Structure

Physi-Chem Properties

Molecular Weight:  162.03
Volume:  160.296
LogP:  1.41
LogD:  1.381
LogS:  -2.18
# Rotatable Bonds:  0
TPSA:  50.44
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.597
Synthetic Accessibility Score:  1.903
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.723
MDCK Permeability:  1.7618223864701577e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.961
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.123
Plasma Protein Binding (PPB):  87.70804595947266%
Volume Distribution (VD):  0.525
Pgp-substrate:  16.4782657623291%

ADMET: Metabolism

CYP1A2-inhibitor:  0.95
CYP1A2-substrate:  0.908
CYP2C19-inhibitor:  0.212
CYP2C19-substrate:  0.072
CYP2C9-inhibitor:  0.073
CYP2C9-substrate:  0.818
CYP2D6-inhibitor:  0.197
CYP2D6-substrate:  0.726
CYP3A4-inhibitor:  0.049
CYP3A4-substrate:  0.204

ADMET: Excretion

Clearance (CL):  12.507
Half-life (T1/2):  0.83

ADMET: Toxicity

hERG Blockers:  0.089
Human Hepatotoxicity (H-HT):  0.095
Drug-inuced Liver Injury (DILI):  0.733
AMES Toxicity:  0.116
Rat Oral Acute Toxicity:  0.404
Maximum Recommended Daily Dose:  0.327
Skin Sensitization:  0.534
Carcinogencity:  0.786
Eye Corrosion:  0.657
Eye Irritation:  0.991
Respiratory Toxicity:  0.433

Download Data

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

  Natural Product: NPC141068

Natural Product ID:  NPC141068
Common Name*:   4-Hydroxycoumarins
IUPAC Name:   4-hydroxychromen-2-one
Synonyms:   4-Hydroxycoumarin
Standard InCHIKey:  VXIXUWQIVKSKSA-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H
SMILES:  O=c1cc(O)c2c(o1)cccc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL301141
PubChem CID:   54682930
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0002908] Hydroxycoumarins
          • [CHEMONTID:0002907] 4-hydroxycoumarins

