Structure

Physi-Chem Properties

Molecular Weight:  190.03
Volume:  183.746
LogP:  1.993
LogD:  1.733
LogS:  -3.511
# Rotatable Bonds:  0
TPSA:  74.6
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.599
Synthetic Accessibility Score:  2.431
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.724
MDCK Permeability:  1.3356461749935988e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.16

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.106
Plasma Protein Binding (PPB):  96.27594757080078%
Volume Distribution (VD):  0.454
Pgp-substrate:  2.454972267150879%

ADMET: Metabolism

CYP1A2-inhibitor:  0.95
CYP1A2-substrate:  0.12
CYP2C19-inhibitor:  0.1
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.348
CYP2C9-substrate:  0.773
CYP2D6-inhibitor:  0.437
CYP2D6-substrate:  0.342
CYP3A4-inhibitor:  0.74
CYP3A4-substrate:  0.141

ADMET: Excretion

Clearance (CL):  10.575
Half-life (T1/2):  0.68

ADMET: Toxicity

hERG Blockers:  0.012
Human Hepatotoxicity (H-HT):  0.269
Drug-inuced Liver Injury (DILI):  0.869
AMES Toxicity:  0.85
Rat Oral Acute Toxicity:  0.788
Maximum Recommended Daily Dose:  0.705
Skin Sensitization:  0.919
Carcinogencity:  0.768
Eye Corrosion:  0.703
Eye Irritation:  0.988
Respiratory Toxicity:  0.34

