Structure

Physi-Chem Properties

Molecular Weight:  410.21
Volume:  444.066
LogP:  5.67
LogD:  3.086
LogS:  -3.741
# Rotatable Bonds:  8
TPSA:  97.99
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.376
Synthetic Accessibility Score:  3.412
Fsp3:  0.32
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.92
MDCK Permeability:  1.4242598808777984e-05
Pgp-inhibitor:  0.779
Pgp-substrate:  0.192
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.975
30% Bioavailability (F30%):  0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.016
Plasma Protein Binding (PPB):  98.61095428466797%
Volume Distribution (VD):  0.429
Pgp-substrate:  2.127467632293701%

ADMET: Metabolism

CYP1A2-inhibitor:  0.389
CYP1A2-substrate:  0.149
CYP2C19-inhibitor:  0.635
CYP2C19-substrate:  0.083
CYP2C9-inhibitor:  0.822
CYP2C9-substrate:  0.902
CYP2D6-inhibitor:  0.776
CYP2D6-substrate:  0.37
CYP3A4-inhibitor:  0.317
CYP3A4-substrate:  0.216

ADMET: Excretion

Clearance (CL):  14.738
Half-life (T1/2):  0.536

ADMET: Toxicity

hERG Blockers:  0.029
Human Hepatotoxicity (H-HT):  0.647
Drug-inuced Liver Injury (DILI):  0.04
AMES Toxicity:  0.016
Rat Oral Acute Toxicity:  0.216
Maximum Recommended Daily Dose:  0.157
Skin Sensitization:  0.927
Carcinogencity:  0.063
Eye Corrosion:  0.003
Eye Irritation:  0.168
Respiratory Toxicity:  0.067

