Structure

Physi-Chem Properties

Molecular Weight:  222.07
Volume:  238.816
LogP:  3.876
LogD:  3.277
LogS:  -5.673
# Rotatable Bonds:  0
TPSA:  34.14
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.586
Synthetic Accessibility Score:  1.683
Fsp3:  0.067
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.673
MDCK Permeability:  1.7252656107302755e-05
Pgp-inhibitor:  0.578
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.139
Plasma Protein Binding (PPB):  99.28986358642578%
Volume Distribution (VD):  0.784
Pgp-substrate:  1.091099739074707%

ADMET: Metabolism

CYP1A2-inhibitor:  0.933
CYP1A2-substrate:  0.681
CYP2C19-inhibitor:  0.58
CYP2C19-substrate:  0.089
CYP2C9-inhibitor:  0.532
CYP2C9-substrate:  0.408
CYP2D6-inhibitor:  0.072
CYP2D6-substrate:  0.284
CYP3A4-inhibitor:  0.509
CYP3A4-substrate:  0.202

ADMET: Excretion

Clearance (CL):  2.516
Half-life (T1/2):  0.07

ADMET: Toxicity

hERG Blockers:  0.066
Human Hepatotoxicity (H-HT):  0.08
Drug-inuced Liver Injury (DILI):  0.863
AMES Toxicity:  0.717
Rat Oral Acute Toxicity:  0.165
Maximum Recommended Daily Dose:  0.872
Skin Sensitization:  0.066
Carcinogencity:  0.919
Eye Corrosion:  0.004
Eye Irritation:  0.979
Respiratory Toxicity:  0.049

Download Data

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

  Natural Product: NPC289883

Natural Product ID:  NPC289883
Common Name*:   Tectoquinone
IUPAC Name:   2-methylanthracene-9,10-dione
Synonyms:   2-Methyl-Anthraquinone; 2-Methylanthraquinone
Standard InCHIKey:  NJWGQARXZDRHCD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H10O2/c1-9-6-7-12-13(8-9)15(17)11-5-3-2-4-10(11)14(12)16/h2-8H,1H3
SMILES:  Cc1ccc2c(c1)C(=O)c1c(C2=O)cccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL21745
PubChem CID:   6773
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones

*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
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[10075762]
NPO4592 Lippia sidoides Species Verbenaceae Eukaryota n.a. n.a. n.a. PMID[11421746]
NPO16657 Diospyros maritima Species Ebenaceae Eukaryota bark Indonesia n.a. PMID[15270571]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[17950604]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. bark n.a. PMID[17950604]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[18078747]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. Brazilian n.a. PMID[19674905]
NPO1590 Sinningia aggregata Species Gesneriaceae Eukaryota Tubers n.a. n.a. PMID[20684540]
NPO16657 Diospyros maritima Species Ebenaceae Eukaryota n.a. n.a. n.a. PMID[22313254]
NPO33133 barleria alluaudii Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[22313254]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[24433009]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[26048790]
NPO2494 Xanthium strumarium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26081757]
NPO2494 Xanthium strumarium Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[27169184]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[28032759]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[32044231]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[7463094]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8201313]
NPO3049 Rhinacanthus nasutus Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[8463799]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8699182]
NPO3049 Rhinacanthus nasutus Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[8792629]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[8882438]
NPO3049 Rhinacanthus nasutus Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[9214738]
NPO1039 Diospyros sylvatica Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30823 Evodia rutaecarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO26970 Lygodium flexuosum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16657 Diospyros maritima Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30535 Morinda umbellata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18640 Tectona grandis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28407 Clausena heptaphylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16657 Diospyros maritima Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26970 Lygodium flexuosum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28407 Clausena heptaphylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4192 Gynochthodes umbellata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18640 Tectona grandis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3049 Rhinacanthus nasutus Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1039 Diospyros sylvatica Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30823 Evodia rutaecarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30535 Morinda umbellata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16657 Diospyros maritima Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18640 Tectona grandis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28407 Clausena heptaphylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2494 Xanthium strumarium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14480 Tornabea scutellifera Species Physciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4592 Lippia sidoides Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12083 Hydnellum zonatum Species Thelephoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16657 Diospyros maritima Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4192 Gynochthodes umbellata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14417 Iris tectorum Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3049 Rhinacanthus nasutus Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11678 Aeonium cuneatum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3751 Orthantha lutea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12707 Lithospermum canescens Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26970 Lygodium flexuosum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13891 Scolytus multistriatus Species Curculionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28407 Clausena heptaphylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1590 Sinningia aggregata Species Gesneriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11855 Streptomyces xanthocidicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18640 Tectona grandis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2494 Xanthium strumarium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20569 Psychotria serpens Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2842 Cell Line EMT6 Mus musculus ED50 = 1.7 uM PMID[501368]
NPT2842 Cell Line EMT6 Mus musculus ED50 = 0.54 uM PMID[501368]
NPT279 Individual Protein Leukocyte elastase Homo sapiens IC50 = 39000.0 nM PMID[501369]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[501370]
NPT1577 Cell Line SW1573 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[501370]
NPT404 Cell Line CCRF-CEM Homo sapiens IC50 > 10.0 ug.mL-1 PMID[501370]
NPT369 Cell Line ACHN Homo sapiens EC50 > 50000.0 nM PMID[501373]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 100.0 ug.mL-1 PMID[501374]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 100.0 ug.mL-1 PMID[501374]
NPT81 Cell Line A549 Homo sapiens IC50 > 100.0 ug.mL-1 PMID[501374]
NPT737 Cell Line HUVEC Homo sapiens IC50 > 100.0 ug.mL-1 PMID[501374]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 13629.8 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 54261.1 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 68310.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Ratio = 3.2 n.a. PMID[501368]
NPT2 Others Unspecified logIC50 = 2.66 n.a. PMID[501371]
NPT20 Organism Candida albicans Candida albicans MIC > 100.0 ug.mL-1 PMID[501372]
NPT2 Others Unspecified Potency n.a. 34236.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 6088.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24237.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 860 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48360.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27195 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54746.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 689.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54261.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 8599.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 60882 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3841.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68310.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 4310.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 6831.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 7664.6 nM PubChem BioAssay data set

