Ramoplanin A3

Details

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Internal ID da24c256-e5d4-43e1-814d-05d4fd7fe34e
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)-8-methylnona-2,4-dienoyl]amino]butanediamide
SMILES (Canonical) CC1C(=O)NC(C(=O)OC(C(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)N1)CC(C)C)C2=CC=C(C=C2)O)C(C)O)C3=CC=C(C=C3)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)CCCN)CC6=CC=CC=C6)C(C)O)C7=CC=C(C=C7)O)C8=CC=C(C=C8)O)C(C)O)CCCN)C9=CC=C(C=C9)O)NC(=O)C(CC(=O)N)NC(=O)C=CC=CCCC(C)C)C(=O)N)C1=CC(=C(C=C1)O)Cl
SMILES (Isomeric) C[C@@H]1C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N1)CC(C)C)C2=CC=C(C=C2)O)[C@@H](C)O)C3=CC=C(C=C3)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@@H]5[C@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)CCCN)CC6=CC=CC=C6)[C@H](C)O)C7=CC=C(C=C7)O)C8=CC=C(C=C8)O)[C@@H](C)O)CCCN)C9=CC=C(C=C9)O)NC(=O)[C@H](CC(=O)N)NC(=O)/C=C\C=C\CCC(C)C)C(=O)N)C1=CC(=C(C=C1)O)Cl
InChI InChI=1S/C120H156ClN21O40/c1-55(2)18-12-9-10-15-23-83(154)128-78(51-82(124)153)108(167)142-94-100(102(125)161)181-118(177)93(67-34-45-79(152)73(121)50-67)141-103(162)57(5)127-106(165)76(48-56(3)4)129-84(155)52-126-109(168)88(62-24-35-68(148)36-25-62)137-112(171)87(60(8)147)135-114(173)90(66-32-43-72(44-33-66)178-120-101(98(159)96(157)81(54-144)180-120)182-119-99(160)97(158)95(156)80(53-143)179-119)136-105(164)74(21-16-46-122)130-107(166)77(49-61-19-13-11-14-20-61)132-110(169)85(58(6)145)134-115(174)91(64-28-39-70(150)40-29-64)139-116(175)92(65-30-41-71(151)42-31-65)138-111(170)86(59(7)146)133-104(163)75(22-17-47-123)131-113(172)89(140-117(94)176)63-26-37-69(149)38-27-63/h9-11,13-15,19-20,23-45,50,55-60,74-78,80-81,85-101,119-120,143-152,156-160H,12,16-18,21-22,46-49,51-54,122-123H2,1-8H3,(H2,124,153)(H2,125,161)(H,126,168)(H,127,165)(H,128,154)(H,129,155)(H,130,166)(H,131,172)(H,132,169)(H,133,163)(H,134,174)(H,135,173)(H,136,164)(H,137,171)(H,138,170)(H,139,175)(H,140,176)(H,141,162)(H,142,167)/b10-9+,23-15-/t57-,58+,59-,60-,74-,75-,76+,77+,78+,80-,81-,85+,86-,87-,88+,89-,90+,91-,92+,93+,94+,95-,96-,97+,98+,99+,100+,101+,119-,120+/m1/s1
InChI Key CFIGZBIRUKWIED-ISYBQQJVSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C120H156ClN21O40
Molecular Weight 2568.10 g/mol
Exact Mass 2567.0540514 g/mol
Topological Polar Surface Area (TPSA) 1000.00 Ų
XlogP 0.50
Atomic LogP (AlogP) -6.96
H-Bond Acceptor 42
H-Bond Donor 36
Rotatable Bonds 36

Synonyms

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UH11FDQ454
81988-89-8
Ramoplanin A(sub 3)
UNII-UH11FDQ454
ANTIBIOTIC A-16686A3
RAMOPLANIN A 1, 1-(N2-((2Z,4E)-8-METHYL-1-OXO-2,4-NONADIEN-1-YL)-L-ASPARAGINE)-
Ramoplanin A 1 (peptide moiety), 1-(N(sup 2)-methyl-1-oxo-2,4-nonadienyl)-L-asparagine)-11-(L-2-(4-((2-O-alpha-D-mannopyranosyl-alpha-D-mannopyranosyl)oxy)phenyl)glycine)-, (Z,Z)-