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  Natural Product: NPC70853

Natural Product ID:  NPC70853
Common Name*:   Tetramethylluteolin
IUPAC Name:   2-(3,4-dimethoxyphenyl)-5,7-dimethoxychromen-4-one
Synonyms:   3',4',5,7-Tetramethoxyflavone; Tetramethylluteolin
Standard InCHIKey:  CLXVBVLQKLQNRQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H18O6/c1-21-12-8-17(24-4)19-13(20)10-15(25-18(19)9-12)11-5-6-14(22-2)16(7-11)23-3/h5-10H,1-4H3
SMILES:  COc1cc(OC)c2c(c1)oc(cc2=O)c1ccc(c(c1)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL327340
PubChem CID:   631170
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002585] O-methylated flavonoids
          • [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota roots n.a. n.a. PMID[10514313]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. root n.a. PMID[10514313]
NPO27986 Lonchocarpus chiricanus Species Fabaceae Eukaryota Root barks n.a. n.a. PMID[11421729]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota roots n.a. n.a. PMID[11575962]
NPO27695 Centaurea sonchifolia Species n.a. n.a. n.a. n.a. n.a. PMID[1624943]
NPO27600 Boesenbergia pandurata Species Zingiberaceae Eukaryota rhizomes Pindaya Township, Shan State, Myanmar 2004-NOV PMID[17896818]
NPO27600 Boesenbergia pandurata Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[27508308]
NPO27600 Boesenbergia pandurata Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[28099006]
NPO19745 Esox lucius Species Esocidae Eukaryota n.a. n.a. n.a. PMID[3349210]
NPO28159 Rubia akane Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[8176404]
NPO19745 Esox lucius Species Esocidae Eukaryota n.a. n.a. Database[FooDB]
NPO19745 Esox lucius Species Esocidae Eukaryota n.a. n.a. Database[FooDB]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22500 Stephania dielsiana Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21600 Aconitum variegatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22500 Stephania dielsiana Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23156 Maclura cochinchinensis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27397 Drymaria cordata Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21600 Aconitum variegatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27882 Boswellia ovalifoliolata Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21600 Aconitum variegatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28159 Rubia akane Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27057 Matsucoccus josephi Species Margarodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4164 Salvia virgata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27145 Euphorbia hylonoma Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27916 Hardenbergia violacea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28003 Astragalus circassicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21600 Aconitum variegatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28289 Nepytia freemani Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26476 Preussia terricola Species Sporormiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19383 Lactarius mitissimus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28385 Iris kashmiriana Species Tarachodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21344 Fadogia agrestis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28426 Etmopterus spinax Species Etmopteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27455 Dysidea fragilis Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27882 Boswellia ovalifoliolata Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28412 Amorphophallus konjac Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27234 Thalassiosira weissflogii Species Thalassiosiraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27986 Lonchocarpus chiricanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27338 Senecio platyphylloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2030 Mimosa pigra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26553 Lemonia spectabilis Species Lemoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28063 Beilschmiedia madang Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27816 Pterocaulon serrulatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25499 Campanula choziatowskyi Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26321 Salvia patens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26342 Dialium excelsum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27613 Helleborus macranthus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17337 Centaurea scoparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28044 Erythrina hypaphorus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16298 Quercus marilandica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27637 Heliotropium scabrum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28313 Mentzelia decapetala Species Loasaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16156 Mucuna holtonii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25835 Parmotrema nilgherrense Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8961 Bethencourtia palmensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28206 Aniba santalodora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5970.1 Petunia axillaris subsp. parodii Subspecies Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19745 Esox lucius Species Esocidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27397 Drymaria cordata Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28083 Salvia lavanduloides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11849 Cynoglossum macrostylum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27702 Matricaria sabulosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23156 Maclura cochinchinensis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27506 Orgyia pseudotsugata Species Lymantriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27854 Sphaeria rousseliana n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO22500 Stephania dielsiana Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27600 Boesenbergia pandurata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9354 Lepechinia urbanii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1184 Colchicum filifolium Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27614 Salix rosmarinifolia Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21534 Ostrya carpinifolia Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27695 Centaurea sonchifolia Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27642 Podocarpus dacrydioides Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20584 Cheilanthes fragrans Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28159 Rubia akane 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
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 7.4 % PMID[549995]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 3.1 % PMID[549995]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 2.6 % PMID[549995]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = -15.3 % PMID[549995]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 73940.0 nM PMID[549997]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 32500.0 nM PMID[549997]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 3130.0 nM PMID[549997]
NPT113 Cell Line RAW264.7 Mus musculus Activity = 108.54 % PMID[549997]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 37.59 % PMID[549997]
NPT2 Others Unspecified Inhibition = 124.05 % PMID[549996]

