Structure

Physi-Chem Properties

Molecular Weight:  256.07
Volume:  259.033
LogP:  2.956
LogD:  2.896
LogS:  -3.768
# Rotatable Bonds:  1
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.823
Synthetic Accessibility Score:  2.677
Fsp3:  0.133
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.697
MDCK Permeability:  1.2422600775607862e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.032
20% Bioavailability (F20%):  0.864
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.103
Plasma Protein Binding (PPB):  94.12928009033203%
Volume Distribution (VD):  0.495
Pgp-substrate:  4.436861515045166%

ADMET: Metabolism

CYP1A2-inhibitor:  0.933
CYP1A2-substrate:  0.295
CYP2C19-inhibitor:  0.869
CYP2C19-substrate:  0.086
CYP2C9-inhibitor:  0.848
CYP2C9-substrate:  0.938
CYP2D6-inhibitor:  0.898
CYP2D6-substrate:  0.702
CYP3A4-inhibitor:  0.686
CYP3A4-substrate:  0.169

ADMET: Excretion

Clearance (CL):  14.249
Half-life (T1/2):  0.658

ADMET: Toxicity

hERG Blockers:  0.046
Human Hepatotoxicity (H-HT):  0.108
Drug-inuced Liver Injury (DILI):  0.863
AMES Toxicity:  0.337
Rat Oral Acute Toxicity:  0.644
Maximum Recommended Daily Dose:  0.295
Skin Sensitization:  0.871
Carcinogencity:  0.543
Eye Corrosion:  0.01
Eye Irritation:  0.951
Respiratory Toxicity:  0.631

Download Data

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

  Natural Product: NPC287246

Natural Product ID:  NPC287246
Common Name*:   5,7-Dihydroxy-2-Phenyl-2,3-Dihydrochromen-4-One
IUPAC Name:   5,7-dihydroxy-2-phenyl-2,3-dihydrochromen-4-one
Synonyms:  
Standard InCHIKey:  URFCJEUYXNAHFI-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2
SMILES:  c1ccc(cc1)C1CC(=O)c2c(cc(cc2O1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL70518
PubChem CID:   238782
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0000337] Flavans
          • [CHEMONTID:0001632] Flavanones

*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]
NPO40842 Eugenia rigida Species n.a. n.a. n.a. n.a. n.a. PMID[23547843]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota heartwood n.a. n.a. PMID[23743282]
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]
NPO40842 Eugenia rigida Species n.a. n.a. n.a. n.a. n.a. PMID[27618204]
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]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[9525107]
NPO794 Lippia graveolens Species Verbenaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO794 Lippia graveolens Species Verbenaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO794 Lippia graveolens Species Verbenaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18117 Dalbergia odorifera 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]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10597 Fructus syzygii n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO10597 Fructus syzygii n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18117 Dalbergia odorifera 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]
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[TCM_Taiwan]
NPO18117 Dalbergia odorifera 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]
NPO18117 Dalbergia odorifera 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]
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]
NPO794 Lippia graveolens Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1698 Glycyrrhiza inflata 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]
NPO18117 Dalbergia odorifera 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
NPO794 NPC287246 Other Root 9.5 9.5 9.5 mg/100g Database [DUKE]
NPO794 NPC287246 Other Shoot 10.5 10.5 10.5 mg/100g Database [DUKE]
NPO794 NPC287246 Dried Or Powder n.a. 499.3333321 n.a. n.a. mg/100g Database [PHENOL EXPLORER]

☑ 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
NPT54 Individual Protein Nonstructural protein 1 Influenza A virus Potency = 11220.2 nM PMID[518752]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 25918.5 nM PMID[518752]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 23099.9 nM PMID[518752]
NPT484 Individual Protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 16944.1 nM PMID[518752]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 1778.3 nM PMID[518752]
NPT1443 Individual Protein Pyruvate dehydrogenase kinase isoform 1 Homo sapiens Inhibition = 0.75 % PMID[518754]
NPT536 Uncleic Acid microRNA 21 Homo sapiens Potency = 16481.6 nM PMID[518752]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 3294.4 nM PMID[518752]
NPT755 Individual Protein Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens Potency n.a. 89125.1 nM PMID[518752]
NPT2 Others Unspecified Potency n.a. 10000.0 nM PMID[518752]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 42900.0 nM PMID[518753]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 65500.0 nM PMID[518753]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 28800.0 nM PMID[518753]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 78100.0 nM PMID[518753]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[518753]

