Hibispeptin A

Details

• Internal ID: 41fe6b33-0dd8-450c-9e40-13e4c74c2840
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: (2S)-N-[(10S,13S,16S)-16-benzyl-3-ethyl-24-hydroxy-13-(2-methylpropyl)-5,11,14,17,20-pentaoxo-6,12,15,18-tetrazatricyclo[19.3.1.06,10]pentacosa-1(24),21(25),22-trien-4-yl]-5-oxopyrrolidine-2-carboxamide
• SMILES (Canonical): CCC1CC2=C(C=CC(=C2)C(=O)CNC(=O)C(NC(=O)C(NC(=O)C3CCCN3C(=O)C1NC(=O)C4CCC(=O)N4)CC(C)C)CC5=CC=CC=C5)O
• SMILES (Isomeric): CCC1CC2=C(C=CC(=C2)C(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]3CCCN3C(=O)C1NC(=O)[C@@H]4CCC(=O)N4)CC(C)C)CC5=CC=CC=C5)O
• InChI: InChI=1S/C39H50N6O8/c1-4-24-19-26-20-25(12-14-31(26)46)32(47)21-40-35(49)29(18-23-9-6-5-7-10-23)42-37(51)28(17-22(2)3)43-38(52)30-11-8-16-45(30)39(53)34(24)44-36(50)27-13-15-33(48)41-27/h5-7,9-10,12,14,20,22,24,27-30,34,46H,4,8,11,13,15-19,21H2,1-3H3,(H,40,49)(H,41,48)(H,42,51)(H,43,52)(H,44,50)/t24?,27-,28-,29-,30-,34?/m0/s1
• InChI Key: AJDZZZMMMKAKLQ-RPDZIHOMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₀N₆O₈
• Molecular Weight: 730.80 g/mol
• Exact Mass: 730.36901257 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 1.29
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• (2S)-N-[(10S,13S,16S)-16-Benzyl-3-ethyl-24-hydroxy-13-(2-methylpropyl)-5,11,14,17,20-pentaoxo-6,12,15,18-tetrazatricyclo[19.3.1.06,10]pentacosa-1(24),21(25),22-trien-4-yl]-5-oxopyrrolidine-2-carboxamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9397	93.97%
Caco-2	-	0.8912	89.12%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6304	63.04%
OATP2B1 inhibitior	+	0.5581	55.81%
OATP1B1 inhibitior	+	0.8453	84.53%
OATP1B3 inhibitior	+	0.9300	93.00%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7814	78.14%
BSEP inhibitior	+	0.9290	92.90%
P-glycoprotein inhibitior	+	0.7861	78.61%
P-glycoprotein substrate	+	0.8581	85.81%
CYP3A4 substrate	+	0.7031	70.31%
CYP2C9 substrate	+	0.5936	59.36%
CYP2D6 substrate	-	0.8317	83.17%
CYP3A4 inhibition	-	0.7887	78.87%
CYP2C9 inhibition	-	0.8405	84.05%
CYP2C19 inhibition	-	0.7215	72.15%
CYP2D6 inhibition	-	0.8181	81.81%
CYP1A2 inhibition	-	0.9788	97.88%
CYP2C8 inhibition	+	0.7529	75.29%
CYP inhibitory promiscuity	-	0.9198	91.98%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7800	78.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9293	92.93%
Skin irritation	-	0.7924	79.24%
Skin corrosion	-	0.9303	93.03%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4322	43.22%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.6803	68.03%
skin sensitisation	-	0.9000	90.00%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8358	83.58%
Acute Oral Toxicity (c)	III	0.6852	68.52%
Estrogen receptor binding	+	0.7976	79.76%
Androgen receptor binding	+	0.6491	64.91%
Thyroid receptor binding	+	0.5631	56.31%
Glucocorticoid receptor binding	+	0.6585	65.85%
Aromatase binding	+	0.5449	54.49%
PPAR gamma	+	0.7780	77.80%
Honey bee toxicity	-	0.7688	76.88%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9692	96.92%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.92%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.34%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.17%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.76%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.92%	83.82%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	96.46%	97.64%
CHEMBL3524	P56524	Histone deacetylase 4	94.84%	92.97%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	92.91%	97.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	92.54%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.90%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	91.41%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.33%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.74%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.99%	99.15%
CHEMBL236	P41143	Delta opioid receptor	88.91%	99.35%
CHEMBL333	P08253	Matrix metalloproteinase-2	88.25%	96.31%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.62%	94.45%
CHEMBL5203	P33316	dUTP pyrophosphatase	87.39%	99.18%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	86.24%	90.93%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.19%	93.99%
CHEMBL261	P00915	Carbonic anhydrase I	85.80%	96.76%
CHEMBL4208	P20618	Proteasome component C5	85.70%	90.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.62%	82.38%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.47%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.14%	99.23%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.59%	91.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.80%	99.17%
CHEMBL4531	P17931	Galectin-3	81.84%	96.90%
CHEMBL1937	Q92769	Histone deacetylase 2	81.41%	94.75%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.25%	91.03%
CHEMBL5028	O14672	ADAM10	80.87%	97.50%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.51%	96.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.47%	89.00%
CHEMBL205	P00918	Carbonic anhydrase II	80.42%	98.44%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	80.35%	91.79%

Plants that contains it

• Hibiscus syriacus

Cross-Links

• PubChem: 10818712
• LOTUS: LTS0133685
• wikiData: Q104913127