Structure

Physi-Chem Properties

Molecular Weight:  256.03
Volume:  254.027
LogP:  4.037
LogD:  3.745
LogS:  -5.331
# Rotatable Bonds:  1
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.722
Synthetic Accessibility Score:  1.908
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.744
MDCK Permeability:  1.2712106581602711e-05
Pgp-inhibitor:  0.64
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.032
Plasma Protein Binding (PPB):  100.55422973632812%
Volume Distribution (VD):  0.554
Pgp-substrate:  0.9357374310493469%

ADMET: Metabolism

CYP1A2-inhibitor:  0.984
CYP1A2-substrate:  0.174
CYP2C19-inhibitor:  0.905
CYP2C19-substrate:  0.084
CYP2C9-inhibitor:  0.747
CYP2C9-substrate:  0.045
CYP2D6-inhibitor:  0.272
CYP2D6-substrate:  0.105
CYP3A4-inhibitor:  0.153
CYP3A4-substrate:  0.205

ADMET: Excretion

Clearance (CL):  3.356
Half-life (T1/2):  0.085

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.949
Drug-inuced Liver Injury (DILI):  0.956
AMES Toxicity:  0.955
Rat Oral Acute Toxicity:  0.074
Maximum Recommended Daily Dose:  0.303
Skin Sensitization:  0.708
Carcinogencity:  0.818
Eye Corrosion:  0.004
Eye Irritation:  0.398
Respiratory Toxicity:  0.187

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

  Natural Product: NPC11173

Natural Product ID:  NPC11173
Common Name*:   (2Z)-2-[(4-Chlorophenyl)Methylidene]-1-Benzofuran-3-One
IUPAC Name:   (2Z)-2-[(4-chlorophenyl)methylidene]-1-benzofuran-3-one
Synonyms:   4'-Chloro-Aurone
Standard InCHIKey:  JIWJNEVCSMZRGO-ZROIWOOFSA-N
Standard InCHI:  InChI=1S/C15H9ClO2/c16-11-7-5-10(6-8-11)9-14-15(17)12-3-1-2-4-13(12)18-14/h1-9H/b14-9-
SMILES:  c1ccc2c(c1)C(=O)/C(=C/c1ccc(cc1)Cl)/O2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL596254
PubChem CID:   5467625
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0001631] Aurone 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
NPO22286 Spatoglossum variabile Species Dictyotaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(99)00213-7]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[7463094]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8201313]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8699182]
NPO22286 Spatoglossum variabile Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10476 Agaricus blazei Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22286 Spatoglossum variabile Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20310 Fagaropsis glabra Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24084 Polyalthia insignis Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23593 Drynaria quercifolia Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17035 Fusarium larvarum Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23827 Championella japonica n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23787 Martynia louisiana Species Martyniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21567 Salacia fruticosa Species Celastraceae 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
NPT582 Individual Protein Monoamine oxidase B Homo sapiens IC50 = 305.0 nM PMID[506409]
NPT261 Individual Protein Monoamine oxidase A Homo sapiens IC50 = 709.0 nM PMID[506409]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 37325.02 nM PMID[506410]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 23388.37 nM PMID[506410]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 96827.79 nM PMID[506410]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 20417.38 nM PMID[506410]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 16788.04 nM PMID[506410]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[506410]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 19724.23 nM PMID[506410]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 20606.3 nM PMID[506410]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 20370.42 nM PMID[506410]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[506410]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[506410]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 22335.72 nM PMID[506410]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 55590.43 nM PMID[506410]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 10000.0 nM PMID[506410]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 