Structure

Physi-Chem Properties

Molecular Weight:  987.32
Volume:  952.806
LogP:  2.897
LogD:  1.474
LogS:  -3.704
# Rotatable Bonds:  17
TPSA:  279.05
# H-Bond Aceptor:  21
# H-Bond Donor:  1
# Rings:  7
# Heavy Atoms:  21

MedChem Properties

QED Drug-Likeness Score:  0.226
Synthetic Accessibility Score:  7.779
Fsp3:  0.48
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:  -5.226
MDCK Permeability:  0.00010545217810431495
Pgp-inhibitor:  1.0
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.741
20% Bioavailability (F20%):  0.999
30% Bioavailability (F30%):  0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.044
Plasma Protein Binding (PPB):  56.42869186401367%
Volume Distribution (VD):  1.67
Pgp-substrate:  10.537884712219238%

ADMET: Metabolism

CYP1A2-inhibitor:  0.152
CYP1A2-substrate:  0.01
CYP2C19-inhibitor:  0.111
CYP2C19-substrate:  0.049
CYP2C9-inhibitor:  0.182
CYP2C9-substrate:  0.005
CYP2D6-inhibitor:  0.991
CYP2D6-substrate:  0.021
CYP3A4-inhibitor:  0.823
CYP3A4-substrate:  0.248

ADMET: Excretion

Clearance (CL):  3.176
Half-life (T1/2):  0.605

ADMET: Toxicity

hERG Blockers:  0.111
Human Hepatotoxicity (H-HT):  0.975
Drug-inuced Liver Injury (DILI):  0.984
AMES Toxicity:  0.026
Rat Oral Acute Toxicity:  0.074
Maximum Recommended Daily Dose:  0.007
Skin Sensitization:  0.332
Carcinogencity:  0.06
Eye Corrosion:  0.003
Eye Irritation:  0.043
Respiratory Toxicity:  0.014

Download Data

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

  Natural Product: NPC38959

Natural Product ID:  NPC38959
Common Name*:   Wilfornine C
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  WTRGNKRBOZTZCU-PYMTWWKESA-N
Standard InCHI:  InChI=1S/C50H53NO20/c1-26(52)62-25-49-40(66-29(4)55)36(64-27(2)53)35-38(68-42(57)31-16-11-9-12-17-31)50(49)48(8,61)39(37(65-28(3)54)41(49)67-30(5)56)69-45(60)46(6,70-43(58)32-18-13-10-14-19-32)22-21-34-33(20-15-23-51-34)44(59)63-24-47(35,7)71-50/h9-20,23,35-41,61H,21-22,24-25H2,1-8H3/t35-,36-,37+,38-,39+,40-,41+,46-,47+,48+,49-,50+/m1/s1
SMILES:  CC(=O)OC[C@]12[C@@H](OC(=O)C)[C@@H](OC(=O)C)[C@H]3[C@]([C@@]42O[C@@]([C@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)[C@H]4OC(=O)c1ccccc1)(C)COC(=O)c1cccnc1CC[C@@](C(=O)O3)(C)OC(=O)c1ccccc1)(C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL509162
PubChem CID:   44584749
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones

*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. n.a. n.a. PMID[1375626]
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[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. leaf n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root 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
NPT927 Cell Line PBMC Homo sapiens Inhibition = -11.0 % PMID[486071]
NPT927 Cell Line PBMC Homo sapiens Inhibition = -6.0 % PMID[486071]
NPT927 Cell Line PBMC Homo sapiens Inhibition = -8.0 % PMID[486071]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 51.0 % PMID[486071]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 39.0 % PMID[486071]
NPT927 Cell Line PBMC Homo sapiens Inhibition = 32.0 % PMID[486071]

