Structure

Physi-Chem Properties

Molecular Weight:  232.06
Volume:  240.826
LogP:  2.391
LogD:  2.378
LogS:  -4.323
# Rotatable Bonds:  0
TPSA:  42.85
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.468
Synthetic Accessibility Score:  2.283
Fsp3:  0.0
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:  -4.758
MDCK Permeability:  2.2938609617995098e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.046
30% Bioavailability (F30%):  0.159

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.829
Plasma Protein Binding (PPB):  95.39055633544922%
Volume Distribution (VD):  1.487
Pgp-substrate:  3.1320340633392334%

ADMET: Metabolism

CYP1A2-inhibitor:  0.963
CYP1A2-substrate:  0.154
CYP2C19-inhibitor:  0.516
CYP2C19-substrate:  0.074
CYP2C9-inhibitor:  0.313
CYP2C9-substrate:  0.75
CYP2D6-inhibitor:  0.068
CYP2D6-substrate:  0.707
CYP3A4-inhibitor:  0.357
CYP3A4-substrate:  0.141

ADMET: Excretion

Clearance (CL):  2.437
Half-life (T1/2):  0.116

ADMET: Toxicity

hERG Blockers:  0.089
Human Hepatotoxicity (H-HT):  0.781
Drug-inuced Liver Injury (DILI):  0.965
AMES Toxicity:  0.941
Rat Oral Acute Toxicity:  0.361
Maximum Recommended Daily Dose:  0.373
Skin Sensitization:  0.332
Carcinogencity:  0.758
Eye Corrosion:  0.004
Eye Irritation:  0.966
Respiratory Toxicity:  0.962

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

  Natural Product: NPC237188

Natural Product ID:  NPC237188
Common Name*:   Sampangine
IUPAC Name:   n.a.
Synonyms:   Sampangine
Standard InCHIKey:  BWQKHOMAOVUASZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H8N2O/c18-15-11-4-2-1-3-10(11)13-12-9(5-7-16-13)6-8-17-14(12)15/h1-8H
SMILES:  c1ccc2c(-c3c4c(ccn3)ccnc4C2=O)c1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL435201
PubChem CID:   387195
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0003019] 1-azaoxoaporphines