36307.81 nM PMID[506410]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 29853.83 nM PMID[506410]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 36982.82 nM PMID[506410]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 51168.18 nM PMID[506410]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[506410]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 22698.65 nM PMID[506410]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[506410]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 11748.98 nM PMID[506410]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 32359.37 nM PMID[506410]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 43752.21 nM PMID[506410]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 46451.53 nM PMID[506410]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 58210.32 nM PMID[506410]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 25644.84 nM PMID[506410]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 18706.82 nM PMID[506410]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 32658.78 nM PMID[506410]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[506410]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 66680.68 nM PMID[506410]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 51641.64 nM PMID[506410]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 59429.22 nM PMID[506410]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 30199.52 nM PMID[506410]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 22080.05 nM PMID[506410]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 10000.0 nM PMID[506410]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[506410]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 27352.69 nM PMID[506410]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 58613.82 nM PMID[506410]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 26424.09 nM PMID[506410]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 2760.58 nM PMID[506410]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 79250.13 nM PMID[506410]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 56493.7 nM PMID[506410]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 18663.8 nM PMID[506410]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 10000.0 nM PMID[506410]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 15739.83 nM PMID[506410]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 64714.26 nM PMID[506410]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[506410]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 38106.58 nM PMID[506410]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[506410]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[506410]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 21379.62 nM PMID[506410]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 47097.73 nM PMID[506410]
NPT83 Cell Line MCF7 Homo sapiens Activity = 85.0 % PMID[506411]
NPT65 Cell Line HepG2 Homo sapiens Activity = 110.0 % PMID[506411]
NPT139 Cell Line HT-29 Homo sapiens Inhibition = 68.7 % PMID[506412]
NPT139 Cell Line HT-29 Homo sapiens Ratio > 10.0 n.a. PMID[506412]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 10200.0 nM PMID[506413]
NPT616 Cell Line MDCK Canis lupus familiaris CC50 = 272400.0 nM PMID[506414]
NPT1602 Individual Protein Neuraminidase Influenza A virus (A/Puerto Rico/8/1934(H1N1)) IC50 = 45360.0 nM PMID[506414]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 0.0 % PMID[506408]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 4140000.0 nM PMID[506408]
NPT1 Others Radical scavenging activity Activity = 10.3 % PMID[506408]
NPT1 Others Radical scavenging activity Activity = 11.1 % PMID[506408]
NPT2 Others Unspecified Inhibition = 26.4 % PMID[506408]
NPT35 Others n.a. Inhibition = 46.4 % PMID[506408]
NPT1 Others Radical scavenging activity Activity = 49.3 % PMID[506408]
NPT1 Others Radical scavenging activity Activity = 76.2 % PMID[506408]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 89.5 % PMID[506408]
NPT664 Protein Family Histone deacetylase Homo sapiens Inhibition = 13.0 % PMID[506411]
NPT742 Organism Influenza A virus Influenza A virus EC50 = 51.39 nM PMID[506414]
NPT2 Others Unspecified Ratio CC50/EC50 = 5301.0 n.a. PMID[506414]

