Structure

Physi-Chem Properties

Molecular Weight:  651.44
Volume:  709.885
LogP:  3.592
LogD:  2.226
LogS:  -4.269
# Rotatable Bonds:  21
TPSA:  124.33
# H-Bond Aceptor:  10
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.157
Synthetic Accessibility Score:  4.738
Fsp3:  0.595
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.955
MDCK Permeability:  3.3616404834901914e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.354
Human Intestinal Absorption (HIA):  0.902
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.42

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.686
Plasma Protein Binding (PPB):  96.10846710205078%
Volume Distribution (VD):  1.097
Pgp-substrate:  2.1245474815368652%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.089
CYP2C19-inhibitor:  0.158
CYP2C19-substrate:  0.911
CYP2C9-inhibitor:  0.202
CYP2C9-substrate:  0.08
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.097
CYP3A4-inhibitor:  0.941
CYP3A4-substrate:  0.923

ADMET: Excretion

Clearance (CL):  6.509
Half-life (T1/2):  0.346

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.731
Drug-inuced Liver Injury (DILI):  0.983
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.041
Maximum Recommended Daily Dose:  0.036
Skin Sensitization:  0.021
Carcinogencity:  0.005
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.034

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

  Natural Product: NPC22746

Natural Product ID:  NPC22746
Common Name*:   Dragonamide E
IUPAC Name:   (E)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-N,2-dimethyloct-2-en-7-ynamide
Synonyms:   Dragonamide E
Standard InCHIKey:  CWZFOUVOKBTZQE-BWDCGURESA-N
Standard InCHI:  InChI=1S/C37H57N5O5/c1-13-14-15-17-20-27(8)34(44)40(10)31(25(4)5)36(46)42(12)32(26(6)7)37(47)41(11)30(24(2)3)35(45)39(9)29(33(38)43)23-28-21-18-16-19-22-28/h1,16,18-22,24-26,29-32H,14-15,17,23H2,2-12H3,(H2,38,43)/b27-20+/t29-,30-,31-,32-/m0/s1
SMILES:  C#CCCC/C=C(/C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=N)O)Cc1ccccc1)C)C(C)C)C)C(C)C)C)C(C)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1076860
PubChem CID:   44627610
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000347] Amino acids and derivatives
            • [CHEMONTID:0000060] Alpha amino acids and derivatives
              • [CHEMONTID:0004321] Phenylalanine and derivatives

*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
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10514329]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10654420]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10691708]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. palauan n.a. PMID[10691729]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10843570]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10924172]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10978206]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076571]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076573]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076574]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11277744]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11389621]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11430000]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11473443]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11922791]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[12762816]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[12828459]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[14575437]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[1517734]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[16643028]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17125217]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17441769]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[18444683]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Singapore n.a. PMID[19093843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19489598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. eastern Caribbean n.a. PMID[19739598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19839606]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20030365]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. panamanian n.a. PMID[20158242]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Floridian n.a. PMID[20166701]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20936843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21138309]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[2128518]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21341718]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21539315]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21806011]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21999614]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[22035372]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[29792428]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[3924698]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[7623050]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[8699186]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9584405]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599278]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599279]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9784156]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria 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
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 10000.0 nM PMID[512691]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 5100.0 nM PMID[512691]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 > 10000.0 nM PMID[512691]

