4-[2-[(1R,5R,8aS)-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one

Details

• Internal ID: a2640780-9e19-41f3-8f8a-687c8fbfe975
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: 4-[2-[(1R,5R,8aS)-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one
• SMILES (Canonical): CC1(CCCC2(C1CCC(=C)C2CCC3=CCOC3=O)C)COC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C[C@]1(CCC[C@@]2(C1CCC(=C)[C@H]2CCC3=CCOC3=O)C)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C26H40O8/c1-15-5-8-19-25(2,14-33-24-22(30)21(29)20(28)18(13-27)34-24)10-4-11-26(19,3)17(15)7-6-16-9-12-32-23(16)31/h9,17-22,24,27-30H,1,4-8,10-14H2,2-3H3/t17-,18-,19?,20-,21+,22-,24-,25+,26+/m1/s1
• InChI Key: YGCYRQKJYWQXHG-XWISJEPMSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₀O₈
• Molecular Weight: 480.60 g/mol
• Exact Mass: 480.27231823 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 1.85
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• CHEMBL1316546
• HMS2268C16
• SMR001215697

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7024	70.24%
Caco-2	-	0.7646	76.46%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8090	80.90%
OATP2B1 inhibitior	-	0.5761	57.61%
OATP1B1 inhibitior	+	0.8398	83.98%
OATP1B3 inhibitior	+	0.9053	90.53%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.5901	59.01%
P-glycoprotein inhibitior	-	0.4758	47.58%
P-glycoprotein substrate	-	0.7222	72.22%
CYP3A4 substrate	+	0.6940	69.40%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8853	88.53%
CYP3A4 inhibition	-	0.9320	93.20%
CYP2C9 inhibition	-	0.9133	91.33%
CYP2C19 inhibition	-	0.8991	89.91%
CYP2D6 inhibition	-	0.9279	92.79%
CYP1A2 inhibition	-	0.8680	86.80%
CYP2C8 inhibition	+	0.5556	55.56%
CYP inhibitory promiscuity	-	0.8937	89.37%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6395	63.95%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9391	93.91%
Skin irritation	-	0.5556	55.56%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7587	75.87%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9036	90.36%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6940	69.40%
Acute Oral Toxicity (c)	I	0.5110	51.10%
Estrogen receptor binding	+	0.7226	72.26%
Androgen receptor binding	+	0.6971	69.71%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6289	62.89%
Aromatase binding	+	0.6685	66.85%
PPAR gamma	+	0.6458	64.58%
Honey bee toxicity	-	0.7614	76.14%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9787	97.87%

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	99.25%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.94%	97.25%
CHEMBL2581	P07339	Cathepsin D	96.52%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.16%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.71%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.09%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.76%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.15%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.24%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.93%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.44%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	84.04%	92.50%
CHEMBL1977	P11473	Vitamin D receptor	83.27%	99.43%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.15%	95.50%
CHEMBL1937	Q92769	Histone deacetylase 2	82.69%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.30%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.20%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.13%	94.00%
CHEMBL5028	O14672	ADAM10	81.90%	97.50%
CHEMBL226	P30542	Adenosine A1 receptor	81.75%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	81.57%	94.73%

Plants that contains it

• Andrographis paniculata
• Scutellaria barbata

Cross-Links

• PubChem: 24980083
• NPASS: NPC392
• ChEMBL: CHEMBL1316546