Structure

Physi-Chem Properties

Molecular Weight:  226.07
Volume:  228.854
LogP:  2.313
LogD:  2.308
LogS:  -3.153
# Rotatable Bonds:  2
TPSA:  54.98
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.648
Synthetic Accessibility Score:  2.107
Fsp3:  0.077
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:  -4.923
MDCK Permeability:  2.144149038940668e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.961
Plasma Protein Binding (PPB):  84.69815063476562%
Volume Distribution (VD):  0.804
Pgp-substrate:  13.425803184509277%

ADMET: Metabolism

CYP1A2-inhibitor:  0.991
CYP1A2-substrate:  0.931
CYP2C19-inhibitor:  0.702
CYP2C19-substrate:  0.34
CYP2C9-inhibitor:  0.3
CYP2C9-substrate:  0.865
CYP2D6-inhibitor:  0.692
CYP2D6-substrate:  0.739
CYP3A4-inhibitor:  0.692
CYP3A4-substrate:  0.194

ADMET: Excretion

Clearance (CL):  5.178
Half-life (T1/2):  0.515

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.875
Drug-inuced Liver Injury (DILI):  0.966
AMES Toxicity:  0.205
Rat Oral Acute Toxicity:  0.533
Maximum Recommended Daily Dose:  0.879
Skin Sensitization:  0.664
Carcinogencity:  0.246
Eye Corrosion:  0.014
Eye Irritation:  0.964
Respiratory Toxicity:  0.978

Download Data

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General Info & Identifiers & Properties  
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Similar NPs/Drugs  

  Natural Product: NPC266249

Natural Product ID:  NPC266249
Common Name*:   1-Methoxycarbonyl-Beta-Carboline
IUPAC Name:   methyl 9H-pyrido[3,4-b]indole-1-carboxylate
Synonyms:  
Standard InCHIKey:  FRNCTTUBAHKEBZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H10N2O2/c1-17-13(16)12-11-9(6-7-14-12)8-4-2-3-5-10(8)15-11/h2-7,15H,1H3
SMILES:  COC(=O)c1nccc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2229719
PubChem CID:   597266
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001140] Harmala 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
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. seed n.a. DOI[10.1016/S0031-9422(99)00216-2]
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]
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]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[1624939]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota roots n.a. n.a. PMID[16989524]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17027268]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota Leaves n.a. n.a. PMID[17637068]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. root n.a. PMID[1800638]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. PMID[18302336]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota roots n.a. n.a. PMID[19299148]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[19586051]
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]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota stems n.a. n.a. PMID[20095629]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[22432912]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. rhizome n.a. PMID[22863942]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23403897]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota aerial parts n.a. n.a. PMID[24042007]
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]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[25506718]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[25905468]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota seeds and root bark Henan, China n.a. PMID[26295746]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. stem n.a. PMID[26724423]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. root n.a. PMID[26724423]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[27494664]
NPO5401 Monanchora unguiculata Species Crambeidae Eukaryota n.a. n.a. n.a. PMID[28368118]
NPO13114 Pleiocarpa pycnantha Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[29664292]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[29667820]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[30917277]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25272 Celastrus angulatus Species Celastraceae 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]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12487 Juniperus horizontalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO893 Helichrysum sutherlandii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23772 Tetradium glabrifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10098 Glycosmis pseudoracemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30610 Picrasma allanthoides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2330 Alchornea cordifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5401 Monanchora unguiculata Species Crambeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO893 Helichrysum sutherlandii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13494 Prosopis kuntzei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9644 Euphorbia resinifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11072 