Structure

Physi-Chem Properties

Molecular Weight:  286.08
Volume:  291.039
LogP:  2.721
LogD:  2.856
LogS:  -2.936
# Rotatable Bonds:  4
TPSA:  86.99
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.594
Synthetic Accessibility Score:  2.24
Fsp3:  0.062
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.842
MDCK Permeability:  1.282538414670853e-05
Pgp-inhibitor:  0.01
Pgp-substrate:  0.087
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.016
30% Bioavailability (F30%):  0.609

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.049
Plasma Protein Binding (PPB):  98.49860382080078%
Volume Distribution (VD):  0.548
Pgp-substrate:  1.2452629804611206%

ADMET: Metabolism

CYP1A2-inhibitor:  0.974
CYP1A2-substrate:  0.654
CYP2C19-inhibitor:  0.435
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.644
CYP2C9-substrate:  0.946
CYP2D6-inhibitor:  0.643
CYP2D6-substrate:  0.87
CYP3A4-inhibitor:  0.907
CYP3A4-substrate:  0.175

ADMET: Excretion

Clearance (CL):  14.157
Half-life (T1/2):  0.913

ADMET: Toxicity

hERG Blockers:  0.08
Human Hepatotoxicity (H-HT):  0.172
Drug-inuced Liver Injury (DILI):  0.85
AMES Toxicity:  0.786
Rat Oral Acute Toxicity:  0.771
Maximum Recommended Daily Dose:  0.819
Skin Sensitization:  0.945
Carcinogencity:  0.574
Eye Corrosion:  0.012
Eye Irritation:  0.964
Respiratory Toxicity:  0.609

Download Data

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

  Natural Product: NPC129132

Natural Product ID:  NPC129132
Common Name*:   Helichrysetin
IUPAC Name:   (E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:   Helichrysetin; Helichysetin
Standard InCHIKey:  OWGUBYRKZATRIT-QPJJXVBHSA-N
Standard InCHI:  InChI=1S/C16H14O5/c1-21-15-9-12(18)8-14(20)16(15)13(19)7-4-10-2-5-11(17)6-3-10/h2-9,17-18,20H,1H3/b7-4+
SMILES:  COc1cc(cc(c1C(=O)/C=C/c1ccc(cc1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL507998
PubChem CID:   6253344
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003467] Linear 1,3-diarylpropanoids
        • [CHEMONTID:0001630] Chalcones and dihydrochalcones
          • [CHEMONTID:0003472] 2'-Hydroxychalcones

*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]
NPO30669 Gnaphalium affine Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[10820110]
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]
NPO40881 Melodorum siamensis Species n.a. n.a. Fruit; Leaf n.a. n.a. PMID[30694059]
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]
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]
NPO30669 Gnaphalium affine Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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[TCMID]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae 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]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28159 Rubia akane Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1373 Pulsatilla chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27642 Podocarpus dacrydioides Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28426 Etmopterus spinax Species Etmopteridae 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]
NPO27057 Matsucoccus josephi Species Margarodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28412 Amorphophallus konjac Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27600 Boesenbergia pandurata Species Zingiberaceae 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]
NPO2030 Mimosa pigra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28159 Rubia akane Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae 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]
NPO25499 Campanula choziatowskyi Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27916 Hardenbergia violacea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27455 Dysidea fragilis Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4407 Dryopteris fragrans Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26476 Preussia terricola Species Sporormiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27234 Thalassiosira weissflogii Species Thalassiosiraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28044 Erythrina hypaphorus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27882 Boswellia ovalifoliolata Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26553 Lemonia spectabilis Species Lemoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26321 Salvia patens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23315 Epaltes brasiliensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27986 Lonchocarpus chiricanus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16156 Mucuna holtonii 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]
NPO28063 Beilschmiedia madang 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]
NPO4188 Python molurus Species Pythonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27613 Helleborus macranthus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11849 Cynoglossum macrostylum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27816 Pterocaulon serrulatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28003 Astragalus circassicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26342 Dialium excelsum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27637 Heliotropium scabrum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23990 Quivisianthe papinae Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17337 Centaurea scoparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16298 Quercus marilandica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8961 Bethencourtia palmensis 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]
NPO28313 Mentzelia decapetala Species Loasaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13330 Rubus sieboldii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27397 Drymaria cordata Species Caryophyllaceae 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]
NPO27702 Matricaria sabulosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27614 Salix rosmarinifolia Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28083 Salvia lavanduloides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23156 Maclura cochinchinensis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19745 Esox lucius Species Esocidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24965 Goldfussia psilostachys n.a. n.a. n.a. 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]
NPO19383 Lactarius mitissimus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1373 Pulsatilla chinensis Species Ranunculaceae 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]

