Structure

Physi-Chem Properties

Molecular Weight:  278.97
Volume:  201.215
LogP:  1.633
LogD:  1.995
LogS:  -3.222
# Rotatable Bonds:  0
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.5
Synthetic Accessibility Score:  3.331
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.47
MDCK Permeability:  3.086278957198374e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.426
30% Bioavailability (F30%):  0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.806
Plasma Protein Binding (PPB):  94.99651336669922%
Volume Distribution (VD):  0.95
Pgp-substrate:  3.227411985397339%

ADMET: Metabolism

CYP1A2-inhibitor:  0.935
CYP1A2-substrate:  0.554
CYP2C19-inhibitor:  0.053
CYP2C19-substrate:  0.505
CYP2C9-inhibitor:  0.02
CYP2C9-substrate:  0.227
CYP2D6-inhibitor:  0.418
CYP2D6-substrate:  0.694
CYP3A4-inhibitor:  0.144
CYP3A4-substrate:  0.264

ADMET: Excretion

Clearance (CL):  3.845
Half-life (T1/2):  0.432

ADMET: Toxicity

hERG Blockers:  0.101
Human Hepatotoxicity (H-HT):  0.029
Drug-inuced Liver Injury (DILI):  0.865
AMES Toxicity:  0.765
Rat Oral Acute Toxicity:  0.213
Maximum Recommended Daily Dose:  0.051
Skin Sensitization:  0.857
Carcinogencity:  0.501
Eye Corrosion:  0.545
Eye Irritation:  0.994
Respiratory Toxicity:  0.063

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

  Natural Product: NPC473206

Natural Product ID:  NPC473206
Common Name*:   Diphenyleneiodonium
IUPAC Name:   n.a.
Synonyms:   Diphenyleneiodonium
Standard InCHIKey:  QFXKXRXFBRLLPQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H8I/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H/q+1
SMILES:  c1ccc2c(c1)[I+]c1c2cccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL365739
PubChem CID:   3101
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000267] Organohalogen compounds
      • [CHEMONTID:0002866] Aryl halides
        • [CHEMONTID:0001032] Aryl iodides