Geigeria schinzii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8640 Nemuaron humboldtii Species Atherospermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18873.2 Salmonella enterica subsp. enterica serovar bovismorbificans Subspecies Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8820 Lophocereus marginatus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11430 Inula grantioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16801 Cota tinctoria Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13798 Cheilanthes marantae Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8220 Russula sardonia Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12577 Pinus glauca Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23772 Tetradium glabrifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13692 Leontice kiangnanensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10098 Glycosmis pseudoracemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15145 Rauvolfia salicifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1759 Alexandrium excavatum Species Gonyaulacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6014 Goniothalamus undulatus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3965 Corynanthe pachyceras Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22888 Lophiostoma vaginatispora Species Lophiostomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14280 Helichrysum angustifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15233 Balanophora japonica Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9024 Aralidium pinnatifidum Species Torricelliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14947 Lathyrus tingitanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1109 Corydalis persica 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]
NPO13604 Dermocybe cardinalis Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6906 Atalantia wightii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3576 Bersama swinnyi Species Melianthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14526 Plectranthus caninus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5470 Cynoglossum amabile Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12026 Papaver radicatum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13848 Amomum daniellii Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12487 Juniperus horizontalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3761 Plectosphaerella cucumerina Species Plectosphaerellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3924 Penicillium alutaceum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25272 Celastrus angulatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12988 Blainvillea latifolia 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]
NPO2505 Pachycereus pringlei Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8372 Picrasma quassioides Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15329 Rhizoplaca baranowii Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11530 Heterosigma akashiwo Species Chattonellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2084 Acinetobacter calcoaceticus 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]
NPO13278 Strychnos spinosa Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13647 Calcarisporium thermophilum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5398 Peucedanum oroselinum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6626 Pteris spinulosa Species Pteridaceae 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]
NPO9965 Eurycoma longifolia Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7521 Hygrophorus eburneus Species Hygrophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20318 Acinetobacter baumannii Species Moraxellaceae Bacteria 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
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 2.9 % PMID[505846]
NPT440 Individual Protein Quinone oxidoreductase Mus musculus CD = 30.2 uM PMID[505848]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus EC50 = 115000.0 nM PMID[505844]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus EC50 = 179000.0 nM PMID[505844]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 73.3 % PMID[505844]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 71.4 % PMID[505844]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 71.9 % PMID[505844]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 60.4 % PMID[505844]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 68.4 % PMID[505844]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 47.4 % PMID[505844]
NPT2 Others Unspecified IC50 = 29300.0 nM PMID[505845]
NPT2 Others Unspecified Inhibition > 50.0 % PMID[505845]
NPT5110 Organism Meriones unguiculatus Meriones unguiculatus Activity <= 40.0 % PMID[505847]
NPT5110 Organism Meriones unguiculatus Meriones unguiculatus Activity = 30.1 % PMID[505847]
NPT2 Others Unspecified IC50 > 50000.0 nM PMID[505848]

