Structure

Physi-Chem Properties

Molecular Weight:  286.08
Volume:  285.119
LogP:  2.116
LogD:  2.244
LogS:  -3.869
# Rotatable Bonds:  2
TPSA:  75.99
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.887
Synthetic Accessibility Score:  2.798
Fsp3:  0.188
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.613
MDCK Permeability:  1.75498025782872e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.012
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.845

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.096
Plasma Protein Binding (PPB):  81.20582580566406%
Volume Distribution (VD):  0.766
Pgp-substrate:  12.85120677947998%

ADMET: Metabolism

CYP1A2-inhibitor:  0.889
CYP1A2-substrate:  0.798
CYP2C19-inhibitor:  0.883
CYP2C19-substrate:  0.134
CYP2C9-inhibitor:  0.792
CYP2C9-substrate:  0.954
CYP2D6-inhibitor:  0.759
CYP2D6-substrate:  0.878
CYP3A4-inhibitor:  0.781
CYP3A4-substrate:  0.218

ADMET: Excretion

Clearance (CL):  16.171
Half-life (T1/2):  0.696

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.274
Drug-inuced Liver Injury (DILI):  0.934
AMES Toxicity:  0.134
Rat Oral Acute Toxicity:  0.786
Maximum Recommended Daily Dose:  0.28
Skin Sensitization:  0.626
Carcinogencity:  0.689
Eye Corrosion:  0.013
Eye Irritation:  0.926
Respiratory Toxicity:  0.905

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  Natural Product: NPC225153

Natural Product ID:  NPC225153
Common Name*:   5-O-Methylnaringenin
IUPAC Name:   (2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydrochromen-4-one
Synonyms:   5-O-Methylnaringenin
Standard InCHIKey:  CWZLMWSCLBFCBY-ZDUSSCGKSA-N
Standard InCHI:  InChI=1S/C16H14O5/c1-20-14-6-11(18)7-15-16(14)12(19)8-13(21-15)9-2-4-10(17)5-3-9/h2-7,13,17-18H,8H2,1H3/t13-/m0/s1
SMILES:  COc1cc(cc2c1C(=O)C[C@@H](c1ccc(cc1)O)O2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL255035
PubChem CID:   182315
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002585] O-methylated flavonoids
          • [CHEMONTID:0002590] 5-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 n.a. root n.a. PMID[10514313]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota roots n.a. n.a. PMID[10514313]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds Mengha, Yunnan Province, China 1991-Aug PMID[11277741]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds n.a. n.a. PMID[11325233]
NPO27986 Lonchocarpus chiricanus Species Fabaceae Eukaryota Root barks n.a. n.a. PMID[11421729]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota Seeds n.a. n.a. PMID[11430002]
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]
NPO10662 Scrippsiella trochoidea Species Peridiniaceae Eukaryota n.a. n.a. n.a. PMID[8021655]
NPO28159 Rubia akane Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[8176404]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9461664]
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]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23156 Maclura cochinchinensis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6295 Astragalus trojanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27397 Drymaria cordata Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27882 Boswellia ovalifoliolata Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2787 Cussonia racemosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11281 Euphorbia fortissima Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1373 Pulsatilla chinensis 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]
NPO28044 Erythrina hypaphorus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17337 Centaurea scoparia Species Asteraceae 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]
NPO16156 Mucuna holtonii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28313 Mentzelia decapetala Species Loasaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28003 Astragalus circassicus 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]
NPO1219 Theobroma speciosum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27637 Heliotropium scabrum Species Heliotropiaceae 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]
NPO28206 Aniba santalodora Species Lauraceae 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]
NPO11849 Cynoglossum macrostylum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28083 Salvia lavanduloides Species Lamiaceae 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]
NPO27702 Matricaria sabulosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27506 Orgyia pseudotsugata Species Lymantriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23156 Maclura cochinchinensis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1373 Pulsatilla chinensis Species Ranunculaceae 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]
NPO27854 Sphaeria rousseliana n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27695 Centaurea sonchifolia Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16092 Calocephalus knappii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27642 Podocarpus dacrydioides Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO742 Aloe saponaria Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27600 Boesenbergia pandurata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27614 Salix rosmarinifolia Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27057 Matsucoccus josephi Species Margarodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19383 Lactarius mitissimus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28159 Rubia akane Species Rubiaceae 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]
NPO6295 Astragalus trojanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11281 Euphorbia fortissima 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]
NPO28385 Iris kashmiriana Species Tarachodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28289 Nepytia freemani Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28426 Etmopterus spinax Species Etmopteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26476 Preussia terricola Species Sporormiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27882 Boswellia ovalifoliolata Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27455 Dysidea fragilis Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14345 Androsace septentrionalis Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28412 Amorphophallus konjac Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27338 Senecio platyphylloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27234 Thalassiosira weissflogii Species Thalassiosiraceae 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]
NPO2787 Cussonia racemosa Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26321 Salvia patens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27986 Lonchocarpus chiricanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10662 Scrippsiella trochoidea Species Peridiniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27816 Pterocaulon serrulatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28063 Beilschmiedia madang Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25499 Campanula choziatowskyi Species Campanulaceae 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
NPT461 Cell Line PANC-1 Homo sapiens PC100 > 256.0 uM PMID[541492]
NPT453 Cell Line HT-1080 Homo sapiens ED50 > 100.0 uM PMID[541493]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 100.0 uM PMID[541493]