☑ 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 NPC70853 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC9966
0.9927 High Similarity NPC113089
0.9926 High Similarity NPC29536
0.9855 High Similarity NPC136278
0.9784 High Similarity NPC106461
0.9784 High Similarity NPC40818
0.9784 High Similarity NPC14958
0.9784 High Similarity NPC110639
0.9784 High Similarity NPC310259
0.9784 High Similarity NPC215932
0.9714 High Similarity NPC85233
0.9714 High Similarity NPC299923
0.9714 High Similarity NPC205522
0.9712 High Similarity NPC471590
0.9645 High Similarity NPC195202
0.9645 High Similarity NPC261548
0.9643 High Similarity NPC302408
0.9643 High Similarity NPC283002
0.964 High Similarity NPC23955
0.964 High Similarity NPC293201
0.9577 High Similarity NPC69752
0.9574 High Similarity NPC12200
0.9574 High Similarity NPC33265
0.9574 High Similarity NPC62536
0.9571 High Similarity NPC165512
0.951 High Similarity NPC50728
0.951 High Similarity NPC201547
0.951 High Similarity NPC259058
0.951 High Similarity NPC166753
0.9507 High Similarity NPC63256
0.9507 High Similarity NPC10304
0.9507 High Similarity NPC476342
0.9496 High Similarity NPC185607
0.9496 High Similarity NPC124467
0.9496 High Similarity NPC214919
0.9489 High Similarity NPC44573
0.9444 High Similarity NPC472535
0.9444 High Similarity NPC236769
0.9444 High Similarity NPC474170
0.9444 High Similarity NPC474388
0.9444 High Similarity NPC308451
0.9444 High Similarity NPC226973
0.9444 High Similarity NPC208043
0.9441 High Similarity NPC328119
0.9441 High Similarity NPC52005
0.9441 High Similarity NPC48479
0.9441 High Similarity NPC181250
0.9441 High Similarity NPC183950
0.9441 High Similarity NPC177298
0.9441 High Similarity NPC159103
0.9441 High Similarity NPC238366
0.9441 High Similarity NPC137062
0.9441 High Similarity NPC287101
0.9441 High Similarity NPC223579
0.9437 High Similarity NPC470511
0.9437 High Similarity NPC117463
0.9379 High Similarity NPC40033
0.9379 High Similarity NPC39732
0.9379 High Similarity NPC60972
0.9379 High Similarity NPC134677
0.9375 High Similarity NPC189270
0.9375 High Similarity NPC5840
0.9375 High Similarity NPC219330
0.9375 High Similarity NPC177839
0.9375 High Similarity NPC306821
0.9371 High Similarity NPC120464
0.9366 High Similarity NPC231013
0.9366 High Similarity NPC120924
0.9366 High Similarity NPC195919
0.9366 High Similarity NPC216314
0.9343 High Similarity NPC77955
0.9315 High Similarity NPC472408
0.9315 High Similarity NPC236223
0.9315 High Similarity NPC86485
0.9315 High Similarity NPC183878
0.9315 High Similarity NPC179126
0.9315 High Similarity NPC274327
0.9315 High Similarity NPC231018
0.9315 High Similarity NPC270620
0.9315 High Similarity NPC78326
0.9315 High Similarity NPC176775
0.9315 High Similarity NPC186507
0.9315 High Similarity NPC69394
0.9315 High Similarity NPC47781
0.9315 High Similarity NPC145379
0.9315 High Similarity NPC160951
0.9315 High Similarity NPC22519
0.9315 High Similarity NPC255350
0.931 High Similarity NPC252933
0.931 High Similarity NPC125062
0.931 High Similarity NPC200740
0.931 High Similarity NPC54394
0.931 High Similarity NPC76376
0.9301 High Similarity NPC108406
0.9291 High Similarity NPC476054
0.9286 High Similarity NPC58229
0.9265 High Similarity NPC473655
0.9265 High Similarity NPC101294
0.9252 High Similarity NPC241774