*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
NPO2884 Annona squamosa Species Annonaceae Eukaryota seeds n.a. n.a. PMID[11141125]
NPO12331 Duguetia hadrantha Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[11374943]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[12398544]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[18419154]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[19296389]
NPO13611 Ambavia gerrardii Species Annonaceae Eukaryota n.a. root n.a. PMID[21504145]
NPO13611 Ambavia gerrardii Species Annonaceae Eukaryota n.a. Madagascar Dry Forest n.a. PMID[21504145]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[21910504]
NPO2884 Annona squamosa Species Annonaceae Eukaryota seeds n.a. n.a. PMID[22011319]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. seed n.a. PMID[22011319]
NPO2884 Annona squamosa Species Annonaceae Eukaryota Barks n.a. n.a. PMID[2348205]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. fruit n.a. PMID[8786370]
NPO2884 Annona squamosa Species Annonaceae Eukaryota bark n.a. n.a. PMID[9214729]
NPO2884 Annona squamosa Species Annonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13611 Ambavia gerrardii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12331 Duguetia hadrantha Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2884 Annona squamosa Species Annonaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 2.0 ug.mL-1 PMID[510104]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 = 4.1 ug.mL-1 PMID[510104]
NPT457 Cell Line BT-549 Homo sapiens IC50 = 6.4 ug.mL-1 PMID[510104]
NPT91 Cell Line KB Homo sapiens IC50 = 5.3 ug.mL-1 PMID[510104]
NPT916 Cell Line SK-MEL Homo sapiens IC50 = 0.37 ug.mL-1 PMID[510104]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 580.0 nM PMID[510106]
NPT179 Cell Line A2780 Homo sapiens IC50 = 600.0 nM PMID[510106]
NPT396 Cell Line T47D Homo sapiens Activity = 48.0 % PMID[510109]
NPT396 Cell Line T47D Homo sapiens Activity = 46.0 % PMID[510109]
NPT396 Cell Line T47D Homo sapiens FC = 1.5 n.a. PMID[510109]
NPT396 Cell Line T47D Homo sapiens Activity = 50.0 % PMID[510109]
NPT20 Organism Candida albicans Candida albicans MIC = 1.56 ug.mL-1 PMID[510102]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 0.78 ug.mL-1 PMID[510102]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC = 1.56 ug.mL-1 PMID[510102]
NPT86 Organism Mycobacterium intracellulare Mycobacterium intracellulare MIC = 0.78 ug.mL-1 PMID[510102]
NPT29 Organism Rattus norvegicus Rattus norvegicus Stability = 13.0 % PMID[510103]
NPT29 Organism Rattus norvegicus Rattus norvegicus Stability = 33.0 % PMID[510103]
NPT20 Organism Candida albicans Candida albicans IZ = 10.0 mm PMID[510103]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IZ = 35.0 mm PMID[510103]
NPT20 Organism Candida albicans Candida albicans MIC = 3.12 ug.mL-1 PMID[510103]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 0.2 ug.mL-1 PMID[510103]
NPT2 Others Unspecified Ratio IC50 > 11.0 n.a. PMID[510104]
NPT2 Others Unspecified Ratio IC50 > 70.0 n.a. PMID[510104]
NPT2 Others Unspecified Ratio IC50 < 0.2 n.a. PMID[510104]
NPT2 Others Unspecified Ratio > 13.3 n.a. PMID[510104]
NPT3964 Protein Complex Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 Homo sapiens MIC < 0.15 ug.mL-1 PMID[510104]
NPT20 Organism Candida albicans Candida albicans MIC = 1.56 ug.mL-1 PMID[510104]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 12.5 ug.mL-1 PMID[510104]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 0.78 ug.mL-1 PMID[510104]
NPT20 Organism Candida albicans Candida albicans MIC = 0.39 ug.mL-1 PMID[510104]
NPT3964 Protein Complex Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[510104]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 9.0 ug.mL-1 PMID[510104]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 5.5 ug.mL-1 PMID[510104]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 = 0.15 ug.mL-1 PMID[510104]
NPT20 Organism Candida albicans Candida albicans IC50 = 0.15 ug.mL-1 PMID[510104]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.42 ug.mL-1 PMID[510104]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.068 ug.mL-1 PMID[510104]
NPT20 Organism Candida albicans Candida albicans MIC = 3.12 ug.mL-1 PMID[510105]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 0.2 ug.mL-1 PMID[510105]
NPT86 Organism Mycobacterium intracellulare Mycobacterium intracellulare MIC = 0.78 ug.mL-1 PMID[510107]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC80 = 16.0 ug.mL-1 PMID[510108]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC80 = 2.0 ug.mL-1 PMID[510108]
NPT20 Organism Candida albicans Candida albicans MIC80 = 0.5 ug.mL-1 PMID[510108]
NPT188 Organism Candida parapsilosis Candida parapsilosis MIC80 = 4.0 ug.mL-1 PMID[510108]
NPT554 Organism Candida glabrata Candida glabrata MIC80 = 0.125 ug.mL-1 PMID[510108]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MIC80 = 16.0 ug.mL-1 PMID[510108]
NPT327 Organism Microsporum gypseum Microsporum gypseum MIC80 > 64.0 ug.mL-1 PMID[510108]
NPT35 Others n.a. Solubility = 12.6 ug.mL-1 PMID[510108]
NPT188 Organism Candida parapsilosis Candida parapsilosis MIC80 = 4.0 ug.mL-1 PMID[510110]
NPT20 Organism Candida albicans Candida albicans MIC80 = 0.5 ug.mL-1 PMID[510110]
NPT554 Organism Candida glabrata Candida glabrata MIC80 = 0.125 ug.mL-1 PMID[510110]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC80 = 2.0 ug.mL-1 PMID[510110]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC80 = 16.0 ug.mL-1 PMID[510110]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MIC80 = 16.0 ug.mL-1 PMID[510110]
NPT327 Organism Microsporum gypseum Microsporum gypseum MIC80 > 64.0 ug.mL-1 PMID[510110]

