Structure

Physi-Chem Properties

Molecular Weight:  368.13
Volume:  375.116
LogP:  4.101
LogD:  2.815
LogS:  -3.457
# 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:  0.474
Synthetic Accessibility Score:  2.843
Fsp3:  0.19
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.855
MDCK Permeability:  1.0444382496643811e-05
Pgp-inhibitor:  0.027
Pgp-substrate:  0.824
Human Intestinal Absorption (HIA):  0.018
20% Bioavailability (F20%):  0.959
30% Bioavailability (F30%):  0.62

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.008
Plasma Protein Binding (PPB):  92.1944808959961%
Volume Distribution (VD):  0.718
Pgp-substrate:  6.801499366760254%

ADMET: Metabolism

CYP1A2-inhibitor:  0.906
CYP1A2-substrate:  0.592
CYP2C19-inhibitor:  0.808
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.836
CYP2C9-substrate:  0.846
CYP2D6-inhibitor:  0.898
CYP2D6-substrate:  0.494
CYP3A4-inhibitor:  0.47
CYP3A4-substrate:  0.096

ADMET: Excretion

Clearance (CL):  8.801
Half-life (T1/2):  0.883

ADMET: Toxicity

hERG Blockers:  0.03
Human Hepatotoxicity (H-HT):  0.303
Drug-inuced Liver Injury (DILI):  0.387
AMES Toxicity:  0.037
Rat Oral Acute Toxicity:  0.229
Maximum Recommended Daily Dose:  0.72
Skin Sensitization:  0.944
Carcinogencity:  0.059
Eye Corrosion:  0.005
Eye Irritation:  0.908
Respiratory Toxicity:  0.163

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

  Natural Product: NPC166036

Natural Product ID:  NPC166036
Common Name*:   Glisoflavone
IUPAC Name:   3-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-7-hydroxy-5-methoxychromen-4-one
Synonyms:   Glisoflavone
Standard InCHIKey:  PYVPKOSKOWDDSV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H20O6/c1-11(2)4-5-12-6-13(7-16(23)20(12)24)15-10-27-18-9-14(22)8-17(26-3)19(18)21(15)25/h4,6-10,22-24H,5H2,1-3H3
SMILES:  COc1cc(O)cc2c1c(=O)c(co2)c1cc(O)c(c(c1)CC=C(C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1223641
PubChem CID:   5487298
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0002901] Isoflav-2-enes
          • [CHEMONTID:0000494] Isoflavones

*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. n.a. n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root 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. rhizome n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root 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]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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]
NPO1698 Glycyrrhiza inflata 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]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
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]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7154 Glycyrrhiza uralensis 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]
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
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 27900.0 nM PMID[551665]
NPT1211 Individual Protein Dual specificity protein phosphatase 3 Homo sapiens Inhibition > 70.0 % PMID[551666]
NPT1210 Individual Protein T-cell protein-tyrosine phosphatase Homo sapiens Inhibition = 4.0 % PMID[551666]