☑ 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 NPC266249 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
0.9892 High Similarity NPC123839
0.9375 High Similarity NPC118940
0.902 High Similarity NPC260434
0.901 High Similarity NPC132539
0.8889 High Similarity NPC477979
0.8889 High Similarity NPC182222
0.8777 High Similarity NPC138370
0.8757 High Similarity NPC284678
0.8634 High Similarity NPC122436
0.8564 High Similarity NPC36405
0.8548 High Similarity NPC191415
0.8544 High Similarity NPC229893
0.852 High Similarity NPC57398
0.8503 High Similarity NPC102755
0.8465 Intermediate Similarity NPC89508
0.8454 Intermediate Similarity NPC141454
0.8384 Intermediate Similarity NPC165599
0.8341 Intermediate Similarity NPC312645
0.8333 Intermediate Similarity NPC148889
0.8316 Intermediate Similarity NPC282103
0.8316 Intermediate Similarity NPC474916
0.8308 Intermediate Similarity NPC102592
0.8308 Intermediate Similarity NPC79356
0.8274 Intermediate Similarity NPC81535
0.8229 Intermediate Similarity NPC278434
0.8211 Intermediate Similarity NPC48938
0.8209 Intermediate Similarity NPC82053
0.8205 Intermediate Similarity NPC198673
0.8194 Intermediate Similarity NPC235685
0.8168 Intermediate Similarity NPC244741
0.8164 Intermediate Similarity NPC27041
0.816 Intermediate Similarity NPC192712
0.8157 Intermediate Similarity NPC101350
0.8098 Intermediate Similarity NPC82370
0.805 Intermediate Similarity NPC19872
0.8047 Intermediate Similarity NPC267853
0.8047 Intermediate Similarity NPC315062
0.804 Intermediate Similarity NPC239954
0.804 Intermediate Similarity NPC168911
0.802 Intermediate Similarity NPC326422
0.801 Intermediate Similarity NPC471944
0.8009 Intermediate Similarity NPC244897
0.8009 Intermediate Similarity NPC60621
0.799 Intermediate Similarity NPC62749
0.7974 Intermediate Similarity NPC53534
0.7959 Intermediate Similarity NPC469489
0.7936 Intermediate Similarity NPC316411
0.7933 Intermediate Similarity NPC476287
0.7917 Intermediate Similarity NPC469896
0.791 Intermediate Similarity NPC237414
0.7906 Intermediate Similarity NPC14113
0.7906 Intermediate Similarity NPC84827
0.7906 Intermediate Similarity NPC145885
0.7897 Intermediate Similarity NPC160381
0.7877 Intermediate Similarity NPC323969
0.7867 Intermediate Similarity NPC63971
0.7867 Intermediate Similarity NPC91868
0.7865 Intermediate Similarity NPC248041
0.7865 Intermediate Similarity NPC126709
0.7864 Intermediate Similarity NPC104712
0.7864 Intermediate Similarity NPC15801
0.7861 Intermediate Similarity NPC67288
0.786 Intermediate Similarity NPC258048
0.7853 Intermediate Similarity NPC151635
0.7843 Intermediate Similarity NPC245816
0.7843 Intermediate Similarity NPC476138
0.7843 Intermediate Similarity NPC317701
0.783 Intermediate Similarity NPC74360
0.7772 Intermediate Similarity NPC212213
0.7772 Intermediate Similarity NPC283219
0.7768 Intermediate Similarity NPC152620
0.7763 Intermediate Similarity NPC102593
0.7763 Intermediate Similarity NPC196718
0.7763 Intermediate Similarity NPC207686
0.7762 Intermediate Similarity NPC234078
0.7762 Intermediate Similarity NPC221100
0.776 Intermediate Similarity NPC267885
0.775 Intermediate Similarity NPC472295
0.775 Intermediate Similarity NPC269886
0.775 Intermediate Similarity NPC247735
0.775 Intermediate Similarity NPC81802
0.775 Intermediate Similarity NPC472210
0.7745 Intermediate Similarity NPC232727
0.7734 Intermediate Similarity NPC103361
0.7734 Intermediate Similarity NPC123395
0.7725 Intermediate Similarity NPC41717
0.772 Intermediate Similarity NPC284775
0.7718 Intermediate Similarity NPC472259
0.7711 Intermediate Similarity NPC135950
0.7708 Intermediate Similarity NPC149155
0.7708 Intermediate Similarity NPC203468
0.7708 Intermediate Similarity NPC110500
0.7704 Intermediate Similarity NPC207851
0.77 Intermediate Similarity NPC472292
0.77 Intermediate Similarity NPC55493
0.7696 Intermediate Similarity NPC176538
0.7692 Intermediate Similarity NPC97902
0.7688 Intermediate Similarity NPC83111
0.7688 Intermediate Similarity NPC324091
0.7682 Intermediate Similarity NPC279189
