Structure

Physi-Chem Properties

Molecular Weight:  216.08
Volume:  226.843
LogP:  3.247
LogD:  2.385
LogS:  -3.244
# Rotatable Bonds:  1
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.72
Synthetic Accessibility Score:  2.25
Fsp3:  0.154
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:  -4.813
MDCK Permeability:  1.55555535457097e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.067
30% Bioavailability (F30%):  0.274

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.12
Plasma Protein Binding (PPB):  97.8311538696289%
Volume Distribution (VD):  0.467
Pgp-substrate:  1.7644871473312378%

ADMET: Metabolism

CYP1A2-inhibitor:  0.984
CYP1A2-substrate:  0.846
CYP2C19-inhibitor:  0.516
CYP2C19-substrate:  0.089
CYP2C9-inhibitor:  0.644
CYP2C9-substrate:  0.796
CYP2D6-inhibitor:  0.716
CYP2D6-substrate:  0.448
CYP3A4-inhibitor:  0.427
CYP3A4-substrate:  0.183

ADMET: Excretion

Clearance (CL):  6.049
Half-life (T1/2):  0.739

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.038
Drug-inuced Liver Injury (DILI):  0.823
AMES Toxicity:  0.61
Rat Oral Acute Toxicity:  0.288
Maximum Recommended Daily Dose:  0.677
Skin Sensitization:  0.9
Carcinogencity:  0.803
Eye Corrosion:  0.079
Eye Irritation:  0.982
Respiratory Toxicity:  0.882

Download Data

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

  Natural Product: NPC160499

Natural Product ID:  NPC160499
Common Name*:   Nepodin
IUPAC Name:   1-(1,8-dihydroxy-3-methylnaphthalen-2-yl)ethanone
Synonyms:   Nepodin
Standard InCHIKey:  DMLHPCALHMPJHS-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H12O3/c1-7-6-9-4-3-5-10(15)12(9)13(16)11(7)8(2)14/h3-6,15-16H,1-2H3
SMILES:  Cc1cc2cccc(c2c(c1C(=O)C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL508681
PubChem CID:   100780
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0002441] Naphthols and derivatives

