Maculansin A

Details

• Internal ID: ebfe7f12-6a5c-4953-982a-ff0ab8ee5f3a
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: [(2R,3S,4S,5R)-1,6-diacetyloxy-3,4-dihydroxy-5-(2-isocyano-3-methylbut-2-enoyl)oxyhexan-2-yl] 2-isocyano-3-methylbut-2-enoate
• SMILES (Canonical): CC(=C(C(=O)OC(COC(=O)C)C(C(C(COC(=O)C)OC(=O)C(=C(C)C)[N+]#[C-])O)O)[N+]#[C-])C
• SMILES (Isomeric): CC(=C(C(=O)O[C@H](COC(=O)C)[C@H]([C@@H]([C@@H](COC(=O)C)OC(=O)C(=C(C)C)[N+]#[C-])O)O)[N+]#[C-])C
• InChI: InChI=1S/C22H28N2O10/c1-11(2)17(23-7)21(29)33-15(9-31-13(5)25)19(27)20(28)16(10-32-14(6)26)34-22(30)18(24-8)12(3)4/h15-16,19-20,27-28H,9-10H2,1-6H3/t15-,16-,19-,20-/m1/s1
• InChI Key: XQBSOXRYXYNGRH-XNFNUYLZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈N₂O₁₀
• Molecular Weight: 480.50 g/mol
• Exact Mass: 480.17439509 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.08
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 11

Synonyms

• [(2R,3S,4S,5R)-1,6-diacetyloxy-3,4-dihydroxy-5-(2-isocyano-3-methylbut-2-enoyl)oxyhexan-2-yl] 2-isocyano-3-methylbut-2-enoate
• CHEBI:188585
• 1,6-Di-O-acetyl-2,5-bis-O-(2-isocyano-3-methyl-2-butenoyl)-D-mannitol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5900	59.00%
Caco-2	-	0.7363	73.63%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8234	82.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9362	93.62%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7388	73.88%
P-glycoprotein inhibitior	+	0.6772	67.72%
P-glycoprotein substrate	-	0.8596	85.96%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7948	79.48%
CYP2D6 substrate	-	0.8787	87.87%
CYP3A4 inhibition	-	0.7999	79.99%
CYP2C9 inhibition	-	0.7319	73.19%
CYP2C19 inhibition	-	0.7843	78.43%
CYP2D6 inhibition	-	0.8328	83.28%
CYP1A2 inhibition	-	0.7719	77.19%
CYP2C8 inhibition	-	0.9406	94.06%
CYP inhibitory promiscuity	-	0.8829	88.29%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7733	77.33%
Carcinogenicity (trinary)	Non-required	0.6225	62.25%
Eye corrosion	-	0.9639	96.39%
Eye irritation	-	0.8913	89.13%
Skin irritation	-	0.7446	74.46%
Skin corrosion	-	0.9265	92.65%
Ames mutagenesis	+	0.5193	51.93%
Human Ether-a-go-go-Related Gene inhibition	-	0.5381	53.81%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.6593	65.93%
skin sensitisation	-	0.8372	83.72%
Respiratory toxicity	-	0.7889	78.89%
Reproductive toxicity	-	0.6941	69.41%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.7551	75.51%
Acute Oral Toxicity (c)	III	0.5948	59.48%
Estrogen receptor binding	+	0.7689	76.89%
Androgen receptor binding	-	0.5780	57.80%
Thyroid receptor binding	+	0.6422	64.22%
Glucocorticoid receptor binding	+	0.6894	68.94%
Aromatase binding	+	0.5782	57.82%
PPAR gamma	+	0.6323	63.23%
Honey bee toxicity	-	0.8173	81.73%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.6867	68.67%

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	96.60%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.10%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.76%	85.14%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.57%	97.21%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.76%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.53%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.89%	94.45%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.60%	98.75%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 25180954
• LOTUS: LTS0184354
• wikiData: Q105339422