☑ 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 NPC237188 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
0.9152 High Similarity NPC157583
0.8708 High Similarity NPC34837
0.8701 High Similarity NPC128244
0.8678 High Similarity NPC255909
0.8678 High Similarity NPC103119
0.8675 High Similarity NPC70949
0.8636 High Similarity NPC216550
0.8313 Intermediate Similarity NPC80681
0.8239 Intermediate Similarity NPC467063
0.8166 Intermediate Similarity NPC265100
0.8142 Intermediate Similarity NPC167710
0.8118 Intermediate Similarity NPC328318
0.8118 Intermediate Similarity NPC328596
0.8032 Intermediate Similarity NPC327592
0.802 Intermediate Similarity NPC216612
0.7989 Intermediate Similarity NPC317373
0.798 Intermediate Similarity NPC322482
0.7944 Intermediate Similarity NPC118084
0.7921 Intermediate Similarity NPC191415
0.788 Intermediate Similarity NPC326422
0.7853 Intermediate Similarity NPC284775
0.7846 Intermediate Similarity NPC237740
0.7826 Intermediate Similarity NPC272458
0.7798 Intermediate Similarity NPC70406
0.7778 Intermediate Similarity NPC169433
0.7759 Intermediate Similarity NPC56233
0.7744 Intermediate Similarity NPC318299
0.7738 Intermediate Similarity NPC473878
0.7737 Intermediate Similarity NPC106757
0.7711 Intermediate Similarity NPC86288
0.7704 Intermediate Similarity NPC317752
0.7692 Intermediate Similarity NPC217021
0.7692 Intermediate Similarity NPC470679
0.7688 Intermediate Similarity NPC304203
0.768 Intermediate Similarity NPC102755
0.7656 Intermediate Similarity NPC88115
0.7617 Intermediate Similarity NPC472064
0.7617 Intermediate Similarity NPC472065
0.7586 Intermediate Similarity NPC242116
0.7584 Intermediate Similarity NPC252572
0.7581 Intermediate Similarity NPC476460
0.7569 Intermediate Similarity NPC73994
0.7566 Intermediate Similarity NPC106824
0.7544 Intermediate Similarity NPC251391
0.7544 Intermediate Similarity NPC138842
0.7542 Intermediate Similarity NPC139763
0.7542 Intermediate Similarity NPC293216
0.7541 Intermediate Similarity NPC477003
0.7528 Intermediate Similarity NPC201634
0.75 Intermediate Similarity NPC251722
0.75 Intermediate Similarity NPC314102
0.75 Intermediate Similarity NPC467188
0.7487 Intermediate Similarity NPC284338
0.7487 Intermediate Similarity NPC81535
0.7471 Intermediate Similarity NPC474492
0.7471 Intermediate Similarity NPC293487
0.7458 Intermediate Similarity NPC114637
0.7447 Intermediate Similarity NPC47190
0.7429 Intermediate Similarity NPC470680
0.7429 Intermediate Similarity NPC100104
0.7427 Intermediate Similarity NPC313889
0.7423 Intermediate Similarity NPC317701
0.7412 Intermediate Similarity NPC105811
0.7412 Intermediate Similarity NPC100726
0.7401 Intermediate Similarity NPC42372
0.7377 Intermediate Similarity NPC477042
0.7374 Intermediate Similarity NPC470020
0.7371 Intermediate Similarity NPC472063
0.7371 Intermediate Similarity NPC472062
0.7371 Intermediate Similarity NPC472069
0.7368 Intermediate Similarity NPC123906
0.7345 Intermediate Similarity NPC478184
0.7345 Intermediate Similarity NPC478182
0.7337 Intermediate Similarity NPC470677
0.7333 Intermediate Similarity NPC262338
0.733 Intermediate Similarity NPC215584
0.733 Intermediate Similarity NPC44773
0.7326 Intermediate Similarity NPC471655
0.7306 Intermediate Similarity NPC237414
0.7303 Intermediate Similarity NPC115232
0.7288 Intermediate Similarity NPC478185
0.7268 Intermediate Similarity NPC83774
0.7263 Intermediate Similarity NPC478183
0.7257 Intermediate Similarity NPC51054
0.7256 Intermediate Similarity NPC72905
0.7253 Intermediate Similarity NPC297034
0.7249 Intermediate Similarity NPC324091
0.7239 Intermediate Similarity NPC282398
0.7233 Intermediate Similarity NPC46358
0.7225 Intermediate Similarity NPC40070
0.7222 Intermediate Similarity NPC313823
0.7222 Intermediate Similarity NPC142385
0.7219 Intermediate Similarity NPC133003
0.7213 Intermediate Similarity NPC151635
0.7207 Intermediate Similarity NPC71132
0.7204 Intermediate Similarity NPC470205
