Structure

Physi-Chem Properties

Molecular Weight:  593.21
Volume:  568.716
LogP:  0.212
LogD:  -0.495
LogS:  -1.303
# Rotatable Bonds:  12
TPSA:  227.22
# H-Bond Aceptor:  14
# H-Bond Donor:  6
# Rings:  3
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.121
Synthetic Accessibility Score:  5.579
Fsp3:  0.5
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.187
MDCK Permeability:  6.0197333368705586e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.972
Human Intestinal Absorption (HIA):  0.979
20% Bioavailability (F20%):  0.358
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.113
Plasma Protein Binding (PPB):  25.008441925048828%
Volume Distribution (VD):  0.201
Pgp-substrate:  64.11151885986328%

ADMET: Metabolism

CYP1A2-inhibitor:  0.014
CYP1A2-substrate:  0.008
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.037
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.024
CYP2D6-inhibitor:  0.037
CYP2D6-substrate:  0.042
CYP3A4-inhibitor:  0.033
CYP3A4-substrate:  0.009

ADMET: Excretion

Clearance (CL):  1.56
Half-life (T1/2):  0.935

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.61
Drug-inuced Liver Injury (DILI):  0.969
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.075
Maximum Recommended Daily Dose:  0.031
Skin Sensitization:  0.052
Carcinogencity:  0.788
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.931

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

  Natural Product: NPC12944

Natural Product ID:  NPC12944
Common Name*:   Lonijaposide T
IUPAC Name:   (2S,3R,4S)-4-[(E)-2-[5-carboxy-1-[(1S)-1-carboxy-3-methylbutyl]pyridin-1-ium-3-yl]ethenyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
Synonyms:  
Standard InCHIKey:  NRCYLHJBIBALDE-TUXMONONSA-N
Standard InCHI:  InChI=1S/C28H35NO13/c1-4-16-17(6-5-14-8-15(24(34)35)10-29(9-14)19(26(38)39)7-13(2)3)18(25(36)37)12-40-27(16)42-28-23(33)22(32)21(31)20(11-30)41-28/h4-6,8-10,12-13,16-17,19-23,27-28,30-33H,1,7,11H2,2-3H3,(H2-,34,35,36,37,38,39)/b6-5+/t16-,17+,19+,20-,21-,22+,23-,27+,28+/m1/s1
SMILES:  C=C[C@@H]1[C@H](/C=C/c2cc(c[n+](c2)[C@@H](CC(C)C)C(=O)[O-])C(=O)O)C(=CO[C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3092667
PubChem CID:   76309957
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides

*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
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1002/elan.200403102]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2012.02.124]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[11077184]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[11141124]
NPO3699 Acacia aulacocarpa Species Fabaceae Eukaryota n.a. leaf n.a. PMID[11735581]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[15844965]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[17602526]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7569 Guatteria boliviana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8418 Anemone flaccida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19948 Neolentinus lepideus Species Gloeophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4823 Psiadia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO471 Ardisia neriifolia Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3597 Rheedia acuminata Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6729 Juniperus brevifolia Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6237 Cryptocarya aschersoniana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4823 Psiadia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19948 Neolentinus lepideus Species Gloeophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8418 Anemone flaccida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5155 Peritassa compta Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5196 Eupatorium argentinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7569 Guatteria boliviana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3699 Acacia aulacocarpa 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. Inhibition < 30.0 % PMID[488213]
NPT339 Organism Influenza A virus H3N2 Influenza A virus H3N2 IC50 = 10300.0 nM PMID[488213]

