Structure

Physi-Chem Properties

Molecular Weight:  390.13
Volume:  374.753
LogP:  1.468
LogD:  1.753
LogS:  -4.005
# Rotatable Bonds:  4
TPSA:  117.84
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.619
Synthetic Accessibility Score:  4.049
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.702
MDCK Permeability:  9.664458048064262e-06
Pgp-inhibitor:  0.003
Pgp-substrate:  0.96
Human Intestinal Absorption (HIA):  0.021
20% Bioavailability (F20%):  0.122
30% Bioavailability (F30%):  0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.114
Plasma Protein Binding (PPB):  91.01338195800781%
Volume Distribution (VD):  0.689
Pgp-substrate:  10.67534351348877%

ADMET: Metabolism

CYP1A2-inhibitor:  0.056
CYP1A2-substrate:  0.853
CYP2C19-inhibitor:  0.053
CYP2C19-substrate:  0.329
CYP2C9-inhibitor:  0.131
CYP2C9-substrate:  0.621
CYP2D6-inhibitor:  0.188
CYP2D6-substrate:  0.527
CYP3A4-inhibitor:  0.864
CYP3A4-substrate:  0.389

ADMET: Excretion

Clearance (CL):  11.035
Half-life (T1/2):  0.687

ADMET: Toxicity

hERG Blockers:  0.05
Human Hepatotoxicity (H-HT):  0.439
Drug-inuced Liver Injury (DILI):  0.071
AMES Toxicity:  0.907
Rat Oral Acute Toxicity:  0.307
Maximum Recommended Daily Dose:  0.376
Skin Sensitization:  0.425
Carcinogencity:  0.293
Eye Corrosion:  0.003
Eye Irritation:  0.224
Respiratory Toxicity:  0.518

Download Data

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

  Natural Product: NPC4940

Natural Product ID:  NPC4940
Common Name*:   Prinsepiol
IUPAC Name:   (3R,3aS,6R,6aS)-3,6-bis(4-hydroxy-3-methoxyphenyl)-1,3,4,6-tetrahydrofuro[3,4-c]furan-3a,6a-diol
Synonyms:   Prinsepiol
Standard InCHIKey:  IUWMJMIMXOEDKV-ZRNYENFQSA-N
Standard InCHI:  InChI=1S/C20H22O8/c1-25-15-7-11(3-5-13(15)21)17-19(23)9-28-18(20(19,24)10-27-17)12-4-6-14(22)16(8-12)26-2/h3-8,17-18,21-24H,9-10H2,1-2H3/t17-,18-,19+,20+/m1/s1
SMILES:  COc1cc(ccc1O)[C@H]1OC[C@]2([C@]1(O)CO[C@@H]2c1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL470456
PubChem CID:   3010931
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans

*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
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.foodchem.2013.08.121]
NPO14102 Kadsura interior Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[12350139]
NPO15563 Valeriana prionophylla Species Caprifoliaceae Eukaryota n.a. n.a. n.a. PMID[15270567]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Flowers n.a. n.a. PMID[16180814]
NPO8258 Camellia sinensis Species Theaceae Eukaryota seeds Shizuoka prefecture, Japan n.a. PMID[16499314]
NPO5547 Hypericum prolificum Species Hypericaceae Eukaryota aerial parts n.a. n.a. PMID[17125240]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[18068204]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[21434603]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. flower n.a. PMID[21922925]
NPO8258 Camellia sinensis Species Theaceae Eukaryota flower buds n.a. n.a. PMID[21925888]
NPO8258 Camellia sinensis Species Theaceae Eukaryota leaves n.a. n.a. PMID[22377672]
NPO33401 schisandra sphenathera Species Schisandraceae Eukaryota stems n.a. n.a. PMID[23237974]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. leaf n.a. PMID[23265489]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaves Bandung, West Java, Indonesia PMID[23621359]
NPO10230 Trichilia connaroides Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[31589431]
NPO14102 Kadsura interior Species Schisandraceae Eukaryota n.a. stem n.a. PMID[8946749]
NPO15006 Asparagus africanus Species Asparagaceae Eukaryota n.a. n.a. n.a. PMID[9358645]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Seed Oil n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Cotyledon n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO13081 Valeriana laxiflora Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14102 Kadsura interior Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6080 Ericerus pela Species Coccidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6080 Ericerus pela Species Coccidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14102 Kadsura interior Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13081 Valeriana laxiflora Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13156 Cynanchum aphyllum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15563 Valeriana prionophylla Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25336 Halichondria melanadocia Species Halichondriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13530 Thorectandra excavatus Species Thorectidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26873 Echinochloa crus-galli Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16099 Penstemon newberryi Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11868 Malassezia furfur Species Malasseziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14102 Kadsura interior Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14901 Neocosmospora tenuicristata Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6080 Ericerus pela Species Coccidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10230 Trichilia connaroides Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15006 Asparagus africanus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29013 Annulohypoxylon cohaerens Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1967 Solanum chilense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13081 Valeriana laxiflora Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1302 Orobanche speciosa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1305 Eriophyllum confertiflorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5547 Hypericum prolificum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11775 Ophelia neglecta Species Opheliidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7437 Lonchocarpus costaricensis 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 5.33 mM PMID[559762]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 6.7 mM PMID[559762]
NPT177 Tissue Aorta Rattus norvegicus Activity = 29.3 % PMID[559762]
NPT177 Tissue Aorta Rattus norvegicus Activity = 36.7 % PMID[559762]

