Structure

Physi-Chem Properties

Molecular Weight:  898.49
Volume:  873.961
LogP:  1.29
LogD:  2.106
LogS:  -4.343
# Rotatable Bonds:  8
TPSA:  263.75
# H-Bond Aceptor:  17
# H-Bond Donor:  9
# Rings:  9
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.117
Synthetic Accessibility Score:  7.621
Fsp3:  0.978
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.91
MDCK Permeability:  2.303130349901039e-05
Pgp-inhibitor:  0.116
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.954
20% Bioavailability (F20%):  0.013
30% Bioavailability (F30%):  0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.069
Plasma Protein Binding (PPB):  57.20892333984375%
Volume Distribution (VD):  0.506
Pgp-substrate:  22.639951705932617%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.97
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.255
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.003
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.029
CYP3A4-inhibitor:  0.257
CYP3A4-substrate:  0.023

ADMET: Excretion

Clearance (CL):  0.673
Half-life (T1/2):  0.701

ADMET: Toxicity

hERG Blockers:  0.347
Human Hepatotoxicity (H-HT):  0.265
Drug-inuced Liver Injury (DILI):  0.007
AMES Toxicity:  0.091
Rat Oral Acute Toxicity:  0.145
Maximum Recommended Daily Dose:  0.909
Skin Sensitization:  0.918
Carcinogencity:  0.028
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.981

Download Data

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

  Natural Product: NPC119628

Natural Product ID:  NPC119628
Common Name*:   Primulanin
IUPAC Name:   n.a.
Synonyms:   Primulanin
Standard InCHIKey:  JFAKXPCWZPQXLP-KASLOCEDSA-N
Standard InCHI:  InChI=1S/C46H74O17/c1-40(2)25-7-11-43(5)26(8-12-46-27-15-41(3,20-48)13-14-45(27,21-59-46)28(50)16-44(43,46)6)42(25,4)10-9-29(40)62-37-35(56)32(53)24(19-58-37)61-39-36(33(54)31(52)23(17-47)60-39)63-38-34(55)30(51)22(49)18-57-38/h20,22-39,47,49-56H,7-19,21H2,1-6H3/t22-,23-,24+,25+,26-,27-,28-,29+,30+,31-,32+,33+,34-,35-,36-,37+,38+,39+,41+,42+,43-,44+,45-,46+/m1/s1
SMILES:  CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC[C@]45[C@@H]6C[C@](C)(CC[C@]6(CO5)[C@@H](C[C@@]34C)O)C=O)[C@@]2(C)CC[C@@H]1O[C@H]1[C@@H]([C@H]([C@H](CO1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL218412
PubChem CID:   44419565
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO3803 Ardisia japonica Species Primulaceae Eukaryota whole plants Sendai, Miyagi Prefecture, Japan 2000-Sep PMID[17243725]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. whole plant n.a. PMID[17243725]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. whole plant n.a. PMID[17397219]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[22940450]
NPO32586 ardisia gigantifolia stapf. Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[24095094]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26639 Ardisia crenata Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11230 Herba glechomae longitubae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO26639 Ardisia crenata Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26639 Ardisia crenata Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26639 Ardisia crenata Species Primulaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 24700.0 nM PMID[556292]
NPT81 Cell Line A549 Homo sapiens IC50 = 27700.0 nM PMID[556292]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 100000000.0 nM PMID[556293]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 = 4050000.0 nM PMID[556293]
NPT180 Cell Line HCT-8 Homo sapiens IC50 = 8430.0 nM PMID[556294]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 = 10270.0 nM PMID[556294]
NPT81 Cell Line A549 Homo sapiens IC50 = 12020.0 nM PMID[556294]
NPT27 Others Unspecified IC50 = 3300.0 nM PMID[556292]
NPT27 Others Unspecified IC50 > 100000000.0 nM PMID[556293]

