Structure

Physi-Chem Properties

Molecular Weight:  462.37
Volume:  526.199
LogP:  10.719
LogD:  4.281
LogS:  -4.81
# Rotatable Bonds:  23
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.102
Synthetic Accessibility Score:  2.242
Fsp3:  0.759
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.241
MDCK Permeability:  7.618463769176742e-06
Pgp-inhibitor:  0.009
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.999
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.006
Plasma Protein Binding (PPB):  101.08877563476562%
Volume Distribution (VD):  6.069
Pgp-substrate:  0.6850062608718872%

ADMET: Metabolism

CYP1A2-inhibitor:  0.079
CYP1A2-substrate:  0.146
CYP2C19-inhibitor:  0.327
CYP2C19-substrate:  0.044
CYP2C9-inhibitor:  0.054
CYP2C9-substrate:  0.98
CYP2D6-inhibitor:  0.484
CYP2D6-substrate:  0.073
CYP3A4-inhibitor:  0.193
CYP3A4-substrate:  0.022

ADMET: Excretion

Clearance (CL):  5.506
Half-life (T1/2):  0.123

ADMET: Toxicity

hERG Blockers:  0.171
Human Hepatotoxicity (H-HT):  0.002
Drug-inuced Liver Injury (DILI):  0.095
AMES Toxicity:  0.031
Rat Oral Acute Toxicity:  0.007
Maximum Recommended Daily Dose:  0.01
Skin Sensitization:  0.972
Carcinogencity:  0.04
Eye Corrosion:  0.666
Eye Irritation:  0.959
Respiratory Toxicity:  0.359

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

  Natural Product: NPC295406

Natural Product ID:  NPC295406
Common Name*:   Gentiside J
IUPAC Name:   docosyl 2,3-dihydroxybenzoate
Synonyms:   Gentiside J
Standard InCHIKey:  ZYHQORYZNVHDNT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C29H50O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-33-29(32)26-23-22-24-27(30)28(26)31/h22-24,30-31H,2-21,25H2,1H3
SMILES:  CCCCCCCCCCCCCCCCCCCCCCOC(=O)c1cccc(c1O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1254431
PubChem CID:   14177660
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001350] Benzoic acid esters
            • [CHEMONTID:0004699] m-Hydroxybenzoic acid 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
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota roots n.a. n.a. PMID[17375953]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[20813533]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. leaf n.a. PMID[21043460]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[21043460]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. stem n.a. PMID[21043460]
NPO27624 Swartzia simplex Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26654828]
NPO12009 Abies pinsapo Species Pinaceae Eukaryota Wood n.a. n.a. PMID[7931362]
NPO18843 Antirrhinum majus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16073 Sarcomelicope megistophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19120 Strychnos aculeata Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15856 Podocarpus hallii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16646 Artemisia campestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17368 Erythrina senegalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17368 Erythrina senegalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16073 Sarcomelicope megistophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16646 Artemisia campestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18843 Antirrhinum majus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19120 Strychnos aculeata Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15856 Podocarpus hallii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16817 Aglaia argentea Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15856 Podocarpus hallii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18843 Antirrhinum majus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16646 Artemisia campestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16646 Artemisia campestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3046 Schisandra bicolor Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17699 Solanum glaucophyllum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17054 Streptomyces gardneri Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16958 Jurinea albicaulis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18372 Lobophytum crassospiculatum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18843 Antirrhinum majus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15518 Streptomyces netropsis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16817 Aglaia argentea Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13251 Iris nertchinskia Species Tarachodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12009 Abies pinsapo Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19120 Strychnos aculeata Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15856 Podocarpus hallii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18511 Latimeria chalumnae Species Coelacanthidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17368 Erythrina senegalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14721 Dentitheca habereri Species Plumulariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17711 Sphenoclea zeylanica Species Sphenocleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27624 Swartzia simplex Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16073 Sarcomelicope megistophylla Species Rutaceae 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
NPT681 Cell Line PC-12 Rattus norvegicus Activity = 67.0 % PMID[517756]