☑ 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 NPC4940 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
0.9841 High Similarity NPC207400
0.9841 High Similarity NPC181049
0.9762 High Similarity NPC228346
0.9762 High Similarity NPC27843
0.9762 High Similarity NPC158079
0.9762 High Similarity NPC161557
0.9762 High Similarity NPC40432
0.9762 High Similarity NPC115207
0.9762 High Similarity NPC7171
0.9606 High Similarity NPC277804
0.9528 High Similarity NPC257582
0.9528 High Similarity NPC241522
0.9528 High Similarity NPC145305
0.9528 High Similarity NPC64201
0.9528 High Similarity NPC92164
0.9528 High Similarity NPC242807
0.9528 High Similarity NPC42300
0.9528 High Similarity NPC77040
0.9528 High Similarity NPC187998
0.9528 High Similarity NPC153739
0.9528 High Similarity NPC174495
0.9524 High Similarity NPC128208
0.9524 High Similarity NPC45774
0.9524 High Similarity NPC129570
0.9524 High Similarity NPC21867
0.9524 High Similarity NPC282703
0.9524 High Similarity NPC184733
0.9524 High Similarity NPC11258
0.9462 High Similarity NPC24490
0.9462 High Similarity NPC34103
0.9462 High Similarity NPC165155
0.9462 High Similarity NPC126409
0.9462 High Similarity NPC141765
0.9462 High Similarity NPC99572
0.9449 High Similarity NPC475875
0.9389 High Similarity NPC471988
0.937 High Similarity NPC470084
0.9313 High Similarity NPC135777
0.9313 High Similarity NPC142547
0.9308 High Similarity NPC158331
0.9291 High Similarity NPC118533
0.9291 High Similarity NPC165045
0.9291 High Similarity NPC5428
0.9248 High Similarity NPC88640
0.9248 High Similarity NPC193666
0.9248 High Similarity NPC123526
0.9237 High Similarity NPC67247
0.9237 High Similarity NPC287745
0.9237 High Similarity NPC244983
0.9237 High Similarity NPC326095
0.9231 High Similarity NPC204215
0.9231 High Similarity NPC175067
0.9219 High Similarity NPC252307
0.9219 High Similarity NPC245826
0.9219 High Similarity NPC474178
0.9213 High Similarity NPC206882
0.9206 High Similarity NPC18449
0.9206 High Similarity NPC121783
0.9206 High Similarity NPC131747
0.9206 High Similarity NPC257682
0.9206 High Similarity NPC34902
0.9206 High Similarity NPC146355
0.9191 High Similarity NPC84181
0.9179 High Similarity NPC55793
0.9141 High Similarity NPC147821
0.9141 High Similarity NPC319625
0.9141 High Similarity NPC183181
0.9141 High Similarity NPC163332
0.9141 High Similarity NPC292056
0.9141 High Similarity NPC41706
0.9141 High Similarity NPC118787
0.9141 High Similarity NPC111247
0.9134 High Similarity NPC148627
0.9127 High Similarity NPC31344
0.9127 High Similarity NPC317769
0.9127 High Similarity NPC471693
0.9124 High Similarity NPC18979
0.9118 High Similarity NPC477898
0.9098 High Similarity NPC29799
0.9098 High Similarity NPC477939
0.9098 High Similarity NPC209985
0.9098 High Similarity NPC10737
0.9098 High Similarity NPC156502
0.9098 High Similarity NPC177160
0.9098 High Similarity NPC77861
0.9098 High Similarity NPC54743
0.9098 High Similarity NPC263367
0.9091 High Similarity NPC187616
0.9091 High Similarity NPC471942
0.9091 High Similarity NPC193026
0.9091 High Similarity NPC49603
0.9084 High Similarity NPC471505
0.9062 High Similarity NPC178284
0.9062 High Similarity NPC191037
0.9062 High Similarity NPC58607
0.9058 High Similarity NPC112861
0.9051 High Similarity NPC471415
0.9051 High Similarity NPC470097
