Structure

Physi-Chem Properties

Molecular Weight:  316.2
Volume:  344.632
LogP:  4.833
LogD:  4.024
LogS:  -5.085
# Rotatable Bonds:  0
TPSA:  38.83
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.286
Synthetic Accessibility Score:  4.751
Fsp3:  0.65
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.647
MDCK Permeability:  3.196291072526947e-05
Pgp-inhibitor:  0.765
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.041
20% Bioavailability (F20%):  0.939
30% Bioavailability (F30%):  0.847

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.139
Plasma Protein Binding (PPB):  95.43335723876953%
Volume Distribution (VD):  0.751
Pgp-substrate:  1.5002772808074951%

ADMET: Metabolism

CYP1A2-inhibitor:  0.062
CYP1A2-substrate:  0.105
CYP2C19-inhibitor:  0.215
CYP2C19-substrate:  0.511
CYP2C9-inhibitor:  0.299
CYP2C9-substrate:  0.083
CYP2D6-inhibitor:  0.302
CYP2D6-substrate:  0.176
CYP3A4-inhibitor:  0.589
CYP3A4-substrate:  0.317

ADMET: Excretion

Clearance (CL):  7.292
Half-life (T1/2):  0.212

ADMET: Toxicity

hERG Blockers:  0.02
Human Hepatotoxicity (H-HT):  0.257
Drug-inuced Liver Injury (DILI):  0.682
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.035
Maximum Recommended Daily Dose:  0.941
Skin Sensitization:  0.97
Carcinogencity:  0.183
Eye Corrosion:  0.931
Eye Irritation:  0.875
Respiratory Toxicity:  0.973

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  Natural Product: NPC617

Natural Product ID:  NPC617
Common Name*:   Lobophytolide
IUPAC Name:   n.a.
Synonyms:   Lobophytolide
Standard InCHIKey:  YOAADYNXXZGBQN-MKSAAGMNSA-N
Standard InCHI:  InChI=1S/C20H28O3/c1-13-6-5-7-14(2)9-11-18-20(4,23-18)12-17-16(10-8-13)15(3)19(21)22-17/h7-8,16-18H,3,5-6,9-12H2,1-2,4H3/b13-8+,14-7+/t16-,17+,18+,20+/m1/s1
SMILES:  C/C/1=CC[C@H]2[C@@H](OC(=O)C2=C)C[C@]2([C@H](CC/C(=C/CC1)/C)O2)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL465022
PubChem CID:   23425511
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]
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]
NPO15294 Magnolia salicifolia Species Magnoliaceae 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]
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]
NPO16560 Palhinhaea cernua Species Lycopodiaceae 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]
NPO15294 Magnolia salicifolia Species Magnoliaceae 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]
NPO25715 Senna siamea Species Fabaceae 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]
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]
NPO639 Formica polyctena Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO73 Pseudanabaena persicina Species Pseudanabaenaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14434 Alluaudia humbertii Species Didiereaceae 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]
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]
NPO16560 Palhinhaea cernua Species Lycopodiaceae 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]
NPO13733 Saccharopolyspora erythraea Species Pseudonocardiaceae Bacteria 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]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15674 Acanthosyris spinescens Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13417 Campanula medium Species Campanulaceae 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]
NPO9314 Gouania ulmifolia Species Gobiesocidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11365 Lecidea lithophila Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7023 Tetracera rosiflora Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15773 Ecteinascidia thurstoni Species Perophoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16206 Umbilicaria indica Species Umbilicariaceae 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]
NPO14107 Teucrium montanum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16453 Lycium cestroides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13577 Pieris formosa Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15037 Echinops spinosissimus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14909 Artemisia caerulescens Species Asteraceae 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]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota 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]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10877 Humboldtia laurifolia Species Fabaceae Eukaryota 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]
NPO11762 Agrimonia eupatoria Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13931 Selaginella uncinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15428 Cheilanthes tenuifolia Species Pteridaceae 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]
NPO16617 Paepalanthus hilairei Species Eriocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12764 Tillandsia fragrans Species Bromeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15879 Euphorbia nivulia Species Euphorbiaceae 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
NPT83 Cell Line MCF7 Homo sapiens IC50 = 2.3 ug.mL-1 PMID[491781]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 2.0 ug.mL-1 PMID[491781]
NPT81 Cell Line A549 Homo sapiens IC50 = 2.1 ug.mL-1 PMID[491781]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 6.3 ug.mL-1 PMID[491781]

