Structure

Physi-Chem Properties

Molecular Weight:  305.2
Volume:  335.513
LogP:  2.699
LogD:  3.189
LogS:  -3.325
# Rotatable Bonds:  10
TPSA:  58.56
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.539
Synthetic Accessibility Score:  2.19
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.612
MDCK Permeability:  3.258488868596032e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.022
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.982
30% Bioavailability (F30%):  0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.806
Plasma Protein Binding (PPB):  94.89263153076172%
Volume Distribution (VD):  0.694
Pgp-substrate:  2.3406379222869873%

ADMET: Metabolism

CYP1A2-inhibitor:  0.636
CYP1A2-substrate:  0.878
CYP2C19-inhibitor:  0.832
CYP2C19-substrate:  0.817
CYP2C9-inhibitor:  0.695
CYP2C9-substrate:  0.921
CYP2D6-inhibitor:  0.831
CYP2D6-substrate:  0.884
CYP3A4-inhibitor:  0.896
CYP3A4-substrate:  0.282

ADMET: Excretion

Clearance (CL):  10.618
Half-life (T1/2):  0.947

ADMET: Toxicity

hERG Blockers:  0.07
Human Hepatotoxicity (H-HT):  0.277
Drug-inuced Liver Injury (DILI):  0.052
AMES Toxicity:  0.081
Rat Oral Acute Toxicity:  0.059
Maximum Recommended Daily Dose:  0.019
Skin Sensitization:  0.909
Carcinogencity:  0.064
Eye Corrosion:  0.004
Eye Irritation:  0.042
Respiratory Toxicity:  0.048

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

  Natural Product: NPC308885

Natural Product ID:  NPC308885
Common Name*:   Zucapsaicin
IUPAC Name:   (Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
Synonyms:   Zucapsaicin
Standard InCHIKey:  YKPUWZUDDOIDPM-VURMDHGXSA-N
Standard InCHI:  InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6-
SMILES:  CC(C)/C=CCCCCC(=NCc1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL313971
PubChem CID:   1548942
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0000190] Methoxyphenols

*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
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. fruit n.a. PMID[12932131]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[20460582]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. fruit n.a. PMID[25172746]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[8910532]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Resin, Exudate, Sap n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16501 Capsicum annuum Species Solanaceae 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
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 39810.7 nM PMID[493016]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens Potency = 6309.6 nM PMID[493017]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens Potency = 7943.3 nM PMID[493016]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens Potency = 10000.0 nM PMID[493018]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Potency = 6309.6 nM PMID[493017]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Potency = 15848.9 nM PMID[493018]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 31622.8 nM PMID[493016]
NPT277 Individual Protein Caspase-1 Homo sapiens Potency = 15848.9 nM PMID[493019]
NPT60 Individual Protein Lysosomal alpha-glucosidase Homo sapiens Potency = 14125.4 nM PMID[493020]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Potency = 15848.9 nM PMID[493017]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Potency = 6309.6 nM PMID[493016]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 3981.1 nM PMID[493019]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 3981.1 nM PMID[493017]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Potency = 25118.9 nM PMID[493018]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 7943.3 nM