☑ 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 NPC119628 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 NPC158367
1.0 High Similarity NPC158051
0.9898 High Similarity NPC138219
0.9898 High Similarity NPC40716
0.9898 High Similarity NPC475630
0.9898 High Similarity NPC475234
0.9798 High Similarity NPC231566
0.9798 High Similarity NPC262567
0.9798 High Similarity NPC471626
0.9798 High Similarity NPC473688
0.9604 High Similarity NPC471431
0.9505 High Similarity NPC87393
0.95 High Similarity NPC126753
0.9417 High Similarity NPC157571
0.9412 High Similarity NPC66513
0.9109 High Similarity NPC267637
0.9038 High Similarity NPC470622
0.9029 High Similarity NPC207693
0.902 High Similarity NPC184805
0.902 High Similarity NPC273189
0.8942 High Similarity NPC22709
0.8932 High Similarity NPC471430
0.8911 High Similarity NPC80640
0.8866 High Similarity NPC224003
0.8866 High Similarity NPC171741
0.8866 High Similarity NPC18724
0.8866 High Similarity NPC470623
0.8866 High Similarity NPC323231
0.8846 High Similarity NPC469826
0.88 High Similarity NPC209798
0.88 High Similarity NPC471374
0.88 High Similarity NPC471375
0.8776 High Similarity NPC77717
0.8776 High Similarity NPC471373
0.8776 High Similarity NPC148593
0.8776 High Similarity NPC267238
0.8776 High Similarity NPC253611
0.8713 High Similarity NPC471428
0.8713 High Similarity NPC51579
0.8713 High Similarity NPC80417
0.8713 High Similarity NPC471426
0.8713 High Similarity NPC471427
0.8704 High Similarity NPC477465
0.8687 High Similarity NPC471424
0.8687 High Similarity NPC205129
0.8687 High Similarity NPC471425
0.8687 High Similarity NPC106701
0.8687 High Similarity NPC471429
0.8687 High Similarity NPC189575
0.8598 High Similarity NPC469824
0.8585 High Similarity NPC228190
0.8585 High Similarity NPC236753
0.8558 High Similarity NPC469827
0.8519 High Similarity NPC477492
0.8491 Intermediate Similarity NPC202898
0.8491 Intermediate Similarity NPC92890
0.8491 Intermediate Similarity NPC475319
0.8476 Intermediate Similarity NPC215408
0.8447 Intermediate Similarity NPC477172
0.8411 Intermediate Similarity NPC233433
0.8411 Intermediate Similarity NPC273002
0.8411 Intermediate Similarity NPC473817
0.8411 Intermediate Similarity NPC469825
0.8411 Intermediate Similarity NPC220836
0.8411 Intermediate Similarity NPC94086
0.8411 Intermediate Similarity NPC92297
0.8396 Intermediate Similarity NPC203974
0.8378 Intermediate Similarity NPC179429
0.8365 Intermediate Similarity NPC80191
0.8365 Intermediate Similarity NPC310031
0.8333 Intermediate Similarity NPC472273
0.8286 Intermediate Similarity NPC34562
0.8218 Intermediate Similarity NPC305418
0.8198 Intermediate Similarity NPC79193
0.8182 Intermediate Similarity NPC477489
0.8173 Intermediate Similarity NPC20028
0.8125 Intermediate Similarity NPC137414
0.81 Intermediate Similarity NPC18536
0.81 Intermediate Similarity NPC50443
0.8091 Intermediate Similarity NPC204392
0.8091 Intermediate Similarity NPC275668
0.8091 Intermediate Similarity NPC240734
0.8091 Intermediate Similarity NPC1876
0.8091 Intermediate Similarity NPC91838
0.8077 Intermediate Similarity NPC472144
0.8058 Intermediate Similarity NPC203434
0.8058 Intermediate Similarity NPC238796
0.8058 Intermediate Similarity NPC304011
0.8058 Intermediate Similarity NPC237071
0.8058 Intermediate Similarity NPC139271
0.8058 Intermediate Similarity NPC475765
0.8058 Intermediate Similarity NPC475785
0.8037 Intermediate Similarity NPC470167
0.802 Intermediate Similarity NPC307167
0.802 Intermediate Similarity NPC210759
0.802 Intermediate Similarity NPC229801
0.8 Intermediate Similarity NPC41843
0.8 Intermediate Similarity NPC131466
0.7982 Intermediate Similarity NPC475899
0.7982 Intermediate Similarity NPC469822
0.7981 Intermediate Similarity NPC472145
0.7981 Intermediate Similarity NPC470591
0.7961 Intermediate Similarity NPC94582
0.7961 Intermediate Similarity NPC477494
