Structure

Physi-Chem Properties

Molecular Weight:  197.11
Volume:  202.418
LogP:  2.724
LogD:  1.555
LogS:  -2.836
# Rotatable Bonds:  3
TPSA:  73.32
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.65
Synthetic Accessibility Score:  3.605
Fsp3:  0.5
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:  -4.696
MDCK Permeability:  1.0883042705245316e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.308
Plasma Protein Binding (PPB):  93.85601043701172%
Volume Distribution (VD):  0.809
Pgp-substrate:  5.354063034057617%

ADMET: Metabolism

CYP1A2-inhibitor:  0.819
CYP1A2-substrate:  0.936
CYP2C19-inhibitor:  0.09
CYP2C19-substrate:  0.085
CYP2C9-inhibitor:  0.449
CYP2C9-substrate:  0.653
CYP2D6-inhibitor:  0.45
CYP2D6-substrate:  0.261
CYP3A4-inhibitor:  0.215
CYP3A4-substrate:  0.293

ADMET: Excretion

Clearance (CL):  3.571
Half-life (T1/2):  0.788

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.157
Drug-inuced Liver Injury (DILI):  0.95
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.875
Maximum Recommended Daily Dose:  0.04
Skin Sensitization:  0.25
Carcinogencity:  0.362
Eye Corrosion:  0.003
Eye Irritation:  0.589
Respiratory Toxicity:  0.96

Download Data

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

  Natural Product: NPC4706

Natural Product ID:  NPC4706
Common Name*:   Tenuazonic Acid
IUPAC Name:   (2S)-4-acetyl-2-[(2S)-butan-2-yl]-3-hydroxy-1,2-dihydropyrrol-5-one
Synonyms:   tenuazonic acid
Standard InCHIKey:  CEIZFXOZIQNICU-XNCJUZBTSA-N
Standard InCHI:  InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14)/t5-,8-/m0/s1
SMILES:  CC[C@@H]([C@@H]1N=C(C(=C1O)C(=O)C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL511015
PubChem CID:   54683011
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000091] Pyrrolines

*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
NPO32908 Alternaria sp. Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[18494522]
NPO32908 Alternaria sp. Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[22276679]
NPO32908 Alternaria sp. Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[25265160]
NPO32908 Alternaria sp. Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[26841051]
NPO32908 Alternaria sp. Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[30794407]

☑ 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
NPT1864 Cell Line L5178Y Mus musculus Activity = 57.9 % PMID[543079]

☑ 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 NPC4706 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
0.8219 Intermediate Similarity NPC469835
0.7945 Intermediate Similarity NPC469836
0.7407 Intermediate Similarity NPC469833
0.7407 Intermediate Similarity NPC469838
0.6875 Remote Similarity NPC263266
0.6458 Remote Similarity NPC313234
0.6289 Remote Similarity NPC175531
0.6235 Remote Similarity NPC471597
0.6162 Remote Similarity NPC474563
0.5978 Remote Similarity NPC34754
0.5962 Remote Similarity NPC476290
0.5946 Remote Similarity NPC245650
0.5926 Remote Similarity NPC471022
0.5922 Remote Similarity NPC140251
0.5922 Remote Similarity NPC307903
0.5921 Remote Similarity NPC6795
0.59 Remote Similarity NPC469598
0.5888 Remote Similarity NPC476813
0.5888 Remote Similarity NPC476814
0.5865 Remote Similarity NPC24389
0.5849 Remote Similarity NPC476269
0.5844 Remote Similarity NPC273614
0.5844 Remote Similarity NPC29468
0.5816 Remote Similarity NPC4834
0.5789 Remote Similarity NPC472264
0.5732 Remote Similarity NPC45060
0.5732 Remote Similarity NPC280065
0.5682 Remote Similarity NPC314854
0.5682 Remote Similarity NPC313911
0.567 Remote Similarity NPC116930
0.5667 Remote Similarity NPC224072
0.5667 Remote Similarity NPC39966
0.5636 Remote Similarity NPC476190
0.56 Remote Similarity NPC40148

  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 NPC4706 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
NPD

  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