Structure

Physi-Chem Properties

Molecular Weight:  593.23
Volume:  589.144
LogP:  2.402
LogD:  1.395
LogS:  -3.945
# Rotatable Bonds:  10
TPSA:  158.55
# H-Bond Aceptor:  11
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.276
Synthetic Accessibility Score:  5.899
Fsp3:  0.469
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:  -5.306
MDCK Permeability:  1.9827388314297423e-05
Pgp-inhibitor:  0.995
Pgp-substrate:  0.762
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.946
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.88
Plasma Protein Binding (PPB):  67.95472717285156%
Volume Distribution (VD):  1.152
Pgp-substrate:  26.67736053466797%

ADMET: Metabolism

CYP1A2-inhibitor:  0.071
CYP1A2-substrate:  0.116
CYP2C19-inhibitor:  0.062
CYP2C19-substrate:  0.093
CYP2C9-inhibitor:  0.386
CYP2C9-substrate:  0.053
CYP2D6-inhibitor:  0.059
CYP2D6-substrate:  0.062
CYP3A4-inhibitor:  0.831
CYP3A4-substrate:  0.367

ADMET: Excretion

Clearance (CL):  6.35
Half-life (T1/2):  0.093

ADMET: Toxicity

hERG Blockers:  0.37
Human Hepatotoxicity (H-HT):  0.326
Drug-inuced Liver Injury (DILI):  0.975
AMES Toxicity:  0.679
Rat Oral Acute Toxicity:  0.879
Maximum Recommended Daily Dose:  0.384
Skin Sensitization:  0.438
Carcinogencity:  0.682
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.983

Download Data

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

  Natural Product: NPC150698

Natural Product ID:  NPC150698
Common Name*:   Triptersinin A
IUPAC Name:   n.a.
Synonyms:   Triptersinin A
Standard InCHIKey:  BBRQXPPJMGLPCU-RTTFQUHKSA-N
Standard InCHI:  InChI=1S/C32H35NO10/c1-19(34)40-18-31-22(41-23(35)13-12-20-9-6-5-7-10-20)14-15-30(4,39)32(31)26(37)24(29(2,3)43-32)25(36)27(31)42-28(38)21-11-8-16-33-17-21/h5-13,16-17,22,24,26-27,37,39H,14-15,18H2,1-4H3/b13-12+/t22-,24+,26+,27+,30-,31-,32-/m0/s1
SMILES:  O=C(O[C@H]1CC[C@]([C@@]23[C@]1(COC(=O)C)[C@H](OC(=O)c1cccnc1)C(=O)[C@H]([C@H]3O)C(O2)(C)C)(C)O)/C=C/c1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2335690
PubChem CID:   71524354
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0002051] Agarofurans

*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
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(90)85349-K]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. DOI[10.1186/1471-2202-6-1]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10579865]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[10716597]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10757718]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11374948]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11561442]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[12579877]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[16864458]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota roots n.a. n.a. PMID[16989518]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[17250858]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[17265278]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[18554602]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[18996177]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota root n.a. n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[21514608]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota dried roots purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China) n.a. PMID[22148431]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota leaves n.a. n.a. PMID[23268606]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[23852638]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24549173]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24963543]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[25237706]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[2534610]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[2816380]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[29355322]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[31556299]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7102323]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7304185]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8699928]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8722541]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13661 Tripterygium wilfordii Species Celastraceae 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
NPT179 Cell Line A2780 Homo sapiens IC50 > 1000.0 nM PMID[491880]
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 1000.0 nM PMID[491880]
NPT547 Cell Line BGC-823 Homo sapiens IC50 > 1000.0 nM PMID[491880]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 1000.0 nM PMID[491880]
NPT81 Cell Line A549 Homo sapiens IC50 > 1000.0 nM PMID[491880]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 47.3 % PMID[491880]

