Structure

Physi-Chem Properties

Molecular Weight:  354.11
Volume:  357.82
LogP:  4.463
LogD:  2.619
LogS:  -3.39
# Rotatable Bonds:  3
TPSA:  111.13
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.533
Synthetic Accessibility Score:  2.768
Fsp3:  0.15
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.956
MDCK Permeability:  1.22268638733658e-05
Pgp-inhibitor:  0.019
Pgp-substrate:  0.102
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.926
30% Bioavailability (F30%):  0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.007
Plasma Protein Binding (PPB):  97.49994659423828%
Volume Distribution (VD):  0.609
Pgp-substrate:  4.067227840423584%

ADMET: Metabolism

CYP1A2-inhibitor:  0.952
CYP1A2-substrate:  0.148
CYP2C19-inhibitor:  0.737
CYP2C19-substrate:  0.049
CYP2C9-inhibitor:  0.775
CYP2C9-substrate:  0.776
CYP2D6-inhibitor:  0.841
CYP2D6-substrate:  0.26
CYP3A4-inhibitor:  0.462
CYP3A4-substrate:  0.077

ADMET: Excretion

Clearance (CL):  7.588
Half-life (T1/2):  0.844

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.315
Drug-inuced Liver Injury (DILI):  0.975
AMES Toxicity:  0.529
Rat Oral Acute Toxicity:  0.133
Maximum Recommended Daily Dose:  0.475
Skin Sensitization:  0.859
Carcinogencity:  0.075
Eye Corrosion:  0.004
Eye Irritation:  0.912
Respiratory Toxicity:  0.103

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC200694

Natural Product ID:  NPC200694
Common Name*:   Isolicoflavonol
IUPAC Name:   3,5,7-trihydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]chromen-4-one
Synonyms:   Isolicoflavonol
Standard InCHIKey:  PGCKDCPTJAQQSQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C20H18O6/c1-10(2)3-4-11-7-12(5-6-14(11)22)20-19(25)18(24)17-15(23)8-13(21)9-16(17)26-20/h3,5-9,21-23,25H,4H2,1-2H3
SMILES:  CC(=CCc1cc(ccc1O)c1c(c(=O)c2c(cc(cc2o1)O)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL457679
PubChem CID:   5318585
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001615] Flavones
          • [CHEMONTID:0003502] 3'-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
NPO3499 Macaranga conifera Species Euphorbiaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(02)00378-3]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. root n.a. PMID[11395279]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota whole plants n.a. n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota whole plants Shawnee National Forest, Harrisburg, IL, US n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. PMID[12419367]
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]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota leaves Kaohsiung, Taiwan 2006-SEP PMID[18986201]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota Fruits n.a. n.a. PMID[19296617]
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]
NPO3499 Macaranga conifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[21275386]
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]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. formosan n.a. PMID[8864236]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. PMID[9358644]
NPO3499 Macaranga conifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5495 Broussonetia papyrifera Species Moraceae 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[HerDing]
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]
NPO3499 Macaranga conifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5495 Broussonetia papyrifera Species Moraceae 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]
NPO5495 Broussonetia papyrifera Species Moraceae 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]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3499 Macaranga conifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
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]
NPO5495 Broussonetia papyrifera Species Moraceae 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]
NPO29384 Glycyrrhiza glabra 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
NPT441 Individual Protein Cytochrome P450 19A1 Homo sapiens IC50 = 100.0 nM PMID[504187]
NPT2630 Individual Protein mRNA interferase MazF Escherichia coli K-12 EC50 > 99000.0 nM PMID[504188]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 6309.6 nM PMID[504188]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 22387.2 nM PMID[504188]
NPT2630 Individual Protein mRNA interferase MazF Escherichia coli K-12 EC50 = 14000.0 nM PMID[504188]
NPT534 Individual Protein Phosphoglycerate kinase, glycosomal Trypanosoma brucei brucei Potency n.a. 28183.8 nM PMID[504188]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 730.8 nM PMID[504188]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[504188]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 18356.4 nM PMID[504188]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 35481.3 nM PMID[504188]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 98.0 % PMID[504189]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 56234.1 nM PMID[504188]
NPT9 Individual Protein DNA polymerase eta Homo sapiens Potency n.a. 19952.6 nM PMID[504188]
NPT2 Others Unspecified Potency n.a. 7943.3 nM PMID[504188]
NPT2 Others Unspecified Potency n.a. 19952.6 nM PMID[504188]
NPT2 Others Unspecified AC50 = 17150.0 nM PMID[504188]
NPT2 Others Unspecified Activity = 48.5 % PMID[504190]
NPT2 Others Unspecified Activity = 10.1 % PMID[504190]
NPT2 Others Unspecified Activity = 7.7 % PMID[504190]
NPT2 Others Unspecified Activity = 95.2 % PMID[504190]
NPT2 Others Unspecified Activity = 61.2 % PMID[504190]
NPT2 Others Unspecified FC = 0.8 n.a. PMID[504190]
NPT2 Others Unspecified Ki = 37700.0 nM PMID[504190]
NPT2 Others Unspecified Inhibition = 60.0 % PMID[504190]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 40000.0 nM PMID[504190]