☑ 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
NPT453 Cell Line HT-1080 Homo sapiens ED50 = 40.1 uM PMID[520148]
NPT165 Cell Line HeLa Homo sapiens IC50 = 5200.0 nM PMID[520149]
NPT165 Cell Line HeLa Homo sapiens IC50 = 48100.0 nM PMID[520153]
NPT81 Cell Line A549 Homo sapiens IC50 > 50000.0 nM PMID[520153]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 40200.0 nM PMID[520153]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 64.7 uM PMID[520148]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 4.4 n.a. PMID[520149]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 32.3 % PMID[520150]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 48.9 % PMID[520150]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 100.0 % PMID[520150]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 63.8 % PMID[520150]
NPT2 Others Unspecified Ratio IC50 = 1.4 n.a. PMID[520151]
NPT27 Others Unspecified IC50 = 21700.0 nM PMID[520151]
NPT634 Organism Leishmania amazonensis Leishmania amazonensis IC50 = 15700.0 nM PMID[520151]
NPT1175 Organism Spodoptera litura Spodoptera litura pED50 = 6.42 n.a. PMID[520152]
NPT1175 Organism Spodoptera litura Spodoptera litura ED50 = 3.8 10'-7mol/cm2 PMID[520152]

☑ 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 NPC129132 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 NPC87231
1.0 High Similarity NPC205468
1.0 High Similarity NPC257756
1.0 High Similarity NPC212631
0.9921 High Similarity NPC312318
0.9921 High Similarity NPC472365
0.9921 High Similarity NPC263670
0.9921 High Similarity NPC188646
0.9921 High Similarity NPC242294
0.9921 High Similarity NPC175098
0.9921 High Similarity NPC262359
0.9921 High Similarity NPC192304
0.9921 High Similarity NPC337373
0.9921 High Similarity NPC56031
0.9921 High Similarity NPC308037
0.9921 High Similarity NPC139813
0.9921 High Similarity NPC64359
0.9844 High Similarity NPC286336
0.9766 High Similarity NPC20560
0.9766 High Similarity NPC82225
0.9766 High Similarity NPC159623
0.9766 High Similarity NPC18877
0.9766 High Similarity NPC28753
0.9766 High Similarity NPC204960
0.9766 High Similarity NPC144051
0.9766 High Similarity NPC294593
0.9764 High Similarity NPC313618
0.9762 High Similarity NPC247779
0.9692 High Similarity NPC186838
0.9692 High Similarity NPC473391
0.9692 High Similarity NPC477244
0.9692 High Similarity NPC249606
0.9692 High Similarity NPC1486
0.9692 High Similarity NPC12165
0.9692 High Similarity NPC66349
0.9692 High Similarity NPC41461
0.9692 High Similarity NPC25287
0.9692 High Similarity NPC274109
0.9692 High Similarity NPC168105
0.9692 High Similarity NPC472364
0.9692 High Similarity NPC477242
0.9692 High Similarity NPC150399
0.9692 High Similarity NPC476333
0.9692 High Similarity NPC98115
0.9692 High Similarity NPC477243
0.9692 High Similarity NPC472367
0.9618 High Similarity NPC250266
0.9618 High Similarity NPC209560
0.9618 High Similarity NPC153979
0.9618 High Similarity NPC181124
0.9618 High Similarity NPC162680
0.9618 High Similarity NPC294409
0.9618 High Similarity NPC303644
0.9618 High Similarity NPC7013
0.9618 High Similarity NPC116632
0.9618 High Similarity NPC188879
0.9618 High Similarity NPC317119
0.9618 High Similarity NPC472419
0.9618 High Similarity NPC266597
0.9615 High Similarity NPC13575
0.9615 High Similarity NPC131039
0.9615 High Similarity NPC156092
0.9609 High Similarity NPC128348
0.9609 High Similarity NPC475008
0.9609 High Similarity NPC66384
0.9609 High Similarity NPC309717
0.9609 High Similarity NPC186097
0.9609 High Similarity NPC475009
0.9609 High Similarity NPC112192
0.9609 High Similarity NPC164236
0.9609 High Similarity NPC189106
0.9603 High Similarity NPC80694
0.9603 High Similarity NPC186098
0.9545 High Similarity NPC279668
0.9545 High Similarity NPC188947
0.9545 High Similarity NPC309154
0.9545 High Similarity NPC99333
0.9545 High Similarity NPC55162
0.9545 High Similarity NPC278323
0.9545 High Similarity NPC280284
