Structure

Physi-Chem Properties

Molecular Weight:  583.21
Volume:  571.898
LogP:  0.252
LogD:  -0.683
LogS:  -1.407
# Rotatable Bonds:  11
TPSA:  189.92
# H-Bond Aceptor:  12
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.162
Synthetic Accessibility Score:  5.31
Fsp3:  0.367
Lipinski Rule-of-5:  Rejected
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:  -6.168
MDCK Permeability:  4.407900632941164e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.295
Human Intestinal Absorption (HIA):  0.974
20% Bioavailability (F20%):  0.249
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.11
Plasma Protein Binding (PPB):  33.201560974121094%
Volume Distribution (VD):  0.239
Pgp-substrate:  61.53928756713867%

ADMET: Metabolism

CYP1A2-inhibitor:  0.034
CYP1A2-substrate:  0.015
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.007
CYP2C9-substrate:  0.014
CYP2D6-inhibitor:  0.022
CYP2D6-substrate:  0.051
CYP3A4-inhibitor:  0.03
CYP3A4-substrate:  0.058

ADMET: Excretion

Clearance (CL):  1.538
Half-life (T1/2):  0.951

ADMET: Toxicity

hERG Blockers:  0.02
Human Hepatotoxicity (H-HT):  0.333
Drug-inuced Liver Injury (DILI):  0.971
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.122
Maximum Recommended Daily Dose:  0.223
Skin Sensitization:  0.043
Carcinogencity:  0.811
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.957

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

  Natural Product: NPC160127

Natural Product ID:  NPC160127
Common Name*:   Lonijaposide S
IUPAC Name:   (2S,3R,4S)-4-[(Z)-2-[1-[(1R)-1-carboxy-2-phenylethyl]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:  NESGKYFUGBYZKP-QZWCVIIJSA-N
Standard InCHI:  InChI=1S/C30H33NO11/c1-2-19-20(11-10-18-9-6-12-31(14-18)22(28(38)39)13-17-7-4-3-5-8-17)21(27(36)37)16-40-29(19)42-30-26(35)25(34)24(33)23(15-32)41-30/h2-12,14,16,19-20,22-26,29-30,32-35H,1,13,15H2,(H-,36,37,38,39)/b11-10-/t19-,20+,22-,23-,24-,25+,26-,29+,30+/m1/s1
SMILES:  C=C[C@@H]1[C@H](/C=Cc2ccc[n+](c2)[C@H](Cc2ccccc2)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:   CHEMBL3092666
PubChem CID:   76328126
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]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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[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]
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]
NPO3699 Acacia aulacocarpa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
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]

☑ 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[482578]