☑ 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 NPC200694 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
0.9927 High Similarity NPC293053
0.9927 High Similarity NPC190637
0.9927 High Similarity NPC24821
0.9927 High Similarity NPC212932
0.9927 High Similarity NPC9117
0.9855 High Similarity NPC216538
0.9855 High Similarity NPC273538
0.9855 High Similarity NPC326500
0.9854 High Similarity NPC473042
0.9784 High Similarity NPC178343
0.9784 High Similarity NPC124729
0.9784 High Similarity NPC306488
0.9784 High Similarity NPC5820
0.9783 High Similarity NPC158874
0.9779 High Similarity NPC220062
0.9779 High Similarity NPC96565
0.9779 High Similarity NPC301217
0.9779 High Similarity NPC303633
0.9779 High Similarity NPC216978
0.9779 High Similarity NPC55018
0.9714 High Similarity NPC166757
0.9714 High Similarity NPC14001
0.9708 High Similarity NPC172986
0.9708 High Similarity NPC159275
0.9708 High Similarity NPC241100
0.9708 High Similarity NPC261227
0.9708 High Similarity NPC270883
0.9706 High Similarity NPC201395
0.9645 High Similarity NPC244407
0.9645 High Similarity NPC296869
0.9643 High Similarity NPC220418
0.9643 High Similarity NPC470458
0.9638 High Similarity NPC90582
0.9638 High Similarity NPC110969
0.9638 High Similarity NPC64908
0.9638 High Similarity NPC118840
0.9638 High Similarity NPC262094
0.9638 High Similarity NPC156590
0.9638 High Similarity NPC147688
0.9638 High Similarity NPC282300
0.9638 High Similarity NPC205006
0.9635 High Similarity NPC18260
0.9635 High Similarity NPC152042
0.9635 High Similarity NPC78913
0.9635 High Similarity NPC217186
0.9635 High Similarity NPC241838
0.9635 High Similarity NPC143799
0.9635 High Similarity NPC53181
0.9577 High Similarity NPC269420
0.9577 High Similarity NPC470461
0.9568 High Similarity NPC226636
0.9568 High Similarity NPC62840
0.9568 High Similarity NPC59739
0.9568 High Similarity NPC217083
0.9568 High Similarity NPC293852
0.9568 High Similarity NPC299080
0.9568 High Similarity NPC11561
0.9568 High Similarity NPC78803
0.9568 High Similarity NPC214236
0.9565 High Similarity NPC69769
0.9565 High Similarity NPC281207
0.9565 High Similarity NPC269652
0.9565 High Similarity NPC235239
0.9565 High Similarity NPC103342
0.9565 High Similarity NPC475680
0.9565 High Similarity NPC103904
0.9565 High Similarity NPC146679
0.9565 High Similarity NPC230285
0.9565 High Similarity NPC184536
0.9565 High Similarity NPC305355
0.9565 High Similarity NPC59951
0.9565 High Similarity NPC150522
0.9562 High Similarity NPC276905
0.9559 High Similarity NPC281917
0.9559 High Similarity NPC13408
0.9559 High Similarity NPC216361
0.9559 High Similarity NPC187432
0.9559 High Similarity NPC116775
0.9559 High Similarity NPC256042
0.951 High Similarity NPC61258
0.9507 High Similarity NPC470460
0.95 High Similarity NPC11700
0.95 High Similarity NPC38219
0.95 High Similarity NPC219915
0.9496 High Similarity NPC14871
0.9496 High Similarity NPC103362
0.9496 High Similarity NPC136840
0.9489 High Similarity NPC299379
0.9433 High Similarity NPC224714
0.9433 High Similarity NPC234629
0.9433 High Similarity NPC319752
0.9433 High Similarity NPC311741
0.9429 High Similarity NPC148757
0.9429 High Similarity NPC76372
0.9429 High Similarity NPC32739
0.9429 High Similarity NPC66515
0.9429 High Similarity NPC166482
0.9429 High Similarity NPC107572