*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
NPO6876 Ixora coccinea Species Rubiaceae Eukaryota aerial parts collected on the campus of Kaohsiung Medical University, Taiwan 2007-Oct PMID[21106454]
NPO40931 Solanum macaonense Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[25036668]
NPO6876 Ixora coccinea Species Rubiaceae 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
NPT34 Cell Line BV-2 Mus musculus IC50 = 10200.0 nM PMID[526632]
NPT2740 Cell Line Neutrophils IC50 = 969.7 nM PMID[526645]
NPT537 Individual Protein Ras-related protein Rab-9A Homo sapiens Potency = 31622776.6 nM PMID[526649]
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 19952.6 nM PMID[526648]
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 20.0 nM PMID[526651]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens Potency = 501.2 nM PMID[526651]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens Potency = 63.1 nM PMID[526648]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 1000.0 nM PMID[526648]
NPT282 Individual Protein MAP kinase ERK2 Homo sapiens Potency = 19952.6 nM PMID[526648]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Potency = 15848.9 nM PMID[526648]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Potency = 15848.9 nM PMID[526651]
NPT1620 Individual Protein Signal transducer and activator of transcription 6 Homo sapiens Potency = 15848.9 nM PMID[526651]
NPT538 Individual Protein Niemann-Pick C1 protein Homo sapiens Potency = 183563.5 nM PMID[526649]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 19952.6 nM PMID[526651]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 12589.3 nM PMID[526648]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 12589.3 nM PMID[526651]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 3162.3 nM PMID[526651]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Potency = 3981.1 nM PMID[526651]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 3162.3 nM PMID[526648]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Potency = 794.3 nM PMID[526648]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens Potency = 100.0 nM PMID[526648]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens Potency = 1000.0 nM PMID[526651]
NPT34 Cell Line BV-2 Mus musculus IC50 = 400.0 nM PMID[526653]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 20587.8 nM PMID[526649]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 7307.8 nM PMID[526649]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 29934.9 nM PMID[526649]
NPT1139 Individual Protein Arachidonate 15-lipoxygenase, type II Homo sapiens Potency n.a. 15848.9 nM PMID[526648]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 10318.3 nM PMID[526649]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens AC50 = 1000.0 nM PMID[526651]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens AC50 = 100.0 nM PMID[526648]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens AC50 = 3162.28 nM PMID[526651]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens AC50 = 63.1 nM PMID[526648]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens AC50 = 501.19 nM PMID[526651]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens AC50 = 3162.28 nM PMID[526648]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens AC50 = 19.95 nM PMID[526648]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens AC50 = 125.89 nM PMID[526651]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens AC50 = 3981.07 nM PMID[526651]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens AC50 = 794.33 nM PMID[526648]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 19952.6 nM PMID[526649]
NPT71 Cell Line HEK293 Homo sapiens Potency n.a. 259.2 nM PMID[526649]
NPT519 Cell Line SH-SY5Y Homo sapiens Potency n.a. 15848.9 nM PMID[526649]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 15848.9 nM PMID[526649]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 33.5 nM PMID[526663]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 15.8 nM PMID[526664]
NPT605 Organism Homo sapiens Homo sapiens IC50 = 460.0 nM PMID[526631]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 860.0 nM PMID[526634]
NPT2 Others Unspecified Inhibition = 94.3 % PMID[526635]
NPT2 Others Unspecified IC50 = 16000.0 nM PMID[526635]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 520.0 nM PMID[526636]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 1680.0 nM PMID[526637]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 1700.0 nM PMID[526638]
