Structure

Physi-Chem Properties

Molecular Weight:  163.06
Volume:  165.139
LogP:  1.124
LogD:  0.956
LogS:  -1.351
# Rotatable Bonds:  0
TPSA:  39.19
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.538
Synthetic Accessibility Score:  2.501
Fsp3:  0.333
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:  -4.544
MDCK Permeability:  2.796219996525906e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.058
30% Bioavailability (F30%):  0.245

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.761
Plasma Protein Binding (PPB):  58.47908020019531%
Volume Distribution (VD):  1.983
Pgp-substrate:  30.59738540649414%

ADMET: Metabolism

CYP1A2-inhibitor:  0.859
CYP1A2-substrate:  0.815
CYP2C19-inhibitor:  0.277
CYP2C19-substrate:  0.312
CYP2C9-inhibitor:  0.034
CYP2C9-substrate:  0.65
CYP2D6-inhibitor:  0.112
CYP2D6-substrate:  0.826
CYP3A4-inhibitor:  0.034
CYP3A4-substrate:  0.2

ADMET: Excretion

Clearance (CL):  10.259
Half-life (T1/2):  0.569

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.108
Drug-inuced Liver Injury (DILI):  0.463
AMES Toxicity:  0.035
Rat Oral Acute Toxicity:  0.037
Maximum Recommended Daily Dose:  0.483
Skin Sensitization:  0.34
Carcinogencity:  0.385
Eye Corrosion:  0.01
Eye Irritation:  0.795
Respiratory Toxicity:  0.049

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Similar NPs/Drugs  

  Natural Product: NPC249614

Natural Product ID:  NPC249614
Common Name*:   6-Methyl-3,4-Dihydropyrano[3,4-C]Pyridin-1-One
IUPAC Name:   6-methyl-3,4-dihydropyrano[3,4-c]pyridin-1-one
Synonyms:  
Standard InCHIKey:  KFJQLAOTTSPBMT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H9NO2/c1-6-4-7-2-3-12-9(11)8(7)5-10-6/h4-5H,2-3H2,1H3
SMILES:  Cc1cc2CCOC(=O)c2cn1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2007415
PubChem CID:   362908
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002111] Pyranopyridines

*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
NPO22686 Gentiana macrophylla Species Gentianaceae Eukaryota n.a. root n.a. PMID[16335823]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota roots n.a. n.a. PMID[17375953]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[20813533]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. stem n.a. PMID[21043460]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[21043460]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. leaf n.a. PMID[21043460]
NPO27624 Swartzia simplex Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26654828]
NPO12009 Abies pinsapo Species Pinaceae Eukaryota Wood n.a. n.a. PMID[7931362]
NPO22686 Gentiana macrophylla Species Gentianaceae Eukaryota n.a. root n.a. PMID[9397205]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15856 Podocarpus hallii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18843 Antirrhinum majus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17368 Erythrina senegalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16073 Sarcomelicope megistophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22686 Gentiana macrophylla Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19120 Strychnos aculeata Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16646 Artemisia campestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15856 Podocarpus hallii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22071 Gentiana olivieri Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16073 Sarcomelicope megistophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16646 Artemisia campestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19120 Strychnos aculeata Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16817 Aglaia argentea Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22686 Gentiana macrophylla Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18614 Gentiana turkestanorum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18843 Antirrhinum majus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17368 Erythrina senegalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16646 Artemisia campestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22686 Gentiana macrophylla Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15856 Podocarpus hallii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18843 Antirrhinum majus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22686 Gentiana macrophylla Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17368 Erythrina senegalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15518 Streptomyces netropsis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13251 Iris nertchinskia Species Tarachodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18614 Gentiana turkestanorum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12009 Abies pinsapo Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27624 Swartzia simplex Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16073 Sarcomelicope megistophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19120 Strychnos aculeata Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15856 Podocarpus hallii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18511 Latimeria chalumnae Species Coelacanthidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17699 Solanum glaucophyllum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17711 Sphenoclea zeylanica Species Sphenocleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16958 Jurinea albicaulis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16646 Artemisia campestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3046 Schisandra bicolor Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22071 Gentiana olivieri Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14721 Dentitheca habereri Species Plumulariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17054 Streptomyces gardneri Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18372 Lobophytum crassospiculatum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18843 Antirrhinum majus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22686 Gentiana macrophylla Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16817 Aglaia argentea Species Meliaceae 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
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 100000.0 nM PMID[523216]

