Structure

Physi-Chem Properties

Molecular Weight:  330.18
Volume:  350.785
LogP:  3.35
LogD:  3.195
LogS:  -4.646
# Rotatable Bonds:  0
TPSA:  55.9
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.294
Synthetic Accessibility Score:  4.98
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.732
MDCK Permeability:  2.5420398742426187e-05
Pgp-inhibitor:  0.018
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.74
20% Bioavailability (F20%):  0.883
30% Bioavailability (F30%):  0.179

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.403
Plasma Protein Binding (PPB):  87.13988494873047%
Volume Distribution (VD):  0.974
Pgp-substrate:  3.2605249881744385%

ADMET: Metabolism

CYP1A2-inhibitor:  0.148
CYP1A2-substrate:  0.181
CYP2C19-inhibitor:  0.774
CYP2C19-substrate:  0.462
CYP2C9-inhibitor:  0.589
CYP2C9-substrate:  0.326
CYP2D6-inhibitor:  0.024
CYP2D6-substrate:  0.253
CYP3A4-inhibitor:  0.64
CYP3A4-substrate:  0.24

ADMET: Excretion

Clearance (CL):  8.549
Half-life (T1/2):  0.692

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.915
Drug-inuced Liver Injury (DILI):  0.376
AMES Toxicity:  0.65
Rat Oral Acute Toxicity:  0.411
Maximum Recommended Daily Dose:  0.961
Skin Sensitization:  0.656
Carcinogencity:  0.097
Eye Corrosion:  0.047
Eye Irritation:  0.076
Respiratory Toxicity:  0.928

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  Natural Product: NPC20713

Natural Product ID:  NPC20713
Common Name*:   Crassocolide N
IUPAC Name:   n.a.
Synonyms:   Crassocolide N
Standard InCHIKey:  ILCUERQVXPYPHC-VCQFRWONSA-N
Standard InCHI:  InChI=1S/C20H26O4/c1-12-6-5-7-13(2)10-16-15(14(3)19(22)23-16)11-18-20(4,24-18)17(21)9-8-12/h6,10,15-16,18H,3,5,7-9,11H2,1-2,4H3/b12-6+,13-10+/t15-,16-,18+,20-/m0/s1
SMILES:  C/C/1=C[C@@H]2OC(=O)C(=C)[C@@H]2C[C@H]2O[C@]2(C(=O)CC/C(=C/CC1)/C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1923744
PubChem CID:   54764414
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000147] Macrolides and analogues

*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
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[10556916]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10757709]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. formosan soft coral n.a. PMID[11141104]
NPO15773 Ecteinascidia thurstoni Species Perophoridae Eukaryota n.a. Thai n.a. PMID[12088444]
NPO10443 Sloanea zuliaensis Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. PMID[14640532]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. PMID[16872152]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[17067165]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[17125220]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. leaf n.a. PMID[17685627]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[19406895]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[19917748]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[20932054]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. Formosan soft coral n.a. PMID[22014827]
NPO25715 Senna siamea Species Fabaceae Eukaryota Stems n.a. n.a. PMID[23078294]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23513740]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25043228]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25960261]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. PMID[31994397]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[32603106]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. Antarctic n.a. PMID[8882433]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13417 Campanula medium Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13931 Selaginella uncinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20404.1 Eruca vesicaria subsp. sativa Subspecies Brassicaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13417 Campanula medium Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13931 Selaginella uncinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13577 Pieris formosa Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20404.1 Eruca vesicaria subsp. sativa Subspecies Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16206 Umbilicaria indica Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15773 Ecteinascidia thurstoni Species Perophoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14107 Teucrium montanum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO639 Formica polyctena Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13036 Culicinomyces clavisporus Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20404.1 Eruca vesicaria subsp. sativa Subspecies Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14909 Artemisia caerulescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16453 Lycium cestroides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15037 Echinops spinosissimus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6809 Cailliea cinerea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26988 Acinos thymoides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10443 Sloanea zuliaensis Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11762 Agrimonia eupatoria Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13733 Saccharopolyspora erythraea Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16534 Pterocaulon alopecuroides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26508 Uvariopsis tripetala Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15983 Udotea cyathiformis Species Udoteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5719 Hedyotis lawsoniae Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13931 Selaginella uncinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13417 Campanula medium Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15428 Cheilanthes tenuifolia Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12764 Tillandsia fragrans Species Bromeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16617 Paepalanthus hilairei Species Eriocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11365 Lecidea lithophila Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15879 Euphorbia nivulia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO73 Pseudanabaena persicina Species Pseudanabaenaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12451 Dermocybe cinnabarina Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12217 Buccinum undatum Species Buccinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16774 Hermidium alipes n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO14434 Alluaudia humbertii Species Didiereaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13577 Pieris formosa Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14591 Rhabdodendron amazonicum Species Rhabdodendraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16301 Ilex macropoda Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2584 Monostroma fuscum Species Monostromataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16740 Helipterum venustum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10877 Humboldtia laurifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25278 Cystofilobasidium infirmominiatum Species Cystofilobasidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1655 Corydendrium parasiticum Species Oceaniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15674 Acanthosyris spinescens Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5127 Cladocroce incurvata Species Chalinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13264 Alstonia lanceolifera Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7023 Tetracera rosiflora Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9314 Gouania ulmifolia Species Gobiesocidae 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
NPT91 Cell Line KB Homo sapiens IC50 = 4.7 ug.mL-1 PMID[458795]
NPT165 Cell Line HeLa Homo sapiens IC50 = 4.7 ug.mL-1 PMID[458795]
NPT1184 Cell Line Daoy Homo sapiens IC50 = 2.8 ug.mL-1 PMID[458795]