0.7961 Intermediate Similarity NPC57964
0.7946 Intermediate Similarity NPC146563
0.7944 Intermediate Similarity NPC107385
0.7941 Intermediate Similarity NPC172838
0.7941 Intermediate Similarity NPC137004
0.7928 Intermediate Similarity NPC473062
0.7925 Intermediate Similarity NPC475574
0.7921 Intermediate Similarity NPC185529
0.7921 Intermediate Similarity NPC472146
0.7913 Intermediate Similarity NPC477464
0.7909 Intermediate Similarity NPC51947
0.7909 Intermediate Similarity NPC473844
0.7895 Intermediate Similarity NPC323359
0.7885 Intermediate Similarity NPC235109
0.7885 Intermediate Similarity NPC121453
0.7879 Intermediate Similarity NPC471410
0.7879 Intermediate Similarity NPC471411
0.7876 Intermediate Similarity NPC469821
0.7864 Intermediate Similarity NPC45959
0.7864 Intermediate Similarity NPC174024
0.7864 Intermediate Similarity NPC131693
0.7864 Intermediate Similarity NPC179859
0.7864 Intermediate Similarity NPC291203
0.7864 Intermediate Similarity NPC252253
0.7864 Intermediate Similarity NPC291547
0.7864 Intermediate Similarity NPC475436
0.7864 Intermediate Similarity NPC473851
0.7864 Intermediate Similarity NPC253268
0.7864 Intermediate Similarity NPC217205
0.7864 Intermediate Similarity NPC312678
0.7857 Intermediate Similarity NPC324875
0.7857 Intermediate Similarity NPC276093
0.7857 Intermediate Similarity NPC473373
0.7857 Intermediate Similarity NPC475504
0.7857 Intermediate Similarity NPC109079
0.7857 Intermediate Similarity NPC79718
0.7857 Intermediate Similarity NPC257468
0.7857 Intermediate Similarity NPC292677
0.7857 Intermediate Similarity NPC104071
0.7857 Intermediate Similarity NPC469946
0.7857 Intermediate Similarity NPC104400
0.7857 Intermediate Similarity NPC10320
0.7857 Intermediate Similarity NPC139044
0.7857 Intermediate Similarity NPC101744
0.7857 Intermediate Similarity NPC475516
0.7857 Intermediate Similarity NPC102439
0.7857 Intermediate Similarity NPC471383
0.7845 Intermediate Similarity NPC144644
0.7845 Intermediate Similarity NPC473645
0.7845 Intermediate Similarity NPC142151
0.7845 Intermediate Similarity NPC153673
0.7845 Intermediate Similarity NPC37860
0.7845 Intermediate Similarity NPC110385
0.7845 Intermediate Similarity NPC267694
0.7843 Intermediate Similarity NPC475878
0.7826 Intermediate Similarity NPC18233
0.7826 Intermediate Similarity NPC276758
0.7826 Intermediate Similarity NPC232237
0.7826 Intermediate Similarity NPC473459
0.7826 Intermediate Similarity NPC105800
0.7822 Intermediate Similarity NPC82955
0.7818 Intermediate Similarity NPC88744
0.7818 Intermediate Similarity NPC472079
0.781 Intermediate Similarity NPC477223
0.781 Intermediate Similarity NPC307534
0.781 Intermediate Similarity NPC274200
0.781 Intermediate Similarity NPC476112
0.781 Intermediate Similarity NPC210157
0.781 Intermediate Similarity NPC477222
0.7807 Intermediate Similarity NPC160415
0.7807 Intermediate Similarity NPC58448
0.7807 Intermediate Similarity NPC469823
0.7807 Intermediate Similarity NPC472718
0.7807 Intermediate Similarity NPC469820
0.78 Intermediate Similarity NPC140446
0.78 Intermediate Similarity NPC43912
0.7797 Intermediate Similarity NPC30735
0.7797 Intermediate Similarity NPC44716
0.7797 Intermediate Similarity NPC235405
0.7797 Intermediate Similarity NPC2370
0.7797 Intermediate Similarity NPC281148
0.7788 Intermediate Similarity NPC473826
0.7788 Intermediate Similarity NPC323341
0.7788 Intermediate Similarity NPC192600
0.7788 Intermediate Similarity NPC134835
0.7788 Intermediate Similarity NPC241909
0.7788 Intermediate Similarity NPC82633
0.7788 Intermediate Similarity NPC114304
0.7788 Intermediate Similarity NPC46665
0.7788 Intermediate Similarity NPC475467
0.7788 Intermediate Similarity NPC295823
0.7788 Intermediate Similarity NPC114287
0.7788 Intermediate Similarity NPC107188
0.7788 Intermediate Similarity NPC474399
0.7788 Intermediate Similarity NPC73318
0.7788 Intermediate Similarity NPC473610