☑ 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 NPC289883 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
0.9655 High Similarity NPC19256
0.9432 High Similarity NPC173413
0.9432 High Similarity NPC277277
0.9425 High Similarity NPC267262
0.9348 High Similarity NPC49994
0.9222 High Similarity NPC155232
0.9205 High Similarity NPC157778
0.9195 High Similarity NPC307
0.9195 High Similarity NPC160339
0.9149 High Similarity NPC476993
0.914 High Similarity NPC134882
0.913 High Similarity NPC219573
0.913 High Similarity NPC185208
0.9121 High Similarity NPC238219
0.9111 High Similarity NPC133461
0.9101 High Similarity NPC418308
0.9091 High Similarity NPC43945
0.9032 High Similarity NPC239185
0.9032 High Similarity NPC265220
0.9022 High Similarity NPC260233
0.9022 High Similarity NPC472880
0.9011 High Similarity NPC59677
0.9011 High Similarity NPC153885
0.8947 High Similarity NPC472879
0.8947 High Similarity NPC109514
0.8936 High Similarity NPC75724
0.8901 High Similarity NPC284475
0.8876 High Similarity NPC69057
0.8804 High Similarity NPC323420
0.8804 High Similarity NPC188844
0.8804 High Similarity NPC1682
0.8696 High Similarity NPC103346
0.8636 High Similarity NPC215008
0.8636 High Similarity NPC273758
0.8621 High Similarity NPC12936
0.8621 High Similarity NPC273033
0.8621 High Similarity NPC145053
0.8571 High Similarity NPC153308
0.8515 High Similarity NPC470252
0.8506 High Similarity NPC71664
0.8478 Intermediate Similarity NPC298115
0.8478 Intermediate Similarity NPC113307
0.8478 Intermediate Similarity NPC325709
0.8391 Intermediate Similarity NPC300205
0.8352 Intermediate Similarity NPC164526
0.8295 Intermediate Similarity NPC164086
0.8295 Intermediate Similarity NPC190567
0.8276 Intermediate Similarity NPC36342
0.8276 Intermediate Similarity NPC285470
0.8276 Intermediate Similarity NPC2785
0.8218 Intermediate Similarity NPC474910
0.8218 Intermediate Similarity NPC172483
0.82 Intermediate Similarity NPC475939
0.82 Intermediate Similarity NPC471829
0.82 Intermediate Similarity NPC247976
0.82 Intermediate Similarity NPC474866
0.82 Intermediate Similarity NPC472691
0.8173 Intermediate Similarity NPC265513
0.8161 Intermediate Similarity NPC245966
0.8113 Intermediate Similarity NPC67377
0.8113 Intermediate Similarity NPC196673
0.8095 Intermediate Similarity NPC280789
0.8095 Intermediate Similarity NPC186128
0.809 Intermediate Similarity NPC285716
0.809 Intermediate Similarity NPC95868
0.809 Intermediate Similarity NPC17408
0.8058 Intermediate Similarity NPC203732
0.8043 Intermediate Similarity NPC252067
0.8039 Intermediate Similarity NPC134120
0.8022 Intermediate Similarity NPC39600
0.8022 Intermediate Similarity NPC197581
0.802 Intermediate Similarity NPC274443
0.8019 Intermediate Similarity NPC93287
0.8019 Intermediate Similarity NPC470253
0.7978 Intermediate Similarity NPC139901
0.7978 Intermediate Similarity NPC151405
0.7961 Intermediate Similarity NPC472699
0.7961 Intermediate Similarity NPC100767
0.7961 Intermediate Similarity NPC472700
0.7944 Intermediate Similarity NPC471721
0.7944 Intermediate Similarity NPC326664
0.7941 Intermediate Similarity NPC329282
0.7921 Intermediate Similarity NPC222390
0.7921 Intermediate Similarity NPC244427
0.7917 Intermediate Similarity NPC125226
0.789 Intermediate Similarity NPC158157
0.7885 Intermediate Similarity NPC472701
0.7885 Intermediate Similarity NPC472683
0.7885 Intermediate Similarity NPC472696
0.7885 Intermediate Similarity NPC472695
0.787 Intermediate Similarity NPC215419
0.7865 Intermediate Similarity NPC103488
0.785 Intermediate Similarity NPC143768
0.7843 Intermediate Similarity NPC329556
0.781 Intermediate Similarity NPC192577
0.7802 Intermediate Similarity NPC73978
0.7802 Intermediate Similarity NPC100039
0.7778 Intermediate Similarity NPC272260
0.7757 Intermediate Similarity NPC292834
0.7753 Intermediate Similarity NPC9796
0.7748 Intermediate Similarity NPC318173
0.7701 Intermediate Similarity NPC285679
0.7679 Intermediate Similarity NPC202015