☑ 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 NPC249614 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
0.8974 High Similarity NPC107287
0.8718 High Similarity NPC112741
0.8418 Intermediate Similarity NPC135950
0.8333 Intermediate Similarity NPC103361
0.8295 Intermediate Similarity NPC469489
0.8291 Intermediate Similarity NPC230085
0.8291 Intermediate Similarity NPC159630
0.8284 Intermediate Similarity NPC191310
0.8232 Intermediate Similarity NPC123395
0.8221 Intermediate Similarity NPC263455
0.8167 Intermediate Similarity NPC109922
0.8125 Intermediate Similarity NPC167400
0.8118 Intermediate Similarity NPC273532
0.8068 Intermediate Similarity NPC282103
0.7939 Intermediate Similarity NPC312860
0.7933 Intermediate Similarity NPC44354
0.791 Intermediate Similarity NPC207851
0.7845 Intermediate Similarity NPC138370
0.7836 Intermediate Similarity NPC41717
0.7751 Intermediate Similarity NPC113812
0.7725 Intermediate Similarity NPC251391
0.7725 Intermediate Similarity NPC289086
0.7711 Intermediate Similarity NPC313889
0.7688 Intermediate Similarity NPC470894
0.7688 Intermediate Similarity NPC324245
0.7688 Intermediate Similarity NPC320748
0.7656 Intermediate Similarity NPC472752
0.765 Intermediate Similarity NPC114974
0.764 Intermediate Similarity NPC317010
0.7638 Intermediate Similarity NPC477788
0.7629 Intermediate Similarity NPC118940
0.7606 Intermediate Similarity NPC79223
0.7604 Intermediate Similarity NPC470190
0.76 Intermediate Similarity NPC57797
0.76 Intermediate Similarity NPC250807
0.7584 Intermediate Similarity NPC164340
0.7571 Intermediate Similarity NPC84347
0.7571 Intermediate Similarity NPC476419
0.7566 Intermediate Similarity NPC328559
0.7566 Intermediate Similarity NPC32451
0.7562 Intermediate Similarity NPC473850
0.756 Intermediate Similarity NPC70406
0.7545 Intermediate Similarity NPC123906
0.754 Intermediate Similarity NPC329024
0.753 Intermediate Similarity NPC302159
0.7526 Intermediate Similarity NPC123839
0.7513 Intermediate Similarity NPC207531
0.7513 Intermediate Similarity NPC63041
0.75 Intermediate Similarity NPC309498
0.7488 Intermediate Similarity NPC477787
0.7488 Intermediate Similarity NPC228377
0.7488 Intermediate Similarity NPC328186
0.7488 Intermediate Similarity NPC122968
0.7488 Intermediate Similarity NPC146824
0.7487 Intermediate Similarity NPC470189
0.7487 Intermediate Similarity NPC40919
0.7474 Intermediate Similarity NPC48042
0.7474 Intermediate Similarity NPC304179
0.7474 Intermediate Similarity NPC472550
0.7471 Intermediate Similarity NPC209362
0.747 Intermediate Similarity NPC467188
0.7469 Intermediate Similarity NPC114310
0.7462 Intermediate Similarity NPC264674
0.7461 Intermediate Similarity NPC156044
0.7451 Intermediate Similarity NPC475362
0.7449 Intermediate Similarity NPC323551
0.7449 Intermediate Similarity NPC476467
0.7449 Intermediate Similarity NPC280473
0.7437 Intermediate Similarity NPC319556
0.7432 Intermediate Similarity NPC118084
0.7426 Intermediate Similarity NPC76565
0.7424 Intermediate Similarity NPC193361
0.7424 Intermediate Similarity NPC62844
0.7423 Intermediate Similarity NPC266249
0.7411 Intermediate Similarity NPC165837
0.7411 Intermediate Similarity NPC51008
0.7411 Intermediate Similarity NPC41724
0.741 Intermediate Similarity NPC471323
0.7407 Intermediate Similarity NPC59033
0.7407 Intermediate Similarity NPC317672
0.7405 Intermediate Similarity NPC471589
0.7389 Intermediate Similarity NPC475137
0.7389 Intermediate Similarity NPC475498
0.7381 Intermediate Similarity NPC105811
0.7379 Intermediate Similarity NPC292416
0.7379 Intermediate Similarity NPC473689
0.7379 Intermediate Similarity NPC316841
0.7374 Intermediate Similarity NPC4421
0.736 Intermediate Similarity NPC472553
0.7358 Intermediate Similarity NPC12944
0.7358 Intermediate Similarity NPC25442
0.7353 Intermediate Similarity NPC473506
0.735 Intermediate Similarity NPC187494
0.7344 Intermediate Similarity NPC57398
0.7343 Intermediate Similarity NPC244839
0.7343 Intermediate Similarity NPC319880
0.7343 Intermediate Similarity NPC320324
0.7337 Intermediate Similarity NPC477909
0.7337 Intermediate Similarity NPC194040