PMID[493016]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens Potency = 3981.1 nM PMID[493018]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens Potency = 316.2 nM PMID[493019]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens Potency = 1258.9 nM PMID[493017]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens Potency = 1995.3 nM PMID[493016]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens AC50 = 1258.93 nM PMID[493017]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens AC50 = 1995.26 nM PMID[493016]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens AC50 = 3162.28 nM PMID[493017]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens AC50 = 7943.28 nM PMID[493016]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens AC50 = 7943.28 nM PMID[493016]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens AC50 = 316.23 nM PMID[493019]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens AC50 = 15848.93 nM PMID[493017]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens AC50 = 1584.89 nM PMID[493016]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens AC50 = 6309.57 nM PMID[493016]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens AC50 = 3981.07 nM PMID[493017]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens AC50 = 6309.57 nM PMID[493017]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens AC50 = 1584.89 nM PMID[493019]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens AC50 = 3981.07 nM PMID[493019]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 35481.3 nM PMID[493019]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29855.4 nM PMID[493021]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 33498.3 nM PMID[493022]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 33498.3 nM PMID[493021]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 44668.4 nM PMID[493017]
NPT472 Individual Protein Vanilloid receptor Homo sapiens Ki = 1080.0 nM PMID[493023]
NPT472 Individual Protein Vanilloid receptor Homo sapiens EC50 = 28.2 nM PMID[493023]
NPT32 Organism Mus musculus Mus musculus Latency > 39.9 n.a. PMID[493015]
NPT32 Organism Mus musculus Mus musculus Response = 6.0 n.a. PMID[493015]
NPT29 Organism Rattus norvegicus Rattus norvegicus Analgesia = 0.0 % PMID[493015]
NPT32 Organism Mus musculus Mus musculus Inhibition = 79.5 % PMID[493015]
NPT32 Organism Mus musculus Mus musculus Lethality = 50.0 % PMID[493015]
NPT791 Individual Protein Cruzipain Trypanosoma cruzi Potency = 39810.7 nM PMID[493016]
NPT791 Individual Protein Cruzipain Trypanosoma cruzi Potency = 39810.7 nM PMID[493017]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 3548.1 nM PMID[493019]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 25118.9 nM PMID[493016]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 22387.2 nM PMID[493017]
NPT2 Others Unspecified Potency = 14125.4 nM PMID[493016]
NPT2 Others Unspecified Potency = 28183.8 nM PMID[493017]
NPT2 Others Unspecified Potency n.a. 22387.2 nM PMID[493021]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 12.44 % PMID[493024]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.17 % PMID[493025]
NPT20 Organism Candida albicans Candida albicans Inhibition = 4.72 % PMID[493026]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans Inhibition = -5.9 % PMID[493026]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 0.0 % PMID[493026]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae Inhibition = 12.92 % PMID[493026]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 15.26 % PMID[493026]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = 26.82 % PMID[493026]
NPT2922 Organism Staphylococcus aureus subsp. aureus Staphylococcus aureus subsp. aureus Inhibition = 14.17 % PMID[493026]