☑ 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 NPC225153 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 NPC265871
1.0 High Similarity NPC20709
1.0 High Similarity NPC329203
1.0 High Similarity NPC150648
1.0 High Similarity NPC310135
1.0 High Similarity NPC222342
1.0 High Similarity NPC274784
0.9925 High Similarity NPC6407
0.9925 High Similarity NPC188243
0.9925 High Similarity NPC110228
0.9852 High Similarity NPC213322
0.9852 High Similarity NPC4743
0.9852 High Similarity NPC312391
0.9852 High Similarity NPC324386
0.9851 High Similarity NPC140890
0.985 High Similarity NPC107586
0.985 High Similarity NPC243083
0.985 High Similarity NPC287246
0.985 High Similarity NPC79943
0.985 High Similarity NPC296490
0.985 High Similarity NPC12296
0.985 High Similarity NPC13768
0.985 High Similarity NPC32441
0.985 High Similarity NPC295261
0.9779 High Similarity NPC223500
0.9779 High Similarity NPC161506
0.9779 High Similarity NPC296917
0.9779 High Similarity NPC324134
0.9779 High Similarity NPC182852
0.9779 High Similarity NPC194432
0.9779 High Similarity NPC220998
0.9779 High Similarity NPC148757
0.9779 High Similarity NPC32739
0.9779 High Similarity NPC37496
0.9779 High Similarity NPC166934
0.9779 High Similarity NPC107572
0.9779 High Similarity NPC76338
0.9779 High Similarity NPC306829
0.9779 High Similarity NPC78
0.9779 High Similarity NPC265040
0.9779 High Similarity NPC125855
0.9779 High Similarity NPC167624
0.9779 High Similarity NPC10937
0.9779 High Similarity NPC228504
0.9779 High Similarity NPC166482
0.9779 High Similarity NPC324436
0.9779 High Similarity NPC76372
0.9779 High Similarity NPC177354
0.9779 High Similarity NPC66515
0.9779 High Similarity NPC328164
0.9779 High Similarity NPC64915
0.9779 High Similarity NPC227579
0.9779 High Similarity NPC40833
0.9779 High Similarity NPC1089
0.9778 High Similarity NPC129853
0.9778 High Similarity NPC284550
0.9778 High Similarity NPC76445
0.9776 High Similarity NPC472460
0.9776 High Similarity NPC118813
0.9776 High Similarity NPC99333
0.9776 High Similarity NPC280284
0.9776 High Similarity NPC188947
0.9776 High Similarity NPC147686
0.9776 High Similarity NPC329225
0.9708 High Similarity NPC175504
0.9708 High Similarity NPC278249
0.9708 High Similarity NPC143896
0.9708 High Similarity NPC223812
0.9708 High Similarity NPC85162
0.9708 High Similarity NPC75049
0.9708 High Similarity NPC39329
0.9708 High Similarity NPC316816
0.9708 High Similarity NPC310130
0.9708 High Similarity NPC150408
0.9708 High Similarity NPC81697
0.9708 High Similarity NPC91560
0.9708 High Similarity NPC68104
0.9708 High Similarity NPC164980
0.9708 High Similarity NPC149026
0.9708 High Similarity NPC185276
0.9708 High Similarity NPC214166
0.9708 High Similarity NPC221432
0.9708 High Similarity NPC257097
0.9708 High Similarity NPC125894
0.9708 High Similarity NPC107177
0.9708 High Similarity NPC169591
0.9708 High Similarity NPC77794
0.9708 High Similarity NPC478086
0.9706 High Similarity NPC156190
0.9706 High Similarity NPC166689
0.9706 High Similarity NPC258630
0.9706 High Similarity NPC96408
0.9706 High Similarity NPC279650
0.9706 High Similarity NPC3188
0.9706 High Similarity NPC248372
0.9706 High Similarity NPC110038
0.9706 High Similarity NPC17170
0.9704 High Similarity NPC261234
0.9701 High Similarity NPC275055