☑ 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 NPC150698 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 NPC96801
0.9756 High Similarity NPC475601
0.966 High Similarity NPC211920
0.9659 High Similarity NPC328154
0.9575 High Similarity NPC253482
0.9569 High Similarity NPC469748
0.9565 High Similarity NPC124029
0.951 High Similarity NPC84815
0.951 High Similarity NPC301368
0.9479 High Similarity NPC35208
0.9469 High Similarity NPC477902
0.9461 High Similarity NPC294579
0.9461 High Similarity NPC144779
0.9442 High Similarity NPC475648
0.942 High Similarity NPC471980
0.9412 High Similarity NPC6981
0.9372 High Similarity NPC127026
0.9372 High Similarity NPC127720
0.934 High Similarity NPC237702
0.9336 High Similarity NPC477906
0.9324 High Similarity NPC477912
0.9317 High Similarity NPC471014
0.9317 High Similarity NPC471016
0.9317 High Similarity NPC475408
0.9314 High Similarity NPC4421
0.9292 High Similarity NPC244839
0.9292 High Similarity NPC319880
0.9292 High Similarity NPC320324
0.9272 High Similarity NPC62367
0.9268 High Similarity NPC470306
0.9245 High Similarity NPC292416
0.9245 High Similarity NPC473689
0.9242 High Similarity NPC471190
0.9242 High Similarity NPC475644
0.9242 High Similarity NPC471977
0.9242 High Similarity NPC470486
0.9238 High Similarity NPC148860
0.9231 High Similarity NPC477903
0.9227 High Similarity NPC216428
0.9194 High Similarity NPC475600
0.9194 High Similarity NPC475631
0.9194 High Similarity NPC328186
0.9194 High Similarity NPC228377
0.9194 High Similarity NPC87152
0.9194 High Similarity NPC122968
0.9194 High Similarity NPC476110
0.9194 High Similarity NPC477787
0.9179 High Similarity NPC158020
0.9179 High Similarity NPC6576
0.9179 High Similarity NPC212768
0.9179 High Similarity NPC473089
0.9179 High Similarity NPC473115
0.9179 High Similarity NPC75600
0.9175 High Similarity NPC477907
0.9175 High Similarity NPC477909
0.9175 High Similarity NPC42678
0.9163 High Similarity NPC327904
0.9163 High Similarity NPC38959
0.9151 High Similarity NPC475362
0.9147 High Similarity NPC473506
0.9126 High Similarity NPC319128
0.9126 High Similarity NPC228331
0.9126 High Similarity NPC264674
0.9116 High Similarity NPC475406
0.9116 High Similarity NPC475426
0.9112 High Similarity NPC30456
0.9104 High Similarity NPC146824
0.91 High Similarity NPC475137
0.91 High Similarity NPC473850
0.91 High Similarity NPC475498
0.91 High Similarity NPC26881
0.9082 High Similarity NPC477910
0.907 High Similarity NPC238278
0.9065 High Similarity NPC475596
0.9065 High Similarity NPC316841
0.9065 High Similarity NPC475303
0.9052 High Similarity NPC250807
0.9052 High Similarity NPC76565
0.9052 High Similarity NPC57797
0.9029 High Similarity NPC472553
0.9023 High Similarity NPC213143
0.9009 High Similarity NPC477899
0.9009 High Similarity NPC477900
0.9005 High Similarity NPC477911
0.9005 High Similarity NPC477788
0.9005 High Similarity NPC235364
0.8972 High Similarity NPC311196
0.8972 High Similarity NPC134384
0.8952 High Similarity NPC472555
0.894 High Similarity NPC327769
0.893 High Similarity NPC91125
0.8925 High Similarity NPC14116
0.8925 High Similarity NPC285411
0.892 High Similarity NPC233727
0.891 High Similarity NPC477901
0.8883 High Similarity NPC48042
0.8883 High Similarity NPC472550
0.8883 High Similarity NPC304179
0.8857 High Similarity NPC477908
0.8857 High Similarity NPC206343
0.8853 High Similarity NPC170751
0.8835 High Similarity NPC63041
0.8795 High Similarity NPC324619
0.8795 High Similarity NPC475315
0.8792 High Similarity NPC472752
0.8767 High Similarity NPC471015
0.875 High Similarity NPC475533
0.8739 High Similarity NPC473833
