Structure

Physi-Chem Properties

Molecular Weight:  593.21
Volume:  568.716
LogP:  0.106
LogD:  -0.504
LogS:  -1.5
# Rotatable Bonds:  12
TPSA:  216.22
# H-Bond Aceptor:  14
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.11
Synthetic Accessibility Score:  5.533
Fsp3:  0.5
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:  -6.036
MDCK Permeability:  8.05947493063286e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.986
Human Intestinal Absorption (HIA):  0.984
20% Bioavailability (F20%):  0.17
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.151
Plasma Protein Binding (PPB):  23.308090209960938%
Volume Distribution (VD):  0.217
Pgp-substrate:  69.45625305175781%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.038
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.05
CYP2C9-inhibitor:  0.008
CYP2C9-substrate:  0.021
CYP2D6-inhibitor:  0.029
CYP2D6-substrate:  0.052
CYP3A4-inhibitor:  0.047
CYP3A4-substrate:  0.077

ADMET: Excretion

Clearance (CL):  1.592
Half-life (T1/2):  0.942

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.455
Drug-inuced Liver Injury (DILI):  0.987
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.061
Maximum Recommended Daily Dose:  0.067
Skin Sensitization:  0.061
Carcinogencity:  0.873
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.959

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

  Natural Product: NPC156044

Natural Product ID:  NPC156044
Common Name*:   Lonijaposide V
IUPAC Name:   (2S)-2-[3-carboxy-5-[(E)-2-[(2S,3R,4S)-3-ethenyl-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]ethenyl]pyridin-1-ium-1-yl]-3-methylbutanoate
Synonyms:  
Standard InCHIKey:  RMIHJDLBWBOJQK-MALFRZCUSA-N
Standard InCHI:  InChI=1S/C28H35NO13/c1-5-16-17(7-6-14-8-15(24(34)35)10-29(9-14)20(13(2)3)25(36)37)18(26(38)39-4)12-40-27(16)42-28-23(33)22(32)21(31)19(11-30)41-28/h5-10,12-13,16-17,19-23,27-28,30-33H,1,11H2,2-4H3,(H-,34,35,36,37)/b7-6+/t16-,17+,19-,20+,21-,22+,23-,27+,28+/m1/s1
SMILES:  C=C[C@H]1[C@@H](OC=C([C@H]1/C=C/c1c[n+](cc(c1)C(=O)O)[C@H](C(=O)[O-])C(C)C)C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3092669
PubChem CID:   76328128
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]
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[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]
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]
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]

☑ 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[524007]

