Structure

Physi-Chem Properties

Molecular Weight:  351.24
Volume:  375.612
LogP:  3.874
LogD:  3.257
LogS:  -3.543
# Rotatable Bonds:  10
TPSA:  60.69
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.655
Synthetic Accessibility Score:  3.482
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.651
MDCK Permeability:  2.123005106113851e-05
Pgp-inhibitor:  0.388
Pgp-substrate:  0.135
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.929
30% Bioavailability (F30%):  0.077

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.682
Plasma Protein Binding (PPB):  97.22740936279297%
Volume Distribution (VD):  0.78
Pgp-substrate:  1.9253413677215576%

ADMET: Metabolism

CYP1A2-inhibitor:  0.856
CYP1A2-substrate:  0.958
CYP2C19-inhibitor:  0.833
CYP2C19-substrate:  0.908
CYP2C9-inhibitor:  0.451
CYP2C9-substrate:  0.945
CYP2D6-inhibitor:  0.102
CYP2D6-substrate:  0.536
CYP3A4-inhibitor:  0.546
CYP3A4-substrate:  0.54

ADMET: Excretion

Clearance (CL):  3.229
Half-life (T1/2):  0.663

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.126
Drug-inuced Liver Injury (DILI):  0.091
AMES Toxicity:  0.591
Rat Oral Acute Toxicity:  0.287
Maximum Recommended Daily Dose:  0.948
Skin Sensitization:  0.649
Carcinogencity:  0.205
Eye Corrosion:  0.003
Eye Irritation:  0.071
Respiratory Toxicity:  0.913

Download Data

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

  Natural Product: NPC472166

Natural Product ID:  NPC472166
Common Name*:   ZIBCTGLJAQYMCY-OAHLLOKOSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  ZIBCTGLJAQYMCY-OAHLLOKOSA-N
Standard InCHI:  InChI=1S/C20H33NO4/c1-4-5-6-7-8-9-11-15-12-10-13-16-18(15)19(23)20(24-2)17(14-22)21(16)25-3/h15,22H,4-14H2,1-3H3/t15-/m1/s1
SMILES:  CCCCCCCC[C@@H]1CCCc2c1c(=O)c(c(CO)n2OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3342753
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 = 22100.0 nM PMID[485102]
NPT165 Cell Line HeLa Homo sapiens IC50 = 26.6 ug.mL-1 PMID[485103]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 = 87900.0 nM PMID[485102]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 > 100000.0 nM PMID[485102]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 2200.0 nM PMID[485102]
NPT2 Others Unspecified Ratio IC50 = 10.1 n.a. PMID[485102]
NPT188 Organism Candida parapsilosis Candida parapsilosis MIC > 32.0 ug.mL-1 PMID[485103]
NPT20 Organism Candida albicans Candida albicans MIC = 16.0 ug.mL-1 PMID[485103]
NPT19 Organism Escherichia coli Escherichia coli MIC > 32.0 ug.mL-1 PMID[485103]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC > 32.0 ug.mL-1 PMID[485103]
NPT186 Organism Candida tropicalis Candida tropicalis MIC > 32.0 ug.mL-1 PMID[485103]
NPT187 Organism Issatchenkia orientalis Pichia kudriavzevii MIC > 32.0 ug.mL-1 PMID[485103]
NPT554 Organism Candida glabrata Candida glabrata MIC > 32.0 ug.mL-1 PMID[485103]
NPT20 Organism Candida albicans Candida albicans MIC = 32.0 ug.mL-1 PMID[485103]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 32.0 ug.mL-1 PMID[485103]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 32.0 ug.mL-1 PMID[485103]
NPT2 Others Unspecified Selectivity Index = 0.8 n.a. PMID[485103]

