Abrusoside A

Details

• Internal ID: 513fc7a3-f8f7-4ea2-b237-80d53e8292fa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (1S,3R,6S,7S,8R,11S,12S,15R,16R)-7,12,16-trimethyl-15-[(1S)-1-[(2S)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylic acid
• SMILES (Canonical): CC1=CCC(OC1=O)C(C)C2CCC3(C2(CCC45C3CCC6C4(C5)CCC(C6(C)C(=O)O)OC7C(C(C(C(O7)CO)O)O)O)C)C
• SMILES (Isomeric): CC1=CC[C@H](OC1=O)[C@@H](C)[C@H]2CC[C@@]3([C@@]2(CC[C@]45[C@H]3CC[C@@H]6[C@]4(C5)CC[C@@H]([C@@]6(C)C(=O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)C
• InChI: InChI=1S/C36H54O10/c1-18-6-7-21(44-29(18)41)19(2)20-10-12-33(4)23-8-9-24-34(5,31(42)43)25(46-30-28(40)27(39)26(38)22(16-37)45-30)11-13-35(24)17-36(23,35)15-14-32(20,33)3/h6,19-28,30,37-40H,7-17H2,1-5H3,(H,42,43)/t19-,20+,21-,22+,23-,24-,25-,26+,27-,28+,30-,32+,33-,34-,35+,36-/m0/s1
• InChI Key: CJHYXUPCGHKJOO-AYOTXDKCSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₄O₁₀
• Molecular Weight: 646.80 g/mol
• Exact Mass: 646.37169792 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 3.57
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• CHEBI:2364
• (22S,24Z)-3beta-(beta-D-glucopyranosyloxy)-26-oxo-22,26-epoxy-9beta,19-cyclolanost-24-en-28-oic acid
• (1S,3R,6S,7S,8R,11S,12S,15R,16R)-7,12,16-trimethyl-15-[(1S)-1-[(2S)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylic acid
• 124962-06-7
• CHEMBL471718
• Abrusogenin 3-O-glucopyranoside
• CJHYXUPCGHKJOO-AYOTXDKCSA-N
• GLXC-25597
• LMST01100009
• Q27105641

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7489	74.89%
Caco-2	-	0.8665	86.65%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7996	79.96%
OATP2B1 inhibitior	-	0.5809	58.09%
OATP1B1 inhibitior	+	0.8150	81.50%
OATP1B3 inhibitior	+	0.8927	89.27%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6079	60.79%
BSEP inhibitior	+	0.5701	57.01%
P-glycoprotein inhibitior	+	0.7684	76.84%
P-glycoprotein substrate	-	0.6132	61.32%
CYP3A4 substrate	+	0.6958	69.58%
CYP2C9 substrate	-	0.8085	80.85%
CYP2D6 substrate	-	0.8924	89.24%
CYP3A4 inhibition	-	0.9105	91.05%
CYP2C9 inhibition	-	0.7745	77.45%
CYP2C19 inhibition	-	0.9090	90.90%
CYP2D6 inhibition	-	0.9494	94.94%
CYP1A2 inhibition	-	0.8417	84.17%
CYP2C8 inhibition	+	0.6160	61.60%
CYP inhibitory promiscuity	-	0.9122	91.22%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6937	69.37%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9255	92.55%
Skin irritation	-	0.5386	53.86%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7510	75.10%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7334	73.34%
skin sensitisation	-	0.9142	91.42%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.5750	57.50%
Acute Oral Toxicity (c)	I	0.4920	49.20%
Estrogen receptor binding	+	0.6945	69.45%
Androgen receptor binding	+	0.7454	74.54%
Thyroid receptor binding	-	0.6218	62.18%
Glucocorticoid receptor binding	+	0.6304	63.04%
Aromatase binding	+	0.6530	65.30%
PPAR gamma	+	0.6417	64.17%
Honey bee toxicity	-	0.7720	77.20%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9734	97.34%

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	97.88%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.77%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.27%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.97%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.65%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.06%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.50%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.37%	86.33%
CHEMBL220	P22303	Acetylcholinesterase	87.92%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	87.68%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.76%	94.45%
CHEMBL4208	P20618	Proteasome component C5	85.46%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.63%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.59%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.15%	97.09%
CHEMBL5028	O14672	ADAM10	83.45%	97.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.67%	93.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.65%	91.07%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.39%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.83%	97.14%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.35%	96.47%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.16%	96.21%

Plants that contains it

• Abrus fruticulosus
• Abrus melanospermus subsp. melanospermus
• Abrus precatorius

Cross-Links

• PubChem: 6857683
• NPASS: NPC10077
• LOTUS: LTS0183089
• wikiData: Q27105641