☑ 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 NPC156044 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
0.9891 High Similarity NPC25442
0.9891 High Similarity NPC12944
0.9672 High Similarity NPC79223
0.9563 High Similarity NPC320748
0.9563 High Similarity NPC59033
0.9563 High Similarity NPC324245
0.9514 High Similarity NPC32451
0.9508 High Similarity NPC329024
0.9424 High Similarity NPC111732
0.9409 High Similarity NPC328559
0.9351 High Similarity NPC317672
0.8925 High Similarity NPC127647
0.8817 High Similarity NPC182814
0.8763 High Similarity NPC328798
0.8656 High Similarity NPC318020
0.8564 High Similarity NPC325775
0.8548 High Similarity NPC327373
0.8548 High Similarity NPC325093
0.8505 High Similarity NPC160127
0.8505 High Similarity NPC50997
0.849 Intermediate Similarity NPC20593
0.8351 Intermediate Similarity NPC322043
0.8342 Intermediate Similarity NPC309498
0.8053 Intermediate Similarity NPC317010
0.8039 Intermediate Similarity NPC472752
0.7895 Intermediate Similarity NPC477910
0.7837 Intermediate Similarity NPC472553
0.7837 Intermediate Similarity NPC476467
0.7778 Intermediate Similarity NPC472550
0.7778 Intermediate Similarity NPC304179
0.7778 Intermediate Similarity NPC48042
0.7773 Intermediate Similarity NPC471014
0.7773 Intermediate Similarity NPC475408
0.7736 Intermediate Similarity NPC144779
0.7736 Intermediate Similarity NPC294579
0.7729 Intermediate Similarity NPC63041
0.7725 Intermediate Similarity NPC470306
0.77 Intermediate Similarity NPC216428
0.77 Intermediate Similarity NPC472555
0.7689 Intermediate Similarity NPC6981
0.7689 Intermediate Similarity NPC471016
0.7678 Intermediate Similarity NPC319128
0.7678 Intermediate Similarity NPC228331
0.7674 Intermediate Similarity NPC477911
0.7667 Intermediate Similarity NPC292517
0.7653 Intermediate Similarity NPC62367
0.7628 Intermediate Similarity NPC477912
0.7617 Intermediate Similarity NPC84815
0.7617 Intermediate Similarity NPC301368
0.7615 Intermediate Similarity NPC124029
0.7615 Intermediate Similarity NPC211920
0.7606 Intermediate Similarity NPC206343
0.7606 Intermediate Similarity NPC477908
0.7606 Intermediate Similarity NPC162812
0.7604 Intermediate Similarity NPC473850
0.7604 Intermediate Similarity NPC475137
0.7604 Intermediate Similarity NPC233727
0.7604 Intermediate Similarity NPC475498
0.7604 Intermediate Similarity NPC477902
0.7588 Intermediate Similarity NPC75544
0.7569 Intermediate Similarity NPC148860
0.7569 Intermediate Similarity NPC473506
0.7559 Intermediate Similarity NPC42678
0.7559 Intermediate Similarity NPC477909
0.7559 Intermediate Similarity NPC477907
0.7559 Intermediate Similarity NPC30570
0.7558 Intermediate Similarity NPC471980
0.7558 Intermediate Similarity NPC76565
0.7558 Intermediate Similarity NPC57797
0.7558 Intermediate Similarity NPC250807
0.7547 Intermediate Similarity NPC165837
0.7527 Intermediate Similarity NPC263455
0.7523 Intermediate Similarity NPC328154
0.7512 Intermediate Similarity NPC127026
0.7512 Intermediate Similarity NPC127720
0.7512 Intermediate Similarity NPC264674
0.7511 Intermediate Similarity NPC477906
0.75 Intermediate Similarity NPC475644
0.75 Intermediate Similarity NPC475362
0.75 Intermediate Similarity NPC470486
0.75 Intermediate Similarity NPC280473
0.75 Intermediate Similarity NPC471977
0.75 Intermediate Similarity NPC323551
0.75 Intermediate Similarity NPC471190
0.7489 Intermediate Similarity NPC170751
0.7477 Intermediate Similarity NPC207531
0.7473 Intermediate Similarity NPC312860
0.7465 Intermediate Similarity NPC41724
0.7465 Intermediate Similarity NPC51008
0.7461 Intermediate Similarity NPC249614
0.7455 Intermediate Similarity NPC476110
0.7455 Intermediate Similarity NPC475600
0.7455 Intermediate Similarity NPC87152
0.7455 Intermediate Similarity NPC146824
0.7455 Intermediate Similarity NPC475631
0.7455 Intermediate Similarity NPC477787
0.7455 Intermediate Similarity NPC122968
0.7455 Intermediate Similarity NPC475601
0.7455 Intermediate Similarity NPC228377
0.7455 Intermediate Similarity NPC328186