*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
NPO3854 Ruta graveolens Species Rutaceae Eukaryota leaves n.a. n.a. PMID[12568545]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19191562]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20815207]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. bark n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[22207282]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[23806866]
NPO28265 Morus alba Species Moraceae Eukaryota root bark University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic 2011-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. Konya, Turkey 2007-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota leaves Chungbuk, Korea n.a. PMID[25935644]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[25981820]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. latex n.a. PMID[27294120]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota Whole Plants n.a. n.a. PMID[28093914]
NPO28265 Morus alba Species Moraceae Eukaryota Root barks n.a. n.a. PMID[3097265]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28265 Morus alba Species Moraceae 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
NPT12 Individual Protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 IC50 > 100000.0 nM PMID[464782]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Kinact > 100.0 uM PMID[464789]
NPT41 Individual Protein Aldose reductase Homo sapiens IC50 > 400000.0 nM PMID[464790]
NPT1551 Individual Protein Sorbitol dehydrogenase Homo sapiens IC50 > 400000.0 nM PMID[464790]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[464794]
NPT82 Cell Line MDA-MB-231 Homo sapiens EC50 = 100260.0 nM PMID[464798]
NPT858 Cell Line LNCaP Homo sapiens EC50 = 100510.0 nM PMID[464798]
NPT858 Cell Line LNCaP Homo sapiens EC50 = 120270.0 nM PMID[464798]
NPT306 Cell Line PC-3 Homo sapiens EC50 = 150460.0 nM PMID[464798]
NPT466 Cell Line U-937 Homo sapiens EC50 = 164120.0 nM PMID[464798]
NPT306 Cell Line PC-3 Homo sapiens EC50 = 173310.0 nM PMID[464798]
NPT83 Cell Line MCF7 Homo sapiens EC50 = 199820.0 nM PMID[464798]
NPT83 Cell Line MCF7 Homo sapiens EC50 > 200000.0 nM PMID[464798]
NPT82 Cell Line MDA-MB-231 Homo sapiens EC50 > 200000.0 nM PMID[464798]
NPT466 Cell Line U-937 Homo sapiens EC50 > 200000.0 nM PMID[464798]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens FC = 0.84 n.a. PMID[464800]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Ki > 100000.0 nM PMID[464801]
NPT1598 Individual Protein Casein kinase II alpha Homo sapiens Delta Tm = 3.8 degrees C PMID[464803]
NPT169 Cell Line B16-F10 Mus musculus IC50 = 70740.0 nM PMID[464804]
NPT29 Organism Rattus norvegicus Rattus norvegicus Cytoprotective effect = 4.62 n.a. PMID[464784]
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 195000.0 nM PMID[464786]
NPT1 Others Radical scavenging activity IC50 = 124100.0 nM PMID[464787]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 19.37 % PMID[464787]
