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Callichiline
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | COC(=O)C1=C2Nc3c(C42[C@@H]2[C@@]5(C1)CCOC5C1CC5C6(C1N2CC4)Nc1c(C26CCN4[C@H]2[C@@]2(C5)CCOC2CC4)cccc1OC)cccc3 |
|---|---|
| InChI | InChI=1S/C42H48N4O5/c1-48-29-9-5-7-27-31(29)44-42-23(21-38-13-18-50-30(38)10-15-45-16-12-41(27,42)37(38)45)20-24-33(42)46-17-11-40-26-6-3-4-8-28(26)43-32(40)25(35(47)49-2)22-39(36(40)46)14-19-51-34(24)39/h3-9,23-24,30,33-34,36-37,43-44H,10-22H2,1-2H3/t23?,24?,30?,33?,34?,36-,37-,38+,39+,40?,41?,42?/m0/s1 |
| InChIKey | NNQIWCFSNKVVPR-OREKWXCASA-N |
| Formula | C42H48N4O5 |
| HBA | 9 |
| HBD | 2 |
| MW | 688.87 |
| Rotatable Bonds | 2 |
| TPSA | 84.53 |
| LogP | 4.82 |
| Number Rings | 13 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 51 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.64 |
| Exact Mass | 688.36 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Hedranthera barteri | Apocynaceae | Plantae | 141540 |
Showing of synonyms
Callichiline
31230-09-8
Methyl (1R,1'S,4'R,6'R,10'S,12R,14'S,15'R,16S,17R,22R)-18'-methoxyspiro[15-oxa-8,19-diazahexacyclo[10.9.1.01,9.02,7.012,16.019,22]docosa-2,4,6,9-tetraene-17,2'-9-oxa-13,16-diazaheptacyclo[11.9.2.01,15.04,15.06,10.06,14.017,22]tetracosa-17(22),18,20-triene]-10-carboxylate
C09088
CHEBI:3322
Q27106022
- Agwada V, Patel MB, et al. (1970). Die Alkaloide aus Hedranthera barteri (Hook. f.) Pichonl. 139. Mitteilung uber die Alkaloide. Helvetica Chimica Acta,1970,53(7),1567-1577. [View]
Pubchem:
5462424
Cas:
31230-09-8
Kegg Ligand:
C09088
Chebi:
3322
Nmrshiftdb2:
70070650
Comptox:
DTXSID00420143
No compound-protein relationship available.
SMILES: c1cccc(c1C234)NC2=CCC56C3N(CC4)C7C89C1(c2c(N9)cccc2)C2C3(C(OCC3)CCN2CC1)CC8CC7C5OCC6
Level: 0
Mol. Weight: 688.87 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.55
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 46.640
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 6827.37
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.260
- Plasma Protein Binding
- 70.97
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- 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
- 4.610
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -164.850
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.490
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.530
- 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
- -12393706.280
- Rat (Acute)
- 3.240
- Rat (Chronic Oral)
- 2.290
- Fathead Minnow
- 15646.590
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 1391274.080
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 5.220
- Log(P)
- 4.15
- Log S
- -4.9
- Log(Vapor Pressure)
- -45728.17
- Melting Point
- 286.49
- pKa Acid
- -284.45
- pKa Basic
- 7.68
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7830 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7830 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7211 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7211 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7210 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7210 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7116 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7116 |