0.7664 Intermediate Similarity NPC474057
0.7664 Intermediate Similarity NPC137315
0.7647 Intermediate Similarity NPC112552
0.7642 Intermediate Similarity NPC318327
0.7629 Intermediate Similarity NPC58872
0.7593 Intermediate Similarity NPC66208
0.7586 Intermediate Similarity NPC74458
0.7568 Intermediate Similarity NPC469843
0.7556 Intermediate Similarity NPC179726
0.7549 Intermediate Similarity NPC221825
0.7545 Intermediate Similarity NPC217111
0.7528 Intermediate Similarity NPC307195
0.7525 Intermediate Similarity NPC156021
0.7524 Intermediate Similarity NPC471186
0.7523 Intermediate Similarity NPC13784
0.75 Intermediate Similarity NPC477703
0.75 Intermediate Similarity NPC291799
0.75 Intermediate Similarity NPC222968
0.75 Intermediate Similarity NPC80605
0.75 Intermediate Similarity NPC323440
0.7476 Intermediate Similarity NPC133809
0.7476 Intermediate Similarity NPC128248
0.7476 Intermediate Similarity NPC136810
0.7474 Intermediate Similarity NPC123476
0.7456 Intermediate Similarity NPC232958
0.7453 Intermediate Similarity NPC37914
0.7453 Intermediate Similarity NPC83409
0.7453 Intermediate Similarity NPC185763
0.7449 Intermediate Similarity NPC110420
0.7449 Intermediate Similarity NPC67585
0.7449 Intermediate Similarity NPC26224
0.7449 Intermediate Similarity NPC303967
0.7447 Intermediate Similarity NPC149263
0.7447 Intermediate Similarity NPC324624
0.7436 Intermediate Similarity NPC142956
0.7431 Intermediate Similarity NPC218855
0.7426 Intermediate Similarity NPC12695
0.7416 Intermediate Similarity NPC96835
0.7416 Intermediate Similarity NPC258492
0.7391 Intermediate Similarity NPC144547
0.7387 Intermediate Similarity NPC474095
0.7387 Intermediate Similarity NPC186933
0.7387 Intermediate Similarity NPC228936
0.7386 Intermediate Similarity NPC87099
0.7386 Intermediate Similarity NPC39799
0.7386 Intermediate Similarity NPC280135
0.7386 Intermediate Similarity NPC226999
0.7386 Intermediate Similarity NPC135433
0.7386 Intermediate Similarity NPC1008
0.7386 Intermediate Similarity NPC193578
0.7386 Intermediate Similarity NPC158028
0.7383 Intermediate Similarity NPC112903
0.7368 Intermediate Similarity NPC476645
0.7364 Intermediate Similarity NPC471481
0.7358 Intermediate Similarity NPC105899
0.7358 Intermediate Similarity NPC167336
0.7356 Intermediate Similarity NPC98880
0.7353 Intermediate Similarity NPC226041
0.735 Intermediate Similarity NPC318067
0.7345 Intermediate Similarity NPC228318
0.7339 Intermediate Similarity NPC210089
0.7333 Intermediate Similarity NPC255676
0.7328 Intermediate Similarity NPC167323
0.7328 Intermediate Similarity NPC269923
0.7327 Intermediate Similarity NPC172925
0.7321 Intermediate Similarity NPC135730
0.7321 Intermediate Similarity NPC62138
0.7312 Intermediate Similarity NPC157055
0.7308 Intermediate Similarity NPC225079
0.7304 Intermediate Similarity NPC289432
0.7304 Intermediate Similarity NPC988
0.7297 Intermediate Similarity NPC130591
0.7297 Intermediate Similarity NPC241851
0.7297 Intermediate Similarity NPC234637
0.7283 Intermediate Similarity NPC137847
0.7283 Intermediate Similarity NPC76455
0.7273 Intermediate Similarity NPC79496
0.7273 Intermediate Similarity NPC95289
0.7273 Intermediate Similarity NPC72670
0.7273 Intermediate Similarity NPC212415
0.7253 Intermediate Similarity NPC78500
0.7245 Intermediate Similarity NPC473345
0.7241 Intermediate Similarity NPC311343
0.7241 Intermediate Similarity NPC472981
0.7238 Intermediate Similarity NPC25458
0.7232 Intermediate Similarity NPC470764
0.7228 Intermediate Similarity NPC34243
0.7222 Intermediate Similarity NPC470391
0.7204 Intermediate Similarity NPC159661
0.7203 Intermediate Similarity NPC328107
0.7203 Intermediate Similarity NPC85511
0.719 Intermediate Similarity NPC282923
0.7188 Intermediate Similarity NPC267704
0.7184 Intermediate Similarity NPC240042
0.7184 Intermediate Similarity NPC103048
0.7179 Intermediate Similarity NPC120545
0.7174 Intermediate Similarity NPC298023

