Structure

Physi-Chem Properties

Molecular Weight:  236.06
Volume:  234.957
LogP:  1.608
LogD:  1.666
LogS:  -4.044
# Rotatable Bonds:  0
TPSA:  54.34
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.505
Synthetic Accessibility Score:  2.861
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:  -4.826
MDCK Permeability:  1.6898440662771463e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.014
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.031
30% Bioavailability (F30%):  0.91

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.941
Plasma Protein Binding (PPB):  78.76586151123047%
Volume Distribution (VD):  0.908
Pgp-substrate:  9.566969871520996%

ADMET: Metabolism

CYP1A2-inhibitor:  0.989
CYP1A2-substrate:  0.651
CYP2C19-inhibitor:  0.679
CYP2C19-substrate:  0.15
CYP2C9-inhibitor:  0.371
CYP2C9-substrate:  0.878
CYP2D6-inhibitor:  0.298
CYP2D6-substrate:  0.69
CYP3A4-inhibitor:  0.396
CYP3A4-substrate:  0.155

ADMET: Excretion

Clearance (CL):  4.175
Half-life (T1/2):  0.821

ADMET: Toxicity

hERG Blockers:  0.018
Human Hepatotoxicity (H-HT):  0.164
Drug-inuced Liver Injury (DILI):  0.404
AMES Toxicity:  0.933
Rat Oral Acute Toxicity:  0.077
Maximum Recommended Daily Dose:  0.921
Skin Sensitization:  0.47
Carcinogencity:  0.976
Eye Corrosion:  0.006
Eye Irritation:  0.765
Respiratory Toxicity:  0.849

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  Natural Product: NPC200836

Natural Product ID:  NPC200836
Common Name*:   KXFAUPPCQVBDBN-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  KXFAUPPCQVBDBN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H8N2O2/c17-11-3-1-2-10-13(11)8-6-7-15-9-4-5-12(18)16(10)14(8)9/h1-7,17H
SMILES:  Oc1cccc2c1c1ccnc3c1n2c(=O)cc3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL504142
PubChem CID:   NA
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0003805] Indolonaphthyridine alkaloids