0.9701 High Similarity NPC290291
0.9701 High Similarity NPC84585
0.9701 High Similarity NPC476480
0.9638 High Similarity NPC131568
0.9638 High Similarity NPC209040
0.9638 High Similarity NPC236766
0.9638 High Similarity NPC235217
0.9638 High Similarity NPC197252
0.9638 High Similarity NPC473013
0.9638 High Similarity NPC473014
0.9638 High Similarity NPC131579
0.9638 High Similarity NPC473015
0.9635 High Similarity NPC202981
0.9635 High Similarity NPC73028
0.963 High Similarity NPC124269
0.9627 High Similarity NPC124784
0.9627 High Similarity NPC29353
0.9627 High Similarity NPC234133
0.9627 High Similarity NPC473887
0.9627 High Similarity NPC47815
0.9627 High Similarity NPC231772
0.9627 High Similarity NPC127447
0.9627 High Similarity NPC194281
0.9568 High Similarity NPC83357
0.9568 High Similarity NPC109183
0.9568 High Similarity NPC214774
0.9568 High Similarity NPC301276
0.9568 High Similarity NPC470134
0.9568 High Similarity NPC142405
0.9568 High Similarity NPC176229
0.9568 High Similarity NPC20488
0.9568 High Similarity NPC470132
0.9568 High Similarity NPC312973
0.9568 High Similarity NPC88964
0.9568 High Similarity NPC267375
0.9568 High Similarity NPC246948
0.9568 High Similarity NPC285630
0.9568 High Similarity NPC470133
0.9568 High Similarity NPC475052
0.9568 High Similarity NPC127059
0.9568 High Similarity NPC470131
0.9568 High Similarity NPC473078
0.9568 High Similarity NPC111786
0.9568 High Similarity NPC67805
0.9568 High Similarity NPC470647
0.9568 High Similarity NPC195621
0.9568 High Similarity NPC472629
0.9568 High Similarity NPC54577
0.9565 High Similarity NPC113770
0.9559 High Similarity NPC316480
0.9559 High Similarity NPC18260
0.9559 High Similarity NPC78913
0.9556 High Similarity NPC250266
0.9556 High Similarity NPC266597
0.9556 High Similarity NPC188879
0.9552 High Similarity NPC239495
0.9552 High Similarity NPC9985
0.9552 High Similarity NPC99854
0.95 High Similarity NPC23728
0.95 High Similarity NPC296998
0.95 High Similarity NPC472627
0.95 High Similarity NPC110303
0.95 High Similarity NPC476182
0.95 High Similarity NPC40086
0.95 High Similarity NPC122828
0.95 High Similarity NPC300988
0.95 High Similarity NPC176869
0.95 High Similarity NPC473077
0.95 High Similarity NPC3779
0.95 High Similarity NPC211466
0.95 High Similarity NPC10990
0.95 High Similarity NPC44721
0.95 High Similarity NPC283234
0.9496 High Similarity NPC470135
0.9496 High Similarity NPC110776
0.9496 High Similarity NPC271590
0.9496 High Similarity NPC87486
0.9496 High Similarity NPC271288
0.9496 High Similarity NPC124780
0.9496 High Similarity NPC184649
0.9496 High Similarity NPC470136
0.9496 High Similarity NPC470890
0.9496 High Similarity NPC303185
0.9496 High Similarity NPC39045
0.9496 High Similarity NPC311144
0.9496 High Similarity NPC319752
0.9493 High Similarity NPC147145
0.9489 High Similarity NPC182421
0.9489 High Similarity NPC241100
0.9489 High Similarity NPC69769
0.9489 High Similarity NPC159275
0.9485 High Similarity NPC201395
0.9481 High Similarity NPC13408
0.9481 High Similarity NPC240593
0.9433 High Similarity NPC132592
0.9433 High Similarity NPC161191
0.9433 High Similarity NPC160821
0.9429 High Similarity NPC187282
0.9429 High Similarity NPC474161
0.9429 High Similarity NPC476153
0.9429 High Similarity NPC299011

