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Raucaffricine
- Family: Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@H]2/C(=C/C)/[C@@H]3C[C@@H]4N2[C@@H]2C3C([C@@]3(C2)C4=Nc2c3cccc2)OC(=O)C)[C@@H]([C@H]([C@@H]1O)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 |
| InChIKey | OSJPGOJPRNTSHP-BGYCQZOHSA-N |
| Formula | C27H32N2O8 |
| HBA | 10 |
| HBD | 4 |
| MW | 512.56 |
| Rotatable Bonds | 4 |
| TPSA | 141.28 |
| LogP | 0.14 |
| Number Rings | 8 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 37 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.63 |
| Exact Mass | 512.22 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Rauvolfia caffra | Apocynaceae | Plantae | 947877 |
Showing of synonyms
Raucaffricine
CHEBI:17400
(16S,17R,19E)-21alpha-(beta-D-glucopyranosyloxy)-1,2-didehydro-2,7-dihydro-7beta,17-cyclosarpagan-17-yl acetate
31282-07-2
((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
[(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
Vomilenine b-D-glucoside
Vomilenine I2-D-glucoside
SCHEMBL1782238
FS-9319
Q27102379
No compound-protein relationship available.
SMILES: O1CCCCC1OC2C(=C)C(C3)C(C4)C(C5)N2C3C6=Nc(c7C456)cccc7
Level: 1
Mol. Weight: 362.47 g/mol
SMILES: C=C(C1)C(C2)C(C3)C(C4)N1C2C5=Nc(c6C345)cccc6
Level: 0
Mol. Weight: 262.36 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 86.13 g/mol
Antimicrobial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -6.02
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.670
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 2.57
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.860
- Plasma Protein Binding
- 79.33
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 1.070
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -4.680
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.290
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.350
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -2405.630
- Rat (Acute)
- 2.710
- Rat (Chronic Oral)
- 2.670
- Fathead Minnow
- 5.450
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 488.980
- Hydration Free Energy
- -2.770
- Log(D) at pH=7.4
- 1.600
- Log(P)
- 0.2
- Log S
- -3.3
- Log(Vapor Pressure)
- -13.53
- Melting Point
- 205.61
- pKa Acid
- 3.38
- pKa Basic
- 7.03
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.8664 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8238 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7771 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7644 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7641 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7627 |
| Retinol-binding protein 2 | P50120 | RET2_HUMAN | Homo sapiens | 3 | 0.7597 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7463 |
| Oxygenase | Q194P4 | Q194P4_STRAA | Streptomyces argillaceus | 3 | 0.7435 |
| Large structural protein | Q91L20 | Q91L20_9MONO | Human metapneumovirus | 3 | 0.7389 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 2 | 0.7268 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 2 | 0.7203 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 3 | 0.7182 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7060 |
| Neutrophil gelatinase-associated lipocalin | P80188 | NGAL_HUMAN | Homo sapiens | 2 | 0.7042 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7023 |