☑ 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 NPC20713 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
0.9425 High Similarity NPC469718
0.9425 High Similarity NPC329857
0.9333 High Similarity NPC476275
0.9222 High Similarity NPC474947
0.908 High Similarity NPC231889
0.9059 High Similarity NPC272814
0.8977 High Similarity NPC475902
0.8936 High Similarity NPC477511
0.8936 High Similarity NPC264477
0.8913 High Similarity NPC17585
0.8901 High Similarity NPC140543
0.8876 High Similarity NPC166919
0.8864 High Similarity NPC475703
0.8817 High Similarity NPC471140
0.8778 High Similarity NPC475748
0.8778 High Similarity NPC62815
0.875 High Similarity NPC50637
0.8737 High Similarity NPC201718
0.8737 High Similarity NPC164598
0.8737 High Similarity NPC474339
0.8696 High Similarity NPC471147
0.8696 High Similarity NPC476267
0.8667 High Similarity NPC151770
0.866 High Similarity NPC474741
0.866 High Similarity NPC471143
0.866 High Similarity NPC477510
0.8632 High Similarity NPC469551
0.8632 High Similarity NPC477512
0.8621 High Similarity NPC318468
0.8605 High Similarity NPC141810
0.8602 High Similarity NPC475659
0.8556 High Similarity NPC469653
0.8556 High Similarity NPC469631
0.8556 High Similarity NPC475906
0.8556 High Similarity NPC469628
0.8556 High Similarity NPC471047
0.8542 High Similarity NPC476270
0.8539 High Similarity NPC279859
0.8539 High Similarity NPC38576
0.8511 High Similarity NPC473859
0.8495 Intermediate Similarity NPC474035
0.8495 Intermediate Similarity NPC81386
0.8495 Intermediate Similarity NPC473316
0.8495 Intermediate Similarity NPC473330
0.8485 Intermediate Similarity NPC477513
0.8462 Intermediate Similarity NPC475971
0.8454 Intermediate Similarity NPC471148
0.8454 Intermediate Similarity NPC149371
0.8444 Intermediate Similarity NPC471739
0.8444 Intermediate Similarity NPC266957
0.8438 Intermediate Similarity NPC475949
0.8438 Intermediate Similarity NPC288876
0.8427 Intermediate Similarity NPC474547
0.8409 Intermediate Similarity NPC128429
0.8404 Intermediate Similarity NPC14961
0.8404 Intermediate Similarity NPC270013
0.8391 Intermediate Similarity NPC286229
0.8387 Intermediate Similarity NPC212486
0.8387 Intermediate Similarity NPC165383
0.8372 Intermediate Similarity NPC617
0.837 Intermediate Similarity NPC312042
0.837 Intermediate Similarity NPC51004
0.8367 Intermediate Similarity NPC475945
0.8367 Intermediate Similarity NPC475871
0.8352 Intermediate Similarity NPC202672
0.8351 Intermediate Similarity NPC474742
0.8351 Intermediate Similarity NPC47880
0.8333 Intermediate Similarity NPC208233
0.8333 Intermediate Similarity NPC284902
0.8316 Intermediate Similarity NPC476315
0.8316 Intermediate Similarity NPC299396
0.8316 Intermediate Similarity NPC301596
0.8316 Intermediate Similarity NPC35498
0.8316 Intermediate Similarity NPC230800
0.8316 Intermediate Similarity NPC172998
0.83 Intermediate Similarity NPC474716
0.828 Intermediate Similarity NPC30515
0.8265 Intermediate Similarity NPC474747
0.8261 Intermediate Similarity NPC307411
0.8261 Intermediate Similarity NPC78008
0.8222 Intermediate Similarity NPC50362
0.8222 Intermediate Similarity NPC38468
0.8222 Intermediate Similarity NPC319795
0.8211 Intermediate Similarity NPC234339
0.8211 Intermediate Similarity NPC273197
0.8202 Intermediate Similarity NPC170377
0.8202 Intermediate Similarity NPC474703
0.8191 Intermediate Similarity NPC228451
0.8191 Intermediate Similarity NPC179746
0.8191 Intermediate Similarity NPC81419
0.8191 Intermediate Similarity NPC476300
0.8191 Intermediate Similarity NPC475912
0.8191 Intermediate Similarity NPC475302
0.8191 Intermediate Similarity NPC125674
0.8191 Intermediate Similarity NPC475838
0.8182 Intermediate Similarity NPC301477
0.8182 Intermediate Similarity NPC25684
0.8182 Intermediate Similarity NPC472755
0.8182 Intermediate Similarity NPC281949
0.8172 Intermediate Similarity NPC49342
0.8172 Intermediate Similarity NPC251385
0.8163 Intermediate Similarity NPC128733
