Structure

Physi-Chem Properties

Molecular Weight:  372.19
Volume:  391.531
LogP:  4.358
LogD:  3.846
LogS:  -5.088
# Rotatable Bonds:  6
TPSA:  46.15
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.728
Synthetic Accessibility Score:  3.194
Fsp3:  0.455
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.824
MDCK Permeability:  5.8381265262141824e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.03
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.085
30% Bioavailability (F30%):  0.705

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.187
Plasma Protein Binding (PPB):  85.13053894042969%
Volume Distribution (VD):  1.404
Pgp-substrate:  4.4518256187438965%

ADMET: Metabolism

CYP1A2-inhibitor:  0.053
CYP1A2-substrate:  0.967
CYP2C19-inhibitor:  0.902
CYP2C19-substrate:  0.907
CYP2C9-inhibitor:  0.863
CYP2C9-substrate:  0.85
CYP2D6-inhibitor:  0.115
CYP2D6-substrate:  0.929
CYP3A4-inhibitor:  0.937
CYP3A4-substrate:  0.849

ADMET: Excretion

Clearance (CL):  8.285
Half-life (T1/2):  0.349

ADMET: Toxicity

hERG Blockers:  0.248
Human Hepatotoxicity (H-HT):  0.099
Drug-inuced Liver Injury (DILI):  0.919
AMES Toxicity:  0.166
Rat Oral Acute Toxicity:  0.083
Maximum Recommended Daily Dose:  0.04
Skin Sensitization:  0.6
Carcinogencity:  0.196
Eye Corrosion:  0.004
Eye Irritation:  0.178
Respiratory Toxicity:  0.096

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Similar NPs/Drugs  

  Natural Product: NPC312713

Natural Product ID:  NPC312713
Common Name*:   2,5-Bis-(3,4-Dimethoxy-Phenyl)-3,4-Dimethyl-Tetrahydro-Furan
IUPAC Name:   (2R,3S,4S,5R)-2,5-bis(3,4-dimethoxyphenyl)-3,4-dimethyloxolane
Synonyms:  
Standard InCHIKey:  JLJAVUZBHSLLJL-HCIHMXRSSA-N
Standard InCHI:  InChI=1S/C22H28O5/c1-13-14(2)22(16-8-10-18(24-4)20(12-16)26-6)27-21(13)15-7-9-17(23-3)19(11-15)25-5/h7-14,21-22H,1-6H3/t13-,14-,21+,22+/m0/s1
SMILES:  C[C@H]1[C@H](C)[C@H](c2ccc(c(c2)OC)OC)O[C@H]1c1ccc(c(c1)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL57542
PubChem CID:   443018
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans
        • [CHEMONTID:0001604] Tetrahydrofuran lignans
          • [CHEMONTID:0003423] 7,7'-epoxylignans

*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
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)99818-1]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[10924192]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[11421725]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[11754613]
NPO18321 Medicago sativa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[12232319]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. root n.a. PMID[14750033]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[15165135]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[15482936]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota seeds n.a. n.a. PMID[17998162]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota roots n.a. n.a. PMID[18841903]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. PMID[1955885]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. fruit n.a. PMID[20879744]
NPO18321 Medicago sativa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22208890]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota Roots n.a. n.a. PMID[24359277]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota Aerial Parts n.a. n.a. PMID[24387347]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. PMID[27419473]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[31642320]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO18321 Medicago sativa Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Aril n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18321 Medicago sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8303 Catalpa bignonioides Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18321 Medicago sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8303 Catalpa bignonioides Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18321 Medicago sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5334 Rhodotypos scandens Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28409 Lens phaseoloides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2665 Andinobates fulguritus Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8532 Helipterum tenellum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8303 Catalpa bignonioides Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6113 Piper pedicellosum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5162 Comaster multifida Species Comatulidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4539 Ipomoea cristulata Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO490 Lophozonia menziesii Species 0thofagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17811 Cephalonoplos segetum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20323 Saururus chinensis Species Saururaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5746 Pancratium trianthum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18321 Medicago sativa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19928 Lachnoanaerobaculum saburreum Species Lachnospiraceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7393 Esenbeckia nesiotica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7237 Xanthostemon oppositifolius Species Myrtaceae 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
NPT1372 Individual Protein Platelet activating factor receptor Cavia porcellus IC50 = 4500.0 nM PMID[568445]

