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Moandaensine
- Family: Plantae - Loganiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | CC[C@H]1C[n+]2cc(C[C@@H]([C@H]3C[C@@H]4N(C/C/3=C/C)CCC3C4Nc4c3cccc4)C(=O)OC)c3c(c2C[C@@H]1[C@@H](C(=O)OC)CO)[n-]c1c3cccc1 |
|---|---|
| InChI | InChI=1S/C42H50N4O5/c1-5-24-20-45-16-15-28-27-11-7-9-13-34(27)43-39(28)36(45)18-30(24)32(41(48)50-3)17-26-22-46-21-25(6-2)31(33(23-47)42(49)51-4)19-37(46)40-38(26)29-12-8-10-14-35(29)44-40/h5,7-14,22,25,28,30-33,36,39,43,47H,6,15-21,23H2,1-4H3/b24-5-/t25-,28?,30-,31-,32-,33-,36-,39?/m0/s1 |
| InChIKey | SESFDOOCQVZCAR-WIRBRKJASA-N |
| Formula | C42H50N4O5 |
| HBA | 7 |
| HBD | 2 |
| MW | 690.89 |
| Rotatable Bonds | 8 |
| TPSA | 106.08 |
| LogP | 5.17 |
| Number Rings | 8 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 51 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 690.38 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Strychnos moandaensis | Loganiaceae | Plantae | 26496 |
Showing of synonyms
Moandaensine
- Verpoorte R, Frédérich M, et al. (2010). Moandaensine, a dimeric indole alkaloid from Strychnos moandaensis (Loganiaceae). Phytochemistry Letters, 2010, 3(2), 100-103. [View]
No compound-protein relationship available.
SMILES: c1cccc(c12)NC3C2CCN4C3CC(C(=C)C4)CCc5c[n+](CCCC6)c6c7[n-]c(c8c57)cccc8
Level: 1
Mol. Weight: 690.89 g/mol
SMILES: C=C(C1)CCC2N1CCC3C2Nc(c34)cccc4
Level: 0
Mol. Weight: 690.89 g/mol
SMILES: c1cccc(c1c23)[n-]c2c4[n+](cc3)CCCC4
Level: 0
Mol. Weight: 690.89 g/mol
Anti-plasmodial
Absorption
- Caco-2 (logPapp)
- -5.67
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- 9.59
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 1939.21
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.29
- Plasma Protein Binding
- 93.31
- 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
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 7.06
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -48.25
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.03
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.87
- 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
- Toxic
- T. Pyriformis
- -3522768.34
- Rat (Acute)
- 2.82
- Rat (Chronic Oral)
- 1.38
- Fathead Minnow
- 4451.78
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 392708.32
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 5.1
- Log(P)
- 4.01
- Log S
- -3.28
- Log(Vapor Pressure)
- -12862.05
- Melting Point
- 235.76
- pKa Acid
- -56.03
- pKa Basic
- 5.34
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9148 |
| clade A/E 93TH057 HIV-1 gp120 core | A0A0M3KKW9 | A0A0M3KKW9_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.9109 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.9006 |
| Caspase-6 | P55212 | CASP6_HUMAN | Homo sapiens | 3 | 0.8898 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.8757 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.8619 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8536 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.8511 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8488 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.8352 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 3 | 0.8136 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8104 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7973 |
| Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 2 | 0.7954 |
| rRNA methylase | Q8DSS3 | Q8DSS3_STRMU | Streptococcus mutans serotype c | 2 | 0.7947 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7895 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7851 |
| Nitric oxide synthase, inducible | P35228 | NOS2_HUMAN | Homo sapiens | 3 | 0.7848 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7845 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7814 |
| cAMP-dependent protein kinase type II-beta regulatory subunit | P12369 | KAP3_RAT | Rattus norvegicus | 3 | 0.7781 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7637 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7605 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7590 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7579 |
| Interleukin-2 | P60568 | IL2_HUMAN | Homo sapiens | 3 | 0.7561 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7556 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7552 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7544 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7521 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7499 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 2 | 0.7497 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7495 |
| Histidinol dehydrogenase | P06988 | HISX_ECOLI | Escherichia coli | 2 | 0.7488 |
