Structure

Physi-Chem Properties

Molecular Weight:  302.22
Volume:  338.478
LogP:  5.385
LogD:  4.16
LogS:  -5.465
# Rotatable Bonds:  0
TPSA:  21.76
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.458
Synthetic Accessibility Score:  4.891
Fsp3:  0.7
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:  -4.653
MDCK Permeability:  2.6111794795724563e-05
Pgp-inhibitor:  0.929
Pgp-substrate:  0.012
Human Intestinal Absorption (HIA):  0.047
20% Bioavailability (F20%):  0.417
30% Bioavailability (F30%):  0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.093
Plasma Protein Binding (PPB):  95.11861419677734%
Volume Distribution (VD):  1.791
Pgp-substrate:  2.0265495777130127%

ADMET: Metabolism

CYP1A2-inhibitor:  0.088
CYP1A2-substrate:  0.153
CYP2C19-inhibitor:  0.23
CYP2C19-substrate:  0.806
CYP2C9-inhibitor:  0.204
CYP2C9-substrate:  0.065
CYP2D6-inhibitor:  0.046
CYP2D6-substrate:  0.331
CYP3A4-inhibitor:  0.382
CYP3A4-substrate:  0.274

ADMET: Excretion

Clearance (CL):  5.481
Half-life (T1/2):  0.116

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.736
Drug-inuced Liver Injury (DILI):  0.713
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.026
Maximum Recommended Daily Dose:  0.908
Skin Sensitization:  0.906
Carcinogencity:  0.023
Eye Corrosion:  0.075
Eye Irritation:  0.332
Respiratory Toxicity:  0.095

Download Data

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  Natural Product: NPC83838

Natural Product ID:  NPC83838
Common Name*:   OQGXDKRHMBRZCS-PWFXJFPMSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  OQGXDKRHMBRZCS-PWFXJFPMSA-N
Standard InCHI:  InChI=1S/C20H30O2/c1-14-6-5-11-20(4)19(22-20)10-8-15(2)12-18-17(9-7-14)16(3)13-21-18/h6,12,18-19H,5,7-11,13H2,1-4H3/b14-6+,15-12+/t18-,19-,20+/m1/s1
SMILES:  C/C/1=CCC[C@@]2(C)[C@@H](CC/C(=C/[C@@H]3C(=C(C)CO3)CC1)/C)O2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1761950
PubChem CID:   54585297
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001983] Dihydrofurans

*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]
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]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26304 Hymenocallis littoralis Species Amaryllidaceae 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]
NPO26304 Hymenocallis littoralis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13931 Selaginella uncinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13417 Campanula medium Species Campanulaceae 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]
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]
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[TCM_Taiwan]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15428 Cheilanthes tenuifolia Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29 Laburnum alpinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2783 Lobophytum sarcophytoides Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16301 Ilex macropoda Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13733 Saccharopolyspora erythraea Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14434 Alluaudia humbertii Species Didiereaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4638 Cynoglossum gansuense Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16740 Helipterum venustum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13417 Campanula medium Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14591 Rhabdodendron amazonicum Species Rhabdodendraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1860 Ceratium reticulatum Species Ceratiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1655 Corydendrium parasiticum Species Oceaniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5562 Armillaria novae-zelandiae Species Physalacriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15674 Acanthosyris spinescens Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2584 Monostroma fuscum Species Monostromataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13264 Alstonia lanceolifera Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11365 Lecidea lithophila Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9314 Gouania ulmifolia Species Gobiesocidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25278 Cystofilobasidium infirmominiatum Species Cystofilobasidiaceae 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]
NPO5127 Cladocroce incurvata Species Chalinidae 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]
NPO14107 Teucrium montanum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13577 Pieris formosa Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16453 Lycium cestroides Species Solanaceae 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]
NPO6809 Cailliea cinerea n.a. n.a. n.a. 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]
NPO26304 Hymenocallis littoralis Species Amaryllidaceae Eukaryota 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]
NPO26508 Uvariopsis tripetala Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10877 Humboldtia laurifolia Species Fabaceae 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]
NPO15983 Udotea cyathiformis Species Udoteaceae 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]
NPO12764 Tillandsia fragrans Species Bromeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5719 Hedyotis lawsoniae Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6518 Aspilia laevissima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13931 Selaginella uncinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15879 Euphorbia nivulia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO943 Carex nigra Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16617 Paepalanthus hilairei Species Eriocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO73 Pseudanabaena persicina Species Pseudanabaenaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12217 Buccinum undatum Species Buccinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16534 Pterocaulon alopecuroides Species Asteraceae 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]
NPO12451 Dermocybe cinnabarina Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO639 Formica polyctena Species Formicidae 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
NPT3973 Individual Protein Endothelial PAS domain-containing protein 1 Homo sapiens EC50 = 183300.0 nM PMID[517946]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 291200.0 nM PMID[517946]

