Kirilowin A

Details

• Internal ID: c071d1ba-2512-4572-94a7-7fa969e4dfa4
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: [(2R,3R,4S,5R,6S)-6-hydroxy-3,4-bis(3-nitropropanoyloxy)-5-prop-2-enoyloxyoxan-2-yl]methyl 3-nitropropanoate
• SMILES (Canonical): C=CC(=O)OC1C(C(C(OC1O)COC(=O)CC[N+](=O)[O-])OC(=O)CC[N+](=O)[O-])OC(=O)CC[N+](=O)[O-]
• SMILES (Isomeric): C=CC(=O)O[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O)COC(=O)CC[N+](=O)[O-])OC(=O)CC[N+](=O)[O-])OC(=O)CC[N+](=O)[O-]
• InChI: InChI=1S/C18H23N3O16/c1-2-11(22)35-17-16(37-14(25)5-8-21(31)32)15(36-13(24)4-7-20(29)30)10(34-18(17)26)9-33-12(23)3-6-19(27)28/h2,10,15-18,26H,1,3-9H2/t10-,15-,16+,17-,18+/m1/s1
• InChI Key: IUZMPVCSOLDVAB-XJWTZCLFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₃N₃O₁₆
• Molecular Weight: 537.40 g/mol
• Exact Mass: 537.10783165 g/mol
• Topological Polar Surface Area (TPSA): 272.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.83
• H-Bond Acceptor: 16
• H-Bond Donor: 1
• Rotatable Bonds: 15

Synonyms

• [(2R,3R,4S,5R,6S)-6-hydroxy-3,4-bis(3-nitropropanoyloxy)-5-prop-2-enoyloxyoxan-2-yl]methyl 3-nitropropanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5575	55.75%
Caco-2	-	0.8732	87.32%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7405	74.05%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9269	92.69%
OATP1B3 inhibitior	+	0.9457	94.57%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7214	72.14%
P-glycoprotein inhibitior	+	0.6113	61.13%
P-glycoprotein substrate	-	0.9093	90.93%
CYP3A4 substrate	+	0.6140	61.40%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.8723	87.23%
CYP3A4 inhibition	-	0.8621	86.21%
CYP2C9 inhibition	-	0.7374	73.74%
CYP2C19 inhibition	-	0.6788	67.88%
CYP2D6 inhibition	-	0.8230	82.30%
CYP1A2 inhibition	-	0.7207	72.07%
CYP2C8 inhibition	-	0.7040	70.40%
CYP inhibitory promiscuity	-	0.8813	88.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8000	80.00%
Carcinogenicity (trinary)	Non-required	0.5398	53.98%
Eye corrosion	-	0.9759	97.59%
Eye irritation	-	0.9285	92.85%
Skin irritation	-	0.7223	72.23%
Skin corrosion	-	0.9044	90.44%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6584	65.84%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8286	82.86%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6289	62.89%
Acute Oral Toxicity (c)	III	0.6663	66.63%
Estrogen receptor binding	+	0.7801	78.01%
Androgen receptor binding	-	0.7202	72.02%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6409	64.09%
Aromatase binding	+	0.5713	57.13%
PPAR gamma	+	0.6428	64.28%
Honey bee toxicity	-	0.6380	63.80%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.7499	74.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.57%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.60%	99.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.17%	91.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.57%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.48%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.37%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	84.74%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.58%	96.95%
CHEMBL5255	O00206	Toll-like receptor 4	82.84%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.36%	94.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.28%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.87%	94.80%
CHEMBL4246	P42680	Tyrosine-protein kinase TEC	80.36%	82.05%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.16%	91.07%

Plants that contains it

• Indigofera kirilowii

Cross-Links

• PubChem: 11504779
• LOTUS: LTS0148839
• wikiData: Q105120938