☑ 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 NPC287246 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 NPC13768
1.0 High Similarity NPC107586
1.0 High Similarity NPC32441
1.0 High Similarity NPC12296
1.0 High Similarity NPC295261
1.0 High Similarity NPC296490
1.0 High Similarity NPC243083
1.0 High Similarity NPC79943
0.9924 High Similarity NPC472460
0.9924 High Similarity NPC147686
0.9924 High Similarity NPC329225
0.985 High Similarity NPC310135
0.985 High Similarity NPC329203
0.985 High Similarity NPC225153
0.985 High Similarity NPC265871
0.985 High Similarity NPC274784
0.985 High Similarity NPC20709
0.985 High Similarity NPC150648
0.985 High Similarity NPC222342
0.9848 High Similarity NPC476480
0.9848 High Similarity NPC84585
0.9776 High Similarity NPC6407
0.9776 High Similarity NPC110228
0.9776 High Similarity NPC188243
0.9774 High Similarity NPC118813
0.9704 High Similarity NPC213322
0.9704 High Similarity NPC4743
0.9704 High Similarity NPC312391
0.9704 High Similarity NPC324386
0.9701 High Similarity NPC316480
0.9701 High Similarity NPC140890
0.9701 High Similarity NPC261234
0.9699 High Similarity NPC275055
0.9699 High Similarity NPC290291
0.9697 High Similarity NPC9985
0.9697 High Similarity NPC239495
0.9632 High Similarity NPC182852
0.9632 High Similarity NPC32739
0.9632 High Similarity NPC296917
0.9632 High Similarity NPC76372
0.9632 High Similarity NPC66515
0.9632 High Similarity NPC78
0.9632 High Similarity NPC166482
0.9632 High Similarity NPC148757
0.9632 High Similarity NPC107572
0.9632 High Similarity NPC324134
0.9632 High Similarity NPC37496
0.9632 High Similarity NPC166934
0.9632 High Similarity NPC306829
0.9632 High Similarity NPC194432
0.9632 High Similarity NPC10937
0.9632 High Similarity NPC220998
0.9632 High Similarity NPC324436
0.9632 High Similarity NPC76338
0.9632 High Similarity NPC125855
0.9632 High Similarity NPC167624
0.9632 High Similarity NPC228504
0.9632 High Similarity NPC227579
0.9632 High Similarity NPC40833
0.9632 High Similarity NPC161506
0.9632 High Similarity NPC265040
0.9632 High Similarity NPC223500
0.9632 High Similarity NPC1089
0.9632 High Similarity NPC328164
0.9632 High Similarity NPC64915
0.9632 High Similarity NPC177354
0.963 High Similarity NPC284550
0.963 High Similarity NPC182421
0.963 High Similarity NPC76445
0.963 High Similarity NPC129853
0.9627 High Similarity NPC188947
0.9627 High Similarity NPC280284
0.9627 High Similarity NPC99333
0.9562 High Similarity NPC143896
0.9562 High Similarity NPC221432
0.9562 High Similarity NPC91560
0.9562 High Similarity NPC278249
0.9562 High Similarity NPC478086
0.9562 High Similarity NPC223812
0.9562 High Similarity NPC175504
0.9562 High Similarity NPC185276
0.9562 High Similarity NPC75049
0.9562 High Similarity NPC107177
0.9562 High Similarity NPC149026
0.9562 High Similarity NPC214166
0.9562 High Similarity NPC310130
0.9562 High Similarity NPC169591
0.9562 High Similarity NPC316816
0.9562 High Similarity NPC68104
0.9562 High Similarity NPC77794
0.9562 High Similarity NPC81697
0.9562 High Similarity NPC39329
0.9562 High Similarity NPC125894
0.9562 High Similarity NPC257097
0.9562 High Similarity NPC85162
0.9562 High Similarity NPC150408
0.9562 High Similarity NPC164980
0.9559 High Similarity NPC96408
0.9559 High Similarity NPC17170
