Raucaffricine

Details

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Internal ID 0ab9ae45-f2f4-446d-b7cb-74e41e271b3f
Taxonomy Alkaloids and derivatives > Ajmaline-sarpagine alkaloids
IUPAC Name [(1R,10S,12R,13E,14R,16S,18R)-13-ethylidene-14-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6,8-tetraen-18-yl] acetate
SMILES (Canonical) CC=C1C2CC3C4=NC5=CC=CC=C5C46CC(C2C6OC(=O)C)N3C1OC7C(C(C(C(O7)CO)O)O)O
SMILES (Isomeric) C/C=C/1\[C@@H]2C[C@H]3C4=NC5=CC=CC=C5[C@]46C[C@@H](C2[C@H]6OC(=O)C)N3[C@@H]1O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
InChI InChI=1S/C27H32N2O8/c1-3-12-13-8-16-23-27(14-6-4-5-7-15(14)28-23)9-17(19(13)24(27)35-11(2)31)29(16)25(12)37-26-22(34)21(33)20(32)18(10-30)36-26/h3-7,13,16-22,24-26,30,32-34H,8-10H2,1-2H3/b12-3+/t13-,16-,17-,18+,19?,20+,21-,22+,24+,25+,26-,27+/m0/s1
InChI Key OSJPGOJPRNTSHP-ICYIRATMSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C27H32N2O8
Molecular Weight 512.60 g/mol
Exact Mass 512.21586598 g/mol
Topological Polar Surface Area (TPSA) 141.00 Ų
XlogP -0.20
Atomic LogP (AlogP) 0.14
H-Bond Acceptor 10
H-Bond Donor 4
Rotatable Bonds 4

Synonyms

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(16S,17R,19E)-21alpha-(beta-D-glucopyranosyloxy)-1,2-didehydro-2,7-dihydro-7beta,17-cyclosarpagan-17-yl acetate
Vomilenine beta-D-glucoside
31282-07-2
SCHEMBL1782238
CHEBI:17400
C02074
Q27102379

2D Structure

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2D Structure of Raucaffricine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6476 64.76%
Caco-2 - 0.7798 77.98%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.5606 56.06%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8440 84.40%
OATP1B3 inhibitior + 0.9355 93.55%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.7850 78.50%
P-glycoprotein inhibitior - 0.4463 44.63%
P-glycoprotein substrate + 0.5277 52.77%
CYP3A4 substrate + 0.6857 68.57%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8713 87.13%
CYP3A4 inhibition - 0.8803 88.03%
CYP2C9 inhibition - 0.8056 80.56%
CYP2C19 inhibition - 0.7944 79.44%
CYP2D6 inhibition - 0.8974 89.74%
CYP1A2 inhibition - 0.7193 71.93%
CYP2C8 inhibition + 0.5886 58.86%
CYP inhibitory promiscuity - 0.6935 69.35%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9000 90.00%
Carcinogenicity (trinary) Non-required 0.5908 59.08%
Eye corrosion - 0.9841 98.41%
Eye irritation - 0.9672 96.72%
Skin irritation - 0.7673 76.73%
Skin corrosion - 0.9300 93.00%
Ames mutagenesis + 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4026 40.26%
Micronuclear + 0.7600 76.00%
Hepatotoxicity - 0.6410 64.10%
skin sensitisation - 0.8247 82.47%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.8875 88.75%
Nephrotoxicity + 0.6702 67.02%
Acute Oral Toxicity (c) III 0.5608 56.08%
Estrogen receptor binding + 0.8028 80.28%
Androgen receptor binding + 0.7022 70.22%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding - 0.4900 49.00%
Aromatase binding - 0.4863 48.63%
PPAR gamma + 0.6209 62.09%
Honey bee toxicity - 0.7440 74.40%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6155 61.55%
Fish aquatic toxicity + 0.8862 88.62%

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 98.80% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.56% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.82% 86.33%
CHEMBL2581 P07339 Cathepsin D 91.24% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.13% 94.45%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.68% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.66% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.17% 95.56%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 85.92% 95.83%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 83.44% 94.62%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.08% 96.00%
CHEMBL5028 O14672 ADAM10 82.76% 97.50%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.41% 97.25%
CHEMBL3891 P07384 Calpain 1 82.39% 93.04%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 81.28% 100.00%

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.
Rauvolfia serpentina

Cross-Links

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PubChem 5280486
NPASS NPC260940