1B3 inhibitior	+	0.9653	96.53%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7704	77.04%
P-glycoprotein inhibitior	-	0.7965	79.65%
P-glycoprotein substrate	-	0.7254	72.54%
CYP3A4 substrate	+	0.6369	63.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8741	87.41%
CYP3A4 inhibition	-	0.8960	89.60%
CYP2C9 inhibition	-	0.9021	90.21%
CYP2C19 inhibition	-	0.8685	86.85%
CYP2D6 inhibition	-	0.9194	91.94%
CYP1A2 inhibition	-	0.8333	83.33%
CYP2C8 inhibition	-	0.8079	80.79%
CYP inhibitory promiscuity	-	0.8964	89.64%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7245	72.45%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9155	91.55%
Skin irritation	-	0.7085	70.85%
Skin corrosion	-	0.9331	93.31%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6700	67.00%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6446	64.46%
skin sensitisation	-	0.8523	85.23%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5681	56.81%
Acute Oral Toxicity (c)	III	0.5090	50.90%
Estrogen receptor binding	+	0.7281	72.81%
Androgen receptor binding	-	0.4840	48.40%
Thyroid receptor binding	+	0.5947	59.47%
Glucocorticoid receptor binding	-	0.4868	48.68%
Aromatase binding	+	0.6619	66.19%
PPAR gamma	-	0.5150	51.50%
Honey bee toxicity	-	0.6776	67.76%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8791	87.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.40%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.00%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.70%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.69%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.69%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.24%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.49%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	85.66%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.89%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.66%	95.83%
CHEMBL2996	Q05655	Protein kinase C delta	80.74%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.27%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.25%	99.23%

Plants that contains it

• Crepis pyrenaica

Cross-Links

• PubChem: 162944348
• LOTUS: LTS0021281
• wikiData: Q105234009