0.9559 High Similarity NPC156190
0.9559 High Similarity NPC279650
0.9559 High Similarity NPC248372
0.9559 High Similarity NPC166689
0.9559 High Similarity NPC3188
0.9559 High Similarity NPC110038
0.9559 High Similarity NPC258630
0.9545 High Similarity NPC274121
0.9545 High Similarity NPC50898
0.9545 High Similarity NPC78540
0.9545 High Similarity NPC213216
0.9493 High Similarity NPC62290
0.9493 High Similarity NPC142731
0.9493 High Similarity NPC208176
0.9493 High Similarity NPC473015
0.9493 High Similarity NPC131568
0.9493 High Similarity NPC279417
0.9493 High Similarity NPC470135
0.9493 High Similarity NPC473013
0.9493 High Similarity NPC326506
0.9493 High Similarity NPC235217
0.9493 High Similarity NPC209040
0.9493 High Similarity NPC306607
0.9493 High Similarity NPC236766
0.9493 High Similarity NPC131579
0.9493 High Similarity NPC470136
0.9493 High Similarity NPC39045
0.9493 High Similarity NPC4152
0.9493 High Similarity NPC473014
0.9493 High Similarity NPC197252
0.9493 High Similarity NPC49130
0.9489 High Similarity NPC73028
0.9489 High Similarity NPC202981
0.9481 High Similarity NPC124269
0.9478 High Similarity NPC29353
0.9478 High Similarity NPC124784
0.9478 High Similarity NPC194281
0.9478 High Similarity NPC231772
0.9478 High Similarity NPC473887
0.9478 High Similarity NPC127447
0.9478 High Similarity NPC234133
0.9478 High Similarity NPC47815
0.9474 High Similarity NPC172262
0.9424 High Similarity NPC83357
0.9424 High Similarity NPC142405
0.9424 High Similarity NPC267375
0.9424 High Similarity NPC20488
0.9424 High Similarity NPC470133
0.9424 High Similarity NPC127059
0.9424 High Similarity NPC285630
0.9424 High Similarity NPC195621
0.9424 High Similarity NPC214774
0.9424 High Similarity NPC470134
0.9424 High Similarity NPC111786
0.9424 High Similarity NPC67805
0.9424 High Similarity NPC176229
0.9424 High Similarity NPC473078
0.9424 High Similarity NPC148011
0.9424 High Similarity NPC470131
0.9424 High Similarity NPC301276
0.9424 High Similarity NPC470132
0.9424 High Similarity NPC312973
0.9424 High Similarity NPC472629
0.9424 High Similarity NPC470647
0.9424 High Similarity NPC88964
0.9424 High Similarity NPC475052
0.9424 High Similarity NPC1940
0.9424 High Similarity NPC54577
0.9424 High Similarity NPC109183
0.9424 High Similarity NPC246948
0.942 High Similarity NPC113770
0.9412 High Similarity NPC18260
0.9412 High Similarity NPC78913
0.9407 High Similarity NPC250266
0.9407 High Similarity NPC188879
0.9407 High Similarity NPC266597
0.9403 High Similarity NPC234560
0.9403 High Similarity NPC99854
0.9403 High Similarity NPC39426
0.9398 High Similarity NPC57601
0.9394 High Similarity NPC113006
0.9357 High Similarity NPC3779
0.9357 High Similarity NPC296998
0.9357 High Similarity NPC476182
0.9357 High Similarity NPC473077
0.9357 High Similarity NPC23728
0.9357 High Similarity NPC211466
0.9357 High Similarity NPC300988
0.9357 High Similarity NPC10990
0.9357 High Similarity NPC122828
0.9357 High Similarity NPC472627
0.9357 High Similarity NPC283234
0.9357 High Similarity NPC40086
0.9357 High Similarity NPC44721
0.9357 High Similarity NPC176869
0.9357 High Similarity NPC110303
0.9353 High Similarity NPC110776
0.9353 High Similarity NPC303185
0.9353 High Similarity NPC87486
0.9353 High Similarity NPC124780
0.9353 High Similarity NPC271590

