Structure

Physi-Chem Properties

Molecular Weight:  240.08
Volume:  256.162
LogP:  2.753
LogD:  2.742
LogS:  -3.132
# Rotatable Bonds:  3
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.64
Synthetic Accessibility Score:  1.814
Fsp3:  0.0
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:  -4.653
MDCK Permeability:  1.3201799447415397e-05
Pgp-inhibitor:  0.014
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.147
Plasma Protein Binding (PPB):  98.90201568603516%
Volume Distribution (VD):  0.601
Pgp-substrate:  1.0754145383834839%

ADMET: Metabolism

CYP1A2-inhibitor:  0.954
CYP1A2-substrate:  0.092
CYP2C19-inhibitor:  0.852
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.607
CYP2C9-substrate:  0.95
CYP2D6-inhibitor:  0.413
CYP2D6-substrate:  0.869
CYP3A4-inhibitor:  0.796
CYP3A4-substrate:  0.271

ADMET: Excretion

Clearance (CL):  12.872
Half-life (T1/2):  0.912

ADMET: Toxicity

hERG Blockers:  0.048
Human Hepatotoxicity (H-HT):  0.237
Drug-inuced Liver Injury (DILI):  0.431
AMES Toxicity:  0.676
Rat Oral Acute Toxicity:  0.862
Maximum Recommended Daily Dose:  0.167
Skin Sensitization:  0.943
Carcinogencity:  0.7
Eye Corrosion:  0.045
Eye Irritation:  0.982
Respiratory Toxicity:  0.471

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC17525

Natural Product ID:  NPC17525
Common Name*:   4,4'-Dihydroxychalcone
IUPAC Name:   (E)-1,3-bis(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:   4',4-Dihydroxychalcone; 4,4'-Dihydroxychalcone
Standard InCHIKey:  FZQLEXXZAVVCCA-XCVCLJGOSA-N
Standard InCHI:  InChI=1S/C15H12O3/c16-13-6-1-11(2-7-13)3-10-15(18)12-4-8-14(17)9-5-12/h1-10,16-17H/b10-3+
SMILES:  Oc1ccc(cc1)/C=C/C(=O)c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL145927
PubChem CID:   5467477
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003467] Linear 1,3-diarylpropanoids
        • [CHEMONTID:0001630] Chalcones and dihydrochalcones
          • [CHEMONTID:0003474] Retrochalcones

*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
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]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota Seeds n.a. n.a. PMID[11430002]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26690274]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9461664]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25653 Spatholobus suberectus 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]