☑ 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 NPC617 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
0.9733 High Similarity NPC141810
0.9231 High Similarity NPC272814
0.9125 High Similarity NPC50637
0.8974 High Similarity NPC281949
0.8974 High Similarity NPC301477
0.8974 High Similarity NPC25684
0.8947 High Similarity NPC476794
0.8947 High Similarity NPC470240
0.8816 High Similarity NPC235906
0.8795 High Similarity NPC166919
0.8795 High Similarity NPC151770
0.8784 High Similarity NPC163003
0.878 High Similarity NPC231889
0.8701 High Similarity NPC97516
0.8701 High Similarity NPC141789
0.8701 High Similarity NPC476028
0.8701 High Similarity NPC171204
0.8701 High Similarity NPC65603
0.869 High Similarity NPC475748
0.8684 High Similarity NPC226669
0.8684 High Similarity NPC193351
0.8684 High Similarity NPC155587
0.8684 High Similarity NPC138408
0.8642 High Similarity NPC115786
0.8571 High Similarity NPC4986
0.8554 High Similarity NPC475703
0.8553 High Similarity NPC140287
0.8553 High Similarity NPC476355
0.8537 High Similarity NPC38468
0.8537 High Similarity NPC319795
0.8537 High Similarity NPC50362
0.8537 High Similarity NPC255307
0.8488 Intermediate Similarity NPC212486
0.8488 Intermediate Similarity NPC228451
0.8488 Intermediate Similarity NPC125674
0.8488 Intermediate Similarity NPC475838
0.8481 Intermediate Similarity NPC270126
0.8481 Intermediate Similarity NPC470244
0.8481 Intermediate Similarity NPC470239
0.8481 Intermediate Similarity NPC182550
0.8471 Intermediate Similarity NPC329857
0.8471 Intermediate Similarity NPC469718
0.8462 Intermediate Similarity NPC187568
0.8462 Intermediate Similarity NPC41780
0.8452 Intermediate Similarity NPC224652
0.8434 Intermediate Similarity NPC150755
0.8434 Intermediate Similarity NPC475461
0.8434 Intermediate Similarity NPC107787
0.8434 Intermediate Similarity NPC305475
0.8421 Intermediate Similarity NPC58956
0.8421 Intermediate Similarity NPC295633
0.8421 Intermediate Similarity NPC269206
0.8415 Intermediate Similarity NPC114979
0.8415 Intermediate Similarity NPC159635
0.8415 Intermediate Similarity NPC191476
0.8391 Intermediate Similarity NPC473316
0.8391 Intermediate Similarity NPC473330
0.8391 Intermediate Similarity NPC140543
0.8391 Intermediate Similarity NPC474247
0.8375 Intermediate Similarity NPC281132
0.8375 Intermediate Similarity NPC302426
0.8375 Intermediate Similarity NPC276356
0.8372 Intermediate Similarity NPC20713
0.8354 Intermediate Similarity NPC267231
0.8333 Intermediate Similarity NPC266957
0.8333 Intermediate Similarity NPC123360
0.8313 Intermediate Similarity NPC78089
0.8313 Intermediate Similarity NPC165162
0.8295 Intermediate Similarity NPC14961
0.8295 Intermediate Similarity NPC270013
0.8293 Intermediate Similarity NPC131669
0.8293 Intermediate Similarity NPC474703
0.8293 Intermediate Similarity NPC473390
0.8293 Intermediate Similarity NPC250315
0.8293 Intermediate Similarity NPC53867
0.8293 Intermediate Similarity NPC475989
0.8272 Intermediate Similarity NPC471325
0.8272 Intermediate Similarity NPC79277
0.8272 Intermediate Similarity NPC475481
0.8256 Intermediate Similarity NPC62815
0.8256 Intermediate Similarity NPC469368
0.8256 Intermediate Similarity NPC312042
0.825 Intermediate Similarity NPC98557
0.825 Intermediate Similarity NPC472965
0.825 Intermediate Similarity NPC264227
0.825 Intermediate Similarity NPC63649
0.825 Intermediate Similarity NPC178277
0.825 Intermediate Similarity NPC167881
0.8235 Intermediate Similarity NPC202672
0.8235 Intermediate Similarity NPC475902
0.8228 Intermediate Similarity NPC320630
0.8228 Intermediate Similarity NPC7563
0.8228 Intermediate Similarity NPC116177
0.8228 Intermediate Similarity NPC474760
0.8202 Intermediate Similarity NPC476315
0.8202 Intermediate Similarity NPC230800
0.8202 Intermediate Similarity NPC279621
0.8193 Intermediate Similarity NPC96259
0.8193 Intermediate Similarity NPC156485
0.8193 Intermediate Similarity NPC138647
0.8193 Intermediate Similarity NPC476804