☑ 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 NPC160127 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 NPC50997
0.9379 High Similarity NPC182814
0.9318 High Similarity NPC318020
0.9274 High Similarity NPC127647
0.9205 High Similarity NPC325093
0.9121 High Similarity NPC20593
0.9106 High Similarity NPC328798
0.9058 High Similarity NPC111732
0.8989 High Similarity NPC327373
0.8989 High Similarity NPC322043
0.8895 High Similarity NPC325775
0.8594 High Similarity NPC25442
0.8594 High Similarity NPC12944
0.8505 High Similarity NPC156044
0.8377 Intermediate Similarity NPC59033
0.8229 Intermediate Similarity NPC329024
0.8196 Intermediate Similarity NPC79223
0.8187 Intermediate Similarity NPC317672
0.8093 Intermediate Similarity NPC324245
0.8093 Intermediate Similarity NPC320748
0.8061 Intermediate Similarity NPC328559
0.8061 Intermediate Similarity NPC32451
0.799 Intermediate Similarity NPC476114
0.7981 Intermediate Similarity NPC475271
0.798 Intermediate Similarity NPC476115
0.79 Intermediate Similarity NPC309498
0.7861 Intermediate Similarity NPC474905
0.7843 Intermediate Similarity NPC292517
0.7826 Intermediate Similarity NPC82070
0.7778 Intermediate Similarity NPC162812
0.7729 Intermediate Similarity NPC30570
0.7703 Intermediate Similarity NPC52254
0.7571 Intermediate Similarity NPC174788
0.7527 Intermediate Similarity NPC477975
0.7512 Intermediate Similarity NPC313640
0.7512 Intermediate Similarity NPC475835
0.7455 Intermediate Similarity NPC476090
0.744 Intermediate Similarity NPC472752
0.7421 Intermediate Similarity NPC477976
0.7416 Intermediate Similarity NPC476467
0.7385 Intermediate Similarity NPC207851
0.738 Intermediate Similarity NPC474217
0.7371 Intermediate Similarity NPC216428
0.7326 Intermediate Similarity NPC71079
0.7324 Intermediate Similarity NPC62367
0.7302 Intermediate Similarity NPC477912
0.7297 Intermediate Similarity NPC57453
0.7295 Intermediate Similarity NPC238457
0.7294 Intermediate Similarity NPC124029
0.7294 Intermediate Similarity NPC211920
0.7291 Intermediate Similarity NPC149708
0.729 Intermediate Similarity NPC301368
0.729 Intermediate Similarity NPC84815
0.7281 Intermediate Similarity NPC477902
0.7273 Intermediate Similarity NPC472435
0.7253 Intermediate Similarity NPC472436
0.7249 Intermediate Similarity NPC85918
0.7248 Intermediate Similarity NPC473506
0.7248 Intermediate Similarity NPC148860
0.7243 Intermediate Similarity NPC144779
0.7243 Intermediate Similarity NPC294579
0.7243 Intermediate Similarity NPC314270
0.7235 Intermediate Similarity NPC471980
0.7231 Intermediate Similarity NPC317010
0.723 Intermediate Similarity NPC477909
0.723 Intermediate Similarity NPC477907
0.723 Intermediate Similarity NPC42678
0.723 Intermediate Similarity NPC477910
0.7211 Intermediate Similarity NPC278366
0.7211 Intermediate Similarity NPC127730
0.7209 Intermediate Similarity NPC313804
0.7209 Intermediate Similarity NPC315804
0.7209 Intermediate Similarity NPC472555
0.7202 Intermediate Similarity NPC233727
0.7202 Intermediate Similarity NPC328154
0.7196 Intermediate Similarity NPC471016
0.7196 Intermediate Similarity NPC471014
0.7196 Intermediate Similarity NPC6981
0.7196 Intermediate Similarity NPC475408
0.7195 Intermediate Similarity NPC477906
0.7189 Intermediate Similarity NPC477911
0.7189 Intermediate Similarity NPC127026
0.7189 Intermediate Similarity NPC127720
0.7182 Intermediate Similarity NPC475644
0.7182 Intermediate Similarity NPC471977
0.7182 Intermediate Similarity NPC470486
0.7182 Intermediate Similarity NPC471190
0.7172 Intermediate Similarity NPC62510
0.717 Intermediate Similarity NPC472553
0.7163 Intermediate Similarity NPC281049
0.715 Intermediate Similarity NPC470306
0.7143 Intermediate Similarity NPC471997
0.7136 Intermediate Similarity NPC87152
0.7136 Intermediate Similarity NPC477787
0.7136 Intermediate Similarity NPC328186
0.7136 Intermediate Similarity NPC228377
0.7136 Intermediate Similarity NPC475631