0.9429 High Similarity NPC161506
0.9429 High Similarity NPC36181
0.9429 High Similarity NPC324436
0.9429 High Similarity NPC194432
0.9429 High Similarity NPC37496
0.9429 High Similarity NPC166934
0.9429 High Similarity NPC167624
0.9429 High Similarity NPC220998
0.9429 High Similarity NPC76338
0.9429 High Similarity NPC227579
0.9429 High Similarity NPC228504
0.9429 High Similarity NPC324134
0.9429 High Similarity NPC78
0.9429 High Similarity NPC223500
0.9429 High Similarity NPC328164
0.9429 High Similarity NPC204469
0.9429 High Similarity NPC177354
0.9429 High Similarity NPC64915
0.9429 High Similarity NPC10937
0.9429 High Similarity NPC265040
0.9429 High Similarity NPC40833
0.9429 High Similarity NPC125855
0.9429 High Similarity NPC182852
0.9429 High Similarity NPC296917
0.9429 High Similarity NPC1089
0.9429 High Similarity NPC144499
0.9429 High Similarity NPC306829
0.942 High Similarity NPC470669
0.942 High Similarity NPC470668
0.9416 High Similarity NPC29353
0.9416 High Similarity NPC124784
0.9416 High Similarity NPC231772
0.9416 High Similarity NPC473887
0.9416 High Similarity NPC127447
0.9416 High Similarity NPC194281
0.9416 High Similarity NPC234133
0.9416 High Similarity NPC174999
0.9416 High Similarity NPC47815
0.9412 High Similarity NPC248872
0.9379 High Similarity NPC63187
0.9379 High Similarity NPC37684
0.9379 High Similarity NPC45934
0.9379 High Similarity NPC142527
0.9379 High Similarity NPC157784
0.9371 High Similarity NPC168085
0.9366 High Similarity NPC20488
0.9366 High Similarity NPC111786
0.9366 High Similarity NPC195621
0.9366 High Similarity NPC472629
0.9366 High Similarity NPC267375
0.9366 High Similarity NPC176229
0.9366 High Similarity NPC214774
0.9366 High Similarity NPC154217
0.9366 High Similarity NPC54577
0.9366 High Similarity NPC153758
0.9366 High Similarity NPC312973
0.9366 High Similarity NPC88964
0.9366 High Similarity NPC470647
0.9366 High Similarity NPC142405
0.9366 High Similarity NPC474161
0.9366 High Similarity NPC301276
0.9366 High Similarity NPC475052
0.9366 High Similarity NPC246948
0.9366 High Similarity NPC67805
0.9366 High Similarity NPC83357
0.9366 High Similarity NPC329678
0.9366 High Similarity NPC476088
0.9362 High Similarity NPC81697
0.9362 High Similarity NPC188632
0.9362 High Similarity NPC185276
0.9362 High Similarity NPC214166
0.9362 High Similarity NPC18585
0.9362 High Similarity NPC149026
0.9362 High Similarity NPC75049
0.9362 High Similarity NPC91560
0.9362 High Similarity NPC143896
0.9362 High Similarity NPC112791
0.9362 High Similarity NPC166138
0.9362 High Similarity NPC106985
0.9362 High Similarity NPC125894
0.9362 High Similarity NPC107177
0.9362 High Similarity NPC196459
0.9362 High Similarity NPC316816
0.9362 High Similarity NPC223812
0.9362 High Similarity NPC164980
0.9362 High Similarity NPC470296
0.9362 High Similarity NPC169591
0.9362 High Similarity NPC221432
0.9362 High Similarity NPC175504
0.9362 High Similarity NPC77794
0.9362 High Similarity NPC39329
0.9362 High Similarity NPC478086
0.9362 High Similarity NPC310130
0.9362 High Similarity NPC257097
0.9362 High Similarity NPC85162
0.9362 High Similarity NPC150408
0.9362 High Similarity NPC68104
0.9362 High Similarity NPC278249
0.9362 High Similarity NPC87609
0.9362 High Similarity NPC470216
0.9362 High Similarity NPC94794
0.9357 High Similarity NPC96408

