Structure

Physi-Chem Properties

Molecular Weight:  336.18
Volume:  346.825
LogP:  2.011
LogD:  2.323
LogS:  -4.089
# Rotatable Bonds:  0
TPSA:  55.56
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.741
Synthetic Accessibility Score:  5.696
Fsp3:  0.571
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.893
MDCK Permeability:  4.12239387515001e-05
Pgp-inhibitor:  0.258
Pgp-substrate:  0.734
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  0.976
30% Bioavailability (F30%):  0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.957
Plasma Protein Binding (PPB):  53.864505767822266%
Volume Distribution (VD):  0.849
Pgp-substrate:  47.580570220947266%

ADMET: Metabolism

CYP1A2-inhibitor:  0.072
CYP1A2-substrate:  0.404
CYP2C19-inhibitor:  0.057
CYP2C19-substrate:  0.811
CYP2C9-inhibitor:  0.068
CYP2C9-substrate:  0.07
CYP2D6-inhibitor:  0.022
CYP2D6-substrate:  0.364
CYP3A4-inhibitor:  0.81
CYP3A4-substrate:  0.726

ADMET: Excretion

Clearance (CL):  8.187
Half-life (T1/2):  0.33

ADMET: Toxicity

hERG Blockers:  0.358
Human Hepatotoxicity (H-HT):  0.335
Drug-inuced Liver Injury (DILI):  0.248
AMES Toxicity:  0.04
Rat Oral Acute Toxicity:  0.469
Maximum Recommended Daily Dose:  0.969
Skin Sensitization:  0.347
Carcinogencity:  0.846
Eye Corrosion:  0.003
Eye Irritation:  0.017
Respiratory Toxicity:  0.917

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General Info & Identifiers & Properties  
Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC147754

Natural Product ID:  NPC147754
Common Name*:   MEKVEXUSONMODA-FVWCLLPLSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  MEKVEXUSONMODA-FVWCLLPLSA-N
Standard InCHI:  InChI=1S/C21H24N2O2/c22-17-10-13-12-4-3-8-21(17)14-5-1-2-6-15(14)23-18(24)11-16(25-9-7-12)19(13)20(21)23/h1-2,5-7,13,16-17,19-20H,3-4,8-11,22H2/t13-,16-,17-,19-,20-,21+/m0/s1
SMILES:  c1ccc2c(c1)[C@]13CCCC4=CCO[C@H]5CC(=O)N2[C@H]3[C@H]5[C@H]4C[C@@H]1N
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   57394605
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0000210] Carbazoles

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. DOI[10.1016/j.tet.2012.03.006]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[10.1016/j.tet.2012.03.006]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota leaves Niigata City, Niigata Province, Japan 2000-Nov PMID[15730243]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[16317898]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota leaves n.a. n.a. PMID[16933868]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[17253842]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[17449162]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota stems and twigs Niigata City, Niigata Province, Japan 2001-NOV PMID[17595134]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota stems and twigs n.a. n.a. PMID[17595134]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[19235686]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[19666019]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[22707864]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[23088673]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[2393954]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[25594733]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[29693393]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[7912074]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota Leaves; Stems n.a. n.a. PMID[9214727]
NPO1934 Strychnos triplinervia Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO570 Semen holarrhenae n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23053 Strychnos nitida Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31396 Nerium indicum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1934 Strychnos triplinervia Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23053 Strychnos nitida Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO570 Semen holarrhenae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO23053 Strychnos nitida Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31396 Nerium indicum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1934 Strychnos triplinervia Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23053 Strychnos nitida Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10021 Nerium oleander Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC147754 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC147754 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data