☑ 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 NPC38959 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 NPC327904
0.9952 High Similarity NPC475406
0.9856 High Similarity NPC319880
0.9856 High Similarity NPC320324
0.9856 High Similarity NPC244839
0.9809 High Similarity NPC237702
0.9808 High Similarity NPC292416
0.9808 High Similarity NPC473689
0.9808 High Similarity NPC316841
0.972 High Similarity NPC475648
0.9713 High Similarity NPC475596
0.9713 High Similarity NPC475303
0.9667 High Similarity NPC30456
0.9663 High Similarity NPC228377
0.9663 High Similarity NPC122968
0.9663 High Similarity NPC146824
0.9663 High Similarity NPC477787
0.9663 High Similarity NPC328186
0.9617 High Similarity NPC475362
0.9579 High Similarity NPC253482
0.9569 High Similarity NPC476110
0.9569 High Similarity NPC475631
0.9569 High Similarity NPC475600
0.9569 High Similarity NPC87152
0.9524 High Similarity NPC471190
0.9524 High Similarity NPC470486
0.9524 High Similarity NPC471977
0.9524 High Similarity NPC475644
0.9519 High Similarity NPC57797
0.9519 High Similarity NPC250807
0.9484 High Similarity NPC327769
0.9474 High Similarity NPC473850
0.9471 High Similarity NPC127026
0.9471 High Similarity NPC477788
0.9471 High Similarity NPC127720
0.9429 High Similarity NPC473506
0.9426 High Similarity NPC471980
0.9426 High Similarity NPC76565
0.9381 High Similarity NPC475137
0.9381 High Similarity NPC475498
0.9381 High Similarity NPC328154
0.9327 High Similarity NPC84815
0.9327 High Similarity NPC301368
0.9302 High Similarity NPC35208
0.9279 High Similarity NPC212768
0.9279 High Similarity NPC75600
0.9279 High Similarity NPC473115
0.9279 High Similarity NPC473089
0.9279 High Similarity NPC158020
0.9279 High Similarity NPC6576
0.9231 High Similarity NPC471016
0.9231 High Similarity NPC6981
0.9187 High Similarity NPC144779
0.9187 High Similarity NPC294579
0.9183 High Similarity NPC470306
0.9163 High Similarity NPC96801
0.9163 High Similarity NPC150698
0.9147 High Similarity NPC477912
0.9139 High Similarity NPC471014
0.9139 High Similarity NPC475408
0.9135 High Similarity NPC4421
0.9124 High Similarity NPC170751
0.9112 High Similarity NPC475601
0.9095 High Similarity NPC62367
0.9065 High Similarity NPC148860
0.9052 High Similarity NPC216428
0.9037 High Similarity NPC475426
0.9023 High Similarity NPC211920
0.9019 High Similarity NPC477902
0.9 High Similarity NPC42678
0.9 High Similarity NPC477907
0.9 High Similarity NPC477909
0.8967 High Similarity NPC477903
0.8952 High Similarity NPC319128
0.8935 High Similarity NPC124029
0.8865 High Similarity NPC13603
0.8863 High Similarity NPC228331
0.8858 High Similarity NPC469748
0.8857 High Similarity NPC472553
0.8837 High Similarity NPC477911
0.8821 High Similarity NPC477910
0.8821 High Similarity NPC53255
0.8821 High Similarity NPC85879
0.8785 High Similarity NPC472555
0.8756 High Similarity NPC477899
0.8756 High Similarity NPC477900
0.8739 High Similarity NPC326930
0.8739 High Similarity NPC475301
0.8727 High Similarity NPC477906
0.8714 High Similarity NPC472550
0.8714 High Similarity NPC48042
0.8714 High Similarity NPC304179
0.8692 High Similarity NPC477908
0.8692 High Similarity NPC206343
0.8685 High Similarity NPC264674
0.8675 High Similarity NPC328928
0.8675 High Similarity NPC471978
0.8664 High Similarity NPC235364
0.8644 High Similarity NPC471979
0.859 High Similarity NPC473833
0.8584 High Similarity NPC26881
0.8578 High Similarity NPC63041
0.8571 High Similarity NPC477901
0.8515 High Similarity NPC475533
0.8514 High Similarity NPC91125
0.8478 Intermediate Similarity NPC475315
0.8478 Intermediate Similarity NPC324619
0.8468 Intermediate Similarity NPC134384
0.8468 Intermediate Similarity NPC311196
