Structure

Physi-Chem Properties

Molecular Weight:  480.09
Volume:  430.728
LogP:  1.069
LogD:  0.33
LogS:  -2.876
# Rotatable Bonds:  5
TPSA:  212.67
# H-Bond Aceptor:  13
# H-Bond Donor:  7
# Rings:  4
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.223
Synthetic Accessibility Score:  4.258
Fsp3:  0.333
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.533
MDCK Permeability:  1.2862204130215105e-05
Pgp-inhibitor:  0.059
Pgp-substrate:  0.061
Human Intestinal Absorption (HIA):  0.821
20% Bioavailability (F20%):  0.07
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.086
Plasma Protein Binding (PPB):  90.48363494873047%
Volume Distribution (VD):  0.454
Pgp-substrate:  17.28925323486328%

ADMET: Metabolism

CYP1A2-inhibitor:  0.095
CYP1A2-substrate:  0.063
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.048
CYP2C9-inhibitor:  0.279
CYP2C9-substrate:  0.126
CYP2D6-inhibitor:  0.073
CYP2D6-substrate:  0.133
CYP3A4-inhibitor:  0.081
CYP3A4-substrate:  0.026

ADMET: Excretion

Clearance (CL):  9.983
Half-life (T1/2):  0.966

ADMET: Toxicity

hERG Blockers:  0.309
Human Hepatotoxicity (H-HT):  0.06
Drug-inuced Liver Injury (DILI):  0.918
AMES Toxicity:  0.266
Rat Oral Acute Toxicity:  0.003
Maximum Recommended Daily Dose:  0.01
Skin Sensitization:  0.918
Carcinogencity:  0.057
Eye Corrosion:  0.003
Eye Irritation:  0.901
Respiratory Toxicity:  0.023

Download Data

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

  Natural Product: NPC24627

Natural Product ID:  NPC24627
Common Name*:   11-O-Galloylbergenin
IUPAC Name:   [(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-9-methoxy-6-oxo-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-2-yl]methyl 3,4,5-trihydroxybenzoate
Synonyms:  
Standard InCHIKey:  CDRRULDABVKKHU-YQBPHPIXSA-N
Standard InCHI:  InChI=1S/C21H20O13/c1-31-17-10(24)4-7-12(15(17)27)18-19(34-21(7)30)16(28)14(26)11(33-18)5-32-20(29)6-2-8(22)13(25)9(23)3-6/h2-4,11,14,16,18-19,22-28H,5H2,1H3/t11-,14-,16+,18+,19-/m1/s1
SMILES:  COc1c(O)cc2c(c1O)[C@@H]1O[C@H](COC(=O)c3cc(O)c(c(c3)O)O)[C@H]([C@@H]([C@H]1OC2=O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1808739
PubChem CID:   56680102
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001248] Hydroxybenzoic acid derivatives
            • [CHEMONTID:0001251] Gallic acid and derivatives
              • [CHEMONTID:0003539] Galloyl esters

*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
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10757709]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. leaf n.a. PMID[10830513]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. twig n.a. PMID[10830513]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. n.a. n.a. PMID[10830513]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[12193039]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. leaf n.a. PMID[17685627]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota rhizomes n.a. n.a. PMID[21353549]
NPO13504 Lotus japonicus Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21510636]
NPO25715 Senna siamea Species Fabaceae Eukaryota Stems n.a. n.a. PMID[23078294]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[23210623]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23513740]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[30379546]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[31596079]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3199 Balanophora involucrata Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10012 Triaenophora rupestris Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25774 Virola multinervia Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6179 Aframomum amaniense Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7169 Nama hispidum Species Namaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14089 Hypericum ascyron Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7752 Beilschmiedia anacardioides Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12414 Penicillium paxilli Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10389 Larix cajanderi Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13701 Melaleuca rhaphiophylla Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10865 Sextonia rubra Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12069 Isaria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11882 Cedrus libani Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1661 Bartramia pomiformis Species Bartramiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3458 Lupinus verbasciformis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13907 Senecio renardii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14615 Streptomyces paulus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12910 Ixeris stolonifera Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12234 Khaya ivorensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13504 Lotus japonicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6774 Khaya senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14200 Aristolochia zollingeriana Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13076 Cephalaria grossheimii Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14504 Alectoria divergens Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21498 Coccus ilicis Species Coccidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12061 Justicia paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9669 Dictyopteris acrostichoides Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12754 Cerinthe minor Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2130 Ehretia dicksonii Species Ehretiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12585 Craspidospermum verticillatum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14289 Pieris napi Species Pieridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3199 Balanophora involucrata Species Balanophoraceae 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
NPT589 Individual Protein Serum albumin Bos taurus Inhibition = 22.22 % PMID[522973]
NPT589 Individual Protein Serum albumin Bos taurus IC50 = 183710.0 nM PMID[522973]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 1.5 % PMID[522973]
NPT35 Others n.a. Inhibition = 95.96 % PMID[522973]
NPT35 Others n.a. IC50 = 9060.0 nM PMID[522973]
NPT35 Others n.a. Inhibition = 102.22 % PMID[522973]
NPT35 Others n.a. IC50 = 0.000088 nM PMID[522973]
NPT35 Others n.a. Inhibition = 83.62 % PMID[522973]
NPT35 Others n.a. IC50 = 12280.0 nM PMID[522973]

