Structure

Physi-Chem Properties

Molecular Weight:  257.06
Volume:  255.489
LogP:  2.297
LogD:  2.754
LogS:  -4.314
# Rotatable Bonds:  3
TPSA:  58.8
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.791
Synthetic Accessibility Score:  2.639
Fsp3:  0.154
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.608
MDCK Permeability:  2.2442753106588498e-05
Pgp-inhibitor:  0.029
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.613
Plasma Protein Binding (PPB):  95.47277069091797%
Volume Distribution (VD):  0.748
Pgp-substrate:  3.377424478530884%

ADMET: Metabolism

CYP1A2-inhibitor:  0.973
CYP1A2-substrate:  0.877
CYP2C19-inhibitor:  0.673
CYP2C19-substrate:  0.346
CYP2C9-inhibitor:  0.365
CYP2C9-substrate:  0.872
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.625
CYP3A4-inhibitor:  0.057
CYP3A4-substrate:  0.261

ADMET: Excretion

Clearance (CL):  8.611
Half-life (T1/2):  0.499

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.926
Drug-inuced Liver Injury (DILI):  0.976
AMES Toxicity:  0.863
Rat Oral Acute Toxicity:  0.856
Maximum Recommended Daily Dose:  0.856
Skin Sensitization:  0.208
Carcinogencity:  0.483
Eye Corrosion:  0.14
Eye Irritation:  0.98
Respiratory Toxicity:  0.977

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  Natural Product: NPC224327

Natural Product ID:  NPC224327
Common Name*:   4-Methoxy-5-(Methylthio)-2,2'-Bipyridine-6-Carbonitrile
IUPAC Name:   4-methoxy-3-methylsulfanyl-6-pyridin-2-ylpyridine-2-carbonitrile
Synonyms:  
Standard InCHIKey:  VIGCSVTZFAZTIX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H11N3OS/c1-17-12-7-10(9-5-3-4-6-15-9)16-11(8-14)13(12)18-2/h3-7H,1-2H3
SMILES:  COc1cc(nc(c1SC)C#N)c1ccccn1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1834108
PubChem CID:   10377764
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000089] Pyridines and derivatives
        • [CHEMONTID:0000326] Bipyridines and oligopyridines

*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
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344559]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344578]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10348041]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10604756]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10695669]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10724004]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10994816]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11099231]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11132958]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11374972]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11473415]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[14738393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Australian n.a. PMID[15497950]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15813185]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15844966]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15974616]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16180833]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[1666120]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16724845]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16830891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16872146]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17125235]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17315965]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17551212]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17608531]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17844998]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17887721]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17917237]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18044841]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Indonesian n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18205372]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Northwest Territories, Canada 1995 PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18666798]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18776684]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19007176]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19129624]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19191549]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19856955]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19883065]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20092333]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20545334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20836523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028889]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21090727]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21314175]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21639131]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21728289]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21751787]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21807523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21873059]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21879726]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[22145663]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22574670]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22583058]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22591466]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22758660]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22775474]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23387796]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23662937]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24592993]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24754815]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24878306]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24964393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25211234]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25455147]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25495422]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25537064]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25918793]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25934225]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26035239]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26465675]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26798949]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26905826]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31013087]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31298537]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31894983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32298122]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8501018]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[8784423]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8931733]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8982334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031666]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031676]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066767]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066768]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9186568]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9531983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[9711246]

☑ 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
NPT519 Cell Line SH-SY5Y Homo sapiens Activity = 83.3 % PMID[485085]
NPT393 Cell Line HCT-116 Homo sapiens Inhibition = 7.37 % PMID[485085]