2D Structure

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2D Structure of Ramoplanin A3

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7504 75.04%
Caco-2 - 0.8568 85.68%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.3761 37.61%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8069 80.69%
OATP1B3 inhibitior + 0.9303 93.03%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9311 93.11%
BSEP inhibitior + 0.9516 95.16%
P-glycoprotein inhibitior + 0.7417 74.17%
P-glycoprotein substrate + 0.8614 86.14%
CYP3A4 substrate + 0.7631 76.31%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8593 85.93%
CYP3A4 inhibition - 0.5356 53.56%
CYP2C9 inhibition - 0.8206 82.06%
CYP2C19 inhibition - 0.7601 76.01%
CYP2D6 inhibition - 0.8677 86.77%
CYP1A2 inhibition - 0.8874 88.74%
CYP2C8 inhibition + 0.8671 86.71%
CYP inhibitory promiscuity - 0.7964 79.64%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.7338 73.38%
Carcinogenicity (trinary) Non-required 0.5633 56.33%
Eye corrosion - 0.9850 98.50%
Eye irritation - 0.8952 89.52%
Skin irritation - 0.7631 76.31%
Skin corrosion - 0.9266 92.66%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7188 71.88%
Micronuclear + 0.8100 81.00%
Hepatotoxicity - 0.6945 69.45%
skin sensitisation - 0.8506 85.06%
Respiratory toxicity + 0.8111 81.11%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.9625 96.25%
Nephrotoxicity - 0.6556 65.56%
Acute Oral Toxicity (c) III 0.6413 64.13%
Estrogen receptor binding - 0.5771 57.71%
Androgen receptor binding + 0.7698 76.98%
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 - 0.5999 59.99%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5152 51.52%
Fish aquatic toxicity + 0.9382 93.82%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 99.98% 91.11%
CHEMBL2581 P07339 Cathepsin D 99.69% 98.95%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 99.53% 93.10%
CHEMBL226 P30542 Adenosine A1 receptor 98.74% 95.93%
CHEMBL3060 Q9Y345 Glycine transporter 2 98.26% 99.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.90% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 97.65% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 97.41% 94.73%
CHEMBL4296 Q15858 Sodium channel protein type IX alpha subunit 97.29% 96.11%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 97.03% 99.15%
CHEMBL221 P23219 Cyclooxygenase-1 96.79% 90.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.75% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.25% 95.56%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 94.80% 97.33%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 94.76% 96.47%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 94.66% 95.50%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 93.59% 97.14%
CHEMBL236 P41143 Delta opioid receptor 93.56% 99.35%
CHEMBL5608 Q16288 NT-3 growth factor receptor 93.36% 95.89%
CHEMBL3392948 Q9NP59 Solute carrier family 40 member 1 90.19% 95.00%
CHEMBL206 P03372 Estrogen receptor alpha 90.01% 97.64%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 89.91% 95.89%
CHEMBL4208 P20618 Proteasome component C5 89.47% 90.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 89.45% 96.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.39% 86.33%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 88.36% 85.00%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 88.02% 95.58%
CHEMBL2072 P35499 Sodium channel protein type IV alpha subunit 86.10% 92.32%
CHEMBL4227 P25090 Lipoxin A4 receptor 85.09% 100.00%
CHEMBL4581 P52732 Kinesin-like protein 1 84.95% 93.18%
CHEMBL3359 P21462 Formyl peptide receptor 1 84.57% 93.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.95% 85.14%
CHEMBL2693 Q9UIQ6 Cystinyl aminopeptidase 83.21% 97.64%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 82.99% 100.00%
CHEMBL2243 O00519 Anandamide amidohydrolase 82.58% 97.53%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 82.46% 95.71%
CHEMBL242 Q92731 Estrogen receptor beta 82.13% 98.35%
CHEMBL3837 P07711 Cathepsin L 81.66% 96.61%
CHEMBL340 P08684 Cytochrome P450 3A4 81.17% 91.19%
CHEMBL1949 P62937 Cyclophilin A 81.00% 98.57%
CHEMBL2514 O95665 Neurotensin receptor 2 80.44% 100.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 80.32% 93.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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Cross-Links

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PubChem 76963329
LOTUS LTS0029199
wikiData Q27291069