☑ 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 NPC22746 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
0.9333 High Similarity NPC222466
0.9256 High Similarity NPC101719
0.8983 High Similarity NPC239357
0.8678 High Similarity NPC470546
0.8667 High Similarity NPC470544
0.8595 High Similarity NPC470545
0.8468 Intermediate Similarity NPC71684
0.824 Intermediate Similarity NPC200964
0.8217 Intermediate Similarity NPC319766
0.8189 Intermediate Similarity NPC6975
0.8175 Intermediate Similarity NPC202521
0.8154 Intermediate Similarity NPC111428
0.8154 Intermediate Similarity NPC473322
0.8095 Intermediate Similarity NPC476990
0.8047 Intermediate Similarity NPC46427
0.803 Intermediate Similarity NPC130309
0.8029 Intermediate Similarity NPC139326
0.7969 Intermediate Similarity NPC252878
0.7967 Intermediate Similarity NPC276949
0.7967 Intermediate Similarity NPC35850
0.7955 Intermediate Similarity NPC300315
0.7941 Intermediate Similarity NPC132636
0.7903 Intermediate Similarity NPC33742
0.7895 Intermediate Similarity NPC255447
0.7801 Intermediate Similarity NPC138775
0.7778 Intermediate Similarity NPC287401
0.7692 Intermediate Similarity NPC129666
0.7687 Intermediate Similarity NPC200589
0.7676 Intermediate Similarity NPC329761
0.7676 Intermediate Similarity NPC225648
0.7626 Intermediate Similarity NPC163392
0.7626 Intermediate Similarity NPC239762
0.7626 Intermediate Similarity NPC476259
0.7609 Intermediate Similarity NPC127741
0.7609 Intermediate Similarity NPC471265
0.7609 Intermediate Similarity NPC471264
0.7609 Intermediate Similarity NPC68865
0.7607 Intermediate Similarity NPC475439
0.7607 Intermediate Similarity NPC473501
0.76 Intermediate Similarity NPC474584
0.7591 Intermediate Similarity NPC141050
0.7571 Intermediate Similarity NPC269398
0.7571 Intermediate Similarity NPC168113
0.7571 Intermediate Similarity NPC469426
0.7571 Intermediate Similarity NPC469427
0.7571 Intermediate Similarity NPC263493
0.7552 Intermediate Similarity NPC135121
0.7551 Intermediate Similarity NPC469903
0.7535 Intermediate Similarity NPC201244
0.7535 Intermediate Similarity NPC477217
0.7535 Intermediate Similarity NPC315266
0.7521 Intermediate Similarity NPC25565
0.7518 Intermediate Similarity NPC176226
0.7518 Intermediate Similarity NPC197682
0.7518 Intermediate Similarity NPC161069
0.7517 Intermediate Similarity NPC319320
0.7517 Intermediate Similarity NPC287757
0.75 Intermediate Similarity NPC315276
0.75 Intermediate Similarity NPC14672
0.75 Intermediate Similarity NPC285926
0.7465 Intermediate Similarity NPC52748
0.7464 Intermediate Similarity NPC248283
0.7448 Intermediate Similarity NPC2501
0.7445 Intermediate Similarity NPC246079
0.7429 Intermediate Similarity NPC178662
0.7429 Intermediate Similarity NPC476133
0.7429 Intermediate Similarity NPC470884
0.7429 Intermediate Similarity NPC89489
0.7429 Intermediate Similarity NPC92784
0.7429 Intermediate Similarity NPC98424
0.7413 Intermediate Similarity NPC5620
0.7413 Intermediate Similarity NPC313867
0.7413 Intermediate Similarity NPC209509
0.7413 Intermediate Similarity NPC316008
0.74 Intermediate Similarity NPC469898
0.7398 Intermediate Similarity NPC327481
0.7394 Intermediate Similarity NPC468984
0.7365 Intermediate Similarity NPC473002
0.7361 Intermediate Similarity NPC314358
0.7351 Intermediate Similarity NPC469902
0.7351 Intermediate Similarity NPC473003
0.7343 Intermediate Similarity NPC315283
0.7343 Intermediate Similarity NPC476978
0.7343 Intermediate Similarity NPC314388
0.7333 Intermediate Similarity NPC477937
0.7319 Intermediate Similarity NPC325479
0.7297 Intermediate Similarity NPC473341
0.7297 Intermediate Similarity NPC122590
0.7292 Intermediate Similarity NPC322878
0.7279 Intermediate Similarity NPC7817
0.7279 Intermediate Similarity NPC475168
0.7273 Intermediate Similarity NPC27833
0.726 Intermediate Similarity NPC471820
0.726 Intermediate Similarity NPC471821
0.7258 Intermediate Similarity NPC474973