☑ 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 NPC24627 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
0.9669 High Similarity NPC197188
0.9669 High Similarity NPC43872
0.9669 High Similarity NPC238672
0.9669 High Similarity NPC291510
0.9669 High Similarity NPC144801
0.9669 High Similarity NPC116850
0.9536 High Similarity NPC228662
0.9419 High Similarity NPC87317
0.9419 High Similarity NPC40702
0.9419 High Similarity NPC267627
0.9419 High Similarity NPC37502
0.9359 High Similarity NPC53889
0.9355 High Similarity NPC247713
0.9351 High Similarity NPC16082
0.9351 High Similarity NPC82592
0.929 High Similarity NPC300845
0.929 High Similarity NPC250436
0.929 High Similarity NPC291948
0.929 High Similarity NPC227062
0.929 High Similarity NPC104983
0.929 High Similarity NPC88803
0.9286 High Similarity NPC281477
0.9259 High Similarity NPC166674
0.9259 High Similarity NPC34436
0.9259 High Similarity NPC219600
0.9259 High Similarity NPC46640
0.9259 High Similarity NPC263119
0.9236 High Similarity NPC24164
0.9231 High Similarity NPC156818
0.9231 High Similarity NPC68324
0.9231 High Similarity NPC289322
0.9231 High Similarity NPC38779
0.9231 High Similarity NPC160512
0.9231 High Similarity NPC84935
0.9231 High Similarity NPC190020
0.9231 High Similarity NPC114179
0.9231 High Similarity NPC77679
0.9205 High Similarity NPC268366
0.9167 High Similarity NPC150227
0.9167 High Similarity NPC318432
0.9161 High Similarity NPC178134
0.9156 High Similarity NPC75695
0.9146 High Similarity NPC472723
0.9146 High Similarity NPC297574
0.9141 High Similarity NPC473550
0.9136 High Similarity NPC181778
0.9125 High Similarity NPC471788
0.9108 High Similarity NPC472860
0.9103 High Similarity NPC199926
0.9097 High Similarity NPC295646
0.9068 High Similarity NPC477517
0.9068 High Similarity NPC207575
0.9068 High Similarity NPC13481
0.9045 High Similarity NPC54928
0.9032 High Similarity NPC70016
0.9032 High Similarity NPC215921
0.9026 High Similarity NPC473091
0.902 High Similarity NPC81835
0.9012 High Similarity NPC117854
0.9012 High Similarity NPC477154
0.9012 High Similarity NPC474024
0.9012 High Similarity NPC6588
0.9012 High Similarity NPC298847
0.9007 High Similarity NPC121573
0.9007 High Similarity NPC22176
0.9007 High Similarity NPC190587
0.9007 High Similarity NPC226738
0.9006 High Similarity NPC142614
0.9 High Similarity NPC472964
0.9 High Similarity NPC476371
0.9 High Similarity NPC291957
0.9 High Similarity NPC476372
0.9 High Similarity NPC42797
0.9 High Similarity NPC14030
0.9 High Similarity NPC473445
0.8994 High Similarity NPC239966
0.8994 High Similarity NPC155101
0.8994 High Similarity NPC472902
0.8994 High Similarity NPC203020
0.8987 High Similarity NPC135222
0.8987 High Similarity NPC1913
0.8987 High Similarity NPC474010
0.8981 High Similarity NPC145425
0.8981 High Similarity NPC79998
0.8974 High Similarity NPC474656
0.8963 High Similarity NPC65333
0.8963 High Similarity NPC38438
0.8961 High Similarity NPC476394
0.8961 High Similarity NPC98809
0.8957 High Similarity NPC229687
0.8944 High Similarity NPC67959
0.8944 High Similarity NPC291977
0.8944 High Similarity NPC470898
0.8938 High Similarity NPC134783
0.8931 High Similarity NPC160780
0.8931 High Similarity NPC315157
0.8931 High Similarity NPC289811
0.8931 High Similarity NPC329091
0.8922 High Similarity NPC80956