NPT2557 Organism Dermatophagoides pteronyssinus Dermatophagoides pteronyssinus EC50 > 1.5 g/m2 PMID[464788]
NPT948 Individual Protein Carbonic anhydrase IX Homo sapiens Kinact = 0.418 uM PMID[464789]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens Kinact = 95.0 uM PMID[464789]
NPT949 Individual Protein Carbonic anhydrase XII Homo sapiens Kinact = 6.3 uM PMID[464789]
NPT2 Others Unspecified IC50 = 40500.0 nM PMID[464790]
NPT2 Others Unspecified Ratio IC50 > 9.88 n.a. PMID[464790]
NPT901 Individual Protein UDP-glucuronosyltransferase 1-1 Homo sapiens Activity = 0.0 pm/min/mg PMID[464792]
NPT699 Individual Protein UDP-glucuronosyltransferase 1-10 Homo sapiens Activity = 4.0 pm/min/mg PMID[464792]
NPT699 Individual Protein UDP-glucuronosyltransferase 1-10 Homo sapiens Activity = 0.0 pm/min/mg PMID[464792]
NPT694 Individual Protein UDP-glucuronosyltransferase 1-3 Homo sapiens Activity = 0.0 pm/min/mg PMID[464792]
NPT902 Individual Protein UDP-glucuronosyltransferase 1A4 Homo sapiens Activity = 0.0 pm/min/mg PMID[464792]
NPT903 Individual Protein UDP-glucuronosyltransferase 1-7 Homo sapiens Activity = 4.0 pm/min/mg PMID[464792]
NPT695 Individual Protein UDP-glucuronosyltransferase 1-8 Homo sapiens Activity = 230.0 pm/min/mg PMID[464792]
NPT696 Individual Protein UDP-glucuronosyltransferase 2A1 Homo sapiens Activity = 8.3 pm/min/mg PMID[464792]
NPT704 Individual Protein UDP-glucuronosyltransferase 2B15 Homo sapiens Activity = 0.0 pm/min/mg PMID[464792]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 186.0 umolequiv/g PMID[464793]
NPT1 Others Radical scavenging activity EC50 = 3800000.0 nM PMID[464793]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 2.07 %/mmol PMID[464793]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 61.9 % PMID[464795]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 4.2 equiv PMID[464795]
NPT2241 Organism Glomerella acutata Glomerella acutata Activity = 15.0 % PMID[464796]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus log(1/MIC) = 1.89 n.a. PMID[464797]
NPT185 Organism Aspergillus flavus Aspergillus flavus MIC >= 2048.0 ug.mL-1 PMID[464797]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC >= 2048.0 ug.mL-1 PMID[464797]
NPT27 Others Unspecified EC50 > 200000.0 nM PMID[464798]
NPT35 Others n.a. EC50 = 351300.0 nM PMID[464800]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens Ki = 95000.0 nM PMID[464801]
NPT948 Individual Protein Carbonic anhydrase IX Homo sapiens Ki = 410.0 nM PMID[464801]
NPT949 Individual Protein Carbonic anhydrase XII Homo sapiens Ki = 6300.0 nM PMID[464801]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 > 100000.0 nM PMID[464802]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. TGI > 100000.0 nM PMID[464802]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. LC50 > 100000.0 nM PMID[464802]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 83600.0 nM PMID[464802]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 95340.0 nM PMID[464802]
NPT2 Others Unspecified IC50 = 4.0 10^5uM PMID[464805]