0.7258 Intermediate Similarity NPC474804
0.7258 Intermediate Similarity NPC130898
0.7254 Intermediate Similarity NPC268841
0.7254 Intermediate Similarity NPC307357
0.7254 Intermediate Similarity NPC46098
0.7226 Intermediate Similarity NPC469666
0.7211 Intermediate Similarity NPC254798
0.7211 Intermediate Similarity NPC13470
0.7203 Intermediate Similarity NPC476989
0.7192 Intermediate Similarity NPC16188
0.7192 Intermediate Similarity NPC311658
0.7181 Intermediate Similarity NPC56685
0.7177 Intermediate Similarity NPC143516
0.7176 Intermediate Similarity NPC169328
0.7162 Intermediate Similarity NPC324081
0.7154 Intermediate Similarity NPC202613
0.7153 Intermediate Similarity NPC77905
0.7143 Intermediate Similarity NPC105717
0.7133 Intermediate Similarity NPC470902
0.7124 Intermediate Similarity NPC469901
0.7123 Intermediate Similarity NPC262077
0.7121 Intermediate Similarity NPC237420
0.7121 Intermediate Similarity NPC310467
0.7114 Intermediate Similarity NPC233702
0.7113 Intermediate Similarity NPC43755
0.7111 Intermediate Similarity NPC474082
0.7111 Intermediate Similarity NPC175726
0.7105 Intermediate Similarity NPC197743
0.7105 Intermediate Similarity NPC297145
0.7097 Intermediate Similarity NPC194390
0.7097 Intermediate Similarity NPC189116
0.7097 Intermediate Similarity NPC224610
0.7097 Intermediate Similarity NPC113326
0.7097 Intermediate Similarity NPC88267
0.7086 Intermediate Similarity NPC473580
0.7075 Intermediate Similarity NPC145113
0.707 Intermediate Similarity NPC469904
0.707 Intermediate Similarity NPC473000
0.7067 Intermediate Similarity NPC261934
0.7067 Intermediate Similarity NPC5194
0.7067 Intermediate Similarity NPC262166
0.7059 Intermediate Similarity NPC1390
0.7059 Intermediate Similarity NPC62104
0.704 Intermediate Similarity NPC473418
0.704 Intermediate Similarity NPC67043
0.7031 Intermediate Similarity NPC319579
0.7016 Intermediate Similarity NPC164859
0.7013 Intermediate Similarity NPC469243
0.7013 Intermediate Similarity NPC471527
0.7007 Intermediate Similarity NPC81026
0.7 Intermediate Similarity NPC161972
0.7 Intermediate Similarity NPC300443
0.7 Intermediate Similarity NPC303045
0.6992 Remote Similarity NPC314992
0.6992 Remote Similarity NPC220698
0.6977 Remote Similarity NPC329011
0.6974 Remote Similarity NPC244509
0.697 Remote Similarity NPC2265
0.6967 Remote Similarity NPC322598
0.6954 Remote Similarity NPC286551
0.6954 Remote Similarity NPC202198
0.6944 Remote Similarity NPC77992
0.6939 Remote Similarity NPC266741
0.6933 Remote Similarity NPC473491
0.6923 Remote Similarity NPC314835
0.6917 Remote Similarity NPC254088
0.6913 Remote Similarity NPC240848
0.6911 Remote Similarity NPC12730
0.6908 Remote Similarity NPC39431
0.6906 Remote Similarity NPC152850
0.6906 Remote Similarity NPC89923
0.6906 Remote Similarity NPC71933
0.6906 Remote Similarity NPC105114
0.6906 Remote Similarity NPC239990
0.6903 Remote Similarity NPC475544
0.6899 Remote Similarity NPC473502
0.6894 Remote Similarity NPC197470
0.6889 Remote Similarity NPC45777
0.6889 Remote Similarity NPC478015
0.6889 Remote Similarity NPC478016
0.6889 Remote Similarity NPC478014
0.6889 Remote Similarity NPC477061
0.6887 Remote Similarity NPC162104
0.6883 Remote Similarity NPC323336
0.6883 Remote Similarity NPC324850
0.6883 Remote Similarity NPC326349
0.688 Remote Similarity NPC471317
0.6879 Remote Similarity NPC217804
0.6879 Remote Similarity NPC22883
0.6879 Remote Similarity NPC210377
0.6879 Remote Similarity NPC5719
0.6879 Remote Similarity NPC223207
0.6867 Remote Similarity NPC283783
0.6859 Remote Similarity NPC241794
0.6855 Remote Similarity NPC129486
0.6853 Remote Similarity NPC474473
0.6852 Remote Similarity NPC469900
0.685 Remote Similarity NPC471447
0.6839 Remote Similarity NPC244336
0.6835 Remote Similarity NPC136453
0.6835 Remote Similarity NPC471771
0.6835 Remote Similarity NPC304074
0.6835 Remote Similarity NPC290755
0.6835 Remote Similarity NPC15068
0.681 Remote Similarity NPC473001