0.9051 High Similarity NPC114119
0.9037 High Similarity NPC177868
0.903 High Similarity NPC281780
0.9023 High Similarity NPC101624
0.9023 High Similarity NPC184938
0.9008 High Similarity NPC474017
0.9008 High Similarity NPC470096
0.9008 High Similarity NPC470095
0.9 High Similarity NPC5851
0.9 High Similarity NPC170844
0.9 High Similarity NPC476968
0.9 High Similarity NPC86030
0.8986 High Similarity NPC38041
0.8986 High Similarity NPC279298
0.8986 High Similarity NPC469586
0.8986 High Similarity NPC22150
0.8984 High Similarity NPC194519
0.8978 High Similarity NPC46092
0.8978 High Similarity NPC298317
0.8978 High Similarity NPC185071
0.8978 High Similarity NPC12728
0.8978 High Similarity NPC265154
0.8978 High Similarity NPC255566
0.8976 High Similarity NPC473451
0.8976 High Similarity NPC280704
0.8971 High Similarity NPC472711
0.8968 High Similarity NPC126935
0.8968 High Similarity NPC216929
0.8968 High Similarity NPC470212
0.8968 High Similarity NPC324571
0.8968 High Similarity NPC262156
0.8968 High Similarity NPC312713
0.8968 High Similarity NPC343720
0.8968 High Similarity NPC312675
0.8968 High Similarity NPC470804
0.8968 High Similarity NPC172676
0.8968 High Similarity NPC57268
0.8968 High Similarity NPC65933
0.8968 High Similarity NPC473853
0.8968 High Similarity NPC184651
0.8968 High Similarity NPC113865
0.8968 High Similarity NPC54872
0.8947 High Similarity NPC470881
0.8939 High Similarity NPC35932
0.8939 High Similarity NPC160991
0.8939 High Similarity NPC147616
0.8939 High Similarity NPC16208
0.8939 High Similarity NPC201587
0.8939 High Similarity NPC253105
0.8939 High Similarity NPC7903
0.8939 High Similarity NPC219671
0.8939 High Similarity NPC106739
0.8939 High Similarity NPC184447
0.8939 High Similarity NPC259742
0.8939 High Similarity NPC104077
0.8931 High Similarity NPC143483
0.8923 High Similarity NPC186843
0.8923 High Similarity NPC222127
0.8923 High Similarity NPC328682
0.8923 High Similarity NPC82862
0.8923 High Similarity NPC470213
0.8923 High Similarity NPC281864
0.8923 High Similarity NPC72529
0.8923 High Similarity NPC54321
0.8923 High Similarity NPC98631
0.8923 High Similarity NPC206615
0.8921 High Similarity NPC317053
0.8921 High Similarity NPC324492
0.8913 High Similarity NPC470235
0.8913 High Similarity NPC283995
0.8913 High Similarity NPC129417
0.8906 High Similarity NPC114901
0.8906 High Similarity NPC94276
0.8906 High Similarity NPC109822
0.8906 High Similarity NPC48990
0.8906 High Similarity NPC293701
0.8905 High Similarity NPC67467
0.8905 High Similarity NPC476356
0.8905 High Similarity NPC131971
0.8898 High Similarity NPC85488
0.8897 High Similarity NPC184797
0.8897 High Similarity NPC160283
0.8897 High Similarity NPC254759
0.8897 High Similarity NPC309124
0.8889 High Similarity NPC207613
0.8889 High Similarity NPC101807
0.8881 High Similarity NPC93783
0.8881 High Similarity NPC18576
0.8881 High Similarity NPC174191
0.8872 High Similarity NPC169973
0.8872 High Similarity NPC26394
0.8872 High Similarity NPC6836
0.8864 High Similarity NPC472597
0.8857 High Similarity NPC320671
0.8857 High Similarity NPC328567
0.8857 High Similarity NPC327412
0.8857 High Similarity NPC320970
0.8849 High Similarity NPC223185
0.8849 High Similarity NPC477702
0.8846 High Similarity NPC106511
0.8846 High Similarity NPC8050
0.8846 High Similarity NPC473093

