Structure

Physi-Chem Properties

Molecular Weight:  192.08
Volume:  203.444
LogP:  2.688
LogD:  3.084
LogS:  -2.837
# Rotatable Bonds:  4
TPSA:  35.53
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.542
Synthetic Accessibility Score:  1.648
Fsp3:  0.182
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.489
MDCK Permeability:  2.3642322048544884e-05
Pgp-inhibitor:  0.521
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.675
30% Bioavailability (F30%):  0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.992
Plasma Protein Binding (PPB):  90.58528137207031%
Volume Distribution (VD):  0.719
Pgp-substrate:  8.875646591186523%

ADMET: Metabolism

CYP1A2-inhibitor:  0.977
CYP1A2-substrate:  0.939
CYP2C19-inhibitor:  0.879
CYP2C19-substrate:  0.82
CYP2C9-inhibitor:  0.548
CYP2C9-substrate:  0.849
CYP2D6-inhibitor:  0.149
CYP2D6-substrate:  0.888
CYP3A4-inhibitor:  0.222
CYP3A4-substrate:  0.506

ADMET: Excretion

Clearance (CL):  9.739
Half-life (T1/2):  0.822

ADMET: Toxicity

hERG Blockers:  0.174
Human Hepatotoxicity (H-HT):  0.752
Drug-inuced Liver Injury (DILI):  0.236
AMES Toxicity:  0.446
Rat Oral Acute Toxicity:  0.316
Maximum Recommended Daily Dose:  0.209
Skin Sensitization:  0.953
Carcinogencity:  0.416
Eye Corrosion:  0.03
Eye Irritation:  0.572
Respiratory Toxicity:  0.778

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC28384

Natural Product ID:  NPC28384
Common Name*:   VEZIKIAGFYZTCI-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  VEZIKIAGFYZTCI-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H12O3/c1-13-10-6-3-9(4-7-10)5-8-11(12)14-2/h3-8H,1-2H3
SMILES:  COc1ccc(cc1)C=CC(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   92841
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0003480] Cinnamic acid esters

*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
NPO19434 Securinega suffruticosa Species Phyllanthaceae Eukaryota n.a. callus n.a. PMID[16327202]
NPO19434 Securinega suffruticosa Species Phyllanthaceae Eukaryota Twigs n.a. n.a. PMID[31082231]
NPO19434 Securinega suffruticosa Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19434 Securinega suffruticosa Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19434 Securinega suffruticosa Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8525 Pinus torreyana Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18598 Languas galanga n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO143.1 Tephrosia purpurea subsp. apollinea Subspecies Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1619 Lactuca triangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19434 Securinega suffruticosa Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13458 Acarospora montana Species Acarosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3455 Picramnia lindeniana Species Picramniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18302 Chondrostereum purpureum Species Schizophyllaceae 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 NPC28384 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 NPC28384 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