☑ 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 NPC141068 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
0.9444 High Similarity NPC33717
0.9333 High Similarity NPC149545
0.932 High Similarity NPC139891
0.9107 High Similarity NPC474874
0.9107 High Similarity NPC247553
0.9107 High Similarity NPC193193
0.9107 High Similarity NPC31314
0.9091 High Similarity NPC163398
0.9074 High Similarity NPC266116
0.9027 High Similarity NPC302107
0.8947 High Similarity NPC52247
0.8783 High Similarity NPC187868
0.8774 High Similarity NPC227255
0.8772 High Similarity NPC14177
0.875 High Similarity NPC128633
0.8718 High Similarity NPC229113
0.8696 High Similarity NPC307253
0.8644 High Similarity NPC244495
0.8644 High Similarity NPC168259
0.8644 High Similarity NPC93219
0.8632 High Similarity NPC248786
0.8596 High Similarity NPC152306
0.8596 High Similarity NPC265547
0.8596 High Similarity NPC96705
0.8571 High Similarity NPC87563
0.8547 High Similarity NPC311219
0.8534 High Similarity NPC319378
0.8522 High Similarity NPC298796
0.8522 High Similarity NPC281356
0.8509 High Similarity NPC183154
0.8509 High Similarity NPC263754
0.85 High Similarity NPC258567
0.85 High Similarity NPC121740
0.85 High Similarity NPC243688
0.85 High Similarity NPC224774
0.843 Intermediate Similarity NPC469453
0.8396 Intermediate Similarity NPC107101
0.8376 Intermediate Similarity NPC235190
0.8376 Intermediate Similarity NPC163200
0.8376 Intermediate Similarity NPC180006
0.8361 Intermediate Similarity NPC238309
0.8361 Intermediate Similarity NPC474289
0.8333 Intermediate Similarity NPC2518
0.8333 Intermediate Similarity NPC109637
0.8318 Intermediate Similarity NPC307425
0.8304 Intermediate Similarity NPC233238
0.8293 Intermediate Similarity NPC32463
0.8293 Intermediate Similarity NPC2989
0.8279 Intermediate Similarity NPC185066
0.8257 Intermediate Similarity NPC127676
0.8257 Intermediate Similarity NPC128730
0.8257 Intermediate Similarity NPC288760
0.8246 Intermediate Similarity NPC235250
0.8235 Intermediate Similarity NPC257188
0.8235 Intermediate Similarity NPC248429
0.8235 Intermediate Similarity NPC13007
0.8235 Intermediate Similarity NPC302211
0.8235 Intermediate Similarity NPC96286
0.823 Intermediate Similarity NPC199462
0.8226 Intermediate Similarity NPC73738
0.8205 Intermediate Similarity NPC264976
0.819 Intermediate Similarity NPC246679
0.8182 Intermediate Similarity NPC176971
0.8174 Intermediate Similarity NPC296526
0.8167 Intermediate Similarity NPC315807
0.8167 Intermediate Similarity NPC109675
0.8167 Intermediate Similarity NPC273772
0.8167 Intermediate Similarity NPC472518
0.8165 Intermediate Similarity NPC283546
0.816 Intermediate Similarity NPC194277
0.816 Intermediate Similarity NPC137949
0.816 Intermediate Similarity NPC307289
0.816 Intermediate Similarity NPC281558
0.8151 Intermediate Similarity NPC144418
0.8145 Intermediate Similarity NPC113098
0.8136 Intermediate Similarity NPC230951
0.8108 Intermediate Similarity NPC151530
0.8108 Intermediate Similarity NPC194034
0.8108 Intermediate Similarity NPC157473
0.8099 Intermediate Similarity NPC201667
0.8099 Intermediate Similarity NPC27671
0.8099 Intermediate Similarity NPC111347
0.8099 Intermediate Similarity NPC193805
0.8099 Intermediate Similarity NPC89630
0.8099 Intermediate Similarity NPC73413
0.8095 Intermediate Similarity NPC31849
0.8095 Intermediate Similarity NPC163557
0.8091 Intermediate Similarity NPC473393
0.8091 Intermediate Similarity NPC473855
0.808 Intermediate Similarity NPC272650
0.808 Intermediate Similarity NPC29734
0.808 Intermediate Similarity NPC267336
0.808 Intermediate Similarity NPC250727
0.8073 Intermediate Similarity NPC179686
0.807 Intermediate Similarity NPC280760
0.807 Intermediate Similarity NPC474920
0.8049 Intermediate Similarity NPC95034
0.8049 Intermediate Similarity NPC142087
0.8036 Intermediate Similarity NPC206341
0.8036 Intermediate Similarity NPC291837
0.8034 Intermediate Similarity NPC45104
0.8033 Intermediate Similarity NPC88403