  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 NPC200694 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
0.9855 High Similarity NPD4378 Clinical (unspecified phase)
0.9296 High Similarity NPD7410 Clinical (unspecified phase)
0.9071 High Similarity NPD1550 Clinical (unspecified phase)
0.9071 High Similarity NPD1552 Clinical (unspecified phase)
0.9007 High Similarity NPD1549 Phase 2
0.8966 High Similarity NPD1512 Approved
0.8929 High Similarity NPD1510 Phase 2
0.8926 High Similarity NPD2393 Clinical (unspecified phase)
0.8913 High Similarity NPD1240 Approved
0.8874 High Similarity NPD7075 Discontinued
0.8865 High Similarity NPD2796 Approved
0.8859 High Similarity NPD6801 Discontinued
0.8851 High Similarity NPD4380 Phase 2
0.8828 High Similarity NPD1511 Approved
0.88 High Similarity NPD7096 Clinical (unspecified phase)
0.8792 High Similarity NPD7411 Suspended
0.8786 High Similarity NPD1607 Approved
0.8742 High Similarity NPD8443 Clinical (unspecified phase)
0.8699 High Similarity NPD6799 Approved
0.8675 High Similarity NPD2801 Approved
0.8609 High Similarity NPD1934 Approved
0.8608 High Similarity NPD7804 Clinical (unspecified phase)
0.8553 High Similarity NPD7819 Suspended
0.8552 High Similarity NPD2800 Approved
0.8506 High Similarity NPD4381 Clinical (unspecified phase)
0.8497 Intermediate Similarity NPD3817 Phase 2
0.8493 Intermediate Similarity NPD3750 Approved
0.8477 Intermediate Similarity NPD6599 Discontinued
0.8442 Intermediate Similarity NPD3882 Suspended
0.8425 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8418 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8418 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8418 Intermediate Similarity NPD6166 Phase 2
0.8344 Intermediate Similarity NPD6959 Discontinued
0.8323 Intermediate Similarity NPD7768 Phase 2
0.8302 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8299 Intermediate Similarity NPD1243 Approved
0.8278 Intermediate Similarity NPD5403 Approved
0.8264 Intermediate Similarity NPD6651 Approved
0.8239 Intermediate Similarity NPD2313 Discontinued
0.8239 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8231 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8219 Intermediate Similarity NPD2935 Discontinued
0.816 Intermediate Similarity NPD6797 Phase 2
0.8158 Intermediate Similarity NPD920 Approved
0.8153 Intermediate Similarity NPD3749 Approved
0.8151 Intermediate Similarity NPD3748 Approved
0.8151 Intermediate Similarity NPD2799 Discontinued
0.8146 Intermediate Similarity NPD5401 Approved
0.811 Intermediate Similarity NPD7251 Discontinued
0.8095 Intermediate Similarity NPD1551 Phase 2
0.8086 Intermediate Similarity NPD3818 Discontinued
0.8063 Intermediate Similarity NPD6232 Discontinued
0.8061 Intermediate Similarity NPD7808 Phase 3
0.8061 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.805 Intermediate Similarity NPD5494 Approved
0.8041 Intermediate Similarity NPD2344 Approved
0.8037 Intermediate Similarity NPD7054 Approved
0.8037 Intermediate Similarity NPD7286 Phase 2
0.8026 Intermediate Similarity NPD2532 Approved
0.8026 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8026 Intermediate Similarity NPD2534 Approved
0.8026 Intermediate Similarity NPD2533 Approved
0.8025 Intermediate Similarity NPD7473 Discontinued
0.8025 Intermediate Similarity NPD5402 Approved
0.8014 Intermediate Similarity NPD1203 Approved
0.8013 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD7472 Approved
0.7988 Intermediate Similarity NPD7074 Phase 3
0.7986 Intermediate Similarity NPD3268 Approved
0.7952 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD5953 Discontinued
0.7935 Intermediate Similarity NPD3226 Approved
0.7905 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7892 Intermediate Similarity NPD6559 Discontinued
0.7888 Intermediate Similarity NPD1247 Approved
0.7887 Intermediate Similarity NPD2797 Approved
0.7881 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7875 Intermediate Similarity NPD919 Approved
0.7862 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD422 Phase 1
0.7852 Intermediate Similarity NPD6099 Approved
0.7852 Intermediate Similarity NPD6100 Approved
0.7843 Intermediate Similarity NPD7390 Discontinued
0.7832 Intermediate Similarity NPD2798 Approved
0.7829 Intermediate Similarity NPD2309 Approved
0.7826 Intermediate Similarity NPD1548 Phase 1
0.7801 Intermediate Similarity NPD9717 Approved
0.78 Intermediate Similarity NPD2346 Discontinued
0.7785 Intermediate Similarity NPD7033 Discontinued
0.7755 Intermediate Similarity NPD943 Approved