☑ 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 NPC295406 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 NPC157478
1.0 High Similarity NPC200422
1.0 High Similarity NPC289572
0.9844 High Similarity NPC204257
0.9844 High Similarity NPC254832
0.9844 High Similarity NPC29317
0.9844 High Similarity NPC229638
0.9844 High Similarity NPC176102
0.9844 High Similarity NPC71108
0.9844 High Similarity NPC267539
0.8889 High Similarity NPC260837
0.881 High Similarity NPC90522
0.881 High Similarity NPC328459
0.8797 High Similarity NPC7012
0.875 High Similarity NPC156892
0.874 High Similarity NPC72977
0.873 High Similarity NPC94637
0.8686 High Similarity NPC62907
0.8676 High Similarity NPC18646
0.8667 High Similarity NPC43627
0.8667 High Similarity NPC472591
0.8647 High Similarity NPC226855
0.8636 High Similarity NPC71525
0.8603 High Similarity NPC106406
0.8603 High Similarity NPC474097
0.8571 High Similarity NPC128825
0.8561 High Similarity NPC471819
0.8542 High Similarity NPC55327
0.8531 High Similarity NPC85734
0.8531 High Similarity NPC32058
0.8529 High Similarity NPC304929
0.8529 High Similarity NPC239855
0.8529 High Similarity NPC1321
0.8529 High Similarity NPC156124
0.8507 High Similarity NPC261759
0.8496 Intermediate Similarity NPC158654
0.8489 Intermediate Similarity NPC197666
0.8489 Intermediate Similarity NPC112135
0.8489 Intermediate Similarity NPC126739
0.8485 Intermediate Similarity NPC240744
0.8485 Intermediate Similarity NPC167055
0.8478 Intermediate Similarity NPC475111
0.8456 Intermediate Similarity NPC470160
0.8451 Intermediate Similarity NPC258307
0.845 Intermediate Similarity NPC233282
0.844 Intermediate Similarity NPC130485
0.8438 Intermediate Similarity NPC203124
0.8429 Intermediate Similarity NPC134969
0.8413 Intermediate Similarity NPC81808
0.8409 Intermediate Similarity NPC91475
0.8409 Intermediate Similarity NPC265910
0.8397 Intermediate Similarity NPC477151
0.8397 Intermediate Similarity NPC132518
0.8394 Intermediate Similarity NPC475468
0.8385 Intermediate Similarity NPC35856
0.8385 Intermediate Similarity NPC159760
0.8385 Intermediate Similarity NPC222876
0.8385 Intermediate Similarity NPC179092
0.8385 Intermediate Similarity NPC272454
0.8385 Intermediate Similarity NPC301987
0.8385 Intermediate Similarity NPC115188
0.8385 Intermediate Similarity NPC26433
0.8385 Intermediate Similarity NPC178395
0.8385 Intermediate Similarity NPC292665
0.8385 Intermediate Similarity NPC244994
0.8382 Intermediate Similarity NPC264145
0.8378 Intermediate Similarity NPC472128
0.8378 Intermediate Similarity NPC472127
0.8369 Intermediate Similarity NPC158472
0.8359 Intermediate Similarity NPC28169
0.8346 Intermediate Similarity NPC287473
0.8346 Intermediate Similarity NPC4164
0.8333 Intermediate Similarity NPC204582
0.8333 Intermediate Similarity NPC477153
0.8333 Intermediate Similarity NPC83272
0.8333 Intermediate Similarity NPC471110
0.8322 Intermediate Similarity NPC469615
0.8311 Intermediate Similarity NPC199773
0.8295 Intermediate Similarity NPC309434
0.8286 Intermediate Similarity NPC67349
0.8286 Intermediate Similarity NPC279676
0.8286 Intermediate Similarity NPC71256
0.8281 Intermediate Similarity NPC312800
0.8276 Intermediate Similarity NPC229264
0.8273 Intermediate Similarity NPC142027
0.8273 Intermediate Similarity NPC27407
0.8271 Intermediate Similarity NPC117794
0.8271 Intermediate Similarity NPC288945
0.8271 Intermediate Similarity NPC469568
0.8264 Intermediate Similarity NPC103910
0.8264 Intermediate Similarity NPC469683
0.8258 Intermediate Similarity NPC327070
0.8258 Intermediate Similarity NPC46634
0.8258 Intermediate Similarity NPC325301
0.8252 Intermediate Similarity NPC314271
0.8248 Intermediate Similarity NPC318799
0.8248 Intermediate Similarity NPC470831
0.8248 Intermediate Similarity NPC214702
0.8244 Intermediate Similarity NPC165197
0.8235 Intermediate Similarity NPC94810
0.8231 Intermediate Similarity NPC184579
0.8231 Intermediate Similarity NPC233165