0.8033 Intermediate Similarity NPC4164
0.8031 Intermediate Similarity NPC131950
0.8031 Intermediate Similarity NPC92830
0.8031 Intermediate Similarity NPC204353
0.8031 Intermediate Similarity NPC50896
0.8031 Intermediate Similarity NPC326600
0.8017 Intermediate Similarity NPC173350
0.8017 Intermediate Similarity NPC154176
0.8017 Intermediate Similarity NPC51345
0.8017 Intermediate Similarity NPC301321
0.8017 Intermediate Similarity NPC290605
0.8016 Intermediate Similarity NPC105541
0.8 Intermediate Similarity NPC90903
0.8 Intermediate Similarity NPC476165
0.7984 Intermediate Similarity NPC2401
0.7984 Intermediate Similarity NPC146540
0.7984 Intermediate Similarity NPC81261
0.7982 Intermediate Similarity NPC84325
0.7967 Intermediate Similarity NPC234109
0.7967 Intermediate Similarity NPC188327
0.7966 Intermediate Similarity NPC124916
0.7966 Intermediate Similarity NPC74821
0.7965 Intermediate Similarity NPC79543
0.7965 Intermediate Similarity NPC259554
0.7963 Intermediate Similarity NPC307039
0.7953 Intermediate Similarity NPC277021
0.7953 Intermediate Similarity NPC469449
0.7953 Intermediate Similarity NPC2363
0.7951 Intermediate Similarity NPC291899
0.7951 Intermediate Similarity NPC140521
0.7951 Intermediate Similarity NPC98509
0.7934 Intermediate Similarity NPC151237
0.7934 Intermediate Similarity NPC27198
0.7931 Intermediate Similarity NPC161696
0.7931 Intermediate Similarity NPC114144
0.7928 Intermediate Similarity NPC8302
0.792 Intermediate Similarity NPC168710
0.7909 Intermediate Similarity NPC304638
0.7907 Intermediate Similarity NPC38099
0.7907 Intermediate Similarity NPC317045
0.7907 Intermediate Similarity NPC115861
0.7907 Intermediate Similarity NPC26954
0.7907 Intermediate Similarity NPC246177
0.7899 Intermediate Similarity NPC137294
0.7899 Intermediate Similarity NPC295259
0.7899 Intermediate Similarity NPC98748
0.7899 Intermediate Similarity NPC85895
0.7895 Intermediate Similarity NPC88868
0.7895 Intermediate Similarity NPC473809
0.7895 Intermediate Similarity NPC25067
0.7895 Intermediate Similarity NPC231251
0.7895 Intermediate Similarity NPC106141
0.7891 Intermediate Similarity NPC62366
0.7891 Intermediate Similarity NPC98179
0.7891 Intermediate Similarity NPC253574
0.789 Intermediate Similarity NPC253746
0.7886 Intermediate Similarity NPC471827
0.7886 Intermediate Similarity NPC202594
0.7886 Intermediate Similarity NPC232692
0.7886 Intermediate Similarity NPC471828
0.7886 Intermediate Similarity NPC249836
0.7881 Intermediate Similarity NPC217423
0.7876 Intermediate Similarity NPC241549
0.787 Intermediate Similarity NPC95755
0.7863 Intermediate Similarity NPC188907
0.7863 Intermediate Similarity NPC473718
0.7857 Intermediate Similarity NPC326447
0.7846 Intermediate Similarity NPC20511
0.7846 Intermediate Similarity NPC474886
0.7846 Intermediate Similarity NPC184861
0.7846 Intermediate Similarity NPC139548
0.7846 Intermediate Similarity NPC95162
0.7846 Intermediate Similarity NPC281014
0.7846 Intermediate Similarity NPC38874
0.7846 Intermediate Similarity NPC212124
0.7846 Intermediate Similarity NPC52086
0.7846 Intermediate Similarity NPC294456
0.7846 Intermediate Similarity NPC225106
0.7846 Intermediate Similarity NPC76336
0.7846 Intermediate Similarity NPC148835
0.784 Intermediate Similarity NPC472519
0.784 Intermediate Similarity NPC199204
0.784 Intermediate Similarity NPC219923
0.784 Intermediate Similarity NPC157212
0.7838 Intermediate Similarity NPC108875
0.7838 Intermediate Similarity NPC38079
0.7833 Intermediate Similarity NPC233282
0.7833 Intermediate Similarity NPC2058
0.7829 Intermediate Similarity NPC281169
0.7829 Intermediate Similarity NPC51087
0.7829 Intermediate Similarity NPC161856
0.7829 Intermediate Similarity NPC33986
0.7829 Intermediate Similarity NPC291119
0.7823 Intermediate Similarity NPC471826
0.7823 Intermediate Similarity NPC101894
0.7818 Intermediate Similarity NPC94343
0.7818 Intermediate Similarity NPC51633
0.7815 Intermediate Similarity NPC94637