0.8917 High Similarity NPC281703
0.8917 High Similarity NPC125487
0.8917 High Similarity NPC287504
0.8916 High Similarity NPC79736
0.8916 High Similarity NPC67629
0.8916 High Similarity NPC473713
0.891 High Similarity NPC272566
0.8896 High Similarity NPC116745
0.8896 High Similarity NPC142528
0.8896 High Similarity NPC14662
0.8896 High Similarity NPC472969
0.8896 High Similarity NPC473818
0.8896 High Similarity NPC45400
0.8889 High Similarity NPC293319
0.8882 High Similarity NPC33298
0.8882 High Similarity NPC285108
0.8882 High Similarity NPC474034
0.8882 High Similarity NPC220912
0.8882 High Similarity NPC148273
0.8882 High Similarity NPC474033
0.8875 High Similarity NPC200746
0.8875 High Similarity NPC166277
0.8875 High Similarity NPC474960
0.8875 High Similarity NPC36217
0.8875 High Similarity NPC174953
0.8875 High Similarity NPC474770
0.8875 High Similarity NPC119125
0.8875 High Similarity NPC472055
0.8875 High Similarity NPC476373
0.8869 High Similarity NPC125352
0.8869 High Similarity NPC208797
0.8869 High Similarity NPC170203
0.8869 High Similarity NPC53680
0.8868 High Similarity NPC129684
0.8868 High Similarity NPC299520
0.8868 High Similarity NPC300727
0.8868 High Similarity NPC241904
0.8862 High Similarity NPC267549
0.8861 High Similarity NPC203757
0.8861 High Similarity NPC38898
0.8861 High Similarity NPC67396
0.8861 High Similarity NPC20541
0.8854 High Similarity NPC178574
0.8854 High Similarity NPC65591
0.8854 High Similarity NPC167903
0.8848 High Similarity NPC100251
0.8848 High Similarity NPC271848
0.8848 High Similarity NPC262580
0.8848 High Similarity NPC289396
0.8848 High Similarity NPC81332
0.8848 High Similarity NPC472386
0.8848 High Similarity NPC212038
0.8846 High Similarity NPC96501
0.8841 High Similarity NPC183036
0.8839 High Similarity NPC107636
0.8834 High Similarity NPC175793
0.8834 High Similarity NPC5778
0.8834 High Similarity NPC236934
0.8834 High Similarity NPC20237
0.8834 High Similarity NPC472452
0.8827 High Similarity NPC475985
0.8827 High Similarity NPC248638
0.8827 High Similarity NPC152659
0.8827 High Similarity NPC7483
0.8827 High Similarity NPC186686
0.8827 High Similarity NPC249181
0.8827 High Similarity NPC121290
0.8827 High Similarity NPC474350
0.8827 High Similarity NPC236521
0.8824 High Similarity NPC207732
0.882 High Similarity NPC158188
0.882 High Similarity NPC311803
0.882 High Similarity NPC112418
0.882 High Similarity NPC109061
0.882 High Similarity NPC228383
0.882 High Similarity NPC472859
0.882 High Similarity NPC471212
0.882 High Similarity NPC26326
0.882 High Similarity NPC472632
0.882 High Similarity NPC25389
0.882 High Similarity NPC471211
0.882 High Similarity NPC173137
0.8817 High Similarity NPC129533
0.8817 High Similarity NPC123259
0.8812 High Similarity NPC476242
0.8812 High Similarity NPC473990
0.8812 High Similarity NPC470339
0.881 High Similarity NPC212290
0.8805 High Similarity NPC274730
0.8805 High Similarity NPC469474
0.8805 High Similarity NPC250922
0.8805 High Similarity NPC24640
0.8805 High Similarity NPC165483
0.8797 High Similarity NPC25127
0.8797 High Similarity NPC18727
0.8797 High Similarity NPC250557
0.8795 High Similarity NPC172033
0.8795 High Similarity NPC175230
0.8795 High Similarity NPC88560
0.8795 High Similarity NPC98583
0.8795 High Similarity NPC163165