☑ 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 NPC224327 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
0.9474 High Similarity NPC74382
0.9474 High Similarity NPC206251
0.9281 High Similarity NPC111624
0.8824 High Similarity NPC476518
0.882 High Similarity NPC134079
0.8772 High Similarity NPC14651
0.8772 High Similarity NPC121658
0.8427 Intermediate Similarity NPC266551
0.8427 Intermediate Similarity NPC219963
0.8427 Intermediate Similarity NPC161887
0.8287 Intermediate Similarity NPC20249
0.8167 Intermediate Similarity NPC222592
0.8167 Intermediate Similarity NPC168486
0.815 Intermediate Similarity NPC25899
0.8 Intermediate Similarity NPC48192
0.7979 Intermediate Similarity NPC226202
0.7668 Intermediate Similarity NPC267928
0.7551 Intermediate Similarity NPC19872
0.75 Intermediate Similarity NPC177404
0.7444 Intermediate Similarity NPC285635
0.7424 Intermediate Similarity NPC232727
0.7423 Intermediate Similarity NPC84853
0.7374 Intermediate Similarity NPC315957
0.7374 Intermediate Similarity NPC176538
0.7304 Intermediate Similarity NPC167860
0.7304 Intermediate Similarity NPC123976
0.7291 Intermediate Similarity NPC287208
0.7286 Intermediate Similarity NPC121772
0.7263 Intermediate Similarity NPC26872
0.7259 Intermediate Similarity NPC13880
0.7255 Intermediate Similarity NPC174672
0.7236 Intermediate Similarity NPC187558
0.7178 Intermediate Similarity NPC476138
0.7178 Intermediate Similarity NPC245816
0.7171 Intermediate Similarity NPC174758
0.7166 Intermediate Similarity NPC258773
0.7151 Intermediate Similarity NPC1527
0.715 Intermediate Similarity NPC287437
0.7143 Intermediate Similarity NPC26850
0.7122 Intermediate Similarity NPC82548
0.7109 Intermediate Similarity NPC193267
0.7109 Intermediate Similarity NPC213530
0.7087 Intermediate Similarity NPC185782
0.6986 Remote Similarity NPC26679
0.6976 Remote Similarity NPC36229
0.6976 Remote Similarity NPC16452
0.6976 Remote Similarity NPC476581
0.6967 Remote Similarity NPC274982
0.6954 Remote Similarity NPC296527
0.6942 Remote Similarity NPC323345
0.6942 Remote Similarity NPC470164
0.6919 Remote Similarity NPC76748
0.6897 Remote Similarity NPC476582
0.6897 Remote Similarity NPC4071
0.6897 Remote Similarity NPC476578
0.6893 Remote Similarity NPC47059
0.6893 Remote Similarity NPC118832
0.6893 Remote Similarity NPC285558
0.6893 Remote Similarity NPC264166
0.6893 Remote Similarity NPC165349
0.6893 Remote Similarity NPC274291
0.6893 Remote Similarity NPC329708
0.6887 Remote Similarity NPC470799
0.6887 Remote Similarity NPC8022
0.6884 Remote Similarity NPC310118
0.6884 Remote Similarity NPC92111
0.6884 Remote Similarity NPC60621
0.685 Remote Similarity NPC133140
0.685 Remote Similarity NPC195268
0.6849 Remote Similarity NPC314954
0.684 Remote Similarity NPC470549
0.6837 Remote Similarity NPC284678
0.6837 Remote Similarity NPC284559
0.6835 Remote Similarity NPC153467
0.6829 Remote Similarity NPC31930
0.6821 Remote Similarity NPC118776
0.6816 Remote Similarity NPC198673
0.6816 Remote Similarity NPC307963
0.6809 Remote Similarity NPC118511
0.6808 Remote Similarity NPC170114
0.6792 Remote Similarity NPC476287
0.6771 Remote Similarity NPC24802
0.6757 Remote Similarity NPC101543
0.6757 Remote Similarity NPC469554
0.6755 Remote Similarity NPC471177
0.6755 Remote Similarity NPC59779
0.6755 Remote Similarity NPC124542
0.6745 Remote Similarity NPC202605
0.6745 Remote Similarity NPC112206
0.6745 Remote Similarity NPC53069
0.6745 Remote Similarity NPC202768
0.6745 Remote Similarity NPC296482
0.6743 Remote Similarity NPC122436
0.6727 Remote Similarity NPC110151
0.6703 Remote Similarity NPC36168