0.8726 High Similarity NPC187494
0.8632 High Similarity NPC30570
0.8578 High Similarity NPC476467
0.8565 High Similarity NPC475301
0.8565 High Similarity NPC85879
0.8565 High Similarity NPC326930
0.8565 High Similarity NPC53255
0.854 High Similarity NPC148896
0.854 High Similarity NPC180668
0.854 High Similarity NPC471013
0.8531 High Similarity NPC40919
0.8531 High Similarity NPC470189
0.8528 High Similarity NPC13603
0.8504 High Similarity NPC471978
0.8491 Intermediate Similarity NPC292517
0.8476 Intermediate Similarity NPC470190
0.8465 Intermediate Similarity NPC319556
0.8458 Intermediate Similarity NPC62844
0.8458 Intermediate Similarity NPC193361
0.8426 Intermediate Similarity NPC328928
0.8419 Intermediate Similarity NPC162812
0.8391 Intermediate Similarity NPC10904
0.8372 Intermediate Similarity NPC207531
0.8319 Intermediate Similarity NPC471979
0.8318 Intermediate Similarity NPC323551
0.8318 Intermediate Similarity NPC280473
0.8279 Intermediate Similarity NPC41724
0.8279 Intermediate Similarity NPC51008
0.8246 Intermediate Similarity NPC289086
0.81 Intermediate Similarity NPC253314
0.8084 Intermediate Similarity NPC475835
0.8028 Intermediate Similarity NPC165837
0.7983 Intermediate Similarity NPC476090
0.7972 Intermediate Similarity NPC470279
0.787 Intermediate Similarity NPC309498
0.786 Intermediate Similarity NPC471004
0.7857 Intermediate Similarity NPC103230
0.7658 Intermediate Similarity NPC111732
0.7628 Intermediate Similarity NPC324245
0.7628 Intermediate Similarity NPC320748
0.7604 Intermediate Similarity NPC328559
0.7604 Intermediate Similarity NPC155792
0.7604 Intermediate Similarity NPC32451
0.7594 Intermediate Similarity NPC275170
0.7594 Intermediate Similarity NPC306001
0.7594 Intermediate Similarity NPC473400
0.7594 Intermediate Similarity NPC206211
0.7594 Intermediate Similarity NPC471629
0.7594 Intermediate Similarity NPC324251
0.7559 Intermediate Similarity NPC67246
0.7559 Intermediate Similarity NPC33372
0.7558 Intermediate Similarity NPC79223
0.7512 Intermediate Similarity NPC453583
0.7512 Intermediate Similarity NPC473300
0.7512 Intermediate Similarity NPC471754
0.7512 Intermediate Similarity NPC475336
0.7512 Intermediate Similarity NPC317882
0.75 Intermediate Similarity NPC107123
0.75 Intermediate Similarity NPC329024
0.75 Intermediate Similarity NPC181964
0.75 Intermediate Similarity NPC471997
0.75 Intermediate Similarity NPC208553
0.75 Intermediate Similarity NPC471606
0.7465 Intermediate Similarity NPC473558
0.7454 Intermediate Similarity NPC321072
0.7454 Intermediate Similarity NPC215892
0.7454 Intermediate Similarity NPC191193
0.7454 Intermediate Similarity NPC242662
0.7446 Intermediate Similarity NPC235885
0.7446 Intermediate Similarity NPC141428
0.7432 Intermediate Similarity NPC156044
0.7407 Intermediate Similarity NPC476516
0.7406 Intermediate Similarity NPC37473
0.7385 Intermediate Similarity NPC317672
0.7385 Intermediate Similarity NPC59033
0.7385 Intermediate Similarity NPC473490
0.7383 Intermediate Similarity NPC471623
0.7382 Intermediate Similarity NPC57690
0.7373 Intermediate Similarity NPC109922
0.7364 Intermediate Similarity NPC472391
0.7342 Intermediate Similarity NPC25442
0.7342 Intermediate Similarity NPC12944
0.7342 Intermediate Similarity NPC116862
0.7339 Intermediate Similarity NPC36607
0.7336 Intermediate Similarity NPC44354
0.7336 Intermediate Similarity NPC141385
0.7318 Intermediate Similarity NPC472375
0.7318 Intermediate Similarity NPC472392
0.7297 Intermediate Similarity NPC289383
0.7287 Intermediate Similarity NPC478045
0.7285 Intermediate Similarity NPC176371
0.7285 Intermediate Similarity NPC136573

