Structure

Physi-Chem Properties

Molecular Weight:  779.26
Volume:  731.286
LogP:  0.897
LogD:  0.445
LogS:  -3.688
# Rotatable Bonds:  11
TPSA:  266.91
# H-Bond Aceptor:  19
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.24
Synthetic Accessibility Score:  7.591
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:  -5.442
MDCK Permeability:  0.00015449461352545768
Pgp-inhibitor:  0.982
Pgp-substrate:  0.881
Human Intestinal Absorption (HIA):  0.979
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.077
Plasma Protein Binding (PPB):  25.828306198120117%
Volume Distribution (VD):  0.932
Pgp-substrate:  41.69932556152344%

ADMET: Metabolism

CYP1A2-inhibitor:  0.01
CYP1A2-substrate:  0.02
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.009
CYP2D6-inhibitor:  0.247
CYP2D6-substrate:  0.022
CYP3A4-inhibitor:  0.506
CYP3A4-substrate:  0.214

ADMET: Excretion

Clearance (CL):  1.962
Half-life (T1/2):  0.717

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.881
Drug-inuced Liver Injury (DILI):  0.945
AMES Toxicity:  0.063
Rat Oral Acute Toxicity:  0.038
Maximum Recommended Daily Dose:  0.012
Skin Sensitization:  0.051
Carcinogencity:  0.082
Eye Corrosion:  0.003
Eye Irritation:  0.02
Respiratory Toxicity:  0.017

Download Data

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

  Natural Product: NPC475362

Natural Product ID:  NPC475362
Common Name*:   Tripfordine A
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  YISOUQSWAUFAAP-KYCLAKFMSA-N
Standard InCHI:  InChI=1S/C36H45NO18/c1-16(38)48-15-35-28(52-19(4)41)24(43)27-34(8,47)36(35)26(51-18(3)40)23(25(50-17(2)39)29(35)53-20(5)42)33(7,55-36)14-49-30(44)21-10-9-13-37-22(21)11-12-32(6,46)31(45)54-27/h9-10,13,23-29,43,46-47H,11-12,14-15H2,1-8H3/t23-,24+,25-,26-,27+,28+,29-,32?,33+,34-,35+,36+/m1/s1
SMILES:  CC(=O)OC[C@]12[C@@H](OC(=O)C)[C@@H](O)[C@H]3[C@@]([C@@]42O[C@@]([C@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)[C@H]4OC(=O)C)(C)COC(=O)c1cccnc1CCC(C(=O)O3)(C)O)(C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL504312
PubChem CID:   44583867
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
NPT759 Cell Line H9 Homo sapiens IC50 > 25.0 ug.mL-1 PMID[505495]
NPT81 Cell Line A549 Homo sapiens IC50 > 4.0 ug.mL-1 PMID[505495]
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 4.0 ug.mL-1 PMID[505495]
NPT762 Cell Line A-431 Homo sapiens IC50 > 4.0 ug.mL-1 PMID[505495]
NPT858 Cell Line LNCaP Homo sapiens IC50 > 4.0 ug.mL-1 PMID[505495]
NPT306 Cell Line PC-3 Homo sapiens IC50 > 4.0 ug.mL-1 PMID[505495]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 13.4 ug.mL-1 PMID[505495]
NPT27 Others Unspecified Ratio IC50/EC50 = 1.9 n.a. PMID[505495]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 4.0 ug.mL-1 PMID[505495]