  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 NPC225153 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
0.985 High Similarity NPD1550 Clinical (unspecified phase)
0.985 High Similarity NPD1552 Clinical (unspecified phase)
0.9776 High Similarity NPD1549 Phase 2
0.9265 High Similarity NPD1510 Phase 2
0.9254 High Similarity NPD1240 Approved
0.922 High Similarity NPD4378 Clinical (unspecified phase)
0.9197 High Similarity NPD2796 Approved
0.9172 High Similarity NPD1934 Approved
0.9118 High Similarity NPD1607 Approved
0.911 High Similarity NPD2393 Clinical (unspecified phase)
0.9048 High Similarity NPD8443 Clinical (unspecified phase)
0.8973 High Similarity NPD7411 Suspended
0.8951 High Similarity NPD7410 Clinical (unspecified phase)
0.8926 High Similarity NPD7075 Discontinued
0.8904 High Similarity NPD4380 Phase 2
0.8851 High Similarity NPD7096 Clinical (unspecified phase)
0.88 High Similarity NPD4381 Clinical (unspecified phase)
0.875 High Similarity NPD1511 Approved
0.875 High Similarity NPD6799 Approved
0.8725 High Similarity NPD7819 Suspended
0.8658 High Similarity NPD6801 Discontinued
0.863 High Similarity NPD1512 Approved
0.86 High Similarity NPD2801 Approved
0.8581 High Similarity NPD6167 Clinical (unspecified phase)
0.8581 High Similarity NPD6166 Phase 2
0.8581 High Similarity NPD6168 Clinical (unspecified phase)
0.8551 High Similarity NPD6859 Clinical (unspecified phase)
0.8542 High Similarity NPD3750 Approved
0.8523 High Similarity NPD6599 Discontinued
0.8521 High Similarity NPD1551 Phase 2
0.8506 High Similarity NPD6959 Discontinued
0.8487 Intermediate Similarity NPD3882 Suspended
0.8472 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8462 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8433 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.8431 Intermediate Similarity NPD3749 Approved
0.8418 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8403 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8366 Intermediate Similarity NPD7768 Phase 2
0.8365 Intermediate Similarity NPD7074 Phase 3
0.8345 Intermediate Similarity NPD2800 Approved
0.8322 Intermediate Similarity NPD5403 Approved
0.8311 Intermediate Similarity NPD5401 Approved
0.8302 Intermediate Similarity NPD7054 Approved
0.8301 Intermediate Similarity NPD3817 Phase 2
0.825 Intermediate Similarity NPD7472 Approved
0.8247 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD3818 Discontinued
0.8207 Intermediate Similarity NPD2344 Approved
0.8205 Intermediate Similarity NPD5494 Approved
0.8199 Intermediate Similarity NPD6797 Phase 2
0.8194 Intermediate Similarity NPD3748 Approved
0.8188 Intermediate Similarity NPD1203 Approved
0.8182 Intermediate Similarity NPD6651 Approved
0.8163 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8162 Intermediate Similarity NPD1610 Phase 2
0.8148 Intermediate Similarity NPD7251 Discontinued
0.8143 Intermediate Similarity NPD4908 Phase 1
0.8134 Intermediate Similarity NPD1548 Phase 1
0.8098 Intermediate Similarity NPD7808 Phase 3
0.8095 Intermediate Similarity NPD1243 Approved
0.8079 Intermediate Similarity NPD920 Approved
0.8069 Intermediate Similarity NPD7033 Discontinued
0.8054 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8041 Intermediate Similarity NPD4628 Phase 3
0.8037 Intermediate Similarity NPD6559 Discontinued
0.8028 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8014 Intermediate Similarity NPD6099 Approved
0.8014 Intermediate Similarity NPD6100 Approved
0.8014 Intermediate Similarity NPD2935 Discontinued
0.8014 Intermediate Similarity NPD6832 Phase 2
0.7988 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD2309 Approved
0.7975 Intermediate Similarity NPD5953 Discontinued
0.7971 Intermediate Similarity NPD9717 Approved
0.7963 Intermediate Similarity NPD7286 Phase 2
0.7949 Intermediate Similarity NPD5402 Approved
0.7947 Intermediate Similarity NPD2534 Approved
0.7947 Intermediate Similarity NPD2532 Approved
0.7947 Intermediate Similarity NPD2533 Approved
0.7947 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7945 Intermediate Similarity NPD2799 Discontinued
0.7917 Intermediate Similarity NPD943 Approved
0.7902 Intermediate Similarity NPD3268 Approved
0.7902 Intermediate Similarity NPD2313 Discontinued
0.7899 Intermediate Similarity NPD422 Phase 1
0.7875 Intermediate Similarity NPD6232 Discontinued
0.7853 Intermediate Similarity NPD5844 Phase 1
0.784 Intermediate Similarity NPD7473 Discontinued
0.7823 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7801 Intermediate Similarity NPD2797 Approved
0.7793 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7793 Intermediate Similarity NPD1613 Approved