0.9252 High Similarity NPC146165
0.9252 High Similarity NPC32557
0.9252 High Similarity NPC92659
0.9252 High Similarity NPC256612
0.9252 High Similarity NPC50715
0.9252 High Similarity NPC2476
0.9252 High Similarity NPC20830
0.9252 High Similarity NPC183597
0.9252 High Similarity NPC128863
0.9252 High Similarity NPC227325
0.9252 High Similarity NPC138360
0.9252 High Similarity NPC189960
0.9252 High Similarity NPC167815
0.9252 High Similarity NPC34725
0.9252 High Similarity NPC163780
0.9252 High Similarity NPC122623
0.9252 High Similarity NPC280339
0.9252 High Similarity NPC4455
0.9252 High Similarity NPC213622
0.9252 High Similarity NPC201136
0.9252 High Similarity NPC284353
0.9252 High Similarity NPC196439
0.9252 High Similarity NPC276059
0.9247 High Similarity NPC188203
0.9247 High Similarity NPC222830
0.9247 High Similarity NPC120163
0.9247 High Similarity NPC241498
0.9247 High Similarity NPC198826
0.9247 High Similarity NPC292460
0.9247 High Similarity NPC57030
0.9247 High Similarity NPC212678
0.9247 High Similarity NPC83508
0.9247 High Similarity NPC71334
0.9247 High Similarity NPC100887
0.9247 High Similarity NPC166201
0.9247 High Similarity NPC301323
0.9247 High Similarity NPC275836
0.9247 High Similarity NPC239128
0.9247 High Similarity NPC25270
0.9247 High Similarity NPC131624
0.9247 High Similarity NPC275722
0.9247 High Similarity NPC279989
0.9247 High Similarity NPC156222
0.9247 High Similarity NPC55205
0.9247 High Similarity NPC293183
0.9247 High Similarity NPC256283
0.9247 High Similarity NPC82325
0.9247 High Similarity NPC162313
0.9247 High Similarity NPC187498
0.9247 High Similarity NPC68882
0.9247 High Similarity NPC301123
0.9247 High Similarity NPC471982
0.9241 High Similarity NPC338131
0.9225 High Similarity NPC182842
0.9191 High Similarity NPC278556
0.9189 High Similarity NPC265511
0.9189 High Similarity NPC49824
0.9189 High Similarity NPC257277
0.9189 High Similarity NPC178854
0.9184 High Similarity NPC162351
0.9184 High Similarity NPC246204
0.9184 High Similarity NPC58382
0.9184 High Similarity NPC75279
0.9184 High Similarity NPC280937
0.9184 High Similarity NPC128961
0.9184 High Similarity NPC473664
0.9184 High Similarity NPC472915
0.9184 High Similarity NPC476289
0.9184 High Similarity NPC250822
0.9184 High Similarity NPC279930
0.9184 High Similarity NPC18727
0.9184 High Similarity NPC276409
0.9178 High Similarity NPC50403
0.9178 High Similarity NPC133953
0.9178 High Similarity NPC28274
0.9178 High Similarity NPC117579
0.9172 High Similarity NPC474648
0.9172 High Similarity NPC270465
0.9172 High Similarity NPC87125
0.9167 High Similarity NPC474999
0.9155 High Similarity NPC119663
0.9137 High Similarity NPC61546
0.9137 High Similarity NPC254741
0.9137 High Similarity NPC72452
0.9128 High Similarity NPC189179
0.9128 High Similarity NPC470402
0.9128 High Similarity NPC473272
0.9128 High Similarity NPC183
0.9128 High Similarity NPC476981
0.9128 High Similarity NPC63454
0.9128 High Similarity NPC284820
0.9128 High Similarity NPC19097
0.9128 High Similarity NPC227192
0.9128 High Similarity NPC203891
0.9128 High Similarity NPC93376
0.9128 High Similarity NPC101830
0.9128 High Similarity NPC75215
0.9128 High Similarity NPC110070
0.9128 High Similarity NPC183851
0.9128 High Similarity NPC224137
0.9122 High Similarity NPC26227