0.8227 Intermediate Similarity NPC478200
0.8227 Intermediate Similarity NPC33144
0.8222 Intermediate Similarity NPC214620
0.8222 Intermediate Similarity NPC181715
0.8219 Intermediate Similarity NPC476463
0.8217 Intermediate Similarity NPC269414
0.8217 Intermediate Similarity NPC125252
0.8209 Intermediate Similarity NPC280767
0.8209 Intermediate Similarity NPC472592
0.82 Intermediate Similarity NPC82592
0.82 Intermediate Similarity NPC16082
0.82 Intermediate Similarity NPC79998
0.8195 Intermediate Similarity NPC477152
0.8194 Intermediate Similarity NPC471417
0.8188 Intermediate Similarity NPC111888
0.8188 Intermediate Similarity NPC50763
0.8188 Intermediate Similarity NPC295646
0.8182 Intermediate Similarity NPC478201
0.8182 Intermediate Similarity NPC25168
0.8182 Intermediate Similarity NPC471444
0.8182 Intermediate Similarity NPC257003
0.8182 Intermediate Similarity NPC472035
0.8176 Intermediate Similarity NPC96501
0.8176 Intermediate Similarity NPC56204
0.8176 Intermediate Similarity NPC164527
0.8176 Intermediate Similarity NPC213382
0.8176 Intermediate Similarity NPC225129
0.8169 Intermediate Similarity NPC471602
0.8169 Intermediate Similarity NPC111422
0.8169 Intermediate Similarity NPC29771
0.8169 Intermediate Similarity NPC306835
0.8169 Intermediate Similarity NPC476477
0.8169 Intermediate Similarity NPC105525
0.8169 Intermediate Similarity NPC179505
0.8169 Intermediate Similarity NPC12218
0.8169 Intermediate Similarity NPC216312
0.8169 Intermediate Similarity NPC295339
0.8169 Intermediate Similarity NPC75763
0.8169 Intermediate Similarity NPC256463
0.8169 Intermediate Similarity NPC156709
0.8169 Intermediate Similarity NPC225036
0.8169 Intermediate Similarity NPC299405
0.8163 Intermediate Similarity NPC107636
0.8156 Intermediate Similarity NPC70380
0.8151 Intermediate Similarity NPC308799
0.8148 Intermediate Similarity NPC147192
0.8148 Intermediate Similarity NPC475695
0.8146 Intermediate Similarity NPC472453
0.8146 Intermediate Similarity NPC150227
0.8143 Intermediate Similarity NPC72918
0.814 Intermediate Similarity NPC281277
0.8138 Intermediate Similarity NPC53884
0.8138 Intermediate Similarity NPC210425
0.8138 Intermediate Similarity NPC86373
0.8138 Intermediate Similarity NPC280404
0.8138 Intermediate Similarity NPC258671
0.8138 Intermediate Similarity NPC126882
0.8138 Intermediate Similarity NPC210966
0.8138 Intermediate Similarity NPC478203
0.8138 Intermediate Similarity NPC142165
0.8138 Intermediate Similarity NPC277426
0.8138 Intermediate Similarity NPC257025
0.8134 Intermediate Similarity NPC60517
0.8134 Intermediate Similarity NPC470162
0.8134 Intermediate Similarity NPC146886
0.8134 Intermediate Similarity NPC4012
0.8134 Intermediate Similarity NPC20443
0.8134 Intermediate Similarity NPC470163
0.8133 Intermediate Similarity NPC281477
0.8133 Intermediate Similarity NPC298802
0.8129 Intermediate Similarity NPC159418
0.8129 Intermediate Similarity NPC153783
0.8129 Intermediate Similarity NPC283823
0.8125 Intermediate Similarity NPC299154
0.8125 Intermediate Similarity NPC284556
0.8125 Intermediate Similarity NPC301178
0.8125 Intermediate Similarity NPC261453
0.8125 Intermediate Similarity NPC33749
0.8125 Intermediate Similarity NPC328593
0.8121 Intermediate Similarity NPC227485
0.812 Intermediate Similarity NPC244351
0.812 Intermediate Similarity NPC217756
0.812 Intermediate Similarity NPC311219
0.812 Intermediate Similarity NPC297193
0.8112 Intermediate Similarity NPC327916
0.8112 Intermediate Similarity NPC241349
0.8112 Intermediate Similarity NPC220496
0.8112 Intermediate Similarity NPC50823
0.8112 Intermediate Similarity NPC147542
0.8112 Intermediate Similarity NPC32749
0.8112 Intermediate Similarity NPC42262
0.8112 Intermediate Similarity NPC37992
0.8108 Intermediate Similarity NPC92722
0.8108 Intermediate Similarity NPC285527
0.8108 Intermediate Similarity NPC106334
0.8108 Intermediate Similarity NPC102003
0.8106 Intermediate Similarity NPC470848
0.8106 Intermediate Similarity NPC470849

