Structure

Physi-Chem Properties

Molecular Weight:  763.27
Volume:  722.496
LogP:  1.093
LogD:  0.592
LogS:  -4.105
# Rotatable Bonds:  11
TPSA:  246.68
# H-Bond Aceptor:  18
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.292
Synthetic Accessibility Score:  7.469
Fsp3:  0.667
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:  -5.324
MDCK Permeability:  0.00016074665472842753
Pgp-inhibitor:  0.997
Pgp-substrate:  0.261
Human Intestinal Absorption (HIA):  0.954
20% Bioavailability (F20%):  0.977
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.055
Plasma Protein Binding (PPB):  33.303138732910156%
Volume Distribution (VD):  1.171
Pgp-substrate:  40.429019927978516%

ADMET: Metabolism

CYP1A2-inhibitor:  0.034
CYP1A2-substrate:  0.015
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.058
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.009
CYP2D6-inhibitor:  0.824
CYP2D6-substrate:  0.034
CYP3A4-inhibitor:  0.659
CYP3A4-substrate:  0.249

ADMET: Excretion

Clearance (CL):  2.446
Half-life (T1/2):  0.725

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.967
Drug-inuced Liver Injury (DILI):  0.971
AMES Toxicity:  0.047
Rat Oral Acute Toxicity:  0.027
Maximum Recommended Daily Dose:  0.017
Skin Sensitization:  0.172
Carcinogencity:  0.097
Eye Corrosion:  0.003
Eye Irritation:  0.044
Respiratory Toxicity:  0.029

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

  Natural Product: NPC473850

Natural Product ID:  NPC473850
Common Name*:   Tripfordine B
IUPAC Name:   n.a.
Synonyms:   tripfordine B
Standard InCHIKey:  VCRRHFSJEWAFJW-LRACBKHPSA-N
Standard InCHI:  InChI=1S/C36H45NO17/c1-16-11-12-23-22(10-9-13-37-23)32(45)48-14-33(7)24-25(49-18(3)39)29(51-20(5)41)35(15-47-17(2)38)30(52-21(6)42)26(50-19(4)40)28(53-31(16)44)34(8,46)36(35,54-33)27(24)43/h9-10,13,16,24-30,43,46H,11-12,14-15H2,1-8H3/t16?,24-,25-,26+,27-,28+,29-,30+,33+,34-,35-,36+/m1/s1
SMILES:  CC1CCC2=C(C=CC=N2)C(=O)OCC3(C4C(C(C5(C(C(C(C(C5(C4O)O3)(C)O)OC1=O)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL453463
PubChem CID:   44583868
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. 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
NPT759 Cell Line H9 Homo sapiens IC50 > 25.0 ug.mL-1 PMID[465265]
NPT81 Cell Line A549 Homo sapiens IC50 > 4.0 ug.mL-1 PMID[465265]
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 4.0 ug.mL-1 PMID[465265]
NPT762 Cell Line A-431 Homo sapiens IC50 > 4.0 ug.mL-1 PMID[465265]
NPT858 Cell Line LNCaP Homo sapiens IC50 > 4.0 ug.mL-1 PMID[465265]
NPT306 Cell Line PC-3 Homo sapiens IC50 > 4.0 ug.mL-1 PMID[465265]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 4.0 ug.mL-1 PMID[465265]

