Veraguamide A

Details

• Internal ID: cd9dc82a-3bc4-4dc9-a0ba-c8c3eab2acd1
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (3S,6S,9S,12S,13R,16S,19S)-13-(5-bromopent-4-ynyl)-3-[(2S)-butan-2-yl]-7,12,17-trimethyl-6,9,16-tri(propan-2-yl)-4,14-dioxa-1,7,10,17-tetrazabicyclo[17.3.0]docosane-2,5,8,11,15,18-hexone
• SMILES (Canonical): CCC(C)C1C(=O)N2CCCC2C(=O)N(C(C(=O)OC(C(C(=O)NC(C(=O)N(C(C(=O)O1)C(C)C)C)C(C)C)C)CCCC#CBr)C(C)C)C
• SMILES (Isomeric): CC[C@H](C)[C@H]1C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)O[C@@H]([C@@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)O1)C(C)C)C)C(C)C)C)CCCC#CBr)C(C)C)C
• InChI: InChI=1S/C37H59BrN4O8/c1-12-24(8)31-35(46)42-20-16-17-26(42)33(44)40(10)29(22(4)5)36(47)49-27(18-14-13-15-19-38)25(9)32(43)39-28(21(2)3)34(45)41(11)30(23(6)7)37(48)50-31/h21-31H,12-14,16-18,20H2,1-11H3,(H,39,43)/t24-,25-,26-,27+,28-,29-,30-,31-/m0/s1
• InChI Key: WWYBIFCBAWCPFI-AVCHBABLSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₉BrN₄O₈
• Molecular Weight: 767.80 g/mol
• Exact Mass: 766.35163 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: 7.00
• Atomic LogP (AlogP): 4.13
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

• DTXSID601236359
• RefChem:193943
• DTXCID901667531
• (3S,6S,9S,12S,13R,16S,19S)-13-(5-bromopent-4-ynyl)-3-((2S)-butan-2-yl)-7,12,17-trimethyl-6,9,16-tri(propan-2-yl)-4,14-dioxa-1,7,10,17-tetrazabicyclo(17.3.0)docosane-2,5,8,11,15,18-hexone
• CHEMBL1783105
• SCHEMBL29885991
• CHEBI:67330
• Q27135787

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6614	66.14%
Caco-2	-	0.8095	80.95%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.6027	60.27%
OATP2B1 inhibitior	-	0.5722	57.22%
OATP1B1 inhibitior	+	0.8291	82.91%
OATP1B3 inhibitior	+	0.9221	92.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7405	74.05%
P-glycoprotein inhibitior	+	0.7526	75.26%
P-glycoprotein substrate	+	0.7804	78.04%
CYP3A4 substrate	+	0.6665	66.65%
CYP2C9 substrate	-	0.6031	60.31%
CYP2D6 substrate	-	0.8447	84.47%
CYP3A4 inhibition	-	0.8937	89.37%
CYP2C9 inhibition	-	0.8200	82.00%
CYP2C19 inhibition	-	0.7712	77.12%
CYP2D6 inhibition	-	0.9035	90.35%
CYP1A2 inhibition	-	0.8155	81.55%
CYP2C8 inhibition	+	0.4572	45.72%
CYP inhibitory promiscuity	-	0.9575	95.75%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7732	77.32%
Carcinogenicity (trinary)	Non-required	0.5772	57.72%
Eye corrosion	-	0.9839	98.39%
Eye irritation	-	0.9152	91.52%
Skin irritation	-	0.7875	78.75%
Skin corrosion	-	0.8978	89.78%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4599	45.99%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.8671	86.71%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.5533	55.33%
Acute Oral Toxicity (c)	III	0.6869	68.69%
Estrogen receptor binding	+	0.7617	76.17%
Androgen receptor binding	+	0.6726	67.26%
Thyroid receptor binding	+	0.5411	54.11%
Glucocorticoid receptor binding	+	0.7251	72.51%
Aromatase binding	+	0.6735	67.35%
PPAR gamma	+	0.6987	69.87%
Honey bee toxicity	-	0.7950	79.50%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.7630	76.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL333	P08253	Matrix metalloproteinase-2	99.13%	96.31%
CHEMBL2581	P07339	Cathepsin D	98.82%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.71%	96.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	97.30%	90.08%
CHEMBL4588	P22894	Matrix metalloproteinase 8	96.95%	94.66%
CHEMBL3837	P07711	Cathepsin L	96.90%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.81%	97.25%
CHEMBL5203	P33316	dUTP pyrophosphatase	96.34%	99.18%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.01%	95.56%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	93.50%	82.38%
CHEMBL1937	Q92769	Histone deacetylase 2	92.89%	94.75%
CHEMBL1978	P11511	Cytochrome P450 19A1	92.42%	91.76%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.90%	97.09%
CHEMBL321	P14780	Matrix metalloproteinase 9	90.09%	92.12%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.69%	90.71%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	89.47%	95.58%
CHEMBL255	P29275	Adenosine A2b receptor	89.23%	98.59%
CHEMBL228	P31645	Serotonin transporter	88.21%	95.51%
CHEMBL1902	P62942	FK506-binding protein 1A	88.16%	97.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.64%	95.89%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.35%	96.38%
CHEMBL2189110	Q15910	Histone-lysine N-methyltransferase EZH2	86.95%	97.50%
CHEMBL2443	P49862	Kallikrein 7	86.40%	94.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.84%	95.50%
CHEMBL202	P00374	Dihydrofolate reductase	85.09%	89.92%
CHEMBL1949	P62937	Cyclophilin A	84.62%	98.57%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.28%	93.03%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.84%	96.47%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.76%	100.00%
CHEMBL332	P03956	Matrix metalloproteinase-1	83.37%	94.50%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.87%	93.40%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.49%	85.14%
CHEMBL1871	P10275	Androgen Receptor	81.87%	96.43%
CHEMBL3310	Q96DB2	Histone deacetylase 11	81.78%	88.56%
CHEMBL3384	Q16512	Protein kinase N1	80.48%	80.71%

Plants that contains it

• Panax japonicus

Cross-Links

• PubChem: 53355336
• NPASS: NPC124549
• ChEMBL: CHEMBL1783105
• LOTUS: LTS0150178
• wikiData: Q27135787