☑ 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 NPC12944 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 NPC25442
0.9891 High Similarity NPC156044
0.9669 High Similarity NPC59033
0.9613 High Similarity NPC329024
0.9563 High Similarity NPC79223
0.9524 High Similarity NPC111732
0.9454 High Similarity NPC317672
0.9454 High Similarity NPC320748
0.9454 High Similarity NPC324245
0.9405 High Similarity NPC32451
0.9301 High Similarity NPC328559
0.8913 High Similarity NPC182814
0.8817 High Similarity NPC127647
0.875 High Similarity NPC318020
0.8656 High Similarity NPC328798
0.8641 High Similarity NPC325093
0.8641 High Similarity NPC327373
0.8594 High Similarity NPC50997
0.8594 High Similarity NPC160127
0.8579 High Similarity NPC20593
0.8457 Intermediate Similarity NPC325775
0.8441 Intermediate Similarity NPC322043
0.8241 Intermediate Similarity NPC309498
0.8138 Intermediate Similarity NPC317010
0.7941 Intermediate Similarity NPC472752
0.7799 Intermediate Similarity NPC477910
0.774 Intermediate Similarity NPC472553
0.774 Intermediate Similarity NPC476467
0.7681 Intermediate Similarity NPC48042
0.7681 Intermediate Similarity NPC304179
0.7681 Intermediate Similarity NPC472550
0.7678 Intermediate Similarity NPC471014
0.7678 Intermediate Similarity NPC475408
0.7665 Intermediate Similarity NPC75544
0.7642 Intermediate Similarity NPC144779
0.7642 Intermediate Similarity NPC294579
0.7633 Intermediate Similarity NPC63041
0.763 Intermediate Similarity NPC470306
0.7609 Intermediate Similarity NPC263455
0.7606 Intermediate Similarity NPC472555
0.7606 Intermediate Similarity NPC216428
0.7594 Intermediate Similarity NPC471016
0.7594 Intermediate Similarity NPC6981
0.7583 Intermediate Similarity NPC319128
0.7583 Intermediate Similarity NPC228331
0.7581 Intermediate Similarity NPC477911
0.7571 Intermediate Similarity NPC292517
0.7559 Intermediate Similarity NPC62367
0.7554 Intermediate Similarity NPC312860
0.7535 Intermediate Similarity NPC477912
0.7523 Intermediate Similarity NPC84815
0.7523 Intermediate Similarity NPC301368
0.7523 Intermediate Similarity NPC211920
0.7523 Intermediate Similarity NPC124029
0.7512 Intermediate Similarity NPC477908
0.7512 Intermediate Similarity NPC206343
0.7512 Intermediate Similarity NPC475137
0.7512 Intermediate Similarity NPC162812
0.7512 Intermediate Similarity NPC233727
0.7512 Intermediate Similarity NPC475498
0.7512 Intermediate Similarity NPC477902
0.7512 Intermediate Similarity NPC473850
0.7477 Intermediate Similarity NPC148860
0.7477 Intermediate Similarity NPC473506
0.7465 Intermediate Similarity NPC250807
0.7465 Intermediate Similarity NPC477909
0.7465 Intermediate Similarity NPC76565
0.7465 Intermediate Similarity NPC30570
0.7465 Intermediate Similarity NPC57797
0.7465 Intermediate Similarity NPC477907
0.7465 Intermediate Similarity NPC42678
0.7465 Intermediate Similarity NPC471980
0.7453 Intermediate Similarity NPC165837
0.7448 Intermediate Similarity NPC273532
0.7431 Intermediate Similarity NPC328154
0.7421 Intermediate Similarity NPC477906
0.7419 Intermediate Similarity NPC127720
0.7419 Intermediate Similarity NPC127026
0.7418 Intermediate Similarity NPC264674
0.7409 Intermediate Similarity NPC471190
0.7409 Intermediate Similarity NPC470486
0.7409 Intermediate Similarity NPC471977
0.7409 Intermediate Similarity NPC475644
0.7409 Intermediate Similarity NPC475362
0.7406 Intermediate Similarity NPC323551
0.7406 Intermediate Similarity NPC280473
0.7399 Intermediate Similarity NPC170751
0.7383 Intermediate Similarity NPC207531
0.7371 Intermediate Similarity NPC51008
0.7371 Intermediate Similarity NPC41724
0.7364 Intermediate Similarity NPC228377
0.7364 Intermediate Similarity NPC476110
0.7364 Intermediate Similarity NPC122968
0.7364 Intermediate Similarity NPC146824
0.7364 Intermediate Similarity NPC328186
0.7364 Intermediate Similarity NPC475600
0.7364 Intermediate Similarity NPC475631
0.7364 Intermediate Similarity NPC87152
0.7364 Intermediate Similarity NPC477787
0.7364 Intermediate Similarity NPC475601