Download Data

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

  Natural Product: NPC232178

Natural Product ID:  NPC232178
Common Name*:   Naphthazalin
IUPAC Name:   5,8-dihydroxynaphthalene-1,4-dione
Synonyms:   5,8-Dihydroxy-[1,4]Naphthoquinone; Naphthazalin
Standard InCHIKey:  RQNVIKXOOKXAJQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H
SMILES:  c1cc(c2C(=O)C=CC(=O)c2c1O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL274056
PubChem CID:   10141
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
NPO40718 Indian beech tree Strain n.a. n.a. n.a. n.a. n.a. PMID[30108931]
NPO26892.1 Juglans mandshurica var. sieboldiana Varieties Juglandaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26892.1 Juglans mandshurica var. sieboldiana Varieties Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26892.1 Juglans mandshurica var. sieboldiana Varieties Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT3021 Individual Protein Arachidonate 5-lipoxygenase Bos taurus IC50 = 3000.0 nM PMID[450041]
NPT941 Cell Line HaCaT Homo sapiens IC50 = 700.0 nM PMID[450041]
NPT941 Cell Line HaCaT Homo sapiens LDH = 247.0 MU PMID[450041]
NPT143 Individual Protein DNA topoisomerase I Homo sapiens MIC = 50000.0 nM PMID[450042]
NPT179 Cell Line A2780 Homo sapiens IC50 = 80.0 nM PMID[450046]
NPT1498 Individual Protein Dual specificity protein phosphatase 6 Rattus norvegicus IC50 = 6900.0 nM PMID[450046]
NPT1497 Individual Protein Dual specificity protein phosphatase 1 Mus musculus IC50 = 9370.0 nM PMID[450046]
NPT80 Cell Line Raji Homo sapiens Activity = 20.0 % PMID[450047]
NPT80 Cell Line Raji Homo sapiens Activity = 50.0 % PMID[450047]
NPT80 Cell Line Raji Homo sapiens Activity = 40.0 % PMID[450047]
NPT80 Cell Line Raji Homo sapiens Activity > 80.0 % PMID[450047]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 2754.23 nM PMID[450048]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 2612.16 nM PMID[450048]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 1327.39 nM PMID[450048]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 1210.6 nM PMID[450048]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 2108.63 nM PMID[450048]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 1690.44 nM PMID[450048]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 291.74 nM PMID[450048]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 14825.18 nM PMID[450048]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 2494.59 nM PMID[450048]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 1177.61 nM PMID[450048]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 2137.96 nM PMID[450048]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 424.62 nM PMID[450048]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 2964.83 nM PMID[450048]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 2094.11 nM PMID[450048]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 9749.9 nM PMID[450048]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 150.31 nM PMID[450048]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 1923.09 nM PMID[450048]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 5794.29 nM PMID[450048]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 909.91 nM PMID[450048]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 6950.24 nM PMID[450048]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 8413.95 nM PMID[450048]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 3169.57 nM PMID[450048]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 222.33 nM PMID[450048]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 2223.31 nM PMID[450048]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 490.91 nM PMID[450048]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 1264.74 nM PMID[450048]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 376.7 nM PMID[450048]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 504.66 nM PMID[450048]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 1577.61 nM PMID[450048]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 580.76 nM PMID[450048]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 5248.07 nM PMID[450048]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 8609.94 nM PMID[450048]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 435.51 nM PMID[450048]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 2393.32 nM PMID[450048]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 1559.55 nM PMID[450048]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 2041.74 nM PMID[450048]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 7638.36 nM PMID[450048]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 1836.54 nM PMID[450048]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 8953.65 nM PMID[450048]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 2089.3 nM PMID[450048]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 4655.86 nM PMID[450048]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 753.36 nM PMID[450048]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 899.5 nM PMID[450048]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 2517.68 nM