0.6699 Remote Similarity NPC234197
0.6684 Remote Similarity NPC471178
0.6683 Remote Similarity NPC168911
0.6683 Remote Similarity NPC239954
0.6683 Remote Similarity NPC324149
0.6667 Remote Similarity NPC313189
0.6667 Remote Similarity NPC171409
0.6667 Remote Similarity NPC251090
0.6667 Remote Similarity NPC96405
0.6651 Remote Similarity NPC11464
0.6651 Remote Similarity NPC290689
0.6638 Remote Similarity NPC316756
0.6636 Remote Similarity NPC292958
0.6634 Remote Similarity NPC224928
0.662 Remote Similarity NPC208284
0.6619 Remote Similarity NPC472111
0.6618 Remote Similarity NPC477019
0.6617 Remote Similarity NPC110741
0.6612 Remote Similarity NPC220523
0.6604 Remote Similarity NPC469589
0.6603 Remote Similarity NPC475774
0.6603 Remote Similarity NPC200836
0.6588 Remote Similarity NPC193238
0.6588 Remote Similarity NPC135549
0.6583 Remote Similarity NPC84478
0.6582 Remote Similarity NPC283152
0.658 Remote Similarity NPC314940
0.658 Remote Similarity NPC473764
0.6578 Remote Similarity NPC141053
0.657 Remote Similarity NPC476167
0.6566 Remote Similarity NPC470474
0.6564 Remote Similarity NPC312872
0.6562 Remote Similarity NPC260434
0.656 Remote Similarity NPC17565
0.6558 Remote Similarity NPC162530
0.6545 Remote Similarity NPC97367
0.6533 Remote Similarity NPC176127
0.6531 Remote Similarity NPC288943
0.6524 Remote Similarity NPC53144
0.6522 Remote Similarity NPC192315
0.652 Remote Similarity NPC295228
0.6516 Remote Similarity NPC322482
0.6505 Remote Similarity NPC194967
0.65 Remote Similarity NPC62069
0.6493 Remote Similarity NPC475070
0.6493 Remote Similarity NPC470500
0.649 Remote Similarity NPC18487
0.6488 Remote Similarity NPC329541
0.6488 Remote Similarity NPC289786
0.6485 Remote Similarity NPC66083
0.6476 Remote Similarity NPC211813
0.6471 Remote Similarity NPC216612
0.6468 Remote Similarity NPC473513
0.6468 Remote Similarity NPC42591
0.6459 Remote Similarity NPC329793
0.6458 Remote Similarity NPC473057
0.645 Remote Similarity NPC48938
0.6447 Remote Similarity NPC224764
0.6445 Remote Similarity NPC223427
0.6442 Remote Similarity NPC212213
0.6441 Remote Similarity NPC65277
0.644 Remote Similarity NPC120798
0.6438 Remote Similarity NPC197141
0.6438 Remote Similarity NPC173080
0.6436 Remote Similarity NPC204385
0.6435 Remote Similarity NPC264176
0.6435 Remote Similarity NPC472098
0.6419 Remote Similarity NPC470020
0.6419 Remote Similarity NPC5145
0.6419 Remote Similarity NPC235685
0.6413 Remote Similarity NPC245348
0.6413 Remote Similarity NPC471323
0.641 Remote Similarity NPC91895
0.6406 Remote Similarity NPC471080
0.6406 Remote Similarity NPC469592
0.6406 Remote Similarity NPC79911
0.6402 Remote Similarity NPC476465
0.6398 Remote Similarity NPC295898
0.6391 Remote Similarity NPC30540
0.6391 Remote Similarity NPC101350
0.6385 Remote Similarity NPC476124
0.6385 Remote Similarity NPC476121
0.6384 Remote Similarity NPC227908
0.6384 Remote Similarity NPC60006
0.6382 Remote Similarity NPC42979
0.6381 Remote Similarity NPC329747
0.6379 Remote Similarity NPC151489
0.6379 Remote Similarity NPC39092
0.6378 Remote Similarity NPC252590
0.6373 Remote Similarity NPC472289
0.6364 Remote Similarity NPC150048
0.6364 Remote Similarity NPC203754
0.6359 Remote Similarity NPC470403
0.6359 Remote Similarity NPC470394
0.6359 Remote Similarity NPC470404
0.6359 Remote Similarity NPC316981
0.6351 Remote Similarity NPC470586
0.6348 Remote Similarity NPC174421
0.6347 Remote Similarity NPC148183
0.6347 Remote Similarity NPC152768
0.6343 Remote Similarity NPC85273
0.6337 Remote Similarity NPC204717
0.6336 Remote Similarity NPC99891
0.633 Remote Similarity NPC266931
0.6326 Remote Similarity NPC475910