0.7136 Intermediate Similarity NPC229348
0.7136 Intermediate Similarity NPC122968
0.7136 Intermediate Similarity NPC475600
0.7136 Intermediate Similarity NPC476110
0.7123 Intermediate Similarity NPC475137
0.7123 Intermediate Similarity NPC473850
0.7123 Intermediate Similarity NPC475498
0.712 Intermediate Similarity NPC41717
0.7117 Intermediate Similarity NPC150698
0.7117 Intermediate Similarity NPC96801
0.7116 Intermediate Similarity NPC477908
0.7116 Intermediate Similarity NPC206343
0.7109 Intermediate Similarity NPC48042
0.7109 Intermediate Similarity NPC472550
0.7109 Intermediate Similarity NPC304179
0.7109 Intermediate Similarity NPC477548
0.7103 Intermediate Similarity NPC264674
0.7103 Intermediate Similarity NPC4421
0.71 Intermediate Similarity NPC476516
0.7098 Intermediate Similarity NPC170751
0.7089 Intermediate Similarity NPC323551
0.7089 Intermediate Similarity NPC280473
0.7089 Intermediate Similarity NPC244856
0.7085 Intermediate Similarity NPC30456
0.7079 Intermediate Similarity NPC472097
0.7078 Intermediate Similarity NPC76565
0.7078 Intermediate Similarity NPC250807
0.7078 Intermediate Similarity NPC57797
0.7077 Intermediate Similarity NPC150048
0.7077 Intermediate Similarity NPC203754
0.7074 Intermediate Similarity NPC472434
0.7062 Intermediate Similarity NPC63041
0.7056 Intermediate Similarity NPC51008
0.7056 Intermediate Similarity NPC221100
0.7056 Intermediate Similarity NPC234078
0.7056 Intermediate Similarity NPC41724
0.7056 Intermediate Similarity NPC317752
0.7054 Intermediate Similarity NPC237702
0.704 Intermediate Similarity NPC292416
0.704 Intermediate Similarity NPC316841
0.704 Intermediate Similarity NPC473689
0.704 Intermediate Similarity NPC475596
0.704 Intermediate Similarity NPC475303
0.7027 Intermediate Similarity NPC475362
0.7026 Intermediate Similarity NPC469938
0.7023 Intermediate Similarity NPC274842
0.7023 Intermediate Similarity NPC228331
0.7023 Intermediate Similarity NPC319128
0.7022 Intermediate Similarity NPC327769
0.701 Intermediate Similarity NPC103230
0.7009 Intermediate Similarity NPC319880
0.7009 Intermediate Similarity NPC244839
0.7009 Intermediate Similarity NPC318299
0.7009 Intermediate Similarity NPC320324
0.7005 Intermediate Similarity NPC473089
0.7005 Intermediate Similarity NPC474767
0.7005 Intermediate Similarity NPC75600
0.7005 Intermediate Similarity NPC212768
0.7005 Intermediate Similarity NPC6576
0.7005 Intermediate Similarity NPC473115
0.7005 Intermediate Similarity NPC158020
0.7 Intermediate Similarity NPC133591
0.6991 Remote Similarity NPC207531
0.6986 Remote Similarity NPC476874
0.6986 Remote Similarity NPC477903
0.6982 Remote Similarity NPC186351
0.6982 Remote Similarity NPC146824
0.6982 Remote Similarity NPC475601
0.6982 Remote Similarity NPC244536
0.6977 Remote Similarity NPC306644
0.6977 Remote Similarity NPC236424
0.6973 Remote Similarity NPC477974
0.6968 Remote Similarity NPC26881
0.6965 Remote Similarity NPC291759
0.6955 Remote Similarity NPC235364
0.6955 Remote Similarity NPC477788
0.6947 Remote Similarity NPC475406
0.6943 Remote Similarity NPC99891
0.6941 Remote Similarity NPC477901
0.6937 Remote Similarity NPC472762
0.6933 Remote Similarity NPC469748
0.6933 Remote Similarity NPC89987
0.6927 Remote Similarity NPC319556
0.6927 Remote Similarity NPC187494
0.6923 Remote Similarity NPC473800
0.6919 Remote Similarity NPC289086
0.6916 Remote Similarity NPC327904
0.6916 Remote Similarity NPC38959
0.6912 Remote Similarity NPC114974
0.6905 Remote Similarity NPC328318
0.6905 Remote Similarity NPC328596
0.69 Remote Similarity NPC253482
0.6898 Remote Similarity NPC165837
0.6897 Remote Similarity NPC75544
0.6895 Remote Similarity NPC138018
0.6893 Remote Similarity NPC57994
0.6893 Remote Similarity NPC289299
0.6892 Remote Similarity NPC477899
0.6892 Remote Similarity NPC477900
0.689 Remote Similarity NPC128265
0.689 Remote Similarity NPC294909
0.689 Remote Similarity NPC199851
0.689 Remote Similarity NPC254240