  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 NPC141068 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
0.932 High Similarity NPD9697 Approved
0.8947 High Similarity NPD422 Phase 1
0.8718 High Similarity NPD3225 Approved
0.8644 High Similarity NPD2797 Approved
0.8547 High Similarity NPD9717 Approved
0.8487 Intermediate Similarity NPD1203 Approved
0.8293 Intermediate Similarity NPD3268 Approved
0.8108 Intermediate Similarity NPD290 Approved
0.8067 Intermediate Similarity NPD3496 Discontinued
0.8033 Intermediate Similarity NPD3267 Approved
0.8033 Intermediate Similarity NPD3266 Approved
0.8018 Intermediate Similarity NPD968 Approved
0.8 Intermediate Similarity NPD411 Approved
0.7966 Intermediate Similarity NPD1548 Phase 1
0.7913 Intermediate Similarity NPD5535 Approved
0.7907 Intermediate Similarity NPD4308 Phase 3
0.7857 Intermediate Similarity NPD3134 Approved
0.784 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD1778 Approved
0.7812 Intermediate Similarity NPD447 Suspended
0.7797 Intermediate Similarity NPD9493 Approved
0.7788 Intermediate Similarity NPD1358 Approved
0.7717 Intermediate Similarity NPD1296 Phase 2
0.7712 Intermediate Similarity NPD6671 Approved
0.7705 Intermediate Similarity NPD1535 Discovery
0.7705 Intermediate Similarity NPD1091 Approved
0.7698 Intermediate Similarity NPD6832 Phase 2
0.7686 Intermediate Similarity NPD4626 Approved
0.768 Intermediate Similarity NPD1019 Discontinued
0.7674 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD5124 Phase 1
0.7667 Intermediate Similarity NPD1894 Discontinued
0.7642 Intermediate Similarity NPD1481 Phase 2
0.7632 Intermediate Similarity NPD9267 Approved
0.7632 Intermediate Similarity NPD9264 Approved
0.7632 Intermediate Similarity NPD9263 Approved
0.7597 Intermediate Similarity NPD4307 Phase 2
0.7578 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD1048 Approved
0.7578 Intermediate Similarity NPD2313 Discontinued
0.7576 Intermediate Similarity NPD1551 Phase 2
0.7565 Intermediate Similarity NPD74 Approved
0.7565 Intermediate Similarity NPD9266 Approved
0.7561 Intermediate Similarity NPD1610 Phase 2
0.7561 Intermediate Similarity NPD1611 Approved
0.7542 Intermediate Similarity NPD1241 Discontinued
0.7537 Intermediate Similarity NPD1652 Phase 2
0.75 Intermediate Similarity NPD1608 Approved
0.7481 Intermediate Similarity NPD3750 Approved
0.7459 Intermediate Similarity NPD5691 Approved
0.7414 Intermediate Similarity NPD2684 Approved
0.7405 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD7033 Discontinued
0.7328 Intermediate Similarity NPD4060 Phase 1
0.7317 Intermediate Similarity NPD5585 Approved
0.7311 Intermediate Similarity NPD821 Approved
0.7308 Intermediate Similarity NPD6798 Discontinued
0.7302 Intermediate Similarity NPD4749 Approved
0.7287 Intermediate Similarity NPD2614 Approved
0.7281 Intermediate Similarity NPD9261 Approved
0.728 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4340 Discontinued
0.7273 Intermediate Similarity NPD1933 Approved
0.7258 Intermediate Similarity NPD17 Approved
0.7239 Intermediate Similarity NPD2799 Discontinued
0.7239 Intermediate Similarity NPD3748 Approved
0.7236 Intermediate Similarity NPD9545 Approved
0.7234 Intermediate Similarity NPD1653 Approved
0.7226 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD3847 Discontinued
0.719 Intermediate Similarity NPD9281 Approved
0.7188 Intermediate Similarity NPD987 Approved
0.7185 Intermediate Similarity NPD2935 Discontinued
0.7167 Intermediate Similarity NPD7843 Approved
0.7156 Intermediate Similarity NPD9365 Approved
0.7154 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD4908 Phase 1
0.7153 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6355 Discontinued
0.7143 Intermediate Similarity NPD1184 Approved
0.7143 Intermediate Similarity NPD9694 Discovery
0.7132 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD2798 Approved
0.7132 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7131 Intermediate Similarity NPD709 Approved
0.7121 Intermediate Similarity NPD6233 Phase 2
0.7103 Intermediate Similarity NPD1282 Approved
0.7101 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD7095 Approved
0.7099 Intermediate Similarity NPD5163 Phase 2
0.7099 Intermediate Similarity NPD4625 Phase 3
0.7083 Intermediate Similarity NPD228 Approved
0.708 Intermediate Similarity NPD1549 Phase 2
0.708 Intermediate Similarity NPD9273 Approved
0.7077 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD454 Approved
0.7068 Intermediate Similarity NPD4140 Approved