☑ 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 NPC308885 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
1.0 High Similarity NPC255550
0.9762 High Similarity NPC218530
0.976 High Similarity NPC130595
0.976 High Similarity NPC93882
0.9683 High Similarity NPC285078
0.9683 High Similarity NPC6854
0.9683 High Similarity NPC313737
0.9286 High Similarity NPC153990
0.907 High Similarity NPC114102
0.9062 High Similarity NPC155838
0.9 High Similarity NPC214869
0.8992 High Similarity NPC52029
0.8992 High Similarity NPC35961
0.8992 High Similarity NPC195749
0.8837 High Similarity NPC186898
0.8837 High Similarity NPC251571
0.876 High Similarity NPC301713
0.8651 High Similarity NPC53596
0.8651 High Similarity NPC289330
0.8651 High Similarity NPC17388
0.8651 High Similarity NPC160120
0.8651 High Similarity NPC471308
0.8601 High Similarity NPC275027
0.8529 High Similarity NPC204848
0.8529 High Similarity NPC312770
0.8529 High Similarity NPC41473
0.8529 High Similarity NPC14600
0.8529 High Similarity NPC160607
0.8527 High Similarity NPC13020
0.8527 High Similarity NPC140359
0.8473 Intermediate Similarity NPC251466
0.8467 Intermediate Similarity NPC299583
0.8467 Intermediate Similarity NPC296898
0.845 Intermediate Similarity NPC471315
0.845 Intermediate Similarity NPC471314
0.8409 Intermediate Similarity NPC191302
0.8397 Intermediate Similarity NPC246133
0.8397 Intermediate Similarity NPC170583
0.8397 Intermediate Similarity NPC71105
0.8397 Intermediate Similarity NPC152186
0.8397 Intermediate Similarity NPC182147
0.8397 Intermediate Similarity NPC207541
0.8333 Intermediate Similarity NPC156944
0.8321 Intermediate Similarity NPC131204
0.8321 Intermediate Similarity NPC301050
0.8321 Intermediate Similarity NPC300955
0.832 Intermediate Similarity NPC142599
0.8286 Intermediate Similarity NPC100478
0.8286 Intermediate Similarity NPC222039
0.8276 Intermediate Similarity NPC52475
0.8271 Intermediate Similarity NPC291449
0.8271 Intermediate Similarity NPC41331
0.8271 Intermediate Similarity NPC157740
0.8271 Intermediate Similarity NPC172403
0.8271 Intermediate Similarity NPC99798
0.8239 Intermediate Similarity NPC5462
0.8219 Intermediate Similarity NPC18614
0.8211 Intermediate Similarity NPC246358
0.8211 Intermediate Similarity NPC7097
0.8211 Intermediate Similarity NPC233731
0.8211 Intermediate Similarity NPC36108
0.8209 Intermediate Similarity NPC246974
0.8209 Intermediate Similarity NPC147247
0.8148 Intermediate Similarity NPC470706
0.814 Intermediate Similarity NPC268572
0.8125 Intermediate Similarity NPC321505
0.8125 Intermediate Similarity NPC283468
0.8125 Intermediate Similarity NPC115144
0.8125 Intermediate Similarity NPC277857
0.8125 Intermediate Similarity NPC179825
0.8125 Intermediate Similarity NPC191376
0.8088 Intermediate Similarity NPC329595
0.8088 Intermediate Similarity NPC326599
0.808 Intermediate Similarity NPC156840
0.808 Intermediate Similarity NPC8547
0.808 Intermediate Similarity NPC166837
0.808 Intermediate Similarity NPC78918
0.808 Intermediate Similarity NPC173746
0.808 Intermediate Similarity NPC257124
0.808 Intermediate Similarity NPC139617
0.8074 Intermediate Similarity NPC469977
0.8069 Intermediate Similarity NPC147390
0.8069 Intermediate Similarity NPC246587
0.8069 Intermediate Similarity NPC428
0.8069 Intermediate Similarity NPC135538
0.8069 Intermediate Similarity NPC476571
0.8069 Intermediate Similarity NPC24233
0.8067 Intermediate Similarity NPC329837
0.8062 Intermediate Similarity NPC122009
0.8014 Intermediate Similarity NPC103379
0.8014 Intermediate Similarity NPC477565
0.8014 Intermediate Similarity NPC477838
0.8014 Intermediate Similarity NPC477837
0.8 Intermediate Similarity NPC310338
0.8 Intermediate Similarity NPC43275
0.8 Intermediate Similarity NPC281298
0.7986 Intermediate Similarity NPC185838
0.7984 Intermediate Similarity NPC164386
0.7984 Intermediate Similarity NPC120075
0.7945 Intermediate Similarity NPC470935
0.7945 Intermediate Similarity NPC153644
0.7945 Intermediate Similarity NPC471032
