(R)-1-(N-(3-Hydroxy-1-oxododecyl)-L-serine)syringomycin A1

Details

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Internal ID a6511907-eb7a-4504-b1da-cb4c0b4d5a2d
Taxonomy Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
IUPAC Name 2-[(9Z)-18,21-bis(2-aminoethyl)-12-benzyl-3-(2-chloro-1-hydroxyethyl)-15-[3-(diaminomethylideneamino)propyl]-24-(hydroxymethyl)-27-(3-hydroxyundecanoylamino)-2,5,8,11,14,17,20,23,26-nonaoxo-9-propylidene-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-6-yl]-2-hydroxyacetic acid
SMILES (Canonical) CCCCCCCCC(CC(=O)NC1COC(=O)C(NC(=O)C(NC(=O)C(=CCC)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CO)CCN)CCN)CCCN=C(N)N)CC2=CC=CC=C2)C(C(=O)O)O)C(CCl)O)O
SMILES (Isomeric) CCCCCCCCC(CC(=O)NC1COC(=O)C(NC(=O)C(NC(=O)/C(=C/CC)/NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CO)CCN)CCN)CCCN=C(N)N)CC2=CC=CC=C2)C(C(=O)O)O)C(CCl)O)O
InChI InChI=1S/C53H85ClN14O17/c1-3-5-6-7-8-12-17-30(70)25-39(72)60-37-28-85-52(84)40(38(71)26-54)67-50(81)41(42(73)51(82)83)68-46(77)31(14-4-2)61-47(78)35(24-29-15-10-9-11-16-29)65-43(74)32(18-13-23-59-53(57)58)62-44(75)33(19-21-55)63-45(76)34(20-22-56)64-48(79)36(27-69)66-49(37)80/h9-11,14-16,30,32-38,40-42,69-71,73H,3-8,12-13,17-28,55-56H2,1-2H3,(H,60,72)(H,61,78)(H,62,75)(H,63,76)(H,64,79)(H,65,74)(H,66,80)(H,67,81)(H,68,77)(H,82,83)(H4,57,58,59)/b31-14-
InChI Key YMFYPHGOLKNWQN-AQLQTECXSA-N
Popularity 43 references in papers

Physical and Chemical Properties

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Molecular Formula C53H85ClN14O17
Molecular Weight 1225.80 g/mol
Exact Mass 1224.5905650 g/mol
Topological Polar Surface Area (TPSA) 523.00 Ų
XlogP -3.00
Atomic LogP (AlogP) -5.64
H-Bond Acceptor 19
H-Bond Donor 18
Rotatable Bonds 26

Synonyms

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124888-22-8
2-[(9Z)-18,21-bis(2-aminoethyl)-12-benzyl-3-(2-chloro-1-hydroxyethyl)-15-[3-(diaminomethylideneamino)propyl]-24-(hydroxymethyl)-27-(3-hydroxyundecanoylamino)-2,5,8,11,14,17,20,23,26-nonaoxo-9-propylidene-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-6-yl]-2-hydroxyacetic acid
Syringomycin A1, 1-(N-(3-hydroxy-1-oxododecyl)-L-serine)-, (R)-

2D Structure

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2D Structure of (R)-1-(N-(3-Hydroxy-1-oxododecyl)-L-serine)syringomycin A1

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7530 75.30%
Caco-2 - 0.8639 86.39%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.5706 57.06%
OATP2B1 inhibitior - 0.8595 85.95%
OATP1B1 inhibitior + 0.8287 82.87%
OATP1B3 inhibitior + 0.9329 93.29%
MATE1 inhibitior - 0.8200 82.00%
OCT2 inhibitior - 0.7250 72.50%
BSEP inhibitior + 0.9706 97.06%
P-glycoprotein inhibitior + 0.7427 74.27%
P-glycoprotein substrate + 0.8547 85.47%
CYP3A4 substrate + 0.7371 73.71%
CYP2C9 substrate - 0.8012 80.12%
CYP2D6 substrate - 0.8429 84.29%
CYP3A4 inhibition - 0.8041 80.41%
CYP2C9 inhibition - 0.8290 82.90%
CYP2C19 inhibition - 0.7865 78.65%
CYP2D6 inhibition - 0.8948 89.48%
CYP1A2 inhibition - 0.7999 79.99%
CYP2C8 inhibition + 0.7937 79.37%
CYP inhibitory promiscuity - 0.9708 97.08%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.7600 76.00%
Carcinogenicity (trinary) Non-required 0.5600 56.00%
Eye corrosion - 0.9824 98.24%
Eye irritation - 0.8971 89.71%
Skin irritation - 0.7547 75.47%
Skin corrosion - 0.9182 91.82%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6733 67.33%
Micronuclear + 0.7700 77.00%
Hepatotoxicity - 0.5875 58.75%
skin sensitisation - 0.8141 81.41%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity + 0.9194 91.94%
Acute Oral Toxicity (c) III 0.5944 59.44%
Estrogen receptor binding + 0.7097 70.97%
Androgen receptor binding + 0.7037 70.37%
Thyroid receptor binding + 0.5576 55.76%
Glucocorticoid receptor binding + 0.6467 64.67%
Aromatase binding + 0.6858 68.58%
PPAR gamma + 0.6856 68.56%
Honey bee toxicity - 0.7184 71.84%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.5911 59.11%
Fish aquatic toxicity + 0.8766 87.66%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 99.71% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.67% 91.11%
CHEMBL2581 P07339 Cathepsin D 98.92% 98.95%
CHEMBL4040 P28482 MAP kinase ERK2 98.73% 83.82%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.67% 96.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 96.68% 99.17%
CHEMBL230 P35354 Cyclooxygenase-2 94.97% 89.63%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 93.75% 92.88%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.13% 95.56%
CHEMBL2693 Q9UIQ6 Cystinyl aminopeptidase 92.89% 97.64%
CHEMBL3392948 Q9NP59 Solute carrier family 40 member 1 92.74% 95.00%
CHEMBL3892 Q99500 Sphingosine 1-phosphate receptor Edg-3 92.53% 97.29%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 92.00% 96.47%
CHEMBL218 P21554 Cannabinoid CB1 receptor 91.87% 96.61%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.66% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 88.98% 94.73%
CHEMBL2327 P21452 Neurokinin 2 receptor 88.87% 98.89%
CHEMBL299 P17252 Protein kinase C alpha 87.42% 98.03%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 87.25% 100.00%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 86.96% 94.80%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 86.55% 95.50%
CHEMBL4296 Q15858 Sodium channel protein type IX alpha subunit 85.11% 96.11%
CHEMBL4581 P52732 Kinesin-like protein 1 84.82% 93.18%
CHEMBL4769 O95749 Geranylgeranyl pyrophosphate synthetase 84.59% 92.08%
CHEMBL1255126 O15151 Protein Mdm4 84.39% 90.20%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 84.36% 90.71%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.28% 97.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.48% 86.33%
CHEMBL2492 P36544 Neuronal acetylcholine receptor protein alpha-7 subunit 83.42% 88.42%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 83.41% 96.90%
CHEMBL221 P23219 Cyclooxygenase-1 82.72% 90.17%
CHEMBL5103 Q969S8 Histone deacetylase 10 81.59% 90.08%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 81.52% 83.00%
CHEMBL226 P30542 Adenosine A1 receptor 81.31% 95.93%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 81.24% 82.69%

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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There are no matching plants.

Cross-Links

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PubChem 6436256
LOTUS LTS0210429
wikiData Q105350509