  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 NPC160127 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
0.7951 Intermediate Similarity NPD8325 Phase 3
0.7951 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7951 Intermediate Similarity NPD8326 Phase 3
0.7568 Intermediate Similarity NPD5088 Discontinued
0.7512 Intermediate Similarity NPD8372 Clinical (unspecified phase)
0.7422 Intermediate Similarity NPD8468 Phase 2
0.7411 Intermediate Similarity NPD7233 Approved
0.7411 Intermediate Similarity NPD7234 Approved
0.7342 Intermediate Similarity NPD8409 Suspended
0.7288 Intermediate Similarity NPD2896 Discontinued
0.7263 Intermediate Similarity NPD4805 Approved
0.7233 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD7061 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD6529 Discontinued
0.7181 Intermediate Similarity NPD2511 Approved
0.7179 Intermediate Similarity NPD8036 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD8037 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD7396 Approved
0.7151 Intermediate Similarity NPD4804 Approved
0.7129 Intermediate Similarity NPD6665 Discontinued
0.711 Intermediate Similarity NPD8356 Approved
0.7092 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7082 Intermediate Similarity NPD8370 Discontinued
0.7059 Intermediate Similarity NPD2809 Approved
0.7031 Intermediate Similarity NPD4174 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD8063 Discontinued
0.7018 Intermediate Similarity NPD8479 Phase 2
0.7016 Intermediate Similarity NPD6635 Approved
0.6985 Remote Similarity NPD5728 Clinical (unspecified phase)
0.6982 Remote Similarity NPD8430 Approved
0.6982 Remote Similarity NPD4086 Phase 1
0.6976 Remote Similarity NPD4427 Phase 2
0.6974 Remote Similarity NPD7886 Phase 2
0.6974 Remote Similarity NPD7885 Phase 2
0.697 Remote Similarity NPD5897 Approved
0.697 Remote Similarity NPD5899 Approved
0.697 Remote Similarity NPD5898 Approved
0.697 Remote Similarity NPD8375 Approved
0.6959 Remote Similarity NPD4989 Phase 2
0.6952 Remote Similarity NPD5965 Clinical (unspecified phase)
0.6947 Remote Similarity NPD5255 Approved
0.6939 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6935 Remote Similarity NPD8408 Discontinued
0.6934 Remote Similarity NPD7562 Approved
0.6931 Remote Similarity NPD8021 Approved
0.6931 Remote Similarity NPD8020 Approved
0.6927 Remote Similarity NPD4528 Approved
0.6927 Remote Similarity NPD4529 Approved
0.6927 Remote Similarity NPD4526 Approved
0.6923 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6739 Clinical (unspecified phase)
0.691 Remote Similarity NPD8371 Clinical (unspecified phase)
0.6909 Remote Similarity NPD6298 Discontinued
0.6907 Remote Similarity NPD5862 Discovery
0.6898 Remote Similarity NPD3795 Approved
0.6898 Remote Similarity NPD3794 Approved
0.6893 Remote Similarity NPD4602 Approved
0.6893 Remote Similarity NPD7944 Discontinued
0.689 Remote Similarity NPD4501 Approved
0.689 Remote Similarity NPD4500 Approved
0.6888 Remote Similarity NPD6182 Approved
0.6888 Remote Similarity NPD6183 Clinical (unspecified phase)
0.6888 Remote Similarity NPD43 Approved
0.6878 Remote Similarity NPD8373 Clinical (unspecified phase)