  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 NPC287246 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
1.0 High Similarity NPD1552 Clinical (unspecified phase)
1.0 High Similarity NPD1550 Clinical (unspecified phase)
0.9924 High Similarity NPD1549 Phase 2
0.9403 High Similarity NPD1510 Phase 2
0.9248 High Similarity NPD1240 Approved
0.9111 High Similarity NPD1607 Approved
0.9078 High Similarity NPD4378 Clinical (unspecified phase)
0.9051 High Similarity NPD2796 Approved
0.9034 High Similarity NPD1934 Approved
0.8973 High Similarity NPD2393 Clinical (unspecified phase)
0.8912 High Similarity NPD8443 Clinical (unspecified phase)
0.8897 High Similarity NPD4380 Phase 2
0.8873 High Similarity NPD1511 Approved
0.8836 High Similarity NPD7411 Suspended
0.8811 High Similarity NPD7410 Clinical (unspecified phase)
0.8792 High Similarity NPD4381 Clinical (unspecified phase)
0.8792 High Similarity NPD7075 Discontinued
0.875 High Similarity NPD1512 Approved
0.8716 High Similarity NPD7096 Clinical (unspecified phase)
0.8643 High Similarity NPD1551 Phase 2
0.8611 High Similarity NPD6799 Approved
0.8591 High Similarity NPD7819 Suspended
0.8561 High Similarity NPD1547 Clinical (unspecified phase)
0.8531 High Similarity NPD3750 Approved
0.8523 High Similarity NPD6801 Discontinued
0.8467 Intermediate Similarity NPD2801 Approved
0.8452 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD6166 Phase 2
0.8452 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8421 Intermediate Similarity NPD3749 Approved
0.8406 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8392 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8389 Intermediate Similarity NPD6599 Discontinued
0.8377 Intermediate Similarity NPD6959 Discontinued
0.8355 Intermediate Similarity NPD3882 Suspended
0.8333 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8311 Intermediate Similarity NPD5403 Approved
0.8309 Intermediate Similarity NPD1203 Approved
0.8299 Intermediate Similarity NPD5401 Approved
0.8291 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD1610 Phase 2
0.8258 Intermediate Similarity NPD1548 Phase 1
0.8239 Intermediate Similarity NPD7074 Phase 3
0.8235 Intermediate Similarity NPD7768 Phase 2
0.8235 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8228 Intermediate Similarity NPD3818 Discontinued
0.8207 Intermediate Similarity NPD2800 Approved
0.8182 Intermediate Similarity NPD3748 Approved
0.8176 Intermediate Similarity NPD7054 Approved
0.817 Intermediate Similarity NPD3817 Phase 2
0.8163 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD7472 Approved
0.8082 Intermediate Similarity NPD1243 Approved
0.8077 Intermediate Similarity NPD5494 Approved
0.8075 Intermediate Similarity NPD6797 Phase 2
0.8069 Intermediate Similarity NPD2344 Approved
0.8067 Intermediate Similarity NPD920 Approved
0.8054 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8042 Intermediate Similarity NPD6651 Approved
0.8028 Intermediate Similarity NPD943 Approved
0.8027 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD7251 Discontinued
0.8 Intermediate Similarity NPD4908 Phase 1
0.7975 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD7808 Phase 3
0.7956 Intermediate Similarity NPD9717 Approved
0.7935 Intermediate Similarity NPD5402 Approved
0.7931 Intermediate Similarity NPD7033 Discontinued
0.7914 Intermediate Similarity NPD6559 Discontinued
0.7905 Intermediate Similarity NPD4628 Phase 3
0.7902 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7902 Intermediate Similarity NPD1613 Approved
0.7887 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7887 Intermediate Similarity NPD2313 Discontinued
0.7883 Intermediate Similarity NPD422 Phase 1
0.7877 Intermediate Similarity NPD2935 Discontinued
0.7877 Intermediate Similarity NPD6100 Approved
0.7877 Intermediate Similarity NPD6099 Approved
0.7872 Intermediate Similarity NPD6832 Phase 2
0.7866 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD5953 Discontinued
0.7852 Intermediate Similarity NPD2309 Approved
0.784 Intermediate Similarity NPD7286 Phase 2
0.7815 Intermediate Similarity NPD2533 Approved
0.7815 Intermediate Similarity NPD2532 Approved
0.7815 Intermediate Similarity NPD2534 Approved
0.7808 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7808 Intermediate Similarity NPD2799 Discontinued
0.7762 Intermediate Similarity NPD3268 Approved
0.7756 Intermediate Similarity NPD1465 Phase 2
0.775 Intermediate Similarity NPD6232 Discontinued
0.7746 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD5844 Phase 1
0.7721 Intermediate Similarity NPD9545 Approved
0.7716 Intermediate Similarity NPD7473 Discontinued