*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
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. seed n.a. DOI[10.1016/0031-9422(96)00258-0]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S1383-5769(99)00023-9]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[10086989]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[12828478]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota Roots n.a. n.a. PMID[14575431]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[1512598]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota Seeds n.a. n.a. PMID[15165151]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. root n.a. PMID[15520511]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[15620254]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[15949825]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[1624939]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17027268]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota fruit Indonesia n.a. PMID[17896817]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. root n.a. PMID[1800638]
NPO15146 Myrica nana Species Myricaceae Eukaryota n.a. n.a. n.a. PMID[18723353]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. Vietnam n.a. PMID[19026551]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota roots n.a. n.a. PMID[19299148]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO11530 Heterosigma akashiwo Species Chattonellaceae Eukaryota n.a. n.a. n.a. PMID[19659728]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19715321]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19919052]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19931461]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota seeds n.a. n.a. PMID[20050684]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[2089121]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota Seeds n.a. n.a. PMID[22506620]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23403897]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[24467387]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota roots n.a. n.a. PMID[25066952]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[25905468]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[26522747]
NPO5401 Monanchora unguiculata Species Crambeidae Eukaryota n.a. n.a. n.a. PMID[28368118]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[29667820]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[3379416]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[3443857]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[3760882]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[3841557]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6481366]
NPO17253 Soulamea soulameoides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6619884]
NPO17253 Soulamea soulameoides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6736970]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[7288443]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[7561896]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[8133299]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. xylem n.a. PMID[8133299]
NPO211 Aplysina cauliformis Species Aplysinidae Eukaryota n.a. n.a. n.a. PMID[8350091]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[8691212]
NPO17253 Soulamea soulameoides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12089 Trifolium alexandrinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17253 Soulamea soulameoides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO893 Helichrysum sutherlandii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8220 Russula sardonia Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11072 Geigeria schinzii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14150 Solanum jamaicense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13692 Leontice kiangnanensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14845 Ceratophyllum submersum Species Ceratophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO893 Helichrysum sutherlandii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17253 Soulamea soulameoides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3164 Yponomeuta malinellus Species Yponomeutidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1641 Amycolatopsis azurea Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13494 Prosopis kuntzei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9024 Aralidium pinnatifidum Species Torricelliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11432 Centrolobium tomentosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13798 Cheilanthes marantae Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12944 Sideritis tragoriganum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO211 Aplysina cauliformis Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22888 Lophiostoma vaginatispora Species Lophiostomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6014 Goniothalamus undulatus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13604 Dermocybe cardinalis Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15146 Myrica nana Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12026 Papaver radicatum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12890 Ophryosporus charua Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14280 Helichrysum angustifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1418 Boletinus paluster Species Gyrodontaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12717 Parmelia metastrigosa Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8640 Nemuaron humboldtii Species Atherospermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12089 Trifolium alexandrinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14749 Lippia carviodora Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9203 Cephalonomia gallicola Species Bethylidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3576 Bersama swinnyi Species Melianthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2084 Acinetobacter calcoaceticus Species Moraxellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2505 Pachycereus pringlei Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12577 Pinus glauca Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6626 Pteris spinulosa Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10818 Carpobrotus edulis Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3924 Penicillium alutaceum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11637 Psilostrophe cooperi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26718 Chelidonura fulvipunctata Species Aglajidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12988 Blainvillea latifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11530 Heterosigma akashiwo Species Chattonellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20318 Acinetobacter baumannii Species Moraxellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20383 Stenocereus thurberi Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5401 Monanchora unguiculata Species Crambeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9375 Medium grandiflorum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO11873 Oecophylla smaragdina Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5303 Castanea crenata Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11084 Asplenium normale Species Aspleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14528 Pneumatospora obcoronata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO8820 Lophocereus marginatus Species Cactaceae 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
NPT91 Cell Line KB Homo sapiens ED50 = 2.1 ug ml-1 PMID[491412]
NPT168 Cell Line P388 Mus musculus ED50 = 2.3 ug ml-1 PMID[491412]
NPT168 Cell Line P388 Mus musculus T/C = 102.0 % PMID[491412]
NPT168 Cell Line P388 Mus musculus T/C = 107.0 % PMID[491412]
NPT168 Cell Line P388 Mus musculus T/C = 108.0 % PMID[491412]
NPT91 Cell Line KB Homo sapiens ED50 <= 4.0 ug ml-1 PMID[491413]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 20596.2 nM PMID[491414]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 9196.2 nM PMID[491414]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 89125.1 nM PMID[491414]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 22387.2 nM PMID[491414]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 20596.2 nM PMID[491414]
NPT11 Individual Protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 1258.9 nM PMID[491414]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 18356.4 nM PMID[491414]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 9200.0 nM PMID[491414]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 50.6 % PMID[491415]
NPT2 Others Unspecified EC50 = 12717.0 nM PMID[491414]
NPT2 Others Unspecified EC50 = 9942.0 nM PMID[491414]
NPT2 Others Unspecified EC50 = 11888.0 nM PMID[491414]
NPT2 Others Unspecified IC50 = 2100.0 nM PMID[491414]
NPT2 Others Unspecified IC50 = 2930.0 nM PMID[491414]
NPT2 Others Unspecified IC50 > 80000.0 nM PMID[491414]
NPT2 Others Unspecified IC50 = 2300.0 nM PMID[491414]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 1041.8 nM PMID[491414]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 17782.8 nM PMID[491414]
NPT2 Others Unspecified Potency n.a. 7943.3 nM PMID[491414]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 18526.0 nM PMID[491414]
NPT2 Others Unspecified Potency n.a. 12589.3 nM PMID[491414]