☑ 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 NPC166036 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 NPC203077
1.0 High Similarity NPC238279
0.993 High Similarity NPC171916
0.993 High Similarity NPC38545
0.9792 High Similarity NPC256406
0.9724 High Similarity NPC323626
0.9724 High Similarity NPC324233
0.9658 High Similarity NPC93552
0.9592 High Similarity NPC134287
0.9592 High Similarity NPC130589
0.9586 High Similarity NPC85131
0.9583 High Similarity NPC80710
0.9583 High Similarity NPC139364
0.9583 High Similarity NPC254702
0.9583 High Similarity NPC203747
0.9583 High Similarity NPC194653
0.9577 High Similarity NPC242893
0.9577 High Similarity NPC38065
0.9527 High Similarity NPC170026
0.9527 High Similarity NPC282307
0.9521 High Similarity NPC154345
0.9517 High Similarity NPC142876
0.9517 High Similarity NPC333691
0.9517 High Similarity NPC69430
0.9517 High Similarity NPC200060
0.9517 High Similarity NPC139293
0.9517 High Similarity NPC264550
0.9517 High Similarity NPC264289
0.9517 High Similarity NPC40290
0.9517 High Similarity NPC195763
0.9507 High Similarity NPC471417
0.9463 High Similarity NPC52889
0.9463 High Similarity NPC78103
0.9459 High Similarity NPC234255
0.9459 High Similarity NPC39184
0.9456 High Similarity NPC471982
0.9456 High Similarity NPC106976
0.9452 High Similarity NPC88804
0.9452 High Similarity NPC472279
0.9452 High Similarity NPC10467
0.9452 High Similarity NPC3825
0.9444 High Similarity NPC12377
0.9441 High Similarity NPC105213
0.9437 High Similarity NPC284556
0.9437 High Similarity NPC301178
0.94 High Similarity NPC184755
0.94 High Similarity NPC74178
0.9396 High Similarity NPC472455
0.9392 High Similarity NPC213896
0.9392 High Similarity NPC192083
0.9392 High Similarity NPC298692
0.9392 High Similarity NPC74924
0.9392 High Similarity NPC250557
0.9392 High Similarity NPC124714
0.9388 High Similarity NPC205046
0.9388 High Similarity NPC304295
0.9388 High Similarity NPC45291
0.9388 High Similarity NPC19980
0.9388 High Similarity NPC59162
0.9379 High Similarity NPC188074
0.9379 High Similarity NPC125449
0.9375 High Similarity NPC157133
0.9371 High Similarity NPC476054
0.9371 High Similarity NPC287722
0.9366 High Similarity NPC213659
0.9366 High Similarity NPC204985
0.9366 High Similarity NPC326109
0.9366 High Similarity NPC215311
0.9366 High Similarity NPC48624
0.9366 High Similarity NPC172250
0.9366 High Similarity NPC253822
0.9366 High Similarity NPC144118
0.9366 High Similarity NPC80962
0.9366 High Similarity NPC259166
0.9366 High Similarity NPC219917
0.9338 High Similarity NPC328102
0.9338 High Similarity NPC28241
0.9333 High Similarity NPC291508
0.9329 High Similarity NPC472280
0.9329 High Similarity NPC321779
0.9329 High Similarity NPC152951
0.9329 High Similarity NPC57674
0.9329 High Similarity NPC230149
0.9329 High Similarity NPC168247
0.9329 High Similarity NPC113906
0.9329 High Similarity NPC477503
0.9329 High Similarity NPC133392
0.9329 High Similarity NPC470327
0.9329 High Similarity NPC117992
0.9329 High Similarity NPC45849
0.9329 High Similarity NPC200761
0.9324 High Similarity NPC181209
0.9324 High Similarity NPC35763
0.9324 High Similarity NPC100971
0.9324 High Similarity NPC291802
0.9324 High Similarity NPC269451
0.9324 High Similarity NPC157784
0.9324 High Similarity NPC100263
