Cyclothialidine D

Details

• Internal ID: 22038dcc-6887-4162-b3dd-c8e344b6ed75
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: 2-[[(5R,8S)-8-[[(2S,3R)-1-[(2S)-2-aminopropanoyl]-3-hydroxypyrrolidine-2-carbonyl]amino]-14,16-dihydroxy-7,11-dioxo-10-oxa-3-thia-6-azabicyclo[10.4.0]hexadeca-1(12),13,15-triene-5-carbonyl]amino]acetic acid
• SMILES (Canonical): CC(C(=O)N1CCC(C1C(=O)NC2COC(=O)C3=C(CSCC(NC2=O)C(=O)NCC(=O)O)C(=CC(=C3)O)O)O)N
• SMILES (Isomeric): C[C@@H](C(=O)N1CC[C@H]([C@H]1C(=O)N[C@H]2COC(=O)C3=C(CSC[C@H](NC2=O)C(=O)NCC(=O)O)C(=CC(=C3)O)O)O)N
• InChI: InChI=1S/C24H31N5O11S/c1-10(25)23(38)29-3-2-16(31)19(29)22(37)27-14-7-40-24(39)12-4-11(30)5-17(32)13(12)8-41-9-15(28-21(14)36)20(35)26-6-18(33)34/h4-5,10,14-16,19,30-32H,2-3,6-9,25H2,1H3,(H,26,35)(H,27,37)(H,28,36)(H,33,34)/t10-,14-,15-,16+,19-/m0/s1
• InChI Key: QGZCMTZWELAYOU-HCYVDOCESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₁N₅O₁₁S
• Molecular Weight: 597.60 g/mol
• Exact Mass: 597.17407800 g/mol
• Topological Polar Surface Area (TPSA): 283.00 Ų
• XlogP: -4.20
• Atomic LogP (AlogP): -3.02
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

• 2-[[(5R,8S)-8-[[(2S,3R)-1-[(2S)-2-aminopropanoyl]-3-hydroxypyrrolidine-2-carbonyl]amino]-14,16-dihydroxy-7,11-dioxo-10-oxa-3-thia-6-azabicyclo[10.4.0]hexadeca-1(12),13,15-triene-5-carbonyl]amino]acetic acid
• 2-(((5R,8S)-8-(((2S,3R)-1-((2S)-2-aminopropanoyl)-3-hydroxypyrrolidine-2-carbonyl)amino)-14,16-dihydroxy-7,11-dioxo-10-oxa-3-thia-6-azabicyclo(10.4.0)hexadeca-1(12),13,15-triene-5-carbonyl)amino)acetic acid
• RefChem:130011
• CHEBI:201034
• HY-N14131

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5944	59.44%
Caco-2	-	0.9049	90.49%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Lysosomes	0.3704	37.04%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.8512	85.12%
OATP1B3 inhibitior	+	0.9323	93.23%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7778	77.78%
P-glycoprotein inhibitior	+	0.6277	62.77%
P-glycoprotein substrate	+	0.7848	78.48%
CYP3A4 substrate	+	0.6865	68.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8355	83.55%
CYP3A4 inhibition	-	0.8988	89.88%
CYP2C9 inhibition	-	0.8583	85.83%
CYP2C19 inhibition	-	0.8004	80.04%
CYP2D6 inhibition	-	0.8390	83.90%
CYP1A2 inhibition	-	0.8476	84.76%
CYP2C8 inhibition	+	0.6344	63.44%
CYP inhibitory promiscuity	-	0.8737	87.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6280	62.80%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9373	93.73%
Skin irritation	-	0.7744	77.44%
Skin corrosion	-	0.9291	92.91%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4786	47.86%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.5664	56.64%
skin sensitisation	-	0.8615	86.15%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8578	85.78%
Acute Oral Toxicity (c)	III	0.5338	53.38%
Estrogen receptor binding	+	0.7181	71.81%
Androgen receptor binding	+	0.7121	71.21%
Thyroid receptor binding	-	0.4889	48.89%
Glucocorticoid receptor binding	+	0.6676	66.76%
Aromatase binding	+	0.5687	56.87%
PPAR gamma	+	0.6606	66.06%
Honey bee toxicity	-	0.8159	81.59%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	-	0.6087	60.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.75%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.44%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.74%	91.11%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	95.93%	95.58%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.80%	89.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.66%	93.40%
CHEMBL236	P41143	Delta opioid receptor	93.65%	99.35%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.52%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.85%	99.23%
CHEMBL4208	P20618	Proteasome component C5	92.46%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.70%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.83%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.82%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.30%	97.09%
CHEMBL220	P22303	Acetylcholinesterase	88.07%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.70%	90.71%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	87.24%	93.10%
CHEMBL340	P08684	Cytochrome P450 3A4	86.70%	91.19%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	86.53%	90.24%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.11%	96.47%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.45%	97.14%
CHEMBL2535	P11166	Glucose transporter	84.94%	98.75%
CHEMBL3384	Q16512	Protein kinase N1	84.59%	80.71%
CHEMBL213	P08588	Beta-1 adrenergic receptor	84.28%	95.56%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	84.18%	98.33%
CHEMBL221	P23219	Cyclooxygenase-1	84.17%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.03%	99.17%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	83.90%	95.00%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	83.30%	97.64%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.23%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.79%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.87%	96.21%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.75%	93.03%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10817333
• LOTUS: LTS0101755
• wikiData: Q77281014