0.8193 Intermediate Similarity NPC470238
0.8193 Intermediate Similarity NPC141193
0.8182 Intermediate Similarity NPC81386
0.8182 Intermediate Similarity NPC474035
0.8182 Intermediate Similarity NPC476267
0.8182 Intermediate Similarity NPC471147
0.8171 Intermediate Similarity NPC89555
0.8171 Intermediate Similarity NPC178676
0.8171 Intermediate Similarity NPC173609
0.8171 Intermediate Similarity NPC35556
0.8171 Intermediate Similarity NPC229825
0.8161 Intermediate Similarity NPC184463
0.8161 Intermediate Similarity NPC133698
0.8158 Intermediate Similarity NPC475310
0.8148 Intermediate Similarity NPC74673
0.8148 Intermediate Similarity NPC69271
0.814 Intermediate Similarity NPC307411
0.8125 Intermediate Similarity NPC108816
0.8125 Intermediate Similarity NPC128276
0.8125 Intermediate Similarity NPC474341
0.8125 Intermediate Similarity NPC93763
0.8125 Intermediate Similarity NPC472960
0.8118 Intermediate Similarity NPC5130
0.8111 Intermediate Similarity NPC471140
0.8095 Intermediate Similarity NPC474547
0.8095 Intermediate Similarity NPC215364
0.8095 Intermediate Similarity NPC235792
0.809 Intermediate Similarity NPC471141
0.809 Intermediate Similarity NPC474947
0.809 Intermediate Similarity NPC475659
0.8072 Intermediate Similarity NPC39588
0.8072 Intermediate Similarity NPC170286
0.8072 Intermediate Similarity NPC128429
0.8072 Intermediate Similarity NPC169575
0.8072 Intermediate Similarity NPC475947
0.8072 Intermediate Similarity NPC40746
0.8072 Intermediate Similarity NPC215294
0.8072 Intermediate Similarity NPC318468
0.8068 Intermediate Similarity NPC476300
0.8068 Intermediate Similarity NPC475912
0.8052 Intermediate Similarity NPC129665
0.8049 Intermediate Similarity NPC24417
0.8049 Intermediate Similarity NPC39411
0.8049 Intermediate Similarity NPC255580
0.8049 Intermediate Similarity NPC35089
0.8049 Intermediate Similarity NPC325031
0.8049 Intermediate Similarity NPC10276
0.8046 Intermediate Similarity NPC251385
0.8046 Intermediate Similarity NPC49342
0.8046 Intermediate Similarity NPC144133
0.8046 Intermediate Similarity NPC475855
0.8046 Intermediate Similarity NPC51004
0.8046 Intermediate Similarity NPC179394
0.8025 Intermediate Similarity NPC19841
0.8023 Intermediate Similarity NPC477302
0.8022 Intermediate Similarity NPC279561
0.8 Intermediate Similarity NPC476275
0.8 Intermediate Similarity NPC57744
0.8 Intermediate Similarity NPC284902
0.8 Intermediate Similarity NPC279859
0.8 Intermediate Similarity NPC473859
0.8 Intermediate Similarity NPC38576
0.8 Intermediate Similarity NPC194871
0.7978 Intermediate Similarity NPC57405
0.7978 Intermediate Similarity NPC474338
0.7978 Intermediate Similarity NPC477131
0.7978 Intermediate Similarity NPC303942
0.7978 Intermediate Similarity NPC198853
0.7976 Intermediate Similarity NPC72464
0.7976 Intermediate Similarity NPC158756
0.7976 Intermediate Similarity NPC82297
0.7975 Intermediate Similarity NPC475861
0.7955 Intermediate Similarity NPC123177
0.7955 Intermediate Similarity NPC150978
0.7955 Intermediate Similarity NPC74103
0.7955 Intermediate Similarity NPC12172
0.7955 Intermediate Similarity NPC30515
0.7955 Intermediate Similarity NPC208886
0.7955 Intermediate Similarity NPC131209
0.7955 Intermediate Similarity NPC70595
0.7952 Intermediate Similarity NPC475936
0.7935 Intermediate Similarity NPC288876
0.7931 Intermediate Similarity NPC472872
0.7931 Intermediate Similarity NPC218927
0.7931 Intermediate Similarity NPC206001
0.7927 Intermediate Similarity NPC223904
0.7922 Intermediate Similarity NPC472955
0.7907 Intermediate Similarity NPC471739
0.7907 Intermediate Similarity NPC72513
0.7907 Intermediate Similarity NPC160138
0.7901 Intermediate Similarity NPC196653
0.7901 Intermediate Similarity NPC471465
0.7895 Intermediate Similarity NPC276290
0.7895 Intermediate Similarity NPC470256
0.7889 Intermediate Similarity NPC36954
0.7889 Intermediate Similarity NPC273197
0.7889 Intermediate Similarity NPC67584
0.7889 Intermediate Similarity NPC234339
0.7889 Intermediate Similarity NPC304886