☑ 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 NPC473850 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
0.995 High Similarity NPC250807
0.995 High Similarity NPC57797
0.9851 High Similarity NPC475362
0.9802 High Similarity NPC328186
0.9802 High Similarity NPC146824
0.9802 High Similarity NPC477787
0.9802 High Similarity NPC228377
0.9802 High Similarity NPC122968
0.9801 High Similarity NPC475137
0.9801 High Similarity NPC475498
0.9751 High Similarity NPC76565
0.966 High Similarity NPC237702
0.9659 High Similarity NPC292416
0.9659 High Similarity NPC473689
0.9659 High Similarity NPC316841
0.9657 High Similarity NPC475644
0.9657 High Similarity NPC471190
0.9657 High Similarity NPC471977
0.9657 High Similarity NPC470486
0.9648 High Similarity NPC471014
0.9648 High Similarity NPC475408
0.9648 High Similarity NPC471016
0.9612 High Similarity NPC319880
0.9612 High Similarity NPC244839
0.9612 High Similarity NPC320324
0.9608 High Similarity NPC476110
0.9608 High Similarity NPC475631
0.9608 High Similarity NPC475600
0.9608 High Similarity NPC87152
0.9604 High Similarity NPC477788
0.9598 High Similarity NPC470306
0.9559 High Similarity NPC473506
0.9519 High Similarity NPC475406
0.9517 High Similarity NPC30456
0.9474 High Similarity NPC327904
0.9474 High Similarity NPC38959
0.9469 High Similarity NPC475596
0.9469 High Similarity NPC475303
0.9455 High Similarity NPC301368
0.9455 High Similarity NPC84815
0.9426 High Similarity NPC170751
0.9406 High Similarity NPC144779
0.9406 High Similarity NPC294579
0.9366 High Similarity NPC471980
0.9356 High Similarity NPC6981
0.934 High Similarity NPC253482
0.9333 High Similarity NPC327769
0.9333 High Similarity NPC475426
0.9333 High Similarity NPC35208
0.932 High Similarity NPC328154
0.9317 High Similarity NPC127026
0.9317 High Similarity NPC127720
0.931 High Similarity NPC62367
0.9265 High Similarity NPC216428
0.9257 High Similarity NPC4421
0.9254 High Similarity NPC472553
0.9231 High Similarity NPC475601
0.9227 High Similarity NPC477902
0.9212 High Similarity NPC477909
0.9212 High Similarity NPC42678
0.9212 High Similarity NPC477907
0.9209 High Similarity NPC475648
0.9175 High Similarity NPC477912
0.9147 High Similarity NPC469748
0.9139 High Similarity NPC124029
0.9139 High Similarity NPC211920
0.9122 High Similarity NPC212768
0.9122 High Similarity NPC473115
0.9122 High Similarity NPC75600
0.9122 High Similarity NPC158020
0.9122 High Similarity NPC473089
0.9122 High Similarity NPC6576
0.9118 High Similarity NPC477910
0.9104 High Similarity NPC48042
0.9104 High Similarity NPC472550
0.9104 High Similarity NPC304179
0.91 High Similarity NPC150698
0.91 High Similarity NPC96801
0.9069 High Similarity NPC319128
0.9055 High Similarity NPC63041
0.9 High Similarity NPC148860
0.8986 High Similarity NPC472555
0.8976 High Similarity NPC228331
0.8976 High Similarity NPC264674
0.892 High Similarity NPC477906
0.89 High Similarity NPC477903
0.8889 High Similarity NPC477908
0.8889 High Similarity NPC206343
0.8857 High Similarity NPC477911
0.8839 High Similarity NPC53255
0.8839 High Similarity NPC85879
0.88 High Similarity NPC13603
0.8774 High Similarity NPC477900
0.8774 High Similarity NPC477899
0.8768 High Similarity NPC235364
0.8696 High Similarity NPC476467
0.869 High Similarity NPC471978
0.8685 High Similarity NPC26881
0.8673 High Similarity NPC326930
0.8673 High Similarity NPC477901
0.8673 High Similarity NPC475301
0.8527 High Similarity NPC475533
0.8525 High Similarity NPC91125
0.8522 High Similarity NPC473833
0.8519 High Similarity NPC14116
0.8519 High Similarity NPC285411
0.8498 Intermediate Similarity NPC471979
0.8493 Intermediate Similarity NPC238278
0.8489 Intermediate Similarity NPC324619
