Structure

Physi-Chem Properties

Molecular Weight:  368.13
Volume:  375.116
LogP:  4.661
LogD:  2.839
LogS:  -3.277
# Rotatable Bonds:  4
TPSA:  100.13
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.6
Synthetic Accessibility Score:  2.701
Fsp3:  0.19
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.802
MDCK Permeability:  1.2252437954884954e-05
Pgp-inhibitor:  0.184
Pgp-substrate:  0.024
Human Intestinal Absorption (HIA):  0.022
20% Bioavailability (F20%):  0.042
30% Bioavailability (F30%):  0.207

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.004
Plasma Protein Binding (PPB):  94.26415252685547%
Volume Distribution (VD):  0.635
Pgp-substrate:  6.884089946746826%

ADMET: Metabolism

CYP1A2-inhibitor:  0.855
CYP1A2-substrate:  0.462
CYP2C19-inhibitor:  0.894
CYP2C19-substrate:  0.06
CYP2C9-inhibitor:  0.868
CYP2C9-substrate:  0.921
CYP2D6-inhibitor:  0.762
CYP2D6-substrate:  0.314
CYP3A4-inhibitor:  0.332
CYP3A4-substrate:  0.108

ADMET: Excretion

Clearance (CL):  7.159
Half-life (T1/2):  0.742

ADMET: Toxicity

hERG Blockers:  0.012
Human Hepatotoxicity (H-HT):  0.309
Drug-inuced Liver Injury (DILI):  0.965
AMES Toxicity:  0.536
Rat Oral Acute Toxicity:  0.234
Maximum Recommended Daily Dose:  0.056
Skin Sensitization:  0.754
Carcinogencity:  0.119
Eye Corrosion:  0.003
Eye Irritation:  0.851
Respiratory Toxicity:  0.116

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General Info & Identifiers & Properties  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC306488

Natural Product ID:  NPC306488
Common Name*:   Topazolin
IUPAC Name:   5,7-dihydroxy-2-(4-hydroxyphenyl)-3-methoxy-6-(3-methylbut-2-enyl)chromen-4-one
Synonyms:  
Standard InCHIKey:  VVXGFIWLFZMBCJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H20O6/c1-11(2)4-9-14-15(23)10-16-17(18(14)24)19(25)21(26-3)20(27-16)12-5-7-13(22)8-6-12/h4-8,10,22-24H,9H2,1-3H3
SMILES:  COc1c(oc2c(c1=O)c(O)c(c(c2)O)CC=C(C)C)c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3810179
PubChem CID:   5481965
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001615] Flavones
          • [CHEMONTID:0003503] 6-prenylated flavones

*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
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[12713396]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[16441081]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16675659]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota roots n.a. n.a. PMID[20022509]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21866899]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22074222]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23325115]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Roots n.a. n.a. PMID[23541646]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. rhizome n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24479468]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24957203]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25445757]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25744461]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26841168]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28140583]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28522265]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[32196343]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[7381508]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22336 Glycyrrhiza aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22336 Glycyrrhiza aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22336 Glycyrrhiza aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7786 Lentinus tigrinus Species Lentinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10026 Mitracarpus scaber Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22336 Glycyrrhiza aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1698 Glycyrrhiza inflata Species Fabaceae 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
NPT65 Cell Line HepG2 Homo sapiens IC50 = 10800.0 nM PMID[523935]
NPT660 Cell Line SW480 Homo sapiens IC50 = 16100.0 nM PMID[523935]
NPT81 Cell Line A549 Homo sapiens IC50 = 23100.0 nM PMID[523935]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 7300.0 nM PMID[523935]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 52.0 % PMID[523935]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 4500.0 nM PMID[523936]