  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 NPC224327 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
0.7474 Intermediate Similarity NPD3396 Approved
0.7474 Intermediate Similarity NPD3395 Approved
0.7374 Intermediate Similarity NPD1740 Approved
0.7374 Intermediate Similarity NPD1739 Approved
0.7337 Intermediate Similarity NPD5259 Phase 3
0.732 Intermediate Similarity NPD2334 Discontinued
0.7273 Intermediate Similarity NPD1923 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD4795 Phase 2
0.7222 Intermediate Similarity NPD2959 Phase 3
0.7194 Intermediate Similarity NPD4372 Phase 1
0.7172 Intermediate Similarity NPD3477 Phase 2
0.7172 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD1034 Phase 3
0.7165 Intermediate Similarity NPD1033 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD925 Approved
0.7135 Intermediate Similarity NPD926 Approved
0.7123 Intermediate Similarity NPD1259 Discontinued
0.7035 Intermediate Similarity NPD1602 Discontinued
0.7021 Intermediate Similarity NPD565 Phase 2
0.702 Intermediate Similarity NPD6569 Phase 2
0.7018 Intermediate Similarity NPD2062 Phase 2
0.7005 Intermediate Similarity NPD4081 Clinical (unspecified phase)
0.6995 Remote Similarity NPD3386 Phase 2
0.6991 Remote Similarity NPD6450 Phase 2
0.6986 Remote Similarity NPD2848 Discontinued
0.6965 Remote Similarity NPD1622 Discontinued
0.6944 Remote Similarity NPD1258 Discontinued
0.6939 Remote Similarity NPD3039 Clinical (unspecified phase)
0.6931 Remote Similarity NPD5320 Approved
0.6931 Remote Similarity NPD5319 Approved
0.69 Remote Similarity NPD1304 Clinical (unspecified phase)
0.6897 Remote Similarity NPD2958 Clinical (unspecified phase)
0.6893 Remote Similarity NPD4038 Approved
0.6893 Remote Similarity NPD4033 Approved
0.6893 Remote Similarity NPD3397 Phase 2
0.6893 Remote Similarity NPD4036 Approved
0.6893 Remote Similarity NPD32 Approved
0.6893 Remote Similarity NPD4122 Approved
0.6893 Remote Similarity NPD4034 Approved
0.6893 Remote Similarity NPD31 Approved
0.6893 Remote Similarity NPD4039 Approved
0.6893 Remote Similarity NPD4035 Approved
0.6893 Remote Similarity NPD4037 Approved
0.6888 Remote Similarity NPD4889 Approved
0.6881 Remote Similarity NPD4899 Clinical (unspecified phase)
0.6878 Remote Similarity NPD2472 Approved
0.6878 Remote Similarity NPD2471 Approved
0.6875 Remote Similarity NPD2816 Clinical (unspecified phase)
0.6866 Remote Similarity NPD6246 Approved
0.6863 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6856 Remote Similarity NPD2599 Approved
0.6856 Remote Similarity NPD2600 Approved
0.6856 Remote Similarity NPD2601 Approved
0.6853 Remote Similarity NPD4375 Approved
0.685 Remote Similarity NPD3924 Approved
0.685 Remote Similarity NPD3922 Approved
0.685 Remote Similarity NPD3921 Approved
0.685 Remote Similarity NPD3923 Approved
0.6831 Remote Similarity NPD9596 Approved
0.6831 Remote Similarity NPD9595 Approved
0.6828 Remote Similarity NPD604 Clinical (unspecified phase)
0.6825 Remote Similarity NPD424 Approved
0.6825 Remote Similarity NPD425 Approved
0.6822 Remote Similarity NPD2441 Approved
0.6822 Remote Similarity NPD2440 Phase 3
0.6821 Remote Similarity NPD4204 Approved