0.9324 High Similarity NPC121522
0.9324 High Similarity NPC216769
0.9324 High Similarity NPC249570
0.9324 High Similarity NPC131266
0.9324 High Similarity NPC209487
0.9324 High Similarity NPC245382
0.9324 High Similarity NPC63187
0.9324 High Similarity NPC37684
0.9324 High Similarity NPC237994
0.932 High Similarity NPC239363
0.9315 High Similarity NPC218490
0.9301 High Similarity NPC268204
0.9301 High Similarity NPC52789
0.9301 High Similarity NPC26051
0.9301 High Similarity NPC469404
0.9301 High Similarity NPC55832
0.9296 High Similarity NPC295384
0.9296 High Similarity NPC283429
0.9272 High Similarity NPC469658
0.9272 High Similarity NPC204879
0.9267 High Similarity NPC278778
0.9267 High Similarity NPC195796
0.9267 High Similarity NPC209614
0.9267 High Similarity NPC35038
0.9267 High Similarity NPC472626
0.9267 High Similarity NPC470328
0.9267 High Similarity NPC291878
0.9262 High Similarity NPC273462
0.9262 High Similarity NPC476631
0.9262 High Similarity NPC227337
0.9262 High Similarity NPC170492
0.9262 High Similarity NPC107109
0.9262 High Similarity NPC70433
0.9262 High Similarity NPC49402
0.9262 High Similarity NPC33051
0.9257 High Similarity NPC262623
0.9252 High Similarity NPC105512
0.9252 High Similarity NPC48479
0.9252 High Similarity NPC177298
0.9247 High Similarity NPC95864
0.9247 High Similarity NPC222298
0.9247 High Similarity NPC108406
0.9247 High Similarity NPC51070
0.9236 High Similarity NPC119663
0.9236 High Similarity NPC254659
0.9231 High Similarity NPC101366
0.922 High Similarity NPC193792
0.9216 High Similarity NPC81679
0.9211 High Similarity NPC119209
0.9211 High Similarity NPC476283
0.9211 High Similarity NPC192686
0.9211 High Similarity NPC118256
0.9211 High Similarity NPC476980
0.9205 High Similarity NPC199463
0.9205 High Similarity NPC222689
0.9205 High Similarity NPC37543
0.9205 High Similarity NPC474055
0.9205 High Similarity NPC218313
0.9205 High Similarity NPC474681
0.9205 High Similarity NPC472598
0.9205 High Similarity NPC471209
0.9205 High Similarity NPC262286
0.9205 High Similarity NPC223787
0.9205 High Similarity NPC36852
0.9205 High Similarity NPC35598
0.9205 High Similarity NPC27337
0.92 High Similarity NPC256925
0.9195 High Similarity NPC472912
0.9195 High Similarity NPC60972
0.9195 High Similarity NPC257648
0.9195 High Similarity NPC39732
0.9195 High Similarity NPC477231
0.9195 High Similarity NPC474993
0.9189 High Similarity NPC156953
0.9184 High Similarity NPC3036
0.9184 High Similarity NPC119059
0.9184 High Similarity NPC120464
0.9172 High Similarity NPC475705
0.9172 High Similarity NPC476178
0.9172 High Similarity NPC51887
0.9172 High Similarity NPC207732
0.9172 High Similarity NPC142165
0.9172 High Similarity NPC117836
0.9167 High Similarity NPC185607
0.9155 High Similarity NPC212767
0.9155 High Similarity NPC162680
0.9155 High Similarity NPC209560
0.9155 High Similarity NPC294409
0.9155 High Similarity NPC303644
0.9155 High Similarity NPC181124
0.9155 High Similarity NPC7013
0.9155 High Similarity NPC116632
0.915 High Similarity NPC198829
0.915 High Similarity NPC474038
0.915 High Similarity NPC134783
0.915 High Similarity NPC26326
0.915 High Similarity NPC187354
0.915 High Similarity NPC258331
0.9145 High Similarity NPC85121
0.9145 High Similarity NPC210459
0.9145 High Similarity NPC22192
0.9145 High Similarity NPC53545