NPT2 Others Unspecified Inhibition = 85.1 % PMID[526639]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 700.0 nM PMID[526640]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 1700.0 nM PMID[526641]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 0.54 ug.mL-1 PMID[526642]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 1000.0 nM PMID[526643]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 700.0 nM PMID[526644]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 11.0 nM PMID[526646]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 20.9 nM PMID[526646]
NPT2 Others Unspecified Ratio EC50 = 1.88 n.a. PMID[526646]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 0.35 ug.mL-1 PMID[526647]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 39810.7 nM PMID[526648]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Potency = 290.9 nM PMID[526649]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 35.5 nM PMID[526650]
NPT940 Individual Protein Serine/threonine-protein kinase mTOR Homo sapiens Potency = 58.5 nM PMID[526649]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 31622.8 nM PMID[526650]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 39810.7 nM PMID[526648]
NPT940 Individual Protein Serine/threonine-protein kinase mTOR Homo sapiens Potency = 3288.5 nM PMID[526649]
NPT940 Individual Protein Serine/threonine-protein kinase mTOR Homo sapiens Potency = 46.5 nM PMID[526649]
NPT2 Others Unspecified Potency = 17782.8 nM PMID[526648]
NPT940 Individual Protein Serine/threonine-protein kinase mTOR Homo sapiens Potency = 16481.6 nM PMID[526649]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Potency = 17782.8 nM PMID[526651]
NPT96 Individual Protein Thrombopoietin Homo sapiens Potency = 39.8 nM PMID[526651]
NPT2 Others Unspecified Potency = 70.8 nM PMID[526648]
NPT2 Others Unspecified IC50 = 400.0 nM PMID[526652]
NPT2 Others Unspecified IC50 = 300.0 nM PMID[526652]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 300.0 nM PMID[526653]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 3125.0 nM PMID[526654]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis IC50 = 8530.0 nM PMID[526654]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis IC50 = 6770.0 nM PMID[526654]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 6250.0 nM PMID[526654]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis IC50 = 1630.0 nM PMID[526654]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 23778.1 nM PMID[526649]
NPT2 Others Unspecified Potency n.a. 2059.6 nM PMID[526649]
NPT533 Protein-Protein Interaction Runt-related transcription factor 1/Core-binding factor subunit beta Homo sapiens Potency n.a. 14125.4 nM PMID[526648]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 13371.4 nM PMID[526649]
NPT2 Others Unspecified IC50 = 1020.0 nM PMID[526655]
NPT2 Others Unspecified IC50 = 1020.0 nM PMID[526656]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 11220.2 nM PMID[526649]
NPT698 Individual Protein Regulator of G-protein signaling 4 Homo sapiens Potency n.a. 26679.5 nM PMID[526649]
NPT2 Others Unspecified Potency n.a. 1157.7 nM PMID[526657]
NPT2 Others Unspecified Potency n.a. 1157.7 nM PMID[526651]
NPT2 Others Unspecified Potency n.a. 1157.7 nM PMID[526650]
NPT2 Others Unspecified Potency n.a. 1157.7 nM PMID[526649]
NPT2 Others Unspecified Potency n.a. 1157.7 nM PMID[526648]
NPT2 Others Unspecified Potency n.a. 1157.7 nM PMID[526658]
NPT2 Others Unspecified IC50 = 650.0 nM PMID[526659]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 0.7 ug.mL-1 PMID[526660]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 0.22 ug.mL-1 PMID[526661]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 930.0 nM PMID[526662]
NPT2 Others Unspecified FC = 0.73 n.a. PMID[526665]
NPT2 Others Unspecified Potency n.a. 0.1 nM PMID[526664]
NPT2 Others Unspecified Potency n.a. 891.3 nM PMID[526663]
NPT2 Others Unspecified Potency n.a. 4466.8 nM PMID[526663]
NPT2 Others Unspecified Potency n.a. 25118.9 nM PMID[526664]
NPT2 Others Unspecified Potency n.a. 166.3 nM PMID[526649]
NPT2 Others Unspecified IC50 = 800.0 nM PMID[526666]
NPT2 Others Unspecified Potency n.a. 100.0 nM PMID[526663]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 55.48 % PMID[526668]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 9.99 % PMID[526669]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 3.766 % PMID[526670]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 2.06 % PMID[526671]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.79 % PMID[526672]

