Structure

Physi-Chem Properties

Molecular Weight:  374.08
Volume:  375.946
LogP:  4.304
LogD:  2.562
LogS:  -5.454
# Rotatable Bonds:  0
TPSA:  115.06
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.445
Synthetic Accessibility Score:  3.647
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.953
MDCK Permeability:  3.87529689760413e-06
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.628
20% Bioavailability (F20%):  0.644
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.002
Plasma Protein Binding (PPB):  93.07615661621094%
Volume Distribution (VD):  0.617
Pgp-substrate:  10.437456130981445%

ADMET: Metabolism

CYP1A2-inhibitor:  0.982
CYP1A2-substrate:  0.085
CYP2C19-inhibitor:  0.092
CYP2C19-substrate:  0.053
CYP2C9-inhibitor:  0.659
CYP2C9-substrate:  0.568
CYP2D6-inhibitor:  0.231
CYP2D6-substrate:  0.183
CYP3A4-inhibitor:  0.164
CYP3A4-substrate:  0.037

ADMET: Excretion

Clearance (CL):  7.935
Half-life (T1/2):  0.534

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.438
Drug-inuced Liver Injury (DILI):  0.981
AMES Toxicity:  0.596
Rat Oral Acute Toxicity:  0.286
Maximum Recommended Daily Dose:  0.93
Skin Sensitization:  0.961
Carcinogencity:  0.658
Eye Corrosion:  0.026
Eye Irritation:  0.958
Respiratory Toxicity:  0.135

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC50924

Natural Product ID:  NPC50924
Common Name*:   5-Hydroxy-6-(4-Hydroxy-2-Methyl-5,8-Dioxonaphthalen-1-Yl)-7-Methylnaphthalene-1,4-Dione
IUPAC Name:   5-hydroxy-6-(4-hydroxy-2-methyl-5,8-dioxonaphthalen-1-yl)-7-methylnaphthalene-1,4-dione
Synonyms:  
Standard InCHIKey:  OEEOHKZVBKYMBA-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C22H14O6/c1-9-7-11-12(23)3-4-13(24)19(11)22(28)18(9)17-10(2)8-16(27)20-14(25)5-6-15(26)21(17)20/h3-8,27-28H,1-2H3
SMILES:  Cc1cc2C(=O)C=CC(=O)c2c(c1c1c(C)cc(c2C(=O)C=CC(=O)c12)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1992900
PubChem CID:   99298
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0000153] Naphthoquinones