PMID[450048]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 2754.23 nM PMID[450048]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 2322.74 nM PMID[450048]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 1803.02 nM PMID[450048]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 12823.31 nM PMID[450048]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 534.56 nM PMID[450048]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 12676.52 nM PMID[450048]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 2065.38 nM PMID[450048]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 1475.71 nM PMID[450048]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 2471.72 nM PMID[450048]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 1273.5 nM PMID[450048]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 3681.29 nM PMID[450048]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 7906.79 nM PMID[450048]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 7961.59 nM PMID[450048]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 1482.52 nM PMID[450048]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 2167.7 nM PMID[450048]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 1135.01 nM PMID[450048]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 2254.24 nM PMID[450048]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 154.53 nM PMID[450048]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 325.84 nM PMID[450048]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 1073.99 nM PMID[450048]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 9246.98 nM PMID[450048]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 2167.7 nM PMID[450048]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 1336.6 nM PMID[450048]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 1030.39 nM PMID[450048]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 807.24 nM PMID[450048]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 1156.11 nM PMID[450048]
NPT1217 Individual Protein Botulinum neurotoxin type A Clostridium botulinum Ratio = 2.2 /M/s PMID[450052]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 930.0 nM PMID[450053]
NPT116 Cell Line HL-60 Homo sapiens Activity = 0.0 % PMID[450053]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 800.0 nM PMID[450053]
NPT1603 Individual Protein Cytochrome P450 1A1 Homo sapiens Inhibition = 79.0 % PMID[450054]
NPT1604 Individual Protein Cytochrome P450 1B1 Homo sapiens Inhibition = 8.0 % PMID[450054]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens Inhibition = 82.0 % PMID[450054]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens Inhibition = 5.0 % PMID[450054]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Inhibition = 15.0 % PMID[450054]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens Inhibition = 5.0 % PMID[450054]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens Inhibition = 4.0 % PMID[450054]
NPT1603 Individual Protein Cytochrome P450 1A1 Homo sapiens Inhibition = 78.0 % PMID[450054]
NPT1603 Individual Protein Cytochrome P450 1A1 Homo sapiens IC50 = 3820.0 nM PMID[450054]
NPT1603 Individual Protein Cytochrome P450 1A1 Homo sapiens Ki = 3660.0 nM PMID[450054]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens IC50 = 2160.0 nM PMID[450054]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens Ki = 2220.0 nM PMID[450054]
NPT1604 Individual Protein Cytochrome P450 1B1 Homo sapiens IC50 > 10000.0 nM PMID[450054]
NPT110 Individual Protein Cytochrome P450 2D6 Homo sapiens IC50 > 10000.0 nM PMID[450054]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens IC50 > 10000.0 nM PMID[450054]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens IC50 > 10000.0 nM PMID[450054]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens IC50 > 10000.0 nM PMID[450054]
NPT35 Others n.a. LogP = 3.7 n.a. PMID[450041]
NPT610 Others Molecular identity unknown kDPPH = 41.5 M-1 s-1 PMID[450041]
NPT610 Others Molecular identity unknown Ratio = 0.33 n.a. PMID[450041]
NPT29 Organism Rattus norvegicus Rattus norvegicus Survivors = 3.0 ug ml-1 PMID[450043]
NPT29 Organism Rattus norvegicus Rattus norvegicus T/C = 37.0 % PMID[450043]
NPT29 Organism Rattus norvegicus Rattus norvegicus T/C = 37.0 % PMID[450044]
NPT3005 Protein Family Thioredoxin reductase Homo sapiens IC50 = 20000.0 nM PMID[450045]
NPT911 Individual Protein Dual specificity phosphatase Cdc25B Homo sapiens IC50 = 1000.0 nM PMID[450046]
NPT2 Others Unspecified Inhibition = 68.9 % PMID[450047]
NPT2 Others Unspecified Inhibition = 0.0 % PMID[450047]
NPT1365 Organism Trichoplusia ni Trichoplusia ni mortality = 20.0 % PMID[450049]
NPT1365 Organism Trichoplusia ni Trichoplusia ni DC50 = 10.1 microg/cm2 PMID[450049]
NPT1365 Organism Trichoplusia ni Trichoplusia ni FDI = 100.0 % PMID[450049]
NPT1499 Organism Erwinia amylovora Erwinia amylovora MIC = 10000.0 nM PMID[450050]
NPT35 Others n.a. LogD7.4 n.a. 1.91 n.a. PMID[450051]
NPT35 Others n.a. K = 0.025 /min PMID[450052]
NPT35 Others n.a. Activity = 39.0 % PMID[450052]
NPT35 Others n.a. Activity = 85.0 % PMID[450052]
NPT35 Others n.a. Activity = 26.0 % PMID[450052]