0.773 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD4908 Phase 1
0.7724 Intermediate Similarity NPD6832 Phase 2
0.7714 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD5844 Phase 1
0.7701 Intermediate Similarity NPD4363 Phase 3
0.7701 Intermediate Similarity NPD4360 Phase 2
0.7692 Intermediate Similarity NPD3225 Approved
0.7683 Intermediate Similarity NPD3926 Phase 2
0.7667 Intermediate Similarity NPD4308 Phase 3
0.7647 Intermediate Similarity NPD4628 Phase 3
0.7647 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD3267 Approved
0.7639 Intermediate Similarity NPD3266 Approved
0.7619 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD1610 Phase 2
0.7584 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD5124 Phase 1
0.7582 Intermediate Similarity NPD2654 Approved
0.7557 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD4361 Phase 2
0.7551 Intermediate Similarity NPD4625 Phase 3
0.7516 Intermediate Similarity NPD1465 Phase 2
0.75 Intermediate Similarity NPD1296 Phase 2
0.75 Intermediate Similarity NPD6798 Discontinued
0.7483 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD4288 Approved
0.7456 Intermediate Similarity NPD1729 Discontinued
0.7451 Intermediate Similarity NPD1471 Phase 3
0.7434 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD1608 Approved
0.7431 Intermediate Similarity NPD3972 Approved
0.7415 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD5711 Approved
0.741 Intermediate Similarity NPD5710 Approved
0.7405 Intermediate Similarity NPD5049 Phase 3
0.74 Intermediate Similarity NPD4307 Phase 2
0.7386 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD2354 Approved
0.7361 Intermediate Similarity NPD1201 Approved
0.7358 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD1933 Approved
0.7351 Intermediate Similarity NPD447 Suspended
0.7333 Intermediate Similarity NPD6233 Phase 2
0.7329 Intermediate Similarity NPD6585 Discontinued
0.7324 Intermediate Similarity NPD9545 Approved
0.7321 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD2403 Approved
0.731 Intermediate Similarity NPD1481 Phase 2
0.7305 Intermediate Similarity NPD9493 Approved
0.7305 Intermediate Similarity NPD7229 Phase 3
0.7285 Intermediate Similarity NPD1613 Approved
0.7285 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD5890 Approved
0.7284 Intermediate Similarity NPD5889 Approved
0.7279 Intermediate Similarity NPD1470 Approved
0.7279 Intermediate Similarity NPD1164 Approved
0.7273 Intermediate Similarity NPD5406 Approved
0.7273 Intermediate Similarity NPD5404 Approved
0.7273 Intermediate Similarity NPD5405 Approved
0.7273 Intermediate Similarity NPD5408 Approved
0.7267 Intermediate Similarity NPD411 Approved
0.7267 Intermediate Similarity NPD3764 Approved
0.7267 Intermediate Similarity NPD7458 Discontinued
0.726 Intermediate Similarity NPD4749 Approved
0.7256 Intermediate Similarity NPD2296 Approved
0.7243 Intermediate Similarity NPD7584 Approved
0.7241 Intermediate Similarity NPD1535 Discovery
0.7237 Intermediate Similarity NPD230 Phase 1
0.7237 Intermediate Similarity NPD6355 Discontinued
0.7235 Intermediate Similarity NPD3751 Discontinued
0.7233 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD1019 Discontinued
0.7226 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD2353 Approved
0.7222 Intermediate Similarity NPD17 Approved
0.7214 Intermediate Similarity NPD1241 Discontinued
0.7202 Intermediate Similarity NPD3787 Discontinued
0.7198 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD7003 Approved
0.7175 Intermediate Similarity NPD4287 Approved
0.7171 Intermediate Similarity NPD4060 Phase 1
0.717 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD6104 Discontinued
0.716 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD8434 Phase 2
0.7153 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD3887 Approved
0.7135 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD1652 Phase 2
0.7134 Intermediate Similarity NPD6844 Discontinued
0.7133 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD6776 Approved
0.7104 Intermediate Similarity NPD6782 Approved
0.7104 Intermediate Similarity NPD6780 Approved
0.7104 Intermediate Similarity NPD6781 Approved
0.7104 Intermediate Similarity NPD6777 Approved
0.7104 Intermediate Similarity NPD6778 Approved
0.7104 Intermediate Similarity NPD6779 Approved
0.7086 Intermediate Similarity NPD8312 Approved
0.7086 Intermediate Similarity NPD3027 Phase 3
0.7086 Intermediate Similarity NPD8313 Approved
0.707 Intermediate Similarity NPD2424 Discontinued
0.7067 Intermediate Similarity NPD2861 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