☑ 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 NPC306488 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC178343
1.0 High Similarity NPC5820
0.9928 High Similarity NPC216538
0.9928 High Similarity NPC273538
0.9857 High Similarity NPC124729
0.9856 High Similarity NPC9117
0.9856 High Similarity NPC158874
0.9856 High Similarity NPC24821
0.9856 High Similarity NPC212932
0.9856 High Similarity NPC293053
0.9856 High Similarity NPC190637
0.9789 High Similarity NPC470461
0.9786 High Similarity NPC326500
0.9784 High Similarity NPC473042
0.9784 High Similarity NPC200694
0.9718 High Similarity NPC296869
0.9718 High Similarity NPC244407
0.9718 High Similarity NPC470460
0.9716 High Similarity NPC470458
0.9712 High Similarity NPC90582
0.9712 High Similarity NPC262094
0.9648 High Similarity NPC166757
0.9648 High Similarity NPC14001
0.964 High Similarity NPC146679
0.964 High Similarity NPC230285
0.964 High Similarity NPC159275
0.964 High Similarity NPC184536
0.964 High Similarity NPC241100
0.964 High Similarity NPC103342
0.964 High Similarity NPC59951
0.964 High Similarity NPC103904
0.9583 High Similarity NPC61258
0.9577 High Similarity NPC220418
0.9571 High Similarity NPC110969
0.9571 High Similarity NPC282300
0.9571 High Similarity NPC136840
0.9568 High Similarity NPC55018
0.9568 High Similarity NPC301217
0.9568 High Similarity NPC220062
0.9568 High Similarity NPC303633
0.9568 High Similarity NPC216978
0.9568 High Similarity NPC143799
0.9568 High Similarity NPC18260
0.9568 High Similarity NPC78913
0.9568 High Similarity NPC217186
0.9568 High Similarity NPC53181
0.9568 High Similarity NPC96565
0.9568 High Similarity NPC241838
0.9568 High Similarity NPC152042
0.9521 High Similarity NPC311579
0.9521 High Similarity NPC236756
0.9514 High Similarity NPC269420
0.9507 High Similarity NPC224714
0.9507 High Similarity NPC311741
0.9507 High Similarity NPC234629
0.9504 High Similarity NPC226636
0.9504 High Similarity NPC11561
0.95 High Similarity NPC270883
0.95 High Similarity NPC269652
0.95 High Similarity NPC172986
0.95 High Similarity NPC261227
0.95 High Similarity NPC281207
0.95 High Similarity NPC150522
0.9496 High Similarity NPC276905
0.9496 High Similarity NPC201395
0.9456 High Similarity NPC133392
0.9444 High Similarity NPC168085
0.9441 High Similarity NPC472629
0.9437 High Similarity NPC166138
0.9437 High Similarity NPC106985
0.9437 High Similarity NPC18585
0.9437 High Similarity NPC11700
0.9437 High Similarity NPC470216
0.9437 High Similarity NPC219915
0.9433 High Similarity NPC118840
0.9433 High Similarity NPC103362
0.9433 High Similarity NPC156590
0.9433 High Similarity NPC205006
0.9433 High Similarity NPC147688
0.9433 High Similarity NPC469404
0.9433 High Similarity NPC64908
0.9388 High Similarity NPC193200
0.9384 High Similarity NPC262039
0.9384 High Similarity NPC254412
0.9384 High Similarity NPC262038
0.9384 High Similarity NPC319910
0.9384 High Similarity NPC278476
0.9379 High Similarity NPC5173
0.9379 High Similarity NPC317492
0.9375 High Similarity NPC237635
0.9375 High Similarity NPC296998
0.9375 High Similarity NPC473077
0.9375 High Similarity NPC308200
0.9375 High Similarity NPC79469
0.9375 High Similarity NPC259632
0.9375 High Similarity NPC201731
0.9375 High Similarity NPC97716
0.9375 High Similarity NPC24673
0.9375 High Similarity NPC104406