*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
NPO20123 Actinidia polygama Species Actinidiaceae Eukaryota n.a. n.a. n.a. PMID[6061704]
NPO25037 Nepeta cataria Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20123 Actinidia polygama Species Actinidiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24185 Diospyros lotus Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26811 Gynostemma yixingense Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26811 Gynostemma yixingense Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25037 Nepeta cataria Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20123 Actinidia polygama Species Actinidiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24185 Diospyros lotus Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20123 Actinidia polygama Species Actinidiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25037 Nepeta cataria Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24185 Diospyros lotus Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14867 Acer griseum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26811 Gynostemma yixingense Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5003 Amelanchier spicata Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2606 Hypnum cupressiforme Species Hypnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25037 Nepeta cataria Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15262 Dunaliella tertiolecta Species Dunaliellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24185 Diospyros lotus Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20123 Actinidia polygama Species Actinidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8769 Mythimna loreyi Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12995 Adenia cissampeloides Species Passifloraceae 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 1462.18 nM PMID[486072]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 2371.37 nM PMID[486072]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 388.15 nM PMID[486072]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 3047.89 nM PMID[486072]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 1625.55 nM PMID[486072]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 10.0 nM PMID[486072]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 413.05 nM PMID[486072]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 2192.8 nM PMID[486072]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 2884.03 nM PMID[486072]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 4008.67 nM PMID[486072]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 341.98 nM PMID[486072]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 33.73 nM PMID[486072]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 6760.83 nM PMID[486072]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 2084.49 nM PMID[486072]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 22.39 nM PMID[486072]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 20276.83 nM PMID[486072]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 2488.86 nM PMID[486072]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 1945.36 nM PMID[486072]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 4027.17 nM PMID[486072]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 2624.22 nM PMID[486072]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 18030.18 nM PMID[486072]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 1999.86 nM PMID[486072]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 42.95 nM PMID[486072]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 855.07 nM PMID[486072]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 1588.55 nM PMID[486072]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 10280.16 nM PMID[486072]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 135.83 nM PMID[486072]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 2177.71 nM PMID[486072]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 17179.08 nM PMID[486072]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 226.46 nM PMID[486072]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 2999.16 nM PMID[486072]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 1109.17 nM PMID[486072]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 2606.15 nM PMID[486072]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 10046.16 nM PMID[486072]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 3126.08 nM PMID[486072]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 17741.89 nM PMID[486072]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 5495.41 nM PMID[486072]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 1213.39 nM PMID[486072]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 1524.05 nM PMID[486072]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 1918.67 nM PMID[486072]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 1592.21 nM PMID[486072]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 4017.91 nM PMID[486072]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 966.05 nM PMID[486072]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 15595.53 nM PMID[486072]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 1342.76 nM PMID[486072]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 6426.88 nM PMID[486072]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 2128.14 nM PMID[486072]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 630.96 nM PMID[486072]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 1945.36 nM PMID[486072]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 16672.47 nM PMID[486072]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 2264.64 nM PMID[486072]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 3069.02 nM PMID[486072]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 1161.45 nM PMID[486072]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 1618.08 nM PMID[486072]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 10.0 nM PMID[486072]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 1581.25 nM PMID[486072]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 20183.66 nM PMID[486072]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 368.98 nM PMID[486072]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 756.83 nM PMID[486072]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 278.61 nM PMID[486072]
NPT22359 PROTEIN COMPLEX DNA gyrase subunit A/DNA gyrase subunit B Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) IC50 = 100000.0 nM PMID[486073]
NPT2 Others Unspecified IC50 = 100000.0 nM PMID[486074]