☑ 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 NPC11173 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
0.8571 High Similarity NPC32298
0.8504 High Similarity NPC54243
0.8504 High Similarity NPC35744
0.8462 Intermediate Similarity NPC93730
0.8308 Intermediate Similarity NPC314329
0.8154 Intermediate Similarity NPC246214
0.812 Intermediate Similarity NPC193805
0.8077 Intermediate Similarity NPC201284
0.806 Intermediate Similarity NPC2771
0.8031 Intermediate Similarity NPC279916
0.7971 Intermediate Similarity NPC324488
0.797 Intermediate Similarity NPC27198
0.7958 Intermediate Similarity NPC254841
0.7941 Intermediate Similarity NPC22783
0.7941 Intermediate Similarity NPC298884
0.791 Intermediate Similarity NPC472888
0.7883 Intermediate Similarity NPC125887
0.7883 Intermediate Similarity NPC196034
0.7863 Intermediate Similarity NPC152159
0.7863 Intermediate Similarity NPC206007
0.781 Intermediate Similarity NPC41721
0.7794 Intermediate Similarity NPC224657
0.7786 Intermediate Similarity NPC273984
0.777 Intermediate Similarity NPC7569
0.777 Intermediate Similarity NPC278787
0.7752 Intermediate Similarity NPC53953
0.7746 Intermediate Similarity NPC217914
0.7744 Intermediate Similarity NPC470092
0.7744 Intermediate Similarity NPC230951
0.7737 Intermediate Similarity NPC237868
0.773 Intermediate Similarity NPC128216
0.773 Intermediate Similarity NPC477536
0.7727 Intermediate Similarity NPC171023
0.7721 Intermediate Similarity NPC56332
0.7714 Intermediate Similarity NPC141549
0.7714 Intermediate Similarity NPC301717
0.7708 Intermediate Similarity NPC265181
0.7704 Intermediate Similarity NPC151237
0.7698 Intermediate Similarity NPC197425
0.7687 Intermediate Similarity NPC471520
0.766 Intermediate Similarity NPC284424
0.7652 Intermediate Similarity NPC217423
0.7652 Intermediate Similarity NPC45104
0.7647 Intermediate Similarity NPC141252
0.7647 Intermediate Similarity NPC11799
0.7643 Intermediate Similarity NPC228184
0.7643 Intermediate Similarity NPC115998
0.7643 Intermediate Similarity NPC39753
0.7639 Intermediate Similarity NPC61546
0.7639 Intermediate Similarity NPC72452
0.7639 Intermediate Similarity NPC477534
0.7634 Intermediate Similarity NPC188907
0.7622 Intermediate Similarity NPC248872
0.7619 Intermediate Similarity NPC310128
0.7609 Intermediate Similarity NPC474264
0.7606 Intermediate Similarity NPC287533
0.7591 Intermediate Similarity NPC107846
0.7589 Intermediate Similarity NPC137264
0.7586 Intermediate Similarity NPC299379
0.7576 Intermediate Similarity NPC316062
0.7574 Intermediate Similarity NPC311219
0.7571 Intermediate Similarity NPC473019
0.7552 Intermediate Similarity NPC292998
0.7552 Intermediate Similarity NPC57601
0.7536 Intermediate Similarity NPC470858
0.7536 Intermediate Similarity NPC4164
0.7535 Intermediate Similarity NPC66643
0.7535 Intermediate Similarity NPC278556
0.7535 Intermediate Similarity NPC113006
0.7519 Intermediate Similarity NPC469954
0.7518 Intermediate Similarity NPC182646
0.7517 Intermediate Similarity NPC216361
0.7517 Intermediate Similarity NPC256042
0.7517 Intermediate Similarity NPC281917
0.7517 Intermediate Similarity NPC187432
0.7517 Intermediate Similarity NPC116775
0.75 Intermediate Similarity NPC172262
0.75 Intermediate Similarity NPC136840
0.75 Intermediate Similarity NPC125269
0.7483 Intermediate Similarity NPC117463
0.7483 Intermediate Similarity NPC252208
0.7483 Intermediate Similarity NPC86847
0.7483 Intermediate Similarity NPC140840
0.7483 Intermediate Similarity NPC477537
0.7483 Intermediate Similarity NPC101294
0.7483 Intermediate Similarity NPC473655
0.7467 Intermediate Similarity NPC71210
0.7462 Intermediate Similarity NPC23332
0.7448 Intermediate Similarity NPC9985
0.7448 Intermediate Similarity NPC239495
0.7448 Intermediate Similarity NPC232996
0.7448 Intermediate Similarity NPC77955
0.7447 Intermediate Similarity NPC187907
0.7447 Intermediate Similarity NPC211120
0.7445 Intermediate Similarity NPC474283
0.7444 Intermediate Similarity NPC470860
0.7434 Intermediate Similarity NPC19545
0.7432 Intermediate Similarity NPC184536
0.7432 Intermediate Similarity NPC103904