☑ 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 > 100.0 uM PMID[459566]
NPT43 Individual Protein Tyrosinase Agaricus bisporus IC50 = 4800.0 nM PMID[459567]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Ki = 2900.0 nM PMID[459567]
NPT319 Cell Line B16 Mus musculus IC50 = 48700.0 nM PMID[459567]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 31188.9 nM PMID[459568]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 27352.69 nM PMID[459568]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 25527.01 nM PMID[459568]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 23933.16 nM PMID[459568]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 31550.05 nM PMID[459568]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 22029.26 nM PMID[459568]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 17021.59 nM PMID[459568]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 34197.94 nM PMID[459568]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 21086.28 nM PMID[459568]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 21527.82 nM PMID[459568]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 27669.42 nM PMID[459568]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 31045.6 nM PMID[459568]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 27227.01 nM PMID[459568]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 22029.26 nM PMID[459568]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 19319.68 nM PMID[459568]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 21627.19 nM PMID[459568]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 21777.1 nM PMID[459568]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 17988.71 nM PMID[459568]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 16672.47 nM PMID[459568]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 33342.64 nM PMID[459568]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 16519.62 nM PMID[459568]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 43651.58 nM PMID[459568]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 32658.78 nM PMID[459568]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 46881.34 nM PMID[459568]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 9705.1 nM PMID[459568]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 26061.54 nM PMID[459568]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 21727.01 nM PMID[459568]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 11912.42 nM PMID[459568]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 3944.57 nM PMID[459568]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 19275.25 nM PMID[459568]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 18836.49 nM PMID[459568]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 30199.52 nM PMID[459568]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 11168.63 nM PMID[459568]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 69823.24 nM PMID[459568]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 11350.11 nM PMID[459568]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 32583.67 nM PMID[459568]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 19633.6 nM PMID[459568]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 20276.83 nM PMID[459568]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 30549.21 nM PMID[459568]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 24043.63 nM PMID[459568]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 20941.12 nM PMID[459568]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 20276.83 nM PMID[459568]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 16788.04 nM PMID[459568]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 21428.91 nM PMID[459568]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 42266.86 nM PMID[459568]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 32885.16 nM PMID[459568]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 28707.81 nM PMID[459568]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 42559.84 nM PMID[459568]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 18879.91 nM PMID[459568]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 26791.68 nM PMID[459568]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 44055.49 nM PMID[459568]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 18071.74 nM PMID[459568]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 25468.3 nM PMID[459568]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 40179.08 nM PMID[459568]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 32136.61 nM PMID[459568]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 31841.98 nM PMID[459568]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 26977.39 nM PMID[459568]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 23173.95 nM PMID[459568]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 45185.59 nM PMID[459568]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 29512.09 nM PMID[459568]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 18030.18 nM PMID[459568]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 13645.83 nM PMID[459568]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 16788.04 nM PMID[459568]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 19906.73 nM PMID[459568]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 28054.34 nM PMID[459568]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 22908.68 nM PMID[459568]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 30408.85 nM PMID[459568]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 35156.04 nM PMID[459568]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000.0 nM PMID[459572]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 10000.0 nM PMID[459572]
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 117000.0 nM PMID[459573]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 83000.0 nM PMID[459563]
NPT27 Others Unspecified IC50 = 59000.0 nM PMID[459563]
NPT2 Others Unspecified IC50 > 50000.0 nM PMID[459565]
NPT2 Others Unspecified Inhibition = 28.2 % PMID[459565]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 100.0 uM PMID[459566]
NPT32 Organism Mus musculus Mus musculus Inhibition = 5.42 % PMID[459569]
NPT677 Individual Protein Coagulation factor III Homo sapiens IC50 = 0.96 nM PMID[459570]
NPT610 Others Molecular identity unknown Inhibition = 89.6 % PMID[459571]
NPT610 Others Molecular identity unknown Inhibition = 68.3 % PMID[459571]
NPT610 Others Molecular identity unknown Inhibition = 92.7 % PMID[459571]
NPT610 Others Molecular identity unknown Inhibition = 70.9 % PMID[459571]
NPT35 Others n.a. Activity = 0.43 mmolequiv/mmol PMID[459573]
NPT35 Others n.a. Inhibition = 35.9 % PMID[459573]