☑ 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 NPC50924 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
0.9764 High Similarity NPC244699
0.9612 High Similarity NPC53896
0.9606 High Similarity NPC34414
0.9606 High Similarity NPC146647
0.9531 High Similarity NPC55949
0.9466 High Similarity NPC283088
0.9462 High Similarity NPC225051
0.9318 High Similarity NPC80035
0.9254 High Similarity NPC13715
0.9248 High Similarity NPC155211
0.9237 High Similarity NPC58685
0.9225 High Similarity NPC48248
0.9225 High Similarity NPC96024
0.9167 High Similarity NPC52407
0.9154 High Similarity NPC99731
0.9124 High Similarity NPC19631
0.9124 High Similarity NPC239136
0.9111 High Similarity NPC4214
0.9077 High Similarity NPC282923
0.9062 High Similarity NPC142956
0.9055 High Similarity NPC307174
0.9051 High Similarity NPC246638
0.9044 High Similarity NPC138099
0.9044 High Similarity NPC242994
0.9037 High Similarity NPC471905
0.9037 High Similarity NPC53206
0.9037 High Similarity NPC53414
0.903 High Similarity NPC258502
0.9015 High Similarity NPC72669
0.9015 High Similarity NPC474517
0.8984 High Similarity NPC375356
0.8978 High Similarity NPC181560
0.8978 High Similarity NPC169452
0.8971 High Similarity NPC61398
0.8971 High Similarity NPC416
0.8963 High Similarity NPC474813
0.8963 High Similarity NPC254847
0.8939 High Similarity NPC136588
0.8939 High Similarity NPC199253
0.8923 High Similarity NPC254492
0.8923 High Similarity NPC3224
0.8923 High Similarity NPC160499
0.8915 High Similarity NPC199273
0.8906 High Similarity NPC91478
0.8906 High Similarity NPC300274
0.8897 High Similarity NPC245923
0.8897 High Similarity NPC305060
0.8897 High Similarity NPC53001
0.8897 High Similarity NPC36868
0.8881 High Similarity NPC294226
0.8881 High Similarity NPC115458
0.8872 High Similarity NPC93015
0.8872 High Similarity NPC205992
0.8864 High Similarity NPC276238
0.8855 High Similarity NPC72667
0.8849 High Similarity NPC193555
0.8849 High Similarity NPC69755
0.8846 High Similarity NPC103540
0.8841 High Similarity NPC96421
0.8832 High Similarity NPC87723
0.8828 High Similarity NPC120545
0.8824 High Similarity NPC315275
0.8819 High Similarity NPC285829
0.8819 High Similarity NPC206778
0.8815 High Similarity NPC12070
0.8815 High Similarity NPC166480
0.8815 High Similarity NPC282780
0.8815 High Similarity NPC44437
0.8806 High Similarity NPC70622
0.8797 High Similarity NPC27659
0.8797 High Similarity NPC31799
0.8797 High Similarity NPC117609
0.8786 High Similarity NPC66593
0.8779 High Similarity NPC306765
0.8779 High Similarity NPC96915
0.8779 High Similarity NPC231774
0.8777 High Similarity NPC204045
0.8777 High Similarity NPC305845
0.8769 High Similarity NPC310540
0.8769 High Similarity NPC173978
0.8768 High Similarity NPC26924
0.8768 High Similarity NPC470407
0.8768 High Similarity NPC143438
0.876 High Similarity NPC282577
0.875 High Similarity NPC249272
0.8741 High Similarity NPC267205
0.8741 High Similarity NPC314048
0.8741 High Similarity NPC114183
0.8731 High Similarity NPC17083
0.8723 High Similarity NPC79627
0.8723 High Similarity NPC21599
0.8723 High Similarity NPC193703
0.8722 High Similarity NPC171460
0.8714 High Similarity NPC135524
0.8714 High Similarity NPC469520
0.8712 High Similarity NPC84672
0.8712 High Similarity NPC176130
0.8712 High Similarity NPC78364
0.8712 High Similarity NPC69424
0.8705 High Similarity NPC315578
0.869 High Similarity NPC144283
0.8686 High Similarity NPC191976
0.8686 High Similarity NPC474311
0.8686 High Similarity NPC193358