0.9371 High Similarity NPC319752
0.9371 High Similarity NPC87486
0.9371 High Similarity NPC124780
0.9371 High Similarity NPC470890
0.9371 High Similarity NPC271288
0.9366 High Similarity NPC161506
0.9366 High Similarity NPC227579
0.9366 High Similarity NPC324436
0.9366 High Similarity NPC62840
0.9366 High Similarity NPC78803
0.9366 High Similarity NPC32739
0.9366 High Similarity NPC10937
0.9366 High Similarity NPC328164
0.9366 High Similarity NPC66515
0.9366 High Similarity NPC194432
0.9366 High Similarity NPC306829
0.9366 High Similarity NPC144499
0.9366 High Similarity NPC148757
0.9366 High Similarity NPC125855
0.9366 High Similarity NPC296917
0.9366 High Similarity NPC228504
0.9366 High Similarity NPC76338
0.9366 High Similarity NPC324134
0.9366 High Similarity NPC293852
0.9366 High Similarity NPC166934
0.9366 High Similarity NPC182852
0.9366 High Similarity NPC220998
0.9366 High Similarity NPC214236
0.9366 High Similarity NPC37496
0.9366 High Similarity NPC167624
0.9366 High Similarity NPC107572
0.9366 High Similarity NPC40833
0.9366 High Similarity NPC299080
0.9366 High Similarity NPC64915
0.9366 High Similarity NPC223500
0.9366 High Similarity NPC265040
0.9366 High Similarity NPC59739
0.9366 High Similarity NPC1089
0.9366 High Similarity NPC78
0.9366 High Similarity NPC166482
0.9366 High Similarity NPC177354
0.9366 High Similarity NPC217083
0.9366 High Similarity NPC76372
0.9362 High Similarity NPC326109
0.9362 High Similarity NPC69769
0.9362 High Similarity NPC475680
0.9362 High Similarity NPC213659
0.9362 High Similarity NPC48624
0.9362 High Similarity NPC235239
0.9362 High Similarity NPC305355
0.9362 High Similarity NPC204985
0.9362 High Similarity NPC80962
0.9362 High Similarity NPC215311
0.9362 High Similarity NPC172250
0.9362 High Similarity NPC144118
0.9362 High Similarity NPC259166
0.9362 High Similarity NPC219917
0.9357 High Similarity NPC131130
0.9353 High Similarity NPC174999
0.9353 High Similarity NPC194281
0.9353 High Similarity NPC473887
0.9353 High Similarity NPC127447
0.9353 High Similarity NPC61546
0.9353 High Similarity NPC231772
0.9353 High Similarity NPC281917
0.9353 High Similarity NPC124784
0.9353 High Similarity NPC13408
0.9353 High Similarity NPC234133
0.9353 High Similarity NPC187432
0.9353 High Similarity NPC29353
0.9353 High Similarity NPC256042
0.9353 High Similarity NPC72452
0.9353 High Similarity NPC116775
0.9353 High Similarity NPC47815
0.9353 High Similarity NPC216361
0.9324 High Similarity NPC111341
0.9324 High Similarity NPC207809
0.9324 High Similarity NPC476169
0.9324 High Similarity NPC304207
0.9324 High Similarity NPC304745
0.9324 High Similarity NPC259710
0.9324 High Similarity NPC217706
0.9324 High Similarity NPC48579
0.932 High Similarity NPC45934
0.932 High Similarity NPC35567
0.932 High Similarity NPC63187
0.932 High Similarity NPC142527
0.932 High Similarity NPC171651
0.932 High Similarity NPC138288
0.932 High Similarity NPC157784
0.932 High Similarity NPC243171
0.932 High Similarity NPC37684
0.932 High Similarity NPC210597
0.932 High Similarity NPC217149
0.932 High Similarity NPC216035
0.9315 High Similarity NPC476185
0.9315 High Similarity NPC471115
0.9315 High Similarity NPC105136
0.9315 High Similarity NPC472633
0.9315 High Similarity NPC321896
0.9315 High Similarity NPC29777