0.6875 Remote Similarity NPD53 Approved
0.6875 Remote Similarity NPD7777 Approved
0.6875 Remote Similarity NPD7778 Approved
0.6869 Remote Similarity NPD8122 Approved
0.6869 Remote Similarity NPD8123 Approved
0.6866 Remote Similarity NPD7483 Phase 2
0.6866 Remote Similarity NPD7482 Phase 2
0.6861 Remote Similarity NPD8289 Discontinued
0.6861 Remote Similarity NPD5640 Discontinued
0.6849 Remote Similarity NPD6578 Clinical (unspecified phase)
0.6844 Remote Similarity NPD8374 Phase 3
0.684 Remote Similarity NPD4038 Approved
0.684 Remote Similarity NPD31 Approved
0.684 Remote Similarity NPD4033 Approved
0.684 Remote Similarity NPD32 Approved
0.684 Remote Similarity NPD4039 Approved
0.684 Remote Similarity NPD4035 Approved
0.684 Remote Similarity NPD4122 Approved
0.684 Remote Similarity NPD4037 Approved
0.684 Remote Similarity NPD4034 Approved
0.684 Remote Similarity NPD4036 Approved
0.6829 Remote Similarity NPD2336 Approved
0.6824 Remote Similarity NPD8291 Clinical (unspecified phase)
0.6808 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6798 Remote Similarity NPD8329 Phase 3
0.6784 Remote Similarity NPD6641 Approved
0.6784 Remote Similarity NPD6642 Approved
0.6782 Remote Similarity NPD6178 Phase 3
0.678 Remote Similarity NPD3321 Discontinued
0.678 Remote Similarity NPD2544 Clinical (unspecified phase)
0.6779 Remote Similarity NPD7818 Clinical (unspecified phase)
0.6777 Remote Similarity NPD7903 Clinical (unspecified phase)
0.6777 Remote Similarity NPD3911 Approved
0.6774 Remote Similarity NPD7069 Discontinued
0.6761 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6758 Remote Similarity NPD3394 Approved
0.6758 Remote Similarity NPD3389 Approved
0.6758 Remote Similarity NPD3393 Approved
0.6754 Remote Similarity NPD6026 Approved
0.6745 Remote Similarity NPD7561 Approved
0.6733 Remote Similarity NPD2094 Phase 2
0.6733 Remote Similarity NPD2092 Phase 2
0.6733 Remote Similarity NPD2095 Phase 2
0.673 Remote Similarity NPD6479 Discontinued
0.6719 Remote Similarity NPD2582 Approved
0.6719 Remote Similarity NPD2581 Approved
0.6717 Remote Similarity NPD750 Phase 2
0.6712 Remote Similarity NPD3280 Approved
0.67 Remote Similarity NPD2096 Phase 2
0.67 Remote Similarity NPD2091 Phase 2
0.6699 Remote Similarity NPD2307 Discontinued
0.6698 Remote Similarity NPD7727 Phase 2
0.6682 Remote Similarity NPD8115 Approved
0.6682 Remote Similarity NPD4903 Approved
0.6682 Remote Similarity NPD4906 Approved
0.6682 Remote Similarity NPD4905 Approved
0.6682 Remote Similarity NPD8114 Approved
0.6667 Remote Similarity NPD7947 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6651 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6651 Remote Similarity NPD7957 Phase 1
0.6651 Remote Similarity NPD5975 Clinical (unspecified phase)
0.6651 Remote Similarity NPD4904 Approved
0.665 Remote Similarity NPD6872 Clinical (unspecified phase)
0.6649 Remote Similarity NPD180 Clinical (unspecified phase)
0.6637 Remote Similarity NPD7426 Phase 1
0.6635 Remote Similarity NPD5505 Discontinued
0.6635 Remote Similarity NPD6569 Phase 2
0.6632 Remote Similarity NPD7913 Clinical (unspecified phase)
0.6632 Remote Similarity NPD4671 Clinical (unspecified phase)