0.8686 High Similarity NPC272268
0.8676 High Similarity NPC288089
0.8676 High Similarity NPC270899
0.8671 High Similarity NPC37709
0.8657 High Similarity NPC108129
0.8657 High Similarity NPC198305
0.8652 High Similarity NPC296752
0.8652 High Similarity NPC471682
0.8636 High Similarity NPC15837
0.8633 High Similarity NPC190457
0.8626 High Similarity NPC164014
0.8621 High Similarity NPC205766
0.8603 High Similarity NPC171968
0.8601 High Similarity NPC314437
0.8593 High Similarity NPC41847
0.8593 High Similarity NPC85342
0.8592 High Similarity NPC244691
0.8592 High Similarity NPC471906
0.8592 High Similarity NPC48762
0.8582 High Similarity NPC73061
0.8582 High Similarity NPC278928
0.8582 High Similarity NPC257644
0.8571 High Similarity NPC471530
0.8561 High Similarity NPC123506
0.8551 High Similarity NPC86524
0.8551 High Similarity NPC118919
0.8542 High Similarity NPC119767
0.854 High Similarity NPC287604
0.854 High Similarity NPC161964
0.854 High Similarity NPC202225
0.854 High Similarity NPC472262
0.8531 High Similarity NPC478019
0.8531 High Similarity NPC34482
0.8531 High Similarity NPC471683
0.8529 High Similarity NPC175738
0.8529 High Similarity NPC309430
0.8521 High Similarity NPC313047
0.8521 High Similarity NPC474203
0.8521 High Similarity NPC451542
0.8521 High Similarity NPC295712
0.8521 High Similarity NPC53016
0.8519 High Similarity NPC31539
0.8511 High Similarity NPC290550
0.8511 High Similarity NPC110810
0.8511 High Similarity NPC477275
0.8507 High Similarity NPC234175
0.8507 High Similarity NPC237225
0.8507 High Similarity NPC95537
0.8504 High Similarity NPC108288
0.85 High Similarity NPC1268
0.8489 Intermediate Similarity NPC471452
0.8489 Intermediate Similarity NPC264022
0.8489 Intermediate Similarity NPC62272
0.8489 Intermediate Similarity NPC147418
0.8485 Intermediate Similarity NPC68756
0.8485 Intermediate Similarity NPC236189
0.8485 Intermediate Similarity NPC152525
0.8478 Intermediate Similarity NPC161632
0.8478 Intermediate Similarity NPC153088
0.8473 Intermediate Similarity NPC176208
0.8472 Intermediate Similarity NPC110882
0.8472 Intermediate Similarity NPC271944
0.8472 Intermediate Similarity NPC85393
0.8472 Intermediate Similarity NPC470570
0.8472 Intermediate Similarity NPC143685
0.8472 Intermediate Similarity NPC147250
0.8467 Intermediate Similarity NPC138472
0.8462 Intermediate Similarity NPC10764
0.8462 Intermediate Similarity NPC472046
0.8462 Intermediate Similarity NPC190971
0.8462 Intermediate Similarity NPC227841
0.8456 Intermediate Similarity NPC471851
0.8451 Intermediate Similarity NPC85310
0.8451 Intermediate Similarity NPC474961
0.8444 Intermediate Similarity NPC92624
0.8444 Intermediate Similarity NPC303910
0.844 Intermediate Similarity NPC203063
0.8425 Intermediate Similarity NPC161304
0.8417 Intermediate Similarity NPC475549
0.8414 Intermediate Similarity NPC56433
0.8414 Intermediate Similarity NPC118027
0.8414 Intermediate Similarity NPC472135
0.8414 Intermediate Similarity NPC289042
0.8414 Intermediate Similarity NPC312929
0.8414 Intermediate Similarity NPC190648
0.8414 Intermediate Similarity NPC245584
0.8414 Intermediate Similarity NPC126767
0.8403 Intermediate Similarity NPC12402
0.8397 Intermediate Similarity NPC154696
0.8394 Intermediate Similarity NPC242358
0.8394 Intermediate Similarity NPC110609
0.8394 Intermediate Similarity NPC246693
0.8392 Intermediate Similarity NPC293545
0.8392 Intermediate Similarity NPC174905
0.8389 Intermediate Similarity NPC66029
0.8389 Intermediate Similarity NPC66508

