[(4S,4aS,5'S,6R,7S,8R,8aS)-4-(chloromethyl)-5'-(furan-3-yl)-4,6-dihydroxy-7-methyl-2',3,5-trioxospiro[2,6,7,8a-tetrahydro-1H-naphthalene-8,3'-oxolane]-4a-yl]methyl acetate

Details

• Internal ID: 7c6747ec-55da-46cc-99c7-a3cb114625c2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(4S,4aS,5'S,6R,7S,8R,8aS)-4-(chloromethyl)-5'-(furan-3-yl)-4,6-dihydroxy-7-methyl-2',3,5-trioxospiro[2,6,7,8a-tetrahydro-1H-naphthalene-8,3'-oxolane]-4a-yl]methyl acetate
• InChI: InChI=1S/C22H25ClO9/c1-11-17(26)18(27)21(10-31-12(2)24)15(3-4-16(25)22(21,29)9-23)20(11)7-14(32-19(20)28)13-5-6-30-8-13/h5-6,8,11,14-15,17,26,29H,3-4,7,9-10H2,1-2H3/t11-,14+,15-,17-,20+,21+,22-/m1/s1
• InChI Key: MOTQKGQROGKJJP-WEVNQPJTSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₅ClO₉
• Molecular Weight: 468.90 g/mol
• Exact Mass: 468.1187101 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9754	97.54%
Caco-2	-	0.7355	73.55%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8554	85.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7992	79.92%
OATP1B3 inhibitior	+	0.9115	91.15%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7537	75.37%
BSEP inhibitior	-	0.4638	46.38%
P-glycoprotein inhibitior	-	0.5151	51.51%
P-glycoprotein substrate	-	0.5729	57.29%
CYP3A4 substrate	+	0.6876	68.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8325	83.25%
CYP3A4 inhibition	-	0.6872	68.72%
CYP2C9 inhibition	-	0.8083	80.83%
CYP2C19 inhibition	-	0.7742	77.42%
CYP2D6 inhibition	-	0.9344	93.44%
CYP1A2 inhibition	-	0.8878	88.78%
CYP2C8 inhibition	+	0.5760	57.60%
CYP inhibitory promiscuity	-	0.8614	86.14%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.4568	45.68%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9522	95.22%
Skin irritation	-	0.7387	73.87%
Skin corrosion	-	0.9339	93.39%
Ames mutagenesis	+	0.5746	57.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7908	79.08%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.9206	92.06%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.5573	55.73%
Acute Oral Toxicity (c)	I	0.3531	35.31%
Estrogen receptor binding	+	0.8165	81.65%
Androgen receptor binding	+	0.6948	69.48%
Thyroid receptor binding	-	0.4893	48.93%
Glucocorticoid receptor binding	+	0.8139	81.39%
Aromatase binding	+	0.6643	66.43%
PPAR gamma	-	0.5707	57.07%
Honey bee toxicity	-	0.7870	78.70%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9824	98.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.80%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.23%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	92.70%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.53%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.06%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.35%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.96%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.95%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.24%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.23%	92.62%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.62%	94.80%

Plants that contains it

• Teucrium racemosum

Cross-Links

• PubChem: 15226270
• LOTUS: LTS0135791
• wikiData: Q105169151