☑ 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 NPC200836 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
0.9672 High Similarity NPC53144
0.9405 High Similarity NPC211813
0.9365 High Similarity NPC85273
0.9211 High Similarity NPC174672
0.8912 High Similarity NPC174758
0.8667 High Similarity NPC82548
0.8643 High Similarity NPC274982
0.8571 High Similarity NPC287208
0.849 Intermediate Similarity NPC212213
0.8299 Intermediate Similarity NPC239954
0.8281 Intermediate Similarity NPC198673
0.828 Intermediate Similarity NPC24864
0.8196 Intermediate Similarity NPC242209
0.8141 Intermediate Similarity NPC475070
0.8135 Intermediate Similarity NPC324149
0.8115 Intermediate Similarity NPC46580
0.8112 Intermediate Similarity NPC168911
0.8111 Intermediate Similarity NPC293487
0.8065 Intermediate Similarity NPC99891
0.803 Intermediate Similarity NPC5145
0.802 Intermediate Similarity NPC192315
0.801 Intermediate Similarity NPC476121
0.801 Intermediate Similarity NPC476124
0.7981 Intermediate Similarity NPC193267
0.7981 Intermediate Similarity NPC213530
0.798 Intermediate Similarity NPC476167
0.7978 Intermediate Similarity NPC478182
0.7929 Intermediate Similarity NPC474916
0.7923 Intermediate Similarity NPC478185
0.7903 Intermediate Similarity NPC32534
0.79 Intermediate Similarity NPC232727
0.7892 Intermediate Similarity NPC478183
0.788 Intermediate Similarity NPC478184
0.788 Intermediate Similarity NPC477549
0.7871 Intermediate Similarity NPC470500
0.7869 Intermediate Similarity NPC25899
0.7861 Intermediate Similarity NPC57398
0.7861 Intermediate Similarity NPC295898
0.7847 Intermediate Similarity NPC264285
0.7842 Intermediate Similarity NPC12649
0.7838 Intermediate Similarity NPC471178
0.7826 Intermediate Similarity NPC48192
0.782 Intermediate Similarity NPC60621
0.782 Intermediate Similarity NPC310118
0.7819 Intermediate Similarity NPC474409
0.7817 Intermediate Similarity NPC106937
0.7799 Intermediate Similarity NPC27041
0.7789 Intermediate Similarity NPC267928
0.7789 Intermediate Similarity NPC96890
0.7749 Intermediate Similarity NPC72980
0.7732 Intermediate Similarity NPC314002
0.772 Intermediate Similarity NPC220765
0.7714 Intermediate Similarity NPC476041
0.7714 Intermediate Similarity NPC304926
0.7713 Intermediate Similarity NPC91895
0.77 Intermediate Similarity NPC220851
0.7696 Intermediate Similarity NPC472259
0.7692 Intermediate Similarity NPC171171
0.7692 Intermediate Similarity NPC477861
0.7689 Intermediate Similarity NPC128115
0.7681 Intermediate Similarity NPC123976
0.7681 Intermediate Similarity NPC167860
0.768 Intermediate Similarity NPC204717
0.7677 Intermediate Similarity NPC99666
0.7674 Intermediate Similarity NPC214980
0.7673 Intermediate Similarity NPC176538
0.7661 Intermediate Similarity NPC207686
0.7639 Intermediate Similarity NPC110151
0.7638 Intermediate Similarity NPC329541
0.7634 Intermediate Similarity NPC59779
0.7634 Intermediate Similarity NPC472434
0.7634 Intermediate Similarity NPC124542
0.7634 Intermediate Similarity NPC471177
0.7629 Intermediate Similarity NPC48938
0.7626 Intermediate Similarity NPC141053
0.7621 Intermediate Similarity NPC53344
0.7617 Intermediate Similarity NPC16352
0.761 Intermediate Similarity NPC285558
0.7608 Intermediate Similarity NPC128084
0.7594 Intermediate Similarity NPC97367
0.7586 Intermediate Similarity NPC19872
0.7583 Intermediate Similarity NPC8022
0.7583 Intermediate Similarity NPC470799
0.7581 Intermediate Similarity NPC122436
0.7548 Intermediate Similarity NPC80596
0.7537 Intermediate Similarity NPC81535
0.7536 Intermediate Similarity NPC237740
0.7536 Intermediate Similarity NPC183777
0.7536 Intermediate Similarity NPC270918
0.7525 Intermediate Similarity NPC474188
0.7525 Intermediate Similarity NPC156704
0.7525 Intermediate Similarity NPC77555
0.7522 Intermediate Similarity NPC178858
0.7514 Intermediate Similarity NPC478186
0.7513 Intermediate Similarity NPC184964
0.7512 Intermediate Similarity NPC326634
0.75 Intermediate Similarity NPC18348
0.75 Intermediate Similarity NPC121772
0.7477 Intermediate Similarity NPC6215
0.7475 Intermediate Similarity NPC13880