0.7358 Intermediate Similarity NPC249614
0.7358 Intermediate Similarity NPC470189
0.7358 Intermediate Similarity NPC40919
0.7343 Intermediate Similarity NPC155792
0.7342 Intermediate Similarity NPC150698
0.7342 Intermediate Similarity NPC96801
0.7336 Intermediate Similarity NPC4421
0.7327 Intermediate Similarity NPC114974
0.7321 Intermediate Similarity NPC289086
0.7315 Intermediate Similarity NPC319556
0.7313 Intermediate Similarity NPC44354
0.7309 Intermediate Similarity NPC30456
0.7309 Intermediate Similarity NPC469748
0.7302 Intermediate Similarity NPC62844
0.7302 Intermediate Similarity NPC193361
0.7299 Intermediate Similarity NPC470190
0.7286 Intermediate Similarity NPC207851
0.7277 Intermediate Similarity NPC237702
0.7273 Intermediate Similarity NPC107287
0.7268 Intermediate Similarity NPC109922
0.7265 Intermediate Similarity NPC475303
0.7265 Intermediate Similarity NPC316841
0.7265 Intermediate Similarity NPC292416
0.7265 Intermediate Similarity NPC473689
0.7265 Intermediate Similarity NPC475596
0.7251 Intermediate Similarity NPC475835
0.7246 Intermediate Similarity NPC103361
0.7244 Intermediate Similarity NPC35208
0.7244 Intermediate Similarity NPC475426
0.7244 Intermediate Similarity NPC327769
0.7235 Intermediate Similarity NPC212768
0.7235 Intermediate Similarity NPC473115
0.7235 Intermediate Similarity NPC75600
0.7235 Intermediate Similarity NPC187494
0.7235 Intermediate Similarity NPC158020
0.7235 Intermediate Similarity NPC6576
0.7235 Intermediate Similarity NPC473089
0.7232 Intermediate Similarity NPC319880
0.7232 Intermediate Similarity NPC320324
0.7232 Intermediate Similarity NPC244839
0.7228 Intermediate Similarity NPC167400
0.7227 Intermediate Similarity NPC475271
0.722 Intermediate Similarity NPC135950
0.7217 Intermediate Similarity NPC476090
0.7215 Intermediate Similarity NPC477903
0.7212 Intermediate Similarity NPC57453
0.7195 Intermediate Similarity NPC26881
0.7182 Intermediate Similarity NPC477788
0.7182 Intermediate Similarity NPC235364
0.7174 Intermediate Similarity NPC230085
0.7174 Intermediate Similarity NPC159630
0.7172 Intermediate Similarity NPC164340
0.7169 Intermediate Similarity NPC477901
0.7168 Intermediate Similarity NPC475406
0.7163 Intermediate Similarity NPC244856
0.7143 Intermediate Similarity NPC476114
0.7137 Intermediate Similarity NPC327904
0.7137 Intermediate Similarity NPC38959
0.7136 Intermediate Similarity NPC253314
0.713 Intermediate Similarity NPC14116
0.713 Intermediate Similarity NPC285411
0.7124 Intermediate Similarity NPC238278
0.712 Intermediate Similarity NPC113812
0.7118 Intermediate Similarity NPC253482
0.7117 Intermediate Similarity NPC477900
0.7117 Intermediate Similarity NPC477899
0.7098 Intermediate Similarity NPC474217
0.7098 Intermediate Similarity NPC311196
0.7098 Intermediate Similarity NPC134384
0.7097 Intermediate Similarity NPC274842
0.7081 Intermediate Similarity NPC123395
0.7078 Intermediate Similarity NPC82070
0.7068 Intermediate Similarity NPC138018
0.7067 Intermediate Similarity NPC91125
0.7059 Intermediate Similarity NPC112741
0.7051 Intermediate Similarity NPC306644
0.7051 Intermediate Similarity NPC236424
0.7047 Intermediate Similarity NPC71079
0.7046 Intermediate Similarity NPC478045
0.7039 Intermediate Similarity NPC475533
0.7026 Intermediate Similarity NPC475648
0.7026 Intermediate Similarity NPC41717
0.7009 Intermediate Similarity NPC475315
0.7009 Intermediate Similarity NPC324619
0.7 Intermediate Similarity NPC474767
0.7 Intermediate Similarity NPC314270
0.6996 Remote Similarity NPC180668
0.6996 Remote Similarity NPC471013
0.6996 Remote Similarity NPC148896
0.6975 Remote Similarity NPC472435
0.6974 Remote Similarity NPC85918
0.6968 Remote Similarity NPC52254
0.6961 Remote Similarity NPC291759
0.6958 Remote Similarity NPC472436
0.6957 Remote Similarity NPC471546
0.6939 Remote Similarity NPC127730
0.6939 Remote Similarity NPC278366
0.6938 Remote Similarity NPC292361
0.6937 Remote Similarity NPC54066
0.6933 Remote Similarity NPC471015