  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 NPC295406 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
0.8667 High Similarity NPD447 Suspended
0.8571 High Similarity NPD9493 Approved
0.8529 High Similarity NPD230 Phase 1
0.8286 Intermediate Similarity NPD2935 Discontinued
0.812 Intermediate Similarity NPD9717 Approved
0.8029 Intermediate Similarity NPD6832 Phase 2
0.7941 Intermediate Similarity NPD1203 Approved
0.7937 Intermediate Similarity NPD9266 Approved
0.7937 Intermediate Similarity NPD74 Approved
0.7929 Intermediate Similarity NPD943 Approved
0.7914 Intermediate Similarity NPD411 Approved
0.7908 Intermediate Similarity NPD3882 Suspended
0.7895 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD2801 Approved
0.7872 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD9267 Approved
0.7857 Intermediate Similarity NPD9264 Approved
0.7857 Intermediate Similarity NPD9263 Approved
0.7852 Intermediate Similarity NPD9269 Phase 2
0.7832 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD1934 Approved
0.7826 Intermediate Similarity NPD9494 Approved
0.7808 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7792 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD1511 Approved
0.7754 Intermediate Similarity NPD1019 Discontinued
0.7746 Intermediate Similarity NPD1933 Approved
0.7744 Intermediate Similarity NPD9545 Approved
0.7727 Intermediate Similarity NPD3817 Phase 2
0.7687 Intermediate Similarity NPD8166 Discontinued
0.7671 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD1512 Approved
0.766 Intermediate Similarity NPD2313 Discontinued
0.7655 Intermediate Similarity NPD1551 Phase 2
0.7635 Intermediate Similarity NPD6190 Approved
0.7632 Intermediate Similarity NPD3455 Phase 2
0.7613 Intermediate Similarity NPD5402 Approved
0.7603 Intermediate Similarity NPD2346 Discontinued
0.76 Intermediate Similarity NPD2532 Approved
0.76 Intermediate Similarity NPD2534 Approved
0.76 Intermediate Similarity NPD2533 Approved
0.7594 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD2799 Discontinued
0.7578 Intermediate Similarity NPD3818 Discontinued
0.7576 Intermediate Similarity NPD9281 Approved
0.7556 Intermediate Similarity NPD9268 Approved
0.7547 Intermediate Similarity NPD6232 Discontinued
0.754 Intermediate Similarity NPD9261 Approved
0.7533 Intermediate Similarity NPD6799 Approved
0.7531 Intermediate Similarity NPD7054 Approved
0.7516 Intermediate Similarity NPD7075 Discontinued
0.7516 Intermediate Similarity NPD7473 Discontinued
0.7485 Intermediate Similarity NPD7074 Phase 3
0.7485 Intermediate Similarity NPD7472 Approved
0.7483 Intermediate Similarity NPD520 Approved
0.7483 Intermediate Similarity NPD7266 Discontinued
0.7455 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD6166 Phase 2
0.7453 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7445 Intermediate Similarity NPD3496 Discontinued
0.7436 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7819 Suspended
0.7429 Intermediate Similarity NPD1164 Approved
0.741 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD7251 Discontinued
0.7386 Intermediate Similarity NPD5403 Approved
0.7385 Intermediate Similarity NPD2182 Approved
0.7376 Intermediate Similarity NPD2798 Approved
0.7368 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD4380 Phase 2
0.7347 Intermediate Similarity NPD4308 Phase 3
0.7347 Intermediate Similarity NPD1510 Phase 2
0.7342 Intermediate Similarity NPD7768 Phase 2
0.7333 Intermediate Similarity NPD6797 Phase 2
0.731 Intermediate Similarity NPD825 Approved
0.731 Intermediate Similarity NPD826 Approved
0.731 Intermediate Similarity NPD1240 Approved
0.7305 Intermediate Similarity NPD1470 Approved
0.7305 Intermediate Similarity NPD2797 Approved
0.7297 Intermediate Similarity NPD5408 Approved
0.7297 Intermediate Similarity NPD5404 Approved
0.7297 Intermediate Similarity NPD5406 Approved
0.7297 Intermediate Similarity NPD5405 Approved
0.7294 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD3764 Approved
0.729 Intermediate Similarity NPD3226 Approved
0.7278 Intermediate Similarity NPD8150 Discontinued
0.7255 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD5401 Approved
0.7246 Intermediate Similarity NPD7808 Phase 3
0.7244 Intermediate Similarity NPD6599 Discontinued