  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 NPC306488 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
0.9928 High Similarity NPD4378 Clinical (unspecified phase)
0.9103 High Similarity NPD7410 Clinical (unspecified phase)
0.9073 High Similarity NPD7075 Discontinued
0.9014 High Similarity NPD1550 Clinical (unspecified phase)
0.9014 High Similarity NPD1552 Clinical (unspecified phase)
0.9007 High Similarity NPD1510 Phase 2
0.9 High Similarity NPD2393 Clinical (unspecified phase)
0.9 High Similarity NPD7096 Clinical (unspecified phase)
0.8951 High Similarity NPD1549 Phase 2
0.8944 High Similarity NPD2796 Approved
0.8933 High Similarity NPD6801 Discontinued
0.8926 High Similarity NPD4380 Phase 2
0.8912 High Similarity NPD1512 Approved
0.8857 High Similarity NPD1240 Approved
0.8816 High Similarity NPD8443 Clinical (unspecified phase)
0.8797 High Similarity NPD7804 Clinical (unspecified phase)
0.8776 High Similarity NPD6799 Approved
0.8776 High Similarity NPD1511 Approved
0.875 High Similarity NPD2801 Approved
0.8742 High Similarity NPD7411 Suspended
0.8732 High Similarity NPD1607 Approved
0.8693 High Similarity NPD3817 Phase 2
0.8684 High Similarity NPD1934 Approved
0.8636 High Similarity NPD3882 Suspended
0.8627 High Similarity NPD7819 Suspended
0.8581 High Similarity NPD4381 Clinical (unspecified phase)
0.8553 High Similarity NPD6599 Discontinued
0.8503 High Similarity NPD2800 Approved
0.8491 Intermediate Similarity NPD6166 Phase 2
0.8491 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8491 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8446 Intermediate Similarity NPD3750 Approved
0.8418 Intermediate Similarity NPD6959 Discontinued
0.8397 Intermediate Similarity NPD7768 Phase 2
0.8378 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8375 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8355 Intermediate Similarity NPD5403 Approved
0.8344 Intermediate Similarity NPD6797 Phase 2
0.8311 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8299 Intermediate Similarity NPD2935 Discontinued
0.8293 Intermediate Similarity NPD7251 Discontinued
0.8255 Intermediate Similarity NPD1243 Approved
0.8242 Intermediate Similarity NPD7808 Phase 3
0.8235 Intermediate Similarity NPD920 Approved
0.8224 Intermediate Similarity NPD5401 Approved
0.8219 Intermediate Similarity NPD6651 Approved
0.8217 Intermediate Similarity NPD5402 Approved
0.8194 Intermediate Similarity NPD2313 Discontinued
0.8194 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD1551 Phase 2
0.816 Intermediate Similarity NPD3818 Discontinued
0.8137 Intermediate Similarity NPD6232 Discontinued
0.8133 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.8133 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD5494 Approved
0.8113 Intermediate Similarity NPD3749 Approved
0.811 Intermediate Similarity NPD7054 Approved
0.8108 Intermediate Similarity NPD2799 Discontinued
0.8108 Intermediate Similarity NPD3748 Approved
0.8105 Intermediate Similarity NPD2533 Approved
0.8105 Intermediate Similarity NPD2532 Approved
0.8105 Intermediate Similarity NPD2534 Approved
0.8105 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8098 Intermediate Similarity NPD7473 Discontinued
0.8092 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8075 Intermediate Similarity NPD1247 Approved
0.8063 Intermediate Similarity NPD919 Approved
0.8061 Intermediate Similarity NPD7074 Phase 3
0.8061 Intermediate Similarity NPD7472 Approved
0.8012 Intermediate Similarity NPD5953 Discontinued
0.8 Intermediate Similarity NPD7286 Phase 2
0.8 Intermediate Similarity NPD2344 Approved
0.7964 Intermediate Similarity NPD6559 Discontinued
0.7961 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7945 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7937 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD3226 Approved
0.7867 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7847 Intermediate Similarity NPD1203 Approved
0.7823 Intermediate Similarity NPD3268 Approved
0.7815 Intermediate Similarity NPD6100 Approved
0.7815 Intermediate Similarity NPD6099 Approved
0.7808 Intermediate Similarity NPD4908 Phase 1
0.7806 Intermediate Similarity NPD7390 Discontinued
0.7793 Intermediate Similarity NPD2798 Approved
0.7792 Intermediate Similarity NPD2309 Approved
0.7786 Intermediate Similarity NPD1548 Phase 1
0.7784 Intermediate Similarity NPD5844 Phase 1
0.7784 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD4360 Phase 2
0.7771 Intermediate Similarity NPD4363 Phase 3
0.7763 Intermediate Similarity NPD2346 Discontinued
0.7758 Intermediate Similarity NPD3926 Phase 2
0.7748 Intermediate Similarity NPD7033 Discontinued