*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
NPO5532 Staurocucumis liouvillei Species Cucumariidae Eukaryota n.a. n.a. n.a. PMID[11421733]
NPO4573 Mortierella alpina Species Mortierellaceae Eukaryota n.a. n.a. n.a. PMID[12191843]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota Roots n.a. n.a. PMID[14510592]
NPO23148 Ludwigia octovalvis Species Onagraceae Eukaryota n.a. n.a. n.a. PMID[14738395]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[3572418]
NPO4057 Picrolemma pseudocoffea Species n.a. n.a. n.a. n.a. n.a. PMID[6533270]
NPO15237 Cyclamen mirabile Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[9090874]
NPO4573 Mortierella alpina Species Mortierellaceae Eukaryota n.a. n.a. n.a. PMID[9668087]
NPO13418 Rumex acetosa Species Polygonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13418 Rumex acetosa Species Polygonaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO13418 Rumex acetosa Species Polygonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25037 Nepeta cataria Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23235 Zanthoxylum arnottianum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15050 Rumex obtusifolius Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13107 Rumex patientia Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO574 Rumex nepalensis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13418 Rumex acetosa Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24601 Rumex dentatus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30631 Rhamnus frangula Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21718 Ligularia clivorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20960 Anchistea virginica Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15050 Rumex obtusifolius Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21718 Ligularia clivorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13107 Rumex patientia Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23148 Ludwigia octovalvis Species Onagraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24601 Rumex dentatus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23235 Zanthoxylum arnottianum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO574 Rumex nepalensis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5990 Frangula alnus Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25037 Nepeta cataria Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13418 Rumex acetosa Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25037 Nepeta cataria Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO574 Rumex nepalensis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30631 Rhamnus frangula Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24601 Rumex dentatus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15050 Rumex obtusifolius Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13107 Rumex patientia Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15237 Cyclamen mirabile Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25037 Nepeta cataria Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13418 Rumex acetosa Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5755 Bauhinia glauca Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5532 Staurocucumis liouvillei Species Cucumariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20186 Xanthomonas campestris Species Xanthomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15050 Rumex obtusifolius Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO145 Chondropetalum andreaeanum Species Restionaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13107 Rumex patientia Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6176 Ramichloridium apiculatum Species Dissoconiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4057 Picrolemma pseudocoffea Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO324 Dianella nigra Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24601 Rumex dentatus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22656 Dineutus assimilis Species Gyrinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21514 Glandularia x hybrida Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO574 Rumex nepalensis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22261 Primula rosea Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23235 Zanthoxylum arnottianum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21887 Artemisia hugueti Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20960 Anchistea virginica Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19239 Rumex palustris Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23148 Ludwigia octovalvis Species Onagraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21718 Ligularia clivorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5990 Frangula alnus Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4573 Mortierella alpina Species Mortierellaceae 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
NPT81 Cell Line A549 Homo sapiens ED50 = 31.0 ug ml-1 PMID[544022]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 36.7 ug ml-1 PMID[544022]
NPT325 Individual Protein Cyclooxygenase-2 Ovis aries Inhibition = 59.42 % PMID[544025]
NPT324 Individual Protein Cyclooxygenase-1 Ovis aries IC50 = 27430.0 nM PMID[544025]
NPT325 Individual Protein Cyclooxygenase-2 Ovis aries IC50 = 32280.0 nM PMID[544025]
NPT324 Individual Protein Cyclooxygenase-1 Ovis aries Inhibition = 68.24 % PMID[544025]
NPT140 Organism Artemia Artemia LC50 = 105.0 ppm PMID[544022]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 36.7 ug ml-1 PMID[544022]
NPT3519 Organism Blumeria graminis f. sp. hordei Blumeria graminis f. sp. hordei IC50 = 20.0 ug.mL-1 PMID[544023]
NPT790 Organism Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv MIC = 40.3 ug.mL-1 PMID[544024]
NPT790 Organism Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv MIC = 84.7 ug.mL-1 PMID[544024]
NPT2 Others Unspecified Ratio IC50 = 0.84 n.a. PMID[544025]