☑ 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 NPC232178 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
0.9554 High Similarity NPC108288
0.9328 High Similarity NPC306765
0.9224 High Similarity NPC206778
0.9224 High Similarity NPC285829
0.9167 High Similarity NPC1991
0.9167 High Similarity NPC96915
0.916 High Similarity NPC310540
0.9123 High Similarity NPC240163
0.9008 High Similarity NPC51037
0.8992 High Similarity NPC307174
0.8966 High Similarity NPC269414
0.8934 High Similarity NPC471530
0.8917 High Similarity NPC375356
0.8898 High Similarity NPC7151
0.8898 High Similarity NPC216297
0.8898 High Similarity NPC473662
0.888 High Similarity NPC242358
0.888 High Similarity NPC246693
0.888 High Similarity NPC110609
0.8862 High Similarity NPC237225
0.8852 High Similarity NPC231774
0.8852 High Similarity NPC3224
0.8833 High Similarity NPC300274
0.88 High Similarity NPC205992
0.879 High Similarity NPC278928
0.877 High Similarity NPC103540
0.876 High Similarity NPC477153
0.8718 High Similarity NPC477453
0.8718 High Similarity NPC312800
0.871 High Similarity NPC165257
0.8707 High Similarity NPC163154
0.8672 High Similarity NPC22222
0.8672 High Similarity NPC281513
0.864 High Similarity NPC34414
0.864 High Similarity NPC146647
0.8632 High Similarity NPC161304
0.8571 High Similarity NPC199253
0.8571 High Similarity NPC55949
0.8571 High Similarity NPC198305
0.8571 High Similarity NPC117609
0.8571 High Similarity NPC136588
0.8571 High Similarity NPC31539
0.856 High Similarity NPC282923
0.856 High Similarity NPC179898
0.8537 High Similarity NPC142956
0.8537 High Similarity NPC74507
0.8537 High Similarity NPC234890
0.8516 High Similarity NPC171968
0.8512 High Similarity NPC472046
0.8509 High Similarity NPC224584
0.8504 High Similarity NPC244699
0.8492 Intermediate Similarity NPC99731
0.8487 Intermediate Similarity NPC125252
0.848 Intermediate Similarity NPC45537
0.8462 Intermediate Similarity NPC155211
0.8462 Intermediate Similarity NPC474813
0.8462 Intermediate Similarity NPC272268
0.8443 Intermediate Similarity NPC198336
0.8438 Intermediate Similarity NPC70622
0.8421 Intermediate Similarity NPC34715
0.8417 Intermediate Similarity NPC41567
0.8413 Intermediate Similarity NPC48248
0.8413 Intermediate Similarity NPC247250
0.8413 Intermediate Similarity NPC767
0.8409 Intermediate Similarity NPC471602
0.8409 Intermediate Similarity NPC306835
0.8409 Intermediate Similarity NPC476477
0.8409 Intermediate Similarity NPC299405
0.8409 Intermediate Similarity NPC111422
0.8409 Intermediate Similarity NPC216312
0.8409 Intermediate Similarity NPC29771
0.8409 Intermediate Similarity NPC256463
0.84 Intermediate Similarity NPC136342
0.84 Intermediate Similarity NPC227741
0.84 Intermediate Similarity NPC49647
0.84 Intermediate Similarity NPC295202
0.8397 Intermediate Similarity NPC305060
0.8397 Intermediate Similarity NPC245923
0.8397 Intermediate Similarity NPC147418
0.8387 Intermediate Similarity NPC152525
0.8387 Intermediate Similarity NPC68756
0.8385 Intermediate Similarity NPC129752
0.8374 Intermediate Similarity NPC283514
0.8372 Intermediate Similarity NPC52407
0.8372 Intermediate Similarity NPC53896
0.8359 Intermediate Similarity NPC205360
0.8347 Intermediate Similarity NPC233165
0.8347 Intermediate Similarity NPC184579
0.8346 Intermediate Similarity NPC327916
0.8346 Intermediate Similarity NPC32749
0.8346 Intermediate Similarity NPC220496
0.8346 Intermediate Similarity NPC42262
0.8346 Intermediate Similarity NPC37992
0.8346 Intermediate Similarity NPC147542
0.8346 Intermediate Similarity NPC241349
0.8333 Intermediate Similarity NPC473787
0.832 Intermediate Similarity NPC131799
0.8308 Intermediate Similarity NPC288089
0.8308 Intermediate Similarity NPC50924
0.8295 Intermediate Similarity NPC309430
0.8295 Intermediate Similarity NPC58685
0.8295 Intermediate Similarity NPC88864
0.8295 Intermediate Similarity NPC477406