0.7682 Intermediate Similarity NPC200553
0.768 Intermediate Similarity NPC219336
0.7673 Intermediate Similarity NPC472293
0.7656 Intermediate Similarity NPC185782
0.7653 Intermediate Similarity NPC472285
0.7635 Intermediate Similarity NPC267928
0.7635 Intermediate Similarity NPC167710
0.7633 Intermediate Similarity NPC327592
0.763 Intermediate Similarity NPC318299
0.7629 Intermediate Similarity NPC183662
0.7629 Intermediate Similarity NPC217372
0.7629 Intermediate Similarity NPC15573
0.7624 Intermediate Similarity NPC202812
0.7621 Intermediate Similarity NPC473761
0.7613 Intermediate Similarity NPC174489
0.761 Intermediate Similarity NPC214428
0.7608 Intermediate Similarity NPC287208
0.7606 Intermediate Similarity NPC322064
0.76 Intermediate Similarity NPC154339
0.7596 Intermediate Similarity NPC317373
0.7594 Intermediate Similarity NPC317752
0.7592 Intermediate Similarity NPC78020
0.7579 Intermediate Similarity NPC42372
0.7578 Intermediate Similarity NPC162002
0.7574 Intermediate Similarity NPC267343
0.7561 Intermediate Similarity NPC472297
0.7561 Intermediate Similarity NPC472296
0.755 Intermediate Similarity NPC321708
0.7548 Intermediate Similarity NPC470500
0.7547 Intermediate Similarity NPC26679
0.7545 Intermediate Similarity NPC240384
0.7545 Intermediate Similarity NPC26641
0.7538 Intermediate Similarity NPC235684
0.7538 Intermediate Similarity NPC111275
0.7537 Intermediate Similarity NPC220151
0.7537 Intermediate Similarity NPC19692
0.7526 Intermediate Similarity NPC293216
0.7524 Intermediate Similarity NPC116555
0.7522 Intermediate Similarity NPC165964
0.7521 Intermediate Similarity NPC74619
0.7513 Intermediate Similarity NPC322644
0.75 Intermediate Similarity NPC201380
0.75 Intermediate Similarity NPC57453
0.75 Intermediate Similarity NPC213468
0.75 Intermediate Similarity NPC470894
0.75 Intermediate Similarity NPC179787
0.75 Intermediate Similarity NPC472116
0.7487 Intermediate Similarity NPC280290
0.7487 Intermediate Similarity NPC133003
0.7478 Intermediate Similarity NPC37152
0.7476 Intermediate Similarity NPC476167
0.7476 Intermediate Similarity NPC243850
0.7475 Intermediate Similarity NPC476460
0.7474 Intermediate Similarity NPC252572
0.7467 Intermediate Similarity NPC178858
0.7465 Intermediate Similarity NPC471193
0.7465 Intermediate Similarity NPC471194
0.7464 Intermediate Similarity NPC470505
0.7463 Intermediate Similarity NPC221873
0.7463 Intermediate Similarity NPC63199
0.7463 Intermediate Similarity NPC111602
0.7463 Intermediate Similarity NPC196251
0.7463 Intermediate Similarity NPC102338
0.7462 Intermediate Similarity NPC73994
0.7459 Intermediate Similarity NPC321911
0.7455 Intermediate Similarity NPC24370
0.7455 Intermediate Similarity NPC319232
0.7453 Intermediate Similarity NPC123976
0.7453 Intermediate Similarity NPC167860
0.7452 Intermediate Similarity NPC476874
0.745 Intermediate Similarity NPC94752
0.7446 Intermediate Similarity NPC63545
0.7442 Intermediate Similarity NPC470799
0.7442 Intermediate Similarity NPC8022
0.744 Intermediate Similarity NPC315491
0.744 Intermediate Similarity NPC45459
0.7437 Intermediate Similarity NPC477003
0.7437 Intermediate Similarity NPC46895
0.7429 Intermediate Similarity NPC472065
0.7429 Intermediate Similarity NPC472064
0.7429 Intermediate Similarity NPC277350
0.7429 Intermediate Similarity NPC238457
0.7427 Intermediate Similarity NPC192315
0.7426 Intermediate Similarity NPC314333
0.7426 Intermediate Similarity NPC329858
0.7424 Intermediate Similarity NPC314394
0.7423 Intermediate Similarity NPC249614
0.7421 Intermediate Similarity NPC131718
0.7419 Intermediate Similarity NPC288987
0.7416 Intermediate Similarity NPC476098
0.7415 Intermediate Similarity NPC245916
0.7411 Intermediate Similarity NPC55772
0.7406 Intermediate Similarity NPC478158
0.7405 Intermediate Similarity NPC469811
0.7398 Intermediate Similarity NPC84347
0.7395 Intermediate Similarity NPC478157
0.7393 Intermediate Similarity NPC183777
0.7393 Intermediate Similarity NPC321428
0.7391 Intermediate Similarity NPC284338
0.7391 Intermediate Similarity NPC241024