☑ 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 NPC475362 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 NPC146824
0.9851 High Similarity NPC473850
0.9806 High Similarity NPC237702
0.9805 High Similarity NPC292416
0.9805 High Similarity NPC473689
0.9802 High Similarity NPC250807
0.9802 High Similarity NPC57797
0.9757 High Similarity NPC244839
0.9757 High Similarity NPC319880
0.9757 High Similarity NPC320324
0.9754 High Similarity NPC475498
0.9754 High Similarity NPC475137
0.9704 High Similarity NPC76565
0.9663 High Similarity NPC475406
0.9659 High Similarity NPC228377
0.9659 High Similarity NPC122968
0.9659 High Similarity NPC328186
0.9659 High Similarity NPC477787
0.9617 High Similarity NPC327904
0.9617 High Similarity NPC38959
0.9612 High Similarity NPC471190
0.9612 High Similarity NPC470486
0.9612 High Similarity NPC475644
0.9612 High Similarity NPC471977
0.9563 High Similarity NPC476110
0.9563 High Similarity NPC475600
0.9563 High Similarity NPC87152
0.9563 High Similarity NPC475631
0.9519 High Similarity NPC316841
0.9515 High Similarity NPC473506
0.9505 High Similarity NPC471016
0.9505 High Similarity NPC475408
0.9505 High Similarity NPC471014
0.9481 High Similarity NPC253482
0.9476 High Similarity NPC35208
0.9474 High Similarity NPC30456
0.9463 High Similarity NPC477788
0.9455 High Similarity NPC470306
0.9426 High Similarity NPC475303
0.9426 High Similarity NPC475596
0.9384 High Similarity NPC170751
0.9372 High Similarity NPC328154
0.9349 High Similarity NPC475648
0.9317 High Similarity NPC84815
0.9317 High Similarity NPC301368
0.9292 High Similarity NPC475426
0.9292 High Similarity NPC327769
0.9282 High Similarity NPC475601
0.9268 High Similarity NPC294579
0.9268 High Similarity NPC144779
0.9231 High Similarity NPC471980
0.9227 High Similarity NPC477912
0.922 High Similarity NPC6981
0.9198 High Similarity NPC469748
0.9183 High Similarity NPC127026
0.9183 High Similarity NPC127720
0.9175 High Similarity NPC62367
0.9171 High Similarity NPC477910
0.9151 High Similarity NPC96801
0.9151 High Similarity NPC150698
0.913 High Similarity NPC216428
0.9122 High Similarity NPC319128
0.9122 High Similarity NPC4421
0.9118 High Similarity NPC472553
0.9095 High Similarity NPC477902
0.9078 High Similarity NPC42678
0.9078 High Similarity NPC477907
0.9078 High Similarity NPC477909
0.9052 High Similarity NPC148860
0.9029 High Similarity NPC228331
0.9009 High Similarity NPC124029
0.9009 High Similarity NPC211920
0.899 High Similarity NPC473089
0.899 High Similarity NPC212768
0.899 High Similarity NPC75600
0.899 High Similarity NPC473115
0.899 High Similarity NPC6576
0.899 High Similarity NPC158020
0.8971 High Similarity NPC472550
0.8971 High Similarity NPC304179
0.8971 High Similarity NPC48042
0.8933 High Similarity NPC13603
0.8922 High Similarity NPC63041
0.891 High Similarity NPC477911
0.8889 High Similarity NPC85879
0.8889 High Similarity NPC53255
0.8857 High Similarity NPC472555
0.8846 High Similarity NPC264674
0.8821 High Similarity NPC471978
0.8805 High Similarity NPC475301
0.8805 High Similarity NPC326930
0.8796 High Similarity NPC477906
0.8774 High Similarity NPC477903
0.8762 High Similarity NPC206343
0.8762 High Similarity NPC477908
0.8652 High Similarity NPC473833
0.8651 High Similarity NPC477899
0.8651 High Similarity NPC477900
0.8645 High Similarity NPC235364
0.8627 High Similarity NPC471979
0.8578 High Similarity NPC328928
0.8578 High Similarity NPC475533
0.8571 High Similarity NPC476467
0.8571 High Similarity NPC14116
0.8571 High Similarity NPC285411
0.8565 High Similarity NPC26881
0.8551 High Similarity NPC477901
0.8545 High Similarity NPC238278
0.854 High Similarity NPC475315
