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Verapatuline

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 291416d2-433c-4669-83bf-3ef8ed9b7e34
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Jerveratrum-type alkaloids
IUPAC Name methyl (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-11-oxospiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyridine]-4'-carboxylate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C29H41NO5/c1-15-12-22-25(30(14-15)27(33)34-5)17(3)29(35-22)11-9-20-21-7-6-18-13-19(31)8-10-28(18,4)24(21)26(32)23(20)16(29)2/h6,15,17,19-22,24-25,31H,7-14H2,1-5H3/t15-,17+,19-,20-,21-,22+,24+,25-,28-,29-/m0/s1
InChI Key BSYVNBXLPWSHPA-VFVYFEGOSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C29H41NO5
Molecular Weight 483.60 g/mol
Exact Mass 483.29847341 g/mol
Topological Polar Surface Area (TPSA) 76.10 Ų
XlogP 3.20
Atomic LogP (AlogP) 4.66
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 0

Synonyms

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212968-58-6
DTXSID30441285
methyl (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-11-oxospiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyridine]-4'-carboxylate
methyl (3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-11-oxospiro(1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo(a)fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro(3,2-b)pyridine)-4'-carboxylate
RefChem:193956
DTXCID30392107
(2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-1,2,3,3',3'a,4,5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-Octadecahydro-3-hydroxy-3',6',10,11b-tetramethyl-11-oxo-spiro[9H-benzo[a]fluorene-9,2'(4'H)-furo[3,2-b]pyridine]-4'-carboxylic Acid Methyl Ester;
Methyl (22S,23R)-3beta-hydroxy-11-oxo-17beta-17,23-epoxyveratraman-28-carboxylate

2D Structure

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2D Structure of Verapatuline

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9718 97.18%
Caco-2 - 0.5515 55.15%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.5755 57.55%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8726 87.26%
OATP1B3 inhibitior + 0.9398 93.98%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.9726 97.26%
P-glycoprotein inhibitior + 0.6886 68.86%
P-glycoprotein substrate + 0.6164 61.64%
CYP3A4 substrate + 0.7339 73.39%
CYP2C9 substrate - 0.7853 78.53%
CYP2D6 substrate - 0.8538 85.38%
CYP3A4 inhibition - 0.8875 88.75%
CYP2C9 inhibition - 0.8875 88.75%
CYP2C19 inhibition - 0.8634 86.34%
CYP2D6 inhibition - 0.9196 91.96%
CYP1A2 inhibition - 0.7934 79.34%
CYP2C8 inhibition + 0.6366 63.66%
CYP inhibitory promiscuity - 0.9475 94.75%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.4677 46.77%
Eye corrosion - 0.9852 98.52%
Eye irritation - 0.9380 93.80%
Skin irritation - 0.7574 75.74%
Skin corrosion - 0.9227 92.27%
Ames mutagenesis - 0.6628 66.28%
Human Ether-a-go-go-Related Gene inhibition + 0.7055 70.55%
Micronuclear + 0.7000 70.00%
Hepatotoxicity + 0.6855 68.55%
skin sensitisation - 0.8558 85.58%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.9750 97.50%
Nephrotoxicity + 0.7651 76.51%
Acute Oral Toxicity (c) III 0.5631 56.31%
Estrogen receptor binding + 0.8354 83.54%
Androgen receptor binding + 0.7485 74.85%
Thyroid receptor binding + 0.5256 52.56%
Glucocorticoid receptor binding + 0.8138 81.38%
Aromatase binding + 0.7145 71.45%
PPAR gamma + 0.5615 56.15%
Honey bee toxicity - 0.6086 60.86%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.6100 61.00%
Fish aquatic toxicity + 0.9466 94.66%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.08% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.93% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.92% 91.11%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 92.70% 89.05%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 91.02% 99.23%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.27% 97.09%
CHEMBL1871 P10275 Androgen Receptor 90.23% 96.43%
CHEMBL221 P23219 Cyclooxygenase-1 89.42% 90.17%
CHEMBL4072 P07858 Cathepsin B 89.36% 93.67%
CHEMBL2581 P07339 Cathepsin D 88.38% 98.95%
CHEMBL241 Q14432 Phosphodiesterase 3A 87.92% 92.94%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 86.77% 96.77%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.05% 95.56%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 85.78% 97.14%
CHEMBL5028 O14672 ADAM10 85.60% 97.50%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.43% 97.25%
CHEMBL340 P08684 Cytochrome P450 3A4 85.14% 91.19%
CHEMBL5255 O00206 Toll-like receptor 4 83.09% 92.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.00% 89.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 82.67% 90.71%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 82.64% 85.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.51% 100.00%
CHEMBL1907601 P11802 Cyclin-dependent kinase 4/cyclin D1 81.98% 98.99%
CHEMBL2094127 P06493 Cyclin-dependent kinase 1/cyclin B 81.94% 96.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.79% 95.89%
CHEMBL1859 O95180 Voltage-gated T-type calcium channel alpha-1H subunit 80.13% 98.57%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.00% 95.89%

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 10528844
LOTUS LTS0237933
wikiData Q82258000