Structure

Physi-Chem Properties

Molecular Weight:  365.26
Volume:  392.908
LogP:  5.119
LogD:  3.892
LogS:  -6.026
# Rotatable Bonds:  10
TPSA:  49.69
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.571
Synthetic Accessibility Score:  3.826
Fsp3:  0.762
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.663
MDCK Permeability:  1.7611648218007758e-05
Pgp-inhibitor:  0.951
Pgp-substrate:  0.115
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.666
Plasma Protein Binding (PPB):  96.68531799316406%
Volume Distribution (VD):  0.895
Pgp-substrate:  1.8068516254425049%

ADMET: Metabolism

CYP1A2-inhibitor:  0.388
CYP1A2-substrate:  0.974
CYP2C19-inhibitor:  0.556
CYP2C19-substrate:  0.954
CYP2C9-inhibitor:  0.463
CYP2C9-substrate:  0.8
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.702
CYP3A4-inhibitor:  0.687
CYP3A4-substrate:  0.873

ADMET: Excretion

Clearance (CL):  2.961
Half-life (T1/2):  0.2

ADMET: Toxicity

hERG Blockers:  0.083
Human Hepatotoxicity (H-HT):  0.273
Drug-inuced Liver Injury (DILI):  0.416
AMES Toxicity:  0.234
Rat Oral Acute Toxicity:  0.582
Maximum Recommended Daily Dose:  0.985
Skin Sensitization:  0.387
Carcinogencity:  0.103
Eye Corrosion:  0.003
Eye Irritation:  0.018
Respiratory Toxicity:  0.875

Download Data

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

  Natural Product: NPC472167

Natural Product ID:  NPC472167
Common Name*:   QQSYQDSEMQWNAW-DLBZAZTESA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QQSYQDSEMQWNAW-DLBZAZTESA-N
Standard InCHI:  InChI=1S/C21H35NO4/c1-6-7-8-9-10-11-12-16-13-14-17(24-3)19-18(16)20(23)21(25-4)15(2)22(19)26-5/h16-17H,6-14H2,1-5H3/t16-,17+/m0/s1
SMILES:  CCCCCCCCC1CCC(C2=C1C(=O)C(=C(N2OC)C)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3342754
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000254] Ethers
          • [CHEMONTID:0000128] Alkyl aryl ethers

*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
NPO22669 Waltheria indica Species Malvaceae Eukaryota roots n.a. n.a. PMID[25314007]
NPO22669 Waltheria indica Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[26848627]
NPO22669 Waltheria indica Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[33095014]
NPO22669 Waltheria indica Species Malvaceae 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
NPT839 Cell Line L6 Rattus norvegicus IC50 = 70.0 nM PMID[494434]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 = 45800.0 nM PMID[494434]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 > 100000.0 nM PMID[494434]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 40.0 nM PMID[494434]
NPT2 Others Unspecified Ratio IC50 = 1.8 n.a. PMID[494434]

