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(1R,3S,5R,7R,9R,13R,15S,18S)-3-Methoxy-18-methyl-13-[(1E)-4-methylpent-1-enyl]-11-oxo-12,19,20-trioxatricyclo[13.3.1.15,9]icos-7-yl (2Z)-5-(2-{(1Z)-3-[(methoxycarbonyl)amino]prop-1-enyl}-1,3-oxazol-4-yl)pent-2-enoate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 7d7990db-1538-4f4c-99e2-9c2b60ab37bf
Taxonomy Phenylpropanoids and polyketides > Macrolides and analogues
IUPAC Name [(1R,3S,5R,7R,9R,13R,15S,18S)-3-methoxy-18-methyl-13-[(E)-4-methylpent-1-enyl]-11-oxo-12,19,20-trioxatricyclo[13.3.1.15,9]icosan-7-yl] (Z)-5-[2-[(Z)-3-(methoxycarbonylamino)prop-1-enyl]-1,3-oxazol-4-yl]pent-2-enoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C38H56N2O10/c1-25(2)10-8-12-28-18-29-16-15-26(3)34(48-29)22-30(44-4)19-31-20-32(21-33(47-31)23-37(42)49-28)50-36(41)14-7-6-11-27-24-46-35(40-27)13-9-17-39-38(43)45-5/h7-9,12-14,24-26,28-34H,6,10-11,15-23H2,1-5H3,(H,39,43)/b12-8+,13-9-,14-7-/t26-,28-,29-,30-,31+,32+,33+,34+/m0/s1
InChI Key ZZQYLRUTULGFDB-NLVTXAACSA-N
Popularity 9 references in papers

Physical and Chemical Properties

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Molecular Formula C38H56N2O10
Molecular Weight 700.90 g/mol
Exact Mass 700.39349599 g/mol
Topological Polar Surface Area (TPSA) 145.00 Ų
XlogP 6.00
Atomic LogP (AlogP) 6.28
H-Bond Acceptor 11
H-Bond Donor 1
Rotatable Bonds 12

Synonyms

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(+)-Leucascandrolide A
(-)-Leucascandrolide A
SCHEMBL3216332
CHEMBL1222318

2D Structure

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2D Structure of (1R,3S,5R,7R,9R,13R,15S,18S)-3-Methoxy-18-methyl-13-[(1E)-4-methylpent-1-enyl]-11-oxo-12,19,20-trioxatricyclo[13.3.1.15,9]icos-7-yl (2Z)-5-(2-{(1Z)-3-[(methoxycarbonyl)amino]prop-1-enyl}-1,3-oxazol-4-yl)pent-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9894 98.94%
Caco-2 - 0.8296 82.96%
Blood Brain Barrier + 0.7750 77.50%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.5423 54.23%
OATP2B1 inhibitior - 0.5656 56.56%
OATP1B1 inhibitior + 0.8212 82.12%
OATP1B3 inhibitior + 0.9251 92.51%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior + 0.9895 98.95%
P-glycoprotein inhibitior + 0.8002 80.02%
P-glycoprotein substrate + 0.7768 77.68%
CYP3A4 substrate + 0.7265 72.65%
CYP2C9 substrate - 0.7985 79.85%
CYP2D6 substrate - 0.8871 88.71%
CYP3A4 inhibition + 0.7959 79.59%
CYP2C9 inhibition - 0.9071 90.71%
CYP2C19 inhibition - 0.9026 90.26%
CYP2D6 inhibition - 0.9231 92.31%
CYP1A2 inhibition - 0.9046 90.46%
CYP2C8 inhibition + 0.7755 77.55%
CYP inhibitory promiscuity - 0.5764 57.64%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6040 60.40%
Eye corrosion - 0.9880 98.80%
Eye irritation - 0.9237 92.37%
Skin irritation - 0.7984 79.84%
Skin corrosion - 0.9346 93.46%
Ames mutagenesis - 0.5054 50.54%
Human Ether-a-go-go-Related Gene inhibition + 0.8532 85.32%
Micronuclear + 0.6200 62.00%
Hepatotoxicity + 0.6196 61.96%
skin sensitisation - 0.8707 87.07%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.4699 46.99%
Acute Oral Toxicity (c) III 0.6310 63.10%
Estrogen receptor binding + 0.8220 82.20%
Androgen receptor binding + 0.5856 58.56%
Thyroid receptor binding - 0.5160 51.60%
Glucocorticoid receptor binding + 0.7414 74.14%
Aromatase binding + 0.5273 52.73%
PPAR gamma + 0.7582 75.82%
Honey bee toxicity - 0.6612 66.12%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity + 0.9086 90.86%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 7.9 nM
 Potency
 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.90% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.34% 96.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 92.56% 99.17%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 90.85% 96.00%
CHEMBL3401 O75469 Pregnane X receptor 89.70% 94.73%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.19% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.28% 99.23%
CHEMBL2581 P07339 Cathepsin D 88.16% 98.95%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 87.87% 89.34%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 84.86% 96.77%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 84.81% 96.38%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 84.05% 95.71%
CHEMBL340 P08684 Cytochrome P450 3A4 83.30% 91.19%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.69% 92.62%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.91% 86.33%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.85% 94.33%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 80.57% 96.90%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.13% 97.09%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
There are no matching plants.

Cross-Links

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PubChem 10259181
LOTUS LTS0126966
wikiData Q105387001