☑ 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 NPC472166 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 NPC472167
0.8889 High Similarity NPC472136
0.8367 Intermediate Similarity NPC472162
0.8085 Intermediate Similarity NPC472161
0.7917 Intermediate Similarity NPC116231
0.7107 Intermediate Similarity NPC472165
0.687 Remote Similarity NPC5485
0.6752 Remote Similarity NPC315652
0.6752 Remote Similarity NPC7905
0.6752 Remote Similarity NPC472164
0.6699 Remote Similarity NPC53454
0.6695 Remote Similarity NPC27413
0.6695 Remote Similarity NPC59751
0.6695 Remote Similarity NPC271621
0.6639 Remote Similarity NPC296361
0.6545 Remote Similarity NPC316730
0.6529 Remote Similarity NPC473808
0.6475 Remote Similarity NPC315915
0.6465 Remote Similarity NPC475681
0.6442 Remote Similarity NPC272039
0.6442 Remote Similarity NPC220930
0.6348 Remote Similarity NPC176773
0.6339 Remote Similarity NPC77703
0.633 Remote Similarity NPC91408
0.6316 Remote Similarity NPC472616
0.6277 Remote Similarity NPC125578
0.6277 Remote Similarity NPC146376
0.6277 Remote Similarity NPC263382
0.6263 Remote Similarity NPC473536
0.6262 Remote Similarity NPC113393
0.6262 Remote Similarity NPC471399
0.6261 Remote Similarity NPC472615
0.626 Remote Similarity NPC13351
0.625 Remote Similarity NPC90287
0.625 Remote Similarity NPC241512
0.625 Remote Similarity NPC132228
0.625 Remote Similarity NPC6185
0.625 Remote Similarity NPC8518
0.625 Remote Similarity NPC263997
0.6239 Remote Similarity NPC474882
0.6226 Remote Similarity NPC307298
0.6214 Remote Similarity NPC8091
0.6211 Remote Similarity NPC94488
0.62 Remote Similarity NPC23778
0.62 Remote Similarity NPC475994
0.62 Remote Similarity NPC231739
0.62 Remote Similarity NPC478122
0.619 Remote Similarity NPC203795
0.6174 Remote Similarity NPC470073
0.617 Remote Similarity NPC243272
0.6147 Remote Similarity NPC248193
0.6146 Remote Similarity NPC291062
0.6146 Remote Similarity NPC173321
0.6146 Remote Similarity NPC94743
0.614 Remote Similarity NPC251884
0.6139 Remote Similarity NPC281138
0.6122 Remote Similarity NPC264178
0.6121 Remote Similarity NPC185929
0.6117 Remote Similarity NPC103486
0.6111 Remote Similarity NPC474209
0.6111 Remote Similarity NPC475823
0.6111 Remote Similarity NPC265856
0.61 Remote Similarity NPC283087
0.61 Remote Similarity NPC471061
0.6095 Remote Similarity NPC255174
0.6095 Remote Similarity NPC475614
0.6087 Remote Similarity NPC318544
0.6075 Remote Similarity NPC185059
0.6075 Remote Similarity NPC143025
0.6075 Remote Similarity NPC475001
0.6071 Remote Similarity NPC208094
0.6071 Remote Similarity NPC20066
0.6068 Remote Similarity NPC251330
0.6061 Remote Similarity NPC175079
0.6058 Remote Similarity NPC477786
0.6058 Remote Similarity NPC477785
0.6058 Remote Similarity NPC477784
0.6058 Remote Similarity NPC258985
0.6055 Remote Similarity NPC166110
0.6055 Remote Similarity NPC248913
0.6053 Remote Similarity NPC34193
0.6042 Remote Similarity NPC262673
0.604 Remote Similarity NPC315765
0.604 Remote Similarity NPC30321
0.6038 Remote Similarity NPC202394
0.6038 Remote Similarity NPC229717
0.6038 Remote Similarity NPC472009
0.6019 Remote Similarity NPC51358
0.6019 Remote Similarity NPC474085
0.6019 Remote Similarity NPC280833
0.6019 Remote Similarity NPC307092
0.6017 Remote Similarity NPC140251
0.6017 Remote Similarity NPC476276
0.6017 Remote Similarity NPC307903
0.6 Remote Similarity NPC92080
0.6 Remote Similarity NPC477143
0.6 Remote Similarity NPC263582
0.6 Remote Similarity NPC271652
0.6 Remote Similarity NPC44733
0.6 Remote Similarity NPC476412
0.6 Remote Similarity NPC477140
0.6 Remote Similarity NPC474619
0.6 Remote Similarity NPC247316
0.6 Remote Similarity NPC26504
0.5983 Remote Similarity NPC271269
0.5983 Remote Similarity NPC476328
0.5983 Remote Similarity NPC154601
0.5981 Remote Similarity NPC472614
0.5981 Remote Similarity NPC103743
0.5981 Remote Similarity NPC472007
0.5981 Remote Similarity NPC471738
0.5981 Remote Similarity NPC476079
0.5981 Remote Similarity NPC113370
0.598 Remote Similarity NPC308038
0.5966 Remote Similarity NPC471400
0.5963 Remote Similarity NPC477149
0.5963 Remote Similarity NPC473056
0.5963 Remote Similarity NPC477147
0.596 Remote Similarity NPC147438
0.5957 Remote Similarity NPC98897
0.5948 Remote Similarity NPC474563
0.5948 Remote Similarity NPC320154
0.5946 Remote Similarity NPC212812
0.5943 Remote Similarity NPC133652
0.5943 Remote Similarity NPC474680
0.5943 Remote Similarity NPC32037
0.5943 Remote Similarity NPC242233
0.5941 Remote Similarity NPC316324
0.594 Remote Similarity NPC313348
0.594 Remote Similarity NPC475987
0.5938 Remote Similarity NPC45264
0.5929 Remote Similarity NPC478233
0.5929 Remote Similarity NPC471916
0.5929 Remote Similarity NPC471694
0.5926 Remote Similarity NPC230387
0.5926 Remote Similarity NPC26078
0.5926 Remote Similarity NPC472008
0.5926 Remote Similarity NPC473658
0.5922 Remote Similarity NPC2482
0.5918 Remote Similarity NPC474539
0.5917 Remote Similarity NPC476290
0.5915 Remote Similarity NPC246412
0.5913 Remote Similarity NPC469851
0.5909 Remote Similarity NPC73457
0.5905 Remote Similarity NPC471595
0.5905 Remote Similarity NPC110150
0.5905 Remote Similarity NPC297398
0.5905 Remote Similarity NPC66764
0.5897 Remote Similarity NPC133420
0.5897 Remote Similarity NPC87919
0.5897 Remote Similarity NPC475239
0.5895 Remote Similarity NPC16119
0.5893 Remote Similarity NPC295347
0.5893 Remote Similarity NPC279313
0.5893 Remote Similarity NPC477438
0.5893 Remote Similarity NPC477437
0.5888 Remote Similarity NPC472974
0.5888 Remote Similarity NPC322159
0.5887 Remote Similarity NPC316325
0.5882 Remote Similarity NPC220730
0.5882 Remote Similarity NPC24596
0.5882 Remote Similarity NPC470072
0.5882 Remote Similarity NPC62336
0.5877 Remote Similarity NPC166770
0.5872 Remote Similarity NPC142159
0.5872 Remote Similarity NPC214387
0.5872 Remote Similarity NPC474918
0.5872 Remote Similarity NPC123912
0.5872 Remote Similarity NPC95364
0.5872 Remote Similarity NPC472983
0.5865 Remote Similarity NPC55869
0.5865 Remote Similarity NPC470298
0.5865 Remote Similarity NPC99308
0.5865 Remote Similarity NPC101012
0.5865 Remote Similarity NPC275766
0.5862 Remote Similarity NPC119601
0.5862 Remote Similarity NPC469598
0.5862 Remote Similarity NPC308726
0.5856 Remote Similarity NPC477435
0.5856 Remote Similarity NPC477436
0.5856 Remote Similarity NPC211230
0.5851 Remote Similarity NPC474400
0.5851 Remote Similarity NPC7029
0.5851 Remote Similarity NPC34622
0.5849 Remote Similarity NPC31086
0.5849 Remote Similarity NPC474359
0.5847 Remote Similarity NPC469852
0.5846 Remote Similarity NPC473249
0.5842 Remote Similarity NPC470525
0.5841 Remote Similarity NPC328371
0.5833 Remote Similarity NPC287079
0.5826 Remote Similarity NPC327431
0.5826 Remote Similarity NPC185253
0.5826 Remote Similarity NPC215253
0.5825 Remote Similarity NPC192329
0.5825 Remote Similarity NPC19900
0.582 Remote Similarity NPC476269
0.5818 Remote Similarity NPC236322
0.5818 Remote Similarity NPC48010
0.5818 Remote Similarity NPC223093

