Structure

Physi-Chem Properties

Molecular Weight:  335.14
Volume:  327.475
LogP:  2.276
LogD:  2.43
LogS:  -2.825
# Rotatable Bonds:  5
TPSA:  90.27
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.858
Synthetic Accessibility Score:  3.397
Fsp3:  0.471
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.765
MDCK Permeability:  2.3316244551097043e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.658
Plasma Protein Binding (PPB):  94.96197509765625%
Volume Distribution (VD):  0.67
Pgp-substrate:  4.445556163787842%

ADMET: Metabolism

CYP1A2-inhibitor:  0.844
CYP1A2-substrate:  0.939
CYP2C19-inhibitor:  0.091
CYP2C19-substrate:  0.839
CYP2C9-inhibitor:  0.033
CYP2C9-substrate:  0.84
CYP2D6-inhibitor:  0.189
CYP2D6-substrate:  0.571
CYP3A4-inhibitor:  0.817
CYP3A4-substrate:  0.512

ADMET: Excretion

Clearance (CL):  9.101
Half-life (T1/2):  0.325

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.054
Drug-inuced Liver Injury (DILI):  0.063
AMES Toxicity:  0.028
Rat Oral Acute Toxicity:  0.034
Maximum Recommended Daily Dose:  0.123
Skin Sensitization:  0.14
Carcinogencity:  0.877
Eye Corrosion:  0.003
Eye Irritation:  0.017
Respiratory Toxicity:  0.75

Download Data

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

  Natural Product: NPC142000

Natural Product ID:  NPC142000
Common Name*:   UEHVFWBKXUSZEQ-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  UEHVFWBKXUSZEQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C17H21NO6/c1-17(2,20)12(19)7-10-14(21-3)9-5-6-11-15(24-8-23-11)13(9)18-16(10)22-4/h5-6,12,19-20H,7-8H2,1-4H3
SMILES:  CC(C)(C(Cc1c(c2ccc3c(c2nc1OC)OCO3)OC)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   5320308
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0000056] Quinolones and derivatives

*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
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seeds n.a. DOI[10.1002/ejlt.201100207]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11746-997-0093-1]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seeds n.a. DOI[10.5219/332]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. seed n.a. PMID[10898633]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[15568765]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota roots n.a. n.a. PMID[21911291]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. PMID[22537213]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. PMID[24417583]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[24459770]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seeds n.a. n.a. PMID[26923696]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[31675225]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24492 Tamarindus indica Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seed Oil n.a. n.a. Database[FooDB]
NPO24492 Tamarindus indica Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO24492 Tamarindus indica Species Fabaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO24492 Tamarindus indica Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO24492 Tamarindus indica Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24492 Tamarindus indica Species Fabaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO23807 Trollius macropetalus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24492 Tamarindus indica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24492 Tamarindus indica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23241 Sigesbeckia orientalis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25716 Persicaria orientalis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23807 Trollius macropetalus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23807 Trollius macropetalus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24492 Tamarindus indica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25716 Persicaria orientalis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23241 Sigesbeckia orientalis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26343 Fagopyrum esculentum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25114 Linum usitatissimum Species Linaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24492 Tamarindus indica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO340 Orixa japonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23807 Trollius macropetalus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10149 Lespedeza bicolor 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 NPC142000 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 NPC142000 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