(-)-Caprazamycin A

Details

• Internal ID: 48702560-1076-4195-a028-e64554aaf49d
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Dipeptides
• IUPAC Name: (2S,5S,6S)-2-[[(2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxyoxolan-2-yl]oxy-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-1,4-dimethyl-6-[(3S)-3-[(3S)-3-methyl-5-oxo-5-[(2S,3R,4R,5R,6R)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxypentanoyl]oxyhexadecanoyl]oxy-3-oxo-1,4-diazepane-5-carboxylic acid
• SMILES (Canonical): CCCCCCCCCCCCCC(CC(=O)OC1CN(C(C(=O)N(C1C(=O)O)C)C(C2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)OC4C(C(C(O4)CN)O)O)C)OC(=O)CC(C)CC(=O)OC5C(C(C(C(O5)C)OC)OC)OC
• SMILES (Isomeric): CCCCCCCCCCCCC[C@@H](CC(=O)O[C@H]1CN([C@H](C(=O)N([C@@H]1C(=O)O)C)C([C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)O[C@H]4[C@@H]([C@@H]([C@H](O4)CN)O)O)C)OC(=O)C[C@H](C)CC(=O)O[C@H]5[C@@H]([C@@H]([C@@H]([C@H](O5)C)OC)OC)OC
• InChI: InChI=1S/C53H87N5O22/c1-9-10-11-12-13-14-15-16-17-18-19-20-30(75-34(60)23-28(2)24-35(61)78-52-47(73-8)46(72-7)43(71-6)29(3)74-52)25-36(62)76-32-27-56(4)38(48(67)57(5)37(32)50(68)69)44(80-51-42(66)39(63)31(26-54)77-51)45-40(64)41(65)49(79-45)58-22-21-33(59)55-53(58)70/h21-22,28-32,37-47,49,51-52,63-66H,9-20,23-27,54H2,1-8H3,(H,68,69)(H,55,59,70)/t28-,29+,30-,31+,32-,37-,38-,39+,40-,41+,42+,43+,44?,45-,46+,47+,49+,51-,52-/m0/s1
• InChI Key: JOXMICZHYUYJJD-AYLMBEEOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₇N₅O₂₂
• Molecular Weight: 1146.30 g/mol
• Exact Mass: 1145.58426942 g/mol
• Topological Polar Surface Area (TPSA): 361.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.16
• H-Bond Acceptor: 24
• H-Bond Donor: 7
• Rotatable Bonds: 31

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4811	48.11%
Caco-2	-	0.8596	85.96%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Lysosomes	0.4071	40.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8275	82.75%
OATP1B3 inhibitior	+	0.9276	92.76%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9595	95.95%
P-glycoprotein inhibitior	+	0.7443	74.43%
P-glycoprotein substrate	+	0.8126	81.26%
CYP3A4 substrate	+	0.7353	73.53%
CYP2C9 substrate	-	0.8011	80.11%
CYP2D6 substrate	-	0.8551	85.51%
CYP3A4 inhibition	+	0.5981	59.81%
CYP2C9 inhibition	-	0.7747	77.47%
CYP2C19 inhibition	-	0.8240	82.40%
CYP2D6 inhibition	-	0.8382	83.82%
CYP1A2 inhibition	-	0.8910	89.10%
CYP2C8 inhibition	+	0.7269	72.69%
CYP inhibitory promiscuity	-	0.8349	83.49%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6140	61.40%
Eye corrosion	-	0.9849	98.49%
Eye irritation	-	0.8982	89.82%
Skin irritation	-	0.7825	78.25%
Skin corrosion	-	0.9323	93.23%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7084	70.84%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.5052	50.52%
skin sensitisation	-	0.8692	86.92%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8196	81.96%
Acute Oral Toxicity (c)	III	0.6084	60.84%
Estrogen receptor binding	+	0.7855	78.55%
Androgen receptor binding	+	0.7389	73.89%
Thyroid receptor binding	+	0.6508	65.08%
Glucocorticoid receptor binding	+	0.7818	78.18%
Aromatase binding	+	0.6447	64.47%
PPAR gamma	+	0.8216	82.16%
Honey bee toxicity	-	0.6915	69.15%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5116	51.16%
Fish aquatic toxicity	+	0.8163	81.63%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.70%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.56%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	96.68%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.10%	97.25%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	94.48%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	93.23%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.02%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.01%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.90%	94.45%
CHEMBL5255	O00206	Toll-like receptor 4	91.84%	92.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.47%	86.33%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	90.21%	92.86%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.95%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.68%	93.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.72%	96.47%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.81%	100.00%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	86.35%	95.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.99%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.67%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.14%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.91%	97.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.35%	97.21%
CHEMBL255	P29275	Adenosine A2b receptor	83.34%	98.59%
CHEMBL1937	Q92769	Histone deacetylase 2	83.28%	94.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.88%	85.14%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	81.82%	83.00%
CHEMBL2885	P07451	Carbonic anhydrase III	81.58%	87.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.50%	96.00%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	81.41%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	80.49%	94.73%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139586657
• LOTUS: LTS0253966
• wikiData: Q77511421