☑ 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 NPC160499 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
0.9219 High Similarity NPC12070
0.9187 High Similarity NPC173978
0.9187 High Similarity NPC236189
0.9147 High Similarity NPC249272
0.9141 High Similarity NPC114183
0.9141 High Similarity NPC267205
0.907 High Similarity NPC270899
0.9048 High Similarity NPC48248
0.9032 High Similarity NPC142956
0.9024 High Similarity NPC307174
0.9008 High Similarity NPC53206
0.9008 High Similarity NPC53414
0.9008 High Similarity NPC53001
0.8992 High Similarity NPC225051
0.8976 High Similarity NPC92624
0.8939 High Similarity NPC87723
0.8931 High Similarity NPC254847
0.8931 High Similarity NPC191976
0.8931 High Similarity NPC118919
0.8923 High Similarity NPC282780
0.8923 High Similarity NPC166480
0.8923 High Similarity NPC50924
0.8906 High Similarity NPC31539
0.8906 High Similarity NPC259942
0.8906 High Similarity NPC31799
0.8898 High Similarity NPC282923
0.8898 High Similarity NPC96024
0.888 High Similarity NPC152525
0.888 High Similarity NPC68756
0.8872 High Similarity NPC242994
0.8872 High Similarity NPC138099
0.8871 High Similarity NPC300274
0.8864 High Similarity NPC471905
0.8855 High Similarity NPC161632
0.8837 High Similarity NPC41847
0.8837 High Similarity NPC72669
0.8837 High Similarity NPC474517
0.8828 High Similarity NPC109123
0.8828 High Similarity NPC146647
0.8828 High Similarity NPC276238
0.8828 High Similarity NPC34414
0.8806 High Similarity NPC169452
0.8806 High Similarity NPC181560
0.88 High Similarity NPC375356
0.8797 High Similarity NPC4214
0.8788 High Similarity NPC155211
0.878 High Similarity NPC206778
0.878 High Similarity NPC285829
0.8779 High Similarity NPC44437
0.876 High Similarity NPC477453
0.876 High Similarity NPC136588
0.876 High Similarity NPC199253
0.876 High Similarity NPC55949
0.876 High Similarity NPC62219
0.875 High Similarity NPC95537
0.875 High Similarity NPC296752
0.8741 High Similarity NPC110810
0.8741 High Similarity NPC246638
0.8731 High Similarity NPC143438
0.873 High Similarity NPC199273
0.873 High Similarity NPC234890
0.873 High Similarity NPC74507
0.872 High Similarity NPC244351
0.872 High Similarity NPC282577
0.872 High Similarity NPC283514
0.8712 High Similarity NPC80035
0.8702 High Similarity NPC48036
0.8702 High Similarity NPC52407
0.8692 High Similarity NPC93015
0.8692 High Similarity NPC205992
0.8692 High Similarity NPC244699
0.8689 High Similarity NPC125252
0.8682 High Similarity NPC99731
0.8678 High Similarity NPC161304
0.8676 High Similarity NPC94076
0.8676 High Similarity NPC182255
0.8676 High Similarity NPC193555
0.8661 High Similarity NPC103540
0.8661 High Similarity NPC477454
0.864 High Similarity NPC198336
0.8636 High Similarity NPC474519
0.8626 High Similarity NPC70622
0.8626 High Similarity NPC175738
0.8613 High Similarity NPC295712
0.8613 High Similarity NPC451542
0.8613 High Similarity NPC313047
0.8613 High Similarity NPC84266
0.8613 High Similarity NPC474203
0.8603 High Similarity NPC204045
0.8603 High Similarity NPC305845
0.8594 High Similarity NPC96915
0.8594 High Similarity NPC3224
0.8594 High Similarity NPC254492
0.8594 High Similarity NPC231774
0.8594 High Similarity NPC267846
0.8594 High Similarity NPC473691
0.8594 High Similarity NPC62952
0.8594 High Similarity NPC8745
0.8593 High Similarity NPC190457
0.8583 High Similarity NPC13238
0.8583 High Similarity NPC310540
0.8571 High Similarity NPC283088
0.8571 High Similarity NPC290803