  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 NPC22746 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
0.845 Intermediate Similarity NPD6919 Clinical (unspecified phase)
0.8029 Intermediate Similarity NPD7720 Phase 2
0.7955 Intermediate Similarity NPD7979 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD5339 Clinical (unspecified phase)
0.7883 Intermediate Similarity NPD7728 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD7602 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD8076 Discontinued
0.7609 Intermediate Similarity NPD8173 Phase 2
0.7609 Intermediate Similarity NPD8172 Phase 2
0.7594 Intermediate Similarity NPD2585 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD4677 Discontinued
0.7537 Intermediate Similarity NPD3608 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD5367 Discontinued
0.75 Intermediate Similarity NPD3072 Approved
0.75 Intermediate Similarity NPD3071 Approved
0.75 Intermediate Similarity NPD3073 Approved
0.7464 Intermediate Similarity NPD4791 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD6631 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD6901 Phase 3
0.7424 Intermediate Similarity NPD4761 Approved
0.7424 Intermediate Similarity NPD4762 Approved
0.7424 Intermediate Similarity NPD4706 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD7113 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD2088 Approved
0.7394 Intermediate Similarity NPD2087 Approved
0.7379 Intermediate Similarity NPD8290 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD1968 Approved
0.7361 Intermediate Similarity NPD1967 Approved
0.7357 Intermediate Similarity NPD4782 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD7892 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD4504 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD5581 Approved
0.7299 Intermediate Similarity NPD4125 Approved
0.7299 Intermediate Similarity NPD4676 Approved
0.7299 Intermediate Similarity NPD5263 Approved
0.7273 Intermediate Similarity NPD2022 Approved
0.7258 Intermediate Similarity NPD7130 Phase 3
0.7254 Intermediate Similarity NPD5301 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD2584 Suspended
0.7226 Intermediate Similarity NPD3040 Approved
0.7226 Intermediate Similarity NPD4177 Approved
0.7226 Intermediate Similarity NPD4175 Approved
0.7226 Intermediate Similarity NPD3626 Phase 3
0.7222 Intermediate Similarity NPD5341 Clinical (unspecified phase)
0.7214 Intermediate Similarity NPD8416 Discontinued
0.7211 Intermediate Similarity NPD2016 Approved
0.7211 Intermediate Similarity NPD2014 Approved
0.7211 Intermediate Similarity NPD2013 Approved
0.7192 Intermediate Similarity NPD8323 Discontinued
0.7183 Intermediate Similarity NPD4214 Discontinued
0.7174 Intermediate Similarity NPD6359 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD8643 Discontinued
0.7152 Intermediate Similarity NPD7267 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3561 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7342 Discontinued
0.7122 Intermediate Similarity NPD2050 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD2048 Approved
0.7122 Intermediate Similarity NPD2044 Approved
0.7122 Intermediate Similarity NPD2043 Approved
0.7122 Intermediate Similarity NPD2047 Approved
0.7122 Intermediate Similarity NPD2045 Approved