0.7068 Intermediate Similarity NPD1240 Approved
0.7054 Intermediate Similarity NPD6362 Approved
0.7045 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD940 Approved
0.7043 Intermediate Similarity NPD846 Approved
0.7042 Intermediate Similarity NPD5403 Approved
0.7034 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD4359 Approved
0.7029 Intermediate Similarity NPD1243 Approved
0.7021 Intermediate Similarity NPD5401 Approved
0.7021 Intermediate Similarity NPD1578 Phase 2
0.7007 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD2346 Discontinued
0.7 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.6992 Remote Similarity NPD2557 Approved
0.6992 Remote Similarity NPD4062 Phase 3
0.6992 Remote Similarity NPD7157 Approved
0.6985 Remote Similarity NPD1510 Phase 2
0.6977 Remote Similarity NPD1283 Approved
0.6972 Remote Similarity NPD9295 Approved
0.6964 Remote Similarity NPD2933 Approved
0.6964 Remote Similarity NPD2934 Approved
0.6963 Remote Similarity NPD1607 Approved
0.6963 Remote Similarity NPD6653 Approved
0.6957 Remote Similarity NPD2424 Discontinued
0.6953 Remote Similarity NPD2235 Phase 2
0.6953 Remote Similarity NPD2231 Phase 2
0.695 Remote Similarity NPD1511 Approved
0.695 Remote Similarity NPD6799 Approved
0.6947 Remote Similarity NPD2861 Phase 2
0.6947 Remote Similarity NPD2237 Approved
0.6944 Remote Similarity NPD5808 Clinical (unspecified phase)
0.694 Remote Similarity NPD1612 Clinical (unspecified phase)
0.694 Remote Similarity NPD1613 Approved
0.6934 Remote Similarity NPD4477 Approved
0.6934 Remote Similarity NPD6032 Approved
0.6934 Remote Similarity NPD4476 Approved
0.6917 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6916 Remote Similarity NPD111 Approved
0.6912 Remote Similarity NPD7097 Phase 1
0.6903 Remote Similarity NPD2859 Approved
0.6903 Remote Similarity NPD2860 Approved
0.6903 Remote Similarity NPD844 Approved
0.6901 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6901 Remote Similarity NPD642 Clinical (unspecified phase)
0.6901 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6583 Phase 3
0.6899 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6582 Phase 2
0.6897 Remote Similarity NPD291 Approved
0.6885 Remote Similarity NPD1138 Approved
0.6884 Remote Similarity NPD6002 Phase 3
0.6884 Remote Similarity NPD5762 Approved
0.6884 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6884 Remote Similarity NPD6004 Phase 3
0.6884 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6884 Remote Similarity NPD2344 Approved
0.6884 Remote Similarity NPD5763 Approved
0.6884 Remote Similarity NPD6005 Phase 3
0.688 Remote Similarity NPD1758 Phase 1
0.688 Remote Similarity NPD7644 Approved
0.6879 Remote Similarity NPD6667 Approved
0.6879 Remote Similarity NPD6666 Approved
0.6875 Remote Similarity NPD845 Approved
0.687 Remote Similarity NPD3691 Phase 2
0.687 Remote Similarity NPD3690 Phase 2
0.687 Remote Similarity NPD5647 Approved
0.6857 Remote Similarity NPD4628 Phase 3
0.6853 Remote Similarity NPD1512 Approved
0.685 Remote Similarity NPD2423 Clinical (unspecified phase)
0.685 Remote Similarity NPD6516 Phase 2
0.685 Remote Similarity NPD5846 Approved
0.6849 Remote Similarity NPD7411 Suspended
0.6846 Remote Similarity NPD196 Phase 1
0.6842 Remote Similarity NPD288 Approved
0.6829 Remote Similarity NPD592 Approved
0.6829 Remote Similarity NPD594 Approved
0.6829 Remote Similarity NPD1398 Phase 1
0.6828 Remote Similarity NPD3226 Approved
0.6825 Remote Similarity NPD1182 Approved
0.6825 Remote Similarity NPD1759 Phase 1
0.6825 Remote Similarity NPD2486 Discontinued
0.6815 Remote Similarity NPD2203 Discontinued
0.6812 Remote Similarity NPD1537 Approved
0.6812 Remote Similarity NPD2862 Discontinued
0.6812 Remote Similarity NPD6100 Approved
0.6812 Remote Similarity NPD6099 Approved
0.6812 Remote Similarity NPD2796 Approved
0.6812 Remote Similarity NPD1519 Approved
0.6812 Remote Similarity NPD1538 Phase 1
0.681 Remote Similarity NPD1242 Phase 1
0.681 Remote Similarity NPD289 Clinical (unspecified phase)
0.6803 Remote Similarity NPD969 Suspended
0.6803 Remote Similarity NPD1139 Approved
0.6803 Remote Similarity NPD1137 Approved
0.6794 Remote Similarity NPD1164 Approved
0.6788 Remote Similarity NPD1536 Approved
0.6783 Remote Similarity NPD7410 Clinical (unspecified phase)
0.678 Remote Similarity NPD5909 Discontinued
0.6777 Remote Similarity NPD5451 Approved
0.6772 Remote Similarity NPD3049 Approved
0.6772 Remote Similarity NPD3445 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