  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 NPC266249 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
0.886 High Similarity NPD2121 Clinical (unspecified phase)
0.8492 Intermediate Similarity NPD2510 Approved
0.8492 Intermediate Similarity NPD2509 Approved
0.8458 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.8398 Intermediate Similarity NPD1996 Discontinued
0.8382 Intermediate Similarity NPD3389 Approved
0.8382 Intermediate Similarity NPD3394 Approved
0.8382 Intermediate Similarity NPD3393 Approved
0.8303 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.8276 Intermediate Similarity NPD5475 Discontinued
0.8153 Intermediate Similarity NPD5482 Discontinued
0.803 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7915 Intermediate Similarity NPD7404 Approved
0.7837 Intermediate Similarity NPD7470 Discontinued
0.7784 Intermediate Similarity NPD3178 Discontinued
0.776 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7735 Intermediate Similarity NPD5450 Discontinued
0.7718 Intermediate Similarity NPD5901 Discontinued
0.7708 Intermediate Similarity NPD482 Approved
0.7678 Intermediate Similarity NPD3794 Approved
0.7678 Intermediate Similarity NPD3795 Approved
0.767 Intermediate Similarity NPD6176 Phase 1
0.7658 Intermediate Similarity NPD3006 Discontinued
0.7633 Intermediate Similarity NPD3947 Discontinued
0.7617 Intermediate Similarity NPD4429 Discontinued
0.7581 Intermediate Similarity NPD6770 Approved
0.7549 Intermediate Similarity NPD5003 Discontinued
0.7545 Intermediate Similarity NPD4958 Clinical (unspecified phase)
0.7512 Intermediate Similarity NPD7010 Phase 3
0.75 Intermediate Similarity NPD4948 Discontinued
0.7476 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD2092 Phase 2
0.7475 Intermediate Similarity NPD2095 Phase 2
0.7475 Intermediate Similarity NPD2094 Phase 2
0.7474 Intermediate Similarity NPD750 Phase 2
0.7465 Intermediate Similarity NPD6242 Discontinued
0.7455 Intermediate Similarity NPD8289 Discontinued
0.7444 Intermediate Similarity NPD6263 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD484 Approved
0.7437 Intermediate Similarity NPD2096 Phase 2
0.7437 Intermediate Similarity NPD2091 Phase 2
0.7426 Intermediate Similarity NPD4499 Approved
0.7406 Intermediate Similarity NPD4506 Discontinued
0.7385 Intermediate Similarity NPD3280 Approved
0.7371 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD4376 Phase 3
0.7347 Intermediate Similarity NPD5065 Approved
0.7345 Intermediate Similarity NPD5891 Approved
0.734 Intermediate Similarity NPD2565 Phase 2
0.734 Intermediate Similarity NPD2564 Approved
0.7328 Intermediate Similarity NPD4558 Phase 2
0.7327 Intermediate Similarity NPD1591 Approved
0.7306 Intermediate Similarity NPD2915 Discontinued
0.7302 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD7603 Discontinued
0.7294 Intermediate Similarity NPD5632 Approved
0.7277 Intermediate Similarity NPD5022 Discontinued
0.7277 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6479 Discontinued
0.7265 Intermediate Similarity NPD7994 Phase 2
0.7264 Intermediate Similarity NPD6178 Phase 3
0.7264 Intermediate Similarity NPD1096 Discontinued
0.7256 Intermediate Similarity NPD5416 Discontinued
0.7248 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD5293 Phase 2
0.7225 Intermediate Similarity NPD2582 Approved
0.7225 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD2581 Approved
0.7222 Intermediate Similarity NPD8093 Discontinued
0.7217 Intermediate Similarity NPD2721 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD6288 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD1623 Approved
0.7209 Intermediate Similarity NPD5072 Discontinued
0.719 Intermediate Similarity NPD4500 Approved
0.719 Intermediate Similarity NPD4501 Approved
0.7183 Intermediate Similarity NPD2008 Discontinued
0.7179 Intermediate Similarity NPD4554 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD1783 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD3757 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD5017 Discontinued
0.715 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD460 Discontinued
0.715 Intermediate Similarity NPD1038 Approved
0.715 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7149 Intermediate Similarity NPD5827 Discontinued
0.7136 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD5592 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD6173 Approved
0.7128 Intermediate Similarity NPD9271 Approved
0.7123 Intermediate Similarity NPD2412 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD7853 Phase 2
0.7117 Intermediate Similarity NPD4301 Approved
0.7116 Intermediate Similarity NPD2443 Approved
0.7116 Intermediate Similarity NPD2442 Approved
0.7115 Intermediate Similarity NPD7618 Phase 3
