Trichaspside C

Details

• Internal ID: 5857c86c-95b3-4631-bfb8-034899112e64
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Aminosaccharides > N-acyl-alpha-hexosamines
• IUPAC Name: N-[(2S,3R,4R,5S,6R)-2-[1-[(2R,4S,4aR,8aS)-4,7-dimethyl-3,4,4a,5,6,8a-hexahydro-2H-chromen-2-yl]propan-2-yloxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• SMILES (Canonical): CC1CC(OC2C1CCC(=C2)C)CC(C)OC3C(C(C(C(O3)CO)O)O)NC(=O)C
• SMILES (Isomeric): C[C@H]1C[C@@H](O[C@H]2[C@@H]1CCC(=C2)C)CC(C)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)NC(=O)C
• InChI: InChI=1S/C22H37NO7/c1-11-5-6-16-12(2)8-15(29-17(16)7-11)9-13(3)28-22-19(23-14(4)25)21(27)20(26)18(10-24)30-22/h7,12-13,15-22,24,26-27H,5-6,8-10H2,1-4H3,(H,23,25)/t12-,13?,15+,16+,17+,18+,19+,20+,21+,22-/m0/s1
• InChI Key: VRMQEAKUIZSPBV-OHYUYLOTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₇NO₇
• Molecular Weight: 427.50 g/mol
• Exact Mass: 427.25700252 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.88
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• N-[(2S,3R,4R,5S,6R)-2-[1-[(2R,4S,4aR,8aS)-4,7-dimethyl-3,4,4a,5,6,8a-hexahydro-2H-chromen-2-yl]propan-2-yloxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• N-((2S,3R,4R,5S,6R)-2-((1-((2R,4S,4ar,8as)-4,7-dimethyl-3,4,4a,5,6,8a-hexahydro-2H-1-benzopyran-2-yl)propan-2-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl)ethanimidate
• N-((2S,3R,4R,5S,6R)-2-(1-((2R,4S,4aR,8aS)-4,7-dimethyl-3,4,4a,5,6,8a-hexahydro-2H-chromen-2-yl)propan-2-yloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl)acetamide
• N-[(2S,3R,4R,5S,6R)-2-({1-[(2R,4S,4ar,8as)-4,7-dimethyl-3,4,4a,5,6,8a-hexahydro-2H-1-benzopyran-2-yl]propan-2-yl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidate
• RefChem:190968
• CHEBI:211031

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6488	64.88%
Caco-2	-	0.8219	82.19%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5968	59.68%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.7918	79.18%
OATP1B3 inhibitior	+	0.8995	89.95%
MATE1 inhibitior	-	0.9066	90.66%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7851	78.51%
P-glycoprotein inhibitior	-	0.6544	65.44%
P-glycoprotein substrate	-	0.5067	50.67%
CYP3A4 substrate	+	0.6644	66.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8709	87.09%
CYP3A4 inhibition	-	0.9145	91.45%
CYP2C9 inhibition	-	0.9112	91.12%
CYP2C19 inhibition	-	0.8955	89.55%
CYP2D6 inhibition	-	0.9325	93.25%
CYP1A2 inhibition	-	0.8696	86.96%
CYP2C8 inhibition	-	0.6150	61.50%
CYP inhibitory promiscuity	-	0.7999	79.99%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6388	63.88%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9689	96.89%
Skin irritation	-	0.7481	74.81%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.6448	64.48%
Human Ether-a-go-go-Related Gene inhibition	-	0.3762	37.62%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	-	0.5700	57.00%
skin sensitisation	-	0.8666	86.66%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8020	80.20%
Acute Oral Toxicity (c)	III	0.6746	67.46%
Estrogen receptor binding	+	0.6838	68.38%
Androgen receptor binding	-	0.5664	56.64%
Thyroid receptor binding	+	0.5861	58.61%
Glucocorticoid receptor binding	-	0.5336	53.36%
Aromatase binding	-	0.4855	48.55%
PPAR gamma	-	0.5323	53.23%
Honey bee toxicity	-	0.7740	77.40%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8833	88.33%

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	98.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.37%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.41%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	92.96%	83.82%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.95%	93.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.55%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.56%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.69%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.55%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.79%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.44%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.97%	96.21%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.89%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.63%	89.00%
CHEMBL5028	O14672	ADAM10	83.60%	97.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.59%	100.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.82%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.46%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	80.67%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.63%	91.24%

Plants that contains it

• Ceratostigma willmottianum
• Plumbago zeylanica

Cross-Links

• PubChem: 146683400
• LOTUS: LTS0087770
• wikiData: Q105252409