☑ 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 NPC473206 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9219 High Similarity NPC113670
0.8906 High Similarity NPC246588
0.8806 High Similarity NPC267443
0.8788 High Similarity NPC291066
0.8696 High Similarity NPC251490
0.8696 High Similarity NPC263385
0.8594 High Similarity NPC36357
0.8594 High Similarity NPC114327
0.8551 High Similarity NPC139416
0.8551 High Similarity NPC246822
0.8551 High Similarity NPC213570
0.8485 Intermediate Similarity NPC71009
0.8485 Intermediate Similarity NPC22786
0.8451 Intermediate Similarity NPC1901
0.8429 Intermediate Similarity NPC72670
0.8333 Intermediate Similarity NPC135924
0.831 Intermediate Similarity NPC1008
0.831 Intermediate Similarity NPC158028
0.831 Intermediate Similarity NPC226999
0.831 Intermediate Similarity NPC87099
0.831 Intermediate Similarity NPC39799
0.831 Intermediate Similarity NPC135433
0.831 Intermediate Similarity NPC280135
0.831 Intermediate Similarity NPC193578
0.8281 Intermediate Similarity NPC198841
0.8235 Intermediate Similarity NPC264470
0.8209 Intermediate Similarity NPC200745
0.8209 Intermediate Similarity NPC66517
0.8209 Intermediate Similarity NPC29680
0.8154 Intermediate Similarity NPC300345
0.8154 Intermediate Similarity NPC65873
0.8154 Intermediate Similarity NPC120441
0.8154 Intermediate Similarity NPC212114
0.8125 Intermediate Similarity NPC149436
0.8088 Intermediate Similarity NPC88566
0.8088 Intermediate Similarity NPC21211
0.8082 Intermediate Similarity NPC258492
0.8082 Intermediate Similarity NPC96835
0.806 Intermediate Similarity NPC150196
0.806 Intermediate Similarity NPC310758
0.806 Intermediate Similarity NPC238023
0.806 Intermediate Similarity NPC54368
0.806 Intermediate Similarity NPC248705
0.806 Intermediate Similarity NPC210849
0.8 Intermediate Similarity NPC269586
0.7973 Intermediate Similarity NPC307195
0.7971 Intermediate Similarity NPC155172
0.7971 Intermediate Similarity NPC198023
0.7971 Intermediate Similarity NPC32312
0.791 Intermediate Similarity NPC147062
0.7895 Intermediate Similarity NPC255345
0.7887 Intermediate Similarity NPC22760
0.7857 Intermediate Similarity NPC36440
0.7857 Intermediate Similarity NPC178527
0.7846 Intermediate Similarity NPC277704
0.7826 Intermediate Similarity NPC45756
0.7778 Intermediate Similarity NPC297358
0.7761 Intermediate Similarity NPC8235
0.7761 Intermediate Similarity NPC64270
0.7746 Intermediate Similarity NPC6107
0.7703 Intermediate Similarity NPC54269
0.7662 Intermediate Similarity NPC66270
0.7662 Intermediate Similarity NPC245896
0.7647 Intermediate Similarity NPC169110
0.7606 Intermediate Similarity NPC113837
0.7606 Intermediate Similarity NPC289915
0.7564 Intermediate Similarity NPC159661
0.7534 Intermediate Similarity NPC5324
0.7468 Intermediate Similarity NPC315216
0.7468 Intermediate Similarity NPC50063
0.7349 Intermediate Similarity NPC148231
0.7324 Intermediate Similarity NPC50266
0.7308 Intermediate Similarity NPC249018
0.7308 Intermediate Similarity NPC3190
0.7308 Intermediate Similarity NPC9796
0.7286 Intermediate Similarity NPC45255
0.7237 Intermediate Similarity NPC212463
0.7143 Intermediate Similarity NPC147578
0.7125 Intermediate Similarity NPC272260
0.7067 Intermediate Similarity NPC200936
0.7042 Intermediate Similarity NPC200624
0.7037 Intermediate Similarity NPC164449
0.7037 Intermediate Similarity NPC184030
0.7037 Intermediate Similarity NPC95868
0.6974 Remote Similarity NPC229235
0.6962 Remote Similarity NPC110264
0.6951 Remote Similarity NPC273033
0.6951 Remote Similarity NPC12936
0.6933 Remote Similarity NPC78954
0.6933 Remote Similarity NPC311343
0.6933 Remote Similarity NPC239931
0.6933 Remote Similarity NPC82770
0.6914 Remote Similarity NPC139901