  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 NPC4940 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
0.9 High Similarity NPD3027 Phase 3
0.8382 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8382 Intermediate Similarity NPD1613 Approved
0.8254 Intermediate Similarity NPD5283 Phase 1
0.824 Intermediate Similarity NPD228 Approved
0.8222 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8106 Intermediate Similarity NPD3705 Approved
0.8092 Intermediate Similarity NPD6234 Discontinued
0.8015 Intermediate Similarity NPD2861 Phase 2
0.7986 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD3620 Phase 2
0.7985 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7937 Intermediate Similarity NPD3022 Approved
0.7937 Intermediate Similarity NPD3021 Approved
0.7852 Intermediate Similarity NPD2982 Phase 2
0.7852 Intermediate Similarity NPD2983 Phase 2
0.7843 Intermediate Similarity NPD4966 Approved
0.7843 Intermediate Similarity NPD4965 Approved
0.7843 Intermediate Similarity NPD4967 Phase 2
0.7778 Intermediate Similarity NPD2981 Phase 2
0.7778 Intermediate Similarity NPD7266 Discontinued
0.7754 Intermediate Similarity NPD3018 Phase 2
0.7744 Intermediate Similarity NPD1357 Approved
0.7736 Intermediate Similarity NPD7228 Approved
0.773 Intermediate Similarity NPD1558 Phase 1
0.771 Intermediate Similarity NPD7157 Approved
0.7703 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7698 Intermediate Similarity NPD4908 Phase 1
0.7671 Intermediate Similarity NPD4237 Approved
0.7671 Intermediate Similarity NPD4236 Phase 3
0.7647 Intermediate Similarity NPD37 Approved
0.7647 Intermediate Similarity NPD1934 Approved
0.7615 Intermediate Similarity NPD7843 Approved
0.7606 Intermediate Similarity NPD4060 Phase 1
0.7589 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD2684 Approved
0.7574 Intermediate Similarity NPD1610 Phase 2
0.7551 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD3060 Approved
0.7534 Intermediate Similarity NPD1375 Discontinued
0.7534 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD5588 Approved
0.7517 Intermediate Similarity NPD5058 Phase 3
0.75 Intermediate Similarity NPD3882 Suspended
0.7484 Intermediate Similarity NPD2978 Approved
0.7484 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD2977 Approved
0.747 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7463 Intermediate Similarity NPD5536 Phase 2
0.745 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD6190 Approved
0.7448 Intermediate Similarity NPD4538 Approved
0.7448 Intermediate Similarity NPD4536 Approved
0.7448 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD6671 Approved
0.7432 Intermediate Similarity NPD6674 Discontinued
0.7431 Intermediate Similarity NPD5735 Approved
0.7421 Intermediate Similarity NPD7199 Phase 2
0.7407 Intermediate Similarity NPD1548 Phase 1
0.7407 Intermediate Similarity NPD3818 Discontinued
0.7394 Intermediate Similarity NPD4625 Phase 3
0.7394 Intermediate Similarity NPD7095 Approved
0.7391 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6166 Phase 2
0.7389 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD1653 Approved
0.7383 Intermediate Similarity NPD4110 Phase 3
0.7383 Intermediate Similarity NPD6331 Phase 2
0.7383 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD2801 Approved
0.7361 Intermediate Similarity NPD2238 Phase 2
0.7347 Intermediate Similarity NPD2161 Phase 2
0.7338 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD4749 Approved
0.7329 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD1091 Approved
0.731 Intermediate Similarity NPD6355 Discontinued
0.7305 Intermediate Similarity NPD6584 Phase 3
0.7303 Intermediate Similarity NPD4123 Phase 3
0.7292 Intermediate Similarity NPD2674 Phase 3
0.7287 Intermediate Similarity NPD968 Approved
0.7286 Intermediate Similarity NPD8651 Approved
0.7286 Intermediate Similarity NPD6696 Suspended
0.7279 Intermediate Similarity NPD5960 Phase 3
0.7267 Intermediate Similarity NPD4628 Phase 3
0.7255 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD3094 Phase 2
0.7233 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD290 Approved
0.7229 Intermediate Similarity NPD7685 Pre-registration
0.7229 Intermediate Similarity NPD7240 Approved
0.7222 Intermediate Similarity NPD5109 Approved
0.7222 Intermediate Similarity NPD5110 Phase 2
0.7222 Intermediate Similarity NPD3020 Approved
0.7222 Intermediate Similarity NPD5111 Phase 2
0.7222 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2677 Approved