0.8423 Intermediate Similarity NPC285411
0.8423 Intermediate Similarity NPC14116
0.84 Intermediate Similarity NPC238278
0.8356 Intermediate Similarity NPC213143
0.8333 Intermediate Similarity NPC476467
0.8279 Intermediate Similarity NPC472752
0.8251 Intermediate Similarity NPC233727
0.8233 Intermediate Similarity NPC476090
0.822 Intermediate Similarity NPC471015
0.8165 Intermediate Similarity NPC323551
0.8165 Intermediate Similarity NPC280473
0.8155 Intermediate Similarity NPC180668
0.8155 Intermediate Similarity NPC148896
0.8155 Intermediate Similarity NPC471013
0.8128 Intermediate Similarity NPC51008
0.8128 Intermediate Similarity NPC41724
0.8093 Intermediate Similarity NPC289086
0.8093 Intermediate Similarity NPC10904
0.8063 Intermediate Similarity NPC187494
0.8054 Intermediate Similarity NPC30570
0.8037 Intermediate Similarity NPC40919
0.8037 Intermediate Similarity NPC470189
0.8018 Intermediate Similarity NPC162812
0.8 Intermediate Similarity NPC292517
0.7982 Intermediate Similarity NPC319556
0.7982 Intermediate Similarity NPC470190
0.7936 Intermediate Similarity NPC475835
0.7892 Intermediate Similarity NPC207531
0.7883 Intermediate Similarity NPC165837
0.7824 Intermediate Similarity NPC470279
0.7812 Intermediate Similarity NPC193361
0.7812 Intermediate Similarity NPC62844
0.7647 Intermediate Similarity NPC309498
0.7628 Intermediate Similarity NPC103230
0.7565 Intermediate Similarity NPC253314
0.75 Intermediate Similarity NPC471004
0.75 Intermediate Similarity NPC37473
0.7468 Intermediate Similarity NPC70155
0.7446 Intermediate Similarity NPC140311
0.7445 Intermediate Similarity NPC111732
0.7434 Intermediate Similarity NPC314834
0.7397 Intermediate Similarity NPC109922
0.7393 Intermediate Similarity NPC235885
0.7387 Intermediate Similarity NPC32451
0.7387 Intermediate Similarity NPC328559
0.7382 Intermediate Similarity NPC106593
0.735 Intermediate Similarity NPC473667
0.733 Intermediate Similarity NPC320748
0.733 Intermediate Similarity NPC324245
0.7328 Intermediate Similarity NPC183537
0.7306 Intermediate Similarity NPC107123
0.7301 Intermediate Similarity NPC314297
0.7301 Intermediate Similarity NPC315545
0.7295 Intermediate Similarity NPC15406
0.7284 Intermediate Similarity NPC210296
0.7281 Intermediate Similarity NPC327699
0.728 Intermediate Similarity NPC233334
0.7269 Intermediate Similarity NPC24019
0.7269 Intermediate Similarity NPC470280
0.7265 Intermediate Similarity NPC124313
0.7265 Intermediate Similarity NPC79223
0.7262 Intermediate Similarity NPC191489
0.7261 Intermediate Similarity NPC108342
0.7261 Intermediate Similarity NPC317752
0.7258 Intermediate Similarity NPC77878
0.7257 Intermediate Similarity NPC313345
0.7257 Intermediate Similarity NPC314855
0.7257 Intermediate Similarity NPC313796
0.7257 Intermediate Similarity NPC315638
0.7252 Intermediate Similarity NPC149708
0.7246 Intermediate Similarity NPC141428
0.724 Intermediate Similarity NPC478045
0.7238 Intermediate Similarity NPC249614
0.7231 Intermediate Similarity NPC189903
0.7231 Intermediate Similarity NPC182907
0.7229 Intermediate Similarity NPC274842
0.7225 Intermediate Similarity NPC156044
0.722 Intermediate Similarity NPC90875
0.722 Intermediate Similarity NPC123395
0.7218 Intermediate Similarity NPC476516
0.7217 Intermediate Similarity NPC318299
0.7216 Intermediate Similarity NPC100734
0.7216 Intermediate Similarity NPC315634
0.7216 Intermediate Similarity NPC88923
0.721 Intermediate Similarity NPC141385
0.7207 Intermediate Similarity NPC329024
0.7204 Intermediate Similarity NPC191310
0.72 Intermediate Similarity NPC473441
0.72 Intermediate Similarity NPC131273
0.7196 Intermediate Similarity NPC471997
0.7191 Intermediate Similarity NPC2395