0.9545 High Similarity NPC472368
0.9545 High Similarity NPC12175
0.9545 High Similarity NPC21350
0.9545 High Similarity NPC124269
0.9545 High Similarity NPC90665
0.9542 High Similarity NPC240593
0.9542 High Similarity NPC47815
0.9542 High Similarity NPC213603
0.9542 High Similarity NPC231772
0.9542 High Similarity NPC234133
0.9542 High Similarity NPC473887
0.9542 High Similarity NPC127447
0.9542 High Similarity NPC194281
0.9542 High Similarity NPC29353
0.9542 High Similarity NPC124784
0.9538 High Similarity NPC103842
0.9528 High Similarity NPC211120
0.9524 High Similarity NPC128428
0.9524 High Similarity NPC305518
0.9474 High Similarity NPC295384
0.9474 High Similarity NPC477956
0.9474 High Similarity NPC470211
0.9474 High Similarity NPC472366
0.947 High Similarity NPC290291
0.947 High Similarity NPC275055
0.9466 High Similarity NPC234560
0.9466 High Similarity NPC39426
0.9462 High Similarity NPC27643
0.9453 High Similarity NPC185497
0.9403 High Similarity NPC281207
0.9403 High Similarity NPC269652
0.9403 High Similarity NPC259166
0.9403 High Similarity NPC48624
0.9403 High Similarity NPC101366
0.9403 High Similarity NPC11056
0.9403 High Similarity NPC219917
0.9403 High Similarity NPC204985
0.9403 High Similarity NPC172250
0.9403 High Similarity NPC144118
0.9403 High Similarity NPC80962
0.9403 High Similarity NPC326109
0.9403 High Similarity NPC215311
0.9403 High Similarity NPC213659
0.9398 High Similarity NPC251681
0.9398 High Similarity NPC471620
0.9398 High Similarity NPC243528
0.9394 High Similarity NPC13408
0.9394 High Similarity NPC235428
0.9394 High Similarity NPC87545
0.9389 High Similarity NPC172262
0.9375 High Similarity NPC60558
0.9375 High Similarity NPC212379
0.9375 High Similarity NPC69235
0.9333 High Similarity NPC3188
0.9333 High Similarity NPC26051
0.9333 High Similarity NPC49108
0.9333 High Similarity NPC470087
0.9333 High Similarity NPC136840
0.9333 High Similarity NPC110969
0.9333 High Similarity NPC268204
0.9333 High Similarity NPC470089
0.9333 High Similarity NPC321980
0.9333 High Similarity NPC301178
0.9333 High Similarity NPC52789
0.9333 High Similarity NPC284556
0.9333 High Similarity NPC469404
0.9333 High Similarity NPC55832
0.9328 High Similarity NPC261234
0.9328 High Similarity NPC283429
0.9328 High Similarity NPC265871
0.9328 High Similarity NPC241838
0.9328 High Similarity NPC150648
0.9328 High Similarity NPC78913
0.9328 High Similarity NPC222342
0.9328 High Similarity NPC225153
0.9328 High Similarity NPC152042
0.9328 High Similarity NPC143799
0.9328 High Similarity NPC310135
0.9328 High Similarity NPC274784
0.9328 High Similarity NPC109232
0.9328 High Similarity NPC329203
0.9328 High Similarity NPC20709
0.9328 High Similarity NPC18260
0.9323 High Similarity NPC212767
0.9323 High Similarity NPC228661
0.9318 High Similarity NPC9985
0.9318 High Similarity NPC239495
0.9313 High Similarity NPC78540
0.9313 High Similarity NPC57601
0.9313 High Similarity NPC50898
0.9313 High Similarity NPC213216
0.9313 High Similarity NPC274121
0.9308 High Similarity NPC475589
0.9308 High Similarity NPC31872
0.9308 High Similarity NPC473584
0.9302 High Similarity NPC42292
0.9302 High Similarity NPC307732
0.9265 High Similarity NPC226636
0.9265 High Similarity NPC119663
0.9265 High Similarity NPC11561
0.9265 High Similarity NPC471417
0.9265 High Similarity NPC202981
0.9259 High Similarity NPC253822
0.9259 High Similarity NPC184536
0.9259 High Similarity NPC129853
0.9259 High Similarity NPC188243
0.9259 High Similarity NPC103342
0.9259 High Similarity NPC103904
0.9259 High Similarity NPC69769
0.9259 High Similarity NPC110228
0.9259 High Similarity NPC241100
0.9259 High Similarity NPC284550
0.9259 High Similarity NPC230285
0.9259 High Similarity NPC159275
0.9259 High Similarity NPC76445
0.9259 High Similarity NPC59951
0.9259 High Similarity NPC6407
0.9259 High Similarity NPC270883
0.9259 High Similarity NPC265178
0.9259 High Similarity NPC172986