0.7337 Intermediate Similarity NPC470306
0.7337 Intermediate Similarity NPC42678
0.7337 Intermediate Similarity NPC477907
0.7329 Intermediate Similarity NPC322488
0.732 Intermediate Similarity NPC82053
0.7317 Intermediate Similarity NPC476110
0.7317 Intermediate Similarity NPC87152
0.7317 Intermediate Similarity NPC475631
0.7317 Intermediate Similarity NPC475600
0.7316 Intermediate Similarity NPC474916
0.7308 Intermediate Similarity NPC237702
0.7301 Intermediate Similarity NPC29702
0.73 Intermediate Similarity NPC206343
0.73 Intermediate Similarity NPC475408
0.73 Intermediate Similarity NPC471016
0.73 Intermediate Similarity NPC471014
0.73 Intermediate Similarity NPC477908
0.7297 Intermediate Similarity NPC278434
0.7296 Intermediate Similarity NPC472070
0.7288 Intermediate Similarity NPC70949
0.7286 Intermediate Similarity NPC319128
0.7286 Intermediate Similarity NPC228331
0.7282 Intermediate Similarity NPC471190
0.7282 Intermediate Similarity NPC470486
0.7282 Intermediate Similarity NPC475644
0.7282 Intermediate Similarity NPC471977
0.7282 Intermediate Similarity NPC193238
0.7277 Intermediate Similarity NPC477901
0.7273 Intermediate Similarity NPC318299
0.7273 Intermediate Similarity NPC475406
0.7264 Intermediate Similarity NPC473089
0.7264 Intermediate Similarity NPC212768
0.7264 Intermediate Similarity NPC62367
0.7264 Intermediate Similarity NPC75600
0.7264 Intermediate Similarity NPC473115
0.7264 Intermediate Similarity NPC6576
0.7264 Intermediate Similarity NPC158020
0.7263 Intermediate Similarity NPC106824
0.7253 Intermediate Similarity NPC52831
0.7253 Intermediate Similarity NPC325705
0.725 Intermediate Similarity NPC477910
0.7243 Intermediate Similarity NPC160381
0.7241 Intermediate Similarity NPC477903
0.724 Intermediate Similarity NPC470279
0.7238 Intermediate Similarity NPC38959
0.7238 Intermediate Similarity NPC327904
0.7236 Intermediate Similarity NPC317752
0.7231 Intermediate Similarity NPC313796
0.7231 Intermediate Similarity NPC314855
0.7231 Intermediate Similarity NPC313345
0.7231 Intermediate Similarity NPC315638
0.7228 Intermediate Similarity NPC84815
0.7228 Intermediate Similarity NPC216428
0.7228 Intermediate Similarity NPC472555
0.7228 Intermediate Similarity NPC301368
0.722 Intermediate Similarity NPC26881
0.7219 Intermediate Similarity NPC83111
0.7217 Intermediate Similarity NPC253482
0.7216 Intermediate Similarity NPC265100
0.7216 Intermediate Similarity NPC317572
0.7214 Intermediate Similarity NPC6981
0.7212 Intermediate Similarity NPC475596
0.7212 Intermediate Similarity NPC475303
0.7211 Intermediate Similarity NPC245916
0.7206 Intermediate Similarity NPC235364
0.7196 Intermediate Similarity NPC103230
0.7194 Intermediate Similarity NPC314297
0.7194 Intermediate Similarity NPC315545
0.719 Intermediate Similarity NPC475426
0.719 Intermediate Similarity NPC35208
0.719 Intermediate Similarity NPC327769
0.7189 Intermediate Similarity NPC311282
0.7188 Intermediate Similarity NPC284338
0.7184 Intermediate Similarity NPC213914
0.7179 Intermediate Similarity NPC327592
0.7178 Intermediate Similarity NPC294579
0.7178 Intermediate Similarity NPC144779
0.7177 Intermediate Similarity NPC30456
0.7173 Intermediate Similarity NPC90229
0.7172 Intermediate Similarity NPC309845
0.7159 Intermediate Similarity NPC242116
0.7158 Intermediate Similarity NPC202812
0.7157 Intermediate Similarity NPC477912
0.715 Intermediate Similarity NPC124029
0.715 Intermediate Similarity NPC211920
0.7143 Intermediate Similarity NPC74360
0.7143 Intermediate Similarity NPC317373
0.7143 Intermediate Similarity NPC238457
0.7136 Intermediate Similarity NPC477902
0.7136 Intermediate Similarity NPC233727
0.7136 Intermediate Similarity NPC328154
0.7136 Intermediate Similarity NPC477899
0.7136 Intermediate Similarity NPC477900
0.7135 Intermediate Similarity NPC284559
0.7135 Intermediate Similarity NPC67288
0.7122 Intermediate Similarity NPC127720
0.7122 Intermediate Similarity NPC127026
0.7122 Intermediate Similarity NPC477911
0.712 Intermediate Similarity NPC77061
0.7119 Intermediate Similarity NPC263439
0.7116 Intermediate Similarity NPC475648