  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 NPC38959 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
0.8355 Intermediate Similarity NPD8468 Phase 2
0.7757 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7713 Intermediate Similarity NPD7927 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7523 Intermediate Similarity NPD7396 Approved
0.7489 Intermediate Similarity NPD3794 Approved
0.7489 Intermediate Similarity NPD3795 Approved
0.7479 Intermediate Similarity NPD5891 Approved
0.7444 Intermediate Similarity NPD6987 Phase 1
0.7354 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7269 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD7708 Approved
0.7254 Intermediate Similarity NPD1483 Discontinued
0.7217 Intermediate Similarity NPD7069 Discontinued
0.7216 Intermediate Similarity NPD7803 Approved
0.7212 Intermediate Similarity NPD3947 Discontinued
0.7174 Intermediate Similarity NPD4417 Approved
0.7154 Intermediate Similarity NPD7956 Approved
0.7154 Intermediate Similarity NPD7955 Approved
0.7149 Intermediate Similarity NPD3280 Approved
0.713 Intermediate Similarity NPD8485 Approved
0.7124 Intermediate Similarity NPD3393 Approved
0.7124 Intermediate Similarity NPD3394 Approved
0.7124 Intermediate Similarity NPD3389 Approved
0.7123 Intermediate Similarity NPD7234 Approved
0.7123 Intermediate Similarity NPD7233 Approved
0.7118 Intermediate Similarity NPD2509 Approved
0.7118 Intermediate Similarity NPD2510 Approved
0.7106 Intermediate Similarity NPD6770 Approved
0.7105 Intermediate Similarity NPD7010 Phase 3
0.7087 Intermediate Similarity NPD4506 Discontinued
0.7061 Intermediate Similarity NPD6323 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD7777 Approved
0.7022 Intermediate Similarity NPD53 Approved
0.7022 Intermediate Similarity NPD7778 Approved
0.7021 Intermediate Similarity NPD8326 Phase 3
0.7021 Intermediate Similarity NPD8325 Phase 3
0.7021 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7004 Intermediate Similarity NPD7417 Discontinued
0.6996 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6992 Remote Similarity NPD7878 Phase 2
0.698 Remote Similarity NPD8091 Phase 3
0.6974 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6974 Remote Similarity NPD7187 Phase 2
0.6971 Remote Similarity NPD820 Phase 3
0.697 Remote Similarity NPD8466 Approved
0.697 Remote Similarity NPD8465 Approved
0.697 Remote Similarity NPD8467 Approved
0.6967 Remote Similarity NPD4373 Phase 2
0.6957 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6955 Remote Similarity NPD6962 Phase 2
0.6953 Remote Similarity NPD5475 Discontinued
0.6944 Remote Similarity NPD6525 Clinical (unspecified phase)
0.694 Remote Similarity NPD6529 Discontinued
0.6937 Remote Similarity NPD8063 Discontinued
0.6936 Remote Similarity NPD7707 Approved
0.6916 Remote Similarity NPD485 Clinical (unspecified phase)
0.6913 Remote Similarity NPD5901 Discontinued
0.691 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6897 Remote Similarity NPD7947 Clinical (unspecified phase)
0.6895 Remote Similarity NPD7886 Phase 2
0.6895 Remote Similarity NPD7885 Phase 2
0.6889 Remote Similarity NPD4427 Phase 2
0.6888 Remote Similarity NPD3925 Approved
0.6883 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6866 Remote Similarity NPD8460 Approved
0.6866 Remote Similarity NPD8425 Approved
0.6866 Remote Similarity NPD8459 Approved
0.6866 Remote Similarity NPD8426 Approved
0.6864 Remote Similarity NPD8112 Clinical (unspecified phase)
0.6862 Remote Similarity NPD8479 Phase 2
0.686 Remote Similarity NPD8289 Discontinued
0.6849 Remote Similarity NPD7395 Discontinued
0.6844 Remote Similarity NPD4952 Phase 3
0.6842 Remote Similarity NPD8429 Approved
0.6842 Remote Similarity NPD8427 Approved
0.6842 Remote Similarity NPD8428 Approved
0.684 Remote Similarity NPD6635 Approved
0.6833 Remote Similarity NPD4301 Approved
0.683 Remote Similarity NPD2336 Approved
0.6822 Remote Similarity NPD7571 Clinical (unspecified phase)
0.682 Remote Similarity NPD7404 Approved
0.6812 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6811 Remote Similarity NPD5482 Discontinued
0.681 Remote Similarity NPD7958 Clinical (unspecified phase)
0.681 Remote Similarity NPD7957 Phase 1
0.6807 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6807 Remote Similarity NPD4989 Phase 2
0.68 Remote Similarity NPD6790 Phase 1
0.679 Remote Similarity NPD5640 Discontinued
0.6789 Remote Similarity NPD6641 Approved
0.6789 Remote Similarity NPD6642 Approved
0.6786 Remote Similarity NPD8435 Approved
0.678 Remote Similarity NPD5866 Approved
0.6776 Remote Similarity NPD5022 Discontinued
0.6776 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6773 Remote Similarity NPD6716 Phase 1