  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 NPC129132 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
0.9764 High Similarity NPD1240 Approved
0.9612 High Similarity NPD1607 Approved
0.9466 High Similarity NPD1510 Phase 2
0.9254 High Similarity NPD1549 Phase 2
0.9179 High Similarity NPD1550 Clinical (unspecified phase)
0.9179 High Similarity NPD1552 Clinical (unspecified phase)
0.8993 High Similarity NPD4378 Clinical (unspecified phase)
0.8857 High Similarity NPD7410 Clinical (unspecified phase)
0.8824 High Similarity NPD2796 Approved
0.8786 High Similarity NPD6799 Approved
0.8696 High Similarity NPD970 Clinical (unspecified phase)
0.8681 High Similarity NPD4380 Phase 2
0.8652 High Similarity NPD1511 Approved
0.8621 High Similarity NPD7411 Suspended
0.8571 High Similarity NPD1878 Clinical (unspecified phase)
0.8562 High Similarity NPD1934 Approved
0.8551 High Similarity NPD1551 Phase 2
0.8531 High Similarity NPD1512 Approved
0.8514 High Similarity NPD3882 Suspended
0.8503 High Similarity NPD2393 Clinical (unspecified phase)
0.8503 High Similarity NPD2801 Approved
0.8467 Intermediate Similarity NPD6651 Approved
0.8456 Intermediate Similarity NPD7075 Discontinued
0.8446 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8444 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.844 Intermediate Similarity NPD3750 Approved
0.8425 Intermediate Similarity NPD6599 Discontinued
0.8417 Intermediate Similarity NPD2935 Discontinued
0.8378 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8378 Intermediate Similarity NPD7819 Suspended
0.8346 Intermediate Similarity NPD1203 Approved
0.8333 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8321 Intermediate Similarity NPD943 Approved
0.8311 Intermediate Similarity NPD6801 Discontinued
0.8239 Intermediate Similarity NPD2800 Approved
0.8239 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8227 Intermediate Similarity NPD2344 Approved
0.8212 Intermediate Similarity NPD3749 Approved
0.8146 Intermediate Similarity NPD7768 Phase 2
0.814 Intermediate Similarity NPD9493 Approved
0.8129 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.812 Intermediate Similarity NPD9717 Approved
0.8112 Intermediate Similarity NPD1243 Approved
0.8112 Intermediate Similarity NPD2654 Approved
0.8095 Intermediate Similarity NPD5403 Approved
0.8085 Intermediate Similarity NPD3748 Approved
0.8085 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8082 Intermediate Similarity NPD5401 Approved
0.8079 Intermediate Similarity NPD3817 Phase 2
0.8029 Intermediate Similarity NPD6832 Phase 2
0.8015 Intermediate Similarity NPD9545 Approved
0.8015 Intermediate Similarity NPD2798 Approved
0.8013 Intermediate Similarity NPD6166 Phase 2
0.8013 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD6232 Discontinued
0.8 Intermediate Similarity NPD2309 Approved
0.7985 Intermediate Similarity NPD3972 Approved
0.7973 Intermediate Similarity NPD920 Approved
0.7962 Intermediate Similarity NPD7473 Discontinued