  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 NPC24627 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
0.929 High Similarity NPD4868 Clinical (unspecified phase)
0.9161 High Similarity NPD1465 Phase 2
0.8848 High Similarity NPD7993 Clinical (unspecified phase)
0.8841 High Similarity NPD5844 Phase 1
0.8773 High Similarity NPD6167 Clinical (unspecified phase)
0.8773 High Similarity NPD6166 Phase 2
0.8773 High Similarity NPD6168 Clinical (unspecified phase)
0.8734 High Similarity NPD1934 Approved
0.8675 High Similarity NPD7074 Phase 3
0.865 High Similarity NPD6232 Discontinued
0.8614 High Similarity NPD7054 Approved
0.8563 High Similarity NPD7472 Approved
0.8562 High Similarity NPD2393 Clinical (unspecified phase)
0.8554 High Similarity NPD3818 Discontinued
0.8554 High Similarity NPD7228 Approved
0.8521 High Similarity NPD4338 Clinical (unspecified phase)
0.8494 Intermediate Similarity NPD7473 Discontinued
0.8491 Intermediate Similarity NPD4380 Phase 2
0.8466 Intermediate Similarity NPD6234 Discontinued
0.8447 Intermediate Similarity NPD2801 Approved
0.8402 Intermediate Similarity NPD6797 Phase 2
0.8395 Intermediate Similarity NPD3817 Phase 2
0.8385 Intermediate Similarity NPD37 Approved
0.8353 Intermediate Similarity NPD7251 Discontinued
0.8344 Intermediate Similarity NPD230 Phase 1
0.8344 Intermediate Similarity NPD4965 Approved
0.8344 Intermediate Similarity NPD3882 Suspended
0.8344 Intermediate Similarity NPD4966 Approved
0.8344 Intermediate Similarity NPD4967 Phase 2
0.8333 Intermediate Similarity NPD7819 Suspended
0.8304 Intermediate Similarity NPD7808 Phase 3
0.8303 Intermediate Similarity NPD5494 Approved
0.8293 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8293 Intermediate Similarity NPD7075 Discontinued
0.8161 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8153 Intermediate Similarity NPD3750 Approved
0.8144 Intermediate Similarity NPD7199 Phase 2
0.8144 Intermediate Similarity NPD6959 Discontinued
0.8141 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.814 Intermediate Similarity NPD7685 Pre-registration
0.8113 Intermediate Similarity NPD1511 Approved
0.811 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8101 Intermediate Similarity NPD6190 Approved
0.8075 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8063 Intermediate Similarity NPD2532 Approved
0.8063 Intermediate Similarity NPD2534 Approved
0.8063 Intermediate Similarity NPD2533 Approved
0.8061 Intermediate Similarity NPD5402 Approved
0.8049 Intermediate Similarity NPD6801 Discontinued
0.8038 Intermediate Similarity NPD4628 Phase 3
0.8035 Intermediate Similarity NPD7240 Approved
0.8023 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD1512 Approved
0.7988 Intermediate Similarity NPD7411 Suspended
0.7965 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD3027 Phase 3
0.7941 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7933 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7922 Intermediate Similarity NPD1613 Approved
0.7922 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD1653 Approved
0.7911 Intermediate Similarity NPD1549 Phase 2
0.7888 Intermediate Similarity NPD6799 Approved
0.7857 Intermediate Similarity NPD3749 Approved
0.7853 Intermediate Similarity NPD5403 Approved
0.7848 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7848 Intermediate Similarity NPD7266 Discontinued
0.7848 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7844 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7834 Intermediate Similarity NPD1510 Phase 2
0.7834 Intermediate Similarity NPD3748 Approved
0.7829 Intermediate Similarity NPD6559 Discontinued
0.7818 Intermediate Similarity NPD6599 Discontinued
0.7791 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD8151 Discontinued
0.7778 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD8313 Approved
0.774 Intermediate Similarity NPD8312 Approved
0.7738 Intermediate Similarity NPD5353 Approved
0.7733 Intermediate Similarity NPD5242 Approved
0.773 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD5401 Approved
0.7712 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD3751 Discontinued
0.7692 Intermediate Similarity NPD943 Approved
0.7692 Intermediate Similarity NPD1240 Approved
0.7692 Intermediate Similarity NPD7768 Phase 2
0.7677 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD2935 Discontinued
0.7673 Intermediate Similarity NPD2796 Approved
0.7662 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD9269 Phase 2
0.7611 Intermediate Similarity NPD8150 Discontinued
0.7597 Intermediate Similarity NPD9494 Approved