  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 NPC119628 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
0.8558 High Similarity NPD8170 Clinical (unspecified phase)
0.7788 Intermediate Similarity NPD8133 Approved
0.7767 Intermediate Similarity NPD8171 Discontinued
0.7586 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD8328 Phase 3
0.7281 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD7507 Approved
0.6929 Remote Similarity NPD7319 Approved
0.6731 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6731 Remote Similarity NPD3669 Approved
0.6699 Remote Similarity NPD1779 Approved
0.6699 Remote Similarity NPD1780 Approved
0.6694 Remote Similarity NPD8377 Approved
0.6694 Remote Similarity NPD8294 Approved
0.6667 Remote Similarity NPD6412 Phase 2
0.664 Remote Similarity NPD8378 Approved
0.664 Remote Similarity NPD8517 Approved
0.664 Remote Similarity NPD8335 Approved
0.664 Remote Similarity NPD8380 Approved
0.664 Remote Similarity NPD8379 Approved
0.664 Remote Similarity NPD8513 Phase 3
0.664 Remote Similarity NPD8516 Approved
0.664 Remote Similarity NPD8515 Approved
0.664 Remote Similarity NPD8296 Approved
0.6639 Remote Similarity NPD6940 Discontinued
0.661 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6602 Remote Similarity NPD6928 Phase 2
0.66 Remote Similarity NPD3703 Phase 2
0.6589 Remote Similarity NPD7736 Approved
0.6569 Remote Similarity NPD6115 Approved
0.6569 Remote Similarity NPD6118 Approved
0.6569 Remote Similarity NPD6114 Approved
0.6569 Remote Similarity NPD6697 Approved
0.6508 Remote Similarity NPD8033 Approved
0.65 Remote Similarity NPD1811 Approved
0.65 Remote Similarity NPD1810 Approved
0.6471 Remote Similarity NPD6686 Approved
0.6471 Remote Similarity NPD6116 Phase 1
0.6457 Remote Similarity NPD6370 Approved
0.64 Remote Similarity NPD7328 Approved
0.64 Remote Similarity NPD7327 Approved
0.6385 Remote Similarity NPD8293 Discontinued
0.6373 Remote Similarity NPD6117 Approved
0.6349 Remote Similarity NPD7516 Approved
0.6299 Remote Similarity NPD6054 Approved
0.6299 Remote Similarity NPD6059 Approved
0.625 Remote Similarity NPD8034 Phase 2
0.625 Remote Similarity NPD8035 Phase 2
0.62 Remote Similarity NPD2687 Approved
0.62 Remote Similarity NPD2254 Approved
0.62 Remote Similarity NPD7532 Clinical (unspecified phase)
0.62 Remote Similarity NPD2686 Approved
0.6186 Remote Similarity NPD8139 Approved
0.6186 Remote Similarity NPD8085 Approved
0.6186 Remote Similarity NPD8138 Approved
0.6186 Remote Similarity NPD8086 Approved
0.6186 Remote Similarity NPD8084 Approved
0.6186 Remote Similarity NPD8082 Approved
0.6186 Remote Similarity NPD8083 Approved
0.6176 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6167 Remote Similarity NPD8393 Approved
0.6148 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6139 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6139 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6134 Remote Similarity NPD8276 Approved
0.6134 Remote Similarity NPD8275 Approved
0.6124 Remote Similarity NPD6921 Approved
0.6124 Remote Similarity NPD6015 Approved
0.6124 Remote Similarity NPD6016 Approved
0.6107 Remote Similarity NPD7492 Approved
0.6102 Remote Similarity NPD1700 Approved