0.7959 Intermediate Similarity NPD2532 Approved
0.7959 Intermediate Similarity NPD2533 Approved
0.7959 Intermediate Similarity NPD2534 Approved
0.7958 Intermediate Similarity NPD2799 Discontinued
0.7945 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD6959 Discontinued
0.7911 Intermediate Similarity NPD3818 Discontinued
0.791 Intermediate Similarity NPD422 Phase 1
0.791 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD1548 Phase 1
0.7875 Intermediate Similarity NPD5953 Discontinued
0.7862 Intermediate Similarity NPD7286 Phase 2
0.7862 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD7054 Approved
0.7838 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD7472 Approved
0.7812 Intermediate Similarity NPD7074 Phase 3
0.7808 Intermediate Similarity NPD4628 Phase 3
0.7792 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD2313 Discontinued
0.7764 Intermediate Similarity NPD6797 Phase 2
0.7756 Intermediate Similarity NPD5494 Approved
0.7746 Intermediate Similarity NPD230 Phase 1
0.7733 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD5402 Approved
0.7716 Intermediate Similarity NPD7251 Discontinued
0.7708 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD7808 Phase 3
0.766 Intermediate Similarity NPD3268 Approved
0.7655 Intermediate Similarity NPD6099 Approved
0.7655 Intermediate Similarity NPD6100 Approved
0.7651 Intermediate Similarity NPD7390 Discontinued
0.7647 Intermediate Similarity NPD1610 Phase 2
0.7643 Intermediate Similarity NPD4908 Phase 1
0.7634 Intermediate Similarity NPD1241 Discontinued
0.7632 Intermediate Similarity NPD3226 Approved
0.7622 Intermediate Similarity NPD1933 Approved
0.7622 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD3926 Phase 2
0.7609 Intermediate Similarity NPD3225 Approved
0.7609 Intermediate Similarity NPD1876 Approved
0.7607 Intermediate Similarity NPD6559 Discontinued
0.7586 Intermediate Similarity NPD4308 Phase 3
0.7586 Intermediate Similarity NPD7033 Discontinued
0.758 Intermediate Similarity NPD919 Approved
0.7561 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD1164 Approved
0.7554 Intermediate Similarity NPD1470 Approved
0.7554 Intermediate Similarity NPD2797 Approved
0.7535 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7535 Intermediate Similarity NPD3764 Approved
0.7535 Intermediate Similarity NPD411 Approved
0.7519 Intermediate Similarity NPD74 Approved
0.7519 Intermediate Similarity NPD9266 Approved
0.7518 Intermediate Similarity NPD1201 Approved
0.75 Intermediate Similarity NPD1019 Discontinued
0.75 Intermediate Similarity NPD447 Suspended
0.7484 Intermediate Similarity NPD1247 Approved
0.7483 Intermediate Similarity NPD2346 Discontinued
0.7464 Intermediate Similarity NPD1608 Approved
0.745 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD9494 Approved
0.7442 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD9263 Approved
0.7442 Intermediate Similarity NPD9267 Approved
0.7442 Intermediate Similarity NPD9264 Approved
0.7436 Intermediate Similarity NPD1465 Phase 2