0.7727 Intermediate Similarity NPD4628 Phase 3
0.7724 Intermediate Similarity NPD2797 Approved
0.7718 Intermediate Similarity NPD943 Approved
0.7692 Intermediate Similarity NPD422 Phase 1
0.7692 Intermediate Similarity NPD1610 Phase 2
0.7692 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7687 Intermediate Similarity NPD6832 Phase 2
0.7639 Intermediate Similarity NPD9717 Approved
0.7632 Intermediate Similarity NPD4308 Phase 3
0.7627 Intermediate Similarity NPD4361 Phase 2
0.7627 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD6798 Discontinued
0.7578 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD5124 Phase 1
0.755 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD2654 Approved
0.7534 Intermediate Similarity NPD3225 Approved
0.7532 Intermediate Similarity NPD1471 Phase 3
0.7517 Intermediate Similarity NPD4625 Phase 3
0.75 Intermediate Similarity NPD2403 Approved
0.7485 Intermediate Similarity NPD5711 Approved
0.7485 Intermediate Similarity NPD1465 Phase 2
0.7485 Intermediate Similarity NPD5710 Approved
0.7483 Intermediate Similarity NPD3266 Approved
0.7483 Intermediate Similarity NPD3267 Approved
0.745 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD4288 Approved
0.7438 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD6355 Discontinued
0.7427 Intermediate Similarity NPD1729 Discontinued
0.7417 Intermediate Similarity NPD6233 Phase 2
0.7412 Intermediate Similarity NPD3751 Discontinued
0.7403 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD1608 Approved
0.7397 Intermediate Similarity NPD3972 Approved
0.7396 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD7229 Phase 3
0.7381 Intermediate Similarity NPD3787 Discontinued
0.7375 Intermediate Similarity NPD5049 Phase 3
0.7368 Intermediate Similarity NPD1613 Approved
0.7368 Intermediate Similarity NPD4307 Phase 2
0.7368 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD4060 Phase 1
0.7351 Intermediate Similarity NPD1296 Phase 2
0.7346 Intermediate Similarity NPD7458 Discontinued
0.7342 Intermediate Similarity NPD2354 Approved
0.7337 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD1201 Approved
0.732 Intermediate Similarity NPD230 Phase 1
0.732 Intermediate Similarity NPD447 Suspended
0.732 Intermediate Similarity NPD1933 Approved
0.7312 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD7584 Approved
0.7308 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD9545 Approved
0.7278 Intermediate Similarity NPD7003 Approved
0.7273 Intermediate Similarity NPD9493 Approved
0.7268 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD5890 Approved
0.7256 Intermediate Similarity NPD5889 Approved
0.725 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD1164 Approved
0.7248 Intermediate Similarity NPD1470 Approved
0.7244 Intermediate Similarity NPD5404 Approved
0.7244 Intermediate Similarity NPD5406 Approved
0.7244 Intermediate Similarity NPD5408 Approved
0.7244 Intermediate Similarity NPD5405 Approved
0.7239 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD411 Approved
0.7237 Intermediate Similarity NPD3764 Approved
0.7233 Intermediate Similarity NPD3887 Approved
0.7232 Intermediate Similarity NPD8434 Phase 2
0.723 Intermediate Similarity NPD4749 Approved
0.7229 Intermediate Similarity NPD2296 Approved
0.7212 Intermediate Similarity NPD6844 Discontinued
0.72 Intermediate Similarity NPD1019 Discontinued
0.7197 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD2353 Approved
0.7195 Intermediate Similarity NPD6585 Discontinued
0.7192 Intermediate Similarity NPD17 Approved
0.7183 Intermediate Similarity NPD1241 Discontinued
0.7174 Intermediate Similarity NPD6782 Approved
0.7174 Intermediate Similarity NPD6777 Approved
0.7174 Intermediate Similarity NPD6778 Approved
0.7174 Intermediate Similarity NPD6781 Approved
0.7174 Intermediate Similarity NPD6780 Approved
0.7174 Intermediate Similarity NPD6779 Approved
0.7174 Intermediate Similarity NPD6776 Approved
0.7171 Intermediate Similarity NPD3027 Phase 3
0.7162 Intermediate Similarity NPD1481 Phase 2
0.7159 Intermediate Similarity NPD8313 Approved
0.7159 Intermediate Similarity NPD8312 Approved
0.7152 Intermediate Similarity NPD2424 Discontinued
0.7152 Intermediate Similarity NPD2861 Phase 2
0.7151 Intermediate Similarity NPD4287 Approved
0.7151 Intermediate Similarity NPD7435 Discontinued
0.7143 Intermediate Similarity NPD6104 Discontinued
0.7134 Intermediate Similarity NPD4476 Approved
0.7134 Intermediate Similarity NPD4477 Approved
0.7125 Intermediate Similarity NPD6190 Approved
0.7124 Intermediate Similarity NPD6410 Clinical (unspecified phase)

  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