  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 NPC150698 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
0.8182 Intermediate Similarity NPD8468 Phase 2
0.7794 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD7396 Approved
0.7534 Intermediate Similarity NPD7927 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD8485 Approved
0.7448 Intermediate Similarity NPD1483 Discontinued
0.7407 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD8435 Approved
0.7368 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD8326 Phase 3
0.7368 Intermediate Similarity NPD8325 Phase 3
0.7313 Intermediate Similarity NPD3795 Approved
0.7313 Intermediate Similarity NPD3794 Approved
0.7302 Intermediate Similarity NPD8360 Approved
0.7302 Intermediate Similarity NPD8361 Approved
0.7149 Intermediate Similarity NPD7885 Phase 2
0.7149 Intermediate Similarity NPD7886 Phase 2
0.713 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD820 Phase 3
0.7103 Intermediate Similarity NPD7708 Approved
0.7098 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD5891 Approved
0.7072 Intermediate Similarity NPD7778 Approved
0.7072 Intermediate Similarity NPD7777 Approved
0.7072 Intermediate Similarity NPD53 Approved
0.7059 Intermediate Similarity NPD7803 Approved
0.7056 Intermediate Similarity NPD7707 Approved
0.7056 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD7878 Phase 2
0.7037 Intermediate Similarity NPD8407 Phase 2
0.7035 Intermediate Similarity NPD6987 Phase 1
0.7018 Intermediate Similarity NPD7234 Approved
0.7018 Intermediate Similarity NPD7233 Approved
0.7004 Intermediate Similarity NPD7010 Phase 3
0.6987 Remote Similarity NPD6529 Discontinued
0.6979 Remote Similarity NPD3280 Approved
0.6971 Remote Similarity NPD6635 Approved
0.6971 Remote Similarity NPD5088 Discontinued
0.697 Remote Similarity NPD7069 Discontinued
0.6964 Remote Similarity NPD6661 Clinical (unspecified phase)
0.696 Remote Similarity NPD3947 Discontinued
0.6953 Remote Similarity NPD3393 Approved
0.6953 Remote Similarity NPD3394 Approved
0.6953 Remote Similarity NPD3389 Approved
0.6926 Remote Similarity NPD8409 Suspended
0.6923 Remote Similarity NPD4989 Phase 2
0.6916 Remote Similarity NPD6642 Approved
0.6916 Remote Similarity NPD6641 Approved
0.6898 Remote Similarity NPD8368 Discontinued
0.6888 Remote Similarity NPD5801 Clinical (unspecified phase)
0.6887 Remote Similarity NPD485 Clinical (unspecified phase)
0.6886 Remote Similarity NPD2831 Approved
0.6878 Remote Similarity NPD2336 Approved
0.6872 Remote Similarity NPD6477 Clinical (unspecified phase)
0.687 Remote Similarity NPD2510 Approved
0.687 Remote Similarity NPD2509 Approved
0.6863 Remote Similarity NPD7955 Approved
0.6863 Remote Similarity NPD7956 Approved
0.686 Remote Similarity NPD8372 Clinical (unspecified phase)
0.686 Remote Similarity NPD6962 Phase 2
0.6853 Remote Similarity NPD4417 Approved
0.684 Remote Similarity NPD4506 Discontinued
0.6837 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6835 Remote Similarity NPD8479 Phase 2
0.6824 Remote Similarity NPD8462 Phase 1
0.6807 Remote Similarity NPD4301 Approved
0.6803 Remote Similarity NPD4373 Phase 2
0.6793 Remote Similarity NPD6770 Approved
0.6792 Remote Similarity NPD3925 Approved
0.6783 Remote Similarity NPD4901 Clinical (unspecified phase)
0.678 Remote Similarity NPD8404 Phase 2
0.6769 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6765 Remote Similarity NPD9271 Approved
0.6757 Remote Similarity NPD8063 Discontinued
0.6756 Remote Similarity NPD2307 Discontinued
0.6752 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6026 Approved
0.6714 Remote Similarity NPD2511 Approved
0.6709 Remote Similarity NPD5475 Discontinued
0.6696 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6693 Remote Similarity NPD8091 Phase 3
0.6692 Remote Similarity NPD8467 Approved
0.6692 Remote Similarity NPD8465 Approved
0.6692 Remote Similarity NPD8466 Approved
0.6682 Remote Similarity NPD8470 Clinical (unspecified phase)
0.668 Remote Similarity NPD8350 Clinical (unspecified phase)
0.668 Remote Similarity NPD7862 Clinical (unspecified phase)
0.668 Remote Similarity NPD4952 Phase 3
0.6667 Remote Similarity NPD6323 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6791 Phase 2
0.6667 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6654 Remote Similarity NPD8373 Clinical (unspecified phase)
0.6641 Remote Similarity NPD8370 Discontinued
0.664 Remote Similarity NPD6790 Phase 1
0.6639 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6637 Remote Similarity NPD4427 Phase 2
0.6622 Remote Similarity NPD4376 Phase 3
0.6611 Remote Similarity NPD1926 Approved
0.6598 Remote Similarity NPD4086 Phase 1
0.6596 Remote Similarity NPD6262 Clinical (unspecified phase)