0.854 High Similarity NPC324619
0.8532 High Similarity NPC311196
0.8532 High Similarity NPC134384
0.8517 High Similarity NPC472752
0.8435 Intermediate Similarity NPC471015
0.8416 Intermediate Similarity NPC213143
0.8409 Intermediate Similarity NPC91125
0.8311 Intermediate Similarity NPC233727
0.831 Intermediate Similarity NPC280473
0.831 Intermediate Similarity NPC323551
0.8289 Intermediate Similarity NPC180668
0.8289 Intermediate Similarity NPC471013
0.8289 Intermediate Similarity NPC148896
0.8271 Intermediate Similarity NPC51008
0.8271 Intermediate Similarity NPC41724
0.821 Intermediate Similarity NPC476090
0.8194 Intermediate Similarity NPC30570
0.8178 Intermediate Similarity NPC470189
0.8178 Intermediate Similarity NPC40919
0.8157 Intermediate Similarity NPC162812
0.8152 Intermediate Similarity NPC289086
0.8147 Intermediate Similarity NPC10904
0.814 Intermediate Similarity NPC292517
0.8122 Intermediate Similarity NPC470190
0.8119 Intermediate Similarity NPC187494
0.8048 Intermediate Similarity NPC470279
0.8037 Intermediate Similarity NPC319556
0.8028 Intermediate Similarity NPC62844
0.8028 Intermediate Similarity NPC193361
0.8018 Intermediate Similarity NPC165837
0.7991 Intermediate Similarity NPC475835
0.7945 Intermediate Similarity NPC207531
0.7778 Intermediate Similarity NPC309498
0.7768 Intermediate Similarity NPC37473
0.7768 Intermediate Similarity NPC253314
0.7678 Intermediate Similarity NPC103230
0.7674 Intermediate Similarity NPC328559
0.7674 Intermediate Similarity NPC32451
0.7617 Intermediate Similarity NPC320748
0.7617 Intermediate Similarity NPC324245
0.7606 Intermediate Similarity NPC109922
0.7568 Intermediate Similarity NPC111732
0.7557 Intermediate Similarity NPC314834
0.7546 Intermediate Similarity NPC79223
0.7543 Intermediate Similarity NPC471004
0.7511 Intermediate Similarity NPC70155
0.7511 Intermediate Similarity NPC235885
0.75 Intermediate Similarity NPC156044
0.7488 Intermediate Similarity NPC329024
0.7478 Intermediate Similarity NPC141385
0.7454 Intermediate Similarity NPC317672
0.7454 Intermediate Similarity NPC149708
0.7451 Intermediate Similarity NPC249614
0.7435 Intermediate Similarity NPC141428
0.7421 Intermediate Similarity NPC315545
0.7421 Intermediate Similarity NPC314297
0.7419 Intermediate Similarity NPC123395
0.7417 Intermediate Similarity NPC107123
0.7409 Intermediate Similarity NPC12944
0.7409 Intermediate Similarity NPC477043
0.7409 Intermediate Similarity NPC25442
0.7404 Intermediate Similarity NPC471997
0.7404 Intermediate Similarity NPC317010
0.7397 Intermediate Similarity NPC476516
0.7381 Intermediate Similarity NPC207851
0.7376 Intermediate Similarity NPC313796
0.7376 Intermediate Similarity NPC315638
0.7376 Intermediate Similarity NPC313345
0.7376 Intermediate Similarity NPC314855
0.7373 Intermediate Similarity NPC59033
0.7371 Intermediate Similarity NPC57690
0.7336 Intermediate Similarity NPC140311
0.733 Intermediate Similarity NPC191310
0.7315 Intermediate Similarity NPC135950
0.7304 Intermediate Similarity NPC2395
0.7273 Intermediate Similarity NPC155792
0.7273 Intermediate Similarity NPC106593
0.726 Intermediate Similarity NPC103361
0.7256 Intermediate Similarity NPC114974
0.7253 Intermediate Similarity NPC267926
0.7252 Intermediate Similarity NPC314648
0.7243 Intermediate Similarity NPC44354
0.7241 Intermediate Similarity NPC473667
0.7237 Intermediate Similarity NPC204491
0.7237 Intermediate Similarity NPC203614
0.7236 Intermediate Similarity NPC473441
0.7236 Intermediate Similarity NPC131273
0.7232 Intermediate Similarity NPC470280
0.7225 Intermediate Similarity NPC317752
0.7224 Intermediate Similarity NPC183537
0.7208 Intermediate Similarity NPC471583