0.6914 Remote Similarity NPC151405
0.6905 Remote Similarity NPC95429
0.6905 Remote Similarity NPC133162
0.6897 Remote Similarity NPC113307
0.6883 Remote Similarity NPC74458
0.6883 Remote Similarity NPC208302
0.6875 Remote Similarity NPC179726
0.6875 Remote Similarity NPC298023
0.6867 Remote Similarity NPC121478
0.6867 Remote Similarity NPC73637
0.6842 Remote Similarity NPC235059
0.6842 Remote Similarity NPC98880
0.6842 Remote Similarity NPC169222
0.6842 Remote Similarity NPC16190
0.6835 Remote Similarity NPC189371
0.6835 Remote Similarity NPC276699
0.6829 Remote Similarity NPC71664
0.6829 Remote Similarity NPC477703
0.68 Remote Similarity NPC52330
0.6795 Remote Similarity NPC271437
0.6795 Remote Similarity NPC244738
0.6795 Remote Similarity NPC285679
0.679 Remote Similarity NPC224544
0.679 Remote Similarity NPC103488
0.6786 Remote Similarity NPC119677
0.6786 Remote Similarity NPC273758
0.6753 Remote Similarity NPC95289
0.6747 Remote Similarity NPC231986
0.6719 Remote Similarity NPC11150
0.6709 Remote Similarity NPC108218
0.6709 Remote Similarity NPC113000
0.6709 Remote Similarity NPC208075
0.6709 Remote Similarity NPC122327
0.6709 Remote Similarity NPC112609
0.6705 Remote Similarity NPC325709
0.6705 Remote Similarity NPC418308
0.6705 Remote Similarity NPC176858
0.6705 Remote Similarity NPC199567
0.6667 Remote Similarity NPC283012
0.6667 Remote Similarity NPC475199
0.6667 Remote Similarity NPC155429
0.6667 Remote Similarity NPC290638
0.6667 Remote Similarity NPC326200
0.6629 Remote Similarity NPC277277
0.6629 Remote Similarity NPC191444
0.6628 Remote Similarity NPC99482
0.6628 Remote Similarity NPC475710
0.6627 Remote Similarity NPC285716
0.6627 Remote Similarity NPC328178
0.6627 Remote Similarity NPC157055
0.6627 Remote Similarity NPC17408
0.6591 Remote Similarity NPC267262
0.6556 Remote Similarity NPC103346
0.6548 Remote Similarity NPC165212
0.6548 Remote Similarity NPC133050
0.6548 Remote Similarity NPC242628
0.6543 Remote Similarity NPC139658
0.6538 Remote Similarity NPC219246
0.6512 Remote Similarity NPC169016
0.6494 Remote Similarity NPC181786
0.6484 Remote Similarity NPC128645
0.6477 Remote Similarity NPC69057
0.6477 Remote Similarity NPC60408
0.6471 Remote Similarity NPC230068
0.6463 Remote Similarity NPC98269
0.6463 Remote Similarity NPC325662
0.6463 Remote Similarity NPC245966
0.6452 Remote Similarity NPC21959
0.6444 Remote Similarity NPC19256
0.6437 Remote Similarity NPC123476
0.6429 Remote Similarity NPC190567
0.642 Remote Similarity NPC32203
0.642 Remote Similarity NPC206800
0.642 Remote Similarity NPC98976
0.6413 Remote Similarity NPC271440
0.64 Remote Similarity NPC22627
0.6395 Remote Similarity NPC243289
0.6395 Remote Similarity NPC477770
0.6395 Remote Similarity NPC104070
0.6395 Remote Similarity NPC208183
0.6386 Remote Similarity NPC36342
0.6386 Remote Similarity NPC137847
0.6386 Remote Similarity NPC76455
0.6386 Remote Similarity NPC2785
0.6386 Remote Similarity NPC285470
0.6374 Remote Similarity NPC470926
0.6364 Remote Similarity NPC203076
0.6364 Remote Similarity NPC243166
0.6353 Remote Similarity NPC145053
0.6344 Remote Similarity NPC472880
0.6344 Remote Similarity NPC172925
0.6341 Remote Similarity NPC271642
0.6341 Remote Similarity NPC175393
0.6333 Remote Similarity NPC231591
0.6333 Remote Similarity NPC298115
0.6322 Remote Similarity NPC168855
0.6322 Remote Similarity NPC267704
0.631 Remote Similarity NPC300205
0.631 Remote Similarity NPC170484
0.6304 Remote Similarity NPC108800
0.6296 Remote Similarity NPC299134
0.6265 Remote Similarity NPC329318
0.6265 Remote Similarity NPC3672
0.6265 Remote Similarity NPC287790
0.6264 Remote Similarity NPC26224
0.625 Remote Similarity NPC474354
0.625 Remote Similarity NPC125144