0.6821 Remote Similarity NPD7414 Clinical (unspecified phase)
0.6821 Remote Similarity NPD4203 Approved
0.6816 Remote Similarity NPD1038 Approved
0.6804 Remote Similarity NPD1620 Clinical (unspecified phase)
0.6798 Remote Similarity NPD6769 Clinical (unspecified phase)
0.6791 Remote Similarity NPD9705 Discontinued
0.6791 Remote Similarity NPD112 Approved
0.6777 Remote Similarity NPD5066 Phase 2
0.6777 Remote Similarity NPD5067 Phase 2
0.6776 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6774 Remote Similarity NPD9574 Clinical (unspecified phase)
0.6774 Remote Similarity NPD1856 Discontinued
0.6774 Remote Similarity NPD2582 Approved
0.6774 Remote Similarity NPD2581 Approved
0.6763 Remote Similarity NPD715 Phase 3
0.6753 Remote Similarity NPD4072 Approved
0.6753 Remote Similarity NPD1032 Phase 2
0.6753 Remote Similarity NPD4071 Approved
0.6745 Remote Similarity NPD3815 Phase 1
0.6745 Remote Similarity NPD3816 Phase 1
0.6732 Remote Similarity NPD4548 Discontinued
0.6719 Remote Similarity NPD1078 Clinical (unspecified phase)
0.6716 Remote Similarity NPD2952 Discontinued
0.6712 Remote Similarity NPD1504 Discontinued
0.6712 Remote Similarity NPD2955 Approved
0.6712 Remote Similarity NPD2954 Approved
0.6698 Remote Similarity NPD7823 Clinical (unspecified phase)
0.6696 Remote Similarity NPD6276 Discontinued
0.6684 Remote Similarity NPD2782 Approved
0.6684 Remote Similarity NPD2780 Approved
0.6683 Remote Similarity NPD5144 Discontinued
0.6667 Remote Similarity NPD703 Discontinued
0.6667 Remote Similarity NPD2885 Approved
0.6667 Remote Similarity NPD2886 Approved
0.6652 Remote Similarity NPD1927 Discontinued
0.6652 Remote Similarity NPD8100 Phase 3
0.6652 Remote Similarity NPD4850 Phase 1
0.6652 Remote Similarity NPD1911 Approved
0.6652 Remote Similarity NPD1910 Approved
0.6651 Remote Similarity NPD5628 Clinical (unspecified phase)
0.6651 Remote Similarity NPD2926 Approved
0.665 Remote Similarity NPD6393 Clinical (unspecified phase)
0.6649 Remote Similarity NPD158 Discontinued
0.6638 Remote Similarity NPD1941 Approved
0.6637 Remote Similarity NPD6131 Phase 1
0.6632 Remote Similarity NPD754 Clinical (unspecified phase)
0.6619 Remote Similarity NPD5530 Phase 1
0.6619 Remote Similarity NPD5601 Phase 2
0.6618 Remote Similarity NPD5228 Phase 3
0.6618 Remote Similarity NPD1951 Clinical (unspecified phase)
0.6618 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6618 Remote Similarity NPD6389 Clinical (unspecified phase)
0.6615 Remote Similarity NPD2781 Approved
0.6606 Remote Similarity NPD1907 Phase 3
0.6605 Remote Similarity NPD6140 Clinical (unspecified phase)
0.6602 Remote Similarity NPD1788 Approved
0.6602 Remote Similarity NPD1789 Approved
0.66 Remote Similarity NPD9542 Approved
0.6588 Remote Similarity NPD1392 Approved
0.6577 Remote Similarity NPD1906 Approved
0.6576 Remote Similarity NPD1661 Suspended
0.657 Remote Similarity NPD5999 Phase 2
0.657 Remote Similarity NPD3825 Phase 3
0.6569 Remote Similarity NPD4551 Phase 2
0.6567 Remote Similarity NPD8101 Phase 3
0.6567 Remote Similarity NPD5998 Clinical (unspecified phase)
0.6567 Remote Similarity NPD6257 Clinical (unspecified phase)