☑ 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 NPC83838 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
1.0 High Similarity NPC143810
0.9138 High Similarity NPC127824
0.873 High Similarity NPC276290
0.8276 Intermediate Similarity NPC223604
0.8226 Intermediate Similarity NPC217940
0.8182 Intermediate Similarity NPC129630
0.803 Intermediate Similarity NPC269841
0.8 Intermediate Similarity NPC472266
0.7931 Intermediate Similarity NPC165755
0.7794 Intermediate Similarity NPC477084
0.7727 Intermediate Similarity NPC259299
0.7612 Intermediate Similarity NPC305698
0.7576 Intermediate Similarity NPC327815
0.7571 Intermediate Similarity NPC471525
0.7538 Intermediate Similarity NPC140233
0.7538 Intermediate Similarity NPC287744
0.75 Intermediate Similarity NPC329989
0.75 Intermediate Similarity NPC239373
0.75 Intermediate Similarity NPC232812
0.7397 Intermediate Similarity NPC474005
0.7391 Intermediate Similarity NPC37929
0.7391 Intermediate Similarity NPC64234
0.7361 Intermediate Similarity NPC271070
0.7361 Intermediate Similarity NPC301525
0.7344 Intermediate Similarity NPC469694
0.7324 Intermediate Similarity NPC474758
0.726 Intermediate Similarity NPC84360
0.726 Intermediate Similarity NPC471454
0.7258 Intermediate Similarity NPC96663
0.7246 Intermediate Similarity NPC101622
0.7246 Intermediate Similarity NPC265574
0.7246 Intermediate Similarity NPC472947
0.7246 Intermediate Similarity NPC74722
0.7246 Intermediate Similarity NPC304690
0.7231 Intermediate Similarity NPC228574
0.7231 Intermediate Similarity NPC294304
0.7222 Intermediate Similarity NPC329852
0.7188 Intermediate Similarity NPC122239
0.7188 Intermediate Similarity NPC475931
0.7183 Intermediate Similarity NPC222244
0.7183 Intermediate Similarity NPC16349
0.7183 Intermediate Similarity NPC329763
0.7162 Intermediate Similarity NPC474341
0.7162 Intermediate Similarity NPC477089
0.7143 Intermediate Similarity NPC469660
0.7143 Intermediate Similarity NPC4299
0.7105 Intermediate Similarity NPC141810
0.7105 Intermediate Similarity NPC246621
0.7101 Intermediate Similarity NPC476945
0.7101 Intermediate Similarity NPC272961
0.7083 Intermediate Similarity NPC117746
0.7083 Intermediate Similarity NPC294434
0.7083 Intermediate Similarity NPC15499
0.7083 Intermediate Similarity NPC259599
0.7077 Intermediate Similarity NPC19241
0.7067 Intermediate Similarity NPC471537
0.7067 Intermediate Similarity NPC617
0.7059 Intermediate Similarity NPC191233
0.7042 Intermediate Similarity NPC472254
0.7031 Intermediate Similarity NPC23418
0.7027 Intermediate Similarity NPC476439
0.7027 Intermediate Similarity NPC476703
0.7015 Intermediate Similarity NPC34883
0.7 Intermediate Similarity NPC477449
0.7 Intermediate Similarity NPC261398
0.7 Intermediate Similarity NPC477448
0.7 Intermediate Similarity NPC329656
0.6974 Remote Similarity NPC474739
0.6957 Remote Similarity NPC474477
0.6944 Remote Similarity NPC476709
0.6944 Remote Similarity NPC92909
0.6944 Remote Similarity NPC107783
0.6933 Remote Similarity NPC128276
0.6912 Remote Similarity NPC308844
0.6912 Remote Similarity NPC470688
0.6912 Remote Similarity NPC220766
0.6901 Remote Similarity NPC475310
0.6892 Remote Similarity NPC256720
0.6892 Remote Similarity NPC476317
0.6892 Remote Similarity NPC236228
0.6885 Remote Similarity NPC40417
0.6885 Remote Similarity NPC294358
0.6883 Remote Similarity NPC474894
0.6883 Remote Similarity NPC79277
0.6883 Remote Similarity NPC475481
0.6866 Remote Similarity NPC283247
0.6857 Remote Similarity NPC224532
0.6857 Remote Similarity NPC310210
0.6857 Remote Similarity NPC218477
0.6849 Remote Similarity NPC144995
0.6849 Remote Similarity NPC227814
0.6849 Remote Similarity NPC469691
0.6849 Remote Similarity NPC167049
