Structure

Physi-Chem Properties

Molecular Weight:  139.06
Volume:  135.82
LogP:  0.311
LogD:  0.607
LogS:  -1.267
# Rotatable Bonds:  0
TPSA:  38.66
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.487
Synthetic Accessibility Score:  4.312
Fsp3:  0.714
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:  -4.655
MDCK Permeability:  2.0326051526353694e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.013
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.949
Plasma Protein Binding (PPB):  22.60503387451172%
Volume Distribution (VD):  0.799
Pgp-substrate:  72.97066497802734%

ADMET: Metabolism

CYP1A2-inhibitor:  0.064
CYP1A2-substrate:  0.24
CYP2C19-inhibitor:  0.034
CYP2C19-substrate:  0.46
CYP2C9-inhibitor:  0.017
CYP2C9-substrate:  0.076
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.384
CYP3A4-inhibitor:  0.005
CYP3A4-substrate:  0.219

ADMET: Excretion

Clearance (CL):  6.718
Half-life (T1/2):  0.466

ADMET: Toxicity

hERG Blockers:  0.026
Human Hepatotoxicity (H-HT):  0.08
Drug-inuced Liver Injury (DILI):  0.359
AMES Toxicity:  0.707
Rat Oral Acute Toxicity:  0.58
Maximum Recommended Daily Dose:  0.316
Skin Sensitization:  0.903
Carcinogencity:  0.843
Eye Corrosion:  0.703
Eye Irritation:  0.984
Respiratory Toxicity:  0.843

Download Data

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

  Natural Product: NPC131789

Natural Product ID:  NPC131789
Common Name*:   FMRTWLQPHKKGQW-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  FMRTWLQPHKKGQW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H9NO2/c9-6-2-1-5-3-10-4-8-7(5)6/h8H,1-4H2
SMILES:  C1CC(=O)C2=C1COCN2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   5316289
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones

*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
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10654410]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[10843587]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[15568770]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16392664]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota roots Hualien Hsien, Taiwan 2003-JUL PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[17951038]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18175961]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23022271]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24295087]
NPO20471 Sophora alopecuroides Species Fabaceae Eukaryota root bark Mongolian n.a. PMID[26073007]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[27575476]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[30298740]
NPO20471 Sophora alopecuroides Species Fabaceae Eukaryota Aerial Parts n.a. n.a. PMID[31747283]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[9868163]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. Database[Article]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19576 Thermopsis alternifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16775 Thermopsis lanceolata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26916 Thermopsis alpina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28397 Wisteria sinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20471 Sophora alopecuroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27828 Thermopsis chinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28397 Wisteria sinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26916 Thermopsis alpina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16775 Thermopsis lanceolata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19576 Thermopsis alternifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8732 Thermopsis fabacea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27828 Thermopsis chinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20471 Sophora alopecuroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5986.3 Ziziphus jujuba mill. var. inermis (bge.) rehd. Varieties Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27828 Thermopsis chinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26916 Thermopsis alpina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28397 Wisteria sinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20471 Sophora alopecuroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19576 Thermopsis alternifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16775 Thermopsis lanceolata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20471 Sophora alopecuroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8732 Thermopsis fabacea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28397 Wisteria sinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27828 Thermopsis chinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26916 Thermopsis alpina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16775 Thermopsis lanceolata Species Fabaceae 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 NPC131789 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 NPC131789 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