0.7432 Intermediate Similarity NPC269652
0.7432 Intermediate Similarity NPC230285
0.7432 Intermediate Similarity NPC281207
0.7432 Intermediate Similarity NPC59951
0.7432 Intermediate Similarity NPC146679
0.7432 Intermediate Similarity NPC103342
0.7432 Intermediate Similarity NPC474037
0.7431 Intermediate Similarity NPC213216
0.7431 Intermediate Similarity NPC78540
0.7431 Intermediate Similarity NPC50898
0.7431 Intermediate Similarity NPC274121
0.7429 Intermediate Similarity NPC475496
0.7429 Intermediate Similarity NPC49852
0.7415 Intermediate Similarity NPC276905
0.7413 Intermediate Similarity NPC472882
0.741 Intermediate Similarity NPC88403
0.7407 Intermediate Similarity NPC137710
0.7397 Intermediate Similarity NPC254741
0.7397 Intermediate Similarity NPC240593
0.7386 Intermediate Similarity NPC226578
0.7385 Intermediate Similarity NPC183648
0.7383 Intermediate Similarity NPC262094
0.7383 Intermediate Similarity NPC90582
0.7379 Intermediate Similarity NPC66705
0.7376 Intermediate Similarity NPC475017
0.7376 Intermediate Similarity NPC50583
0.7376 Intermediate Similarity NPC473907
0.7368 Intermediate Similarity NPC471285
0.7365 Intermediate Similarity NPC143799
0.7365 Intermediate Similarity NPC241838
0.7365 Intermediate Similarity NPC477535
0.7365 Intermediate Similarity NPC152042
0.7361 Intermediate Similarity NPC229646
0.7353 Intermediate Similarity NPC233282
0.7351 Intermediate Similarity NPC474261
0.7347 Intermediate Similarity NPC84585
0.7347 Intermediate Similarity NPC157855
0.7347 Intermediate Similarity NPC103001
0.7347 Intermediate Similarity NPC476480
0.7347 Intermediate Similarity NPC266597
0.7347 Intermediate Similarity NPC228661
0.7347 Intermediate Similarity NPC290291
0.7347 Intermediate Similarity NPC250266
0.7347 Intermediate Similarity NPC188879
0.7347 Intermediate Similarity NPC275055
0.7343 Intermediate Similarity NPC205360
0.7338 Intermediate Similarity NPC260582
0.7333 Intermediate Similarity NPC53192
0.7329 Intermediate Similarity NPC99854
0.7329 Intermediate Similarity NPC163029
0.7328 Intermediate Similarity NPC233238
0.7324 Intermediate Similarity NPC66246
0.7324 Intermediate Similarity NPC57552
0.7324 Intermediate Similarity NPC473894
0.7324 Intermediate Similarity NPC170546
0.7324 Intermediate Similarity NPC939
0.731 Intermediate Similarity NPC247743
0.7305 Intermediate Similarity NPC45537
0.7305 Intermediate Similarity NPC470841
0.7305 Intermediate Similarity NPC264428
0.7303 Intermediate Similarity NPC250331
0.7297 Intermediate Similarity NPC99333
0.7297 Intermediate Similarity NPC188947
0.7297 Intermediate Similarity NPC124269
0.7297 Intermediate Similarity NPC473983
0.7297 Intermediate Similarity NPC329225
0.7297 Intermediate Similarity NPC280284
0.7297 Intermediate Similarity NPC201370
0.7297 Intermediate Similarity NPC147686
0.7297 Intermediate Similarity NPC18457
0.7297 Intermediate Similarity NPC472460
0.7293 Intermediate Similarity NPC252004
0.7292 Intermediate Similarity NPC313618
0.7292 Intermediate Similarity NPC308037
0.7292 Intermediate Similarity NPC262359
0.7292 Intermediate Similarity NPC64359
0.7292 Intermediate Similarity NPC118253
0.7292 Intermediate Similarity NPC474340
0.7287 Intermediate Similarity NPC141523
0.7286 Intermediate Similarity NPC52035
0.7286 Intermediate Similarity NPC65041
0.7285 Intermediate Similarity NPC302181
0.7285 Intermediate Similarity NPC225884
0.7285 Intermediate Similarity NPC470216
0.7285 Intermediate Similarity NPC17262
0.7279 Intermediate Similarity NPC231772
0.7279 Intermediate Similarity NPC301341
0.7279 Intermediate Similarity NPC284184
0.7279 Intermediate Similarity NPC194281
0.7279 Intermediate Similarity NPC473887
0.7279 Intermediate Similarity NPC13408
0.7279 Intermediate Similarity NPC161196
0.7279 Intermediate Similarity NPC124784
0.7279 Intermediate Similarity NPC29638
0.7279 Intermediate Similarity NPC127447
0.7279 Intermediate Similarity NPC234133
0.7279 Intermediate Similarity NPC47815
0.7279 Intermediate Similarity NPC264976
0.7279 Intermediate Similarity NPC29353
0.7273 Intermediate Similarity NPC183348
0.7273 Intermediate Similarity NPC282230