☑ 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 NPC312713 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 NPC57268
1.0 High Similarity NPC172676
1.0 High Similarity NPC65933
1.0 High Similarity NPC126935
1.0 High Similarity NPC216929
0.9744 High Similarity NPC18449
0.9744 High Similarity NPC34902
0.9744 High Similarity NPC121783
0.958 High Similarity NPC50683
0.958 High Similarity NPC206882
0.958 High Similarity NPC112571
0.958 High Similarity NPC285725
0.95 High Similarity NPC98745
0.9421 High Similarity NPC129570
0.9421 High Similarity NPC11258
0.9421 High Similarity NPC21867
0.9421 High Similarity NPC226862
0.9421 High Similarity NPC282703
0.9421 High Similarity NPC82862
0.9421 High Similarity NPC45774
0.9421 High Similarity NPC184733
0.9421 High Similarity NPC128208
0.9421 High Similarity NPC470084
0.9421 High Similarity NPC165128
0.9421 High Similarity NPC158471
0.9421 High Similarity NPC222127
0.9421 High Similarity NPC57119
0.9417 High Similarity NPC9891
0.9417 High Similarity NPC88297
0.9417 High Similarity NPC186845
0.9339 High Similarity NPC473093
0.9339 High Similarity NPC8050
0.9339 High Similarity NPC473092
0.9304 High Similarity NPC9341
0.9304 High Similarity NPC81067
0.9268 High Similarity NPC42300
0.9268 High Similarity NPC271208
0.9268 High Similarity NPC241522
0.9268 High Similarity NPC257582
0.9268 High Similarity NPC77040
0.9268 High Similarity NPC233224
0.9268 High Similarity NPC92164
0.9268 High Similarity NPC242807
0.9268 High Similarity NPC174495
0.9268 High Similarity NPC145305
0.9268 High Similarity NPC64201
0.9268 High Similarity NPC153739
0.9268 High Similarity NPC187998
0.9262 High Similarity NPC328682
0.9262 High Similarity NPC281864
0.9262 High Similarity NPC54321
0.9211 High Similarity NPC165106
0.9194 High Similarity NPC82111
0.9194 High Similarity NPC158079
0.9194 High Similarity NPC277804
0.9194 High Similarity NPC7171
0.9194 High Similarity NPC227160
0.9194 High Similarity NPC115207
0.9194 High Similarity NPC27843
0.9194 High Similarity NPC161557
0.9194 High Similarity NPC228346
0.9194 High Similarity NPC40432
0.9187 High Similarity NPC475875
0.912 High Similarity NPC7744
0.912 High Similarity NPC230219
0.912 High Similarity NPC181049
0.912 High Similarity NPC207400
0.9113 High Similarity NPC470624
0.9113 High Similarity NPC237169
0.9052 High Similarity NPC47194
0.9052 High Similarity NPC473264
0.9052 High Similarity NPC475815
0.9048 High Similarity NPC158331
0.9048 High Similarity NPC26394
0.9048 High Similarity NPC266848
0.9048 High Similarity NPC136750
0.9024 High Similarity NPC165045
0.9024 High Similarity NPC118533
0.9016 High Similarity NPC148627
0.9008 High Similarity NPC317769
0.9008 High Similarity NPC279379
0.9008 High Similarity NPC31344
0.9 High Similarity NPC477886
0.8992 High Similarity NPC344161
0.8983 High Similarity NPC474040
0.8976 High Similarity NPC90083
0.8976 High Similarity NPC193026
0.8976 High Similarity NPC170779
0.8976 High Similarity NPC67247
0.8976 High Similarity NPC187616
0.8976 High Similarity NPC471942
0.8976 High Similarity NPC49603
0.8976 High Similarity NPC474478
0.8976 High Similarity NPC287745
0.8968 High Similarity NPC33611
0.8968 High Similarity NPC65183
0.8968 High Similarity NPC219671
0.8968 High Similarity NPC129687
