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Latifolianine A
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Monoterpenoid Indole Alkaloid
| Canonical Smiles | OC[C@]12COC(O[C@H]1CC[C@]1(C2CC[C@@]2(C1CC=C1[C@@]2(C)CC[C@@]2(C1[C@](C)(O)[C@@H](CC2)C)C(=O)O)C)C)C1[C@@H](C)OC=C2[C@H]1C[C@@H]1N(C2=O)CCc2c1[nH]c1c2cccc1 |
|---|---|
| InChI | InChI=1S/C50H66N2O8/c1-27-13-19-49(44(55)56)21-20-46(4)33(41(49)48(27,6)57)11-12-36-45(3)17-15-38-50(25-53,37(45)14-18-47(36,46)5)26-59-43(60-38)39-28(2)58-24-32-31(39)23-35-40-30(16-22-52(35)42(32)54)29-9-7-8-10-34(29)51-40/h7-11,24,27-28,31,35-39,41,43,51,53,57H,12-23,25-26H2,1-6H3,(H,55,56)/t27-,28-,31-,35+,36?,37?,38+,39?,41?,43?,45-,46-,47-,48-,49+,50-/m1/s1 |
| InChIKey | LCZVPHZDOMBTOO-FAGCCURNSA-N |
| Formula | C50H66N2O8 |
| HBA | 7 |
| HBD | 4 |
| MW | 823.08 |
| Rotatable Bonds | 3 |
| TPSA | 141.55 |
| LogP | 8.08 |
| Number Rings | 11 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 60 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.72 |
| Exact Mass | 822.48 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Nauclea latifolia | Rubiaceae | Plantae | 43573 |
Showing of synonyms
Latifolianine A
No compound-protein relationship available.
SMILES: c1cccc2[nH]c(c3c12)C4N(CC3)C(=O)C=5C(C4)C(COC5)C(OC6)OC(CC7)C6C(CC8)C7C(CC9)C8C(C1=9)CCC2C1CCCC2
Level: 1
Mol. Weight: 823.08 g/mol
SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)C6C(CC5)OCOC6
Level: 0
Mol. Weight: 823.08 g/mol
SMILES: c1cccc2[nH]c(c3c12)C4N(CC3)C(=O)C=5C(C4)CCOC5
Level: 0
Mol. Weight: 823.08 g/mol
Antibacterial
Absorption
- Caco-2 (logPapp)
- -5.58
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- 864.59
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 113740.28
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.65
- Plasma Protein Binding
- 91.85
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- 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
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 4.51
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -2648.27
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.34
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 4.27
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -206433968.43
- Rat (Acute)
- 3.92
- Rat (Chronic Oral)
- 2.3
- Fathead Minnow
- 260583.48
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 23214765.43
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 2.4
- Log(P)
- 6.58
- Log S
- -6.19
- Log(Vapor Pressure)
- -764358.0
- Melting Point
- 346.16
- pKa Acid
- -5498.68
- pKa Basic
- -14.03
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8843 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.8657 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8650 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8602 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8421 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8244 |
| Nitric oxide synthase, inducible | P35228 | NOS2_HUMAN | Homo sapiens | 3 | 0.8234 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 3 | 0.8088 |
| Caspase-7 | P55210 | CASP7_HUMAN | Homo sapiens | 3 | 0.8035 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7888 |
| Aldo-keto reductase family 1 member B10 | O60218 | AK1BA_HUMAN | Homo sapiens | 3 | 0.7852 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7831 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7825 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7825 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7806 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7759 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7698 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7685 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7672 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7656 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7643 |
| Epoxide hydrolase | Q41415 | Q41415_SOLTU | Solanum tuberosum | 3 | 0.7621 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7590 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7589 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7583 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 2 | 0.7568 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.7562 |
| Acetylcholinesterase | P22303 | ACES_HUMAN | Homo sapiens | 2 | 0.7531 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7527 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | O67060 | ISPE_AQUAE | Aquifex aeolicus | 3 | 0.7522 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7521 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7489 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7480 |
| Branched-chain-amino-acid aminotransferase, mitochondrial | O15382 | BCAT2_HUMAN | Homo sapiens | 3 | 0.7461 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7445 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 4 | 0.7438 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7414 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7412 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7395 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7387 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.7356 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 2 | 0.7340 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7313 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 3 | 0.7270 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7250 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 2 | 0.7238 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 2 | 0.7228 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 2 | 0.7164 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 2 | 0.7160 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7156 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7132 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 2 | 0.7117 |
| Gentisate 1,2-dioxygenase | Q67FT0 | Q67FT0_PSESE | Pseudaminobacter salicylatoxidans | 2 | 0.7117 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7103 |
| Carboxyethyl-arginine beta-lactam-synthase | P0DJQ7 | BLS_STRCL | Streptomyces clavuligerus | 3 | 0.7090 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7073 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7047 |
| Aldo-keto reductase family 1 member B1 | P80276 | ALDR_PIG | Sus scrofa | 3 | 0.7033 |
| Adenosylmethionine-8-amino-7-oxononanoate aminotransferase | P12995 | BIOA_ECOLI | Escherichia coli | 2 | 0.7013 |