☑ 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 NPC472167 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
0.9149 High Similarity NPC472162
0.9149 High Similarity NPC472166
0.8889 High Similarity NPC472136
0.8085 Intermediate Similarity NPC472161
0.7917 Intermediate Similarity NPC116231
0.7692 Intermediate Similarity NPC472165
0.6752 Remote Similarity NPC472164
0.6724 Remote Similarity NPC5485
0.661 Remote Similarity NPC7905
0.661 Remote Similarity NPC315652
0.6555 Remote Similarity NPC59751
0.6555 Remote Similarity NPC271621
0.6555 Remote Similarity NPC27413
0.65 Remote Similarity NPC296361
0.6476 Remote Similarity NPC280833
0.6449 Remote Similarity NPC248193
0.6415 Remote Similarity NPC113393
0.6393 Remote Similarity NPC473808
0.6381 Remote Similarity NPC307298
0.6355 Remote Similarity NPC166110
0.6341 Remote Similarity NPC315915
0.6316 Remote Similarity NPC133420
0.6311 Remote Similarity NPC474359
0.6271 Remote Similarity NPC44733
0.6226 Remote Similarity NPC143025
0.6226 Remote Similarity NPC53454
0.6214 Remote Similarity NPC8091
0.62 Remote Similarity NPC23778
0.619 Remote Similarity NPC220478
0.6168 Remote Similarity NPC142159
0.6168 Remote Similarity NPC95364
0.6154 Remote Similarity NPC60951
0.6147 Remote Similarity NPC476597
0.6147 Remote Similarity NPC476598
0.6147 Remote Similarity NPC271652
0.6139 Remote Similarity NPC475681
0.6106 Remote Similarity NPC316730
0.61 Remote Similarity NPC471225
0.61 Remote Similarity NPC283087
0.6095 Remote Similarity NPC475614
0.6091 Remote Similarity NPC476596
0.6075 Remote Similarity NPC478261
0.6075 Remote Similarity NPC478260
0.6075 Remote Similarity NPC478259
0.6068 Remote Similarity NPC176773
0.6058 Remote Similarity NPC222358
0.6058 Remote Similarity NPC288281
0.6055 Remote Similarity NPC32944
0.6055 Remote Similarity NPC193396
0.6034 Remote Similarity NPC75523
0.6034 Remote Similarity NPC87919
0.6019 Remote Similarity NPC474085
0.6 Remote Similarity NPC474619
0.5983 Remote Similarity NPC154601
0.5983 Remote Similarity NPC271269
0.5981 Remote Similarity NPC220930
0.5981 Remote Similarity NPC272039
0.598 Remote Similarity NPC471299
0.5963 Remote Similarity NPC471818
0.5962 Remote Similarity NPC10080
0.5962 Remote Similarity NPC123908
0.5957 Remote Similarity NPC98897
0.5954 Remote Similarity NPC307165
0.5943 Remote Similarity NPC133652
0.5943 Remote Similarity NPC241512
0.5943 Remote Similarity NPC8518
0.5943 Remote Similarity NPC132228
0.5943 Remote Similarity NPC90287
0.5943 Remote Similarity NPC6185
0.5943 Remote Similarity NPC263997
0.5941 Remote Similarity NPC187568
0.5941 Remote Similarity NPC41780
0.5938 Remote Similarity NPC146376
0.5938 Remote Similarity NPC125578
0.5938 Remote Similarity NPC263382
0.5932 Remote Similarity NPC251330
0.5926 Remote Similarity NPC185059
0.5926 Remote Similarity NPC475001
0.5923 Remote Similarity NPC478136
0.5918 Remote Similarity NPC474539
0.5913 Remote Similarity NPC471699
0.5913 Remote Similarity NPC77703
0.5913 Remote Similarity NPC469851
0.5909 Remote Similarity NPC190442
0.5909 Remote Similarity NPC248913
0.5905 Remote Similarity NPC193198
0.5905 Remote Similarity NPC474703
0.5897 Remote Similarity NPC472616
0.5895 Remote Similarity NPC16119
0.5893 Remote Similarity NPC470978
0.5893 Remote Similarity NPC295347
0.5893 Remote Similarity NPC470974
0.5893 Remote Similarity NPC91408
0.5888 Remote Similarity NPC203795
0.5887 Remote Similarity NPC316325
0.5882 Remote Similarity NPC471220
0.5882 Remote Similarity NPC470072
0.5882 Remote Similarity NPC315765
0.5878 Remote Similarity NPC97861
0.5877 Remote Similarity NPC270813
0.5877 Remote Similarity NPC166770
0.5876 Remote Similarity NPC94488
0.5873 Remote Similarity NPC477140
0.5873 Remote Similarity NPC477143
0.5873 Remote Similarity NPC13351
0.5872 Remote Similarity NPC284561
0.5865 Remote Similarity NPC471325
0.5862 Remote Similarity NPC80781
0.5856 Remote Similarity NPC229976
0.5851 Remote Similarity NPC474400
0.5851 Remote Similarity NPC34622
0.5847 Remote Similarity NPC185929
0.5847 Remote Similarity NPC472615