  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 NPC12944 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
0.7833 Intermediate Similarity NPD7396 Approved
0.7617 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7539 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.7433 Intermediate Similarity NPD820 Phase 3
0.7269 Intermediate Similarity NPD8325 Phase 3
0.7269 Intermediate Similarity NPD8326 Phase 3
0.7269 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD8468 Phase 2
0.7228 Intermediate Similarity NPD9074 Approved
0.7228 Intermediate Similarity NPD9075 Approved
0.7059 Intermediate Similarity NPD9271 Approved
0.7023 Intermediate Similarity NPD6529 Discontinued
0.7011 Intermediate Similarity NPD107 Approved
0.6971 Remote Similarity NPD5975 Clinical (unspecified phase)
0.6946 Remote Similarity NPD1096 Discontinued
0.6942 Remote Similarity NPD2544 Clinical (unspecified phase)
0.6931 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5088 Discontinued
0.6903 Remote Similarity NPD4086 Phase 1
0.6895 Remote Similarity NPD3795 Approved
0.6895 Remote Similarity NPD3794 Approved
0.6875 Remote Similarity NPD6665 Discontinued
0.6861 Remote Similarity NPD8479 Phase 2
0.6858 Remote Similarity NPD5640 Discontinued
0.6837 Remote Similarity NPD2831 Approved
0.6824 Remote Similarity NPD7885 Phase 2
0.6824 Remote Similarity NPD7886 Phase 2
0.6812 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6792 Remote Similarity NPD8370 Discontinued
0.6779 Remote Similarity NPD8063 Discontinued
0.6771 Remote Similarity NPD6578 Clinical (unspecified phase)
0.6768 Remote Similarity NPD4174 Clinical (unspecified phase)
0.6756 Remote Similarity NPD6298 Discontinued
0.6746 Remote Similarity NPD2336 Approved
0.6744 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6738 Remote Similarity NPD8409 Suspended
0.6726 Remote Similarity NPD8356 Approved
0.6716 Remote Similarity NPD9510 Approved
0.6716 Remote Similarity NPD1643 Phase 3
0.6711 Remote Similarity NPD3280 Approved
0.67 Remote Similarity NPD6642 Approved
0.67 Remote Similarity NPD6641 Approved
0.6697 Remote Similarity NPD3371 Approved
0.6682 Remote Similarity NPD3393 Approved
0.6682 Remote Similarity NPD3394 Approved
0.6682 Remote Similarity NPD3389 Approved
0.6667 Remote Similarity NPD8373 Clinical (unspecified phase)
0.6638 Remote Similarity NPD8289 Discontinued
0.6635 Remote Similarity NPD5317 Clinical (unspecified phase)
0.6631 Remote Similarity NPD203 Clinical (unspecified phase)
0.6622 Remote Similarity NPD7878 Phase 2
0.6622 Remote Similarity NPD6657 Clinical (unspecified phase)
0.662 Remote Similarity NPD2307 Discontinued
0.662 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6619 Remote Similarity NPD3321 Discontinued
0.6609 Remote Similarity NPD8430 Approved
0.6608 Remote Similarity NPD4301 Approved
0.6606 Remote Similarity NPD3947 Discontinued
0.6602 Remote Similarity NPD3178 Discontinued
0.6601 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6591 Remote Similarity NPD2509 Approved
0.6591 Remote Similarity NPD2510 Approved
0.6588 Remote Similarity NPD1977 Clinical (unspecified phase)
0.6578 Remote Similarity NPD4989 Phase 2
0.6577 Remote Similarity NPD4417 Approved