0.8489 Intermediate Similarity NPC475315
0.8479 Intermediate Similarity NPC134384
0.8479 Intermediate Similarity NPC311196
0.8462 Intermediate Similarity NPC472752
0.8448 Intermediate Similarity NPC328928
0.8429 Intermediate Similarity NPC280473
0.8429 Intermediate Similarity NPC323551
0.84 Intermediate Similarity NPC180668
0.84 Intermediate Similarity NPC471013
0.84 Intermediate Similarity NPC148896
0.8389 Intermediate Similarity NPC51008
0.8389 Intermediate Similarity NPC41724
0.8384 Intermediate Similarity NPC471015
0.8364 Intermediate Similarity NPC213143
0.8319 Intermediate Similarity NPC476090
0.831 Intermediate Similarity NPC30570
0.8271 Intermediate Similarity NPC162812
0.8269 Intermediate Similarity NPC289086
0.8257 Intermediate Similarity NPC233727
0.8255 Intermediate Similarity NPC292517
0.8253 Intermediate Similarity NPC10904
0.814 Intermediate Similarity NPC62844
0.814 Intermediate Similarity NPC193361
0.8131 Intermediate Similarity NPC165837
0.8122 Intermediate Similarity NPC470189
0.8122 Intermediate Similarity NPC40919
0.8104 Intermediate Similarity NPC475835
0.8077 Intermediate Similarity NPC470279
0.8066 Intermediate Similarity NPC470190
0.8065 Intermediate Similarity NPC187494
0.7982 Intermediate Similarity NPC319556
0.789 Intermediate Similarity NPC207531
0.7887 Intermediate Similarity NPC309498
0.787 Intermediate Similarity NPC37473
0.7793 Intermediate Similarity NPC253314
0.7788 Intermediate Similarity NPC103230
0.7725 Intermediate Similarity NPC320748
0.7725 Intermediate Similarity NPC324245
0.77 Intermediate Similarity NPC328559
0.77 Intermediate Similarity NPC32451
0.7671 Intermediate Similarity NPC111732
0.7653 Intermediate Similarity NPC79223
0.7604 Intermediate Similarity NPC156044
0.7594 Intermediate Similarity NPC329024
0.758 Intermediate Similarity NPC314834
0.7565 Intermediate Similarity NPC471004
0.7562 Intermediate Similarity NPC249614
0.7532 Intermediate Similarity NPC70155
0.7523 Intermediate Similarity NPC123395
0.7512 Intermediate Similarity NPC25442
0.7512 Intermediate Similarity NPC12944
0.7511 Intermediate Similarity NPC107123
0.75 Intermediate Similarity NPC141385
0.7488 Intermediate Similarity NPC207851
0.7477 Intermediate Similarity NPC59033
0.7477 Intermediate Similarity NPC317672
0.7465 Intermediate Similarity NPC109922
0.7443 Intermediate Similarity NPC315545
0.7443 Intermediate Similarity NPC314297
0.7438 Intermediate Similarity NPC191310
0.7427 Intermediate Similarity NPC317010
0.7418 Intermediate Similarity NPC135950
0.7417 Intermediate Similarity NPC476516
0.7397 Intermediate Similarity NPC313345
0.7397 Intermediate Similarity NPC314855
0.7397 Intermediate Similarity NPC315638
0.7397 Intermediate Similarity NPC313796
0.738 Intermediate Similarity NPC235885
0.7373 Intermediate Similarity NPC155792
0.7361 Intermediate Similarity NPC103361
0.7357 Intermediate Similarity NPC140311
0.7352 Intermediate Similarity NPC477043
0.7346 Intermediate Similarity NPC44354
0.733 Intermediate Similarity NPC470280
0.7321 Intermediate Similarity NPC317752
0.7315 Intermediate Similarity NPC149708
0.7304 Intermediate Similarity NPC141428
0.7293 Intermediate Similarity NPC106593
0.7277 Intermediate Similarity NPC318299
0.7273 Intermediate Similarity NPC314648
0.7261 Intermediate Similarity NPC473667
0.726 Intermediate Similarity NPC471997
0.7257 Intermediate Similarity NPC204491
0.7256 Intermediate Similarity NPC198205
0.7256 Intermediate Similarity NPC21483
0.7254 Intermediate Similarity NPC473441
0.7254 Intermediate Similarity NPC131273
0.7243 Intermediate Similarity NPC183537
0.7241 Intermediate Similarity NPC57690
0.7235 Intermediate Similarity NPC311054
0.7235 Intermediate Similarity NPC112752