0.7465 Intermediate Similarity NPC469727
0.7464 Intermediate Similarity NPC469589
0.7456 Intermediate Similarity NPC63971
0.7456 Intermediate Similarity NPC91868
0.7449 Intermediate Similarity NPC212535
0.7438 Intermediate Similarity NPC90229
0.7435 Intermediate Similarity NPC314940
0.7435 Intermediate Similarity NPC473764
0.7429 Intermediate Similarity NPC11464
0.7424 Intermediate Similarity NPC314573
0.7424 Intermediate Similarity NPC62749
0.7421 Intermediate Similarity NPC56233
0.7418 Intermediate Similarity NPC322064
0.7415 Intermediate Similarity NPC45459
0.7415 Intermediate Similarity NPC249040
0.7415 Intermediate Similarity NPC213308
0.7415 Intermediate Similarity NPC315491
0.7406 Intermediate Similarity NPC316181
0.7406 Intermediate Similarity NPC74562
0.7406 Intermediate Similarity NPC151781
0.7405 Intermediate Similarity NPC36168
0.7402 Intermediate Similarity NPC306376
0.7395 Intermediate Similarity NPC17565
0.7394 Intermediate Similarity NPC131718
0.7391 Intermediate Similarity NPC476138
0.7391 Intermediate Similarity NPC245816
0.7381 Intermediate Similarity NPC185782
0.7376 Intermediate Similarity NPC260434
0.7376 Intermediate Similarity NPC476451
0.7374 Intermediate Similarity NPC295158
0.7374 Intermediate Similarity NPC94943
0.7371 Intermediate Similarity NPC472435
0.7366 Intermediate Similarity NPC235685
0.7358 Intermediate Similarity NPC202605
0.7358 Intermediate Similarity NPC264176
0.7358 Intermediate Similarity NPC294620
0.7358 Intermediate Similarity NPC112206
0.7354 Intermediate Similarity NPC182222
0.7354 Intermediate Similarity NPC97902
0.7352 Intermediate Similarity NPC319232
0.7352 Intermediate Similarity NPC24370
0.735 Intermediate Similarity NPC472289
0.7348 Intermediate Similarity NPC26543
0.7347 Intermediate Similarity NPC271792
0.7346 Intermediate Similarity NPC309845
0.7343 Intermediate Similarity NPC470678
0.7342 Intermediate Similarity NPC279189
0.7342 Intermediate Similarity NPC200553
0.734 Intermediate Similarity NPC276517
0.7333 Intermediate Similarity NPC101350
0.7333 Intermediate Similarity NPC41679
0.7333 Intermediate Similarity NPC326575
0.733 Intermediate Similarity NPC315957
0.733 Intermediate Similarity NPC326363
0.7324 Intermediate Similarity NPC476287
0.7323 Intermediate Similarity NPC190007
0.7321 Intermediate Similarity NPC474145
0.7321 Intermediate Similarity NPC475841
0.7321 Intermediate Similarity NPC238457
0.7317 Intermediate Similarity NPC470499
0.7316 Intermediate Similarity NPC473057
0.731 Intermediate Similarity NPC314394
0.7308 Intermediate Similarity NPC475774
0.7308 Intermediate Similarity NPC223427
0.7306 Intermediate Similarity NPC252590
0.7304 Intermediate Similarity NPC472193
0.7299 Intermediate Similarity NPC476116
0.7296 Intermediate Similarity NPC248462
0.7294 Intermediate Similarity NPC162748
0.7294 Intermediate Similarity NPC470501
0.7293 Intermediate Similarity NPC60553
0.7287 Intermediate Similarity NPC129721
0.7285 Intermediate Similarity NPC314954
0.7281 Intermediate Similarity NPC276657
0.7277 Intermediate Similarity NPC471603
0.7277 Intermediate Similarity NPC26679
0.7277 Intermediate Similarity NPC219087
0.7277 Intermediate Similarity NPC472436
0.7277 Intermediate Similarity NPC325976
0.7273 Intermediate Similarity NPC60006
0.7269 Intermediate Similarity NPC173080
0.7268 Intermediate Similarity NPC78767
0.7268 Intermediate Similarity NPC473814
0.726 Intermediate Similarity NPC65277
0.7256 Intermediate Similarity NPC148183
0.7256 Intermediate Similarity NPC152768
0.7256 Intermediate Similarity NPC183407
0.7255 Intermediate Similarity NPC93390
0.7251 Intermediate Similarity NPC171787
0.7249 Intermediate Similarity NPC78609
0.7248 Intermediate Similarity NPC470502
0.7244 Intermediate Similarity NPC162002
0.7244 Intermediate Similarity NPC295228
0.7238 Intermediate Similarity NPC472111
0.7237 Intermediate Similarity NPC473312
0.7236 Intermediate Similarity NPC284678
0.7233 Intermediate Similarity NPC131887
0.7231 Intermediate Similarity NPC303225
0.7227 Intermediate Similarity NPC245348
0.7225 Intermediate Similarity NPC476098