0.7122 Intermediate Similarity NPD2049 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD2051 Approved
0.7122 Intermediate Similarity NPD21 Approved
0.7122 Intermediate Similarity NPD2046 Approved
0.7113 Intermediate Similarity NPD6073 Approved
0.7113 Intermediate Similarity NPD5725 Approved
0.7103 Intermediate Similarity NPD6681 Discovery
0.7095 Intermediate Similarity NPD6088 Approved
0.7092 Intermediate Similarity NPD5323 Approved
0.7092 Intermediate Similarity NPD6623 Phase 3
0.7071 Intermediate Similarity NPD1330 Phase 2
0.7071 Intermediate Similarity NPD1329 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6294 Approved
0.7063 Intermediate Similarity NPD6295 Approved
0.7042 Intermediate Similarity NPD4757 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD4151 Approved
0.7021 Intermediate Similarity NPD941 Approved
0.702 Intermediate Similarity NPD6670 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD8315 Phase 1
0.7014 Intermediate Similarity NPD4158 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD3125 Approved
0.7 Intermediate Similarity NPD5229 Approved
0.7 Intermediate Similarity NPD6078 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5230 Approved
0.6993 Remote Similarity NPD8125 Discontinued
0.6992 Remote Similarity NPD2218 Phase 2
0.6992 Remote Similarity NPD2217 Approved
0.6992 Remote Similarity NPD4760 Clinical (unspecified phase)
0.698 Remote Similarity NPD3987 Approved
0.698 Remote Similarity NPD5614 Approved
0.698 Remote Similarity NPD3988 Approved
0.698 Remote Similarity NPD5613 Approved
0.6975 Remote Similarity NPD1812 Approved
0.6975 Remote Similarity NPD1814 Approved
0.6975 Remote Similarity NPD6690 Approved
0.6972 Remote Similarity NPD4153 Approved
0.6959 Remote Similarity NPD6552 Clinical (unspecified phase)
0.695 Remote Similarity NPD5299 Approved
0.695 Remote Similarity NPD3632 Clinical (unspecified phase)
0.6939 Remote Similarity NPD6860 Clinical (unspecified phase)
0.6928 Remote Similarity NPD2891 Approved
0.6913 Remote Similarity NPD3519 Discontinued
0.6908 Remote Similarity NPD4646 Approved
0.6908 Remote Similarity NPD4648 Approved
0.6908 Remote Similarity NPD4647 Approved
0.6906 Remote Similarity NPD3604 Clinical (unspecified phase)
0.6905 Remote Similarity NPD5717 Approved
0.6905 Remote Similarity NPD999 Phase 2
0.6905 Remote Similarity NPD1040 Phase 2
0.6901 Remote Similarity NPD7634 Clinical (unspecified phase)
0.6899 Remote Similarity NPD3643 Approved
0.6899 Remote Similarity NPD3642 Approved
0.6899 Remote Similarity NPD3644 Approved
0.6894 Remote Similarity NPD1348 Approved
0.6883 Remote Similarity NPD7118 Clinical (unspecified phase)
0.6867 Remote Similarity NPD1581 Approved
0.6867 Remote Similarity NPD1582 Approved
0.6861 Remote Similarity NPD5335 Discontinued
0.6853 Remote Similarity NPD5272 Discontinued
0.6853 Remote Similarity NPD5296 Approved
0.6853 Remote Similarity NPD8265 Approved
0.6842 Remote Similarity NPD3123 Discovery
0.6831 Remote Similarity NPD7908 Discontinued
0.6831 Remote Similarity NPD2078 Clinical (unspecified phase)
0.6828 Remote Similarity NPD4126 Approved
0.6797 Remote Similarity NPD6038 Clinical (unspecified phase)
0.6794 Remote Similarity NPD480 Approved
0.6786 Remote Similarity NPD3588 Discontinued
0.6783 Remote Similarity NPD5747 Discontinued
0.6781 Remote Similarity NPD3480 Approved