0.7943 Intermediate Similarity NPC231572
0.7939 Intermediate Similarity NPC165133
0.7939 Intermediate Similarity NPC242885
0.7939 Intermediate Similarity NPC232316
0.7939 Intermediate Similarity NPC227217
0.7939 Intermediate Similarity NPC117780
0.7939 Intermediate Similarity NPC56214
0.7939 Intermediate Similarity NPC95614
0.7923 Intermediate Similarity NPC470626
0.7917 Intermediate Similarity NPC294249
0.7914 Intermediate Similarity NPC473463
0.7905 Intermediate Similarity NPC277669
0.7905 Intermediate Similarity NPC127402
0.7905 Intermediate Similarity NPC76213
0.7895 Intermediate Similarity NPC298486
0.7883 Intermediate Similarity NPC160193
0.7879 Intermediate Similarity NPC183262
0.7879 Intermediate Similarity NPC83279
0.7877 Intermediate Similarity NPC476151
0.7872 Intermediate Similarity NPC254610
0.7872 Intermediate Similarity NPC193528
0.7863 Intermediate Similarity NPC311595
0.7863 Intermediate Similarity NPC24474
0.7852 Intermediate Similarity NPC133011
0.7852 Intermediate Similarity NPC82285
0.7846 Intermediate Similarity NPC293619
0.7838 Intermediate Similarity NPC220858
0.7838 Intermediate Similarity NPC97221
0.7838 Intermediate Similarity NPC151895
0.7838 Intermediate Similarity NPC192768
0.7838 Intermediate Similarity NPC88249
0.7823 Intermediate Similarity NPC231705
0.7821 Intermediate Similarity NPC66573
0.782 Intermediate Similarity NPC38996
0.782 Intermediate Similarity NPC160380
0.7803 Intermediate Similarity NPC263835
0.78 Intermediate Similarity NPC477564
0.78 Intermediate Similarity NPC2295
0.7795 Intermediate Similarity NPC195873
0.7786 Intermediate Similarity NPC284855
0.7786 Intermediate Similarity NPC282477
0.777 Intermediate Similarity NPC207824
0.777 Intermediate Similarity NPC60538
0.7769 Intermediate Similarity NPC221049
0.7761 Intermediate Similarity NPC85488
0.776 Intermediate Similarity NPC227894
0.7748 Intermediate Similarity NPC295691
0.7748 Intermediate Similarity NPC2413
0.7748 Intermediate Similarity NPC127674
0.7748 Intermediate Similarity NPC189266
0.7748 Intermediate Similarity NPC184026
0.7748 Intermediate Similarity NPC5238
0.7748 Intermediate Similarity NPC204828
0.7748 Intermediate Similarity NPC193949
0.7748 Intermediate Similarity NPC249797
0.7748 Intermediate Similarity NPC278799
0.7748 Intermediate Similarity NPC39701
0.7748 Intermediate Similarity NPC110416
0.7748 Intermediate Similarity NPC107602
0.7748 Intermediate Similarity NPC207757
0.7748 Intermediate Similarity NPC276588
0.7748 Intermediate Similarity NPC54379
0.7748 Intermediate Similarity NPC172765
0.7748 Intermediate Similarity NPC469817
0.7744 Intermediate Similarity NPC269843
0.7744 Intermediate Similarity NPC60962
0.7744 Intermediate Similarity NPC158949
0.7744 Intermediate Similarity NPC14007
0.7744 Intermediate Similarity NPC224814
0.7744 Intermediate Similarity NPC207613
0.7744 Intermediate Similarity NPC189844
0.7744 Intermediate Similarity NPC109083
0.7734 Intermediate Similarity NPC165646
0.7717 Intermediate Similarity NPC137685
0.7717 Intermediate Similarity NPC474149
0.771 Intermediate Similarity NPC259638
0.771 Intermediate Similarity NPC86947
0.771 Intermediate Similarity NPC39793
0.7708 Intermediate Similarity NPC275150
0.7704 Intermediate Similarity NPC280704
0.7704 Intermediate Similarity NPC317769
0.7704 Intermediate Similarity NPC31344
0.7698 Intermediate Similarity NPC476570
0.7697 Intermediate Similarity NPC147091
0.7692 Intermediate Similarity NPC303370
0.7687 Intermediate Similarity NPC324571
0.7687 Intermediate Similarity NPC343720
0.7687 Intermediate Similarity NPC54872
0.7687 Intermediate Similarity NPC211992
0.7687 Intermediate Similarity NPC476343
0.7687 Intermediate Similarity NPC70752
0.7687 Intermediate Similarity NPC262156
0.7687 Intermediate Similarity NPC473853
0.7687 Intermediate Similarity NPC312675
0.7687 Intermediate Similarity NPC184651
0.7687 Intermediate Similarity NPC201777
0.7687 Intermediate Similarity NPC113865
0.7687 Intermediate Similarity NPC470212