0.72 Intermediate Similarity NPC209362
0.7189 Intermediate Similarity NPC61011
0.7189 Intermediate Similarity NPC471997
0.7186 Intermediate Similarity NPC116555
0.7182 Intermediate Similarity NPC32534
0.7181 Intermediate Similarity NPC17273
0.7181 Intermediate Similarity NPC141612
0.7181 Intermediate Similarity NPC135601
0.7175 Intermediate Similarity NPC56765
0.7165 Intermediate Similarity NPC474916
0.7158 Intermediate Similarity NPC469529
0.7151 Intermediate Similarity NPC21174
0.7151 Intermediate Similarity NPC271797
0.715 Intermediate Similarity NPC472070
0.7143 Intermediate Similarity NPC200743
0.7128 Intermediate Similarity NPC474767
0.7128 Intermediate Similarity NPC308931
0.7128 Intermediate Similarity NPC99939
0.7119 Intermediate Similarity NPC76982
0.7119 Intermediate Similarity NPC213914
0.7107 Intermediate Similarity NPC57398
0.7104 Intermediate Similarity NPC477976
0.7102 Intermediate Similarity NPC229055
0.7097 Intermediate Similarity NPC79777
0.7095 Intermediate Similarity NPC194881
0.7092 Intermediate Similarity NPC121327
0.7088 Intermediate Similarity NPC91895
0.7086 Intermediate Similarity NPC472260
0.7083 Intermediate Similarity NPC65408
0.7074 Intermediate Similarity NPC21429
0.7074 Intermediate Similarity NPC46895
0.7074 Intermediate Similarity NPC207851
0.7073 Intermediate Similarity NPC267811
0.7073 Intermediate Similarity NPC469727
0.7072 Intermediate Similarity NPC41717
0.7067 Intermediate Similarity NPC210434
0.7062 Intermediate Similarity NPC74357
0.7062 Intermediate Similarity NPC472116
0.7056 Intermediate Similarity NPC274981
0.7048 Intermediate Similarity NPC470018
0.7045 Intermediate Similarity NPC281094
0.7043 Intermediate Similarity NPC12649
0.7041 Intermediate Similarity NPC477004
0.7027 Intermediate Similarity NPC137353
0.7026 Intermediate Similarity NPC227582
0.7025 Intermediate Similarity NPC143603
0.7025 Intermediate Similarity NPC91958
0.702 Intermediate Similarity NPC143977
0.7014 Intermediate Similarity NPC74575
0.7011 Intermediate Similarity NPC477974
0.7011 Intermediate Similarity NPC470111
0.701 Intermediate Similarity NPC195239
0.701 Intermediate Similarity NPC157828
0.7005 Intermediate Similarity NPC24864
0.7005 Intermediate Similarity NPC182940
0.7005 Intermediate Similarity NPC234403
0.6995 Remote Similarity NPC471943
0.699 Remote Similarity NPC27041
0.6989 Remote Similarity NPC470233
0.6988 Remote Similarity NPC256893
0.6983 Remote Similarity NPC206819
0.6983 Remote Similarity NPC318065
0.6979 Remote Similarity NPC154339
0.6974 Remote Similarity NPC102592
0.6974 Remote Similarity NPC11445
0.6974 Remote Similarity NPC79356
0.6971 Remote Similarity NPC102664
0.6963 Remote Similarity NPC206186
0.6961 Remote Similarity NPC317105
0.6961 Remote Similarity NPC470702
0.6961 Remote Similarity NPC473218
0.6961 Remote Similarity NPC477413
0.6954 Remote Similarity NPC74413
0.6954 Remote Similarity NPC63545
0.6949 Remote Similarity NPC325903
0.6947 Remote Similarity NPC282103
0.6931 Remote Similarity NPC159125
0.6931 Remote Similarity NPC117027
0.6927 Remote Similarity NPC470703
0.6927 Remote Similarity NPC193740
0.6927 Remote Similarity NPC167635
0.6927 Remote Similarity NPC286427
0.6919 Remote Similarity NPC252338
0.6918 Remote Similarity NPC54102
0.6918 Remote Similarity NPC162689
0.6916 Remote Similarity NPC477112
0.6915 Remote Similarity NPC175602
0.6914 Remote Similarity NPC201380
0.6914 Remote Similarity NPC179787
0.6914 Remote Similarity NPC469811
0.6911 Remote Similarity NPC62749
0.6907 Remote Similarity NPC471386
0.6902 Remote Similarity NPC194411
0.6895 Remote Similarity NPC110158
0.6895 Remote Similarity NPC258480
0.6891 Remote Similarity NPC268966
0.6889 Remote Similarity NPC41257
0.6884 Remote Similarity NPC49547
0.6882 Remote Similarity NPC105127
0.6879 Remote Similarity NPC190296
0.6875 Remote Similarity NPC23476
0.6875 Remote Similarity NPC321911
0.6875 Remote Similarity NPC477415
0.6875 Remote Similarity NPC474259