0.61 Remote Similarity NPD3699 Clinical (unspecified phase)
0.61 Remote Similarity NPD4267 Clinical (unspecified phase)
0.61 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6083 Remote Similarity NPD8081 Approved
0.6078 Remote Similarity NPD3181 Approved
0.6077 Remote Similarity NPD5988 Approved
0.6061 Remote Similarity NPD6616 Approved
0.6048 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6038 Remote Similarity NPD7329 Approved
0.6015 Remote Similarity NPD7078 Approved
0.6 Remote Similarity NPD7503 Approved
0.6 Remote Similarity NPD6882 Approved
0.6 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6 Remote Similarity NPD8297 Approved
0.6 Remote Similarity NPD7748 Approved
0.5984 Remote Similarity NPD8307 Discontinued
0.5984 Remote Similarity NPD8140 Approved
0.5983 Remote Similarity NPD7902 Approved
0.5968 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5962 Remote Similarity NPD3702 Approved
0.595 Remote Similarity NPD4057 Clinical (unspecified phase)
0.595 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5948 Remote Similarity NPD7991 Discontinued
0.5938 Remote Similarity NPD6009 Approved
0.5923 Remote Similarity NPD6319 Approved
0.5909 Remote Similarity NPD6067 Discontinued
0.5887 Remote Similarity NPD8305 Approved
0.5887 Remote Similarity NPD8306 Approved
0.5882 Remote Similarity NPD4244 Approved
0.5882 Remote Similarity NPD4245 Approved
0.5852 Remote Similarity NPD6033 Approved
0.5842 Remote Similarity NPD5361 Clinical (unspecified phase)
0.5842 Remote Similarity NPD5360 Phase 3
0.584 Remote Similarity NPD8087 Discontinued
0.5827 Remote Similarity NPD4632 Approved
0.5826 Remote Similarity NPD7515 Phase 2
0.5784 Remote Similarity NPD3698 Phase 2
0.5778 Remote Similarity NPD8074 Phase 3
0.5772 Remote Similarity NPD7128 Approved
0.5772 Remote Similarity NPD6402 Approved
0.5772 Remote Similarity NPD6675 Approved
0.5772 Remote Similarity NPD5739 Approved
0.576 Remote Similarity NPD6372 Approved
0.576 Remote Similarity NPD6373 Approved
0.5758 Remote Similarity NPD371 Approved
0.5728 Remote Similarity NPD4789 Approved
0.5726 Remote Similarity NPD7900 Approved
0.5726 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5726 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5692 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5682 Remote Similarity NPD8347 Approved
0.5682 Remote Similarity NPD8346 Approved
0.5682 Remote Similarity NPD8345 Approved
0.568 Remote Similarity NPD7320 Approved
0.568 Remote Similarity NPD6881 Approved
0.568 Remote Similarity NPD6899 Approved
0.568 Remote Similarity NPD8174 Phase 2
0.5673 Remote Similarity NPD5777 Approved
0.5669 Remote Similarity NPD8130 Phase 1
0.5669 Remote Similarity NPD6650 Approved
0.5669 Remote Similarity NPD6649 Approved
0.5667 Remote Similarity NPD7638 Approved
0.5648 Remote Similarity NPD3671 Phase 1
0.5643 Remote Similarity NPD8450 Suspended
0.562 Remote Similarity NPD7640 Approved
0.562 Remote Similarity NPD7639 Approved
0.562 Remote Similarity NPD8418 Phase 2
0.5612 Remote Similarity NPD6123 Approved
0.56 Remote Similarity NPD7909 Approved
0.56 Remote Similarity NPD5701 Approved
0.56 Remote Similarity NPD5697 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