  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 NPC200836 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
0.7908 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7843 Intermediate Similarity NPD2916 Discontinued
0.7817 Intermediate Similarity NPD802 Phase 2
0.7706 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7641 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7624 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.7624 Intermediate Similarity NPD6999 Discontinued
0.7583 Intermediate Similarity NPD7112 Discontinued
0.7576 Intermediate Similarity NPD3321 Discontinued
0.7573 Intermediate Similarity NPD3932 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD4845 Discontinued
0.7547 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD7948 Phase 1
0.7512 Intermediate Similarity NPD6975 Discontinued
0.7512 Intermediate Similarity NPD7426 Phase 1
0.7512 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7512 Intermediate Similarity NPD7603 Discontinued
0.75 Intermediate Similarity NPD7666 Phase 3
0.75 Intermediate Similarity NPD7665 Phase 2
0.7453 Intermediate Similarity NPD4897 Phase 2
0.7452 Intermediate Similarity NPD3930 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD4795 Phase 2
0.7437 Intermediate Similarity NPD6965 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD424 Approved
0.7421 Intermediate Similarity NPD425 Approved
0.7415 Intermediate Similarity NPD484 Approved
0.7413 Intermediate Similarity NPD4372 Phase 1
0.7409 Intermediate Similarity NPD5065 Approved
0.7407 Intermediate Similarity NPD5507 Approved
0.7407 Intermediate Similarity NPD5506 Approved
0.7378 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD2814 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD925 Approved
0.7368 Intermediate Similarity NPD926 Approved
0.7345 Intermediate Similarity NPD6790 Phase 1
0.733 Intermediate Similarity NPD1739 Approved
0.733 Intermediate Similarity NPD1740 Approved
0.7321 Intermediate Similarity NPD5530 Phase 1
0.7321 Intermediate Similarity NPD7001 Phase 3
0.7321 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7306 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD2383 Phase 1
0.7273 Intermediate Similarity NPD5901 Discontinued
0.726 Intermediate Similarity NPD3928 Approved
0.726 Intermediate Similarity NPD3931 Approved
0.7258 Intermediate Similarity NPD2882 Phase 1
0.7256 Intermediate Similarity NPD6803 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD4901 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD7558 Phase 2
0.7231 Intermediate Similarity NPD9690 Approved
0.7225 Intermediate Similarity NPD4886 Phase 2
0.7222 Intermediate Similarity NPD4203 Approved
0.7222 Intermediate Similarity NPD4204 Approved
0.7211 Intermediate Similarity NPD112 Approved
0.7211 Intermediate Similarity NPD9705 Discontinued
0.7206 Intermediate Similarity NPD1038 Approved
0.7206 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD1197 Approved
0.7204 Intermediate Similarity NPD1392 Approved
0.7204 Intermediate Similarity NPD7222 Phase 2
0.7202 Intermediate Similarity NPD2781 Approved
0.72 Intermediate Similarity NPD2762 Phase 2
0.72 Intermediate Similarity NPD5555 Phase 1