  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 NPC166036 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
0.9392 High Similarity NPD2393 Clinical (unspecified phase)
0.9067 High Similarity NPD1934 Approved
0.9041 High Similarity NPD1511 Approved
0.9014 High Similarity NPD1510 Phase 2
0.9007 High Similarity NPD2801 Approved
0.8933 High Similarity NPD4380 Phase 2
0.8919 High Similarity NPD1512 Approved
0.8889 High Similarity NPD3882 Suspended
0.8851 High Similarity NPD4378 Clinical (unspecified phase)
0.8732 High Similarity NPD1240 Approved
0.8625 High Similarity NPD3818 Discontinued
0.8616 High Similarity NPD6167 Clinical (unspecified phase)
0.8616 High Similarity NPD6168 Clinical (unspecified phase)
0.8616 High Similarity NPD6166 Phase 2
0.8611 High Similarity NPD1607 Approved
0.8601 High Similarity NPD943 Approved
0.86 High Similarity NPD7410 Clinical (unspecified phase)
0.859 High Similarity NPD7075 Discontinued
0.8581 High Similarity NPD3817 Phase 2
0.8571 High Similarity NPD1549 Phase 2
0.8562 High Similarity NPD2796 Approved
0.8526 High Similarity NPD4868 Clinical (unspecified phase)
0.8516 High Similarity NPD7096 Clinical (unspecified phase)
0.8516 High Similarity NPD7819 Suspended
0.8503 High Similarity NPD1552 Clinical (unspecified phase)
0.8503 High Similarity NPD1550 Clinical (unspecified phase)
0.8491 Intermediate Similarity NPD6232 Discontinued
0.8457 Intermediate Similarity NPD7054 Approved
0.8452 Intermediate Similarity NPD6801 Discontinued
0.8447 Intermediate Similarity NPD7473 Discontinued
0.8405 Intermediate Similarity NPD7472 Approved
0.8405 Intermediate Similarity NPD7074 Phase 3
0.8387 Intermediate Similarity NPD7411 Suspended
0.8365 Intermediate Similarity NPD5494 Approved
0.8354 Intermediate Similarity NPD6797 Phase 2
0.8354 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8311 Intermediate Similarity NPD2935 Discontinued
0.8303 Intermediate Similarity NPD7251 Discontinued
0.8289 Intermediate Similarity NPD6799 Approved
0.8199 Intermediate Similarity NPD6959 Discontinued
0.8163 Intermediate Similarity NPD230 Phase 1
0.8144 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8144 Intermediate Similarity NPD7808 Phase 3
0.8121 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8117 Intermediate Similarity NPD2532 Approved
0.8117 Intermediate Similarity NPD2534 Approved
0.8117 Intermediate Similarity NPD2533 Approved
0.8108 Intermediate Similarity NPD6651 Approved
0.8089 Intermediate Similarity NPD6599 Discontinued
0.8075 Intermediate Similarity NPD919 Approved
0.8063 Intermediate Similarity NPD7768 Phase 2
0.8049 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8026 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8024 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD5844 Phase 1
0.7976 Intermediate Similarity NPD6559 Discontinued
0.7975 Intermediate Similarity NPD1247 Approved
0.7974 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7974 Intermediate Similarity NPD3750 Approved
0.7937 Intermediate Similarity NPD1465 Phase 2
0.7908 Intermediate Similarity NPD2800 Approved
0.7908 Intermediate Similarity NPD1243 Approved
0.7898 Intermediate Similarity NPD5403 Approved
0.7891 Intermediate Similarity NPD3027 Phase 3
0.7888 Intermediate Similarity NPD5402 Approved
0.7881 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD1551 Phase 2
0.7821 Intermediate Similarity NPD7390 Discontinued
0.7785 Intermediate Similarity NPD920 Approved
0.7771 Intermediate Similarity NPD5401 Approved
0.7771 Intermediate Similarity NPD3926 Phase 2
0.7756 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7755 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7755 Intermediate Similarity NPD9494 Approved
0.7733 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD1613 Approved
0.7724 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD5953 Discontinued
0.7703 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7687 Intermediate Similarity NPD2798 Approved
0.7683 Intermediate Similarity NPD3749 Approved
0.7658 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD2799 Discontinued
0.7647 Intermediate Similarity NPD3748 Approved
0.7636 Intermediate Similarity NPD6234 Discontinued
0.7628 Intermediate Similarity NPD4628 Phase 3
0.76 Intermediate Similarity NPD2313 Discontinued
0.7597 Intermediate Similarity NPD6100 Approved
0.7597 Intermediate Similarity NPD6099 Approved
0.7595 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD7286 Phase 2
0.7578 Intermediate Similarity NPD3226 Approved
