Structure

Physi-Chem Properties

Molecular Weight:  462.19
Volume:  458.648
LogP:  0.86
LogD:  0.581
LogS:  -2.319
# Rotatable Bonds:  10
TPSA:  156.91
# H-Bond Aceptor:  9
# H-Bond Donor:  6
# Rings:  3
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.285
Synthetic Accessibility Score:  3.961
Fsp3:  0.458
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.732
MDCK Permeability:  7.214603556349175e-06
Pgp-inhibitor:  0.013
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.922
20% Bioavailability (F20%):  0.987
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.034
Plasma Protein Binding (PPB):  85.89396667480469%
Volume Distribution (VD):  0.538
Pgp-substrate:  11.763260841369629%

ADMET: Metabolism

CYP1A2-inhibitor:  0.049
CYP1A2-substrate:  0.055
CYP2C19-inhibitor:  0.099
CYP2C19-substrate:  0.057
CYP2C9-inhibitor:  0.304
CYP2C9-substrate:  0.81
CYP2D6-inhibitor:  0.457
CYP2D6-substrate:  0.727
CYP3A4-inhibitor:  0.034
CYP3A4-substrate:  0.083

ADMET: Excretion

Clearance (CL):  7.427
Half-life (T1/2):  0.921

ADMET: Toxicity

hERG Blockers:  0.169
Human Hepatotoxicity (H-HT):  0.289
Drug-inuced Liver Injury (DILI):  0.032
AMES Toxicity:  0.726
Rat Oral Acute Toxicity:  0.153
Maximum Recommended Daily Dose:  0.787
Skin Sensitization:  0.949
Carcinogencity:  0.193
Eye Corrosion:  0.003
Eye Irritation:  0.138
Respiratory Toxicity:  0.109

Download Data

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

  Natural Product: NPC258442

Natural Product ID:  NPC258442
Common Name*:   PLPIXLSRTIVHDP-KGLIPLIRSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  PLPIXLSRTIVHDP-KGLIPLIRSA-N
Standard InCHI:  InChI=1S/C14H14O5/c1-18-10-7-11(19-12(15)8-10)14(17)13(16)9-5-3-2-4-6-9/h2-8,13-14,16-17H,1H3/t13-,14+/m1/s1
SMILES:  COc1cc([C@@H]([C@@H](c2ccccc2)O)O)oc(=O)c1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0001761] Kavalactones

*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
NPO8171 Artocarpus altilis Species Moraceae Eukaryota bud covers n.a. n.a. PMID[11975520]
NPO18596 Melia dubia Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[12502333]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. root n.a. PMID[12662107]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18529 Salvia broussoneti Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18762 Ilex microdonta Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18259 Chaetanthera chilensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8171 Artocarpus altilis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20691 Echinocereus merkeri Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19082 Creolophus cirrhatus Species Hericiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18596 Melia dubia Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19008 Mentha cablin Species Lamiaceae 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 NPC258442 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 NPC258442 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