0.7198 Intermediate Similarity NPD5482 Discontinued
0.7196 Intermediate Similarity NPD3330 Phase 1
0.7188 Intermediate Similarity NPD2782 Approved
0.7188 Intermediate Similarity NPD2780 Approved
0.7163 Intermediate Similarity NPD6389 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD5255 Approved
0.7157 Intermediate Similarity NPD6159 Phase 2
0.7157 Intermediate Similarity NPD5751 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD5601 Phase 2
0.7149 Intermediate Similarity NPD7586 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5513 Phase 2
0.7124 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD2757 Phase 2
0.7123 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD6242 Discontinued
0.7121 Intermediate Similarity NPD1503 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD3813 Approved
0.7117 Intermediate Similarity NPD7675 Phase 3
0.7117 Intermediate Similarity NPD7674 Phase 3
0.7117 Intermediate Similarity NPD7676 Clinical (unspecified phase)
0.7116 Intermediate Similarity NPD3815 Phase 1
0.7116 Intermediate Similarity NPD3816 Phase 1
0.7107 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD5100 Phase 3
0.7103 Intermediate Similarity NPD4900 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD5658 Approved
0.7087 Intermediate Similarity NPD7944 Discontinued
0.7085 Intermediate Similarity NPD6452 Discontinued
0.7079 Intermediate Similarity NPD706 Phase 1
0.7078 Intermediate Similarity NPD7203 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD9706 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD3404 Approved
0.7073 Intermediate Similarity NPD6569 Phase 2
0.7056 Intermediate Similarity NPD7068 Approved
0.7056 Intermediate Similarity NPD7067 Approved
0.7054 Intermediate Similarity NPD5559 Phase 2
0.7048 Intermediate Similarity NPD6970 Phase 2
0.7044 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD7452 Approved
0.7042 Intermediate Similarity NPD7453 Approved
0.7039 Intermediate Similarity NPD9695 Approved
0.703 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD4336 Clinical (unspecified phase)
0.7028 Intermediate Similarity NPD4033 Approved
0.7028 Intermediate Similarity NPD4039 Approved
0.7028 Intermediate Similarity NPD31 Approved
0.7028 Intermediate Similarity NPD4037 Approved
0.7028 Intermediate Similarity NPD32 Approved
0.7028 Intermediate Similarity NPD7712 Clinical (unspecified phase)
0.7028 Intermediate Similarity NPD4035 Approved
0.7028 Intermediate Similarity NPD5426 Phase 3
0.7028 Intermediate Similarity NPD4122 Approved
0.7028 Intermediate Similarity NPD4036 Approved
0.7028 Intermediate Similarity NPD4034 Approved
0.7028 Intermediate Similarity NPD4038 Approved
0.7022 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD2952 Discontinued
0.7019 Intermediate Similarity NPD1622 Discontinued
0.7014 Intermediate Similarity NPD4923 Phase 1
0.701 Intermediate Similarity NPD4334 Discontinued
0.7009 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD1661 Suspended
0.7005 Intermediate Similarity NPD4418 Discontinued
0.7 Intermediate Similarity NPD7025 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7194 Discontinued
0.6995 Remote Similarity NPD3003 Approved
0.6991 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6991 Remote Similarity NPD3570 Phase 2
