Ramoplanin A1

Details

• Internal ID: 8391039c-3e1e-42cb-a84e-d78a09e12c83
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides > Cyclic glycodepsipeptides
• IUPAC Name: (2S)-N-[(3S,6R,9S,15S,18R,21S,24R,27S,30S,33R,36S,39R,42R,45R,48S,49S)-24,42-bis(3-aminopropyl)-27-benzyl-49-carbamoyl-3-(3-chloro-4-hydroxyphenyl)-21-[4-[(2R,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyphenyl]-18,39-bis[(1R)-1-hydroxyethyl]-30-[(1S)-1-hydroxyethyl]-15,33,36,45-tetrakis(4-hydroxyphenyl)-6-methyl-9-(2-methylpropyl)-2,5,8,11,14,17,20,23,26,29,32,35,38,41,44,47-hexadecaoxo-1-oxa-4,7,10,13,16,19,22,25,28,31,34,37,40,43,46-pentadecazacyclononatetracont-48-yl]-2-[[(2Z,4E)-octa-2,4-dienoyl]amino]butanediamide
• SMILES (Canonical): CCCC=CC=CC(=O)NC(CC(=O)N)C(=O)NC1C(OC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)C2=CC=C(C=C2)O)CCCN)C(C)O)C3=CC=C(C=C3)O)C4=CC=C(C=C4)O)C(C)O)CC5=CC=CC=C5)CCCN)C6=CC=C(C=C6)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)CO)O)O)O)C(C)O)C9=CC=C(C=C9)O)CC(C)C)C)C1=CC(=C(C=C1)O)Cl)C(=O)N
• SMILES (Isomeric): CCC/C=C/C=C\C(=O)N[C@@H](CC(=O)N)C(=O)N[C@H]1[C@H](OC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC1=O)C2=CC=C(C=C2)O)CCCN)[C@@H](C)O)C3=CC=C(C=C3)O)C4=CC=C(C=C4)O)[C@H](C)O)CC5=CC=CC=C5)CCCN)C6=CC=C(C=C6)O[C@@H]7[C@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O[C@@H]8[C@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)[C@@H](C)O)C9=CC=C(C=C9)O)CC(C)C)C)C1=CC(=C(C=C1)O)Cl)C(=O)N
• InChI: InChI=1S/C118H152ClN21O40/c1-8-9-10-11-15-22-81(152)126-76(50-80(122)151)106(165)140-92-98(100(123)159)179-116(175)91(65-33-44-77(150)71(119)49-65)139-101(160)55(4)125-104(163)74(47-54(2)3)127-82(153)51-124-107(166)86(60-23-34-66(146)35-24-60)135-110(169)85(58(7)145)133-112(171)88(64-31-42-70(43-32-64)176-118-99(96(157)94(155)79(53-142)178-118)180-117-97(158)95(156)93(154)78(52-141)177-117)134-103(162)72(20-16-45-120)128-105(164)75(48-59-18-13-12-14-19-59)130-108(167)83(56(5)143)132-113(172)89(62-27-38-68(148)39-28-62)137-114(173)90(63-29-40-69(149)41-30-63)136-109(168)84(57(6)144)131-102(161)73(21-17-46-121)129-111(170)87(138-115(92)174)61-25-36-67(147)37-26-61/h10-15,18-19,22-44,49,54-58,72-76,78-79,83-99,117-118,141-150,154-158H,8-9,16-17,20-21,45-48,50-53,120-121H2,1-7H3,(H2,122,151)(H2,123,159)(H,124,166)(H,125,163)(H,126,152)(H,127,153)(H,128,164)(H,129,170)(H,130,167)(H,131,161)(H,132,172)(H,133,171)(H,134,162)(H,135,169)(H,136,168)(H,137,173)(H,138,174)(H,139,160)(H,140,165)/b11-10+,22-15-/t55-,56+,57-,58-,72-,73-,74+,75+,76+,78-,79-,83+,84-,85-,86+,87-,88+,89-,90+,91+,92+,93-,94-,95+,96+,97+,98+,99+,117-,118+/m1/s1
• InChI Key: QMJRFQRMRCJRIV-NIIZMFKTSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁₈H₁₅₂ClN₂₁O₄₀
• Molecular Weight: 2540.00 g/mol
• Exact Mass: 2539.0227512 g/mol
• Topological Polar Surface Area (TPSA): 1000.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -7.59
• H-Bond Acceptor: 42
• H-Bond Donor: 36
• Rotatable Bonds: 35