0.7453 Intermediate Similarity NPC470189
0.7453 Intermediate Similarity NPC40919
0.7432 Intermediate Similarity NPC96801
0.7432 Intermediate Similarity NPC150698
0.743 Intermediate Similarity NPC4421
0.7416 Intermediate Similarity NPC289086
0.7413 Intermediate Similarity NPC44354
0.7407 Intermediate Similarity NPC319556
0.7399 Intermediate Similarity NPC469748
0.7399 Intermediate Similarity NPC30456
0.7395 Intermediate Similarity NPC193361
0.7395 Intermediate Similarity NPC62844
0.7393 Intermediate Similarity NPC470190
0.738 Intermediate Similarity NPC107287
0.7371 Intermediate Similarity NPC273532
0.7366 Intermediate Similarity NPC109922
0.7366 Intermediate Similarity NPC237702
0.7354 Intermediate Similarity NPC473689
0.7354 Intermediate Similarity NPC475303
0.7354 Intermediate Similarity NPC316841
0.7354 Intermediate Similarity NPC292416
0.7354 Intermediate Similarity NPC475596
0.7346 Intermediate Similarity NPC475835
0.7343 Intermediate Similarity NPC103361
0.7333 Intermediate Similarity NPC475426
0.7333 Intermediate Similarity NPC327769
0.7333 Intermediate Similarity NPC35208
0.7327 Intermediate Similarity NPC6576
0.7327 Intermediate Similarity NPC187494
0.7327 Intermediate Similarity NPC212768
0.7327 Intermediate Similarity NPC75600
0.7327 Intermediate Similarity NPC473089
0.7327 Intermediate Similarity NPC158020
0.7327 Intermediate Similarity NPC473115
0.7321 Intermediate Similarity NPC244839
0.7321 Intermediate Similarity NPC320324
0.7321 Intermediate Similarity NPC319880
0.7318 Intermediate Similarity NPC475271
0.7317 Intermediate Similarity NPC135950
0.7306 Intermediate Similarity NPC477903
0.7304 Intermediate Similarity NPC476090
0.7301 Intermediate Similarity NPC57453
0.7285 Intermediate Similarity NPC26881
0.7273 Intermediate Similarity NPC155792
0.7273 Intermediate Similarity NPC235364
0.7273 Intermediate Similarity NPC477788
0.726 Intermediate Similarity NPC477901
0.7257 Intermediate Similarity NPC475406
0.7256 Intermediate Similarity NPC244856
0.7255 Intermediate Similarity NPC114974
0.7225 Intermediate Similarity NPC38959
0.7225 Intermediate Similarity NPC327904
0.722 Intermediate Similarity NPC14116
0.722 Intermediate Similarity NPC285411
0.7214 Intermediate Similarity NPC207851
0.7212 Intermediate Similarity NPC238278
0.7207 Intermediate Similarity NPC477900
0.7207 Intermediate Similarity NPC477899
0.7205 Intermediate Similarity NPC253482
0.7189 Intermediate Similarity NPC274842
0.7188 Intermediate Similarity NPC134384
0.7188 Intermediate Similarity NPC311196
0.7177 Intermediate Similarity NPC123395
0.7169 Intermediate Similarity NPC82070
0.7166 Intermediate Similarity NPC112741
0.7156 Intermediate Similarity NPC91125
0.7151 Intermediate Similarity NPC167400
0.7143 Intermediate Similarity NPC306644
0.7143 Intermediate Similarity NPC236424
0.7131 Intermediate Similarity NPC478045
0.7124 Intermediate Similarity NPC475533
0.7112 Intermediate Similarity NPC475648
0.71 Intermediate Similarity NPC164340
0.7097 Intermediate Similarity NPC159630
0.7097 Intermediate Similarity NPC230085
0.7094 Intermediate Similarity NPC324619
0.7094 Intermediate Similarity NPC475315
0.7091 Intermediate Similarity NPC314270
0.7082 Intermediate Similarity NPC148896
0.7082 Intermediate Similarity NPC471013
0.7082 Intermediate Similarity NPC180668
0.7078 Intermediate Similarity NPC476114
0.7072 Intermediate Similarity NPC253314
0.7059 Intermediate Similarity NPC52254
0.7059 Intermediate Similarity NPC472435
0.7053 Intermediate Similarity NPC471546
0.7047 Intermediate Similarity NPC113812
0.7042 Intermediate Similarity NPC472436
0.7027 Intermediate Similarity NPC54066
0.7026 Intermediate Similarity NPC474217
0.7018 Intermediate Similarity NPC213143
0.7017 Intermediate Similarity NPC471015
0.6995 Remote Similarity NPC138018
0.6987 Remote Similarity NPC53255
0.6987 Remote Similarity NPC85879
0.6987 Remote Similarity NPC475301
0.6987 Remote Similarity NPC326930
0.6974 Remote Similarity NPC71079
0.6962 Remote Similarity NPC10904
0.6958 Remote Similarity NPC13603