  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 NPC473206 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
0.9219 High Similarity NPD675 Discontinued
0.7778 Intermediate Similarity NPD1673 Approved
0.7465 Intermediate Similarity NPD173 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD1475 Approved
0.7297 Intermediate Similarity NPD9497 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD1617 Discontinued
0.725 Intermediate Similarity NPD3981 Approved
0.725 Intermediate Similarity NPD914 Suspended
0.725 Intermediate Similarity NPD3979 Approved
0.725 Intermediate Similarity NPD3904 Approved
0.725 Intermediate Similarity NPD3903 Approved
0.716 Intermediate Similarity NPD3035 Approved
0.7108 Intermediate Similarity NPD5178 Approved
0.7105 Intermediate Similarity NPD294 Approved
0.7105 Intermediate Similarity NPD292 Approved
0.7089 Intermediate Similarity NPD4144 Approved
0.7089 Intermediate Similarity NPD4147 Approved
0.7073 Intermediate Similarity NPD4701 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD4170 Approved
0.7073 Intermediate Similarity NPD4169 Approved
0.7037 Intermediate Similarity NPD1507 Clinical (unspecified phase)
0.6988 Remote Similarity NPD2001 Discontinued
0.6988 Remote Similarity NPD4635 Approved
0.6988 Remote Similarity NPD1185 Approved
0.6951 Remote Similarity NPD4027 Approved
0.6951 Remote Similarity NPD942 Approved
0.6951 Remote Similarity NPD4026 Approved
0.6905 Remote Similarity NPD4544 Approved
0.6905 Remote Similarity NPD3429 Approved
0.6905 Remote Similarity NPD3427 Approved
0.6829 Remote Similarity NPD260 Discontinued
0.6795 Remote Similarity NPD9728 Phase 1
0.679 Remote Similarity NPD9563 Approved
0.679 Remote Similarity NPD9564 Approved
0.679 Remote Similarity NPD79 Approved
0.6786 Remote Similarity NPD423 Phase 3
0.6786 Remote Similarity NPD5288 Clinical (unspecified phase)
0.6744 Remote Similarity NPD4409 Approved
0.6744 Remote Similarity NPD4406 Approved
0.6744 Remote Similarity NPD4636 Approved
0.6709 Remote Similarity NPD9588 Approved
0.6709 Remote Similarity NPD9593 Approved
0.6709 Remote Similarity NPD9589 Approved
0.6709 Remote Similarity NPD9592 Approved
0.6709 Remote Similarity NPD9591 Approved
0.6709 Remote Similarity NPD9590 Approved
0.6709 Remote Similarity NPD80 Approved
0.6709 Remote Similarity NPD505 Clinical (unspecified phase)
0.6709 Remote Similarity NPD9594 Approved
0.6667 Remote Similarity NPD2002 Discontinued
0.6667 Remote Similarity NPD4146 Approved
0.6667 Remote Similarity NPD3428 Approved
0.6667 Remote Similarity NPD4145 Approved
0.6667 Remote Similarity NPD3426 Approved
0.6629 Remote Similarity NPD3344 Approved
0.6629 Remote Similarity NPD3346 Approved
0.6628 Remote Similarity NPD5916 Discontinued
0.6591 Remote Similarity NPD3345 Approved
0.6591 Remote Similarity NPD5675 Discontinued
0.6588 Remote Similarity NPD830 Approved
0.6588 Remote Similarity NPD3971 Phase 1
0.6588 Remote Similarity NPD831 Approved
0.6556 Remote Similarity NPD4543 Discontinued
0.6556 Remote Similarity NPD1239 Approved
0.6552 Remote Similarity NPD3099 Discontinued
0.6517 Remote Similarity NPD5656 Clinical (unspecified phase)
0.6512 Remote Similarity NPD2539 Approved
0.6512 Remote Similarity NPD2538 Approved
0.6506 Remote Similarity NPD590 Approved
0.6506 Remote Similarity NPD589 Approved
0.6484 Remote Similarity NPD4408 Approved
0.6484 Remote Similarity NPD4407 Approved
0.6484 Remote Similarity NPD1508 Approved
0.6484 Remote Similarity NPD4405 Approved
0.6477 Remote Similarity NPD4793 Discontinued
0.6452 Remote Similarity NPD5963 Phase 2
0.6452 Remote Similarity NPD5964 Phase 2
0.6444 Remote Similarity NPD3673 Approved
0.6444 Remote Similarity NPD5915 Approved
0.6444 Remote Similarity NPD3672 Approved
0.6444 Remote Similarity NPD2811 Clinical (unspecified phase)
0.6437 Remote Similarity NPD9505 Clinical (unspecified phase)
0.642 Remote Similarity NPD9716 Approved
0.6413 Remote Similarity NPD1563 Approved
0.6413 Remote Similarity NPD4542 Approved
0.6413 Remote Similarity NPD4545 Approved
0.6386 Remote Similarity NPD295 Approved
0.6386 Remote Similarity NPD225 Approved
0.6386 Remote Similarity NPD296 Approved
0.6386 Remote Similarity NPD9397 Approved
0.6386 Remote Similarity NPD9393 Approved
0.6386 Remote Similarity NPD293 Approved
0.6386 Remote Similarity NPD227 Approved
0.6364 Remote Similarity NPD5252 Clinical (unspecified phase)
0.6364 Remote Similarity NPD1697 Approved
0.6344 Remote Similarity NPD688 Clinical (unspecified phase)
0.6333 Remote Similarity NPD1629 Approved