  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 NPC289883 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
0.9091 High Similarity NPD650 Approved
0.9032 High Similarity NPD3495 Discontinued
0.8901 High Similarity NPD7609 Phase 3
0.8804 High Similarity NPD7631 Approved
0.8621 High Similarity NPD942 Approved
0.8602 High Similarity NPD1508 Approved
0.8333 Intermediate Similarity NPD1843 Approved
0.809 Intermediate Similarity NPD1507 Clinical (unspecified phase)
0.7921 Intermediate Similarity NPD1932 Approved
0.7843 Intermediate Similarity NPD1929 Approved
0.7843 Intermediate Similarity NPD1930 Approved
0.7843 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD5951 Approved
0.7664 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7642 Intermediate Similarity NPD2329 Discontinued
0.7549 Intermediate Similarity NPD2066 Phase 3
0.75 Intermediate Similarity NPD506 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD5836 Discontinued
0.7345 Intermediate Similarity NPD7610 Discontinued
0.7327 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD4879 Approved
0.7238 Intermediate Similarity NPD2648 Phase 3
0.7238 Intermediate Similarity NPD2193 Phase 2
0.7228 Intermediate Similarity NPD1563 Approved
0.72 Intermediate Similarity NPD1239 Approved
0.7143 Intermediate Similarity NPD1087 Approved
0.713 Intermediate Similarity NPD7009 Phase 2
0.7103 Intermediate Similarity NPD1237 Approved
0.7087 Intermediate Similarity NPD1989 Approved
0.7075 Intermediate Similarity NPD2196 Discontinued
0.7059 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1202 Approved
0.7019 Intermediate Similarity NPD1564 Approved
0.7019 Intermediate Similarity NPD1566 Phase 3
0.7019 Intermediate Similarity NPD1565 Approved
0.7009 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.699 Remote Similarity NPD1693 Approved
0.699 Remote Similarity NPD6048 Clinical (unspecified phase)
0.699 Remote Similarity NPD6049 Phase 2
0.699 Remote Similarity NPD4094 Approved
0.6949 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6944 Remote Similarity NPD164 Approved
0.6942 Remote Similarity NPD1470 Approved
0.6937 Remote Similarity NPD1317 Discontinued
0.6931 Remote Similarity NPD1090 Approved
0.6931 Remote Similarity NPD1086 Approved
0.6931 Remote Similarity NPD1089 Approved
0.6907 Remote Similarity NPD3971 Phase 1
0.6903 Remote Similarity NPD6858 Approved
0.6903 Remote Similarity NPD7094 Approved
0.6891 Remote Similarity NPD1201 Approved
0.6881 Remote Similarity NPD2197 Approved
0.6881 Remote Similarity NPD1677 Discontinued
0.6881 Remote Similarity NPD2192 Approved
0.6857 Remote Similarity NPD1100 Approved
0.6857 Remote Similarity NPD1099 Approved
0.6857 Remote Similarity NPD4655 Approved
0.6857 Remote Similarity NPD4657 Approved
0.6855 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6855 Remote Similarity NPD7008 Discontinued
0.6847 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6833 Remote Similarity NPD4878 Approved
0.6832 Remote Similarity NPD800 Approved
0.6796 Remote Similarity NPD1088 Approved
0.6789 Remote Similarity NPD5909 Discontinued