  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 NPC237188 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
0.8284 Intermediate Similarity NPD6446 Discontinued
0.8034 Intermediate Similarity NPD7564 Discontinued
0.8033 Intermediate Similarity NPD7024 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD1270 Approved
0.7895 Intermediate Similarity NPD5400 Approved
0.7865 Intermediate Similarity NPD2481 Approved
0.7865 Intermediate Similarity NPD2479 Phase 3
0.7836 Intermediate Similarity NPD6454 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD1292 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD5473 Discontinued
0.7753 Intermediate Similarity NPD2753 Discontinued
0.7714 Intermediate Similarity NPD1343 Approved
0.7697 Intermediate Similarity NPD3238 Discontinued
0.7641 Intermediate Similarity NPD4051 Discontinued
0.7619 Intermediate Similarity NPD7204 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD4988 Discontinued
0.7602 Intermediate Similarity NPD4614 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD7401 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD1291 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD5809 Phase 3
0.7554 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD3583 Phase 2
0.7515 Intermediate Similarity NPD4547 Phase 3
0.75 Intermediate Similarity NPD4385 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD7207 Approved
0.7474 Intermediate Similarity NPD7209 Approved
0.7474 Intermediate Similarity NPD7208 Approved
0.7474 Intermediate Similarity NPD5446 Phase 2
0.7469 Intermediate Similarity NPD1627 Clinical (unspecified phase)
0.7461 Intermediate Similarity NPD4924 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD4643 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD4011 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD6180 Clinical (unspecified phase)
0.7387 Intermediate Similarity NPD6954 Phase 2
0.7384 Intermediate Similarity NPD5965 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD6204 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD8248 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD6178 Phase 3
0.735 Intermediate Similarity NPD5888 Phase 2
0.7337 Intermediate Similarity NPD1918 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD6152 Phase 1
0.733 Intermediate Similarity NPD4848 Phase 1
0.733 Intermediate Similarity NPD1851 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD3942 Approved
0.7317 Intermediate Similarity NPD3944 Approved
0.7303 Intermediate Similarity NPD2720 Phase 1
0.7303 Intermediate Similarity NPD2719 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD1853 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6459 Phase 2
0.7273 Intermediate Similarity NPD5820 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD5505 Discontinued
0.7247 Intermediate Similarity NPD3323 Discontinued
0.724 Intermediate Similarity NPD7027 Phase 3
0.7236 Intermediate Similarity NPD2295 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD3905 Phase 3
0.7216 Intermediate Similarity NPD6137 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD6471 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD2336 Approved
0.7194 Intermediate Similarity NPD7187 Phase 2
0.7191 Intermediate Similarity NPD6771 Discontinued
0.7178 Intermediate Similarity NPD6787 Phase 2