0.6567 Remote Similarity NPD2749 Discontinued
0.6561 Remote Similarity NPD5255 Approved
0.6558 Remote Similarity NPD2772 Clinical (unspecified phase)
0.6558 Remote Similarity NPD2894 Phase 2
0.6558 Remote Similarity NPD2314 Clinical (unspecified phase)
0.6557 Remote Similarity NPD5528 Clinical (unspecified phase)
0.6557 Remote Similarity NPD5529 Phase 1
0.6557 Remote Similarity NPD5863 Clinical (unspecified phase)
0.6552 Remote Similarity NPD1095 Clinical (unspecified phase)
0.6552 Remote Similarity NPD4148 Approved
0.6547 Remote Similarity NPD6508 Approved
0.6547 Remote Similarity NPD5559 Phase 2
0.6544 Remote Similarity NPD1744 Approved
0.6542 Remote Similarity NPD4131 Phase 3
0.6542 Remote Similarity NPD3570 Phase 2
0.6535 Remote Similarity NPD4021 Phase 2
0.6532 Remote Similarity NPD1603 Discontinued
0.6526 Remote Similarity NPD4437 Phase 3
0.6526 Remote Similarity NPD1418 Phase 2
0.6524 Remote Similarity NPD5513 Phase 2
0.6524 Remote Similarity NPD4044 Discontinued
0.6518 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6517 Remote Similarity NPD7757 Approved
0.6517 Remote Similarity NPD7758 Approved
0.6516 Remote Similarity NPD6306 Phase 2
0.6514 Remote Similarity NPD3354 Phase 2
0.6514 Remote Similarity NPD2011 Clinical (unspecified phase)
0.6512 Remote Similarity NPD7069 Discontinued
0.6509 Remote Similarity NPD1197 Approved
0.6505 Remote Similarity NPD1704 Clinical (unspecified phase)
0.6502 Remote Similarity NPD6553 Clinical (unspecified phase)
0.65 Remote Similarity NPD4881 Clinical (unspecified phase)
0.65 Remote Similarity NPD3569 Discontinued
0.6497 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6496 Remote Similarity NPD6956 Phase 1
0.6495 Remote Similarity NPD6262 Clinical (unspecified phase)
0.6484 Remote Similarity NPD6501 Approved
0.6484 Remote Similarity NPD6500 Approved
0.6479 Remote Similarity NPD6366 Clinical (unspecified phase)
0.6473 Remote Similarity NPD6988 Phase 1
0.6473 Remote Similarity NPD6759 Phase 2
0.6471 Remote Similarity NPD3564 Approved
0.6471 Remote Similarity NPD6207 Discovery
0.6471 Remote Similarity NPD3562 Approved
0.6471 Remote Similarity NPD3563 Approved
0.6471 Remote Similarity NPD1286 Suspended
0.6466 Remote Similarity NPD5047 Clinical (unspecified phase)
0.6465 Remote Similarity NPD3939 Suspended
0.6465 Remote Similarity NPD7468 Clinical (unspecified phase)
0.6463 Remote Similarity NPD2414 Clinical (unspecified phase)
0.6462 Remote Similarity NPD2123 Phase 3
0.6462 Remote Similarity NPD9548 Phase 2
0.6457 Remote Similarity NPD7675 Phase 3
0.6457 Remote Similarity NPD7426 Phase 1
0.6457 Remote Similarity NPD7674 Phase 3
0.6457 Remote Similarity NPD7676 Clinical (unspecified phase)
0.6455 Remote Similarity NPD6856 Discontinued
0.6455 Remote Similarity NPD8479 Phase 2
0.6438 Remote Similarity NPD6568 Discontinued
0.6436 Remote Similarity NPD4920 Clinical (unspecified phase)
0.6436 Remote Similarity NPD4921 Phase 3
0.6436 Remote Similarity NPD4919 Phase 3
0.6435 Remote Similarity NPD3330 Phase 1
0.6435 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6432 Remote Similarity NPD26 Approved
0.6432 Remote Similarity NPD25 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