| Nickel-binding periplasmic protein | P33590 | NIKA_ECOLI | Escherichia coli | 2 | 0.7482 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 2 | 0.7458 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7456 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7408 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7402 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7389 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7364 |
| L-lactate dehydrogenase A chain | P13491 | LDHA_RABIT | Oryctolagus cuniculus | 2 | 0.7356 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7337 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 2 | 0.7331 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 2 | 0.7325 |
| Gentisate 1,2-dioxygenase | Q67FT0 | Q67FT0_PSESE | Pseudaminobacter salicylatoxidans | 2 | 0.7319 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7316 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7315 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7306 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 2 | 0.7305 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7295 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7290 |
| Antibiotic ABC transporter, ATP-binding protein, putative | Q9X1C3 | Q9X1C3_THEMA | Thermotoga maritima | 3 | 0.7279 |
| Putative snRNP Sm-like protein | Q8ZYG5 | Q8ZYG5_PYRAE | Pyrobaculum aerophilum | 2 | 0.7278 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7273 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7269 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7263 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 2 | 0.7257 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7256 |
| Chorismate pyruvate-lyase | P26602 | UBIC_ECOLI | Escherichia coli | 2 | 0.7253 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7247 |
| Ribosomal protein S6 kinase beta-1 | P23443 | KS6B1_HUMAN | Homo sapiens | 3 | 0.7227 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 2 | 0.7219 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7208 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7206 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7201 |
| Feruloyl esterase A | O42807 | FAEA_ASPNG | Aspergillus niger | 2 | 0.7200 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 2 | 0.7195 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 2 | 0.7192 |
| Bifunctional protein GlmU | P43889 | GLMU_HAEIN | Haemophilus influenzae | 3 | 0.7185 |
| DNA mismatch repair protein MutS | Q56215 | MUTS_THEAQ | Thermus aquaticus | 2 | 0.7185 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 2 | 0.7160 |
| Serine/threonine-protein kinase TBK1 | Q9UHD2 | TBK1_HUMAN | Homo sapiens | 4 | 0.7155 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7153 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7153 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 2 | 0.7152 |
| 4-substituted benzoates-glutamate ligase GH3.12 | Q9LYU4 | GH312_ARATH | Arabidopsis thaliana | 2 | 0.7152 |
| Adenosylmethionine-8-amino-7-oxononanoate aminotransferase | P12995 | BIOA_ECOLI | Escherichia coli | 2 | 0.7151 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7150 |
| Carbonic anhydrase 5A, mitochondrial | P23589 | CAH5A_MOUSE | Mus musculus | 2 | 0.7150 |
| Sterol 14alpha-demethylase | P9WPP9 | CP51_MYCTU | Mycobacterium tuberculosis | 3 | 0.7148 |
| Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2 | O95340 | PAPS2_HUMAN | Homo sapiens | 2 | 0.7141 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7125 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 2 | 0.7117 |
| Toluene-4-monooxygenase system, hydroxylase component subunit alpha | Q00456 | TMOA_PSEME | Pseudomonas mendocina | 2 | 0.7112 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 4 | 0.7106 |
| adenine phosphoribosyltransferase | Q967M2 | Q967M2_GIAIN | Giardia intestinalis | 2 | 0.7105 |
| Caffeic acid 3-O-methyltransferase | P28002 | COMT1_MEDSA | Medicago sativa | 2 | 0.7102 |
| Adenosine 5'-monophosphoramidase HINT1 | P80912 | HINT1_RABIT | Oryctolagus cuniculus | 3 | 0.7100 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7097 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7087 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7085 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 2 | 0.7071 |
| Tryptophan synthase alpha chain | P00929 | TRPA_SALTY | Salmonella typhimurium | 2 | 0.7061 |
| Karilysin | D0EM77 | KLY_TANFA | Tannerella forsythia | 2 | 0.7050 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7048 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7046 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7046 |
| Type IV pilus retractation ATPase PilT | P24559 | PILT_PSEAE | Pseudomonas aeruginosa | 3 | 0.7040 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7031 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 2 | 0.7018 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7007 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7002 |