  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 NPC617 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
0.8571 High Similarity NPD1695 Approved
0.8537 High Similarity NPD1733 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD1694 Approved
0.7444 Intermediate Similarity NPD46 Approved
0.7444 Intermediate Similarity NPD6698 Approved
0.7326 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD7838 Discovery
0.7045 Intermediate Similarity NPD7154 Phase 3
0.6932 Remote Similarity NPD5209 Approved
0.6905 Remote Similarity NPD8039 Approved
0.6893 Remote Similarity NPD6371 Approved
0.6882 Remote Similarity NPD5785 Approved
0.6818 Remote Similarity NPD5369 Approved
0.6742 Remote Similarity NPD6435 Approved
0.6735 Remote Similarity NPD4225 Approved
0.6705 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6705 Remote Similarity NPD4820 Approved
0.6705 Remote Similarity NPD4819 Approved
0.6705 Remote Similarity NPD4821 Approved
0.6705 Remote Similarity NPD4822 Approved
0.6703 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6703 Remote Similarity NPD5363 Approved
0.6667 Remote Similarity NPD6008 Approved
0.6667 Remote Similarity NPD5282 Discontinued
0.6667 Remote Similarity NPD5362 Discontinued
0.663 Remote Similarity NPD6684 Approved
0.663 Remote Similarity NPD7334 Approved
0.663 Remote Similarity NPD7146 Approved
0.663 Remote Similarity NPD6409 Approved
0.663 Remote Similarity NPD5330 Approved
0.663 Remote Similarity NPD7521 Approved
0.6562 Remote Similarity NPD6399 Phase 3
0.6556 Remote Similarity NPD4269 Approved
0.6556 Remote Similarity NPD4270 Approved
0.6517 Remote Similarity NPD5368 Approved
0.6514 Remote Similarity NPD7115 Discovery
0.6509 Remote Similarity NPD8413 Clinical (unspecified phase)
0.65 Remote Similarity NPD6648 Approved
0.6489 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6489 Remote Similarity NPD6903 Approved
0.6477 Remote Similarity NPD4271 Approved
0.6477 Remote Similarity NPD4268 Approved
0.6458 Remote Similarity NPD7983 Approved
0.6458 Remote Similarity NPD5693 Phase 1
0.6452 Remote Similarity NPD4249 Approved
0.6452 Remote Similarity NPD5786 Approved
0.6442 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6436 Remote Similarity NPD5344 Discontinued
0.6429 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6421 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6421 Remote Similarity NPD6101 Approved
0.64 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6392 Remote Similarity NPD5779 Approved
0.6392 Remote Similarity NPD5778 Approved
0.6383 Remote Similarity NPD4250 Approved
0.6383 Remote Similarity NPD4251 Approved
0.6381 Remote Similarity NPD6686 Approved
0.6354 Remote Similarity NPD5207 Approved
0.6333 Remote Similarity NPD4252 Approved
0.6327 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6327 Remote Similarity NPD6001 Approved
0.6327 Remote Similarity NPD7900 Approved
0.6316 Remote Similarity NPD5737 Approved