0.7429 Intermediate Similarity NPD3266 Approved
0.7429 Intermediate Similarity NPD3267 Approved
0.7423 Intermediate Similarity NPD5844 Phase 1
0.7413 Intermediate Similarity NPD1296 Phase 2
0.741 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD7458 Discontinued
0.7389 Intermediate Similarity NPD4288 Approved
0.7389 Intermediate Similarity NPD2296 Approved
0.7378 Intermediate Similarity NPD1729 Discontinued
0.7343 Intermediate Similarity NPD3027 Phase 3
0.7338 Intermediate Similarity NPD1481 Phase 2
0.7333 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7003 Approved
0.7329 Intermediate Similarity NPD5711 Approved
0.7329 Intermediate Similarity NPD5710 Approved
0.731 Intermediate Similarity NPD4307 Phase 2
0.7303 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD5406 Approved
0.7297 Intermediate Similarity NPD5408 Approved
0.7297 Intermediate Similarity NPD5404 Approved
0.7297 Intermediate Similarity NPD5405 Approved
0.7289 Intermediate Similarity NPD6104 Discontinued
0.7285 Intermediate Similarity NPD2354 Approved
0.7273 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD1535 Discovery
0.7248 Intermediate Similarity NPD1471 Phase 3
0.7246 Intermediate Similarity NPD17 Approved
0.7241 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD1894 Discontinued
0.7225 Intermediate Similarity NPD4363 Phase 3
0.7225 Intermediate Similarity NPD4360 Phase 2
0.7214 Intermediate Similarity NPD9269 Phase 2
0.7203 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD3847 Discontinued
0.7193 Intermediate Similarity NPD4287 Approved
0.7192 Intermediate Similarity NPD1613 Approved
0.7192 Intermediate Similarity NPD3142 Approved
0.7192 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD3140 Approved
0.7188 Intermediate Similarity NPD846 Approved
0.7188 Intermediate Similarity NPD940 Approved
0.7185 Intermediate Similarity NPD9281 Approved
0.7184 Intermediate Similarity NPD4361 Phase 2
0.7184 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD9268 Approved
0.7172 Intermediate Similarity NPD6798 Discontinued
0.7153 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD5536 Phase 2
0.7152 Intermediate Similarity NPD3751 Discontinued
0.7143 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4661 Approved
0.7143 Intermediate Similarity NPD5124 Phase 1
0.7143 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4662 Approved
0.7134 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD2353 Approved
0.7132 Intermediate Similarity NPD9261 Approved
0.7113 Intermediate Similarity NPD1283 Approved
0.711 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD4625 Phase 3
0.7083 Intermediate Similarity NPD3018 Phase 2
0.7081 Intermediate Similarity NPD6971 Discontinued
0.7078 Intermediate Similarity NPD4357 Discontinued
0.7059 Intermediate Similarity NPD3887 Approved
0.705 Intermediate Similarity NPD1651 Approved
0.7044 Intermediate Similarity NPD6279 Approved
0.7044 Intermediate Similarity NPD6280 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