cyclo[Gly-Val-Thr-Trp-Tyr-Pro-Ser-Ser]

Details

• Internal ID: 3245228e-7d09-4a91-8cd8-7d95ee2d03d8
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Cyclic peptides
• IUPAC Name: (3S,6S,9S,12S,18S,21S,24S)-9-[(1R)-1-hydroxyethyl]-18,21-bis(hydroxymethyl)-3-[(4-hydroxyphenyl)methyl]-6-(1H-indol-3-ylmethyl)-12-propan-2-yl-1,4,7,10,13,16,19,22-octazabicyclo[22.3.0]heptacosane-2,5,8,11,14,17,20,23-octone
• SMILES (Canonical): CC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)NC(C(=O)NCC(=O)N1)CO)CO)CC3=CC=C(C=C3)O)CC4=CNC5=CC=CC=C54)C(C)O
• SMILES (Isomeric): C[C@H]([C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N1)C(C)C)CO)CO)CC3=CC=C(C=C3)O)CC4=CNC5=CC=CC=C54)O
• InChI: InChI=1S/C42H55N9O12/c1-21(2)34-40(61)50-35(22(3)54)41(62)45-28(16-24-17-43-27-8-5-4-7-26(24)27)37(58)46-29(15-23-10-12-25(55)13-11-23)42(63)51-14-6-9-32(51)39(60)48-31(20-53)38(59)47-30(19-52)36(57)44-18-33(56)49-34/h4-5,7-8,10-13,17,21-22,28-32,34-35,43,52-55H,6,9,14-16,18-20H2,1-3H3,(H,44,57)(H,45,62)(H,46,58)(H,47,59)(H,48,60)(H,49,56)(H,50,61)/t22-,28+,29+,30+,31+,32+,34+,35+/m1/s1
• InChI Key: VSHYTYFXNJETAG-LBAHRTOPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₅₅N₉O₁₂
• Molecular Weight: 877.90 g/mol
• Exact Mass: 877.39701822 g/mol
• Topological Polar Surface Area (TPSA): 321.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -3.29
• H-Bond Acceptor: 12
• H-Bond Donor: 12
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9319	93.19%
Caco-2	-	0.8846	88.46%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7180	71.80%
OATP2B1 inhibitior	-	0.5760	57.60%
OATP1B1 inhibitior	+	0.8448	84.48%
OATP1B3 inhibitior	+	0.9283	92.83%
MATE1 inhibitior	-	0.8835	88.35%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9653	96.53%
P-glycoprotein inhibitior	+	0.7515	75.15%
P-glycoprotein substrate	+	0.8533	85.33%
CYP3A4 substrate	+	0.7237	72.37%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	-	0.7859	78.59%
CYP3A4 inhibition	-	0.6969	69.69%
CYP2C9 inhibition	-	0.8717	87.17%
CYP2C19 inhibition	-	0.8480	84.80%
CYP2D6 inhibition	-	0.9051	90.51%
CYP1A2 inhibition	-	0.9265	92.65%
CYP2C8 inhibition	+	0.6261	62.61%
CYP inhibitory promiscuity	-	0.6625	66.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6288	62.88%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9136	91.36%
Skin irritation	-	0.8027	80.27%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.6308	63.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.3976	39.76%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	-	0.6307	63.07%
skin sensitisation	-	0.9062	90.62%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.6689	66.89%
Acute Oral Toxicity (c)	III	0.6316	63.16%
Estrogen receptor binding	+	0.8025	80.25%
Androgen receptor binding	+	0.5204	52.04%
Thyroid receptor binding	+	0.5835	58.35%
Glucocorticoid receptor binding	-	0.4669	46.69%
Aromatase binding	+	0.5838	58.38%
PPAR gamma	+	0.7643	76.43%
Honey bee toxicity	-	0.7454	74.54%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.3722	37.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.81%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.49%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.02%	85.14%
CHEMBL5103	Q969S8	Histone deacetylase 10	98.83%	90.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.39%	96.09%
CHEMBL3524	P56524	Histone deacetylase 4	98.20%	92.97%
CHEMBL3310	Q96DB2	Histone deacetylase 11	97.69%	88.56%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	97.55%	96.69%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	96.28%	97.64%
CHEMBL5896	O75164	Lysine-specific demethylase 4A	95.80%	99.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.33%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.93%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.22%	94.45%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	94.20%	90.93%
CHEMBL333	P08253	Matrix metalloproteinase-2	94.05%	96.31%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.96%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.61%	97.09%
CHEMBL5203	P33316	dUTP pyrophosphatase	91.55%	99.18%
CHEMBL4040	P28482	MAP kinase ERK2	90.39%	83.82%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	90.33%	96.39%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	89.60%	82.38%
CHEMBL1937	Q92769	Histone deacetylase 2	89.48%	94.75%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.27%	91.71%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	86.87%	92.67%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.56%	95.83%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	86.52%	83.10%
CHEMBL1902	P62942	FK506-binding protein 1A	86.26%	97.05%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.90%	92.62%
CHEMBL2535	P11166	Glucose transporter	85.65%	98.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.89%	97.25%
CHEMBL255	P29275	Adenosine A2b receptor	84.29%	98.59%
CHEMBL321	P14780	Matrix metalloproteinase 9	84.27%	92.12%
CHEMBL4071	P08311	Cathepsin G	83.84%	94.64%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	83.76%	90.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.34%	97.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.45%	93.99%
CHEMBL1951	P21397	Monoamine oxidase A	82.45%	91.49%
CHEMBL213	P08588	Beta-1 adrenergic receptor	82.02%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	81.84%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.92%	94.00%
CHEMBL2189110	Q15910	Histone-lysine N-methyltransferase EZH2	80.25%	97.50%

Plants that contains it

• Stellaria yunnanensis

Cross-Links

• PubChem: 11400297
• LOTUS: LTS0164912
• wikiData: Q105292218