0.8163 Intermediate Similarity NPC133907
0.8163 Intermediate Similarity NPC46998
0.8163 Intermediate Similarity NPC110443
0.8163 Intermediate Similarity NPC472753
0.8163 Intermediate Similarity NPC185141
0.8161 Intermediate Similarity NPC276647
0.8161 Intermediate Similarity NPC471740
0.8161 Intermediate Similarity NPC622
0.8155 Intermediate Similarity NPC475495
0.8144 Intermediate Similarity NPC54843
0.8144 Intermediate Similarity NPC279561
0.8144 Intermediate Similarity NPC471144
0.8137 Intermediate Similarity NPC38154
0.8132 Intermediate Similarity NPC469626
0.8132 Intermediate Similarity NPC475491
0.8111 Intermediate Similarity NPC138647
0.8111 Intermediate Similarity NPC470238
0.8105 Intermediate Similarity NPC474247
0.8105 Intermediate Similarity NPC57405
0.8105 Intermediate Similarity NPC469632
0.8105 Intermediate Similarity NPC303942
0.8085 Intermediate Similarity NPC12172
0.8085 Intermediate Similarity NPC184463
0.8085 Intermediate Similarity NPC208886
0.8081 Intermediate Similarity NPC472754
0.8077 Intermediate Similarity NPC475277
0.8077 Intermediate Similarity NPC477093
0.8077 Intermediate Similarity NPC473522
0.8068 Intermediate Similarity NPC223904
0.8068 Intermediate Similarity NPC474510
0.8065 Intermediate Similarity NPC295312
0.8043 Intermediate Similarity NPC5130
0.8043 Intermediate Similarity NPC471738
0.8022 Intermediate Similarity NPC215364
0.8021 Intermediate Similarity NPC475900
0.8021 Intermediate Similarity NPC36954
0.8 Intermediate Similarity NPC475989
0.8 Intermediate Similarity NPC19239
0.8 Intermediate Similarity NPC257358
0.8 Intermediate Similarity NPC474166
0.8 Intermediate Similarity NPC475873
0.8 Intermediate Similarity NPC135776
0.8 Intermediate Similarity NPC250315
0.8 Intermediate Similarity NPC474472
0.8 Intermediate Similarity NPC170286
0.798 Intermediate Similarity NPC15993
0.7979 Intermediate Similarity NPC179394
0.7979 Intermediate Similarity NPC476004
0.7979 Intermediate Similarity NPC474761
0.7979 Intermediate Similarity NPC106510
0.7979 Intermediate Similarity NPC144133
0.7979 Intermediate Similarity NPC71533
0.7959 Intermediate Similarity NPC473326
0.7959 Intermediate Similarity NPC470188
0.7959 Intermediate Similarity NPC264378
0.7944 Intermediate Similarity NPC471146
0.7941 Intermediate Similarity NPC469558
0.7938 Intermediate Similarity NPC476009
0.7938 Intermediate Similarity NPC470883
0.7938 Intermediate Similarity NPC76862
0.7938 Intermediate Similarity NPC473291
0.7938 Intermediate Similarity NPC158416
0.7938 Intermediate Similarity NPC39859
0.7938 Intermediate Similarity NPC279621
0.7935 Intermediate Similarity NPC470242
0.7935 Intermediate Similarity NPC122502
0.7935 Intermediate Similarity NPC469676
0.7935 Intermediate Similarity NPC261721
0.7935 Intermediate Similarity NPC474045
0.7935 Intermediate Similarity NPC261253
0.7931 Intermediate Similarity NPC65603
0.7931 Intermediate Similarity NPC476794
0.7931 Intermediate Similarity NPC470240
0.7921 Intermediate Similarity NPC472756
0.7921 Intermediate Similarity NPC100487
0.7917 Intermediate Similarity NPC121825
0.7917 Intermediate Similarity NPC190294
0.79 Intermediate Similarity NPC320019
0.79 Intermediate Similarity NPC105725
0.79 Intermediate Similarity NPC197835
0.79 Intermediate Similarity NPC324017
0.79 Intermediate Similarity NPC189609
0.79 Intermediate Similarity NPC291500
0.79 Intermediate Similarity NPC303653
0.79 Intermediate Similarity NPC140591
0.7895 Intermediate Similarity NPC74103
0.7895 Intermediate Similarity NPC207641
0.7895 Intermediate Similarity NPC233437
0.7895 Intermediate Similarity NPC123177
0.7895 Intermediate Similarity NPC300312
0.7895 Intermediate Similarity NPC150978
0.7895 Intermediate Similarity NPC221282
0.7895 Intermediate Similarity NPC111114
0.7895 Intermediate Similarity NPC261607
0.7895 Intermediate Similarity NPC284185
0.7895 Intermediate Similarity NPC70595
0.7889 Intermediate Similarity NPC173609
0.7872 Intermediate Similarity NPC474951

