cyclo[2Abz-D-xiIle-Tyr-Thr-Ala-Ile-Pro]

Details

• Internal ID: 35c1888f-b437-4738-b121-665271cee071
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Cyclic peptides
• IUPAC Name: (4S,10S,13S,16S,19S,22R)-22-butan-2-yl-10-[(2S)-butan-2-yl]-16-[(1R)-1-hydroxyethyl]-19-[(4-hydroxyphenyl)methyl]-13-methyl-2,8,11,14,17,20,23-heptazatricyclo[23.4.0.04,8]nonacosa-1(29),25,27-triene-3,9,12,15,18,21,24-heptone
• SMILES (Canonical): CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2CCCC2C(=O)NC3=CC=CC=C3C(=O)N1)C(C)CC)C)C(C)O)CC4=CC=C(C=C4)O
• SMILES (Isomeric): CC[C@H](C)[C@H]1C(=O)N2CCC[C@H]2C(=O)NC3=CC=CC=C3C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C)[C@@H](C)O)CC4=CC=C(C=C4)O)C(C)CC
• InChI: InChI=1S/C40H55N7O9/c1-7-21(3)31-38(54)43-29(20-25-15-17-26(49)18-16-25)36(52)46-33(24(6)48)39(55)41-23(5)34(50)45-32(22(4)8-2)40(56)47-19-11-14-30(47)37(53)42-28-13-10-9-12-27(28)35(51)44-31/h9-10,12-13,15-18,21-24,29-33,48-49H,7-8,11,14,19-20H2,1-6H3,(H,41,55)(H,42,53)(H,43,54)(H,44,51)(H,45,50)(H,46,52)/t21?,22-,23-,24+,29-,30-,31+,32-,33-/m0/s1
• InChI Key: MIMIVDMPUMTORB-PXJAYGQUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₅N₇O₉
• Molecular Weight: 777.90 g/mol
• Exact Mass: 777.40612636 g/mol
• Topological Polar Surface Area (TPSA): 235.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 1.11
• H-Bond Acceptor: 9
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• (4S,10S,13S,16S,19S,22R)-22-butan-2-yl-10-[(2S)-butan-2-yl]-16-[(1R)-1-hydroxyethyl]-19-[(4-hydroxyphenyl)methyl]-13-methyl-2,8,11,14,17,20,23-heptazatricyclo[23.4.0.04,8]nonacosa-1(29),25,27-triene-3,9,12,15,18,21,24-heptone
• (4S,10S,13S,16S,19S,22R)-22-butan-2-yl-10-((2S)-butan-2-yl)-16-((1R)-1-hydroxyethyl)-19-((4-hydroxyphenyl)methyl)-13-methyl-2,8,11,14,17,20,23-heptazatricyclo(23.4.0.04,8)nonacosa-1(29),25,27-triene-3,9,12,15,18,21,24-heptone
• (4S,10S,13S,16S,19S,22S)-10,22-bis((2S)-butan-2-yl)-16-((1R)-1-hydroxyethyl)-19-((4-hydroxyphenyl)methyl)-13-methyl-2,8,11,14,17,20,23-heptazatricyclo(23.4.0.04,8)nonacosa-1(29),25,27-triene-3,9,12,15,18,21,24-heptone
• (4S,10S,13S,16S,19S,22S)-10,22-bis[(2S)-butan-2-yl]-16-[(1R)-1-hydroxyethyl]-19-[(4-hydroxyphenyl)methyl]-13-methyl-2,8,11,14,17,20,23-heptazatricyclo[23.4.0.04,8]nonacosa-1(29),25,27-triene-3,9,12,15,18,21,24-heptone
• RefChem:187257
• CHEBI:224307

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7492	74.92%
Caco-2	-	0.8680	86.80%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7380	73.80%
OATP2B1 inhibitior	+	0.5622	56.22%
OATP1B1 inhibitior	+	0.8012	80.12%
OATP1B3 inhibitior	+	0.9249	92.49%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8816	88.16%
BSEP inhibitior	+	0.8643	86.43%
P-glycoprotein inhibitior	+	0.7473	74.73%
P-glycoprotein substrate	+	0.8532	85.32%
CYP3A4 substrate	+	0.7033	70.33%
CYP2C9 substrate	+	0.6039	60.39%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	-	0.8695	86.95%
CYP2C9 inhibition	-	0.8765	87.65%
CYP2C19 inhibition	-	0.8966	89.66%
CYP2D6 inhibition	-	0.8214	82.14%
CYP1A2 inhibition	-	0.9052	90.52%
CYP2C8 inhibition	+	0.6342	63.42%
CYP inhibitory promiscuity	-	0.8919	89.19%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6613	66.13%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9197	91.97%
Skin irritation	-	0.8102	81.02%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.6408	64.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.3896	38.96%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.6052	60.52%
skin sensitisation	-	0.9018	90.18%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6956	69.56%
Acute Oral Toxicity (c)	III	0.6858	68.58%
Estrogen receptor binding	+	0.8146	81.46%
Androgen receptor binding	+	0.7234	72.34%
Thyroid receptor binding	+	0.5806	58.06%
Glucocorticoid receptor binding	+	0.6506	65.06%
Aromatase binding	+	0.5805	58.05%
PPAR gamma	+	0.7657	76.57%
Honey bee toxicity	-	0.7813	78.13%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9572	95.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.91%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.89%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.66%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.86%	91.11%
CHEMBL5103	Q969S8	Histone deacetylase 10	96.55%	90.08%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.30%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	94.51%	94.75%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	94.43%	90.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.30%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.84%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.16%	97.09%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	92.14%	82.38%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	91.92%	97.64%
CHEMBL226	P30542	Adenosine A1 receptor	91.46%	95.93%
CHEMBL1902	P62942	FK506-binding protein 1A	91.13%	97.05%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.88%	93.03%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.60%	82.69%
CHEMBL301	P24941	Cyclin-dependent kinase 2	88.40%	91.23%
CHEMBL5203	P33316	dUTP pyrophosphatase	87.11%	99.18%
CHEMBL206	P03372	Estrogen receptor alpha	86.90%	97.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.55%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.54%	97.14%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.98%	92.88%
CHEMBL3524	P56524	Histone deacetylase 4	85.94%	92.97%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.17%	93.40%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	84.67%	92.67%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.17%	90.71%
CHEMBL221	P23219	Cyclooxygenase-1	84.09%	90.17%
CHEMBL2535	P11166	Glucose transporter	82.49%	98.75%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	82.00%	95.48%
CHEMBL4208	P20618	Proteasome component C5	81.89%	90.00%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	81.73%	96.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.26%	89.00%
CHEMBL4616	Q92847	Ghrelin receptor	80.54%	92.00%
CHEMBL333	P08253	Matrix metalloproteinase-2	80.52%	96.31%

Plants that contains it

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Cross-Links

• PubChem: 139586550
• LOTUS: LTS0035687
• wikiData: Q77508812