0.7176 Intermediate Similarity NPD2006 Phase 2
0.7173 Intermediate Similarity NPD4922 Phase 2
0.7172 Intermediate Similarity NPD5491 Phase 3
0.7172 Intermediate Similarity NPD5489 Phase 1
0.7172 Intermediate Similarity NPD7010 Phase 3
0.7168 Intermediate Similarity NPD2430 Phase 2
0.7158 Intermediate Similarity NPD4883 Approved
0.7158 Intermediate Similarity NPD1905 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD7469 Discontinued
0.7143 Intermediate Similarity NPD180 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2837 Discontinued
0.7134 Intermediate Similarity NPD715 Phase 3
0.7129 Intermediate Similarity NPD7455 Approved
0.7129 Intermediate Similarity NPD7454 Approved
0.7128 Intermediate Similarity NPD4336 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD1254 Approved
0.7126 Intermediate Similarity NPD1256 Approved
0.7126 Intermediate Similarity NPD1253 Approved
0.7126 Intermediate Similarity NPD1255 Approved
0.7121 Intermediate Similarity NPD6987 Phase 1
0.712 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD4075 Phase 2
0.7113 Intermediate Similarity NPD6664 Approved
0.7112 Intermediate Similarity NPD3318 Approved
0.7112 Intermediate Similarity NPD3319 Phase 1
0.7112 Intermediate Similarity NPD3320 Approved
0.7107 Intermediate Similarity NPD2879 Approved
0.7107 Intermediate Similarity NPD2881 Approved
0.7105 Intermediate Similarity NPD7234 Approved
0.7105 Intermediate Similarity NPD7233 Approved
0.7105 Intermediate Similarity NPD7175 Phase 1
0.7095 Intermediate Similarity NPD5315 Discontinued
0.7083 Intermediate Similarity NPD201 Phase 2
0.7083 Intermediate Similarity NPD200 Phase 2
0.7073 Intermediate Similarity NPD8000 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD947 Approved
0.7062 Intermediate Similarity NPD2307 Discontinued
0.7062 Intermediate Similarity NPD7023 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD2118 Approved
0.7055 Intermediate Similarity NPD991 Phase 2
0.7055 Intermediate Similarity NPD992 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD2119 Approved
0.7053 Intermediate Similarity NPD7394 Phase 2
0.705 Intermediate Similarity NPD1506 Discontinued
0.7044 Intermediate Similarity NPD7195 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD2405 Phase 3
0.7037 Intermediate Similarity NPD5555 Phase 1
0.7035 Intermediate Similarity NPD6288 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD3393 Approved
0.7024 Intermediate Similarity NPD3394 Approved
0.7024 Intermediate Similarity NPD3389 Approved
0.7017 Intermediate Similarity NPD1568 Clinical (unspecified phase)
0.7015 Intermediate Similarity NPD7191 Phase 2
0.7015 Intermediate Similarity NPD7665 Phase 2
0.7015 Intermediate Similarity NPD7666 Phase 3
0.701 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD7406 Phase 2
0.7006 Intermediate Similarity NPD977 Approved
0.7006 Intermediate Similarity NPD975 Approved
0.7006 Intermediate Similarity NPD4029 Approved
0.7006 Intermediate Similarity NPD4030 Approved
0.7006 Intermediate Similarity NPD976 Approved
0.7006 Intermediate Similarity NPD4028 Approved
0.7006 Intermediate Similarity NPD3385 Approved
0.7005 Intermediate Similarity NPD7404 Approved
0.7005 Intermediate Similarity NPD6479 Discontinued
0.7005 Intermediate Similarity NPD3927 Phase 2
0.6995 Remote Similarity NPD7927 Clinical (unspecified phase)