0.6849 Remote Similarity NPC470686
0.6849 Remote Similarity NPC190859
0.6842 Remote Similarity NPC325869
0.6842 Remote Similarity NPC476701
0.6825 Remote Similarity NPC227135
0.6825 Remote Similarity NPC281590
0.6818 Remote Similarity NPC154908
0.6818 Remote Similarity NPC252851
0.6818 Remote Similarity NPC226872
0.6818 Remote Similarity NPC240506
0.6818 Remote Similarity NPC158368
0.6812 Remote Similarity NPC248125
0.6812 Remote Similarity NPC116013
0.6806 Remote Similarity NPC129665
0.6806 Remote Similarity NPC257618
0.6806 Remote Similarity NPC163003
0.68 Remote Similarity NPC471225
0.68 Remote Similarity NPC262747
0.68 Remote Similarity NPC57744
0.6795 Remote Similarity NPC35556
0.6795 Remote Similarity NPC475936
0.679 Remote Similarity NPC475703
0.6769 Remote Similarity NPC226848
0.6769 Remote Similarity NPC181872
0.6769 Remote Similarity NPC155025
0.6765 Remote Similarity NPC300593
0.6761 Remote Similarity NPC16964
0.6761 Remote Similarity NPC470693
0.6761 Remote Similarity NPC107130
0.6757 Remote Similarity NPC469669
0.6757 Remote Similarity NPC469678
0.6757 Remote Similarity NPC475771
0.6721 Remote Similarity NPC474495
0.6721 Remote Similarity NPC473672
0.6719 Remote Similarity NPC210316
0.6716 Remote Similarity NPC68679
0.6716 Remote Similarity NPC475251
0.6716 Remote Similarity NPC321867
0.6716 Remote Similarity NPC207007
0.6714 Remote Similarity NPC194871
0.6712 Remote Similarity NPC476489
0.6712 Remote Similarity NPC477085
0.6712 Remote Similarity NPC476490
0.6711 Remote Similarity NPC299235
0.6711 Remote Similarity NPC209135
0.6711 Remote Similarity NPC184737
0.6711 Remote Similarity NPC23187
0.6711 Remote Similarity NPC471220
0.6711 Remote Similarity NPC253749
0.6711 Remote Similarity NPC474816
0.6709 Remote Similarity NPC475842
0.6709 Remote Similarity NPC475989
0.6709 Remote Similarity NPC53867
0.6709 Remote Similarity NPC170377
0.6709 Remote Similarity NPC474809
0.6709 Remote Similarity NPC231601
0.6709 Remote Similarity NPC272814
0.6707 Remote Similarity NPC93411
0.6667 Remote Similarity NPC170148
0.6667 Remote Similarity NPC137253
0.6667 Remote Similarity NPC471661
0.6667 Remote Similarity NPC235906
0.6667 Remote Similarity NPC123360
0.6667 Remote Similarity NPC268111
0.6667 Remote Similarity NPC261253
0.6667 Remote Similarity NPC474045
0.6667 Remote Similarity NPC27205
0.6667 Remote Similarity NPC286189
0.6667 Remote Similarity NPC325031
0.6667 Remote Similarity NPC226242
0.6667 Remote Similarity NPC475944
0.6667 Remote Similarity NPC474267
0.6667 Remote Similarity NPC204048
0.6667 Remote Similarity NPC471325
0.6667 Remote Similarity NPC50637
0.6667 Remote Similarity NPC19569
0.6667 Remote Similarity NPC69462
0.6667 Remote Similarity NPC182794
0.6667 Remote Similarity NPC469880
0.6625 Remote Similarity NPC186155
0.6625 Remote Similarity NPC160517
0.6625 Remote Similarity NPC82297
0.6625 Remote Similarity NPC78673
0.6623 Remote Similarity NPC233295
0.6623 Remote Similarity NPC178277
0.6623 Remote Similarity NPC471299
0.6622 Remote Similarity NPC140287
0.6622 Remote Similarity NPC476355
0.6622 Remote Similarity NPC474551
0.6622 Remote Similarity NPC477204
0.662 Remote Similarity NPC474823
0.662 Remote Similarity NPC470256
0.6618 Remote Similarity NPC44343
0.6618 Remote Similarity NPC179087
0.6618 Remote Similarity NPC473508
0.6618 Remote Similarity NPC210303
0.6615 Remote Similarity NPC65786
0.6615 Remote Similarity NPC27853
0.6615 Remote Similarity NPC7491
0.6615 Remote Similarity NPC101285
0.6615 Remote Similarity NPC52012
0.6615 Remote Similarity NPC13789
0.6585 Remote Similarity NPC471657
0.6585 Remote Similarity NPC45957
0.6585 Remote Similarity NPC231889
0.6582 Remote Similarity NPC471298
0.6582 Remote Similarity NPC471218