0.6632 Remote Similarity NPD4669 Clinical (unspecified phase)
0.6632 Remote Similarity NPD4670 Clinical (unspecified phase)
0.6631 Remote Similarity NPD751 Clinical (unspecified phase)
0.6631 Remote Similarity NPD3813 Approved
0.6615 Remote Similarity NPD4239 Clinical (unspecified phase)
0.6614 Remote Similarity NPD4703 Approved
0.6614 Remote Similarity NPD4702 Approved
0.6606 Remote Similarity NPD8321 Discontinued
0.6606 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6603 Remote Similarity NPD6361 Phase 2
0.6588 Remote Similarity NPD6206 Phase 1
0.6587 Remote Similarity NPD1977 Clinical (unspecified phase)
0.6585 Remote Similarity NPD3082 Discontinued
0.6585 Remote Similarity NPD4889 Approved
0.6585 Remote Similarity NPD5075 Discontinued
0.6581 Remote Similarity NPD7576 Discontinued
0.6575 Remote Similarity NPD7470 Discontinued
0.6575 Remote Similarity NPD7927 Clinical (unspecified phase)
0.6574 Remote Similarity NPD7001 Phase 3
0.6573 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6567 Remote Similarity NPD5104 Approved
0.6561 Remote Similarity NPD5148 Clinical (unspecified phase)
0.6561 Remote Similarity NPD8112 Clinical (unspecified phase)
0.6561 Remote Similarity NPD7469 Discontinued
0.6561 Remote Similarity NPD5149 Phase 2
0.6558 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6542 Remote Similarity NPD7817 Phase 1
0.654 Remote Similarity NPD6226 Phase 3
0.6538 Remote Similarity NPD6281 Approved
0.6538 Remote Similarity NPD4081 Clinical (unspecified phase)
0.6538 Remote Similarity NPD1627 Clinical (unspecified phase)
0.6537 Remote Similarity NPD1096 Discontinued
0.6535 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6533 Remote Similarity NPD1573 Approved
0.6533 Remote Similarity NPD1575 Approved
0.653 Remote Similarity NPD6204 Clinical (unspecified phase)
0.652 Remote Similarity NPD3178 Discontinued
0.6517 Remote Similarity NPD482 Approved
0.6514 Remote Similarity NPD2509 Approved
0.6514 Remote Similarity NPD2510 Approved
0.6509 Remote Similarity NPD7807 Clinical (unspecified phase)
0.6507 Remote Similarity NPD3785 Clinical (unspecified phase)
0.65 Remote Similarity NPD485 Clinical (unspecified phase)
0.6498 Remote Similarity NPD7010 Phase 3
0.6497 Remote Similarity NPD1631 Approved
0.6496 Remote Similarity NPD6825 Phase 1
0.6495 Remote Similarity NPD4601 Approved
0.6495 Remote Similarity NPD4600 Approved
0.6495 Remote Similarity NPD5043 Discontinued
0.649 Remote Similarity NPD4334 Discontinued
0.649 Remote Similarity NPD6068 Discontinued
0.6488 Remote Similarity NPD5213 Clinical (unspecified phase)
0.6484 Remote Similarity NPD4520 Approved
0.6483 Remote Similarity NPD8412 Phase 1
0.6482 Remote Similarity NPD4640 Approved
0.6482 Remote Similarity NPD4638 Approved
0.6482 Remote Similarity NPD4639 Approved
0.6481 Remote Similarity NPD8072 Approved
0.6481 Remote Similarity NPD5487 Phase 1
0.6476 Remote Similarity NPD6753 Phase 1
0.6476 Remote Similarity NPD6752 Phase 1
0.6476 Remote Similarity NPD4376 Phase 3
0.6474 Remote Similarity NPD6148 Clinical (unspecified phase)
0.6473 Remote Similarity NPD4375 Approved
0.6473 Remote Similarity NPD6568 Discontinued
0.6471 Remote Similarity NPD7594 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