0.6333 Remote Similarity NPD5347 Phase 2
0.6333 Remote Similarity NPD1628 Approved
0.6333 Remote Similarity NPD771 Phase 3
0.6333 Remote Similarity NPD5346 Phase 2
0.631 Remote Similarity NPD1052 Approved
0.631 Remote Similarity NPD1053 Approved
0.631 Remote Similarity NPD1051 Approved
0.6277 Remote Similarity NPD6472 Discontinued
0.6277 Remote Similarity NPD1989 Approved
0.6277 Remote Similarity NPD1843 Approved
0.6277 Remote Similarity NPD3093 Approved
0.6265 Remote Similarity NPD603 Approved
0.6264 Remote Similarity NPD4728 Approved
0.625 Remote Similarity NPD1946 Clinical (unspecified phase)
0.625 Remote Similarity NPD2205 Approved
0.625 Remote Similarity NPD2208 Approved
0.625 Remote Similarity NPD5734 Clinical (unspecified phase)
0.6237 Remote Similarity NPD3982 Approved
0.6237 Remote Similarity NPD2878 Approved
0.6237 Remote Similarity NPD3980 Approved
0.6235 Remote Similarity NPD5372 Approved
0.6235 Remote Similarity NPD5371 Approved
0.6211 Remote Similarity NPD1564 Approved
0.6211 Remote Similarity NPD5598 Approved
0.6211 Remote Similarity NPD1566 Phase 3
0.6211 Remote Similarity NPD5597 Approved
0.6211 Remote Similarity NPD2487 Clinical (unspecified phase)
0.6211 Remote Similarity NPD1565 Approved
0.6207 Remote Similarity NPD263 Approved
0.6207 Remote Similarity NPD262 Approved
0.6207 Remote Similarity NPD4000 Phase 3
0.6196 Remote Similarity NPD3000 Approved
0.6196 Remote Similarity NPD2998 Approved
0.6196 Remote Similarity NPD2997 Approved
0.617 Remote Similarity NPD5554 Approved
0.617 Remote Similarity NPD3772 Phase 3
0.617 Remote Similarity NPD4094 Approved
0.6163 Remote Similarity NPD226 Approved
0.6163 Remote Similarity NPD472 Approved
0.6146 Remote Similarity NPD5832 Phase 3
0.6118 Remote Similarity NPD508 Approved
0.6118 Remote Similarity NPD507 Approved
0.6118 Remote Similarity NPD9490 Approved
0.6111 Remote Similarity NPD650 Approved
0.6111 Remote Similarity NPD1087 Approved
0.6105 Remote Similarity NPD3456 Approved
0.6105 Remote Similarity NPD2005 Discontinued
0.6105 Remote Similarity NPD3832 Clinical (unspecified phase)
0.6105 Remote Similarity NPD2507 Clinical (unspecified phase)
0.6105 Remote Similarity NPD2895 Discontinued
0.6105 Remote Similarity NPD3458 Approved
0.6105 Remote Similarity NPD3457 Approved
0.6082 Remote Similarity NPD4737 Phase 2
0.6071 Remote Similarity NPD9294 Approved
0.6064 Remote Similarity NPD6548 Approved
0.6064 Remote Similarity NPD6549 Approved
0.6044 Remote Similarity NPD1101 Approved
0.6044 Remote Similarity NPD531 Approved
0.6042 Remote Similarity NPD4655 Approved
0.6042 Remote Similarity NPD1875 Phase 1
0.6042 Remote Similarity NPD4657 Approved
0.6023 Remote Similarity NPD1800 Clinical (unspecified phase)
0.6023 Remote Similarity NPD9491 Approved
0.6022 Remote Similarity NPD7609 Phase 3
0.6022 Remote Similarity NPD517 Discontinued
0.602 Remote Similarity NPD1616 Discontinued
0.6 Remote Similarity NPD6048 Clinical (unspecified phase)
0.6 Remote Similarity NPD6049 Phase 2
0.6 Remote Similarity NPD7344 Phase 1
0.6 Remote Similarity NPD7343 Discovery
0.5979 Remote Similarity NPD4117 Approved
0.5978 Remote Similarity NPD9349 Approved
0.5978 Remote Similarity NPD9348 Approved
0.5978 Remote Similarity NPD9351 Phase 3
0.5978 Remote Similarity NPD9350 Approved
0.5977 Remote Similarity NPD9250 Approved
0.596 Remote Similarity NPD1540 Approved
0.596 Remote Similarity NPD6588 Clinical (unspecified phase)
0.596 Remote Similarity NPD4321 Approved
0.596 Remote Similarity NPD1932 Approved
0.5957 Remote Similarity NPD752 Approved
0.5957 Remote Similarity NPD7631 Approved
0.5955 Remote Similarity NPD785 Approved
0.5955 Remote Similarity NPD9395 Approved
0.5941 Remote Similarity NPD1269 Approved
0.5941 Remote Similarity NPD1268 Approved
0.5938 Remote Similarity NPD2859 Approved
0.5938 Remote Similarity NPD2860 Approved
0.5934 Remote Similarity NPD781 Approved
0.5934 Remote Similarity NPD780 Approved
0.5934 Remote Similarity NPD783 Approved
0.5934 Remote Similarity NPD782 Approved
0.5918 Remote Similarity NPD3020 Approved
0.5918 Remote Similarity NPD4008 Approved
0.5918 Remote Similarity NPD4007 Approved
0.5914 Remote Similarity NPD1089 Approved
0.5914 Remote Similarity NPD1086 Approved
0.5914 Remote Similarity NPD1090 Approved
0.59 Remote Similarity NPD3680 Approved
0.59 Remote Similarity NPD1542 Approved
0.59 Remote Similarity NPD3682 Approved
0.59 Remote Similarity NPD5700 Clinical (unspecified phase)
0.5895 Remote Similarity NPD719 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