  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 NPC475362 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
0.8496 Intermediate Similarity NPD8468 Phase 2
0.7895 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD3794 Approved
0.7613 Intermediate Similarity NPD3795 Approved
0.7558 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7489 Intermediate Similarity NPD7396 Approved
0.7447 Intermediate Similarity NPD5891 Approved
0.7444 Intermediate Similarity NPD7927 Clinical (unspecified phase)
0.7409 Intermediate Similarity NPD6987 Phase 1
0.7364 Intermediate Similarity NPD1483 Discontinued
0.733 Intermediate Similarity NPD3947 Discontinued
0.7289 Intermediate Similarity NPD4417 Approved
0.7261 Intermediate Similarity NPD3280 Approved
0.726 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD7069 Discontinued
0.7234 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD2510 Approved
0.7232 Intermediate Similarity NPD2509 Approved
0.7205 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD8325 Phase 3
0.7205 Intermediate Similarity NPD8326 Phase 3
0.72 Intermediate Similarity NPD4506 Discontinued
0.7178 Intermediate Similarity NPD820 Phase 3
0.7162 Intermediate Similarity NPD3389 Approved
0.7162 Intermediate Similarity NPD3393 Approved
0.7162 Intermediate Similarity NPD3394 Approved
0.7143 Intermediate Similarity NPD6770 Approved
0.713 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD7708 Approved
0.7083 Intermediate Similarity NPD7234 Approved
0.7083 Intermediate Similarity NPD7233 Approved
0.7067 Intermediate Similarity NPD7010 Phase 3
0.7067 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7778 Approved
0.7059 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD53 Approved
0.7059 Intermediate Similarity NPD7777 Approved
0.7048 Intermediate Similarity NPD6529 Discontinued
0.7047 Intermediate Similarity NPD7803 Approved
0.7026 Intermediate Similarity NPD7878 Phase 2
0.7 Intermediate Similarity NPD4427 Phase 2
0.6991 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6987 Remote Similarity NPD5475 Discontinued
0.6984 Remote Similarity NPD7956 Approved
0.6984 Remote Similarity NPD7955 Approved
0.6981 Remote Similarity NPD6641 Approved
0.6981 Remote Similarity NPD6642 Approved
0.6972 Remote Similarity NPD8063 Discontinued
0.697 Remote Similarity NPD7707 Approved
0.6966 Remote Similarity NPD8479 Phase 2
0.6957 Remote Similarity NPD6635 Approved
0.6947 Remote Similarity NPD5901 Discontinued
0.6947 Remote Similarity NPD6323 Clinical (unspecified phase)
0.6943 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6941 Remote Similarity NPD2336 Approved
0.6929 Remote Similarity NPD4373 Phase 2
0.692 Remote Similarity NPD3925 Approved
0.6908 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5022 Discontinued
0.6875 Remote Similarity NPD5088 Discontinued
0.6864 Remote Similarity NPD4301 Approved
0.6861 Remote Similarity NPD8485 Approved
0.6858 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6857 Remote Similarity NPD7885 Phase 2
0.6857 Remote Similarity NPD7886 Phase 2
0.6853 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6846 Remote Similarity NPD6962 Phase 2
0.684 Remote Similarity NPD5482 Discontinued
0.6832 Remote Similarity NPD9271 Approved
0.6829 Remote Similarity NPD7417 Discontinued
0.6829 Remote Similarity NPD6790 Phase 1
0.6822 Remote Similarity NPD5751 Clinical (unspecified phase)
0.682 Remote Similarity NPD8289 Discontinued
0.682 Remote Similarity NPD5640 Discontinued
0.6816 Remote Similarity NPD2307 Discontinued
0.681 Remote Similarity NPD5866 Approved
0.6806 Remote Similarity NPD8465 Approved
0.6806 Remote Similarity NPD8466 Approved
0.6806 Remote Similarity NPD8467 Approved
0.6805 Remote Similarity NPD4952 Phase 3
0.6804 Remote Similarity NPD4948 Discontinued
0.6798 Remote Similarity NPD2831 Approved
0.6786 Remote Similarity NPD5003 Discontinued
0.6776 Remote Similarity NPD5805 Approved
0.677 Remote Similarity NPD4601 Approved
0.677 Remote Similarity NPD8486 Clinical (unspecified phase)
0.677 Remote Similarity NPD4396 Clinical (unspecified phase)
0.677 Remote Similarity NPD4600 Approved
0.6769 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6769 Remote Similarity NPD7001 Phase 3
0.6767 Remote Similarity NPD7470 Discontinued
0.6766 Remote Similarity NPD4989 Phase 2
0.6766 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6765 Remote Similarity NPD6995 Phase 1
0.6757 Remote Similarity NPD3921 Approved
0.6757 Remote Similarity NPD3922 Approved
0.6757 Remote Similarity NPD3924 Approved
0.6757 Remote Similarity NPD4376 Phase 3
0.6757 Remote Similarity NPD3923 Approved