  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 NPC50924 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
0.8963 High Similarity NPD1509 Clinical (unspecified phase)
0.8846 High Similarity NPD1470 Approved
0.8538 High Similarity NPD1201 Approved
0.8504 High Similarity NPD405 Clinical (unspecified phase)
0.8489 Intermediate Similarity NPD5405 Approved
0.8489 Intermediate Similarity NPD5406 Approved
0.8489 Intermediate Similarity NPD5404 Approved
0.8489 Intermediate Similarity NPD5408 Approved
0.8462 Intermediate Similarity NPD7390 Discontinued
0.8042 Intermediate Similarity NPD2346 Discontinued
0.8027 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.8015 Intermediate Similarity NPD1164 Approved
0.8 Intermediate Similarity NPD943 Approved
0.7933 Intermediate Similarity NPD3226 Approved
0.7917 Intermediate Similarity NPD2344 Approved
0.7891 Intermediate Similarity NPD3300 Phase 2
0.7836 Intermediate Similarity NPD2932 Approved
0.7761 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD2935 Discontinued
0.7722 Intermediate Similarity NPD6232 Discontinued
0.7704 Intermediate Similarity NPD3019 Approved
0.7703 Intermediate Similarity NPD2309 Approved
0.7688 Intermediate Similarity NPD7473 Discontinued
0.7655 Intermediate Similarity NPD2799 Discontinued
0.7655 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD1607 Approved
0.7635 Intermediate Similarity NPD7003 Approved
0.7547 Intermediate Similarity NPD6959 Discontinued
0.7534 Intermediate Similarity NPD1510 Phase 2
0.7534 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD2342 Discontinued
0.75 Intermediate Similarity NPD1240 Approved
0.75 Intermediate Similarity NPD7819 Suspended
0.7483 Intermediate Similarity NPD3764 Approved
0.7483 Intermediate Similarity NPD2313 Discontinued
0.7447 Intermediate Similarity NPD2798 Approved
0.7434 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD1471 Phase 3
0.7429 Intermediate Similarity NPD1283 Approved
0.74 Intermediate Similarity NPD3750 Approved
0.7388 Intermediate Similarity NPD5951 Approved
0.7372 Intermediate Similarity NPD1651 Approved
0.7368 Intermediate Similarity NPD7635 Approved
0.7358 Intermediate Similarity NPD3749 Approved
0.7355 Intermediate Similarity NPD7458 Discontinued
0.7353 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD2533 Approved
0.732 Intermediate Similarity NPD2534 Approved
0.732 Intermediate Similarity NPD2532 Approved
0.7319 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD4380 Phase 2
0.7286 Intermediate Similarity NPD3972 Approved
0.7278 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1549 Phase 2
0.7266 Intermediate Similarity NPD3023 Approved
0.7266 Intermediate Similarity NPD3026 Approved
0.7246 Intermediate Similarity NPD3024 Approved
0.7246 Intermediate Similarity NPD3025 Approved
0.7244 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD8150 Discontinued
0.7233 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7214 Intermediate Similarity NPD1281 Approved
0.72 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD74 Approved
0.7197 Intermediate Similarity NPD9266 Approved
0.7183 Intermediate Similarity NPD1876 Approved
0.7171 Intermediate Similarity NPD8166 Discontinued
0.7163 Intermediate Similarity NPD4878 Approved
0.7153 Intermediate Similarity NPD9493 Approved
0.7152 Intermediate Similarity NPD7411 Suspended
0.7143 Intermediate Similarity NPD1511 Approved
0.7125 Intermediate Similarity NPD2296 Approved
0.7121 Intermediate Similarity NPD9267 Approved
0.7121 Intermediate Similarity NPD9263 Approved
0.7121 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD9264 Approved
0.7107 Intermediate Similarity NPD1934 Approved
0.7105 Intermediate Similarity NPD2800 Approved
0.7091 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD7768 Phase 2
0.7071 Intermediate Similarity NPD4626 Approved
0.7071 Intermediate Similarity NPD2286 Discontinued
0.7069 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD3748 Approved
0.7066 Intermediate Similarity NPD5844 Phase 1
0.7063 Intermediate Similarity NPD2801 Approved
0.7051 Intermediate Similarity NPD1512 Approved
0.7037 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7075 Discontinued
0.702 Intermediate Similarity NPD2796 Approved
0.7014 Intermediate Similarity NPD1203 Approved
0.7 Intermediate Similarity NPD1932 Approved
0.6977 Remote Similarity NPD3020 Approved
0.6975 Remote Similarity NPD3882 Suspended
0.6974 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6972 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6964 Remote Similarity NPD6020 Phase 2