0.7758 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD2798 Approved
0.7742 Intermediate Similarity NPD3226 Approved
0.774 Intermediate Similarity NPD1933 Approved
0.774 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD5124 Phase 1
0.7737 Intermediate Similarity NPD9545 Approved
0.7733 Intermediate Similarity NPD4363 Phase 3
0.7733 Intermediate Similarity NPD4360 Phase 2
0.7733 Intermediate Similarity NPD2654 Approved
0.773 Intermediate Similarity NPD3225 Approved
0.7718 Intermediate Similarity NPD2346 Discontinued
0.7712 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7703 Intermediate Similarity NPD4308 Phase 3
0.7688 Intermediate Similarity NPD919 Approved
0.7682 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD3266 Approved
0.7676 Intermediate Similarity NPD3267 Approved
0.7658 Intermediate Similarity NPD1465 Phase 2
0.7655 Intermediate Similarity NPD6798 Discontinued
0.7639 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD1241 Discontinued
0.7619 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD3926 Phase 2
0.7593 Intermediate Similarity NPD1247 Approved
0.7591 Intermediate Similarity NPD9493 Approved
0.7589 Intermediate Similarity NPD1608 Approved
0.7589 Intermediate Similarity NPD3972 Approved
0.7569 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD1296 Phase 2
0.7532 Intermediate Similarity NPD7390 Discontinued
0.75 Intermediate Similarity NPD6104 Discontinued
0.75 Intermediate Similarity NPD1019 Discontinued
0.75 Intermediate Similarity NPD4288 Approved
0.75 Intermediate Similarity NPD230 Phase 1
0.75 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD4361 Phase 2
0.7485 Intermediate Similarity NPD1729 Discontinued
0.747 Intermediate Similarity NPD3751 Discontinued
0.7466 Intermediate Similarity NPD4625 Phase 3
0.7448 Intermediate Similarity NPD2861 Phase 2
0.7439 Intermediate Similarity NPD5710 Approved
0.7439 Intermediate Similarity NPD5711 Approved
0.7432 Intermediate Similarity NPD4307 Phase 2
0.7419 Intermediate Similarity NPD7212 Phase 2
0.7419 Intermediate Similarity NPD7213 Phase 3
0.7415 Intermediate Similarity NPD411 Approved
0.7415 Intermediate Similarity NPD3764 Approved
0.7413 Intermediate Similarity NPD4749 Approved
0.7405 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7399 Intermediate Similarity NPD4287 Approved
0.7394 Intermediate Similarity NPD1201 Approved
0.7391 Intermediate Similarity NPD2296 Approved
0.7386 Intermediate Similarity NPD1652 Phase 2
0.7383 Intermediate Similarity NPD447 Suspended
0.7383 Intermediate Similarity NPD6355 Discontinued
0.7376 Intermediate Similarity NPD17 Approved
0.7375 Intermediate Similarity NPD6844 Discontinued
0.7372 Intermediate Similarity NPD4662 Approved
0.7372 Intermediate Similarity NPD4661 Approved
0.7365 Intermediate Similarity NPD6233 Phase 2
0.7357 Intermediate Similarity NPD1894 Discontinued
0.7349 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD3027 Phase 3
0.7343 Intermediate Similarity NPD1481 Phase 2
0.7333 Intermediate Similarity NPD3787 Discontinued
0.7318 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD3142 Approved
0.7315 Intermediate Similarity NPD3140 Approved
0.7314 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD5889 Approved
0.7312 Intermediate Similarity NPD5890 Approved
0.731 Intermediate Similarity NPD1470 Approved
0.7308 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD7458 Discontinued
0.729 Intermediate Similarity NPD3887 Approved
0.729 Intermediate Similarity NPD2354 Approved
0.7273 Intermediate Similarity NPD7199 Phase 2
0.7273 Intermediate Similarity NPD1535 Discovery
0.7268 Intermediate Similarity NPD7584 Approved
0.7267 Intermediate Similarity NPD7577 Discontinued
0.7261 Intermediate Similarity NPD7447 Phase 1
0.7255 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD1471 Phase 3
0.7241 Intermediate Similarity NPD1876 Approved
0.7237 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD7229 Phase 3
0.7209 Intermediate Similarity NPD8313 Approved
0.7209 Intermediate Similarity NPD8312 Approved
0.7208 Intermediate Similarity NPD2424 Discontinued
0.7192 Intermediate Similarity NPD1164 Approved
0.7186 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6280 Approved
0.716 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6279 Approved
0.7143 Intermediate Similarity NPD2403 Approved
0.7143 Intermediate Similarity NPD2353 Approved
0.7143 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6585 Discontinued
0.7134 Intermediate Similarity NPD7440 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