0.6747 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6745 Remote Similarity NPD8091 Phase 3
0.6744 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6742 Remote Similarity NPD8435 Approved
0.6742 Remote Similarity NPD8361 Approved
0.6742 Remote Similarity NPD8360 Approved
0.6741 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6736 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6735 Remote Similarity NPD3006 Discontinued
0.6732 Remote Similarity NPD7862 Clinical (unspecified phase)
0.6726 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6726 Remote Similarity NPD4526 Approved
0.6726 Remote Similarity NPD4529 Approved
0.6726 Remote Similarity NPD6999 Discontinued
0.6726 Remote Similarity NPD4528 Approved
0.6722 Remote Similarity NPD4086 Phase 1
0.6715 Remote Similarity NPD6026 Approved
0.6712 Remote Similarity NPD8407 Phase 2
0.6712 Remote Similarity NPD4889 Approved
0.6711 Remote Similarity NPD7187 Phase 2
0.6708 Remote Similarity NPD7688 Phase 1
0.6708 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6704 Remote Similarity NPD8426 Approved
0.6704 Remote Similarity NPD8459 Approved
0.6704 Remote Similarity NPD8460 Approved
0.6704 Remote Similarity NPD8425 Approved
0.6695 Remote Similarity NPD8356 Approved
0.6695 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6694 Remote Similarity NPD7807 Clinical (unspecified phase)
0.6693 Remote Similarity NPD6276 Discontinued
0.6679 Remote Similarity NPD8429 Approved
0.6679 Remote Similarity NPD8428 Approved
0.6679 Remote Similarity NPD8427 Approved
0.6667 Remote Similarity NPD6716 Phase 1
0.6653 Remote Similarity NPD4328 Approved
0.6653 Remote Similarity NPD6553 Clinical (unspecified phase)
0.6653 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6653 Remote Similarity NPD6292 Clinical (unspecified phase)
0.6653 Remote Similarity NPD8160 Phase 2
0.6652 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6652 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6652 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6651 Remote Similarity NPD3178 Discontinued
0.665 Remote Similarity NPD9074 Approved
0.665 Remote Similarity NPD9075 Approved
0.6641 Remote Similarity NPD8363 Approved
0.6641 Remote Similarity NPD8364 Approved
0.6639 Remote Similarity NPD7404 Approved
0.6638 Remote Similarity NPD8399 Phase 1
0.6638 Remote Similarity NPD7947 Clinical (unspecified phase)
0.6638 Remote Similarity NPD8423 Phase 2
0.6635 Remote Similarity NPD1631 Approved
0.6628 Remote Similarity NPD6228 Discontinued
0.6624 Remote Similarity NPD8404 Phase 2
0.6623 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6622 Remote Similarity NPD4602 Approved
0.6612 Remote Similarity NPD7426 Phase 1
0.661 Remote Similarity NPD8112 Clinical (unspecified phase)
0.661 Remote Similarity NPD4897 Phase 2
0.6609 Remote Similarity NPD6176 Phase 1
0.6607 Remote Similarity NPD6665 Discontinued
0.6603 Remote Similarity NPD2581 Approved
0.6603 Remote Similarity NPD2582 Approved
0.6597 Remote Similarity NPD7395 Discontinued
0.6597 Remote Similarity NPD3354 Phase 2
0.6597 Remote Similarity NPD4429 Discontinued
0.6596 Remote Similarity NPD3816 Phase 1
0.6596 Remote Similarity NPD3815 Phase 1
0.6592 Remote Similarity NPD2565 Phase 2
0.6592 Remote Similarity NPD6281 Approved
0.6592 Remote Similarity NPD2564 Approved
0.6591 Remote Similarity NPD8365 Clinical (unspecified phase)
0.659 Remote Similarity NPD5450 Discontinued
0.6589 Remote Similarity NPD1575 Approved
0.6589 Remote Similarity NPD1573 Approved
0.6584 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6584 Remote Similarity NPD8430 Approved
0.6583 Remote Similarity NPD5506 Approved
0.6583 Remote Similarity NPD5507 Approved
0.6581 Remote Similarity NPD6262 Clinical (unspecified phase)
0.6581 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6578 Remote Similarity NPD6361 Phase 2
0.6577 Remote Similarity NPD6791 Phase 2
0.6575 Remote Similarity NPD8101 Phase 3
0.6575 Remote Similarity NPD8368 Discontinued
0.6575 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6573 Remote Similarity NPD8409 Suspended
0.6564 Remote Similarity NPD6530 Approved
0.6564 Remote Similarity NPD6531 Approved
0.6564 Remote Similarity NPD6206 Phase 1
0.6562 Remote Similarity NPD8370 Discontinued
0.656 Remote Similarity NPD7576 Discontinued
0.6553 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6552 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6552 Remote Similarity NPD7957 Phase 1
0.655 Remote Similarity NPD4500 Approved
0.655 Remote Similarity NPD6479 Discontinued
0.655 Remote Similarity NPD4501 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