0.6316 Remote Similarity NPD6672 Approved
0.6296 Remote Similarity NPD6053 Discontinued
0.6292 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6289 Remote Similarity NPD6411 Approved
0.6263 Remote Similarity NPD5695 Phase 3
0.6262 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6238 Remote Similarity NPD5696 Approved
0.6211 Remote Similarity NPD3573 Approved
0.6168 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6146 Remote Similarity NPD5208 Approved
0.6145 Remote Similarity NPD7331 Phase 2
0.6139 Remote Similarity NPD7902 Approved
0.6139 Remote Similarity NPD6084 Phase 2
0.6139 Remote Similarity NPD6083 Phase 2
0.6132 Remote Similarity NPD5697 Approved
0.6129 Remote Similarity NPD5332 Approved
0.6129 Remote Similarity NPD5331 Approved
0.6105 Remote Similarity NPD6098 Approved
0.6105 Remote Similarity NPD6422 Discontinued
0.6087 Remote Similarity NPD4790 Discontinued
0.6082 Remote Similarity NPD6080 Approved
0.6082 Remote Similarity NPD6051 Approved
0.6082 Remote Similarity NPD6904 Approved
0.6082 Remote Similarity NPD6673 Approved
0.6078 Remote Similarity NPD7638 Approved
0.6075 Remote Similarity NPD6899 Approved
0.6075 Remote Similarity NPD6881 Approved
0.6064 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6055 Remote Similarity NPD6649 Approved
0.6055 Remote Similarity NPD6650 Approved
0.6055 Remote Similarity NPD2181 Clinical (unspecified phase)
0.604 Remote Similarity NPD5349 Clinical (unspecified phase)
0.604 Remote Similarity NPD7839 Suspended
0.6038 Remote Similarity NPD6402 Approved
0.6038 Remote Similarity NPD7128 Approved
0.6038 Remote Similarity NPD5739 Approved
0.6038 Remote Similarity NPD6675 Approved
0.6024 Remote Similarity NPD7341 Phase 2
0.6022 Remote Similarity NPD3667 Approved
0.602 Remote Similarity NPD5692 Phase 3
0.6019 Remote Similarity NPD7639 Approved
0.6019 Remote Similarity NPD6373 Approved
0.6019 Remote Similarity NPD7640 Approved
0.6019 Remote Similarity NPD6012 Approved
0.6019 Remote Similarity NPD6372 Approved
0.6019 Remote Similarity NPD6014 Approved
0.6019 Remote Similarity NPD6013 Approved
0.6 Remote Similarity NPD6927 Phase 3
0.6 Remote Similarity NPD29 Approved
0.6 Remote Similarity NPD4756 Discovery
0.6 Remote Similarity NPD28 Approved
0.6 Remote Similarity NPD7748 Approved
0.5981 Remote Similarity NPD5701 Approved
0.5963 Remote Similarity NPD7102 Approved
0.5963 Remote Similarity NPD2067 Discontinued
0.5963 Remote Similarity NPD7290 Approved
0.5963 Remote Similarity NPD6883 Approved
0.596 Remote Similarity NPD5284 Approved
0.596 Remote Similarity NPD5694 Approved
0.596 Remote Similarity NPD5281 Approved
0.596 Remote Similarity NPD6050 Approved
0.5952 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5938 Remote Similarity NPD3618 Phase 1
0.5926 Remote Similarity NPD7320 Approved
0.5926 Remote Similarity NPD6011 Approved
0.5918 Remote Similarity NPD5370 Suspended
0.5909 Remote Similarity NPD6617 Approved