  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 NPC70853 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
0.9315 High Similarity NPD2801 Approved
0.9252 High Similarity NPD3817 Phase 2
0.9116 High Similarity NPD1934 Approved
0.9091 High Similarity NPD1511 Approved
0.9 High Similarity NPD2796 Approved
0.8966 High Similarity NPD1512 Approved
0.8926 High Similarity NPD2393 Clinical (unspecified phase)
0.8882 High Similarity NPD5494 Approved
0.8808 High Similarity NPD3882 Suspended
0.8767 High Similarity NPD4378 Clinical (unspecified phase)
0.8654 High Similarity NPD6166 Phase 2
0.8654 High Similarity NPD6168 Clinical (unspecified phase)
0.8654 High Similarity NPD6167 Clinical (unspecified phase)
0.8608 High Similarity NPD7054 Approved
0.8571 High Similarity NPD6799 Approved
0.8553 High Similarity NPD7472 Approved
0.8544 High Similarity NPD3818 Discontinued
0.8471 Intermediate Similarity NPD3926 Phase 2
0.8462 Intermediate Similarity NPD1247 Approved
0.8452 Intermediate Similarity NPD919 Approved
0.8438 Intermediate Similarity NPD7074 Phase 3
0.8414 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8414 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8403 Intermediate Similarity NPD1510 Phase 2
0.84 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8395 Intermediate Similarity NPD7808 Phase 3
0.8385 Intermediate Similarity NPD6797 Phase 2
0.8356 Intermediate Similarity NPD1549 Phase 2
0.8355 Intermediate Similarity NPD4380 Phase 2
0.8333 Intermediate Similarity NPD7251 Discontinued
0.8312 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8312 Intermediate Similarity NPD7819 Suspended
0.8291 Intermediate Similarity NPD6232 Discontinued
0.8282 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8269 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8267 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8252 Intermediate Similarity NPD1240 Approved
0.825 Intermediate Similarity NPD7473 Discontinued
0.8247 Intermediate Similarity NPD6801 Discontinued
0.8235 Intermediate Similarity NPD6599 Discontinued
0.8205 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8194 Intermediate Similarity NPD1933 Approved
0.8153 Intermediate Similarity NPD7075 Discontinued
0.8151 Intermediate Similarity NPD3748 Approved
0.8141 Intermediate Similarity NPD5402 Approved
0.8138 Intermediate Similarity NPD1607 Approved
0.8108 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8065 Intermediate Similarity NPD7411 Suspended
0.8054 Intermediate Similarity NPD1243 Approved
0.8039 Intermediate Similarity NPD5403 Approved
0.8039 Intermediate Similarity NPD920 Approved
0.8037 Intermediate Similarity NPD5844 Phase 1
0.8026 Intermediate Similarity NPD5401 Approved
0.8025 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7945 Intermediate Similarity NPD447 Suspended
0.7927 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD6959 Discontinued
0.7881 Intermediate Similarity NPD3750 Approved
0.7877 Intermediate Similarity NPD943 Approved
0.7848 Intermediate Similarity NPD1465 Phase 2
0.7847 Intermediate Similarity NPD6832 Phase 2
0.7823 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD5536 Phase 2
0.7733 Intermediate Similarity NPD1551 Phase 2
0.7733 Intermediate Similarity NPD2935 Discontinued
0.773 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD2654 Approved
0.7697 Intermediate Similarity NPD2800 Approved
0.7683 Intermediate Similarity NPD5242 Approved
0.7679 Intermediate Similarity NPD6559 Discontinued
0.7669 Intermediate Similarity NPD7199 Phase 2
0.7655 Intermediate Similarity NPD3018 Phase 2
0.7655 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD7768 Phase 2
0.7636 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD1613 Approved
0.7619 Intermediate Similarity NPD2313 Discontinued
0.761 Intermediate Similarity NPD6385 Approved
0.761 Intermediate Similarity NPD6386 Approved
0.7593 Intermediate Similarity NPD3749 Approved
0.7586 Intermediate Similarity NPD2798 Approved
0.7584 Intermediate Similarity NPD230 Phase 1
0.7578 Intermediate Similarity NPD5353 Approved
0.7576 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD2534 Approved
0.7564 Intermediate Similarity NPD2532 Approved
0.7564 Intermediate Similarity NPD2533 Approved
0.7552 Intermediate Similarity NPD2981 Phase 2
0.7551 Intermediate Similarity NPD3027 Phase 3
0.755 Intermediate Similarity NPD2799 Discontinued
0.7532 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD4628 Phase 3