0.8968 High Similarity NPC475856
0.8968 High Similarity NPC471505
0.8968 High Similarity NPC158526
0.8968 High Similarity NPC204215
0.8968 High Similarity NPC259742
0.8968 High Similarity NPC261812
0.8968 High Similarity NPC104077
0.8968 High Similarity NPC147616
0.8968 High Similarity NPC175067
0.8968 High Similarity NPC100223
0.8968 High Similarity NPC171928
0.8968 High Similarity NPC4940
0.8968 High Similarity NPC16830
0.8968 High Similarity NPC72046
0.896 High Similarity NPC233961
0.896 High Similarity NPC339621
0.896 High Similarity NPC280399
0.8934 High Similarity NPC94276
0.8934 High Similarity NPC109822
0.8926 High Similarity NPC261661
0.8926 High Similarity NPC71090
0.8908 High Similarity NPC254625
0.8908 High Similarity NPC475961
0.8906 High Similarity NPC135777
0.8906 High Similarity NPC93783
0.8906 High Similarity NPC142547
0.8906 High Similarity NPC99572
0.8906 High Similarity NPC126409
0.8906 High Similarity NPC474139
0.8906 High Similarity NPC189474
0.8898 High Similarity NPC1474
0.8889 High Similarity NPC192255
0.8871 High Similarity NPC5428
0.8871 High Similarity NPC158737
0.8852 High Similarity NPC471693
0.8843 High Similarity NPC80241
0.8843 High Similarity NPC301641
0.8837 High Similarity NPC263367
0.8837 High Similarity NPC177160
0.8837 High Similarity NPC77861
0.8837 High Similarity NPC10737
0.8837 High Similarity NPC209985
0.8837 High Similarity NPC471988
0.8837 High Similarity NPC477939
0.8837 High Similarity NPC156502
0.8837 High Similarity NPC54743
0.8837 High Similarity NPC29799
0.8837 High Similarity NPC78047
0.8828 High Similarity NPC244983
0.8828 High Similarity NPC47181
0.8828 High Similarity NPC31530
0.8828 High Similarity NPC326095
0.8824 High Similarity NPC474214
0.8819 High Similarity NPC106739
0.88 High Similarity NPC474178
0.88 High Similarity NPC31707
0.88 High Similarity NPC245826
0.88 High Similarity NPC252307
0.879 High Similarity NPC191037
0.879 High Similarity NPC58607
0.879 High Similarity NPC178284
0.877 High Similarity NPC85488
0.8769 High Similarity NPC281780
0.8769 High Similarity NPC477938
0.876 High Similarity NPC141765
0.876 High Similarity NPC184938
0.876 High Similarity NPC24490
0.876 High Similarity NPC101624
0.876 High Similarity NPC472596
0.876 High Similarity NPC34103
0.876 High Similarity NPC49235
0.876 High Similarity NPC18576
0.876 High Similarity NPC165155
0.876 High Similarity NPC25333
0.876 High Similarity NPC148893
0.875 High Similarity NPC15805
0.875 High Similarity NPC196937
0.875 High Similarity NPC474320
0.874 High Similarity NPC474017
0.874 High Similarity NPC184928
0.874 High Similarity NPC141493
0.873 High Similarity NPC476748
0.872 High Similarity NPC242032
0.872 High Similarity NPC319625
0.872 High Similarity NPC223807
0.872 High Similarity NPC163332
0.872 High Similarity NPC41706
0.872 High Similarity NPC111247
0.872 High Similarity NPC183181
0.872 High Similarity NPC118787
0.872 High Similarity NPC147821
0.872 High Similarity NPC292056
0.871 High Similarity NPC194519
0.8702 High Similarity NPC123526
0.8702 High Similarity NPC193666
0.8702 High Similarity NPC260842
0.8702 High Similarity NPC88640
0.8699 High Similarity NPC473451
0.8699 High Similarity NPC280704
0.8692 High Similarity NPC121651
0.8692 High Similarity NPC143895
0.8682 High Similarity NPC145769

