Cyclotheonamide A

Details

• Internal ID: ab565160-3916-4542-b1e5-019cc51476ad
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Cyclic peptides
• IUPAC Name: N-[(3S,7E,9S,12R,16S,19S)-12-benzyl-16-[3-(diaminomethylideneamino)propyl]-9-[(4-hydroxyphenyl)methyl]-2,6,11,14,15,18-hexaoxo-1,5,10,13,17-pentazabicyclo[17.3.0]docos-7-en-3-yl]formamide
• SMILES (Canonical): C1CC2C(=O)NC(C(=O)C(=O)NC(C(=O)NC(C=CC(=O)NCC(C(=O)N2C1)NC=O)CC3=CC=C(C=C3)O)CC4=CC=CC=C4)CCCN=C(N)N
• SMILES (Isomeric): C1C[C@H]2C(=O)N[C@H](C(=O)C(=O)N[C@@H](C(=O)N[C@H](/C=C/C(=O)NC[C@@H](C(=O)N2C1)NC=O)CC3=CC=C(C=C3)O)CC4=CC=CC=C4)CCCN=C(N)N
• InChI: InChI=1S/C36H45N9O8/c37-36(38)39-16-4-8-26-31(49)34(52)44-27(19-22-6-2-1-3-7-22)32(50)42-24(18-23-10-13-25(47)14-11-23)12-15-30(48)40-20-28(41-21-46)35(53)45-17-5-9-29(45)33(51)43-26/h1-3,6-7,10-15,21,24,26-29,47H,4-5,8-9,16-20H2,(H,40,48)(H,41,46)(H,42,50)(H,43,51)(H,44,52)(H4,37,38,39)/b15-12+/t24-,26+,27-,28+,29+/m1/s1
• InChI Key: CDWXSPKJKIUEQF-BIXWYCRZSA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₅N₉O₈
• Molecular Weight: 731.80 g/mol
• Exact Mass: 731.33910943 g/mol
• Topological Polar Surface Area (TPSA): 268.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.95
• H-Bond Acceptor: 9
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

