Aspidospermidine - Compound Card

Aspidospermidine

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Aspidospermidine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CCC12CCCN3C2C2(C(CC1)Nc1c2cccc1)CC3
InChI InChI=1S/C19H26N2/c1-2-18-9-5-12-21-13-11-19(17(18)21)14-6-3-4-7-15(14)20-16(19)8-10-18/h3-4,6-7,16-17,20H,2,5,8-13H2,1H3
InChIKey YAAIPCQYJYPITK-UHFFFAOYSA-N
Formula C19H26N2
HBA 2
HBD 1
MW 282.43
Rotatable Bonds 1
TPSA 15.27
LogP 3.78
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 282.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pachypodium lamerei Apocynaceae Plantae 69385

Showing of synonyms

  • Mina S.A, Mohamed S.A, et al. (2020). LC-ESI-MS/MS profiling of alkaloids and antiproliferative activity of Pachypoduim lamerei drake leaves. Natural product research, 2020, 34(9), 1292-1296. [View] [PubMed]
Pubchem: 580281
Chebi: 174012
Nmrshiftdb2: 70076649

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1C234)NC3CCC5C2N(CC4)CCC5

Level: 0

Mol. Weight: 282.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.09
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.67
Plasma Protein Binding
11.65
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.69
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
1.12
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.85
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.1
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
4.06
Rat (Acute)
3.33
Rat (Chronic Oral)
1.63
Fathead Minnow
4.02
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
373.37
Hydration Free Energy
-4.95
Log(D) at pH=7.4
2.84
Log(P)
3.87
Log S
-2.78
Log(Vapor Pressure)
-6.47
Melting Point
123.51
pKa Acid
13.36
pKa Basic
8.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9380
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8697
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8423
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.8167
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8137
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8094
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.8046
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7988
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7850
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7831
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7814
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7791
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7776
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7757
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7746
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7703
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7663
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7642
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7638
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7619
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 2 0.7564
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7552
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7473
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7455
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7454
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7393
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7378
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7378
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7331
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7324
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 2 0.7305
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7279
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7273
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7268
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7267
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7266
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7264
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7256
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 2 0.7256
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7243
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 2 0.7230
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7224
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7220
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7217
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7206
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7187
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7187
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7184
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 2 0.7148
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7148
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 2 0.7143
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7127
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7116
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7106
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7104
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7096
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7094
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7093
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7091
Feruloyl esterase A O42807 FAEA_ASPNG Aspergillus niger 2 0.7089
Arginine kinase O15992 KARG_ANTJA Anthopleura japonica 2 0.7085
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7084
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7077
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 2 0.7075
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7071
Pyruvate dehydrogenase E1 component subunit alpha P21873 ODPA_GEOSE Geobacillus stearothermophilus 3 0.7069
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7064
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7063
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7049
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7045
Candida glabrata strain CBS138 chromosome E complete sequence Q6FV03 Q6FV03_CANGA Candida glabrata 2 0.7018
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7009

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