  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 NPC312713 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
0.9211 High Similarity NPD5283 Phase 1
0.8843 High Similarity NPD3705 Approved
0.8583 High Similarity NPD3027 Phase 3
0.8175 Intermediate Similarity NPD2981 Phase 2
0.814 Intermediate Similarity NPD2861 Phase 2
0.813 Intermediate Similarity NPD5536 Phase 2
0.811 Intermediate Similarity NPD2982 Phase 2
0.811 Intermediate Similarity NPD2983 Phase 2
0.8 Intermediate Similarity NPD3018 Phase 2
0.797 Intermediate Similarity NPD1613 Approved
0.797 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7955 Intermediate Similarity NPD5110 Phase 2
0.7955 Intermediate Similarity NPD5111 Phase 2
0.7955 Intermediate Similarity NPD5109 Approved
0.7934 Intermediate Similarity NPD228 Approved
0.7914 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD3657 Discovery
0.7899 Intermediate Similarity NPD4236 Phase 3
0.7899 Intermediate Similarity NPD4237 Approved
0.7857 Intermediate Similarity NPD1357 Approved
0.7836 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD3620 Phase 2
0.7833 Intermediate Similarity NPD2684 Approved
0.7829 Intermediate Similarity NPD5327 Phase 3
0.7823 Intermediate Similarity NPD7157 Approved
0.7803 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7769 Intermediate Similarity NPD3021 Approved
0.7769 Intermediate Similarity NPD3022 Approved
0.7754 Intermediate Similarity NPD1375 Discontinued
0.7737 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7737 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD7843 Approved
0.7714 Intermediate Similarity NPD6331 Phase 2
0.7714 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD4110 Phase 3
0.7692 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD4908 Phase 1
0.7664 Intermediate Similarity NPD6895 Approved
0.7664 Intermediate Similarity NPD6896 Approved
0.7655 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7623 Intermediate Similarity NPD5451 Approved
0.7619 Intermediate Similarity NPD37 Approved
0.7606 Intermediate Similarity NPD7124 Phase 2
0.7589 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD4210 Discontinued
0.7584 Intermediate Similarity NPD4965 Approved
0.7584 Intermediate Similarity NPD4967 Phase 2
0.7584 Intermediate Similarity NPD4966 Approved
0.7581 Intermediate Similarity NPD5535 Approved
0.7578 Intermediate Similarity NPD5585 Approved
0.7574 Intermediate Similarity NPD4060 Phase 1
0.7557 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD2161 Phase 2
0.755 Intermediate Similarity NPD5494 Approved
0.7538 Intermediate Similarity NPD1610 Phase 2
0.7519 Intermediate Similarity NPD17 Approved
0.7518 Intermediate Similarity NPD6355 Discontinued
0.7518 Intermediate Similarity NPD5735 Approved
0.7518 Intermediate Similarity NPD6674 Discontinued
0.7518 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD3060 Approved
0.75 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD8651 Approved
0.75 Intermediate Similarity NPD2922 Phase 1
0.75 Intermediate Similarity NPD1182 Approved
0.7483 Intermediate Similarity NPD6234 Discontinued
0.7482 Intermediate Similarity NPD5588 Approved
0.7481 Intermediate Similarity NPD1840 Phase 2
0.7459 Intermediate Similarity NPD1358 Approved
0.7448 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7445 Intermediate Similarity NPD2979 Phase 3
0.7445 Intermediate Similarity NPD1558 Phase 1
0.7442 Intermediate Similarity NPD1651 Approved
0.7442 Intermediate Similarity NPD5691 Approved
0.7429 Intermediate Similarity NPD2438 Suspended
0.7429 Intermediate Similarity NPD3539 Phase 1
0.7426 Intermediate Similarity NPD5718 Phase 2
0.741 Intermediate Similarity NPD6111 Discontinued
0.741 Intermediate Similarity NPD4538 Approved
0.741 Intermediate Similarity NPD4536 Approved
0.741 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD4162 Approved
0.7385 Intermediate Similarity NPD6516 Phase 2
0.7385 Intermediate Similarity NPD5846 Approved
0.7379 Intermediate Similarity NPD4123 Phase 3
0.7377 Intermediate Similarity NPD3134 Approved
0.7376 Intermediate Similarity NPD3540 Phase 1
0.7376 Intermediate Similarity NPD5763 Approved
0.7376 Intermediate Similarity NPD5762 Approved
0.7361 Intermediate Similarity NPD5058 Phase 3
0.7361 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD7095 Approved
0.7348 Intermediate Similarity NPD1608 Approved
0.7344 Intermediate Similarity NPD3596 Phase 2
0.7329 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD2238 Phase 2