  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 NPC473850 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
0.8363 Intermediate Similarity NPD8468 Phase 2
0.801 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.799 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD3794 Approved
0.7717 Intermediate Similarity NPD3795 Approved
0.7664 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD7396 Approved
0.7545 Intermediate Similarity NPD7927 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD5891 Approved
0.7458 Intermediate Similarity NPD1483 Discontinued
0.7431 Intermediate Similarity NPD3947 Discontinued
0.7387 Intermediate Similarity NPD4417 Approved
0.7361 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD3280 Approved
0.7354 Intermediate Similarity NPD7069 Discontinued
0.7301 Intermediate Similarity NPD8325 Phase 3
0.7301 Intermediate Similarity NPD8326 Phase 3
0.7301 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD4506 Discontinued
0.7286 Intermediate Similarity NPD820 Phase 3
0.7273 Intermediate Similarity NPD6987 Phase 1
0.7252 Intermediate Similarity NPD2509 Approved
0.7252 Intermediate Similarity NPD2510 Approved
0.7237 Intermediate Similarity NPD6770 Approved
0.722 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD7233 Approved
0.7183 Intermediate Similarity NPD7234 Approved
0.7181 Intermediate Similarity NPD3389 Approved
0.7181 Intermediate Similarity NPD3393 Approved
0.7181 Intermediate Similarity NPD3394 Approved
0.7162 Intermediate Similarity NPD7010 Phase 3
0.7149 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6529 Discontinued
0.7118 Intermediate Similarity NPD7878 Phase 2
0.7108 Intermediate Similarity NPD7708 Approved
0.7106 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7085 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD6641 Approved
0.7081 Intermediate Similarity NPD6642 Approved
0.708 Intermediate Similarity NPD5475 Discontinued
0.7078 Intermediate Similarity NPD7778 Approved
0.7078 Intermediate Similarity NPD7777 Approved
0.7078 Intermediate Similarity NPD53 Approved
0.7078 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD8063 Discontinued
0.7063 Intermediate Similarity NPD7803 Approved
0.7059 Intermediate Similarity NPD6635 Approved
0.7056 Intermediate Similarity NPD8479 Phase 2
0.704 Intermediate Similarity NPD6323 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD5901 Discontinued
0.7037 Intermediate Similarity NPD2336 Approved
0.7018 Intermediate Similarity NPD4427 Phase 2
0.7 Intermediate Similarity NPD7955 Approved
0.7 Intermediate Similarity NPD7956 Approved
0.6992 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6953 Remote Similarity NPD4301 Approved
0.6942 Remote Similarity NPD7886 Phase 2
0.6942 Remote Similarity NPD7885 Phase 2
0.6935 Remote Similarity NPD9271 Approved
0.6919 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6914 Remote Similarity NPD6790 Phase 1
0.6913 Remote Similarity NPD7707 Approved
0.6909 Remote Similarity NPD2307 Discontinued
0.69 Remote Similarity NPD5866 Approved
0.6898 Remote Similarity NPD4948 Discontinued
0.6891 Remote Similarity NPD5022 Discontinued
0.687 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6864 Remote Similarity NPD3925 Approved
0.6861 Remote Similarity NPD4601 Approved
0.6861 Remote Similarity NPD4600 Approved
0.686 Remote Similarity NPD5805 Approved
0.6858 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6858 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6856 Remote Similarity NPD7470 Discontinued
0.6855 Remote Similarity NPD5482 Discontinued
0.6851 Remote Similarity NPD6995 Phase 1
0.6849 Remote Similarity NPD4376 Phase 3
0.6844 Remote Similarity NPD7417 Discontinued
0.6835 Remote Similarity NPD8289 Discontinued
0.6833 Remote Similarity NPD7061 Clinical (unspecified phase)
0.682 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6814 Remote Similarity NPD6026 Approved
0.6812 Remote Similarity NPD5088 Discontinued
0.6812 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6811 Remote Similarity NPD7862 Clinical (unspecified phase)
0.6806 Remote Similarity NPD4889 Approved
0.6805 Remote Similarity NPD4373 Phase 2
0.6802 Remote Similarity NPD5003 Discontinued
0.6802 Remote Similarity NPD8485 Approved
0.68 Remote Similarity NPD7187 Phase 2
0.68 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6792 Remote Similarity NPD6962 Phase 2
0.6792 Remote Similarity NPD7688 Phase 1
0.6792 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6786 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6784 Remote Similarity NPD7001 Phase 3
0.6781 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6773 Remote Similarity NPD3922 Approved