0.8284 Intermediate Similarity NPC257003
0.8284 Intermediate Similarity NPC471444
0.8281 Intermediate Similarity NPC31799
0.8281 Intermediate Similarity NPC475741
0.8268 Intermediate Similarity NPC95537
0.8261 Intermediate Similarity NPC141523
0.8244 Intermediate Similarity NPC283088
0.8244 Intermediate Similarity NPC161632
0.824 Intermediate Similarity NPC173978
0.8231 Intermediate Similarity NPC115458
0.8231 Intermediate Similarity NPC193169
0.8231 Intermediate Similarity NPC294226
0.8231 Intermediate Similarity NPC225051
0.8226 Intermediate Similarity NPC46634
0.8226 Intermediate Similarity NPC91478
0.8226 Intermediate Similarity NPC244351
0.8226 Intermediate Similarity NPC217756
0.8222 Intermediate Similarity NPC474300
0.822 Intermediate Similarity NPC231717
0.8217 Intermediate Similarity NPC17083
0.8217 Intermediate Similarity NPC141549
0.8217 Intermediate Similarity NPC85342
0.8211 Intermediate Similarity NPC272454
0.8211 Intermediate Similarity NPC301987
0.8211 Intermediate Similarity NPC292665
0.8211 Intermediate Similarity NPC35856
0.8211 Intermediate Similarity NPC115188
0.8211 Intermediate Similarity NPC26433
0.8211 Intermediate Similarity NPC159760
0.8211 Intermediate Similarity NPC244994
0.8211 Intermediate Similarity NPC178395
0.8211 Intermediate Similarity NPC222876
0.8211 Intermediate Similarity NPC179092
0.8195 Intermediate Similarity NPC173980
0.8189 Intermediate Similarity NPC470841
0.8182 Intermediate Similarity NPC193358
0.8174 Intermediate Similarity NPC187913
0.8168 Intermediate Similarity NPC44437
0.8162 Intermediate Similarity NPC476473
0.816 Intermediate Similarity NPC182646
0.816 Intermediate Similarity NPC135062
0.8154 Intermediate Similarity NPC17843
0.8148 Intermediate Similarity NPC124365
0.8145 Intermediate Similarity NPC120545
0.814 Intermediate Similarity NPC278787
0.814 Intermediate Similarity NPC147757
0.814 Intermediate Similarity NPC7569
0.8134 Intermediate Similarity NPC143438
0.813 Intermediate Similarity NPC260837
0.812 Intermediate Similarity NPC238108
0.811 Intermediate Similarity NPC160499
0.811 Intermediate Similarity NPC8745
0.8106 Intermediate Similarity NPC80035
0.8103 Intermediate Similarity NPC303264
0.8102 Intermediate Similarity NPC274085
0.8102 Intermediate Similarity NPC89664
0.8095 Intermediate Similarity NPC265910
0.8095 Intermediate Similarity NPC4012
0.8095 Intermediate Similarity NPC91475
0.8095 Intermediate Similarity NPC236189
0.8095 Intermediate Similarity NPC13238
0.8092 Intermediate Similarity NPC254603
0.808 Intermediate Similarity NPC282577
0.8065 Intermediate Similarity NPC165197
0.8065 Intermediate Similarity NPC190971
0.806 Intermediate Similarity NPC61590
0.8047 Intermediate Similarity NPC71525
0.8045 Intermediate Similarity NPC315275
0.8045 Intermediate Similarity NPC472308
0.8045 Intermediate Similarity NPC474311
0.8045 Intermediate Similarity NPC141934
0.8034 Intermediate Similarity NPC100551
0.8033 Intermediate Similarity NPC160199
0.8033 Intermediate Similarity NPC28169
0.8031 Intermediate Similarity NPC167055
0.8031 Intermediate Similarity NPC240744
0.8031 Intermediate Similarity NPC287473
0.8031 Intermediate Similarity NPC10926
0.803 Intermediate Similarity NPC282780
0.803 Intermediate Similarity NPC166480
0.8029 Intermediate Similarity NPC238629
0.8016 Intermediate Similarity NPC275145
0.8015 Intermediate Similarity NPC187843
0.8015 Intermediate Similarity NPC478190
0.8 Intermediate Similarity NPC103337
0.8 Intermediate Similarity NPC114620
0.8 Intermediate Similarity NPC25168
0.8 Intermediate Similarity NPC295339
0.8 Intermediate Similarity NPC477408
0.7985 Intermediate Similarity NPC53206
0.7985 Intermediate Similarity NPC53414
0.7983 Intermediate Similarity NPC228609
0.7971 Intermediate Similarity NPC477409
0.797 Intermediate Similarity NPC72918
0.797 Intermediate Similarity NPC258502
0.7969 Intermediate Similarity NPC15837
0.7969 Intermediate Similarity NPC472047