0.6593 Remote Similarity NPD8426 Approved
0.6593 Remote Similarity NPD8425 Approved
0.6593 Remote Similarity NPD6361 Phase 2
0.6593 Remote Similarity NPD8459 Approved
0.6593 Remote Similarity NPD8460 Approved
0.6585 Remote Similarity NPD9075 Approved
0.6585 Remote Similarity NPD9074 Approved
0.658 Remote Similarity NPD7187 Phase 2
0.6574 Remote Similarity NPD6739 Clinical (unspecified phase)
0.6574 Remote Similarity NPD7417 Discontinued
0.6573 Remote Similarity NPD7807 Clinical (unspecified phase)
0.657 Remote Similarity NPD8356 Approved
0.6569 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6567 Remote Similarity NPD8428 Approved
0.6567 Remote Similarity NPD8429 Approved
0.6567 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6567 Remote Similarity NPD8427 Approved
0.6565 Remote Similarity NPD4601 Approved
0.6565 Remote Similarity NPD4600 Approved
0.6557 Remote Similarity NPD5640 Discontinued
0.6557 Remote Similarity NPD8289 Discontinued
0.6546 Remote Similarity NPD3006 Discontinued
0.6545 Remote Similarity NPD5022 Discontinued
0.6545 Remote Similarity NPD8052 Clinical (unspecified phase)
0.654 Remote Similarity NPD5866 Approved
0.6535 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6524 Remote Similarity NPD5901 Discontinued
0.6518 Remote Similarity NPD4948 Discontinued
0.6518 Remote Similarity NPD6257 Clinical (unspecified phase)
0.6515 Remote Similarity NPD7404 Approved
0.6511 Remote Similarity NPD7947 Clinical (unspecified phase)
0.6507 Remote Similarity NPD6206 Phase 1
0.6507 Remote Similarity NPD5003 Discontinued
0.6506 Remote Similarity NPD8329 Phase 3
0.6498 Remote Similarity NPD7470 Discontinued
0.6496 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6496 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6496 Remote Similarity NPD7957 Phase 1
0.6494 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6494 Remote Similarity NPD6825 Phase 1
0.6485 Remote Similarity NPD4897 Phase 2
0.6485 Remote Similarity NPD8112 Clinical (unspecified phase)
0.6482 Remote Similarity NPD8412 Phase 1
0.6482 Remote Similarity NPD6716 Phase 1
0.6473 Remote Similarity NPD7395 Discontinued
0.6471 Remote Similarity NPD107 Approved
0.6468 Remote Similarity NPD7562 Approved
0.6466 Remote Similarity NPD8363 Approved
0.6466 Remote Similarity NPD8364 Approved
0.6463 Remote Similarity NPD8430 Approved
0.6461 Remote Similarity NPD5506 Approved
0.6461 Remote Similarity NPD5507 Approved
0.646 Remote Similarity NPD6281 Approved
0.6459 Remote Similarity NPD5482 Discontinued
0.6458 Remote Similarity NPD5490 Discontinued
0.6456 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6444 Remote Similarity NPD8020 Approved
0.6444 Remote Similarity NPD8150 Discontinued
0.6444 Remote Similarity NPD8021 Approved
0.6443 Remote Similarity NPD7576 Discontinued
0.6441 Remote Similarity NPD7414 Clinical (unspecified phase)
0.6435 Remote Similarity NPD6446 Discontinued
0.6434 Remote Similarity NPD6995 Phase 1
0.6432 Remote Similarity NPD3785 Clinical (unspecified phase)
0.6431 Remote Similarity NPD7967 Discontinued
0.6429 Remote Similarity NPD4889 Approved
0.6423 Remote Similarity NPD7426 Phase 1
0.6422 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6418 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6417 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6413 Remote Similarity NPD7962 Phase 2
0.6404 Remote Similarity NPD4950 Approved
0.6404 Remote Similarity NPD6665 Discontinued
0.6396 Remote Similarity NPD5899 Approved
0.6396 Remote Similarity NPD5897 Approved
0.6396 Remote Similarity NPD5898 Approved
0.6393 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6393 Remote Similarity NPD5147 Discontinued
0.6393 Remote Similarity NPD6298 Discontinued
0.6391 Remote Similarity NPD6226 Phase 3
0.6389 Remote Similarity NPD5805 Approved
0.6386 Remote Similarity NPD7688 Phase 1
0.6384 Remote Similarity NPD3217 Phase 2
0.6383 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6383 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6382 Remote Similarity NPD7269 Clinical (unspecified phase)
0.6381 Remote Similarity NPD6276 Discontinued
0.6379 Remote Similarity NPD6874 Approved
0.6379 Remote Similarity NPD6955 Clinical (unspecified phase)
0.6376 Remote Similarity NPD4526 Approved
0.6376 Remote Similarity NPD4529 Approved
0.6376 Remote Similarity NPD4528 Approved
0.6375 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6374 Remote Similarity NPD8461 Discontinued
0.6373 Remote Similarity NPD2896 Discontinued
0.6371 Remote Similarity NPD7191 Phase 2
0.6367 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6364 Remote Similarity NPD1270 Approved
0.6352 Remote Similarity NPD4500 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