methyl (1S,4aS,6S,7R,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(3R,4aS,5R,6S)-5-ethenyl-1-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 6601e6e8-00c0-400b-940f-f923e53fbd82
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,6S,7R,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(3R,4aS,5R,6S)-5-ethenyl-1-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)COC4CC5C(C(OC=C5C(=O)O4)OC6C(C(C(C(O6)CO)O)O)O)C=C)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4C[C@H]5[C@H]([C@@H](OC=C5C(=O)O4)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C=C)O)O)O)O
• InChI: InChI=1S/C33H46O19/c1-4-12-13-6-20(50-29(43)15(13)8-46-30(12)51-32-26(40)24(38)22(36)18(7-34)48-32)45-10-19-23(37)25(39)27(41)33(49-19)52-31-21-11(2)17(35)5-14(21)16(9-47-31)28(42)44-3/h4,8-9,11-14,17-27,30-41H,1,5-7,10H2,2-3H3/t11-,12+,13-,14+,17-,18+,19+,20+,21+,22+,23+,24-,25-,26+,27+,30-,31-,32-,33-/m0/s1
• InChI Key: MMDKMJKYTLBHIS-KBCOMESHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₆O₁₉
• Molecular Weight: 746.70 g/mol
• Exact Mass: 746.26332923 g/mol
• Topological Polar Surface Area (TPSA): 279.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -3.38
• H-Bond Acceptor: 19
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6280	62.80%
Caco-2	-	0.8816	88.16%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6855	68.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3454	34.54%
OATP1B3 inhibitior	+	0.9502	95.02%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6698	66.98%
P-glycoprotein inhibitior	+	0.6408	64.08%
P-glycoprotein substrate	+	0.5159	51.59%
CYP3A4 substrate	+	0.6950	69.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8703	87.03%
CYP3A4 inhibition	-	0.7618	76.18%
CYP2C9 inhibition	-	0.9142	91.42%
CYP2C19 inhibition	-	0.8784	87.84%
CYP2D6 inhibition	-	0.9143	91.43%
CYP1A2 inhibition	-	0.8868	88.68%
CYP2C8 inhibition	+	0.6130	61.30%
CYP inhibitory promiscuity	-	0.9385	93.85%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6788	67.88%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9173	91.73%
Skin irritation	-	0.7023	70.23%
Skin corrosion	-	0.9365	93.65%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7372	73.72%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.6515	65.15%
skin sensitisation	-	0.8632	86.32%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6475	64.75%
Acute Oral Toxicity (c)	III	0.5535	55.35%
Estrogen receptor binding	+	0.8024	80.24%
Androgen receptor binding	+	0.6208	62.08%
Thyroid receptor binding	-	0.5546	55.46%
Glucocorticoid receptor binding	+	0.6428	64.28%
Aromatase binding	+	0.5745	57.45%
PPAR gamma	+	0.7288	72.88%
Honey bee toxicity	-	0.7165	71.65%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.8924	89.24%

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	97.06%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.73%	85.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	95.84%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.78%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.03%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	91.66%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	91.37%	95.83%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.88%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.91%	98.95%
CHEMBL4208	P20618	Proteasome component C5	86.65%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.08%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.09%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.41%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.40%	95.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.73%	91.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.74%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.85%	96.00%

Plants that contains it

• Acacia aulacocarpa
• Anemonastrum flaccidum
• Ardisia neriifolia
• Aspidosperma subincanum
• Cryptocarya aschersoniana
• Eupatorium argentinum
• Garcinia madruno
• Guatteria ucayalina
• Juniperus brevifolia
• Lonicera japonica
• Peritassa compta
• Psiadia dentata

Cross-Links

• PubChem: 11093859
• NPASS: NPC228329
• LOTUS: LTS0187232
• wikiData: Q105167607