  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 NPC308885 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
1.0 High Similarity NPD3145 Approved
1.0 High Similarity NPD3144 Approved
0.976 High Similarity NPD2674 Phase 3
0.8613 High Similarity NPD7153 Discontinued
0.8467 Intermediate Similarity NPD2161 Phase 2
0.8125 Intermediate Similarity NPD4123 Phase 3
0.8099 Intermediate Similarity NPD6331 Phase 2
0.808 Intermediate Similarity NPD228 Approved
0.803 Intermediate Similarity NPD2337 Clinical (unspecified phase)
0.797 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7852 Intermediate Similarity NPD4675 Approved
0.7852 Intermediate Similarity NPD4678 Approved
0.7785 Intermediate Similarity NPD824 Approved
0.7755 Intermediate Similarity NPD4739 Approved
0.7704 Intermediate Similarity NPD1669 Approved
0.7703 Intermediate Similarity NPD7526 Approved
0.7703 Intermediate Similarity NPD52 Approved
0.7703 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7681 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7655 Intermediate Similarity NPD3060 Approved
0.7647 Intermediate Similarity NPD2922 Phase 1
0.7639 Intermediate Similarity NPD3656 Approved
0.7603 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD9377 Approved
0.7597 Intermediate Similarity NPD9379 Approved
0.7586 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD5718 Phase 2
0.7564 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7537 Intermediate Similarity NPD2667 Approved
0.7537 Intermediate Similarity NPD2668 Approved
0.7532 Intermediate Similarity NPD4083 Discontinued
0.7518 Intermediate Similarity NPD839 Approved
0.7518 Intermediate Similarity NPD840 Approved
0.7517 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD1375 Discontinued
0.75 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD2157 Approved
0.7482 Intermediate Similarity NPD1712 Approved
0.7468 Intermediate Similarity NPD5772 Approved
0.7468 Intermediate Similarity NPD5773 Approved
0.7467 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD1558 Phase 1
0.745 Intermediate Similarity NPD4357 Discontinued
0.7436 Intermediate Similarity NPD7833 Phase 2
0.7436 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD4055 Discovery
0.7436 Intermediate Similarity NPD5604 Discontinued
0.7436 Intermediate Similarity NPD7831 Phase 2
0.7432 Intermediate Similarity NPD5241 Discontinued
0.7431 Intermediate Similarity NPD6895 Approved
0.7431 Intermediate Similarity NPD6896 Approved
0.7417 Intermediate Similarity NPD2122 Discontinued
0.7415 Intermediate Similarity NPD4162 Approved
0.7415 Intermediate Similarity NPD5177 Phase 3
0.7405 Intermediate Similarity NPD5283 Phase 1
0.7394 Intermediate Similarity NPD7477 Discontinued
0.7372 Intermediate Similarity NPD2230 Approved
0.7372 Intermediate Similarity NPD2232 Approved
0.7372 Intermediate Similarity NPD2233 Approved
0.7361 Intermediate Similarity NPD2653 Approved
0.7338 Intermediate Similarity NPD3055 Approved
0.7338 Intermediate Similarity NPD3053 Approved
0.7338 Intermediate Similarity NPD4772 Phase 2
0.7338 Intermediate Similarity NPD4773 Phase 2
0.7333 Intermediate Similarity NPD1357 Approved
0.7328 Intermediate Similarity NPD821 Approved
0.7325 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD5109 Approved
0.7324 Intermediate Similarity NPD5111 Phase 2
0.7324 Intermediate Similarity NPD5110 Phase 2
0.732 Intermediate Similarity NPD4005 Discontinued
0.7315 Intermediate Similarity NPD2219 Phase 1
0.7308 Intermediate Similarity NPD2560 Approved
0.7308 Intermediate Similarity NPD2563 Approved
0.7285 Intermediate Similarity NPD4584 Approved
0.7279 Intermediate Similarity NPD9384 Approved
0.7279 Intermediate Similarity NPD9381 Approved
0.7273 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD2898 Approved
0.7266 Intermediate Similarity NPD5311 Approved
0.7266 Intermediate Similarity NPD5310 Approved
0.726 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD3693 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD3027 Phase 3
0.7254 Intermediate Similarity NPD1024 Discontinued
0.725 Intermediate Similarity NPD4606 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD4010 Discontinued
0.7244 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD2977 Approved
0.7244 Intermediate Similarity NPD2978 Approved
0.723 Intermediate Similarity NPD1044 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD9622 Approved
0.719 Intermediate Similarity NPD6031 Approved
0.719 Intermediate Similarity NPD3640 Phase 3
0.719 Intermediate Similarity NPD6030 Approved
0.719 Intermediate Similarity NPD3641 Approved
0.719 Intermediate Similarity NPD3639 Approved