  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 NPC20713 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
0.8222 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7872 Intermediate Similarity NPD1695 Approved
0.7596 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD46 Approved
0.7245 Intermediate Similarity NPD6698 Approved
0.7222 Intermediate Similarity NPD6371 Approved
0.72 Intermediate Similarity NPD5282 Discontinued
0.7009 Intermediate Similarity NPD6008 Approved
0.7 Intermediate Similarity NPD7983 Approved
0.6947 Remote Similarity NPD5209 Approved
0.6907 Remote Similarity NPD1694 Approved
0.69 Remote Similarity NPD5785 Approved
0.69 Remote Similarity NPD7838 Discovery
0.686 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6837 Remote Similarity NPD5786 Approved
0.6771 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6765 Remote Similarity NPD5779 Approved
0.6765 Remote Similarity NPD5778 Approved
0.6735 Remote Similarity NPD5363 Approved
0.6696 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5369 Approved
0.6598 Remote Similarity NPD4269 Approved
0.6598 Remote Similarity NPD4270 Approved
0.6505 Remote Similarity NPD5693 Phase 1
0.6491 Remote Similarity NPD6053 Discontinued
0.6449 Remote Similarity NPD4225 Approved
0.6449 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6435 Approved
0.6415 Remote Similarity NPD7839 Suspended
0.641 Remote Similarity NPD7115 Discovery
0.6392 Remote Similarity NPD4252 Approved
0.6389 Remote Similarity NPD6648 Approved
0.6387 Remote Similarity NPD6319 Approved
0.6373 Remote Similarity NPD6672 Approved
0.6373 Remote Similarity NPD5737 Approved
0.6364 Remote Similarity NPD7642 Approved
0.6364 Remote Similarity NPD7154 Phase 3
0.6339 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6339 Remote Similarity NPD5697 Approved
0.6337 Remote Similarity NPD4249 Approved
0.6333 Remote Similarity NPD8513 Phase 3
0.6333 Remote Similarity NPD8517 Approved
0.6333 Remote Similarity NPD8516 Approved
0.6333 Remote Similarity NPD8515 Approved
0.633 Remote Similarity NPD5344 Discontinued
0.6311 Remote Similarity NPD6101 Approved
0.6311 Remote Similarity NPD7492 Approved
0.6311 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6283 Remote Similarity NPD6881 Approved
0.6283 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6283 Remote Similarity NPD6011 Approved
0.6283 Remote Similarity NPD6899 Approved
0.6283 Remote Similarity NPD6686 Approved
0.6279 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6275 Remote Similarity NPD4250 Approved
0.6275 Remote Similarity NPD4251 Approved
0.6263 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6261 Remote Similarity NPD6650 Approved
0.6261 Remote Similarity NPD6649 Approved
0.626 Remote Similarity NPD6616 Approved
0.625 Remote Similarity NPD6054 Approved
0.625 Remote Similarity NPD6402 Approved
0.625 Remote Similarity NPD6675 Approved
0.625 Remote Similarity NPD7128 Approved
0.625 Remote Similarity NPD5739 Approved