0.6995 Remote Similarity NPD5475 Discontinued
0.6985 Remote Similarity NPD4304 Discovery
0.6983 Remote Similarity NPD1630 Approved
0.6966 Remote Similarity NPD2748 Clinical (unspecified phase)
0.6964 Remote Similarity NPD272 Approved
0.6963 Remote Similarity NPD3961 Discontinued
0.6963 Remote Similarity NPD2770 Discontinued
0.6963 Remote Similarity NPD6507 Clinical (unspecified phase)
0.6954 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6954 Remote Similarity NPD6999 Discontinued
0.6952 Remote Similarity NPD3078 Approved
0.6952 Remote Similarity NPD3077 Approved
0.6952 Remote Similarity NPD3079 Approved
0.6952 Remote Similarity NPD3076 Approved
0.695 Remote Similarity NPD8115 Approved
0.695 Remote Similarity NPD8114 Approved
0.695 Remote Similarity NPD3247 Clinical (unspecified phase)
0.6949 Remote Similarity NPD2012 Clinical (unspecified phase)
0.6947 Remote Similarity NPD4298 Clinical (unspecified phase)
0.6943 Remote Similarity NPD7434 Approved
0.6942 Remote Similarity NPD4851 Clinical (unspecified phase)
0.6941 Remote Similarity NPD2896 Discontinued
0.694 Remote Similarity NPD4640 Approved
0.694 Remote Similarity NPD5862 Discovery
0.694 Remote Similarity NPD4639 Approved
0.694 Remote Similarity NPD4638 Approved
0.6935 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6931 Remote Similarity NPD6474 Phase 2
0.6928 Remote Similarity NPD3475 Approved
0.6928 Remote Similarity NPD3476 Approved
0.6927 Remote Similarity NPD4326 Phase 2
0.6927 Remote Similarity NPD3794 Approved
0.6927 Remote Similarity NPD3795 Approved
0.6927 Remote Similarity NPD6497 Approved
0.6923 Remote Similarity NPD5853 Phase 3
0.6923 Remote Similarity NPD5855 Phase 3
0.6919 Remote Similarity NPD1722 Approved
0.6919 Remote Similarity NPD4524 Discontinued
0.6911 Remote Similarity NPD7026 Phase 2
0.691 Remote Similarity NPD6285 Phase 2
0.6906 Remote Similarity NPD4384 Clinical (unspecified phase)
0.6904 Remote Similarity NPD1982 Phase 1
0.6898 Remote Similarity NPD4181 Approved
0.6893 Remote Similarity NPD6481 Clinical (unspecified phase)
0.6891 Remote Similarity NPD6281 Approved
0.6886 Remote Similarity NPD1251 Discontinued
0.6884 Remote Similarity NPD5017 Discontinued
0.6881 Remote Similarity NPD3839 Phase 2
0.6881 Remote Similarity NPD3840 Phase 2
0.6881 Remote Similarity NPD6838 Clinical (unspecified phase)
0.6878 Remote Similarity NPD2411 Approved
0.6875 Remote Similarity NPD3486 Clinical (unspecified phase)
0.6872 Remote Similarity NPD7661 Clinical (unspecified phase)
0.6872 Remote Similarity NPD3222 Phase 2
0.6868 Remote Similarity NPD1631 Approved
0.6866 Remote Similarity NPD5901 Discontinued
0.6866 Remote Similarity NPD6986 Phase 1
0.6865 Remote Similarity NPD3609 Approved
0.6865 Remote Similarity NPD3610 Approved
0.6865 Remote Similarity NPD5934 Clinical (unspecified phase)
0.6863 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6862 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6856 Remote Similarity NPD1658 Discontinued
0.6852 Remote Similarity NPD5040 Clinical (unspecified phase)
0.6842 Remote Similarity NPD7203 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5728 Clinical (unspecified phase)
0.6837 Remote Similarity NPD7619 Phase 3
0.6837 Remote Similarity NPD7618 Phase 3

  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