  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 NPC232178 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
0.9554 High Similarity NPD405 Clinical (unspecified phase)
0.877 High Similarity NPD1470 Approved
0.8443 Intermediate Similarity NPD1201 Approved
0.8034 Intermediate Similarity NPD74 Approved
0.8034 Intermediate Similarity NPD9266 Approved
0.7949 Intermediate Similarity NPD9267 Approved
0.7949 Intermediate Similarity NPD9263 Approved
0.7949 Intermediate Similarity NPD9264 Approved
0.791 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD943 Approved
0.7661 Intermediate Similarity NPD9493 Approved
0.7643 Intermediate Similarity NPD3300 Phase 2
0.7642 Intermediate Similarity NPD9281 Approved
0.7615 Intermediate Similarity NPD1164 Approved
0.7607 Intermediate Similarity NPD9261 Approved
0.7591 Intermediate Similarity NPD2935 Discontinued
0.7536 Intermediate Similarity NPD2346 Discontinued
0.7464 Intermediate Similarity NPD5405 Approved
0.7464 Intermediate Similarity NPD5406 Approved
0.7464 Intermediate Similarity NPD5404 Approved
0.7464 Intermediate Similarity NPD5408 Approved
0.7436 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD1203 Approved
0.7333 Intermediate Similarity NPD2313 Discontinued
0.7329 Intermediate Similarity NPD3226 Approved
0.7299 Intermediate Similarity NPD447 Suspended
0.7293 Intermediate Similarity NPD2798 Approved
0.7287 Intermediate Similarity NPD2932 Approved
0.7286 Intermediate Similarity NPD2344 Approved
0.7252 Intermediate Similarity NPD9717 Approved
0.7234 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7390 Discontinued
0.7209 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD411 Approved
0.7206 Intermediate Similarity NPD3764 Approved
0.7154 Intermediate Similarity NPD3019 Approved
0.7143 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1510 Phase 2
0.7143 Intermediate Similarity NPD2799 Discontinued
0.7133 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD9269 Phase 2
0.7101 Intermediate Similarity NPD1240 Approved
0.7083 Intermediate Similarity NPD2309 Approved
0.7077 Intermediate Similarity NPD9268 Approved
0.7063 Intermediate Similarity NPD7635 Approved
0.7055 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD288 Approved
0.7029 Intermediate Similarity NPD520 Approved
0.7014 Intermediate Similarity NPD3750 Approved
0.7 Intermediate Similarity NPD1607 Approved
0.6986 Remote Similarity NPD1511 Approved
0.6967 Remote Similarity NPD164 Approved
0.6967 Remote Similarity NPD1237 Approved
0.6957 Remote Similarity NPD9256 Approved
0.6957 Remote Similarity NPD9258 Approved
0.6949 Remote Similarity NPD844 Approved
0.6923 Remote Similarity NPD1471 Phase 3
0.6908 Remote Similarity NPD2801 Approved
0.6892 Remote Similarity NPD1512 Approved
0.6889 Remote Similarity NPD1876 Approved
0.688 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1549 Phase 2
0.687 Remote Similarity NPD9545 Approved
0.6853 Remote Similarity NPD1551 Phase 2
0.685 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6844 Discontinued
0.6828 Remote Similarity NPD2800 Approved
0.6815 Remote Similarity NPD1755 Approved
0.6809 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6806 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6806 Remote Similarity NPD1550 Clinical (unspecified phase)
0.68 Remote Similarity NPD2342 Discontinued
0.6753 Remote Similarity NPD5402 Approved
0.6746 Remote Similarity NPD2182 Approved
0.6744 Remote Similarity NPD1241 Discontinued
0.6741 Remote Similarity NPD1481 Phase 2
0.6741 Remote Similarity NPD4878 Approved
0.6739 Remote Similarity NPD9494 Approved
0.6716 Remote Similarity NPD3026 Approved
0.6716 Remote Similarity NPD3023 Approved
0.6711 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6711 Remote Similarity NPD2533 Approved
0.6711 Remote Similarity NPD2534 Approved
0.6711 Remote Similarity NPD2532 Approved
0.6709 Remote Similarity NPD6232 Discontinued
0.6693 Remote Similarity NPD4750 Phase 3
0.6692 Remote Similarity NPD3025 Approved
0.6692 Remote Similarity NPD497 Approved
0.6692 Remote Similarity NPD5951 Approved
0.6692 Remote Similarity NPD3024 Approved
0.6691 Remote Similarity NPD6832 Phase 2
0.669 Remote Similarity NPD230 Phase 1
0.669 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6688 Remote Similarity NPD7819 Suspended
0.6687 Remote Similarity NPD7473 Discontinued
0.6667 Remote Similarity NPD3748 Approved
0.6667 Remote Similarity NPD1019 Discontinued
0.6667 Remote Similarity NPD1932 Approved
0.6667 Remote Similarity NPD1535 Discovery
0.6667 Remote Similarity NPD3749 Approved