  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 NPC249614 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
0.8805 High Similarity NPD820 Phase 3
0.878 High Similarity NPD485 Clinical (unspecified phase)
0.8718 High Similarity NPD9271 Approved
0.8412 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD107 Approved
0.8138 Intermediate Similarity NPD4417 Approved
0.8125 Intermediate Similarity NPD9074 Approved
0.8125 Intermediate Similarity NPD9075 Approved
0.8011 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD3947 Discontinued
0.7766 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD1783 Clinical (unspecified phase)
0.7696 Intermediate Similarity NPD2509 Approved
0.7696 Intermediate Similarity NPD2510 Approved
0.7552 Intermediate Similarity NPD3371 Approved
0.7514 Intermediate Similarity NPD1096 Discontinued
0.75 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD2831 Approved
0.7448 Intermediate Similarity NPD7396 Approved
0.7424 Intermediate Similarity NPD3389 Approved
0.7424 Intermediate Similarity NPD3394 Approved
0.7424 Intermediate Similarity NPD3393 Approved
0.7423 Intermediate Similarity NPD203 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD4376 Phase 3
0.7412 Intermediate Similarity NPD180 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD5475 Discontinued
0.7384 Intermediate Similarity NPD2581 Approved
0.7384 Intermediate Similarity NPD2582 Approved
0.7381 Intermediate Similarity NPD1270 Approved
0.7366 Intermediate Similarity NPD2336 Approved
0.736 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7323 Intermediate Similarity NPD3795 Approved
0.7323 Intermediate Similarity NPD3794 Approved
0.732 Intermediate Similarity NPD7010 Phase 3
0.7296 Intermediate Similarity NPD4506 Discontinued
0.7287 Intermediate Similarity NPD1173 Approved
0.7264 Intermediate Similarity NPD1623 Approved
0.7253 Intermediate Similarity NPD9510 Approved
0.7241 Intermediate Similarity NPD4301 Approved
0.7239 Intermediate Similarity NPD272 Approved
0.7228 Intermediate Similarity NPD7404 Approved
0.7228 Intermediate Similarity NPD6770 Approved
0.7216 Intermediate Similarity NPD5088 Discontinued
0.7213 Intermediate Similarity NPD9362 Approved
0.7213 Intermediate Similarity NPD3178 Discontinued
0.7211 Intermediate Similarity NPD2307 Discontinued
0.72 Intermediate Similarity NPD687 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD1643 Phase 3
0.7156 Intermediate Similarity NPD5891 Approved
0.715 Intermediate Similarity NPD4491 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1630 Approved
0.7121 Intermediate Similarity NPD6529 Discontinued
0.712 Intermediate Similarity NPD7061 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD1627 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD1996 Discontinued
0.7108 Intermediate Similarity NPD3280 Approved
0.7108 Intermediate Similarity NPD2896 Discontinued
0.7105 Intermediate Similarity NPD4526 Approved
0.7105 Intermediate Similarity NPD4528 Approved
0.7105 Intermediate Similarity NPD4529 Approved
0.7101 Intermediate Similarity NPD751 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD6641 Approved
0.7049 Intermediate Similarity NPD6642 Approved
0.7043 Intermediate Similarity NPD721 Approved
0.7041 Intermediate Similarity NPD5513 Phase 2
