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ASPIDOSPERMINE
ID: ALA519457
Max Phase: Preclinical
Molecular Formula: C22H30N2O2
Molecular Weight: 354.49
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): Aspidospermine
Synonyms from Alternative Forms(1):
Canonical SMILES: CC[C@@]12CCCN3CC[C@]4(c5cccc(OC)c5N(C(C)=O)[C@@H]4CC1)[C@H]32
Standard InChI: InChI=1S/C22H30N2O2/c1-4-21-10-6-13-23-14-12-22(20(21)23)16-7-5-8-17(26-3)19(16)24(15(2)25)18(22)9-11-21/h5,7-8,18,20H,4,6,9-14H2,1-3H3/t18-,20-,21-,22-/m1/s1
Standard InChI Key: ARQOGCYMPUOVHK-ZHHKINOHSA-N
Associated Targets(Human)
SN12C 47755 Activities
MDA-N 28205 Activities
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NCI-H23 49055 Activities
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ACHN 49357 Activities
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UO-31 46270 Activities
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HOP-92 41141 Activities
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HL-60 67320 Activities
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SF-539 44845 Activities
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DU-145 51482 Activities
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SK-MEL-5 47095 Activities
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Malme-3M 44254 Activities
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A498 42825 Activities
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OVCAR-3 48710 Activities
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MOLT-4 49676 Activities
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HOP-62 47048 Activities
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NCI/ADR-RES 33767 Activities
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U-251 51189 Activities
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OVCAR-5 45555 Activities
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OVCAR-8 47708 Activities
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MDA-MB-231 73002 Activities
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SNB-19 46794 Activities
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TK-10 45540 Activities
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SR 39847 Activities
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SW-620 52400 Activities
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NCI-H522 44358 Activities
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KM12 47707 Activities
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M14 47487 Activities
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NCI-H322M 45589 Activities
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RPMI-8226 44974 Activities
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OVCAR-4 44535 Activities
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LOX IMVI 44321 Activities
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BT-549 31254 Activities
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SK-MEL-2 46422 Activities
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A549 127892 Activities
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HCC 2998 41480 Activities
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HCT-15 51914 Activities
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HCT-116 91556 Activities
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SF-268 49410 Activities
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MCF7 126967 Activities
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EKVX 44102 Activities
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PC-3 62116 Activities
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SK-OV-3 52876 Activities
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T47D 39041 Activities
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NCI-H460 60772 Activities
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UACC-62 47335 Activities
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CAKI-1 44928 Activities
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MDA-MB-435 38290 Activities
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SF-295 48000 Activities
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IGROV-1 47897 Activities
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Hs-578T 29457 Activities
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UACC-257 46019 Activities
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786-0 47912 Activities
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CCRF-CEM 65223 Activities
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NCI-H226 44470 Activities
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HT-29 80576 Activities
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SK-MEL-28 48833 Activities
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RXF 393 41971 Activities
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COLO 205 50209 Activities
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Associated Targets(non-human)
Human immunodeficiency virus type 1 reverse transcriptase 18245 Activities
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Trypanothione reductase 965 Activities
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NIH3T3 5395 Activities
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Leishmania amazonensis 3813 Activities
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Glutathione reductase 23 Activities
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Molecule Features
| Natural Product: Yes | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 354.49 | Molecular Weight (Monoisotopic): 354.2307 | AlogP: 3.73 | #Rotatable Bonds: 2 |
| Polar Surface Area: 32.78 | Molecular Species: BASE | HBA: 3 | HBD: 0 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 9.86 | CX LogP: 2.78 | CX LogD: 0.36 |
| Aromatic Rings: 1 | Heavy Atoms: 26 | QED Weighted: 0.81 | Np Likeness Score: 1.71 |
References
| 1. Galarreta BC, Sifuentes R, Carrillo AK, Sanchez L, Amado Mdel R, Maruenda H.. (2008) The use of natural product scaffolds as leads in the search for trypanothione reductase inhibitors., 16 (14): [PMID:18558492] [10.1016/j.bmc.2008.05.074] |
| 2. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH.. (1991) Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase., 54 (1): [PMID:1710653] [10.1021/np50073a012] |
| 3. PubChem BioAssay data set, |
Source
Source(2):