0.625 Remote Similarity NPD4756 Discovery
0.6238 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6228 Remote Similarity NPD6372 Approved
0.6228 Remote Similarity NPD6013 Approved
0.6228 Remote Similarity NPD6014 Approved
0.6228 Remote Similarity NPD6012 Approved
0.6228 Remote Similarity NPD6373 Approved
0.6224 Remote Similarity NPD5368 Approved
0.6211 Remote Similarity NPD8039 Approved
0.621 Remote Similarity NPD7078 Approved
0.62 Remote Similarity NPD5362 Discontinued
0.6198 Remote Similarity NPD6015 Approved
0.6198 Remote Similarity NPD6016 Approved
0.6195 Remote Similarity NPD5701 Approved
0.619 Remote Similarity NPD6411 Approved
0.6174 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6174 Remote Similarity NPD6883 Approved
0.6174 Remote Similarity NPD7290 Approved
0.6174 Remote Similarity NPD7102 Approved
0.6168 Remote Similarity NPD5695 Phase 3
0.616 Remote Similarity NPD7736 Approved
0.6154 Remote Similarity NPD6904 Approved
0.6154 Remote Similarity NPD6673 Approved
0.6154 Remote Similarity NPD4632 Approved
0.6154 Remote Similarity NPD6080 Approved
0.6148 Remote Similarity NPD5988 Approved
0.6148 Remote Similarity NPD6370 Approved
0.6147 Remote Similarity NPD5696 Approved
0.6147 Remote Similarity NPD7638 Approved
0.6142 Remote Similarity NPD7260 Phase 2
0.614 Remote Similarity NPD7320 Approved
0.6134 Remote Similarity NPD6009 Approved
0.6132 Remote Similarity NPD6399 Phase 3
0.6121 Remote Similarity NPD6617 Approved
0.6121 Remote Similarity NPD6869 Approved
0.6121 Remote Similarity NPD6847 Approved
0.6121 Remote Similarity NPD8130 Phase 1
0.6116 Remote Similarity NPD6059 Approved
0.6098 Remote Similarity NPD7830 Approved
0.6098 Remote Similarity NPD7604 Phase 2
0.6098 Remote Similarity NPD7829 Approved
0.6095 Remote Similarity NPD5692 Phase 3
0.6091 Remote Similarity NPD7640 Approved
0.6091 Remote Similarity NPD7639 Approved
0.6087 Remote Similarity NPD4061 Clinical (unspecified phase)
0.608 Remote Similarity NPD8293 Discontinued
0.608 Remote Similarity NPD8074 Phase 3
0.6068 Remote Similarity NPD8297 Approved
0.6068 Remote Similarity NPD6882 Approved
0.6066 Remote Similarity NPD5983 Phase 2
0.6061 Remote Similarity NPD4819 Approved
0.6061 Remote Similarity NPD4822 Approved
0.6061 Remote Similarity NPD4821 Approved
0.6061 Remote Similarity NPD4820 Approved
0.6061 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6055 Remote Similarity NPD6083 Phase 2
0.6055 Remote Similarity NPD6084 Phase 2
0.604 Remote Similarity NPD6110 Phase 1
0.6038 Remote Similarity NPD6050 Approved
0.6038 Remote Similarity NPD5694 Approved
0.6034 Remote Similarity NPD2067 Discontinued
0.602 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6019 Remote Similarity NPD7334 Approved
0.6019 Remote Similarity NPD6098 Approved
0.6019 Remote Similarity NPD6409 Approved
0.6019 Remote Similarity NPD7521 Approved
0.6019 Remote Similarity NPD6684 Approved
0.6019 Remote Similarity NPD7146 Approved