☑ 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 NPC17525 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9804 High Similarity NPC116842
0.9709 High Similarity NPC268388
0.9604 High Similarity NPC6984
0.951 High Similarity NPC226699
0.9346 High Similarity NPC322197
0.9327 High Similarity NPC95172
0.932 High Similarity NPC141523
0.9223 High Similarity NPC95178
0.9223 High Similarity NPC29989
0.9223 High Similarity NPC69332
0.9151 High Similarity NPC212718
0.9151 High Similarity NPC114682
0.9091 High Similarity NPC249435
0.9065 High Similarity NPC231717
0.9038 High Similarity NPC70843
0.9009 High Similarity NPC158222
0.8981 High Similarity NPC11824
0.8981 High Similarity NPC242136
0.8962 High Similarity NPC88141
0.8942 High Similarity NPC219913
0.8929 High Similarity NPC159525
0.8879 High Similarity NPC21162
0.885 High Similarity NPC248363
0.885 High Similarity NPC297186
0.8846 High Similarity NPC120693
0.8846 High Similarity NPC261573
0.8846 High Similarity NPC8931
0.8824 High Similarity NPC280869
0.8774 High Similarity NPC34715
0.8774 High Similarity NPC29883
0.8772 High Similarity NPC267552
0.8772 High Similarity NPC120545
0.8772 High Similarity NPC143427
0.8772 High Similarity NPC156139
0.8772 High Similarity NPC19174
0.8772 High Similarity NPC73532
0.8772 High Similarity NPC115159
0.8772 High Similarity NPC45438
0.8772 High Similarity NPC224273
0.875 High Similarity NPC68269
0.8725 High Similarity NPC201967
0.8725 High Similarity NPC260000
0.8696 High Similarity NPC32032
0.8696 High Similarity NPC91478
0.8696 High Similarity NPC133909
0.8696 High Similarity NPC68167
0.8692 High Similarity NPC224584
0.8684 High Similarity NPC216216
0.8679 High Similarity NPC188677
0.8679 High Similarity NPC184658
0.8661 High Similarity NPC150919
0.8641 High Similarity NPC130193
0.8609 High Similarity NPC295034
0.8609 High Similarity NPC242895
0.8584 High Similarity NPC184527
0.8571 High Similarity NPC135784
0.8559 High Similarity NPC285350
0.8558 High Similarity NPC52472
0.8547 High Similarity NPC13238
0.8515 High Similarity NPC181709
0.8509 High Similarity NPC161617
0.8509 High Similarity NPC473767
0.8482 Intermediate Similarity NPC23402
0.8462 Intermediate Similarity NPC245561
0.8421 Intermediate Similarity NPC474890
0.8421 Intermediate Similarity NPC161943
0.8421 Intermediate Similarity NPC273282
0.8411 Intermediate Similarity NPC13495
0.8407 Intermediate Similarity NPC277394
0.8407 Intermediate Similarity NPC131192
0.8407 Intermediate Similarity NPC299252
0.8407 Intermediate Similarity NPC19290
0.8407 Intermediate Similarity NPC61062
0.8403 Intermediate Similarity NPC8745
0.8403 Intermediate Similarity NPC62952
0.8376 Intermediate Similarity NPC139171
0.8364 Intermediate Similarity NPC252544
0.8364 Intermediate Similarity NPC321252
0.8364 Intermediate Similarity NPC222905
0.8364 Intermediate Similarity NPC183648
0.8362 Intermediate Similarity NPC236520
0.8362 Intermediate Similarity NPC294361
0.8333 Intermediate Similarity NPC72158
0.8333 Intermediate Similarity NPC169250
0.8333 Intermediate Similarity NPC23126
0.8333 Intermediate Similarity NPC98254
0.8333 Intermediate Similarity NPC103356
0.8333 Intermediate Similarity NPC266689
0.8333 Intermediate Similarity NPC162612
0.8333 Intermediate Similarity NPC30501
0.8333 Intermediate Similarity NPC469954
0.8333 Intermediate Similarity NPC105157
0.8333 Intermediate Similarity NPC107672
0.8333 Intermediate Similarity NPC100067
0.8333 Intermediate Similarity NPC190043
0.8319 Intermediate Similarity NPC10926
0.8302 Intermediate Similarity NPC472585
0.8291 Intermediate Similarity NPC196976
0.8288 Intermediate Similarity NPC23332
0.8288 Intermediate Similarity NPC177576
0.8264 Intermediate Similarity NPC95537
0.8264 Intermediate Similarity NPC234175
0.8264 Intermediate Similarity NPC473017
0.8264 Intermediate Similarity NPC21305