Synonyms

• V9PG4O8DRD
• 81988-87-6
• Ramoplanin A(sub 1)
• UNII-V9PG4O8DRD
• ANTIBIOTIC A-16686A1
• RAMOPLANIN A 1 (PEPTIDE MOIETY), 11-((2S)-2-(4-((2-O-.ALPHA.-D-MANNOPYRANOSYL-.ALPHA.-D-MANNOPYRANOSYL)OXY)PHENYL)GLYCINE)-
• RAMOPLANIN A 1 (PEPTIDE MOIETY), 11-(L-2-(4-((2-O-.ALPHA.-D-MANNOPYRANOSYL-.ALPHA.-D-MANNOPYRANOSYL)OXY)PHENYL)GLYCINE)-
• Ramoplanin A 1 (peptide moiety), 11-(L-2-(4-((2-O-alpha-D-mannopyranosyl-alpha-D-mannopyranosyl)oxy)phenyl)glycine)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7762	77.62%
Caco-2	-	0.8569	85.69%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4230	42.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8056	80.56%
OATP1B3 inhibitior	+	0.9298	92.98%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9311	93.11%
BSEP inhibitior	+	0.9531	95.31%
P-glycoprotein inhibitior	+	0.7417	74.17%
P-glycoprotein substrate	+	0.8610	86.10%
CYP3A4 substrate	+	0.7616	76.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8593	85.93%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.7936	79.36%
CYP2C19 inhibition	-	0.7079	70.79%
CYP2D6 inhibition	-	0.8689	86.89%
CYP1A2 inhibition	-	0.8451	84.51%
CYP2C8 inhibition	+	0.8703	87.03%
CYP inhibitory promiscuity	-	0.7947	79.47%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7138	71.38%
Carcinogenicity (trinary)	Non-required	0.5523	55.23%
Eye corrosion	-	0.9846	98.46%
Eye irritation	-	0.8952	89.52%
Skin irritation	-	0.7662	76.62%
Skin corrosion	-	0.9269	92.69%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7205	72.05%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.6820	68.20%
skin sensitisation	-	0.8502	85.02%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.6472	64.72%
Acute Oral Toxicity (c)	III	0.6423	64.23%
Estrogen receptor binding	-	0.5771	57.71%
Androgen receptor binding	+	0.7693	76.93%
Thyroid receptor binding	+	0.8229	82.29%
Glucocorticoid receptor binding	+	0.8565	85.65%
Aromatase binding	+	0.8256	82.56%
PPAR gamma	+	0.7883	78.83%
Honey bee toxicity	-	0.6020	60.20%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5352	53.52%
Fish aquatic toxicity	+	0.9225	92.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.97%	91.11%
CHEMBL2581	P07339	Cathepsin D	99.76%	98.95%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	99.40%	93.10%
CHEMBL226	P30542	Adenosine A1 receptor	98.49%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	98.34%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	98.27%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.84%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.78%	97.09%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	97.12%	96.11%
CHEMBL3401	O75469	Pregnane X receptor	96.76%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.55%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.54%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	94.49%	95.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	94.32%	96.47%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	94.09%	97.14%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	93.98%	97.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.32%	95.89%
CHEMBL236	P41143	Delta opioid receptor	93.19%	99.35%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.84%	99.15%
CHEMBL206	P03372	Estrogen receptor alpha	91.86%	97.64%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	91.74%	95.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.98%	86.33%
CHEMBL4208	P20618	Proteasome component C5	89.27%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.19%	96.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.19%	93.56%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	87.19%	92.32%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.54%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.48%	100.00%
CHEMBL242	Q92731	Estrogen receptor beta	86.06%	98.35%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	84.98%	97.64%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	84.76%	95.58%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.07%	91.71%
CHEMBL4530	P00488	Coagulation factor XIII	82.63%	96.00%
CHEMBL1949	P62937	Cyclophilin A	82.43%	98.57%
CHEMBL4581	P52732	Kinesin-like protein 1	81.60%	93.18%
CHEMBL340	P08684	Cytochrome P450 3A4	80.33%	91.19%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 76963330
• LOTUS: LTS0272245
• wikiData: Q27291704