0.8571 High Similarity NPC258502
0.8561 High Similarity NPC53896
0.8561 High Similarity NPC115458
0.8561 High Similarity NPC180261
0.8561 High Similarity NPC37299
0.8561 High Similarity NPC314048
0.856 High Similarity NPC222876
0.856 High Similarity NPC179092
0.856 High Similarity NPC35856
0.856 High Similarity NPC472046
0.856 High Similarity NPC178395
0.856 High Similarity NPC301987
0.856 High Similarity NPC26433
0.856 High Similarity NPC190971
0.856 High Similarity NPC244994
0.856 High Similarity NPC272454
0.856 High Similarity NPC115188
0.856 High Similarity NPC292665
0.856 High Similarity NPC159760
0.8551 High Similarity NPC227841
0.8551 High Similarity NPC21599
0.8551 High Similarity NPC193703
0.855 High Similarity NPC85342
0.8548 High Similarity NPC233165
0.8548 High Similarity NPC184579
0.854 High Similarity NPC73061
0.854 High Similarity NPC474961
0.854 High Similarity NPC135524
0.8538 High Similarity NPC303910
0.8538 High Similarity NPC474998
0.8538 High Similarity NPC278928
0.8529 High Similarity NPC183345
0.8529 High Similarity NPC168471
0.8527 High Similarity NPC69424
0.8527 High Similarity NPC84672
0.8527 High Similarity NPC72667
0.8527 High Similarity NPC105157
0.8527 High Similarity NPC78364
0.8527 High Similarity NPC98254
0.8527 High Similarity NPC30501
0.8527 High Similarity NPC176130
0.8527 High Similarity NPC162612
0.8527 High Similarity NPC100067
0.8527 High Similarity NPC23126
0.8527 High Similarity NPC190043
0.8527 High Similarity NPC266689
0.8527 High Similarity NPC169250
0.8527 High Similarity NPC72158
0.8527 High Similarity NPC116513
0.8527 High Similarity NPC103356
0.8519 High Similarity NPC416
0.8519 High Similarity NPC61398
0.8519 High Similarity NPC13715
0.8516 High Similarity NPC10926
0.8516 High Similarity NPC123506
0.8507 High Similarity NPC474813
0.8496 Intermediate Similarity NPC274876
0.8496 Intermediate Similarity NPC288089
0.8496 Intermediate Similarity NPC161964
0.8496 Intermediate Similarity NPC472262
0.8496 Intermediate Similarity NPC287604
0.8492 Intermediate Similarity NPC242895
0.8492 Intermediate Similarity NPC120545
0.8492 Intermediate Similarity NPC156139
0.8489 Intermediate Similarity NPC12402
0.8485 Intermediate Similarity NPC58685
0.848 Intermediate Similarity NPC473662
0.848 Intermediate Similarity NPC216297
0.848 Intermediate Similarity NPC7151
0.8478 Intermediate Similarity NPC174905
0.8478 Intermediate Similarity NPC66593
0.8478 Intermediate Similarity NPC293545
0.8478 Intermediate Similarity NPC471682
0.8478 Intermediate Similarity NPC163948
0.8473 Intermediate Similarity NPC198305
0.8468 Intermediate Similarity NPC41567
0.8467 Intermediate Similarity NPC187843
0.8467 Intermediate Similarity NPC290550
0.8462 Intermediate Similarity NPC21305
0.8462 Intermediate Similarity NPC221777
0.8462 Intermediate Similarity NPC473017
0.8456 Intermediate Similarity NPC162939
0.8456 Intermediate Similarity NPC26924
0.8455 Intermediate Similarity NPC108288
0.845 Intermediate Similarity NPC306765
0.845 Intermediate Similarity NPC295202
0.845 Intermediate Similarity NPC49647
0.845 Intermediate Similarity NPC227741
0.845 Intermediate Similarity NPC472047
0.845 Intermediate Similarity NPC136342
0.8444 Intermediate Similarity NPC471452
0.8444 Intermediate Similarity NPC290030
0.8444 Intermediate Similarity NPC245923
0.8433 Intermediate Similarity NPC278375
0.8429 Intermediate Similarity NPC143685
0.8425 Intermediate Similarity NPC309765
0.8425 Intermediate Similarity NPC133909