0.6019 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6019 Remote Similarity NPD5330 Approved
0.6 Remote Similarity NPD5370 Suspended
0.5983 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5983 Remote Similarity NPD2204 Approved
0.5969 Remote Similarity NPD6845 Suspended
0.5968 Remote Similarity NPD8328 Phase 3
0.5962 Remote Similarity NPD3573 Approved
0.5926 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5926 Remote Similarity NPD7900 Approved
0.5917 Remote Similarity NPD6274 Approved
0.5905 Remote Similarity NPD6903 Approved
0.5905 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5897 Remote Similarity NPD4634 Approved
0.5888 Remote Similarity NPD7637 Suspended
0.5888 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5887 Remote Similarity NPD8080 Discontinued
0.5873 Remote Similarity NPD8273 Phase 1
0.5873 Remote Similarity NPD6336 Discontinued
0.5873 Remote Similarity NPD8451 Approved
0.587 Remote Similarity NPD6108 Clinical (unspecified phase)
0.587 Remote Similarity NPD7331 Phase 2
0.5868 Remote Similarity NPD6317 Approved
0.5865 Remote Similarity NPD6422 Discontinued
0.5859 Remote Similarity NPD4268 Approved
0.5859 Remote Similarity NPD4271 Approved
0.5859 Remote Similarity NPD7319 Approved
0.5841 Remote Similarity NPD5211 Phase 2
0.5827 Remote Similarity NPD8448 Approved
0.582 Remote Similarity NPD6313 Approved
0.582 Remote Similarity NPD6314 Approved
0.582 Remote Similarity NPD6335 Approved
0.5806 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5806 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5806 Remote Similarity NPD8444 Approved
0.5804 Remote Similarity NPD5286 Approved
0.5804 Remote Similarity NPD5285 Approved
0.5804 Remote Similarity NPD4696 Approved
0.5794 Remote Similarity NPD5207 Approved
0.5781 Remote Similarity NPD6033 Approved
0.578 Remote Similarity NPD6001 Approved
0.5772 Remote Similarity NPD7100 Approved
0.5772 Remote Similarity NPD7101 Approved
0.5766 Remote Similarity NPD5959 Approved
0.5766 Remote Similarity NPD7902 Approved
0.5766 Remote Similarity NPD4755 Approved
0.5761 Remote Similarity NPD7341 Phase 2
0.5752 Remote Similarity NPD5223 Approved
0.5748 Remote Similarity NPD7507 Approved
0.5743 Remote Similarity NPD4695 Discontinued
0.5739 Remote Similarity NPD5141 Approved
0.5738 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5738 Remote Similarity NPD7500 Approved
0.5728 Remote Similarity NPD5332 Approved
0.5728 Remote Similarity NPD5331 Approved
0.5727 Remote Similarity NPD5654 Approved
0.5714 Remote Similarity NPD8387 Clinical (unspecified phase)
0.5702 Remote Similarity NPD4633 Approved
0.5702 Remote Similarity NPD5224 Approved
0.5702 Remote Similarity NPD5226 Approved
0.5702 Remote Similarity NPD5225 Approved
0.5701 Remote Similarity NPD6051 Approved
0.5692 Remote Similarity NPD8392 Approved
0.5692 Remote Similarity NPD8391 Approved
0.5692 Remote Similarity NPD8390 Approved
0.5691 Remote Similarity NPD7641 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