0.6642 Remote Similarity NPD1283 Approved
0.6641 Remote Similarity NPD6671 Approved
0.6639 Remote Similarity NPD1202 Approved
0.6639 Remote Similarity NPD845 Approved
0.6639 Remote Similarity NPD3020 Approved
0.6623 Remote Similarity NPD1934 Approved
0.6617 Remote Similarity NPD1759 Phase 1
0.6615 Remote Similarity NPD495 Approved
0.6615 Remote Similarity NPD496 Approved
0.6615 Remote Similarity NPD498 Approved
0.6613 Remote Similarity NPD1929 Approved
0.6613 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6613 Remote Similarity NPD1930 Approved
0.6609 Remote Similarity NPD9257 Approved
0.6609 Remote Similarity NPD9259 Approved
0.6603 Remote Similarity NPD3882 Suspended
0.6601 Remote Similarity NPD4380 Phase 2
0.6593 Remote Similarity NPD3496 Discontinued
0.6585 Remote Similarity NPD5031 Approved
0.6585 Remote Similarity NPD5029 Approved
0.6585 Remote Similarity NPD5027 Approved
0.6583 Remote Similarity NPD2933 Approved
0.6583 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6583 Remote Similarity NPD2934 Approved
0.6581 Remote Similarity NPD1465 Phase 2
0.6581 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6567 Remote Similarity NPD1651 Approved
0.6562 Remote Similarity NPD3022 Approved
0.6562 Remote Similarity NPD3021 Approved
0.6554 Remote Similarity NPD8166 Discontinued
0.6554 Remote Similarity NPD7003 Approved
0.6554 Remote Similarity NPD1196 Approved
0.6552 Remote Similarity NPD4308 Phase 3
0.6552 Remote Similarity NPD650 Approved
0.6545 Remote Similarity NPD36 Approved
0.6545 Remote Similarity NPD5034 Approved
0.6545 Remote Similarity NPD4955 Approved
0.6545 Remote Similarity NPD5026 Approved
0.6545 Remote Similarity NPD4954 Approved
0.6545 Remote Similarity NPD5028 Approved
0.6541 Remote Similarity NPD1758 Phase 1
0.6541 Remote Similarity NPD6959 Discontinued
0.6538 Remote Similarity NPD2296 Approved
0.6536 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6533 Remote Similarity NPD1543 Discontinued
0.6529 Remote Similarity NPD2860 Approved
0.6529 Remote Similarity NPD2859 Approved
0.6519 Remote Similarity NPD4626 Approved
0.6519 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6512 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6509 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6496 Remote Similarity NPD3972 Approved
0.6496 Remote Similarity NPD1608 Approved
0.649 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6488 Remote Similarity NPD8150 Discontinued
0.6486 Remote Similarity NPD1195 Approved
0.6485 Remote Similarity NPD5030 Phase 2
0.6483 Remote Similarity NPD9279 Approved
0.6479 Remote Similarity NPD3268 Approved
0.6475 Remote Similarity NPD2797 Approved
0.6452 Remote Similarity NPD1242 Phase 1
0.6449 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6443 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6442 Remote Similarity NPD3751 Discontinued
0.6434 Remote Similarity NPD6663 Approved
0.6434 Remote Similarity NPD1792 Phase 2
0.6433 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6429 Remote Similarity NPD2649 Approved
0.6429 Remote Similarity NPD2651 Approved
0.6423 Remote Similarity NPD1611 Approved
0.6423 Remote Similarity NPD1281 Approved
0.6414 Remote Similarity NPD6651 Approved
0.6407 Remote Similarity NPD8312 Approved
0.6407 Remote Similarity NPD8313 Approved
0.64 Remote Similarity NPD846 Approved
0.64 Remote Similarity NPD940 Approved
0.6397 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6395 Remote Similarity NPD2796 Approved
0.6393 Remote Similarity NPD1809 Phase 2
0.6391 Remote Similarity NPD5038 Approved
0.6391 Remote Similarity NPD5037 Approved
0.6391 Remote Similarity NPD256 Approved
0.6391 Remote Similarity NPD255 Approved
0.6385 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6383 Remote Similarity NPD5736 Approved
0.6379 Remote Similarity NPD111 Approved
0.6376 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6375 Remote Similarity NPD5494 Approved
0.6371 Remote Similarity NPD2066 Phase 3
0.637 Remote Similarity NPD2226 Clinical (unspecified phase)
0.6364 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6364 Remote Similarity NPD1398 Phase 1
0.6364 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6357 Remote Similarity NPD2329 Discontinued
0.6352 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6345 Remote Similarity NPD1933 Approved
0.6343 Remote Similarity NPD9568 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

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

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

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