[D-Leu1]MC-RR

Details

• Internal ID: 402ecbe2-273f-4eb8-9f4d-1bfcc79a440f
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: (5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis[3-(diaminomethylideneamino)propyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,12,19-trimethyl-2-methylidene-5-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-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)CC(C)C)CCCN=C(N)N)C(=O)O)C)CCCN=C(N)N)C=CC(=CC(C)C(CC2=CC=CC=C2)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)CC(C)C)CCCN=C(N)N)C(=O)O)C)CCCN=C(N)N)/C=C/C(=C/[C@H](C)[C@H](CC2=CC=CC=C2)OC)/C
• InChI: InChI=1S/C52H81N13O12/c1-28(2)25-39-48(72)61-37(18-14-24-58-52(55)56)47(71)64-42(50(75)76)32(6)44(68)60-36(17-13-23-57-51(53)54)46(70)59-35(20-19-29(3)26-30(4)40(77-9)27-34-15-11-10-12-16-34)31(5)43(67)62-38(49(73)74)21-22-41(66)65(8)33(7)45(69)63-39/h10-12,15-16,19-20,26,28,30-32,35-40,42H,7,13-14,17-18,21-25,27H2,1-6,8-9H3,(H,59,70)(H,60,68)(H,61,72)(H,62,67)(H,63,69)(H,64,71)(H,73,74)(H,75,76)(H4,53,54,57)(H4,55,56,58)/b20-19+,29-26+/t30-,31-,32-,35-,36-,37-,38+,39+,40-,42+/m0/s1
• InChI Key: BMULUGRVOLWIKI-AHYMVQLDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₁N₁₃O₁₂
• Molecular Weight: 1080.30 g/mol
• Exact Mass: 1079.61276507 g/mol
• Topological Polar Surface Area (TPSA): 408.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): -0.35
• H-Bond Acceptor: 12
• H-Bond Donor: 12
• Rotatable Bonds: 19

Synonyms

• (D-Leu1)MC-RR
• (5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis[3-(diaminomethylideneamino)propyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,12,19-trimethyl-2-methylidene-5-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
• (5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(3-(diaminomethylideneamino)propyl)-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl)-1,12,19-trimethyl-2-methylidene-5-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid
• (5R,8S,11R,12S,15S,18S,19S,22R)-8,15-Bis(3-carbamimidamidopropyl)-3,6,9,13,16,20-hexahydroxy-18-((3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylidene-5-(2-methylpropyl)-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylate
• (5R,8S,11R,12S,15S,18S,19S,22R)-8,15-Bis(3-carbamimidamidopropyl)-3,6,9,13,16,20-hexahydroxy-18-[(3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,12,19-trimethyl-2-methylidene-5-(2-methylpropyl)-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylate
• RefChem:69936
• (5R,8S,11R,12S,15S,18S,19S,22R)-8,15-bis(3-guanidinopropyl)-5-isobutyl-18-((1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,12,19-trimethyl-2-methylene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid
• CHEBI:221140
• DTXSID701046729
• NS00114651

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5851	58.51%
Caco-2	-	0.8644	86.44%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5783	57.83%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.8308	83.08%
OATP1B3 inhibitior	+	0.9260	92.60%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8788	87.88%
P-glycoprotein inhibitior	+	0.7448	74.48%
P-glycoprotein substrate	+	0.8614	86.14%
CYP3A4 substrate	+	0.7330	73.30%
CYP2C9 substrate	+	0.5767	57.67%
CYP2D6 substrate	-	0.8663	86.63%
CYP3A4 inhibition	-	0.8089	80.89%
CYP2C9 inhibition	-	0.7123	71.23%
CYP2C19 inhibition	-	0.6896	68.96%
CYP2D6 inhibition	-	0.8918	89.18%
CYP1A2 inhibition	-	0.7616	76.16%
CYP2C8 inhibition	+	0.7490	74.90%
CYP inhibitory promiscuity	-	0.9458	94.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5938	59.38%
Eye corrosion	-	0.9819	98.19%
Eye irritation	-	0.8983	89.83%
Skin irritation	-	0.7574	75.74%
Skin corrosion	-	0.9168	91.68%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6904	69.04%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.5802	58.02%
skin sensitisation	-	0.8273	82.73%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.7838	78.38%
Acute Oral Toxicity (c)	I	0.7599	75.99%
Estrogen receptor binding	+	0.6920	69.20%
Androgen receptor binding	+	0.7445	74.45%
Thyroid receptor binding	+	0.6669	66.69%
Glucocorticoid receptor binding	+	0.6851	68.51%
Aromatase binding	+	0.6943	69.43%
PPAR gamma	+	0.7765	77.65%
Honey bee toxicity	-	0.6889	68.89%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8171	81.71%

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	99.99%	83.82%
CHEMBL2581	P07339	Cathepsin D	99.79%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.59%	96.09%
CHEMBL3837	P07711	Cathepsin L	97.51%	96.61%
CHEMBL4072	P07858	Cathepsin B	96.52%	93.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.31%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.44%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.28%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.86%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.96%	94.45%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	91.23%	97.64%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.66%	95.89%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.33%	91.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.19%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.15%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.40%	97.09%
CHEMBL1255126	O15151	Protein Mdm4	85.85%	90.20%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.43%	93.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.46%	96.47%
CHEMBL4644	P41968	Melanocortin receptor 3	83.11%	99.52%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.51%	100.00%
CHEMBL2535	P11166	Glucose transporter	81.06%	98.75%
CHEMBL1951	P21397	Monoamine oxidase A	80.99%	91.49%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 146684772
• LOTUS: LTS0226351
• wikiData: Q104246722