0.8264 Intermediate Similarity NPC96024
0.8264 Intermediate Similarity NPC221777
0.8261 Intermediate Similarity NPC27633
0.8261 Intermediate Similarity NPC209486
0.8261 Intermediate Similarity NPC94298
0.8261 Intermediate Similarity NPC40649
0.8252 Intermediate Similarity NPC81010
0.8252 Intermediate Similarity NPC32977
0.825 Intermediate Similarity NPC267846
0.8246 Intermediate Similarity NPC83718
0.8246 Intermediate Similarity NPC128249
0.8241 Intermediate Similarity NPC163734
0.8235 Intermediate Similarity NPC164014
0.8235 Intermediate Similarity NPC45040
0.822 Intermediate Similarity NPC282577
0.822 Intermediate Similarity NPC309765
0.8214 Intermediate Similarity NPC286222
0.8205 Intermediate Similarity NPC190971
0.8197 Intermediate Similarity NPC120488
0.8197 Intermediate Similarity NPC474998
0.8197 Intermediate Similarity NPC102829
0.819 Intermediate Similarity NPC195262
0.819 Intermediate Similarity NPC188814
0.8182 Intermediate Similarity NPC116513
0.8174 Intermediate Similarity NPC174087
0.8173 Intermediate Similarity NPC286006
0.8165 Intermediate Similarity NPC317592
0.8165 Intermediate Similarity NPC187913
0.8158 Intermediate Similarity NPC161304
0.8158 Intermediate Similarity NPC240163
0.8158 Intermediate Similarity NPC278102
0.8158 Intermediate Similarity NPC160179
0.8151 Intermediate Similarity NPC174991
0.8148 Intermediate Similarity NPC249067
0.8136 Intermediate Similarity NPC303737
0.8136 Intermediate Similarity NPC198336
0.813 Intermediate Similarity NPC26697
0.813 Intermediate Similarity NPC66905
0.813 Intermediate Similarity NPC247779
0.812 Intermediate Similarity NPC294037
0.8115 Intermediate Similarity NPC2596
0.8103 Intermediate Similarity NPC311091
0.8103 Intermediate Similarity NPC471033
0.8099 Intermediate Similarity NPC254492
0.8099 Intermediate Similarity NPC305717
0.8091 Intermediate Similarity NPC303264
0.8091 Intermediate Similarity NPC228737
0.8087 Intermediate Similarity NPC325646
0.8087 Intermediate Similarity NPC28951
0.8087 Intermediate Similarity NPC108288
0.8083 Intermediate Similarity NPC199273
0.8077 Intermediate Similarity NPC128062
0.8077 Intermediate Similarity NPC151715
0.807 Intermediate Similarity NPC276111
0.807 Intermediate Similarity NPC118288
0.8067 Intermediate Similarity NPC67300
0.8067 Intermediate Similarity NPC300274
0.8067 Intermediate Similarity NPC283514
0.8065 Intermediate Similarity NPC475042
0.8065 Intermediate Similarity NPC469526
0.8065 Intermediate Similarity NPC93015
0.8065 Intermediate Similarity NPC34070
0.8056 Intermediate Similarity NPC13426
0.8053 Intermediate Similarity NPC51698
0.8053 Intermediate Similarity NPC17693
0.8051 Intermediate Similarity NPC149246
0.8051 Intermediate Similarity NPC146642
0.8049 Intermediate Similarity NPC476119
0.8049 Intermediate Similarity NPC92624
0.8049 Intermediate Similarity NPC276238
0.8034 Intermediate Similarity NPC61779
0.8033 Intermediate Similarity NPC72667
0.8033 Intermediate Similarity NPC22783
0.8033 Intermediate Similarity NPC78364
0.8033 Intermediate Similarity NPC69424
0.8033 Intermediate Similarity NPC176130
0.8033 Intermediate Similarity NPC84672
0.8018 Intermediate Similarity NPC100551
0.8018 Intermediate Similarity NPC317305
0.8017 Intermediate Similarity NPC123506
0.8017 Intermediate Similarity NPC269414
0.8 Intermediate Similarity NPC164236
0.8 Intermediate Similarity NPC308037
0.8 Intermediate Similarity NPC175313
0.8 Intermediate Similarity NPC112192
0.8 Intermediate Similarity NPC128348
0.8 Intermediate Similarity NPC309717
0.8 Intermediate Similarity NPC313618
0.8 Intermediate Similarity NPC262359
0.8 Intermediate Similarity NPC274678
0.8 Intermediate Similarity NPC26244
0.8 Intermediate Similarity NPC64359
0.8 Intermediate Similarity NPC375356
0.8 Intermediate Similarity NPC135801
0.8 Intermediate Similarity NPC66384
0.8 Intermediate Similarity NPC189106