  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 NPC83838 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
0.8548 High Similarity NPD2685 Clinical (unspecified phase)
0.6716 Remote Similarity NPD368 Approved
0.6522 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6375 Remote Similarity NPD5209 Approved
0.6341 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6316 Remote Similarity NPD8039 Approved
0.622 Remote Similarity NPD6400 Clinical (unspecified phase)
0.619 Remote Similarity NPD6927 Phase 3
0.6173 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6145 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6129 Remote Similarity NPD9410 Clinical (unspecified phase)
0.6087 Remote Similarity NPD1145 Discontinued
0.6076 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6061 Remote Similarity NPD342 Phase 1
0.6047 Remote Similarity NPD6051 Approved
0.6047 Remote Similarity NPD1695 Approved
0.5977 Remote Similarity NPD7838 Discovery
0.5977 Remote Similarity NPD46 Approved
0.5977 Remote Similarity NPD6698 Approved
0.5974 Remote Similarity NPD6926 Approved
0.5974 Remote Similarity NPD6924 Approved
0.597 Remote Similarity NPD4219 Approved
0.5926 Remote Similarity NPD7332 Phase 2
0.5926 Remote Similarity NPD7514 Phase 3
0.5904 Remote Similarity NPD6695 Phase 3
0.5904 Remote Similarity NPD7154 Phase 3
0.5902 Remote Similarity NPD4265 Approved
0.5897 Remote Similarity NPD8264 Approved
0.589 Remote Similarity NPD616 Clinical (unspecified phase)
0.5867 Remote Similarity NPD6923 Approved
0.5867 Remote Similarity NPD6922 Approved
0.5854 Remote Similarity NPD6902 Approved
0.5844 Remote Similarity NPD4732 Discontinued
0.5833 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5823 Remote Similarity NPD6933 Approved
0.5797 Remote Similarity NPD585 Clinical (unspecified phase)
0.5789 Remote Similarity NPD7143 Approved
0.5789 Remote Similarity NPD7144 Approved
0.5781 Remote Similarity NPD2268 Discontinued
0.5765 Remote Similarity NPD1694 Approved
0.575 Remote Similarity NPD6925 Approved
0.575 Remote Similarity NPD6932 Approved
0.575 Remote Similarity NPD5776 Phase 2
0.5732 Remote Similarity NPD4819 Approved
0.5732 Remote Similarity NPD4820 Approved
0.5732 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5732 Remote Similarity NPD6931 Approved
0.5732 Remote Similarity NPD6930 Phase 2
0.5732 Remote Similarity NPD4821 Approved
0.5732 Remote Similarity NPD4822 Approved
0.5714 Remote Similarity NPD5362 Discontinued
0.5714 Remote Similarity NPD7151 Approved
0.5714 Remote Similarity NPD7150 Approved
0.5714 Remote Similarity NPD7152 Approved
0.5679 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5679 Remote Similarity NPD7145 Approved
0.5676 Remote Similarity NPD7331 Phase 2
0.5663 Remote Similarity NPD6898 Phase 1
0.5638 Remote Similarity NPD6648 Approved
0.5632 Remote Similarity NPD7524 Approved
0.5632 Remote Similarity NPD7750 Discontinued
0.5625 Remote Similarity NPD3701 Clinical (unspecified phase)
0.561 Remote Similarity NPD6929 Approved
0.561 Remote Similarity NPD6683 Phase 2

  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