  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 NPC11173 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
0.8478 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.8478 Intermediate Similarity NPD2353 Approved
0.8308 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD3887 Approved
0.8239 Intermediate Similarity NPD2354 Approved
0.7794 Intermediate Similarity NPD1203 Approved
0.7762 Intermediate Similarity NPD1501 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD6832 Phase 2
0.7708 Intermediate Similarity NPD1471 Phase 3
0.7655 Intermediate Similarity NPD5958 Discontinued
0.7643 Intermediate Similarity NPD2313 Discontinued
0.7615 Intermediate Similarity NPD1241 Discontinued
0.7609 Intermediate Similarity NPD2798 Approved
0.7606 Intermediate Similarity NPD1184 Approved
0.7586 Intermediate Similarity NPD2344 Approved
0.7574 Intermediate Similarity NPD9717 Approved
0.7534 Intermediate Similarity NPD4534 Discontinued
0.7448 Intermediate Similarity NPD2799 Discontinued
0.74 Intermediate Similarity NPD6799 Approved
0.7397 Intermediate Similarity NPD2796 Approved
0.7383 Intermediate Similarity NPD2309 Approved
0.7361 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD1933 Approved
0.7357 Intermediate Similarity NPD1019 Discontinued
0.7351 Intermediate Similarity NPD5401 Approved
0.7324 Intermediate Similarity NPD2598 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD454 Approved
0.7297 Intermediate Similarity NPD1549 Phase 2
0.7292 Intermediate Similarity NPD1240 Approved
0.7255 Intermediate Similarity NPD5403 Approved
0.7248 Intermediate Similarity NPD1243 Approved
0.723 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD2346 Discontinued
0.7214 Intermediate Similarity NPD1876 Approved
0.7208 Intermediate Similarity NPD957 Approved
0.7194 Intermediate Similarity NPD3972 Approved
0.7192 Intermediate Similarity NPD1607 Approved
0.7172 Intermediate Similarity NPD4307 Phase 2
0.7163 Intermediate Similarity NPD3266 Approved
0.7163 Intermediate Similarity NPD3267 Approved
0.7162 Intermediate Similarity NPD1551 Phase 2
0.7132 Intermediate Similarity NPD9697 Approved
0.7124 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD2403 Approved
0.7115 Intermediate Similarity NPD6599 Discontinued
0.7114 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD3882 Suspended
0.7105 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD3748 Approved
0.7095 Intermediate Similarity NPD1510 Phase 2
0.7078 Intermediate Similarity NPD1512 Approved
0.707 Intermediate Similarity NPD958 Approved
0.707 Intermediate Similarity NPD3274 Phase 2
0.7059 Intermediate Similarity NPD9493 Approved
0.7042 Intermediate Similarity NPD2797 Approved
0.7034 Intermediate Similarity NPD411 Approved
0.7013 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD4661 Approved
0.7013 Intermediate Similarity NPD4662 Approved
0.7007 Intermediate Similarity NPD447 Suspended
0.7006 Intermediate Similarity NPD4972 Discontinued
0.6981 Remote Similarity NPD7096 Clinical (unspecified phase)
0.698 Remote Similarity NPD4308 Phase 3
0.6978 Remote Similarity NPD17 Approved
0.6977 Remote Similarity NPD9261 Approved
0.697 Remote Similarity NPD3366 Approved
0.6948 Remote Similarity NPD1511 Approved
0.6937 Remote Similarity NPD5402 Approved
0.6933 Remote Similarity NPD2935 Discontinued
0.6923 Remote Similarity NPD920 Approved
0.6918 Remote Similarity NPD6798 Discontinued
0.6918 Remote Similarity NPD6801 Discontinued
0.6918 Remote Similarity NPD3268 Approved
0.6918 Remote Similarity NPD6280 Approved
0.6918 Remote Similarity NPD6279 Approved
0.6914 Remote Similarity NPD919 Approved
0.6908 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6892 Remote Similarity NPD6355 Discontinued
0.6889 Remote Similarity NPD769 Approved
0.6879 Remote Similarity NPD2370 Clinical (unspecified phase)
0.6863 Remote Similarity NPD3750 Approved
0.6859 Remote Similarity NPD5049 Phase 3
0.6855 Remote Similarity NPD4424 Discontinued
0.6852 Remote Similarity NPD7075 Discontinued
0.6835 Remote Similarity NPD3226 Approved
0.6835 Remote Similarity NPD1894 Discontinued
0.6832 Remote Similarity NPD3817 Phase 2
0.6832 Remote Similarity NPD2379 Clinical (unspecified phase)
0.6832 Remote Similarity NPD2296 Approved
0.6831 Remote Similarity NPD1481 Phase 2
0.6831 Remote Similarity NPD4878 Approved
0.6831 Remote Similarity NPD1608 Approved
0.6829 Remote Similarity NPD1247 Approved
0.6824 Remote Similarity NPD3140 Approved
0.6824 Remote Similarity NPD3142 Approved
0.6818 Remote Similarity NPD3295 Clinical (unspecified phase)
0.6812 Remote Similarity NPD405 Clinical (unspecified phase)