  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 NPC160499 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
0.8943 High Similarity NPD1201 Approved
0.8931 High Similarity NPD1509 Clinical (unspecified phase)
0.8661 High Similarity NPD1470 Approved
0.8551 High Similarity NPD7390 Discontinued
0.8455 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.8372 Intermediate Similarity NPD1164 Approved
0.8309 Intermediate Similarity NPD5406 Approved
0.8309 Intermediate Similarity NPD5405 Approved
0.8309 Intermediate Similarity NPD5404 Approved
0.8309 Intermediate Similarity NPD5408 Approved
0.8209 Intermediate Similarity NPD943 Approved
0.8088 Intermediate Similarity NPD1607 Approved
0.7941 Intermediate Similarity NPD1240 Approved
0.7857 Intermediate Similarity NPD2346 Discontinued
0.7842 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD9266 Approved
0.7805 Intermediate Similarity NPD74 Approved
0.7786 Intermediate Similarity NPD2935 Discontinued
0.7734 Intermediate Similarity NPD9493 Approved
0.7724 Intermediate Similarity NPD9263 Approved
0.7724 Intermediate Similarity NPD9264 Approved
0.7724 Intermediate Similarity NPD2342 Discontinued
0.7724 Intermediate Similarity NPD9267 Approved
0.7714 Intermediate Similarity NPD1510 Phase 2
0.7698 Intermediate Similarity NPD7635 Approved
0.7692 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD6232 Discontinued
0.7635 Intermediate Similarity NPD3226 Approved
0.7634 Intermediate Similarity NPD3019 Approved
0.7634 Intermediate Similarity NPD2932 Approved
0.7628 Intermediate Similarity NPD7473 Discontinued
0.7612 Intermediate Similarity NPD1283 Approved
0.7606 Intermediate Similarity NPD2344 Approved
0.7603 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD6959 Discontinued
0.7586 Intermediate Similarity NPD3300 Phase 2
0.7557 Intermediate Similarity NPD1651 Approved
0.755 Intermediate Similarity NPD7819 Suspended
0.75 Intermediate Similarity NPD2798 Approved
0.7483 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD2532 Approved
0.7483 Intermediate Similarity NPD2533 Approved
0.7483 Intermediate Similarity NPD2534 Approved
0.7483 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD5951 Approved
0.7434 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD1549 Phase 2
0.7426 Intermediate Similarity NPD1203 Approved
0.7417 Intermediate Similarity NPD288 Approved
0.7415 Intermediate Similarity NPD1511 Approved
0.7398 Intermediate Similarity NPD9261 Approved
0.7397 Intermediate Similarity NPD2309 Approved
0.7388 Intermediate Similarity NPD1281 Approved
0.7365 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD2799 Discontinued
0.7343 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD844 Approved
0.7329 Intermediate Similarity NPD7003 Approved
0.7323 Intermediate Similarity NPD4750 Phase 3
0.7315 Intermediate Similarity NPD1512 Approved
0.7308 Intermediate Similarity NPD9281 Approved
0.7292 Intermediate Similarity NPD6100 Approved
0.7292 Intermediate Similarity NPD6099 Approved
0.7292 Intermediate Similarity NPD1551 Phase 2
0.7286 Intermediate Similarity NPD2313 Discontinued
0.7286 Intermediate Similarity NPD411 Approved
0.7285 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD1934 Approved
0.7241 Intermediate Similarity NPD1471 Phase 3
0.7237 Intermediate Similarity NPD4380 Phase 2
0.7214 Intermediate Similarity NPD4625 Phase 3
0.7211 Intermediate Similarity NPD3750 Approved
0.7206 Intermediate Similarity NPD9717 Approved
0.7206 Intermediate Similarity NPD3972 Approved
0.7179 Intermediate Similarity NPD3749 Approved
0.7176 Intermediate Similarity NPD497 Approved
0.7172 Intermediate Similarity NPD2796 Approved
0.7165 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD1755 Approved
0.7143 Intermediate Similarity NPD2800 Approved
0.7143 Intermediate Similarity NPD1243 Approved
0.7132 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD1930 Approved
0.712 Intermediate Similarity NPD1929 Approved
0.7111 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD4626 Approved
0.7103 Intermediate Similarity NPD4308 Phase 3
0.7099 Intermediate Similarity NPD6020 Phase 2
0.7099 Intermediate Similarity NPD495 Approved
0.7099 Intermediate Similarity NPD498 Approved
0.7099 Intermediate Similarity NPD496 Approved
0.7097 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD2801 Approved
0.708 Intermediate Similarity NPD1608 Approved
0.7078 Intermediate Similarity NPD7411 Suspended
0.707 Intermediate Similarity NPD7075 Discontinued
0.7063 Intermediate Similarity NPD1237 Approved
0.7059 Intermediate Similarity NPD3026 Approved
0.7059 Intermediate Similarity NPD3023 Approved