  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 NPC472166 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)
0.6593 Remote Similarity NPD3704 Approved
0.6271 Remote Similarity NPD7116 Clinical (unspecified phase)
0.61 Remote Similarity NPD4756 Discovery
0.6032 Remote Similarity NPD7623 Phase 3
0.6032 Remote Similarity NPD7624 Clinical (unspecified phase)
0.5952 Remote Similarity NPD7739 Clinical (unspecified phase)
0.5922 Remote Similarity NPD4695 Discontinued
0.5906 Remote Similarity NPD8080 Discontinued
0.5905 Remote Similarity NPD6110 Phase 1
0.5902 Remote Similarity NPD1376 Discontinued
0.5895 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5887 Remote Similarity NPD7500 Approved
0.5846 Remote Similarity NPD7746 Phase 1
0.5846 Remote Similarity NPD7747 Phase 1
0.5827 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5789 Remote Similarity NPD2101 Approved
0.5789 Remote Similarity NPD7341 Phase 2
0.5781 Remote Similarity NPD2838 Clinical (unspecified phase)
0.5769 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5755 Remote Similarity NPD7154 Phase 3
0.5745 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5728 Remote Similarity NPD3617 Approved
0.5652 Remote Similarity NPD6084 Phase 2
0.5652 Remote Similarity NPD6083 Phase 2
0.5636 Remote Similarity NPD5737 Approved
0.5636 Remote Similarity NPD6672 Approved
0.563 Remote Similarity NPD6845 Suspended

  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