[(2R,3S,4S,5R,6R)-6-[[(3aS,6S,6aR,9aR,9bS)-6a-hydroxy-6-methyl-3-methylidene-2,7-dioxo-3a,4,5,6,9a,9b-hexahydroazuleno[8,7-b]furan-9-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate

Details

• Internal ID: b092f0b0-af1a-4196-8bc3-933c94e99a5c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(3aS,6S,6aR,9aR,9bS)-6a-hydroxy-6-methyl-3-methylidene-2,7-dioxo-3a,4,5,6,9a,9b-hexahydroazuleno[8,7-b]furan-9-yl]methoxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate
• SMILES (Canonical): CC1CCC2C(C3C1(C(=O)C=C3COC4C(C(C(C(O4)COC(=O)CC5=CC=C(C=C5)O)O)O)O)O)OC(=O)C2=C
• SMILES (Isomeric): C[C@H]1CC[C@@H]2[C@@H]([C@@H]3[C@]1(C(=O)C=C3CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)CC5=CC=C(C=C5)O)O)O)O)O)OC(=O)C2=C
• InChI: InChI=1S/C29H34O12/c1-13-3-8-18-14(2)27(36)41-26(18)22-16(10-20(31)29(13,22)37)11-39-28-25(35)24(34)23(33)19(40-28)12-38-21(32)9-15-4-6-17(30)7-5-15/h4-7,10,13,18-19,22-26,28,30,33-35,37H,2-3,8-9,11-12H2,1H3/t13-,18-,19+,22+,23+,24-,25+,26-,28+,29-/m0/s1
• InChI Key: CVJWQIVIVIAFKM-DZVSTWMOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₂
• Molecular Weight: 574.60 g/mol
• Exact Mass: 574.20502652 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.31
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8280	82.80%
Caco-2	-	0.8818	88.18%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7946	79.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7883	78.83%
OATP1B3 inhibitior	+	0.9346	93.46%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8271	82.71%
BSEP inhibitior	-	0.6065	60.65%
P-glycoprotein inhibitior	+	0.5913	59.13%
P-glycoprotein substrate	-	0.5201	52.01%
CYP3A4 substrate	+	0.6969	69.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8947	89.47%
CYP3A4 inhibition	-	0.9044	90.44%
CYP2C9 inhibition	-	0.7535	75.35%
CYP2C19 inhibition	-	0.6651	66.51%
CYP2D6 inhibition	-	0.8881	88.81%
CYP1A2 inhibition	-	0.7577	75.77%
CYP2C8 inhibition	+	0.7383	73.83%
CYP inhibitory promiscuity	-	0.7747	77.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5487	54.87%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9285	92.85%
Skin irritation	-	0.6918	69.18%
Skin corrosion	-	0.9229	92.29%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4214	42.14%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5906	59.06%
skin sensitisation	-	0.8376	83.76%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7319	73.19%
Acute Oral Toxicity (c)	III	0.4311	43.11%
Estrogen receptor binding	+	0.7874	78.74%
Androgen receptor binding	+	0.7156	71.56%
Thyroid receptor binding	-	0.5482	54.82%
Glucocorticoid receptor binding	+	0.6031	60.31%
Aromatase binding	+	0.6623	66.23%
PPAR gamma	+	0.6415	64.15%
Honey bee toxicity	-	0.7721	77.21%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5750	57.50%
Fish aquatic toxicity	+	0.9948	99.48%

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	98.33%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.89%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.07%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.78%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.70%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.64%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.70%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.77%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.01%	86.33%
CHEMBL5957	P21589	5'-nucleotidase	86.78%	97.78%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.42%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.92%	97.25%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.89%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.61%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	81.90%	92.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.03%	97.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.76%	89.00%

Plants that contains it

• Crepidiastrum lanceolatum

Cross-Links

• PubChem: 163187549
• LOTUS: LTS0199417
• wikiData: Q104970794