0.7181 Intermediate Similarity NPD2460 Phase 3
0.7181 Intermediate Similarity NPD4236 Phase 3
0.7181 Intermediate Similarity NPD4237 Approved
0.7181 Intermediate Similarity NPD2458 Approved
0.7181 Intermediate Similarity NPD2459 Approved
0.7179 Intermediate Similarity NPD5720 Discontinued
0.7171 Intermediate Similarity NPD1771 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD1424 Approved
0.7163 Intermediate Similarity NPD9620 Approved
0.7163 Intermediate Similarity NPD9619 Approved
0.7163 Intermediate Similarity NPD9621 Approved
0.7163 Intermediate Similarity NPD6584 Phase 3
0.7154 Intermediate Similarity NPD9296 Approved
0.7143 Intermediate Similarity NPD3686 Approved
0.7143 Intermediate Similarity NPD3687 Approved
0.7143 Intermediate Similarity NPD4108 Discontinued
0.7143 Intermediate Similarity NPD9634 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD4186 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD2492 Phase 1
0.7122 Intermediate Similarity NPD2235 Phase 2
0.7122 Intermediate Similarity NPD2231 Phase 2
0.7115 Intermediate Similarity NPD5090 Approved
0.7115 Intermediate Similarity NPD5089 Approved
0.7114 Intermediate Similarity NPD3655 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD2040 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD9494 Approved
0.7103 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD2238 Phase 2
0.7103 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD3620 Phase 2
0.7099 Intermediate Similarity NPD3022 Approved
0.7099 Intermediate Similarity NPD3021 Approved
0.7097 Intermediate Similarity NPD4017 Approved
0.7095 Intermediate Similarity NPD3156 Discontinued
0.7086 Intermediate Similarity NPD3692 Discontinued
0.7086 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD302 Approved
0.7083 Intermediate Similarity NPD597 Approved
0.7083 Intermediate Similarity NPD601 Approved
0.7083 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD598 Approved
0.7081 Intermediate Similarity NPD2821 Approved
0.7075 Intermediate Similarity NPD6111 Discontinued
0.7071 Intermediate Similarity NPD3685 Discontinued
0.7071 Intermediate Similarity NPD1420 Approved
0.7071 Intermediate Similarity NPD1421 Approved
0.7071 Intermediate Similarity NPD4129 Approved
0.707 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD596 Approved
0.7063 Intermediate Similarity NPD600 Approved
0.7059 Intermediate Similarity NPD5536 Phase 2
0.7055 Intermediate Similarity NPD27 Approved
0.7055 Intermediate Similarity NPD2489 Approved
0.7051 Intermediate Similarity NPD5617 Suspended
0.7047 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD7124 Phase 2
0.7037 Intermediate Similarity NPD6071 Discontinued
0.7034 Intermediate Similarity NPD1132 Approved
0.7034 Intermediate Similarity NPD1423 Approved
0.7034 Intermediate Similarity NPD1130 Approved
0.7034 Intermediate Similarity NPD1136 Approved
0.7032 Intermediate Similarity NPD2883 Discontinued
0.7032 Intermediate Similarity NPD5267 Discontinued
0.7025 Intermediate Similarity NPD5563 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD2684 Approved
0.7018 Intermediate Similarity NPD6377 Clinical (unspecified phase)
0.7015 Intermediate Similarity NPD2234 Approved
0.7015 Intermediate Similarity NPD2228 Approved
0.7015 Intermediate Similarity NPD2229 Approved
0.7007 Intermediate Similarity NPD1772 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1444 Approved
0.7 Intermediate Similarity NPD1445 Approved
0.6987 Remote Similarity NPD3111 Phase 1
0.6986 Remote Similarity NPD3059 Approved
0.6986 Remote Similarity NPD3062 Approved
0.6986 Remote Similarity NPD3061 Approved
0.698 Remote Similarity NPD1632 Clinical (unspecified phase)
0.6974 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6972 Remote Similarity NPD3568 Approved
0.6972 Remote Similarity NPD3567 Approved
0.6966 Remote Similarity NPD1039 Discontinued
0.6962 Remote Similarity NPD7298 Approved
0.6957 Remote Similarity NPD2594 Approved
0.6957 Remote Similarity NPD2595 Approved
0.6954 Remote Similarity NPD44 Approved
0.6954 Remote Similarity NPD6364 Approved
0.6951 Remote Similarity NPD677 Clinical (unspecified phase)
0.695 Remote Similarity NPD6583 Phase 3
0.695 Remote Similarity NPD6582 Phase 2
0.6943 Remote Similarity NPD3296 Phase 1
0.6943 Remote Similarity NPD6502 Phase 2
0.6929 Remote Similarity NPD776 Approved
0.6928 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6923 Remote Similarity NPD950 Clinical (unspecified phase)
0.6918 Remote Similarity NPD259 Phase 1
0.6913 Remote Similarity NPD6380 Phase 1

  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