  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 NPC156044 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
0.7931 Intermediate Similarity NPD7396 Approved
0.772 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.754 Intermediate Similarity NPD820 Phase 3
0.7361 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD8326 Phase 3
0.7361 Intermediate Similarity NPD8325 Phase 3
0.7348 Intermediate Similarity NPD8468 Phase 2
0.7166 Intermediate Similarity NPD9271 Approved
0.7151 Intermediate Similarity NPD9075 Approved
0.7151 Intermediate Similarity NPD9074 Approved
0.7116 Intermediate Similarity NPD6529 Discontinued
0.6986 Remote Similarity NPD3794 Approved
0.6986 Remote Similarity NPD3795 Approved
0.6951 Remote Similarity NPD8479 Phase 2
0.6947 Remote Similarity NPD5640 Discontinued
0.6935 Remote Similarity NPD107 Approved
0.693 Remote Similarity NPD2831 Approved
0.691 Remote Similarity NPD7885 Phase 2
0.691 Remote Similarity NPD7886 Phase 2
0.6905 Remote Similarity NPD5975 Clinical (unspecified phase)
0.6878 Remote Similarity NPD1096 Discontinued
0.6875 Remote Similarity NPD2544 Clinical (unspecified phase)
0.6875 Remote Similarity NPD8063 Discontinued
0.6863 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6853 Remote Similarity NPD5088 Discontinued
0.6844 Remote Similarity NPD6298 Discontinued
0.6842 Remote Similarity NPD4086 Phase 1
0.6824 Remote Similarity NPD8409 Suspended
0.681 Remote Similarity NPD6665 Discontinued
0.68 Remote Similarity NPD3280 Approved
0.6798 Remote Similarity NPD6641 Approved
0.6798 Remote Similarity NPD6642 Approved
0.6789 Remote Similarity NPD3371 Approved
0.6771 Remote Similarity NPD3389 Approved
0.6771 Remote Similarity NPD3394 Approved
0.6771 Remote Similarity NPD3393 Approved
0.6753 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6736 Remote Similarity NPD8370 Discontinued
0.6725 Remote Similarity NPD8289 Discontinued
0.6714 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6712 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6711 Remote Similarity NPD6578 Clinical (unspecified phase)
0.67 Remote Similarity NPD4174 Clinical (unspecified phase)
0.6697 Remote Similarity NPD3947 Discontinued
0.6696 Remote Similarity NPD4301 Approved
0.6682 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6682 Remote Similarity NPD2510 Approved
0.6682 Remote Similarity NPD2509 Approved
0.6682 Remote Similarity NPD1977 Clinical (unspecified phase)
0.6682 Remote Similarity NPD2336 Approved
0.6667 Remote Similarity NPD4417 Approved
0.6667 Remote Similarity NPD4989 Phase 2
0.6667 Remote Similarity NPD8356 Approved
0.6652 Remote Similarity NPD5148 Clinical (unspecified phase)
0.6652 Remote Similarity NPD5149 Phase 2
0.6651 Remote Similarity NPD4376 Phase 3
0.6651 Remote Similarity NPD2121 Clinical (unspecified phase)
0.665 Remote Similarity NPD1643 Phase 3
0.665 Remote Similarity NPD9510 Approved
0.6639 Remote Similarity NPD1483 Discontinued
0.6638 Remote Similarity NPD3006 Discontinued
0.6638 Remote Similarity NPD5891 Approved
0.662 Remote Similarity NPD4529 Approved
0.662 Remote Similarity NPD4528 Approved
0.662 Remote Similarity NPD4526 Approved