0.6786 Remote Similarity NPD664 Approved
0.6759 Remote Similarity NPD6027 Approved
0.6759 Remote Similarity NPD6024 Approved
0.6759 Remote Similarity NPD2171 Approved
0.6746 Remote Similarity NPD1874 Clinical (unspecified phase)
0.6737 Remote Similarity NPD225 Approved
0.6737 Remote Similarity NPD227 Approved
0.6729 Remote Similarity NPD1238 Approved
0.6726 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6724 Remote Similarity NPD3317 Approved
0.6723 Remote Similarity NPD2345 Approved
0.6721 Remote Similarity NPD6330 Clinical (unspecified phase)
0.67 Remote Similarity NPD9259 Approved
0.67 Remote Similarity NPD9257 Approved
0.6697 Remote Similarity NPD3357 Discontinued
0.6696 Remote Similarity NPD2182 Approved
0.6667 Remote Similarity NPD9490 Approved
0.6638 Remote Similarity NPD2508 Discontinued
0.6636 Remote Similarity NPD2577 Clinical (unspecified phase)
0.6615 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6614 Remote Similarity NPD7961 Discontinued
0.6606 Remote Similarity NPD813 Approved
0.66 Remote Similarity NPD5734 Clinical (unspecified phase)
0.6591 Remote Similarity NPD675 Discontinued
0.6587 Remote Similarity NPD2754 Discontinued
0.6585 Remote Similarity NPD1876 Approved
0.6566 Remote Similarity NPD9491 Approved
0.6557 Remote Similarity NPD3972 Approved
0.6531 Remote Similarity NPD226 Approved
0.65 Remote Similarity NPD4544 Approved
0.65 Remote Similarity NPD1651 Approved
0.65 Remote Similarity NPD1245 Approved
0.6475 Remote Similarity NPD6287 Discontinued
0.6471 Remote Similarity NPD997 Clinical (unspecified phase)
0.6452 Remote Similarity NPD1482 Clinical (unspecified phase)
0.6444 Remote Similarity NPD8239 Clinical (unspecified phase)
0.6442 Remote Similarity NPD3673 Approved
0.6442 Remote Similarity NPD9256 Approved
0.6442 Remote Similarity NPD9258 Approved
0.6442 Remote Similarity NPD3672 Approved
0.6422 Remote Similarity NPD7798 Approved
0.6421 Remote Similarity NPD9716 Approved
0.6406 Remote Similarity NPD5422 Clinical (unspecified phase)
0.6393 Remote Similarity NPD3836 Clinical (unspecified phase)
0.6391 Remote Similarity NPD2346 Discontinued
0.6387 Remote Similarity NPD405 Clinical (unspecified phase)
0.6371 Remote Similarity NPD182 Clinical (unspecified phase)
0.6364 Remote Similarity NPD3024 Approved
0.6364 Remote Similarity NPD3025 Approved
0.6357 Remote Similarity NPD7713 Phase 3
0.6356 Remote Similarity NPD1246 Approved
0.6349 Remote Similarity NPD4980 Approved
0.6346 Remote Similarity NPD5347 Phase 2
0.6346 Remote Similarity NPD5346 Phase 2
0.6341 Remote Similarity NPD1281 Approved
0.633 Remote Similarity NPD466 Approved
0.6328 Remote Similarity NPD6966 Discovery
0.6316 Remote Similarity NPD5404 Approved
0.6316 Remote Similarity NPD5405 Approved
0.6316 Remote Similarity NPD5408 Approved
0.6316 Remote Similarity NPD5406 Approved
0.6311 Remote Similarity NPD3019 Approved
0.6311 Remote Similarity NPD4793 Discontinued
0.6273 Remote Similarity NPD742 Approved
0.6271 Remote Similarity NPD7076 Approved
0.6271 Remote Similarity NPD7077 Approved
0.627 Remote Similarity NPD3245 Phase 3
0.627 Remote Similarity NPD5653 Discontinued