0.7115 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD7619 Phase 3
0.7109 Intermediate Similarity NPD8248 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD706 Phase 1
0.7105 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD7001 Phase 3
0.7103 Intermediate Similarity NPD2715 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD4922 Phase 2
0.7098 Intermediate Similarity NPD1630 Approved
0.7097 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD7688 Phase 1
0.7089 Intermediate Similarity NPD8072 Approved
0.7083 Intermediate Similarity NPD6529 Discontinued
0.7083 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD8049 Phase 2
0.707 Intermediate Similarity NPD1506 Discontinued
0.707 Intermediate Similarity NPD3371 Approved
0.7067 Intermediate Similarity NPD5887 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD2411 Approved
0.7064 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD5426 Phase 3
0.7053 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD5913 Phase 3
0.7051 Intermediate Similarity NPD4051 Discontinued
0.705 Intermediate Similarity NPD5104 Approved
0.7047 Intermediate Similarity NPD820 Phase 3
0.7042 Intermediate Similarity NPD8073 Approved
0.7037 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD3259 Approved
0.703 Intermediate Similarity NPD6595 Phase 3
0.703 Intermediate Similarity NPD1291 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD7289 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD4614 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.7015 Intermediate Similarity NPD2144 Approved
0.7009 Intermediate Similarity NPD2920 Discontinued
0.7005 Intermediate Similarity NPD1600 Suspended
0.7005 Intermediate Similarity NPD6281 Approved
0.7004 Intermediate Similarity NPD1580 Clinical (unspecified phase)
0.7004 Intermediate Similarity NPD1579 Discontinued
0.7 Intermediate Similarity NPD2951 Discontinued
0.7 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.6996 Remote Similarity NPD6790 Phase 1
0.699 Remote Similarity NPD6141 Clinical (unspecified phase)
0.699 Remote Similarity NPD1631 Approved
0.6986 Remote Similarity NPD3330 Phase 1
0.6982 Remote Similarity NPD6578 Clinical (unspecified phase)
0.6981 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6981 Remote Similarity NPD6999 Discontinued
0.698 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6978 Remote Similarity NPD6752 Phase 1
0.6978 Remote Similarity NPD6753 Phase 1
0.6977 Remote Similarity NPD6987 Phase 1
0.6977 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6976 Remote Similarity NPD7424 Clinical (unspecified phase)
0.6976 Remote Similarity NPD1308 Approved
0.6974 Remote Similarity NPD5479 Discontinued
0.6971 Remote Similarity NPD2336 Approved
0.6971 Remote Similarity NPD6180 Clinical (unspecified phase)
0.697 Remote Similarity NPD5069 Clinical (unspecified phase)
0.696 Remote Similarity NPD7268 Clinical (unspecified phase)
0.696 Remote Similarity NPD6165 Phase 2
0.696 Remote Similarity NPD6164 Phase 2
0.6955 Remote Similarity NPD8094 Discontinued
0.6955 Remote Similarity NPD2823 Clinical (unspecified phase)
0.6952 Remote Similarity NPD1722 Approved
0.6944 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6944 Remote Similarity NPD7957 Phase 1
0.6941 Remote Similarity NPD5067 Phase 2
0.6941 Remote Similarity NPD5066 Phase 2
0.6938 Remote Similarity NPD6665 Discontinued
0.6937 Remote Similarity NPD2787 Clinical (unspecified phase)
0.6937 Remote Similarity NPD8406 Clinical (unspecified phase)
0.6935 Remote Similarity NPD4184 Clinical (unspecified phase)
0.693 Remote Similarity NPD5559 Phase 2
0.6927 Remote Similarity NPD2408 Discontinued
0.6923 Remote Similarity NPD3321 Discontinued
0.6919 Remote Similarity NPD6226 Phase 3
0.6919 Remote Similarity NPD5512 Phase 3
0.6919 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6916 Remote Similarity NPD7727 Phase 2
0.6912 Remote Similarity NPD3038 Discontinued
0.691 Remote Similarity NPD3360 Clinical (unspecified phase)
0.6909 Remote Similarity NPD8096 Phase 3
0.6909 Remote Similarity NPD8097 Phase 3
0.6907 Remote Similarity NPD276 Clinical (unspecified phase)
0.6905 Remote Similarity NPD4528 Approved
0.6905 Remote Similarity NPD4529 Approved
0.6905 Remote Similarity NPD4526 Approved
0.6903 Remote Similarity NPD3222 Phase 2
0.6903 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6901 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6901 Remote Similarity NPD3825 Phase 3
0.69 Remote Similarity NPD4952 Phase 3
0.69 Remote Similarity NPD5801 Clinical (unspecified phase)
0.69 Remote Similarity NPD485 Clinical (unspecified phase)
0.6898 Remote Similarity NPD4795 Phase 2
0.6895 Remote Similarity NPD4900 Clinical (unspecified phase)

  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