• UNII-2Y1TEH8EW7
• 2Y1TEH8EW7
• 129033-04-1
• CHEMBL342672
• 3-((4-Amino-5-(4-hydroxyphenyl)-1-oxo-2-pentenyl)amino)-N-formyl-L-alanyl-D-prolyl-6-((aminoiminomethyl)amino)-2-oxo-3-aminohexanoyl-L-phenylalanine cyclic (4-1)-peptide
• L-Phenylalanine, 3-((4-amino-5-(4-hydroxyphenyl)-1-oxo-2-pentenyl)amino)-N-formyl-L-alanyl-D-prolyl-6-((aminoiminomethyl)amino)-2-oxo-3-aminohexanoyl-, cyclic (4-1)-peptide
• CYCLOTHEONAMIDE A [MI]
• SCHEMBL1230642
• N-[14-Benzyl-18-(3-guanidino-propyl)-11-(4-hydroxy-benzyl)-4,8,13,16,17,20-hexaoxo-1,2,3,5,6,7,8,11,12,13,14,15,16,17,18,19,20,20a-octadecahydro-4H-3a,7,12,15,19-pentaaza-cyclopentacyclononadecen-5-yl]-formamide
• BDBM50118723
• DB04269
• MS-1144
• N-[(3S,7E,9S,12R,16S,19S)-12-benzyl-16-[3-(diaminomethylideneamino)propyl]-9-[(4-hydroxyphenyl)methyl]-2,6,11,14,15,18-hexaoxo-1,5,10,13,17-pentazabicyclo[17.3.0]docos-7-en-3-yl]formamide
• HY-120822
• CS-0079260
• Q27095088
• 1-{3-[(3S,7R,10S,11E,16S,21aS)-7-benzyl-16-(formylamino)-10-(4-hydroxybenzyl)-1,4,5,8,13,17-hexaoxo-2,3,4,5,6,7,8,9,10,13,14,15,16,17,19,20,21,21a-octadecahydro-1H-pyrrolo[2,1-j][1,4,8,11,15]pentaazacyclononadecin-3-yl]propyl}guanidine
• CYCLO((2S)-2-(FORMYLAMINO)-.BETA.-ALANYL-L-PROLYL-(3S)-3-AMINO-6-((AMINOIMINOMETHYL)AMINO)-2-OXOHEXANOYL-D-PHENYLALANYL-(2E,4S)-4-AMINO-5-(4-HYDROXYPHENYL)-2-PENTENOYL)
• N-((3S,7R,10S,16S,21aS,E)-7-benzyl-3-(3-guanidinopropyl)-10-(4-hydroxybenzyl)-1,4,5,8,13,17-hexaoxo-2,3,4,5,6,7,8,9,10,13,14,15,16,17,19,20,21,21a-octadecahydro-1H-pyrrolo[2,1-j][1,4,8,11,15]pentaazacyclononadecin-16-yl)formamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6530	65.30%
Caco-2	-	0.9006	90.06%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4888	48.88%
OATP2B1 inhibitior	+	0.5594	55.94%
OATP1B1 inhibitior	+	0.8178	81.78%
OATP1B3 inhibitior	+	0.9404	94.04%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9485	94.85%
P-glycoprotein inhibitior	+	0.7826	78.26%
P-glycoprotein substrate	+	0.8482	84.82%
CYP3A4 substrate	+	0.7077	70.77%
CYP2C9 substrate	-	0.8066	80.66%
CYP2D6 substrate	-	0.8391	83.91%
CYP3A4 inhibition	-	0.8783	87.83%
CYP2C9 inhibition	-	0.8628	86.28%
CYP2C19 inhibition	-	0.8617	86.17%
CYP2D6 inhibition	-	0.8768	87.68%
CYP1A2 inhibition	-	0.8906	89.06%
CYP2C8 inhibition	+	0.8001	80.01%
CYP inhibitory promiscuity	-	0.9683	96.83%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5962	59.62%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9264	92.64%
Skin irritation	-	0.7393	73.93%
Skin corrosion	-	0.9275	92.75%
Ames mutagenesis	-	0.5054	50.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5636	56.36%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	-	0.5227	52.27%
skin sensitisation	-	0.8371	83.71%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.4913	49.13%
Acute Oral Toxicity (c)	III	0.5989	59.89%
Estrogen receptor binding	+	0.7964	79.64%
Androgen receptor binding	+	0.7133	71.33%
Thyroid receptor binding	+	0.5791	57.91%
Glucocorticoid receptor binding	+	0.6302	63.02%
Aromatase binding	+	0.5262	52.62%
PPAR gamma	+	0.7263	72.63%
Honey bee toxicity	-	0.7848	78.48%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.8254	82.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL204	P00734	Thrombin	99.43%	96.01%
CHEMBL2581	P07339	Cathepsin D	99.22%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.75%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.12%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.79%	94.45%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	94.66%	97.64%
CHEMBL1902	P62942	FK506-binding protein 1A	94.29%	97.05%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.66%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.40%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.23%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	92.88%	93.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	92.87%	93.03%
CHEMBL1978	P11511	Cytochrome P450 19A1	88.90%	91.76%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.47%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.14%	97.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.22%	90.08%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.18%	99.17%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.45%	82.69%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.38%	90.93%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.87%	90.71%
CHEMBL217	P14416	Dopamine D2 receptor	83.67%	95.62%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	83.25%	83.14%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.97%	82.38%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.46%	90.95%
CHEMBL3524	P56524	Histone deacetylase 4	81.19%	92.97%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.42%	95.83%
CHEMBL2535	P11166	Glucose transporter	80.29%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.21%	95.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.17%	92.88%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5287991
• LOTUS: LTS0238508
• wikiData: Q27095088