0.699 Remote Similarity NPD5505 Discontinued
0.6986 Remote Similarity NPD4989 Phase 2
0.6984 Remote Similarity NPD6476 Clinical (unspecified phase)
0.6984 Remote Similarity NPD6158 Phase 2
0.6983 Remote Similarity NPD8284 Discontinued
0.6978 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6976 Remote Similarity NPD6281 Approved
0.6976 Remote Similarity NPD1213 Phase 3
0.6976 Remote Similarity NPD3439 Approved
0.6975 Remote Similarity NPD6961 Discontinued
0.697 Remote Similarity NPD6492 Phase 2
0.6968 Remote Similarity NPD5827 Discontinued
0.6965 Remote Similarity NPD7414 Clinical (unspecified phase)
0.6961 Remote Similarity NPD4948 Discontinued
0.6959 Remote Similarity NPD4852 Phase 2
0.6958 Remote Similarity NPD7923 Phase 2
0.6953 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6952 Remote Similarity NPD6137 Clinical (unspecified phase)
0.6948 Remote Similarity NPD6138 Clinical (unspecified phase)
0.6947 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6942 Remote Similarity NPD2336 Approved
0.6942 Remote Similarity NPD6022 Clinical (unspecified phase)
0.6941 Remote Similarity NPD5612 Discontinued
0.6939 Remote Similarity NPD4638 Approved
0.6939 Remote Similarity NPD4640 Approved
0.6939 Remote Similarity NPD4639 Approved
0.6939 Remote Similarity NPD6872 Clinical (unspecified phase)
0.6938 Remote Similarity NPD6206 Phase 1
0.6936 Remote Similarity NPD4558 Phase 2
0.6933 Remote Similarity NPD7161 Clinical (unspecified phase)
0.6933 Remote Similarity NPD8246 Approved
0.6933 Remote Similarity NPD8247 Approved
0.693 Remote Similarity NPD4373 Phase 2
0.6927 Remote Similarity NPD3243 Approved
0.6923 Remote Similarity NPD2720 Phase 1
0.6923 Remote Similarity NPD2719 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5488 Discontinued
0.6923 Remote Similarity NPD6861 Clinical (unspecified phase)
0.6919 Remote Similarity NPD750 Phase 2
0.6915 Remote Similarity NPD4703 Approved
0.6915 Remote Similarity NPD4702 Approved
0.6908 Remote Similarity NPD3924 Approved
0.6908 Remote Similarity NPD3923 Approved
0.6908 Remote Similarity NPD3922 Approved
0.6908 Remote Similarity NPD6887 Clinical (unspecified phase)
0.6908 Remote Similarity NPD3921 Approved
0.6907 Remote Similarity NPD3809 Discontinued
0.6906 Remote Similarity NPD8356 Approved
0.6906 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6905 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7555 Discontinued
0.6892 Remote Similarity NPD8479 Phase 2
0.6888 Remote Similarity NPD6530 Approved
0.6888 Remote Similarity NPD6531 Approved
0.6887 Remote Similarity NPD4511 Phase 1
0.6887 Remote Similarity NPD5017 Discontinued
0.6886 Remote Similarity NPD7796 Approved
0.6886 Remote Similarity NPD7797 Approved
0.6881 Remote Similarity NPD3386 Phase 2
0.6881 Remote Similarity NPD8093 Discontinued
0.6881 Remote Similarity NPD7069 Discontinued
0.6875 Remote Similarity NPD8091 Phase 3
0.6872 Remote Similarity NPD4952 Phase 3
0.6872 Remote Similarity NPD1768 Approved
0.6872 Remote Similarity NPD3814 Phase 1
0.6869 Remote Similarity NPD1078 Clinical (unspecified phase)
0.6869 Remote Similarity NPD6987 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