0.6773 Remote Similarity NPD3924 Approved
0.6773 Remote Similarity NPD3923 Approved
0.6773 Remote Similarity NPD3921 Approved
0.6761 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6759 Remote Similarity NPD8091 Phase 3
0.675 Remote Similarity NPD9075 Approved
0.675 Remote Similarity NPD9074 Approved
0.6749 Remote Similarity NPD3006 Discontinued
0.6744 Remote Similarity NPD3178 Discontinued
0.6742 Remote Similarity NPD4528 Approved
0.6742 Remote Similarity NPD4526 Approved
0.6742 Remote Similarity NPD4529 Approved
0.6741 Remote Similarity NPD6999 Discontinued
0.6741 Remote Similarity NPD7000 Clinical (unspecified phase)
0.674 Remote Similarity NPD2831 Approved
0.6736 Remote Similarity NPD4086 Phase 1
0.6731 Remote Similarity NPD1631 Approved
0.6725 Remote Similarity NPD7947 Clinical (unspecified phase)
0.6723 Remote Similarity NPD7404 Approved
0.6711 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6709 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6709 Remote Similarity NPD8356 Approved
0.6709 Remote Similarity NPD4989 Phase 2
0.6707 Remote Similarity NPD6276 Discontinued
0.6699 Remote Similarity NPD2581 Approved
0.6699 Remote Similarity NPD2582 Approved
0.6697 Remote Similarity NPD6665 Discontinued
0.6696 Remote Similarity NPD6176 Phase 1
0.6695 Remote Similarity NPD7426 Phase 1
0.6695 Remote Similarity NPD8112 Clinical (unspecified phase)
0.6695 Remote Similarity NPD5640 Discontinued
0.6692 Remote Similarity NPD8466 Approved
0.6692 Remote Similarity NPD8465 Approved
0.6692 Remote Similarity NPD8467 Approved
0.6682 Remote Similarity NPD8435 Approved
0.6682 Remote Similarity NPD6281 Approved
0.6682 Remote Similarity NPD8361 Approved
0.6682 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6682 Remote Similarity NPD8360 Approved
0.6681 Remote Similarity NPD7395 Discontinued
0.668 Remote Similarity NPD6716 Phase 1
0.668 Remote Similarity NPD4952 Phase 3
0.6667 Remote Similarity NPD6791 Phase 2
0.6667 Remote Similarity NPD6361 Phase 2
0.6667 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8160 Phase 2
0.6667 Remote Similarity NPD6292 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6553 Clinical (unspecified phase)
0.6654 Remote Similarity NPD8363 Approved
0.6654 Remote Similarity NPD8364 Approved
0.6653 Remote Similarity NPD8409 Suspended
0.6652 Remote Similarity NPD8399 Phase 1
0.6652 Remote Similarity NPD8423 Phase 2
0.6651 Remote Similarity NPD8407 Phase 2
0.6641 Remote Similarity NPD6228 Discontinued
0.6638 Remote Similarity NPD7957 Phase 1
0.6638 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6637 Remote Similarity NPD4500 Approved
0.6637 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6637 Remote Similarity NPD7944 Discontinued
0.6637 Remote Similarity NPD4501 Approved
0.6637 Remote Similarity NPD6479 Discontinued
0.6636 Remote Similarity NPD5100 Phase 3
0.6635 Remote Similarity NPD2511 Approved
0.6633 Remote Similarity NPD107 Approved
0.6624 Remote Similarity NPD1996 Discontinued
0.661 Remote Similarity NPD3354 Phase 2
0.661 Remote Similarity NPD4429 Discontinued
0.6609 Remote Similarity NPD3815 Phase 1
0.6609 Remote Similarity NPD3816 Phase 1
0.6609 Remote Similarity NPD7562 Approved
0.6606 Remote Similarity NPD2564 Approved
0.6606 Remote Similarity NPD2565 Phase 2
0.6604 Remote Similarity NPD1573 Approved
0.6604 Remote Similarity NPD1575 Approved
0.6603 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6602 Remote Similarity NPD5450 Discontinued
0.6598 Remote Similarity NPD8430 Approved
0.6598 Remote Similarity NPD3259 Approved
0.6598 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6597 Remote Similarity NPD6298 Discontinued
0.6594 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6594 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6592 Remote Similarity NPD8426 Approved
0.6592 Remote Similarity NPD8460 Approved
0.6592 Remote Similarity NPD8425 Approved
0.6592 Remote Similarity NPD8459 Approved
0.6591 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6591 Remote Similarity NPD6257 Clinical (unspecified phase)
0.659 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6589 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6587 Remote Similarity NPD8101 Phase 3
0.6587 Remote Similarity NPD1630 Approved
0.658 Remote Similarity NPD7191 Phase 2
0.6575 Remote Similarity NPD8370 Discontinued
0.6573 Remote Similarity NPD7576 Discontinued
0.6573 Remote Similarity NPD6739 Clinical (unspecified phase)
0.6571 Remote Similarity NPD7807 Clinical (unspecified phase)
0.6568 Remote Similarity NPD8404 Phase 2
0.6567 Remote Similarity NPD7703 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