0.6612 Remote Similarity NPD8373 Clinical (unspecified phase)
0.6608 Remote Similarity NPD6770 Approved
0.659 Remote Similarity NPD4491 Clinical (unspecified phase)
0.6581 Remote Similarity NPD7031 Phase 1
0.6573 Remote Similarity NPD5317 Clinical (unspecified phase)
0.6564 Remote Similarity NPD7878 Phase 2
0.6561 Remote Similarity NPD203 Clinical (unspecified phase)
0.656 Remote Similarity NPD3911 Approved
0.6558 Remote Similarity NPD2307 Discontinued
0.6557 Remote Similarity NPD3321 Discontinued
0.6552 Remote Similarity NPD8430 Approved
0.6547 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6538 Remote Similarity NPD3178 Discontinued
0.6537 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6514 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6512 Remote Similarity NPD4427 Phase 2
0.6502 Remote Similarity NPD4506 Discontinued
0.6502 Remote Similarity NPD5583 Clinical (unspecified phase)
0.6498 Remote Similarity NPD53 Approved
0.6498 Remote Similarity NPD7778 Approved
0.6498 Remote Similarity NPD7777 Approved
0.6498 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6491 Remote Similarity NPD1623 Approved
0.6479 Remote Similarity NPD4081 Clinical (unspecified phase)
0.6478 Remote Similarity NPD4923 Phase 1
0.6475 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6473 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6471 Remote Similarity NPD4034 Approved
0.6471 Remote Similarity NPD4039 Approved
0.6471 Remote Similarity NPD4122 Approved
0.6471 Remote Similarity NPD31 Approved
0.6471 Remote Similarity NPD32 Approved
0.6471 Remote Similarity NPD4033 Approved
0.6471 Remote Similarity NPD4035 Approved
0.6471 Remote Similarity NPD4038 Approved
0.6471 Remote Similarity NPD4037 Approved
0.6471 Remote Similarity NPD4036 Approved
0.6465 Remote Similarity NPD1173 Approved
0.6462 Remote Similarity NPD9363 Approved
0.6462 Remote Similarity NPD9364 Phase 2
0.6457 Remote Similarity NPD7467 Discontinued
0.645 Remote Similarity NPD5255 Approved
0.6447 Remote Similarity NPD5965 Clinical (unspecified phase)
0.6444 Remote Similarity NPD5475 Discontinued
0.6444 Remote Similarity NPD6825 Phase 1
0.6442 Remote Similarity NPD8037 Clinical (unspecified phase)
0.6442 Remote Similarity NPD8036 Clinical (unspecified phase)
0.6441 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6435 Remote Similarity NPD1996 Discontinued
0.6432 Remote Similarity NPD4021 Phase 2
0.6432 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6426 Remote Similarity NPD5022 Discontinued
0.6418 Remote Similarity NPD2511 Approved
0.6416 Remote Similarity NPD5866 Approved
0.6416 Remote Similarity NPD7069 Discontinued
0.6406 Remote Similarity NPD1649 Discontinued
0.6402 Remote Similarity NPD4958 Clinical (unspecified phase)
0.64 Remote Similarity NPD9382 Approved
0.64 Remote Similarity NPD9383 Approved
0.64 Remote Similarity NPD2581 Approved
0.64 Remote Similarity NPD2582 Approved
0.6398 Remote Similarity NPD3569 Discontinued
0.6395 Remote Similarity NPD3925 Approved
0.6392 Remote Similarity NPD3813 Approved
0.6385 Remote Similarity NPD4948 Discontinued
0.6385 Remote Similarity NPD8021 Approved
0.6385 Remote Similarity NPD8020 Approved