0.7215 Intermediate Similarity NPD2563 Approved
0.7215 Intermediate Similarity NPD2560 Approved
0.7212 Intermediate Similarity NPD7074 Phase 3
0.7203 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD5177 Phase 3
0.72 Intermediate Similarity NPD4162 Approved
0.7192 Intermediate Similarity NPD3657 Discovery
0.7181 Intermediate Similarity NPD3540 Phase 1
0.7181 Intermediate Similarity NPD5763 Approved
0.7181 Intermediate Similarity NPD5762 Approved
0.7179 Intermediate Similarity NPD4675 Approved
0.7179 Intermediate Similarity NPD4678 Approved
0.7176 Intermediate Similarity NPD7906 Approved
0.7174 Intermediate Similarity NPD5126 Approved
0.7174 Intermediate Similarity NPD5125 Phase 3
0.7174 Intermediate Similarity NPD6516 Phase 2
0.7174 Intermediate Similarity NPD5846 Approved
0.7172 Intermediate Similarity NPD6233 Phase 2
0.7172 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD4210 Discontinued
0.7152 Intermediate Similarity NPD5772 Approved
0.7152 Intermediate Similarity NPD5773 Approved
0.7152 Intermediate Similarity NPD7054 Approved
0.7143 Intermediate Similarity NPD6353 Approved
0.7143 Intermediate Similarity NPD2232 Approved
0.7143 Intermediate Similarity NPD7311 Approved
0.7143 Intermediate Similarity NPD6653 Approved
0.7143 Intermediate Similarity NPD2230 Approved
0.7143 Intermediate Similarity NPD7312 Approved
0.7143 Intermediate Similarity NPD7313 Approved
0.7143 Intermediate Similarity NPD7310 Approved
0.7143 Intermediate Similarity NPD2233 Approved
0.7133 Intermediate Similarity NPD9494 Approved
0.7124 Intermediate Similarity NPD1511 Approved
0.7124 Intermediate Similarity NPD4357 Discontinued
0.7123 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD2859 Approved
0.712 Intermediate Similarity NPD2860 Approved
0.7115 Intermediate Similarity NPD4005 Discontinued
0.7114 Intermediate Similarity NPD3539 Phase 1
0.7109 Intermediate Similarity NPD291 Approved
0.7108 Intermediate Similarity NPD7472 Approved
0.7107 Intermediate Similarity NPD3817 Phase 2
0.7105 Intermediate Similarity NPD5241 Discontinued
0.7103 Intermediate Similarity NPD6798 Discontinued
0.7103 Intermediate Similarity NPD3144 Approved
0.7103 Intermediate Similarity NPD3145 Approved
0.7101 Intermediate Similarity NPD7309 Approved
0.7101 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD6583 Phase 3
0.7092 Intermediate Similarity NPD6582 Phase 2
0.7092 Intermediate Similarity NPD5327 Phase 3
0.7078 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD2489 Approved
0.7073 Intermediate Similarity NPD27 Approved
0.7071 Intermediate Similarity NPD3092 Approved
0.707 Intermediate Similarity NPD4380 Phase 2
0.7063 Intermediate Similarity NPD4624 Approved
0.7063 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7124 Phase 2
0.7055 Intermediate Similarity NPD6232 Discontinued
0.7051 Intermediate Similarity NPD3686 Approved
0.7051 Intermediate Similarity NPD3687 Approved
0.705 Intermediate Similarity NPD2668 Approved
0.705 Intermediate Similarity NPD2667 Approved
0.7047 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD7033 Discontinued
0.7044 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD4578 Approved
0.7041 Intermediate Similarity NPD4577 Approved
0.704 Intermediate Similarity NPD2934 Approved
0.704 Intermediate Similarity NPD2933 Approved
0.704 Intermediate Similarity NPD9296 Approved
0.7039 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD5494 Approved
0.7032 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD7526 Approved
0.7032 Intermediate Similarity NPD1512 Approved
0.7032 Intermediate Similarity NPD52 Approved
0.7029 Intermediate Similarity NPD1182 Approved
0.7021 Intermediate Similarity NPD1608 Approved
0.7021 Intermediate Similarity NPD2235 Phase 2
0.7021 Intermediate Similarity NPD2231 Phase 2
0.7021 Intermediate Similarity NPD1840 Phase 2
0.702 Intermediate Similarity NPD2424 Discontinued
0.7018 Intermediate Similarity NPD4663 Approved
0.7012 Intermediate Similarity NPD2970 Approved
0.7012 Intermediate Similarity NPD2969 Approved
0.7007 Intermediate Similarity NPD4140 Approved
0.7007 Intermediate Similarity NPD3061 Approved
0.7007 Intermediate Similarity NPD3059 Approved
0.7007 Intermediate Similarity NPD3062 Approved
0.7 Intermediate Similarity NPD2438 Suspended
0.6994 Remote Similarity NPD8127 Discontinued
0.6992 Remote Similarity NPD5451 Approved
0.6987 Remote Similarity NPD5976 Discontinued
0.6986 Remote Similarity NPD6859 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