0.7569 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD2344 Approved
0.7546 Intermediate Similarity NPD37 Approved
0.7534 Intermediate Similarity NPD9269 Phase 2
0.7516 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5710 Approved
0.75 Intermediate Similarity NPD5711 Approved
0.7483 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7472 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD7458 Discontinued
0.7468 Intermediate Similarity NPD6190 Approved
0.7452 Intermediate Similarity NPD2654 Approved
0.7451 Intermediate Similarity NPD447 Suspended
0.744 Intermediate Similarity NPD7199 Phase 2
0.7436 Intermediate Similarity NPD2346 Discontinued
0.741 Intermediate Similarity NPD4965 Approved
0.741 Intermediate Similarity NPD4967 Phase 2
0.741 Intermediate Similarity NPD4966 Approved
0.7403 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD1203 Approved
0.7383 Intermediate Similarity NPD1470 Approved
0.7372 Intermediate Similarity NPD5406 Approved
0.7372 Intermediate Similarity NPD5405 Approved
0.7372 Intermediate Similarity NPD5408 Approved
0.7372 Intermediate Similarity NPD5404 Approved
0.7358 Intermediate Similarity NPD2309 Approved
0.7353 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD6832 Phase 2
0.7351 Intermediate Similarity NPD4908 Phase 1
0.7347 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD1201 Approved
0.7338 Intermediate Similarity NPD1933 Approved
0.7326 Intermediate Similarity NPD7228 Approved
0.731 Intermediate Similarity NPD1548 Phase 1
0.7308 Intermediate Similarity NPD7033 Discontinued
0.7301 Intermediate Similarity NPD1653 Approved
0.7297 Intermediate Similarity NPD3972 Approved
0.7293 Intermediate Similarity NPD4363 Phase 3
0.7293 Intermediate Similarity NPD4360 Phase 2
0.726 Intermediate Similarity NPD9268 Approved
0.7257 Intermediate Similarity NPD7685 Pre-registration
0.7255 Intermediate Similarity NPD3268 Approved
0.7253 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD4361 Phase 2
0.7251 Intermediate Similarity NPD5242 Approved
0.7249 Intermediate Similarity NPD8151 Discontinued
0.7241 Intermediate Similarity NPD5536 Phase 2
0.723 Intermediate Similarity NPD1610 Phase 2
0.7226 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD3751 Discontinued
0.7197 Intermediate Similarity NPD4308 Phase 3
0.7192 Intermediate Similarity NPD9545 Approved
0.719 Intermediate Similarity NPD4625 Phase 3
0.7189 Intermediate Similarity NPD6777 Approved
0.7189 Intermediate Similarity NPD6781 Approved
0.7189 Intermediate Similarity NPD6778 Approved
0.7189 Intermediate Similarity NPD6782 Approved
0.7189 Intermediate Similarity NPD6776 Approved
0.7189 Intermediate Similarity NPD6780 Approved
0.7189 Intermediate Similarity NPD6779 Approved
0.7188 Intermediate Similarity NPD8166 Discontinued
0.7188 Intermediate Similarity NPD7003 Approved
0.7181 Intermediate Similarity NPD9717 Approved
0.7175 Intermediate Similarity NPD8312 Approved
0.7175 Intermediate Similarity NPD8313 Approved
0.7172 Intermediate Similarity NPD9493 Approved
0.7171 Intermediate Similarity NPD3018 Phase 2
0.716 Intermediate Similarity NPD4357 Discontinued
0.7152 Intermediate Similarity NPD2797 Approved
0.7152 Intermediate Similarity NPD1164 Approved
0.7152 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD8150 Discontinued
0.7143 Intermediate Similarity NPD1729 Discontinued
0.7143 Intermediate Similarity NPD5353 Approved
0.7143 Intermediate Similarity NPD7584 Approved
0.7117 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD5124 Phase 1
0.7115 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD422 Phase 1
0.7093 Intermediate Similarity NPD7229 Phase 3
0.7093 Intermediate Similarity NPD3787 Discontinued
0.7074 Intermediate Similarity NPD7435 Discontinued
0.7067 Intermediate Similarity NPD1608 Approved
0.7066 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD6386 Approved
0.7066 Intermediate Similarity NPD6385 Approved
0.7056 Intermediate Similarity NPD8434 Phase 2
0.7051 Intermediate Similarity NPD4060 Phase 1
0.7041 Intermediate Similarity NPD4288 Approved
0.7032 Intermediate Similarity NPD6798 Discontinued
0.7032 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD411 Approved
0.7032 Intermediate Similarity NPD3764 Approved
0.7027 Intermediate Similarity NPD1651 Approved
0.7027 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD6844 Discontinued
0.702 Intermediate Similarity NPD2982 Phase 2
0.702 Intermediate Similarity NPD4749 Approved
0.702 Intermediate Similarity NPD2983 Phase 2

  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