  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 NPC17525 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
0.8774 High Similarity NPD9265 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD9545 Approved
0.819 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD1237 Approved
0.8087 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.8077 Intermediate Similarity NPD2934 Approved
0.8077 Intermediate Similarity NPD2933 Approved
0.8018 Intermediate Similarity NPD74 Approved
0.8018 Intermediate Similarity NPD9266 Approved
0.8017 Intermediate Similarity NPD1164 Approved
0.8 Intermediate Similarity NPD2860 Approved
0.8 Intermediate Similarity NPD2859 Approved
0.8 Intermediate Similarity NPD943 Approved
0.8 Intermediate Similarity NPD1240 Approved
0.7983 Intermediate Similarity NPD1201 Approved
0.7928 Intermediate Similarity NPD9267 Approved
0.7928 Intermediate Similarity NPD9263 Approved
0.7928 Intermediate Similarity NPD9264 Approved
0.7917 Intermediate Similarity NPD3972 Approved
0.7874 Intermediate Similarity NPD1607 Approved
0.7869 Intermediate Similarity NPD1470 Approved
0.7778 Intermediate Similarity NPD9493 Approved
0.7778 Intermediate Similarity NPD3020 Approved
0.7752 Intermediate Similarity NPD1510 Phase 2
0.7723 Intermediate Similarity NPD111 Approved
0.7698 Intermediate Similarity NPD3764 Approved
0.7692 Intermediate Similarity NPD9258 Approved
0.7692 Intermediate Similarity NPD9256 Approved
0.7672 Intermediate Similarity NPD1241 Discontinued
0.7642 Intermediate Similarity NPD1202 Approved
0.7634 Intermediate Similarity NPD2344 Approved
0.7615 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD9494 Approved
0.7581 Intermediate Similarity NPD1203 Approved
0.7576 Intermediate Similarity NPD1549 Phase 2
0.7568 Intermediate Similarity NPD9261 Approved
0.7545 Intermediate Similarity NPD1242 Phase 1
0.7521 Intermediate Similarity NPD3019 Approved
0.7521 Intermediate Similarity NPD2932 Approved
0.75 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1876 Approved
0.748 Intermediate Similarity NPD1481 Phase 2
0.748 Intermediate Similarity NPD9269 Phase 2
0.7458 Intermediate Similarity NPD9281 Approved
0.7438 Intermediate Similarity NPD9268 Approved
0.7411 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD1930 Approved
0.7411 Intermediate Similarity NPD1929 Approved
0.7407 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD2309 Approved
0.7398 Intermediate Similarity NPD1535 Discovery
0.7398 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD256 Approved
0.7395 Intermediate Similarity NPD255 Approved
0.7388 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD2798 Approved
0.7348 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD9568 Approved
0.7327 Intermediate Similarity NPD942 Approved
0.7308 Intermediate Similarity NPD9259 Approved
0.7308 Intermediate Similarity NPD9257 Approved
0.7297 Intermediate Similarity NPD1238 Approved
0.7293 Intermediate Similarity NPD2935 Discontinued
0.728 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.728 Intermediate Similarity NPD1755 Approved
0.7241 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD2799 Discontinued
0.7213 Intermediate Similarity NPD1894 Discontinued
0.7206 Intermediate Similarity NPD4628 Phase 3
0.7206 Intermediate Similarity NPD3750 Approved
0.7203 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD1608 Approved
0.72 Intermediate Similarity NPD9717 Approved
0.72 Intermediate Similarity NPD4878 Approved
0.7179 Intermediate Similarity NPD3022 Approved
0.7179 Intermediate Similarity NPD3021 Approved
0.7174 Intermediate Similarity NPD1511 Approved
0.7168 Intermediate Similarity NPD940 Approved
0.7168 Intermediate Similarity NPD846 Approved
0.7168 Intermediate Similarity NPD1932 Approved
0.7167 Intermediate Similarity NPD5951 Approved
0.7164 Intermediate Similarity NPD5405 Approved
0.7164 Intermediate Similarity NPD5406 Approved
0.7164 Intermediate Similarity NPD5404 Approved
0.7164 Intermediate Similarity NPD5408 Approved
0.7154 Intermediate Similarity NPD2313 Discontinued
0.7153 Intermediate Similarity NPD2354 Approved
0.7143 Intermediate Similarity NPD2066 Phase 3
0.7122 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD230 Phase 1
0.7087 Intermediate Similarity NPD1283 Approved
0.708 Intermediate Similarity NPD3028 Approved
0.7071 Intermediate Similarity NPD1512 Approved
0.7054 Intermediate Similarity NPD9495 Approved
0.705 Intermediate Similarity NPD7390 Discontinued
0.7045 Intermediate Similarity NPD3142 Approved
0.7045 Intermediate Similarity NPD3140 Approved
0.7037 Intermediate Similarity NPD2796 Approved