0.6573 Remote Similarity NPD4427 Phase 2
0.6562 Remote Similarity NPD5148 Clinical (unspecified phase)
0.6562 Remote Similarity NPD5149 Phase 2
0.656 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6558 Remote Similarity NPD7777 Approved
0.6558 Remote Similarity NPD53 Approved
0.6558 Remote Similarity NPD7778 Approved
0.6557 Remote Similarity NPD4376 Phase 3
0.6555 Remote Similarity NPD1483 Discontinued
0.6553 Remote Similarity NPD3006 Discontinued
0.6553 Remote Similarity NPD5891 Approved
0.6526 Remote Similarity NPD4529 Approved
0.6526 Remote Similarity NPD1173 Approved
0.6526 Remote Similarity NPD4528 Approved
0.6526 Remote Similarity NPD4526 Approved
0.6524 Remote Similarity NPD9363 Approved
0.6524 Remote Similarity NPD9364 Phase 2
0.652 Remote Similarity NPD6770 Approved
0.6515 Remote Similarity NPD5255 Approved
0.6513 Remote Similarity NPD5965 Clinical (unspecified phase)
0.6505 Remote Similarity NPD8036 Clinical (unspecified phase)
0.6505 Remote Similarity NPD8037 Clinical (unspecified phase)
0.65 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6498 Remote Similarity NPD4491 Clinical (unspecified phase)
0.6496 Remote Similarity NPD7031 Phase 1
0.6482 Remote Similarity NPD2511 Approved
0.6474 Remote Similarity NPD1649 Discontinued
0.6468 Remote Similarity NPD3911 Approved
0.6465 Remote Similarity NPD9382 Approved
0.6465 Remote Similarity NPD9383 Approved
0.6458 Remote Similarity NPD3813 Approved
0.6457 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6445 Remote Similarity NPD8021 Approved
0.6445 Remote Similarity NPD4948 Discontinued
0.6445 Remote Similarity NPD8020 Approved
0.6442 Remote Similarity NPD9362 Approved
0.644 Remote Similarity NPD4805 Approved
0.6422 Remote Similarity NPD4396 Clinical (unspecified phase)
0.642 Remote Similarity NPD6351 Discovery
0.6415 Remote Similarity NPD7233 Approved
0.6415 Remote Similarity NPD7234 Approved
0.6413 Remote Similarity NPD4506 Discontinued
0.6413 Remote Similarity NPD5583 Clinical (unspecified phase)
0.6406 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6405 Remote Similarity NPD8375 Approved
0.6404 Remote Similarity NPD1623 Approved
0.6402 Remote Similarity NPD9506 Approved
0.6393 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6391 Remote Similarity NPD4923 Phase 1
0.6385 Remote Similarity NPD4081 Clinical (unspecified phase)
0.638 Remote Similarity NPD4033 Approved
0.638 Remote Similarity NPD4034 Approved
0.638 Remote Similarity NPD4038 Approved
0.638 Remote Similarity NPD4905 Approved
0.638 Remote Similarity NPD4903 Approved
0.638 Remote Similarity NPD4906 Approved
0.638 Remote Similarity NPD32 Approved
0.638 Remote Similarity NPD4039 Approved
0.638 Remote Similarity NPD4122 Approved
0.638 Remote Similarity NPD4037 Approved
0.638 Remote Similarity NPD4036 Approved
0.638 Remote Similarity NPD4035 Approved
0.638 Remote Similarity NPD31 Approved
0.6377 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6376 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6375 Remote Similarity NPD7576 Discontinued
0.6373 Remote Similarity NPD751 Clinical (unspecified phase)
0.6368 Remote Similarity NPD2896 Discontinued
0.6368 Remote Similarity NPD7467 Discontinued
