methyl (1S,4aR,6R,7S,7aR)-6-hydroxy-7-[(1R)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 6278cc4c-8f71-40c6-8932-9660e6e5baef
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aR,6R,7S,7aR)-6-hydroxy-7-[(1R)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• InChI: InChI=1S/C28H35NO10/c1-36-26(35)16-11-37-27(39-28-25(34)24(33)23(32)19(10-30)38-28)21-15(16)9-18(31)20(21)14-7-4-6-13-12-5-2-3-8-17(12)29-22(13)14/h2-3,5,8,11,14-15,18-21,23-25,27-34H,4,6-7,9-10H2,1H3/t14-,15+,18-,19-,20-,21-,23-,24+,25-,27+,28+/m1/s1
• InChI Key: ZHFNEDGXVCJJIB-KIZNPYPLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₅NO₁₀
• Molecular Weight: 545.60 g/mol
• Exact Mass: 545.22609631 g/mol
• Topological Polar Surface Area (TPSA): 171.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.43
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8858	88.58%
Caco-2	-	0.8765	87.65%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.5630	56.30%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.7132	71.32%
OATP1B3 inhibitior	+	0.9527	95.27%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7812	78.12%
P-glycoprotein inhibitior	-	0.5286	52.86%
P-glycoprotein substrate	-	0.5165	51.65%
CYP3A4 substrate	+	0.7196	71.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8427	84.27%
CYP3A4 inhibition	-	0.8925	89.25%
CYP2C9 inhibition	-	0.7604	76.04%
CYP2C19 inhibition	-	0.7496	74.96%
CYP2D6 inhibition	-	0.8185	81.85%
CYP1A2 inhibition	-	0.5403	54.03%
CYP2C8 inhibition	+	0.7364	73.64%
CYP inhibitory promiscuity	-	0.5847	58.47%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6431	64.31%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9584	95.84%
Skin irritation	-	0.7988	79.88%
Skin corrosion	-	0.9428	94.28%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7532	75.32%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.5942	59.42%
skin sensitisation	-	0.8382	83.82%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6188	61.88%
Acute Oral Toxicity (c)	III	0.5578	55.78%
Estrogen receptor binding	+	0.8687	86.87%
Androgen receptor binding	+	0.6857	68.57%
Thyroid receptor binding	+	0.5568	55.68%
Glucocorticoid receptor binding	+	0.6722	67.22%
Aromatase binding	+	0.5806	58.06%
PPAR gamma	+	0.6562	65.62%
Honey bee toxicity	-	0.8150	81.50%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	-	0.4104	41.04%

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	99.56%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.91%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.59%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.15%	98.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	91.70%	95.83%
CHEMBL4040	P28482	MAP kinase ERK2	90.95%	83.82%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.25%	92.62%
CHEMBL5028	O14672	ADAM10	88.09%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.87%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.46%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.31%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.64%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.79%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.54%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.09%	86.92%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.95%	94.23%
CHEMBL2535	P11166	Glucose transporter	82.42%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.53%	99.17%
CHEMBL4208	P20618	Proteasome component C5	80.61%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.20%	95.50%

Plants that contains it

• Psychotria brachyceras

Cross-Links

• PubChem: 101110452
• LOTUS: LTS0144075
• wikiData: Q105375699