0.7024 Intermediate Similarity NPD1649 Discontinued
0.7022 Intermediate Similarity NPD1631 Approved
0.7021 Intermediate Similarity NPD9364 Phase 2
0.7021 Intermediate Similarity NPD9363 Approved
0.7019 Intermediate Similarity NPD9284 Approved
0.7005 Intermediate Similarity NPD944 Approved
0.7005 Intermediate Similarity NPD6987 Phase 1
0.7005 Intermediate Similarity NPD4889 Approved
0.7005 Intermediate Similarity NPD5901 Discontinued
0.6991 Remote Similarity NPD1483 Discontinued
0.6988 Remote Similarity NPD2670 Approved
0.697 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6959 Remote Similarity NPD175 Clinical (unspecified phase)
0.6954 Remote Similarity NPD5965 Clinical (unspecified phase)
0.6952 Remote Similarity NPD3569 Discontinued
0.695 Remote Similarity NPD5583 Clinical (unspecified phase)
0.6946 Remote Similarity NPD9506 Approved
0.6944 Remote Similarity NPD4174 Clinical (unspecified phase)
0.6931 Remote Similarity NPD4948 Discontinued
0.6923 Remote Similarity NPD6661 Clinical (unspecified phase)
0.691 Remote Similarity NPD2511 Approved
0.69 Remote Similarity NPD1367 Phase 2
0.6893 Remote Similarity NPD9382 Approved
0.6893 Remote Similarity NPD9383 Approved
0.6885 Remote Similarity NPD2076 Approved
0.6885 Remote Similarity NPD2077 Approved
0.6875 Remote Similarity NPD6665 Discontinued
0.6875 Remote Similarity NPD2809 Approved
0.6868 Remote Similarity NPD1573 Approved
0.6868 Remote Similarity NPD1575 Approved
0.6865 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6864 Remote Similarity NPD4804 Approved
0.6864 Remote Similarity NPD569 Clinical (unspecified phase)
0.686 Remote Similarity NPD8479 Phase 2
0.6859 Remote Similarity NPD8063 Discontinued
0.6845 Remote Similarity NPD4429 Discontinued
0.684 Remote Similarity NPD5801 Clinical (unspecified phase)
0.684 Remote Similarity NPD1659 Phase 1
0.6834 Remote Similarity NPD6323 Clinical (unspecified phase)
0.6832 Remote Similarity NPD648 Clinical (unspecified phase)
0.6831 Remote Similarity NPD1078 Clinical (unspecified phase)
0.6821 Remote Similarity NPD1802 Approved
0.6821 Remote Similarity NPD1801 Approved
0.682 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6818 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6816 Remote Similarity NPD9398 Clinical (unspecified phase)
0.6816 Remote Similarity NPD7467 Discontinued
0.6813 Remote Similarity NPD1292 Clinical (unspecified phase)
0.6811 Remote Similarity NPD3238 Discontinued
0.681 Remote Similarity NPD9080 Approved
0.6802 Remote Similarity NPD1352 Discontinued
0.6802 Remote Similarity NPD3813 Approved
0.68 Remote Similarity NPD7001 Phase 3
0.6796 Remote Similarity NPD926 Approved
0.6796 Remote Similarity NPD925 Approved
0.6796 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6784 Remote Similarity NPD4805 Approved
0.6782 Remote Similarity NPD7528 Approved
0.6774 Remote Similarity NPD2753 Discontinued
0.6765 Remote Similarity NPD7069 Discontinued
0.6761 Remote Similarity NPD4952 Phase 3
0.676 Remote Similarity NPD5255 Approved
0.6759 Remote Similarity NPD3006 Discontinued
0.6757 Remote Similarity NPD1586 Approved
0.6757 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6751 Remote Similarity NPD6999 Discontinued
