Deacetylvindoline

Details

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Internal ID cfa7babf-5f6d-48d5-9c11-faeafb215338
Taxonomy Alkaloids and derivatives > Plumeran-type alkaloids
IUPAC Name methyl (1R,9R,10S,11R,12R,19R)-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
SMILES (Canonical) CCC12C=CCN3C1C4(CC3)C(C(C2O)(C(=O)OC)O)N(C5=C4C=CC(=C5)OC)C
SMILES (Isomeric) CC[C@@]12C=CCN3[C@@H]1[C@]4(CC3)[C@H]([C@]([C@@H]2O)(C(=O)OC)O)N(C5=C4C=CC(=C5)OC)C
InChI InChI=1S/C23H30N2O5/c1-5-21-9-6-11-25-12-10-22(17(21)25)15-8-7-14(29-3)13-16(15)24(2)18(22)23(28,19(21)26)20(27)30-4/h6-9,13,17-19,26,28H,5,10-12H2,1-4H3/t17-,18+,19+,21+,22+,23-/m0/s1
InChI Key ZDKMPOJNYNVYLA-PEGGBQQISA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C23H30N2O5
Molecular Weight 414.50 g/mol
Exact Mass 414.21547206 g/mol
Topological Polar Surface Area (TPSA) 82.50 Ų
XlogP 2.30
Atomic LogP (AlogP) 1.07
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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Desacetyl Vindoline
4-Desacetylvindoline
3633-92-9
24ETH7DXT4
NSC-91993
UNII-24ETH7DXT4
Vindoline, deacetyl-
17-O-Deacetylvindoline
Desacetylvindoline
Aspidospermidine-3-carboxylic acid, 6,7-didehydro-3,4-dihydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)-
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Deacetylvindoline

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6095 60.95%
Caco-2 + 0.6191 61.91%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.7357 73.57%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9101 91.01%
OATP1B3 inhibitior + 0.9199 91.99%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior + 0.8040 80.40%
P-glycoprotein inhibitior + 0.7050 70.50%
P-glycoprotein substrate + 0.8755 87.55%
CYP3A4 substrate + 0.6929 69.29%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate + 0.3468 34.68%
CYP3A4 inhibition - 0.8966 89.66%
CYP2C9 inhibition - 0.8598 85.98%
CYP2C19 inhibition - 0.8298 82.98%
CYP2D6 inhibition - 0.5477 54.77%
CYP1A2 inhibition - 0.8975 89.75%
CYP2C8 inhibition - 0.8264 82.64%
CYP inhibitory promiscuity - 0.8189 81.89%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5430 54.30%
Eye corrosion - 0.9887 98.87%
Eye irritation - 0.9799 97.99%
Skin irritation - 0.7871 78.71%
Skin corrosion - 0.9427 94.27%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7086 70.86%
Micronuclear + 0.6800 68.00%
Hepatotoxicity - 0.5176 51.76%
skin sensitisation - 0.8555 85.55%
Respiratory toxicity + 0.9556 95.56%
Reproductive toxicity + 0.9778 97.78%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity - 0.8354 83.54%
Acute Oral Toxicity (c) III 0.6583 65.83%
Estrogen receptor binding + 0.7820 78.20%
Androgen receptor binding + 0.7550 75.50%
Thyroid receptor binding + 0.6321 63.21%
Glucocorticoid receptor binding + 0.6858 68.58%
Aromatase binding + 0.6351 63.51%
PPAR gamma + 0.6237 62.37%
Honey bee toxicity - 0.8368 83.68%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity - 0.6700 67.00%
Fish aquatic toxicity + 0.9457 94.57%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.49% 96.09%
CHEMBL4208 P20618 Proteasome component C5 97.38% 90.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.56% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.44% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.05% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.14% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.42% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.11% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 88.50% 90.17%
CHEMBL2581 P07339 Cathepsin D 88.48% 98.95%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.97% 94.00%
CHEMBL226 P30542 Adenosine A1 receptor 87.71% 95.93%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.54% 95.89%
CHEMBL205 P00918 Carbonic anhydrase II 85.73% 98.44%
CHEMBL3492 P49721 Proteasome Macropain subunit 85.09% 90.24%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.92% 92.62%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.37% 91.07%
CHEMBL4040 P28482 MAP kinase ERK2 81.95% 83.82%
CHEMBL3864 Q06124 Protein-tyrosine phosphatase 2C 81.13% 94.42%
CHEMBL5409 Q8TDU6 G-protein coupled bile acid receptor 1 80.75% 93.65%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.13% 96.00%

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.
Catharanthus roseus

Cross-Links

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PubChem 260534
LOTUS LTS0168323
wikiData Q19903931