Structure

Physi-Chem Properties

Molecular Weight:  166.1
Volume:  182.631
LogP:  2.578
LogD:  2.147
LogS:  -1.696
# Rotatable Bonds:  1
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.629
Synthetic Accessibility Score:  2.13
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.567
MDCK Permeability:  2.5328377887490205e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.899
30% Bioavailability (F30%):  0.936

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.528
Plasma Protein Binding (PPB):  96.9413833618164%
Volume Distribution (VD):  1.644
Pgp-substrate:  2.430922031402588%

ADMET: Metabolism

CYP1A2-inhibitor:  0.816
CYP1A2-substrate:  0.955
CYP2C19-inhibitor:  0.228
CYP2C19-substrate:  0.629
CYP2C9-inhibitor:  0.349
CYP2C9-substrate:  0.662
CYP2D6-inhibitor:  0.539
CYP2D6-substrate:  0.783
CYP3A4-inhibitor:  0.083
CYP3A4-substrate:  0.361

ADMET: Excretion

Clearance (CL):  11.436
Half-life (T1/2):  0.848

ADMET: Toxicity

hERG Blockers:  0.005
Human Hepatotoxicity (H-HT):  0.029
Drug-inuced Liver Injury (DILI):  0.044
AMES Toxicity:  0.029
Rat Oral Acute Toxicity:  0.714
Maximum Recommended Daily Dose:  0.347
Skin Sensitization:  0.911
Carcinogencity:  0.608
Eye Corrosion:  0.073
Eye Irritation:  0.954
Respiratory Toxicity:  0.402

Download Data

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

  Natural Product: NPC169113

Natural Product ID:  NPC169113
Common Name*:   SLJOISSFRPVUJK-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  SLJOISSFRPVUJK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H14O2/c1-6(2)8-5-4-7(3)9(11)10(8)12/h11H,4-5H2,1-3H3
SMILES:  CC(=C1CCC(=C(C1=O)O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   85624171
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001401] Menthane monoterpenoids

*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
NPO3799 Philinopsis speciosa Species Aglajidae Eukaryota n.a. n.a. n.a. PMID[15332851]
NPO5652 Barleria lupulina Species Acanthaceae Eukaryota aerial part purchased in Vung Tau, Vietnam 2012-MAR PMID[25611215]
NPO5652 Barleria lupulina Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5652 Barleria lupulina Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6613 Casimiroa pubescens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5652 Barleria lupulina Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1908 Isolona hexaloba Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3799 Philinopsis speciosa Species Aglajidae 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 NPC169113 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 NPC169113 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