0.753 Intermediate Similarity NPD2403 Approved
0.7517 Intermediate Similarity NPD3267 Approved
0.7517 Intermediate Similarity NPD3266 Approved
0.75 Intermediate Similarity NPD2982 Phase 2
0.75 Intermediate Similarity NPD6100 Approved
0.75 Intermediate Similarity NPD2983 Phase 2
0.75 Intermediate Similarity NPD6099 Approved
0.7484 Intermediate Similarity NPD3226 Approved
0.7465 Intermediate Similarity NPD17 Approved
0.7451 Intermediate Similarity NPD2344 Approved
0.7451 Intermediate Similarity NPD2346 Discontinued
0.7434 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD3972 Approved
0.7427 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD6651 Approved
0.741 Intermediate Similarity NPD3787 Discontinued
0.74 Intermediate Similarity NPD4307 Phase 2
0.7397 Intermediate Similarity NPD1203 Approved
0.7389 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD3268 Approved
0.7383 Intermediate Similarity NPD1296 Phase 2
0.7379 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD1019 Discontinued
0.7346 Intermediate Similarity NPD37 Approved
0.7338 Intermediate Similarity NPD5283 Phase 1
0.7338 Intermediate Similarity NPD1241 Discontinued
0.7337 Intermediate Similarity NPD3751 Discontinued
0.7324 Intermediate Similarity NPD1548 Phase 1
0.732 Intermediate Similarity NPD7033 Discontinued
0.732 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD4966 Approved
0.7317 Intermediate Similarity NPD5019 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD4967 Phase 2
0.7317 Intermediate Similarity NPD4965 Approved
0.7312 Intermediate Similarity NPD1653 Approved
0.731 Intermediate Similarity NPD1608 Approved
0.731 Intermediate Similarity NPD5953 Discontinued
0.731 Intermediate Similarity NPD9717 Approved
0.7297 Intermediate Similarity NPD9494 Approved
0.7296 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD7286 Phase 2
0.7279 Intermediate Similarity NPD2797 Approved
0.7278 Intermediate Similarity NPD7390 Discontinued
0.7261 Intermediate Similarity NPD2309 Approved
0.7248 Intermediate Similarity NPD4908 Phase 1
0.7241 Intermediate Similarity NPD422 Phase 1
0.7239 Intermediate Similarity NPD6844 Discontinued
0.7233 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD3146 Approved
0.7229 Intermediate Similarity NPD6234 Discontinued
0.7226 Intermediate Similarity NPD1471 Phase 3
0.7211 Intermediate Similarity NPD3225 Approved
0.7208 Intermediate Similarity NPD4308 Phase 3
0.7197 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD4357 Discontinued
0.7161 Intermediate Similarity NPD3539 Phase 1
0.7152 Intermediate Similarity NPD3887 Approved
0.7152 Intermediate Similarity NPD4288 Approved
0.7152 Intermediate Similarity NPD6190 Approved
0.7152 Intermediate Similarity NPD411 Approved
0.7152 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6798 Discontinued
0.7134 Intermediate Similarity NPD1652 Phase 2
0.7133 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD1610 Phase 2
0.7115 Intermediate Similarity NPD3540 Phase 1
0.7115 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD2353 Approved
0.7111 Intermediate Similarity NPD4360 Phase 2
0.7111 Intermediate Similarity NPD4363 Phase 3
0.7105 Intermediate Similarity NPD6233 Phase 2
0.7101 Intermediate Similarity NPD7229 Phase 3
0.7095 Intermediate Similarity NPD1876 Approved
0.7073 Intermediate Similarity NPD5890 Approved
0.7073 Intermediate Similarity NPD5889 Approved
0.7069 Intermediate Similarity NPD7685 Pre-registration
0.7066 Intermediate Similarity NPD6971 Discontinued
0.7059 Intermediate Similarity NPD3140 Approved
0.7059 Intermediate Similarity NPD3142 Approved
0.7048 Intermediate Similarity NPD5978 Approved
0.7048 Intermediate Similarity NPD5977 Approved
0.7044 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD2163 Approved
0.7034 Intermediate Similarity NPD9268 Approved
0.7034 Intermediate Similarity NPD1651 Approved
0.7033 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD6279 Approved
0.703 Intermediate Similarity NPD6280 Approved
0.7027 Intermediate Similarity NPD5005 Approved
0.7027 Intermediate Similarity NPD5006 Approved
0.7019 Intermediate Similarity NPD4662 Approved
0.7019 Intermediate Similarity NPD4661 Approved
0.7013 Intermediate Similarity NPD6355 Discontinued
0.7012 Intermediate Similarity NPD6585 Discontinued
0.7007 Intermediate Similarity NPD3705 Approved
0.7006 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5710 Approved

  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