0.7031 Intermediate Similarity NPD2797 Approved
0.7027 Intermediate Similarity NPD1809 Phase 2
0.7027 Intermediate Similarity NPD844 Approved
0.7023 Intermediate Similarity NPD3268 Approved
0.7019 Intermediate Similarity NPD9491 Approved
0.7016 Intermediate Similarity NPD1651 Approved
0.7 Intermediate Similarity NPD845 Approved
0.6993 Remote Similarity NPD4380 Phase 2
0.6992 Remote Similarity NPD5536 Phase 2
0.6985 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6985 Remote Similarity NPD2353 Approved
0.6972 Remote Similarity NPD1239 Approved
0.697 Remote Similarity NPD520 Approved
0.6964 Remote Similarity NPD288 Approved
0.6963 Remote Similarity NPD4308 Phase 3
0.696 Remote Similarity NPD17 Approved
0.6957 Remote Similarity NPD7003 Approved
0.6935 Remote Similarity NPD1759 Phase 1
0.6934 Remote Similarity NPD970 Clinical (unspecified phase)
0.693 Remote Similarity NPD289 Clinical (unspecified phase)
0.6929 Remote Similarity NPD6799 Approved
0.6923 Remote Similarity NPD7458 Discontinued
0.6923 Remote Similarity NPD968 Approved
0.6912 Remote Similarity NPD1551 Phase 2
0.6905 Remote Similarity NPD3023 Approved
0.6905 Remote Similarity NPD3026 Approved
0.6905 Remote Similarity NPD3847 Discontinued
0.6897 Remote Similarity NPD9608 Approved
0.6897 Remote Similarity NPD9610 Approved
0.6894 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6893 Remote Similarity NPD1507 Clinical (unspecified phase)
0.688 Remote Similarity NPD3024 Approved
0.688 Remote Similarity NPD3025 Approved
0.6875 Remote Similarity NPD5157 Phase 1
0.6875 Remote Similarity NPD5159 Phase 2
0.6875 Remote Similarity NPD5158 Clinical (unspecified phase)
0.687 Remote Similarity NPD6832 Phase 2
0.6857 Remote Similarity NPD7440 Discontinued
0.6855 Remote Similarity NPD1758 Phase 1
0.685 Remote Similarity NPD1281 Approved
0.6838 Remote Similarity NPD3748 Approved
0.6828 Remote Similarity NPD7411 Suspended
0.6825 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6822 Remote Similarity NPD3225 Approved
0.6807 Remote Similarity NPD2329 Discontinued
0.6806 Remote Similarity NPD3229 Phase 2
0.6803 Remote Similarity NPD2229 Approved
0.6803 Remote Similarity NPD2228 Approved
0.6803 Remote Similarity NPD2234 Approved
0.6803 Remote Similarity NPD2296 Approved
0.68 Remote Similarity NPD9087 Approved
0.6786 Remote Similarity NPD3887 Approved
0.6786 Remote Similarity NPD688 Clinical (unspecified phase)
0.6786 Remote Similarity NPD9260 Approved
0.6786 Remote Similarity NPD6190 Approved
0.6781 Remote Similarity NPD7577 Discontinued
0.6781 Remote Similarity NPD1934 Approved
0.678 Remote Similarity NPD3134 Approved
0.6777 Remote Similarity NPD9508 Approved
0.6769 Remote Similarity NPD3267 Approved
0.6769 Remote Similarity NPD3266 Approved
0.6759 Remote Similarity NPD650 Approved
0.6757 Remote Similarity NPD3882 Suspended
0.6757 Remote Similarity NPD1508 Approved
0.6752 Remote Similarity NPD164 Approved
0.6752 Remote Similarity NPD5909 Discontinued
0.675 Remote Similarity NPD9380 Clinical (unspecified phase)
0.6748 Remote Similarity NPD690 Clinical (unspecified phase)
0.6739 Remote Similarity NPD2346 Discontinued
0.6739 Remote Similarity NPD1471 Phase 3
0.6739 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6738 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6738 Remote Similarity NPD3300 Phase 2
0.6735 Remote Similarity NPD2801 Approved
0.6735 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6723 Remote Similarity NPD2342 Discontinued
0.6723 Remote Similarity NPD1358 Approved
0.6721 Remote Similarity NPD5277 Phase 2
0.6719 Remote Similarity NPD422 Phase 1
0.6718 Remote Similarity NPD258 Approved
0.6718 Remote Similarity NPD257 Approved
0.6718 Remote Similarity NPD4980 Approved
0.6716 Remote Similarity NPD6663 Approved
0.6715 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6714 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6714 Remote Similarity NPD8166 Discontinued
0.6714 Remote Similarity NPD1196 Approved
0.6711 Remote Similarity NPD7075 Discontinued
0.6711 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6711 Remote Similarity NPD3749 Approved
0.6699 Remote Similarity NPD9088 Approved
0.6696 Remote Similarity NPD5122 Clinical (unspecified phase)
0.669 Remote Similarity NPD6143 Clinical (unspecified phase)
0.669 Remote Similarity NPD3455 Phase 2
0.669 Remote Similarity NPD1543 Discontinued
0.6689 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1566 Phase 3
0.6667 Remote Similarity NPD9569 Approved
0.6667 Remote Similarity NPD1564 Approved
0.6667 Remote Similarity NPD1548 Phase 1

  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