0.7319 Intermediate Similarity NPD4140 Approved
0.7311 Intermediate Similarity NPD3020 Approved
0.7293 Intermediate Similarity NPD4359 Approved
0.7292 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD2677 Approved
0.7279 Intermediate Similarity NPD5976 Discontinued
0.7273 Intermediate Similarity NPD5177 Phase 3
0.7273 Intermediate Similarity NPD1281 Approved
0.7273 Intermediate Similarity NPD7199 Phase 2
0.7267 Intermediate Similarity NPD1934 Approved
0.7266 Intermediate Similarity NPD6671 Approved
0.7259 Intermediate Similarity NPD6584 Phase 3
0.7259 Intermediate Similarity NPD4624 Approved
0.7254 Intermediate Similarity NPD7266 Discontinued
0.7254 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7252 Intermediate Similarity NPD2667 Approved
0.7252 Intermediate Similarity NPD2668 Approved
0.7239 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD968 Approved
0.7234 Intermediate Similarity NPD5960 Phase 3
0.7231 Intermediate Similarity NPD6580 Approved
0.7231 Intermediate Similarity NPD1548 Phase 1
0.7231 Intermediate Similarity NPD6581 Approved
0.7226 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4628 Phase 3
0.7219 Intermediate Similarity NPD5773 Approved
0.7219 Intermediate Similarity NPD2978 Approved
0.7219 Intermediate Similarity NPD2977 Approved
0.7219 Intermediate Similarity NPD5772 Approved
0.7218 Intermediate Similarity NPD2230 Approved
0.7218 Intermediate Similarity NPD2235 Phase 2
0.7218 Intermediate Similarity NPD2233 Approved
0.7218 Intermediate Similarity NPD2232 Approved
0.7218 Intermediate Similarity NPD2231 Phase 2
0.7214 Intermediate Similarity NPD6353 Approved
0.7211 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD52 Approved
0.7211 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD7526 Approved
0.7203 Intermediate Similarity NPD2808 Discontinued
0.7203 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6385 Approved
0.72 Intermediate Similarity NPD6386 Approved
0.7194 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD4005 Discontinued
0.7179 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD290 Approved
0.7176 Intermediate Similarity NPD3443 Approved
0.7176 Intermediate Similarity NPD3444 Approved
0.7176 Intermediate Similarity NPD3445 Approved
0.7176 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD6798 Discontinued
0.7174 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD5241 Discontinued
0.7171 Intermediate Similarity NPD2560 Approved
0.7171 Intermediate Similarity NPD2563 Approved
0.7164 Intermediate Similarity NPD4749 Approved
0.7164 Intermediate Similarity NPD1669 Approved
0.7161 Intermediate Similarity NPD8127 Discontinued
0.7152 Intermediate Similarity NPD7228 Approved
0.7143 Intermediate Similarity NPD1611 Approved
0.7143 Intermediate Similarity NPD1091 Approved
0.7134 Intermediate Similarity NPD4481 Phase 3
0.7133 Intermediate Similarity NPD4678 Approved
0.7133 Intermediate Similarity NPD4675 Approved
0.7132 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD6387 Discontinued
0.7132 Intermediate Similarity NPD2557 Approved
0.7124 Intermediate Similarity NPD3882 Suspended
0.7122 Intermediate Similarity NPD4870 Approved
0.7122 Intermediate Similarity NPD3532 Approved
0.7122 Intermediate Similarity NPD6233 Phase 2
0.7122 Intermediate Similarity NPD3531 Approved
0.7122 Intermediate Similarity NPD3530 Approved
0.7121 Intermediate Similarity NPD5125 Phase 3
0.7121 Intermediate Similarity NPD5126 Approved
0.7121 Intermediate Similarity NPD4626 Approved
0.7115 Intermediate Similarity NPD3051 Approved
0.7114 Intermediate Similarity NPD3687 Approved
0.7114 Intermediate Similarity NPD3686 Approved
0.7113 Intermediate Similarity NPD4108 Discontinued
0.7111 Intermediate Similarity NPD1283 Approved
0.7111 Intermediate Similarity NPD1876 Approved
0.7111 Intermediate Similarity NPD6696 Suspended
0.7105 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD5563 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD7466 Approved
0.7101 Intermediate Similarity NPD4625 Phase 3
0.7092 Intermediate Similarity NPD2653 Approved
0.7092 Intermediate Similarity NPD6653 Approved
0.7075 Intermediate Similarity NPD4357 Discontinued
0.7075 Intermediate Similarity NPD1774 Approved
0.707 Intermediate Similarity NPD2969 Approved
0.707 Intermediate Similarity NPD2970 Approved
0.7068 Intermediate Similarity NPD3847 Discontinued

  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