0.5846 Remote Similarity NPC96010
0.5846 Remote Similarity NPC317654
0.5833 Remote Similarity NPC218602
0.5833 Remote Similarity NPC103743
0.5833 Remote Similarity NPC243272
0.5833 Remote Similarity NPC113370
0.5833 Remote Similarity NPC215507
0.5833 Remote Similarity NPC476079
0.5826 Remote Similarity NPC215253
0.5826 Remote Similarity NPC185253
0.5825 Remote Similarity NPC276647
0.5825 Remote Similarity NPC268502
0.5825 Remote Similarity NPC254996
0.5825 Remote Similarity NPC622
0.5818 Remote Similarity NPC475823
0.5818 Remote Similarity NPC253177
0.5818 Remote Similarity NPC212679
0.5818 Remote Similarity NPC223093
0.5818 Remote Similarity NPC220454
0.5818 Remote Similarity NPC474209
0.5818 Remote Similarity NPC280592
0.5818 Remote Similarity NPC213636
0.5818 Remote Similarity NPC469595
0.5818 Remote Similarity NPC471399
0.5816 Remote Similarity NPC291062
0.5816 Remote Similarity NPC94743
0.5816 Remote Similarity NPC173321
0.5812 Remote Similarity NPC473144
0.5812 Remote Similarity NPC271059
0.5812 Remote Similarity NPC297281
0.5812 Remote Similarity NPC320154
0.5812 Remote Similarity NPC25666
0.5804 Remote Similarity NPC474882
0.5804 Remote Similarity NPC212812
0.5804 Remote Similarity NPC148463
0.58 Remote Similarity NPC264178
0.5794 Remote Similarity NPC471060
0.5794 Remote Similarity NPC2640
0.5794 Remote Similarity NPC96621
0.5794 Remote Similarity NPC189311
0.5794 Remote Similarity NPC476678
0.5789 Remote Similarity NPC134083
0.5789 Remote Similarity NPC208094
0.5789 Remote Similarity NPC241426
0.5784 Remote Similarity NPC316324
0.5784 Remote Similarity NPC473536
0.578 Remote Similarity NPC26078
0.578 Remote Similarity NPC473658
0.5778 Remote Similarity NPC239252
0.5778 Remote Similarity NPC473703
0.5776 Remote Similarity NPC472643
0.5776 Remote Similarity NPC34193
0.5776 Remote Similarity NPC314792
0.5773 Remote Similarity NPC134385
0.5766 Remote Similarity NPC471329
0.5766 Remote Similarity NPC296114
0.5766 Remote Similarity NPC473944
0.5763 Remote Similarity NPC470073
0.5755 Remote Similarity NPC470047
0.5755 Remote Similarity NPC470046
0.5752 Remote Similarity NPC150041
0.575 Remote Similarity NPC476276
0.575 Remote Similarity NPC220730
0.5748 Remote Similarity NPC11379
0.5746 Remote Similarity NPC133089
0.5745 Remote Similarity NPC57463
0.5745 Remote Similarity NPC151728
0.5743 Remote Similarity NPC244166
0.5743 Remote Similarity NPC175079
0.5741 Remote Similarity NPC472863
0.5741 Remote Similarity NPC38576
0.5741 Remote Similarity NPC186332
0.5741 Remote Similarity NPC47220
0.5741 Remote Similarity NPC279859
0.5741 Remote Similarity NPC472009
0.5741 Remote Similarity NPC261721
0.5739 Remote Similarity NPC264378
0.5728 Remote Similarity NPC478122
0.5728 Remote Similarity NPC128276
0.5728 Remote Similarity NPC475994
0.5728 Remote Similarity NPC30321
0.5728 Remote Similarity NPC231739
0.5727 Remote Similarity NPC307092
0.5727 Remote Similarity NPC210216
0.5727 Remote Similarity NPC51358
0.5726 Remote Similarity NPC251884
0.5726 Remote Similarity NPC469598

  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 NPC472167 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
0.6667 Remote Similarity NPD7299 Clinical (unspecified phase)
0.6134 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6064 Remote Similarity NPD3704 Approved
0.5952 Remote Similarity NPD7739 Clinical (unspecified phase)
0.5906 Remote Similarity NPD7623 Phase 3
0.5906 Remote Similarity NPD7624 Clinical (unspecified phase)
0.5895 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5887 Remote Similarity NPD7500 Approved
0.5772 Remote Similarity NPD1376 Discontinued
0.5746 Remote Similarity NPD6845 Suspended
0.5725 Remote Similarity NPD7746 Phase 1
0.5725 Remote Similarity NPD7747 Phase 1
0.5672 Remote Similarity NPD2101 Approved
0.5659 Remote Similarity NPD8080 Discontinued
0.5636 Remote Similarity NPD5737 Approved
0.5636 Remote Similarity NPD6672 Approved
0.5631 Remote Similarity NPD4756 Discovery
0.5619 Remote Similarity NPD4695 Discontinued

  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