0.6959 Remote Similarity NPD6663 Approved
0.6957 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6954 Remote Similarity NPD4308 Phase 3
0.6953 Remote Similarity NPD288 Approved
0.6951 Remote Similarity NPD5494 Approved
0.695 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6948 Remote Similarity NPD4628 Phase 3
0.6947 Remote Similarity NPD1929 Approved
0.6947 Remote Similarity NPD1930 Approved
0.6947 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6943 Remote Similarity NPD6273 Approved
0.6941 Remote Similarity NPD5029 Approved
0.6941 Remote Similarity NPD5027 Approved
0.6941 Remote Similarity NPD5031 Approved
0.694 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6939 Remote Similarity NPD7008 Discontinued
0.6929 Remote Similarity NPD9545 Approved
0.6918 Remote Similarity NPD5736 Approved
0.6914 Remote Similarity NPD8438 Clinical (unspecified phase)
0.6913 Remote Similarity NPD2979 Phase 3
0.6905 Remote Similarity NPD7177 Discontinued
0.6901 Remote Similarity NPD4955 Approved
0.6901 Remote Similarity NPD4954 Approved
0.6901 Remote Similarity NPD36 Approved
0.6901 Remote Similarity NPD5028 Approved
0.6901 Remote Similarity NPD5026 Approved
0.6901 Remote Similarity NPD5034 Approved
0.6893 Remote Similarity NPD6535 Approved
0.6893 Remote Similarity NPD6534 Approved
0.6892 Remote Similarity NPD411 Approved
0.6889 Remote Similarity NPD3022 Approved
0.6889 Remote Similarity NPD3021 Approved
0.6884 Remote Similarity NPD9281 Approved
0.6884 Remote Similarity NPD497 Approved
0.6875 Remote Similarity NPD2859 Approved
0.6875 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6875 Remote Similarity NPD2860 Approved
0.6875 Remote Similarity NPD844 Approved
0.6875 Remote Similarity NPD6599 Discontinued
0.686 Remote Similarity NPD8312 Approved
0.686 Remote Similarity NPD8313 Approved
0.6852 Remote Similarity NPD1465 Phase 2
0.6842 Remote Similarity NPD5030 Phase 2
0.6842 Remote Similarity NPD6559 Discontinued
0.6839 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6838 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6836 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6836 Remote Similarity NPD6213 Phase 3
0.6836 Remote Similarity NPD6212 Phase 3
0.6829 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6824 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6821 Remote Similarity NPD6651 Approved
0.6818 Remote Similarity NPD9261 Approved
0.6815 Remote Similarity NPD2329 Discontinued
0.6812 Remote Similarity NPD498 Approved
0.6812 Remote Similarity NPD496 Approved
0.6812 Remote Similarity NPD495 Approved
0.6809 Remote Similarity NPD3091 Approved
0.6806 Remote Similarity NPD9717 Approved
0.6806 Remote Similarity NPD9269 Phase 2
0.6803 Remote Similarity NPD9494 Approved
0.6797 Remote Similarity NPD1551 Phase 2
0.6797 Remote Similarity NPD2934 Approved
0.6797 Remote Similarity NPD6100 Approved
0.6797 Remote Similarity NPD6099 Approved
0.6797 Remote Similarity NPD2933 Approved
0.6796 Remote Similarity NPD6778 Approved
0.6796 Remote Similarity NPD6782 Approved
0.6796 Remote Similarity NPD6779 Approved
0.6796 Remote Similarity NPD6781 Approved
0.6796 Remote Similarity NPD6777 Approved
0.6796 Remote Similarity NPD6776 Approved
0.6796 Remote Similarity NPD6780 Approved
0.679 Remote Similarity NPD6801 Discontinued
0.6786 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6786 Remote Similarity NPD6166 Phase 2
0.6786 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6783 Remote Similarity NPD4879 Approved
0.678 Remote Similarity NPD5968 Phase 3
0.6779 Remote Similarity NPD3268 Approved
0.6778 Remote Similarity NPD7699 Phase 2
0.6778 Remote Similarity NPD7700 Phase 2
0.6774 Remote Similarity NPD1243 Approved
0.6767 Remote Similarity NPD1237 Approved
0.6766 Remote Similarity NPD5710 Approved
0.6766 Remote Similarity NPD5711 Approved
0.6765 Remote Similarity NPD4750 Phase 3
0.6761 Remote Similarity NPD5691 Approved
0.6761 Remote Similarity NPD9268 Approved
0.6759 Remote Similarity NPD1755 Approved
0.6755 Remote Similarity NPD447 Suspended
0.6743 Remote Similarity NPD5037 Approved
0.6743 Remote Similarity NPD5038 Approved
0.6731 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6713 Remote Similarity NPD4059 Approved
0.6711 Remote Similarity NPD4625 Phase 3
0.6709 Remote Similarity NPD6799 Approved
0.6706 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6706 Remote Similarity NPD3818 Discontinued

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data