Passicoccin

Details

• Internal ID: 2add9a15-e482-49fd-9dd7-dce13c79a93a
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Cyanogenic glycosides
• IUPAC Name: [4-cyano-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxycyclopent-2-en-1-yl] hydrogen sulfate
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3(CC(C=C3)OS(=O)(=O)O)C#N)O)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3(CC(C=C3)OS(=O)(=O)O)C#N)O)O)O)O)O)O
• InChI: InChI=1S/C18H27NO14S/c1-7-10(20)12(22)14(24)16(30-7)29-5-9-11(21)13(23)15(25)17(31-9)32-18(6-19)3-2-8(4-18)33-34(26,27)28/h2-3,7-17,20-25H,4-5H2,1H3,(H,26,27,28)/t7-,8?,9-,10-,11-,12+,13+,14+,15-,16-,17+,18?/m1/s1
• InChI Key: AFTIHDWVYIIJKS-GGJZXZOSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₇NO₁₄S
• Molecular Weight: 513.50 g/mol
• Exact Mass: 513.11522571 g/mol
• Topological Polar Surface Area (TPSA): 254.00 Ų
• XlogP: -4.30
• Atomic LogP (AlogP): -3.94
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• Passicoccin
• DTXSID30912541
• 4-Cyano-4-{[6-O-(6-deoxyhexopyranosyl)hexopyranosyl]oxy}cyclopent-2-en-1-yl hydrogen sulfate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7815	78.15%
Caco-2	-	0.8763	87.63%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4984	49.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9124	91.24%
OATP1B3 inhibitior	+	0.9384	93.84%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7455	74.55%
P-glycoprotein inhibitior	-	0.6421	64.21%
P-glycoprotein substrate	-	0.6686	66.86%
CYP3A4 substrate	+	0.6404	64.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8491	84.91%
CYP3A4 inhibition	-	0.8981	89.81%
CYP2C9 inhibition	-	0.7801	78.01%
CYP2C19 inhibition	-	0.7545	75.45%
CYP2D6 inhibition	-	0.8770	87.70%
CYP1A2 inhibition	-	0.7463	74.63%
CYP2C8 inhibition	-	0.6436	64.36%
CYP inhibitory promiscuity	-	0.8060	80.60%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.5868	58.68%
Carcinogenicity (trinary)	Non-required	0.5925	59.25%
Eye corrosion	-	0.9606	96.06%
Eye irritation	-	0.9530	95.30%
Skin irritation	-	0.7835	78.35%
Skin corrosion	-	0.8861	88.61%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7503	75.03%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.5634	56.34%
skin sensitisation	-	0.8205	82.05%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9227	92.27%
Acute Oral Toxicity (c)	III	0.5503	55.03%
Estrogen receptor binding	+	0.6187	61.87%
Androgen receptor binding	-	0.5584	55.84%
Thyroid receptor binding	-	0.5910	59.10%
Glucocorticoid receptor binding	+	0.5799	57.99%
Aromatase binding	+	0.5746	57.46%
PPAR gamma	+	0.5979	59.79%
Honey bee toxicity	-	0.6260	62.60%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.7518	75.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	96.27%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.15%	96.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	95.35%	95.83%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.78%	91.11%
CHEMBL1871	P10275	Androgen Receptor	91.94%	96.43%
CHEMBL2581	P07339	Cathepsin D	91.47%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.06%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	90.14%	90.17%
CHEMBL2179	P04062	Beta-glucocerebrosidase	89.62%	85.31%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.40%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.60%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.66%	96.61%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.96%	96.77%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.90%	94.80%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.19%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	83.75%	91.49%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.62%	96.38%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.30%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.25%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.24%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.76%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.84%	95.50%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.61%	82.38%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.16%	97.36%

Plants that contains it

• Passiflora coccinea

Cross-Links

• PubChem: 188631
• LOTUS: LTS0078750
• wikiData: Q82882839