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Rauvanin

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 f83ee156-de6a-472c-b6e8-06fb346ff8cf
Taxonomy Alkaloids and derivatives > Yohimbine alkaloids
IUPAC Name methyl (1S,15R,16R,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
SMILES (Canonical) CC1C2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=CC(=C(C=C45)OC)OC
SMILES (Isomeric) C[C@@H]1[C@H]2CN3CCC4=C([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)NC5=CC(=C(C=C45)OC)OC
InChI InChI=1S/C23H28N2O5/c1-12-16-10-25-6-5-13-15-8-20(27-2)21(28-3)9-18(15)24-22(13)19(25)7-14(16)17(11-30-12)23(26)29-4/h8-9,11-12,14,16,19,24H,5-7,10H2,1-4H3/t12-,14+,16-,19+/m1/s1
InChI Key FGWJRZQNNZVCHR-FERZIJSQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H28N2O5
Molecular Weight 412.50 g/mol
Exact Mass 412.19982200 g/mol
Topological Polar Surface Area (TPSA) 73.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 3.20
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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Rauvanine
3148-42-3
10,11-Dimethoxy-19-methyl-16,17-didehydrooxayohimban-16-carboxylic acid methyl ester
Dimethoxy-10,11 carbomethoxy-16 hetero yohimbane-3-alpha,15-alpha,19-alpha,20-beta [French]
Oxayohimban-16-carboxylic acid, 16,17-didehydro-10,11-dimethoxy-19-methyl-, methyl ester
Dimethoxy-10,11 carbomethoxy-16 hetero yohimbane-3-alpha,15-alpha,19-alpha,20-beta
methyl (1S,15R,16R,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
Methyl (1S,15R,20S)-6,7-dimethoxy-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
SCHEMBL17088377
AKOS040753709
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Rauvanin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9675 96.75%
Caco-2 + 0.7767 77.67%
Blood Brain Barrier + 0.8750 87.50%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.4556 45.56%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8431 84.31%
OATP1B3 inhibitior + 0.8214 82.14%
MATE1 inhibitior - 0.8037 80.37%
OCT2 inhibitior - 0.5639 56.39%
BSEP inhibitior + 0.8997 89.97%
P-glycoprotein inhibitior + 0.6926 69.26%
P-glycoprotein substrate + 0.7398 73.98%
CYP3A4 substrate + 0.6840 68.40%
CYP2C9 substrate - 0.8004 80.04%
CYP2D6 substrate + 0.3485 34.85%
CYP3A4 inhibition - 0.6885 68.85%
CYP2C9 inhibition - 0.6960 69.60%
CYP2C19 inhibition - 0.8963 89.63%
CYP2D6 inhibition - 0.6021 60.21%
CYP1A2 inhibition + 0.7867 78.67%
CYP2C8 inhibition + 0.5734 57.34%
CYP inhibitory promiscuity - 0.5692 56.92%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5823 58.23%
Eye corrosion - 0.9878 98.78%
Eye irritation - 0.9748 97.48%
Skin irritation - 0.7647 76.47%
Skin corrosion - 0.9410 94.10%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8454 84.54%
Micronuclear - 0.5400 54.00%
Hepatotoxicity + 0.7052 70.52%
skin sensitisation - 0.8668 86.68%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.9625 96.25%
Nephrotoxicity - 0.6487 64.87%
Acute Oral Toxicity (c) III 0.6375 63.75%
Estrogen receptor binding + 0.6792 67.92%
Androgen receptor binding + 0.7258 72.58%
Thyroid receptor binding + 0.6109 61.09%
Glucocorticoid receptor binding + 0.7965 79.65%
Aromatase binding - 0.6908 69.08%
PPAR gamma - 0.5293 52.93%
Honey bee toxicity - 0.8203 82.03%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9664 96.64%

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 98.48% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.91% 85.14%
CHEMBL241 Q14432 Phosphodiesterase 3A 95.91% 92.94%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.61% 91.11%
CHEMBL5747 Q92793 CREB-binding protein 92.66% 95.12%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.38% 94.45%
CHEMBL2535 P11166 Glucose transporter 90.75% 98.75%
CHEMBL2041 P07949 Tyrosine-protein kinase receptor RET 88.49% 91.79%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.31% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.70% 99.17%
CHEMBL4895 P30530 Tyrosine-protein kinase receptor UFO 85.65% 90.95%
CHEMBL340 P08684 Cytochrome P450 3A4 85.12% 91.19%
CHEMBL2413 P32246 C-C chemokine receptor type 1 83.00% 89.50%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.43% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.39% 89.00%
CHEMBL5028 O14672 ADAM10 82.29% 97.50%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.97% 99.23%
CHEMBL2782 P35610 Acyl coenzyme A:cholesterol acyltransferase 1 81.91% 91.65%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.90% 90.71%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.81% 97.09%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 81.47% 94.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.13% 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.
Aspidosperma discolor
Rauvolfia vomitoria

Cross-Links

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PubChem 201052
NPASS NPC184672
LOTUS LTS0041747
wikiData Q104995096