0.705 Intermediate Similarity NPD2797 Approved
0.7042 Intermediate Similarity NPD3268 Approved
0.7042 Intermediate Similarity NPD3764 Approved
0.7037 Intermediate Similarity NPD3024 Approved
0.7037 Intermediate Similarity NPD3025 Approved
0.7025 Intermediate Similarity NPD845 Approved
0.7019 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD3020 Approved
0.7014 Intermediate Similarity NPD447 Suspended
0.7013 Intermediate Similarity NPD6599 Discontinued
0.7006 Intermediate Similarity NPD7768 Phase 2
0.7006 Intermediate Similarity NPD3882 Suspended
0.6994 Remote Similarity NPD5844 Phase 1
0.6987 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6985 Remote Similarity NPD2286 Discontinued
0.698 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6978 Remote Similarity NPD1876 Approved
0.6967 Remote Similarity NPD688 Clinical (unspecified phase)
0.6966 Remote Similarity NPD6651 Approved
0.6964 Remote Similarity NPD8150 Discontinued
0.6963 Remote Similarity NPD9545 Approved
0.696 Remote Similarity NPD1242 Phase 1
0.6957 Remote Similarity NPD9269 Phase 2
0.6948 Remote Similarity NPD7458 Discontinued
0.6947 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6913 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6912 Remote Similarity NPD9268 Approved
0.6911 Remote Similarity NPD2859 Approved
0.6911 Remote Similarity NPD2860 Approved
0.6905 Remote Similarity NPD1932 Approved
0.6905 Remote Similarity NPD846 Approved
0.6905 Remote Similarity NPD940 Approved
0.6901 Remote Similarity NPD6832 Phase 2
0.6897 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6894 Remote Similarity NPD5711 Approved
0.6894 Remote Similarity NPD5710 Approved
0.6892 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6887 Remote Similarity NPD643 Clinical (unspecified phase)
0.6884 Remote Similarity NPD1611 Approved
0.6875 Remote Similarity NPD6663 Approved
0.6875 Remote Similarity NPD520 Approved
0.6871 Remote Similarity NPD3748 Approved
0.6867 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6867 Remote Similarity NPD6559 Discontinued
0.6861 Remote Similarity NPD17 Approved
0.6861 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6853 Remote Similarity NPD7008 Discontinued
0.6846 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6799 Approved
0.6835 Remote Similarity NPD4878 Approved
0.6835 Remote Similarity NPD2296 Approved
0.6831 Remote Similarity NPD5736 Approved
0.6829 Remote Similarity NPD2934 Approved
0.6829 Remote Similarity NPD2933 Approved
0.6828 Remote Similarity NPD2979 Phase 3
0.6828 Remote Similarity NPD4307 Phase 2
0.6818 Remote Similarity NPD920 Approved
0.6815 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6815 Remote Similarity NPD6801 Discontinued
0.681 Remote Similarity NPD6168 Clinical (unspecified phase)
0.681 Remote Similarity NPD6167 Clinical (unspecified phase)
0.681 Remote Similarity NPD6166 Phase 2
0.6809 Remote Similarity NPD3266 Approved
0.6809 Remote Similarity NPD3267 Approved
0.6802 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6797 Remote Similarity NPD642 Clinical (unspecified phase)
0.6797 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6794 Remote Similarity NPD3021 Approved
0.6794 Remote Similarity NPD3022 Approved
0.6788 Remote Similarity NPD5691 Approved
0.6786 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6781 Remote Similarity NPD230 Phase 1
0.6774 Remote Similarity NPD1809 Phase 2
0.6772 Remote Similarity NPD1465 Phase 2
0.677 Remote Similarity NPD5494 Approved
0.6755 Remote Similarity NPD4628 Phase 3
0.675 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6746 Remote Similarity NPD2066 Phase 3
0.6742 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6736 Remote Similarity NPD5952 Clinical (unspecified phase)
0.673 Remote Similarity NPD3817 Phase 2
0.673 Remote Similarity NPD8438 Clinical (unspecified phase)
0.6727 Remote Similarity NPD7177 Discontinued
0.6721 Remote Similarity NPD1239 Approved
0.6718 Remote Similarity NPD2329 Discontinued
0.6715 Remote Similarity NPD3091 Approved
0.6713 Remote Similarity NPD9494 Approved
0.6711 Remote Similarity NPD2438 Suspended
0.6708 Remote Similarity NPD919 Approved
0.6694 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6687 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6686 Remote Similarity NPD8312 Approved
0.6686 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6686 Remote Similarity NPD8313 Approved
0.6667 Remote Similarity NPD6212 Phase 3
0.6667 Remote Similarity NPD6213 Phase 3
0.6667 Remote Similarity NPD6214 Clinical (unspecified phase)

  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