0.6751 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6746 Remote Similarity NPD3170 Approved
0.6742 Remote Similarity NPD276 Clinical (unspecified phase)
0.6739 Remote Similarity NPD6739 Clinical (unspecified phase)
0.6721 Remote Similarity NPD1343 Approved
0.672 Remote Similarity NPD5100 Phase 3
0.6717 Remote Similarity NPD6479 Discontinued
0.6717 Remote Similarity NPD4501 Approved
0.6717 Remote Similarity NPD4500 Approved
0.6716 Remote Similarity NPD7470 Discontinued
0.6716 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6712 Remote Similarity NPD6790 Phase 1
0.6703 Remote Similarity NPD750 Phase 2
0.6702 Remote Similarity NPD1291 Clinical (unspecified phase)
0.67 Remote Similarity NPD6176 Phase 1
0.6699 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6699 Remote Similarity NPD5293 Phase 2
0.6697 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6686 Remote Similarity NPD4702 Approved
0.6686 Remote Similarity NPD4703 Approved
0.6684 Remote Similarity NPD4081 Clinical (unspecified phase)
0.6684 Remote Similarity NPD6226 Phase 3
0.6684 Remote Similarity NPD4071 Approved
0.6684 Remote Similarity NPD4072 Approved
0.6682 Remote Similarity NPD5022 Discontinued
0.6667 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4011 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4373 Phase 2
0.6651 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6649 Remote Similarity NPD7424 Clinical (unspecified phase)
0.6649 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6649 Remote Similarity NPD1587 Approved
0.6648 Remote Similarity NPD6635 Approved
0.6634 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6633 Remote Similarity NPD5228 Phase 3
0.6633 Remote Similarity NPD4427 Phase 2
0.6632 Remote Similarity NPD7233 Approved
0.6632 Remote Similarity NPD7234 Approved
0.6631 Remote Similarity NPD749 Clinical (unspecified phase)
0.663 Remote Similarity NPD5862 Discovery
0.663 Remote Similarity NPD6872 Clinical (unspecified phase)
0.6628 Remote Similarity NPD9599 Approved
0.662 Remote Similarity NPD5640 Discontinued
0.662 Remote Similarity NPD8289 Discontinued
0.6615 Remote Similarity NPD3924 Approved
0.6615 Remote Similarity NPD3923 Approved
0.6615 Remote Similarity NPD5317 Clinical (unspecified phase)
0.6615 Remote Similarity NPD7098 Clinical (unspecified phase)
0.6615 Remote Similarity NPD6569 Phase 2
0.6615 Remote Similarity NPD3921 Approved
0.6615 Remote Similarity NPD3922 Approved
0.6607 Remote Similarity NPD4369 Phase 2
0.6603 Remote Similarity NPD6578 Clinical (unspecified phase)
0.6602 Remote Similarity NPD5866 Approved
0.6598 Remote Similarity NPD6281 Approved
0.6593 Remote Similarity NPD5400 Approved
0.659 Remote Similarity NPD5020 Approved
0.6587 Remote Similarity NPD5490 Discontinued
0.6587 Remote Similarity NPD2412 Clinical (unspecified phase)
0.6587 Remote Similarity NPD8160 Phase 2
0.6583 Remote Similarity NPD7049 Clinical (unspecified phase)
0.658 Remote Similarity NPD1033 Clinical (unspecified phase)
0.658 Remote Similarity NPD1034 Phase 3
0.6578 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6578 Remote Similarity NPD5482 Discontinued
0.6578 Remote Similarity NPD482 Approved
0.6573 Remote Similarity NPD510 Phase 1
0.657 Remote Similarity NPD2823 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