0.6776 Remote Similarity NPD7303 Discontinued
0.6776 Remote Similarity NPD5748 Phase 2
0.6763 Remote Similarity NPD2634 Clinical (unspecified phase)
0.6759 Remote Similarity NPD6817 Clinical (unspecified phase)
0.6757 Remote Similarity NPD2437 Approved
0.6757 Remote Similarity NPD2436 Approved
0.6741 Remote Similarity NPD6093 Discontinued
0.6738 Remote Similarity NPD7828 Discontinued
0.6738 Remote Similarity NPD5759 Approved
0.673 Remote Similarity NPD8303 Discontinued
0.6714 Remote Similarity NPD3029 Clinical (unspecified phase)
0.6713 Remote Similarity NPD2846 Clinical (unspecified phase)
0.6713 Remote Similarity NPD6076 Approved
0.6713 Remote Similarity NPD6075 Approved
0.6712 Remote Similarity NPD4077 Clinical (unspecified phase)
0.6712 Remote Similarity NPD6852 Discontinued
0.6711 Remote Similarity NPD4432 Discontinued
0.6711 Remote Similarity NPD5024 Approved
0.6709 Remote Similarity NPD8351 Phase 2
0.6692 Remote Similarity NPD3551 Approved
0.669 Remote Similarity NPD3908 Approved
0.6689 Remote Similarity NPD6609 Clinical (unspecified phase)
0.6688 Remote Similarity NPD4557 Approved
0.6667 Remote Similarity NPD6676 Phase 2
0.6667 Remote Similarity NPD5298 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7613 Discontinued
0.6667 Remote Similarity NPD4119 Approved
0.6667 Remote Similarity NPD5716 Approved
0.6667 Remote Similarity NPD7522 Discontinued
0.6646 Remote Similarity NPD8022 Clinical (unspecified phase)
0.6646 Remote Similarity NPD7484 Phase 3
0.6646 Remote Similarity NPD2097 Approved
0.6646 Remote Similarity NPD7485 Phase 3
0.6643 Remote Similarity NPD4794 Discontinued
0.6643 Remote Similarity NPD6792 Phase 3
0.6643 Remote Similarity NPD6325 Discontinued
0.6643 Remote Similarity NPD2031 Discontinued
0.6642 Remote Similarity NPD4733 Approved
0.6642 Remote Similarity NPD7508 Discontinued
0.6622 Remote Similarity NPD6897 Clinical (unspecified phase)
0.662 Remote Similarity NPD1781 Discontinued
0.6613 Remote Similarity NPD1100 Approved
0.6613 Remote Similarity NPD1099 Approved
0.6613 Remote Similarity NPD9566 Approved
0.6604 Remote Similarity NPD4565 Clinical (unspecified phase)
0.6604 Remote Similarity NPD4564 Clinical (unspecified phase)
0.66 Remote Similarity NPD5264 Approved
0.66 Remote Similarity NPD5265 Approved
0.6596 Remote Similarity NPD6302 Clinical (unspecified phase)
0.6594 Remote Similarity NPD2956 Clinical (unspecified phase)
0.6593 Remote Similarity NPD1344 Phase 2
0.6582 Remote Similarity NPD7599 Phase 2
0.6582 Remote Similarity NPD4567 Approved
0.6582 Remote Similarity NPD4566 Approved
0.6567 Remote Similarity NPD747 Discontinued
0.6562 Remote Similarity NPD2098 Approved
0.6543 Remote Similarity NPD6304 Approved
0.6543 Remote Similarity NPD2890 Approved
0.6543 Remote Similarity NPD2889 Approved
0.6543 Remote Similarity NPD6303 Approved
0.6543 Remote Similarity NPD2888 Approved
0.6543 Remote Similarity NPD2017 Approved
0.6541 Remote Similarity NPD7600 Phase 2
0.6533 Remote Similarity NPD6119 Clinical (unspecified phase)
0.6528 Remote Similarity NPD4497 Clinical (unspecified phase)
0.6525 Remote Similarity NPD5578 Approved
0.6525 Remote Similarity NPD5577 Clinical (unspecified phase)
0.6519 Remote Similarity NPD1323 Discontinued
0.6515 Remote Similarity NPD4253 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