0.5909 Remote Similarity NPD6847 Approved
0.5909 Remote Similarity NPD8130 Phase 1
0.5909 Remote Similarity NPD6869 Approved
0.5904 Remote Similarity NPD3197 Phase 1
0.5904 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5895 Remote Similarity NPD3666 Approved
0.5895 Remote Similarity NPD3668 Phase 3
0.5895 Remote Similarity NPD3133 Approved
0.5895 Remote Similarity NPD3665 Phase 1
0.5895 Remote Similarity NPD4786 Approved
0.5862 Remote Similarity NPD8515 Approved
0.5862 Remote Similarity NPD8516 Approved
0.5862 Remote Similarity NPD8517 Approved
0.5862 Remote Similarity NPD8513 Phase 3
0.5856 Remote Similarity NPD8297 Approved
0.5856 Remote Similarity NPD6882 Approved
0.5844 Remote Similarity NPD3172 Approved
0.5806 Remote Similarity NPD4695 Discontinued
0.58 Remote Similarity NPD7515 Phase 2
0.58 Remote Similarity NPD7637 Suspended
0.58 Remote Similarity NPD8034 Phase 2
0.58 Remote Similarity NPD8035 Phase 2
0.58 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5784 Remote Similarity NPD4629 Approved
0.5784 Remote Similarity NPD5210 Approved
0.5773 Remote Similarity NPD5279 Phase 3
0.5769 Remote Similarity NPD3196 Approved
0.5769 Remote Similarity NPD3195 Phase 2
0.5769 Remote Similarity NPD3194 Approved
0.5769 Remote Similarity NPD4266 Approved
0.5763 Remote Similarity NPD7642 Approved
0.5758 Remote Similarity NPD4753 Phase 2
0.5755 Remote Similarity NPD5211 Phase 2
0.5743 Remote Similarity NPD4202 Approved
0.5732 Remote Similarity NPD1145 Discontinued
0.5729 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5714 Remote Similarity NPD5285 Approved
0.5714 Remote Similarity NPD5286 Approved
0.5714 Remote Similarity NPD4696 Approved
0.5702 Remote Similarity NPD6274 Approved
0.5701 Remote Similarity NPD6052 Approved
0.5684 Remote Similarity NPD4223 Phase 3
0.5684 Remote Similarity NPD4221 Approved
0.5673 Remote Similarity NPD4755 Approved
0.5673 Remote Similarity NPD5959 Approved
0.5667 Remote Similarity NPD8273 Phase 1
0.5648 Remote Similarity NPD5141 Approved
0.5647 Remote Similarity NPD9496 Clinical (unspecified phase)
0.5644 Remote Similarity NPD6079 Approved
0.5632 Remote Similarity NPD229 Approved
0.5631 Remote Similarity NPD5654 Approved
0.563 Remote Similarity NPD7830 Approved
0.563 Remote Similarity NPD7829 Approved
0.5625 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5625 Remote Similarity NPD6695 Phase 3
0.562 Remote Similarity NPD8074 Phase 3
0.5612 Remote Similarity NPD5690 Phase 2
0.5612 Remote Similarity NPD4519 Discontinued
0.5612 Remote Similarity NPD4623 Approved
0.5612 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5607 Remote Similarity NPD5226 Approved
0.5607 Remote Similarity NPD4633 Approved
0.5607 Remote Similarity NPD5225 Approved
0.5607 Remote Similarity NPD5224 Approved
0.56 Remote Similarity NPD5343 Approved
0.56 Remote Similarity NPD5328 Approved

  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