(5R,8S,11R,12S,15S,18S,19S,22R)-8-(1H-indol-3-ylmethyl)-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,12,19-tetramethyl-2-methylidene-3,6,9,13,16,20,25-heptaoxo-15-propan-2-yl-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid

Details

• Internal ID: f25f4776-ac27-4f37-8f8f-042529ab76fe
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: (5R,8S,11R,12S,15S,18S,19S,22R)-8-(1H-indol-3-ylmethyl)-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,12,19-tetramethyl-2-methylidene-3,6,9,13,16,20,25-heptaoxo-15-propan-2-yl-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
• SMILES (Canonical): CC1C(NC(=O)C(NC(=O)C(C(NC(=O)C(NC(=O)C(NC(=O)C(=C)N(C(=O)CCC(NC1=O)C(=O)O)C)C)CC2=CNC3=CC=CC=C32)C(=O)O)C)C(C)C)C=CC(=CC(C)C(CC4=CC=CC=C4)OC)C
• SMILES (Isomeric): C[C@H]1[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)C(=C)N(C(=O)CC[C@@H](NC1=O)C(=O)O)C)C)CC2=CNC3=CC=CC=C32)C(=O)O)C)C(C)C)/C=C/C(=C/[C@H](C)[C@H](CC4=CC=CC=C4)OC)/C
• InChI: InChI=1S/C53H70N8O12/c1-28(2)44-51(68)56-38(21-20-29(3)24-30(4)42(73-10)25-35-16-12-11-13-17-35)31(5)46(63)57-40(52(69)70)22-23-43(62)61(9)34(8)49(66)55-33(7)48(65)58-41(26-36-27-54-39-19-15-14-18-37(36)39)50(67)60-45(53(71)72)32(6)47(64)59-44/h11-21,24,27-28,30-33,38,40-42,44-45,54H,8,22-23,25-26H2,1-7,9-10H3,(H,55,66)(H,56,68)(H,57,63)(H,58,65)(H,59,64)(H,60,67)(H,69,70)(H,71,72)/b21-20+,29-24+/t30-,31-,32-,33+,38-,40+,41-,42-,44-,45+/m0/s1
• InChI Key: UFZRCMUIGPFEPT-CGEDUOAOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₇₀N₈O₁₂
• Molecular Weight: 1011.20 g/mol
• Exact Mass: 1010.51131970 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 10
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

• DTXSID101334657

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7343	73.43%
Caco-2	-	0.8653	86.53%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6230	62.30%
OATP2B1 inhibitior	-	0.7125	71.25%
OATP1B1 inhibitior	+	0.8289	82.89%
OATP1B3 inhibitior	+	0.9042	90.42%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8720	87.20%
BSEP inhibitior	+	0.9038	90.38%
P-glycoprotein inhibitior	+	0.7483	74.83%
P-glycoprotein substrate	+	0.8407	84.07%
CYP3A4 substrate	+	0.7500	75.00%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8674	86.74%
CYP3A4 inhibition	+	0.6237	62.37%
CYP2C9 inhibition	-	0.6575	65.75%
CYP2C19 inhibition	-	0.6419	64.19%
CYP2D6 inhibition	-	0.8751	87.51%
CYP1A2 inhibition	-	0.6827	68.27%
CYP2C8 inhibition	+	0.7535	75.35%
CYP inhibitory promiscuity	+	0.7566	75.66%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5449	54.49%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9016	90.16%
Skin irritation	-	0.7783	77.83%
Skin corrosion	-	0.9262	92.62%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7199	71.99%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.5014	50.14%
skin sensitisation	-	0.8644	86.44%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8833	88.33%
Acute Oral Toxicity (c)	III	0.5803	58.03%
Estrogen receptor binding	+	0.7713	77.13%
Androgen receptor binding	+	0.7211	72.11%
Thyroid receptor binding	+	0.6535	65.35%
Glucocorticoid receptor binding	+	0.6958	69.58%
Aromatase binding	+	0.6176	61.76%
PPAR gamma	+	0.7791	77.91%
Honey bee toxicity	-	0.6587	65.87%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9449	94.49%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.98%	83.82%
CHEMBL2581	P07339	Cathepsin D	99.78%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.70%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	98.68%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.64%	91.11%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	97.61%	91.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.39%	95.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	96.74%	90.08%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	96.23%	97.64%
CHEMBL3310	Q96DB2	Histone deacetylase 11	95.96%	88.56%
CHEMBL4072	P07858	Cathepsin B	95.78%	93.67%
CHEMBL1937	Q92769	Histone deacetylase 2	95.52%	94.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.70%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.59%	94.45%
CHEMBL3837	P07711	Cathepsin L	91.10%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.79%	95.89%
CHEMBL1949	P62937	Cyclophilin A	88.68%	98.57%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.53%	89.00%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	88.32%	92.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.43%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.72%	92.62%
CHEMBL4644	P41968	Melanocortin receptor 3	85.38%	99.52%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.77%	97.09%
CHEMBL255	P29275	Adenosine A2b receptor	83.50%	98.59%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.50%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.13%	99.17%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.93%	93.99%
CHEMBL2535	P11166	Glucose transporter	81.64%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.04%	95.50%
CHEMBL1255126	O15151	Protein Mdm4	80.42%	90.20%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 146684968
• LOTUS: LTS0126931
• wikiData: Q104246750