0.636 Remote Similarity NPD8000 Clinical (unspecified phase)
0.636 Remote Similarity NPD6825 Phase 1
0.6356 Remote Similarity NPD5475 Discontinued
0.6356 Remote Similarity NPD3779 Clinical (unspecified phase)
0.6352 Remote Similarity NPD8371 Clinical (unspecified phase)
0.6351 Remote Similarity NPD7001 Phase 3
0.6351 Remote Similarity NPD7289 Clinical (unspecified phase)
0.6351 Remote Similarity NPD4904 Approved
0.6348 Remote Similarity NPD1996 Discontinued
0.6345 Remote Similarity NPD510 Phase 1
0.6344 Remote Similarity NPD4667 Clinical (unspecified phase)
0.634 Remote Similarity NPD5022 Discontinued
0.6338 Remote Similarity NPD4021 Phase 2
0.6338 Remote Similarity NPD6068 Discontinued
0.6336 Remote Similarity NPD6173 Approved
0.6335 Remote Similarity NPD4804 Approved
0.6327 Remote Similarity NPD5866 Approved
0.6327 Remote Similarity NPD3918 Approved
0.6327 Remote Similarity NPD7069 Discontinued
0.6327 Remote Similarity NPD3917 Approved
0.6327 Remote Similarity NPD3916 Clinical (unspecified phase)
0.6326 Remote Similarity NPD981 Phase 2
0.6318 Remote Similarity NPD9398 Clinical (unspecified phase)
0.6318 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6316 Remote Similarity NPD5490 Discontinued
0.6316 Remote Similarity NPD5898 Approved
0.6316 Remote Similarity NPD5897 Approved
0.6316 Remote Similarity NPD5899 Approved
0.6309 Remote Similarity NPD3925 Approved
0.6308 Remote Similarity NPD5316 Approved
0.6306 Remote Similarity NPD5901 Discontinued
0.6306 Remote Similarity NPD944 Approved
0.6306 Remote Similarity NPD6987 Phase 1
0.6306 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6303 Remote Similarity NPD3569 Discontinued
0.63 Remote Similarity NPD2581 Approved
0.63 Remote Similarity NPD2582 Approved
0.6296 Remote Similarity NPD7967 Discontinued
0.6289 Remote Similarity NPD1352 Discontinued
0.6287 Remote Similarity NPD4239 Clinical (unspecified phase)
0.6283 Remote Similarity NPD7927 Clinical (unspecified phase)
0.6283 Remote Similarity NPD3915 Approved
0.6283 Remote Similarity NPD7470 Discontinued
0.6282 Remote Similarity NPD7426 Phase 1
0.6281 Remote Similarity NPD2809 Approved
0.6278 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6278 Remote Similarity NPD7010 Phase 3
0.6276 Remote Similarity NPD1270 Approved
0.6274 Remote Similarity NPD2814 Clinical (unspecified phase)
0.6274 Remote Similarity NPD3082 Discontinued
0.6273 Remote Similarity NPD4501 Approved
0.6273 Remote Similarity NPD4500 Approved
0.627 Remote Similarity NPD9284 Approved
0.627 Remote Similarity NPD8291 Clinical (unspecified phase)
0.6266 Remote Similarity NPD6752 Phase 1
0.6266 Remote Similarity NPD6753 Phase 1
0.6261 Remote Similarity NPD1926 Approved
0.6256 Remote Similarity NPD1631 Approved
0.6256 Remote Similarity NPD6635 Approved
0.6244 Remote Similarity NPD3315 Phase 3
0.6244 Remote Similarity NPD6872 Clinical (unspecified phase)
0.6244 Remote Similarity NPD7727 Phase 2
0.6239 Remote Similarity NPD8321 Discontinued
0.6239 Remote Similarity NPD7269 Clinical (unspecified phase)
0.6239 Remote Similarity NPD6204 Clinical (unspecified phase)
0.6238 Remote Similarity NPD1618 Phase 2

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data