0.6771 Remote Similarity NPD4948 Discontinued
0.6769 Remote Similarity NPD7862 Clinical (unspecified phase)
0.6767 Remote Similarity NPD2831 Approved
0.6766 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6761 Remote Similarity NPD5088 Discontinued
0.6754 Remote Similarity NPD5003 Discontinued
0.6752 Remote Similarity NPD7191 Phase 2
0.6748 Remote Similarity NPD7688 Phase 1
0.6747 Remote Similarity NPD5805 Approved
0.6742 Remote Similarity NPD8364 Approved
0.6742 Remote Similarity NPD8363 Approved
0.6738 Remote Similarity NPD7001 Phase 3
0.6738 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6737 Remote Similarity NPD7470 Discontinued
0.6736 Remote Similarity NPD8356 Approved
0.6736 Remote Similarity NPD6995 Phase 1
0.6736 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6726 Remote Similarity NPD3922 Approved
0.6726 Remote Similarity NPD3924 Approved
0.6726 Remote Similarity NPD4376 Phase 3
0.6726 Remote Similarity NPD3923 Approved
0.6726 Remote Similarity NPD3921 Approved
0.6721 Remote Similarity NPD7426 Phase 1
0.6719 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6718 Remote Similarity NPD7169 Suspended
0.6712 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6711 Remote Similarity NPD8360 Approved
0.6711 Remote Similarity NPD2307 Discontinued
0.6711 Remote Similarity NPD6281 Approved
0.6711 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6711 Remote Similarity NPD8361 Approved
0.6696 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6696 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6696 Remote Similarity NPD6999 Discontinued
0.6694 Remote Similarity NPD4328 Approved
0.6692 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6682 Remote Similarity NPD4889 Approved
0.6667 Remote Similarity NPD7673 Phase 3
0.6667 Remote Similarity NPD4601 Approved
0.6667 Remote Similarity NPD4600 Approved
0.6667 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6654 Remote Similarity NPD7921 Approved
0.664 Remote Similarity NPD3006 Discontinued
0.6639 Remote Similarity NPD3816 Phase 1
0.6639 Remote Similarity NPD3815 Phase 1
0.6635 Remote Similarity NPD9271 Approved
0.6627 Remote Similarity NPD6494 Phase 2
0.6627 Remote Similarity NPD5488 Discontinued
0.6627 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6626 Remote Similarity NPD8430 Approved
0.6626 Remote Similarity NPD6553 Clinical (unspecified phase)
0.6626 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6626 Remote Similarity NPD6292 Clinical (unspecified phase)
0.6625 Remote Similarity NPD8160 Phase 2
0.6624 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6624 Remote Similarity NPD6262 Clinical (unspecified phase)
0.6623 Remote Similarity NPD4528 Approved
0.6623 Remote Similarity NPD4529 Approved
0.6623 Remote Similarity NPD4526 Approved
0.6622 Remote Similarity NPD6791 Phase 2
0.6615 Remote Similarity NPD8101 Phase 3
0.6606 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6603 Remote Similarity NPD6228 Discontinued
0.6602 Remote Similarity NPD8463 Approved
0.6602 Remote Similarity NPD6276 Discontinued
0.6601 Remote Similarity NPD7576 Discontinued
0.66 Remote Similarity NPD7807 Clinical (unspecified phase)
0.6595 Remote Similarity NPD8489 Phase 1
0.6595 Remote Similarity NPD6479 Discontinued
0.6594 Remote Similarity NPD4602 Approved
0.6583 Remote Similarity NPD7538 Clinical (unspecified phase)
0.6583 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6583 Remote Similarity NPD4897 Phase 2
0.6581 Remote Similarity NPD6176 Phase 1
0.6576 Remote Similarity NPD8102 Discontinued
0.6575 Remote Similarity NPD8412 Phase 1
0.657 Remote Similarity NPD3354 Phase 2
0.657 Remote Similarity NPD4429 Discontinued
0.6568 Remote Similarity NPD7562 Approved
0.6568 Remote Similarity NPD5429 Discontinued
0.6566 Remote Similarity NPD5450 Discontinued
0.6561 Remote Similarity NPD8470 Clinical (unspecified phase)
0.656 Remote Similarity NPD7558 Phase 2
0.6557 Remote Similarity NPD5507 Approved
0.6557 Remote Similarity NPD5506 Approved
0.6555 Remote Similarity NPD6204 Clinical (unspecified phase)
0.6553 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6546 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6542 Remote Similarity NPD8094 Discontinued
0.654 Remote Similarity NPD7665 Phase 2
0.654 Remote Similarity NPD6530 Approved
0.654 Remote Similarity NPD7666 Phase 3
0.654 Remote Similarity NPD6531 Approved
0.6538 Remote Similarity NPD4926 Clinical (unspecified phase)
0.6537 Remote Similarity NPD6206 Phase 1
0.6533 Remote Similarity NPD8407 Phase 2
0.6533 Remote Similarity NPD7424 Clinical (unspecified phase)
0.6528 Remote Similarity NPD1631 Approved
0.6527 Remote Similarity NPD5416 Discontinued

  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