0.7714 Intermediate Similarity NPD3225 Approved
0.7697 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD919 Approved
0.766 Intermediate Similarity NPD2797 Approved
0.7639 Intermediate Similarity NPD1296 Phase 2
0.7628 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD4360 Phase 2
0.7616 Intermediate Similarity NPD4363 Phase 3
0.7613 Intermediate Similarity NPD3226 Approved
0.7612 Intermediate Similarity NPD1241 Discontinued
0.7606 Intermediate Similarity NPD2798 Approved
0.7603 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD1933 Approved
0.7603 Intermediate Similarity NPD5124 Phase 1
0.76 Intermediate Similarity NPD2654 Approved
0.7584 Intermediate Similarity NPD2346 Discontinued
0.7578 Intermediate Similarity NPD1247 Approved
0.7574 Intermediate Similarity NPD9493 Approved
0.7571 Intermediate Similarity NPD1608 Approved
0.7568 Intermediate Similarity NPD4308 Phase 3
0.755 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7535 Intermediate Similarity NPD3266 Approved
0.7535 Intermediate Similarity NPD3267 Approved
0.7517 Intermediate Similarity NPD6798 Discontinued
0.75 Intermediate Similarity NPD1201 Approved
0.7485 Intermediate Similarity NPD3926 Phase 2
0.7484 Intermediate Similarity NPD4288 Approved
0.7483 Intermediate Similarity NPD230 Phase 1
0.7483 Intermediate Similarity NPD1019 Discontinued
0.7483 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD1729 Discontinued
0.7455 Intermediate Similarity NPD3751 Discontinued
0.7447 Intermediate Similarity NPD3972 Approved
0.7447 Intermediate Similarity NPD1481 Phase 2
0.7431 Intermediate Similarity NPD2861 Phase 2
0.7429 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD1470 Approved
0.7403 Intermediate Similarity NPD7390 Discontinued
0.7397 Intermediate Similarity NPD411 Approved
0.7397 Intermediate Similarity NPD3764 Approved
0.7389 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD4287 Approved
0.7381 Intermediate Similarity NPD6104 Discontinued
0.7376 Intermediate Similarity NPD1535 Discovery
0.7372 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD4361 Phase 2
0.7371 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD1652 Phase 2
0.7365 Intermediate Similarity NPD447 Suspended
0.7357 Intermediate Similarity NPD17 Approved
0.7338 Intermediate Similarity NPD1894 Discontinued
0.7333 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD4625 Phase 3
0.7317 Intermediate Similarity NPD5711 Approved
0.7317 Intermediate Similarity NPD3787 Discontinued
0.7317 Intermediate Similarity NPD5710 Approved
0.7297 Intermediate Similarity NPD4307 Phase 2
0.7292 Intermediate Similarity NPD1164 Approved
0.729 Intermediate Similarity NPD7212 Phase 2
0.729 Intermediate Similarity NPD7213 Phase 3
0.7273 Intermediate Similarity NPD4749 Approved
0.7267 Intermediate Similarity NPD2296 Approved
0.725 Intermediate Similarity NPD6844 Discontinued
0.7248 Intermediate Similarity NPD6355 Discontinued
0.7244 Intermediate Similarity NPD4661 Approved
0.7244 Intermediate Similarity NPD4662 Approved
0.7237 Intermediate Similarity NPD1471 Phase 3
0.723 Intermediate Similarity NPD6233 Phase 2
0.7229 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD3027 Phase 3
0.7207 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD8313 Approved
0.7193 Intermediate Similarity NPD8312 Approved
0.7188 Intermediate Similarity NPD5890 Approved
0.7188 Intermediate Similarity NPD5889 Approved
0.7181 Intermediate Similarity NPD3140 Approved
0.7181 Intermediate Similarity NPD3142 Approved
0.7179 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD7458 Discontinued
0.7162 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD3887 Approved
0.7161 Intermediate Similarity NPD2354 Approved
0.7158 Intermediate Similarity NPD7584 Approved
0.7152 Intermediate Similarity NPD7199 Phase 2
0.7143 Intermediate Similarity NPD7577 Discontinued
0.7143 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD7447 Phase 1
0.7133 Intermediate Similarity NPD1091 Approved
0.7124 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD7440 Discontinued
0.7111 Intermediate Similarity NPD9266 Approved
0.7111 Intermediate Similarity NPD74 Approved
0.7108 Intermediate Similarity NPD7229 Phase 3
0.7107 Intermediate Similarity NPD1653 Approved
0.7103 Intermediate Similarity NPD1876 Approved
0.7099 Intermediate Similarity NPD8455 Phase 2
0.709 Intermediate Similarity NPD968 Approved
0.7078 Intermediate Similarity NPD2424 Discontinued
0.7075 Intermediate Similarity NPD9494 Approved
0.7066 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD5406 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