0.6795 Remote Similarity NPD1578 Phase 2
0.6791 Remote Similarity NPD5451 Approved
0.6767 Remote Similarity NPD9267 Approved
0.6767 Remote Similarity NPD9264 Approved
0.6767 Remote Similarity NPD9263 Approved
0.6761 Remote Similarity NPD1201 Approved
0.6761 Remote Similarity NPD1535 Discovery
0.6755 Remote Similarity NPD5588 Approved
0.675 Remote Similarity NPD7411 Suspended
0.6748 Remote Similarity NPD3749 Approved
0.6747 Remote Similarity NPD3926 Phase 2
0.6744 Remote Similarity NPD1238 Approved
0.6736 Remote Similarity NPD3225 Approved
0.6716 Remote Similarity NPD74 Approved
0.6716 Remote Similarity NPD9266 Approved
0.6708 Remote Similarity NPD6844 Discontinued
0.669 Remote Similarity NPD987 Approved
0.669 Remote Similarity NPD1470 Approved
0.669 Remote Similarity NPD4879 Approved
0.6687 Remote Similarity NPD6585 Discontinued
0.6667 Remote Similarity NPD4359 Approved
0.6667 Remote Similarity NPD1651 Approved
0.6667 Remote Similarity NPD5494 Approved
0.6667 Remote Similarity NPD7819 Suspended
0.6646 Remote Similarity NPD5889 Approved
0.6646 Remote Similarity NPD5890 Approved
0.6645 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6644 Remote Similarity NPD6233 Phase 2
0.6644 Remote Similarity NPD4062 Phase 3
0.6642 Remote Similarity NPD5535 Approved
0.6623 Remote Similarity NPD2897 Discontinued
0.662 Remote Similarity NPD6516 Phase 2
0.662 Remote Similarity NPD5846 Approved
0.6607 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6605 Remote Similarity NPD1934 Approved
0.6604 Remote Similarity NPD3869 Phase 3
0.6604 Remote Similarity NPD3873 Phase 3
0.6592 Remote Similarity NPD4361 Phase 2
0.6592 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6587 Remote Similarity NPD6808 Phase 2
0.6584 Remote Similarity NPD4380 Phase 2
0.6581 Remote Similarity NPD2654 Approved
0.6581 Remote Similarity NPD2800 Approved
0.6579 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6579 Remote Similarity NPD4538 Approved
0.6579 Remote Similarity NPD4536 Approved
0.6577 Remote Similarity NPD3764 Approved
0.6577 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6577 Remote Similarity NPD1296 Phase 2
0.6575 Remote Similarity NPD1164 Approved
0.6569 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6567 Remote Similarity NPD968 Approved
0.6564 Remote Similarity NPD2801 Approved
0.6564 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6558 Remote Similarity NPD7611 Approved
0.6558 Remote Similarity NPD2377 Approved
0.6558 Remote Similarity NPD2376 Approved
0.6558 Remote Similarity NPD2378 Approved
0.6556 Remote Similarity NPD4622 Approved
0.6556 Remote Similarity NPD4618 Approved
0.6549 Remote Similarity NPD5585 Approved
0.6547 Remote Similarity NPD690 Clinical (unspecified phase)
0.6545 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6543 Remote Similarity NPD2366 Approved
0.6541 Remote Similarity NPD1237 Approved
0.6538 Remote Similarity NPD4628 Phase 3
0.6536 Remote Similarity NPD7033 Discontinued
0.6536 Remote Similarity NPD5960 Phase 3
0.6528 Remote Similarity NPD1281 Approved
0.6525 Remote Similarity NPD5536 Phase 2
0.6524 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6524 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6522 Remote Similarity NPD3769 Discontinued
0.6516 Remote Similarity NPD970 Clinical (unspecified phase)
0.6514 Remote Similarity NPD1163 Approved
0.6485 Remote Similarity NPD7768 Phase 2
0.6479 Remote Similarity NPD9545 Approved
0.6471 Remote Similarity NPD5688 Approved
0.6471 Remote Similarity NPD5689 Approved
0.6463 Remote Similarity NPD1049 Clinical (unspecified phase)
0.6461 Remote Similarity NPD5626 Phase 3
0.6461 Remote Similarity NPD5625 Phase 3
0.6461 Remote Similarity NPD5624 Phase 3
0.6458 Remote Similarity NPD1889 Phase 1
0.6456 Remote Similarity NPD5058 Phase 3
0.6456 Remote Similarity NPD7440 Discontinued
0.6444 Remote Similarity NPD4363 Phase 3
0.6444 Remote Similarity NPD3134 Approved
0.6444 Remote Similarity NPD4360 Phase 2
0.6438 Remote Similarity NPD6273 Approved
0.6438 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6433 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6433 Remote Similarity NPD3818 Discontinued
0.6433 Remote Similarity NPD7003 Approved
0.6429 Remote Similarity NPD9281 Approved
0.6424 Remote Similarity NPD8032 Phase 2
0.642 Remote Similarity NPD5808 Clinical (unspecified phase)
0.642 Remote Similarity NPD2651 Approved
0.642 Remote Similarity NPD2649 Approved
0.6418 Remote Similarity NPD9501 Approved
0.6414 Remote Similarity NPD422 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