0.6381 Remote Similarity NPD9362 Approved
0.6379 Remote Similarity NPD7967 Discontinued
0.6373 Remote Similarity NPD4805 Approved
0.6372 Remote Similarity NPD7470 Discontinued
0.6368 Remote Similarity NPD7010 Phase 3
0.6368 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6368 Remote Similarity NPD7426 Phase 1
0.6367 Remote Similarity NPD6351 Discovery
0.6364 Remote Similarity NPD4501 Approved
0.6364 Remote Similarity NPD4500 Approved
0.6355 Remote Similarity NPD7233 Approved
0.6355 Remote Similarity NPD7234 Approved
0.6352 Remote Similarity NPD8375 Approved
0.6348 Remote Similarity NPD1926 Approved
0.6341 Remote Similarity NPD6872 Clinical (unspecified phase)
0.6335 Remote Similarity NPD9506 Approved
0.6323 Remote Similarity NPD4906 Approved
0.6323 Remote Similarity NPD4905 Approved
0.6323 Remote Similarity NPD4903 Approved
0.6322 Remote Similarity NPD7576 Discontinued
0.632 Remote Similarity NPD7404 Approved
0.6318 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6313 Remote Similarity NPD4551 Phase 2
0.6313 Remote Similarity NPD6361 Phase 2
0.6308 Remote Similarity NPD751 Clinical (unspecified phase)
0.6304 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6304 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6302 Remote Similarity NPD2896 Discontinued
0.6301 Remote Similarity NPD8371 Clinical (unspecified phase)
0.63 Remote Similarity NPD3779 Clinical (unspecified phase)
0.6296 Remote Similarity NPD6716 Phase 1
0.6295 Remote Similarity NPD7001 Phase 3
0.6295 Remote Similarity NPD4904 Approved
0.6295 Remote Similarity NPD7289 Clinical (unspecified phase)
0.6294 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6291 Remote Similarity NPD4889 Approved
0.629 Remote Similarity NPD5228 Phase 3
0.6287 Remote Similarity NPD5801 Clinical (unspecified phase)
0.6282 Remote Similarity NPD6173 Approved
0.6281 Remote Similarity NPD510 Phase 1
0.628 Remote Similarity NPD6739 Clinical (unspecified phase)
0.6279 Remote Similarity NPD6068 Discontinued
0.6278 Remote Similarity NPD5513 Phase 2
0.6276 Remote Similarity NPD4373 Phase 2
0.6275 Remote Similarity NPD5482 Discontinued
0.6272 Remote Similarity NPD3917 Approved
0.6272 Remote Similarity NPD3918 Approved
0.6272 Remote Similarity NPD3916 Clinical (unspecified phase)
0.6269 Remote Similarity NPD4804 Approved
0.6267 Remote Similarity NPD981 Phase 2
0.6267 Remote Similarity NPD7562 Approved
0.6267 Remote Similarity NPD6569 Phase 2
0.6262 Remote Similarity NPD4375 Approved
0.6261 Remote Similarity NPD5490 Discontinued
0.626 Remote Similarity NPD6276 Discontinued
0.6256 Remote Similarity NPD5897 Approved
0.6256 Remote Similarity NPD5899 Approved
0.6256 Remote Similarity NPD5898 Approved
0.6256 Remote Similarity NPD9398 Clinical (unspecified phase)
0.625 Remote Similarity NPD7712 Clinical (unspecified phase)
0.625 Remote Similarity NPD5316 Approved
0.625 Remote Similarity NPD6987 Phase 1
0.625 Remote Similarity NPD5901 Discontinued
0.625 Remote Similarity NPD6955 Clinical (unspecified phase)
0.625 Remote Similarity NPD944 Approved
0.6233 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6228 Remote Similarity NPD7927 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