0.627 Remote Similarity NPD3244 Pre-registration
0.626 Remote Similarity NPD3023 Approved
0.626 Remote Similarity NPD3026 Approved
0.625 Remote Similarity NPD7003 Approved
0.624 Remote Similarity NPD5157 Phase 1
0.624 Remote Similarity NPD3547 Approved
0.624 Remote Similarity NPD5159 Phase 2
0.624 Remote Similarity NPD5158 Clinical (unspecified phase)
0.624 Remote Similarity NPD3549 Approved
0.624 Remote Similarity NPD3550 Clinical (unspecified phase)
0.6237 Remote Similarity NPD9497 Clinical (unspecified phase)
0.623 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6226 Remote Similarity NPD1007 Discontinued
0.622 Remote Similarity NPD2798 Approved
0.6216 Remote Similarity NPD3135 Clinical (unspecified phase)
0.6216 Remote Similarity NPD6354 Discontinued
0.621 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6204 Remote Similarity NPD9260 Approved
0.6198 Remote Similarity NPD6065 Approved
0.619 Remote Similarity NPD1283 Approved
0.619 Remote Similarity NPD1574 Approved
0.6179 Remote Similarity NPD2932 Approved
0.6179 Remote Similarity NPD4199 Phase 3
0.616 Remote Similarity NPD3355 Approved
0.616 Remote Similarity NPD3356 Approved
0.616 Remote Similarity NPD3880 Clinical (unspecified phase)
0.6154 Remote Similarity NPD3764 Approved
0.6154 Remote Similarity NPD2846 Clinical (unspecified phase)
0.6148 Remote Similarity NPD1471 Phase 3
0.6147 Remote Similarity NPD3093 Approved
0.6147 Remote Similarity NPD5206 Clinical (unspecified phase)
0.6147 Remote Similarity NPD2895 Discontinued
0.6146 Remote Similarity NPD4058 Approved
0.6142 Remote Similarity NPD1593 Approved
0.6142 Remote Similarity NPD1164 Approved
0.6127 Remote Similarity NPD3226 Approved
0.6115 Remote Similarity NPD8165 Discontinued
0.6106 Remote Similarity NPD6647 Phase 2
0.6106 Remote Similarity NPD5700 Clinical (unspecified phase)
0.61 Remote Similarity NPD3981 Approved
0.61 Remote Similarity NPD3903 Approved
0.61 Remote Similarity NPD3904 Approved
0.61 Remote Similarity NPD3979 Approved
0.6098 Remote Similarity NPD1217 Clinical (unspecified phase)
0.6091 Remote Similarity NPD5598 Approved
0.6091 Remote Similarity NPD5597 Approved
0.6083 Remote Similarity NPD690 Clinical (unspecified phase)
0.6083 Remote Similarity NPD2319 Discontinued
0.6071 Remote Similarity NPD5630 Phase 1
0.6048 Remote Similarity NPD1727 Approved
0.6047 Remote Similarity NPD7084 Phase 3
0.6045 Remote Similarity NPD7541 Clinical (unspecified phase)
0.6045 Remote Similarity NPD4705 Clinical (unspecified phase)
0.6036 Remote Similarity NPD5926 Approved
0.6034 Remote Similarity NPD2342 Discontinued
0.6031 Remote Similarity NPD2313 Discontinued
0.6029 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6019 Remote Similarity NPD4407 Approved
0.6019 Remote Similarity NPD4405 Approved
0.6019 Remote Similarity NPD4408 Approved
0.6018 Remote Similarity NPD4803 Discontinued
0.6018 Remote Similarity NPD4321 Approved
0.6 Remote Similarity NPD5048 Discontinued
0.6 Remote Similarity NPD7390 Discontinued
0.6 Remote Similarity NPD6010 Discontinued

  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