0.7595 Intermediate Similarity NPD1607 Approved
0.7593 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD3787 Discontinued
0.7572 Intermediate Similarity NPD5710 Approved
0.7572 Intermediate Similarity NPD5711 Approved
0.7545 Intermediate Similarity NPD3226 Approved
0.7532 Intermediate Similarity NPD447 Suspended
0.7529 Intermediate Similarity NPD3926 Phase 2
0.7514 Intermediate Similarity NPD8127 Discontinued
0.7513 Intermediate Similarity NPD7680 Approved
0.7513 Intermediate Similarity NPD7435 Discontinued
0.75 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD919 Approved
0.7485 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD8455 Phase 2
0.7456 Intermediate Similarity NPD6386 Approved
0.7456 Intermediate Similarity NPD6385 Approved
0.7453 Intermediate Similarity NPD6099 Approved
0.7453 Intermediate Similarity NPD1551 Phase 2
0.7453 Intermediate Similarity NPD6100 Approved
0.7452 Intermediate Similarity NPD3764 Approved
0.7447 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD6780 Approved
0.7447 Intermediate Similarity NPD6778 Approved
0.7447 Intermediate Similarity NPD6776 Approved
0.7447 Intermediate Similarity NPD6782 Approved
0.7447 Intermediate Similarity NPD6781 Approved
0.7447 Intermediate Similarity NPD6777 Approved
0.7447 Intermediate Similarity NPD6779 Approved
0.7418 Intermediate Similarity NPD8434 Phase 2
0.741 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD2346 Discontinued
0.7403 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD7229 Phase 3
0.7365 Intermediate Similarity NPD6273 Approved
0.7351 Intermediate Similarity NPD9268 Approved
0.7349 Intermediate Similarity NPD7390 Discontinued
0.7338 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7458 Discontinued
0.7333 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7783 Phase 2
0.733 Intermediate Similarity NPD7697 Approved
0.733 Intermediate Similarity NPD7696 Phase 3
0.733 Intermediate Similarity NPD7698 Approved
0.7326 Intermediate Similarity NPD4288 Approved
0.7325 Intermediate Similarity NPD4908 Phase 1
0.7314 Intermediate Similarity NPD1247 Approved
0.7312 Intermediate Similarity NPD1933 Approved
0.7282 Intermediate Similarity NPD7874 Approved
0.7282 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD5953 Discontinued
0.7273 Intermediate Similarity NPD7003 Approved
0.7273 Intermediate Similarity NPD8166 Discontinued
0.7268 Intermediate Similarity NPD7701 Phase 2
0.7251 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD4060 Phase 1
0.7233 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD6798 Discontinued
0.7219 Intermediate Similarity NPD920 Approved
0.7212 Intermediate Similarity NPD6674 Discontinued
0.7212 Intermediate Similarity NPD1652 Phase 2
0.7212 Intermediate Similarity NPD2800 Approved
0.7205 Intermediate Similarity NPD5124 Phase 1
0.7205 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD6355 Discontinued
0.7202 Intermediate Similarity NPD7870 Phase 2
0.7202 Intermediate Similarity NPD7871 Phase 2
0.7202 Intermediate Similarity NPD8320 Phase 1
0.7202 Intermediate Similarity NPD8319 Approved
0.7198 Intermediate Similarity NPD7549 Discontinued
0.7196 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD6823 Phase 2
0.7181 Intermediate Similarity NPD6534 Approved
0.7181 Intermediate Similarity NPD6535 Approved
0.7178 Intermediate Similarity NPD7033 Discontinued
0.7178 Intermediate Similarity NPD2799 Discontinued
0.7171 Intermediate Similarity NPD9545 Approved
0.7167 Intermediate Similarity NPD7286 Phase 2
0.7161 Intermediate Similarity NPD1608 Approved
0.7158 Intermediate Similarity NPD7699 Phase 2
0.7158 Intermediate Similarity NPD7700 Phase 2
0.7143 Intermediate Similarity NPD7038 Approved
0.7143 Intermediate Similarity NPD7039 Approved
0.7135 Intermediate Similarity NPD3455 Phase 2
0.7134 Intermediate Similarity NPD5408 Approved
0.7134 Intermediate Similarity NPD2797 Approved
0.7134 Intermediate Similarity NPD2438 Suspended
0.7134 Intermediate Similarity NPD5406 Approved
0.7134 Intermediate Similarity NPD5404 Approved
0.7134 Intermediate Similarity NPD5405 Approved
0.7125 Intermediate Similarity NPD3268 Approved
0.7111 Intermediate Similarity NPD7177 Discontinued
0.7108 Intermediate Similarity NPD1243 Approved
0.7107 Intermediate Similarity NPD6832 Phase 2
0.7101 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD5005 Approved
0.7098 Intermediate Similarity NPD5006 Approved
0.7097 Intermediate Similarity NPD1610 Phase 2
0.7092 Intermediate Similarity NPD7585 Approved
0.7081 Intermediate Similarity NPD6233 Phase 2

  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