0.7229 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD4628 Phase 3
0.7215 Intermediate Similarity NPD1465 Phase 2
0.7211 Intermediate Similarity NPD1607 Approved
0.7211 Intermediate Similarity NPD6653 Approved
0.72 Intermediate Similarity NPD1549 Phase 2
0.7197 Intermediate Similarity NPD7411 Suspended
0.7188 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD3268 Approved
0.7172 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6844 Discontinued
0.7152 Intermediate Similarity NPD6801 Discontinued
0.7152 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD555 Phase 2
0.7143 Intermediate Similarity NPD6355 Discontinued
0.7143 Intermediate Similarity NPD1201 Approved
0.7143 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD5647 Approved
0.7133 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD2344 Approved
0.7133 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD1778 Approved
0.7108 Intermediate Similarity NPD5844 Phase 1
0.7105 Intermediate Similarity NPD3750 Approved
0.7101 Intermediate Similarity NPD8312 Approved
0.7101 Intermediate Similarity NPD8313 Approved
0.7099 Intermediate Similarity NPD5494 Approved
0.709 Intermediate Similarity NPD228 Approved
0.7089 Intermediate Similarity NPD6386 Approved
0.7089 Intermediate Similarity NPD6385 Approved
0.7083 Intermediate Similarity NPD7685 Pre-registration
0.7083 Intermediate Similarity NPD6559 Discontinued
0.7078 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD164 Approved
0.7075 Intermediate Similarity NPD4307 Phase 2
0.7067 Intermediate Similarity NPD2796 Approved
0.7067 Intermediate Similarity NPD9570 Approved
0.7055 Intermediate Similarity NPD6798 Discontinued
0.7045 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD919 Approved
0.7037 Intermediate Similarity NPD6234 Discontinued
0.7014 Intermediate Similarity NPD258 Approved
0.7014 Intermediate Similarity NPD257 Approved
0.7011 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD6233 Phase 2
0.7007 Intermediate Similarity NPD259 Phase 1
0.7006 Intermediate Similarity NPD1653 Approved
0.7 Intermediate Similarity NPD4626 Approved
0.7 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.6986 Remote Similarity NPD3027 Phase 3
0.6981 Remote Similarity NPD2672 Discontinued
0.6962 Remote Similarity NPD7458 Discontinued
0.6959 Remote Similarity NPD4060 Phase 1
0.6957 Remote Similarity NPD5353 Approved
0.6957 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6948 Remote Similarity NPD2309 Approved
0.6943 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6943 Remote Similarity NPD920 Approved
0.694 Remote Similarity NPD3021 Approved
0.694 Remote Similarity NPD3022 Approved
0.6934 Remote Similarity NPD690 Clinical (unspecified phase)
0.6929 Remote Similarity NPD5691 Approved
0.6928 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6919 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6918 Remote Similarity NPD3684 Discontinued
0.6917 Remote Similarity NPD1358 Approved
0.6909 Remote Similarity NPD5710 Approved
0.6909 Remote Similarity NPD5711 Approved
0.6906 Remote Similarity NPD5536 Phase 2
0.6905 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6905 Remote Similarity NPD7286 Phase 2
0.6903 Remote Similarity NPD7440 Discontinued
0.6903 Remote Similarity NPD3300 Phase 2
0.6899 Remote Similarity NPD1238 Approved
0.6887 Remote Similarity NPD7033 Discontinued
0.6884 Remote Similarity NPD6671 Approved
0.6883 Remote Similarity NPD4110 Phase 3
0.6883 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6883 Remote Similarity NPD7003 Approved
0.6875 Remote Similarity NPD3225 Approved
0.6871 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6871 Remote Similarity NPD3749 Approved
0.6866 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6861 Remote Similarity NPD1241 Discontinued
0.6857 Remote Similarity NPD1759 Phase 1
0.6853 Remote Similarity NPD1481 Phase 2
0.6853 Remote Similarity NPD1608 Approved
0.6849 Remote Similarity NPD9569 Approved
0.6848 Remote Similarity NPD1247 Approved
0.6846 Remote Similarity NPD1613 Approved
0.6846 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6845 Remote Similarity NPD7228 Approved
0.6842 Remote Similarity NPD6032 Approved
0.6842 Remote Similarity NPD3134 Approved
0.6832 Remote Similarity NPD37 Approved
0.6828 Remote Similarity NPD3267 Approved
0.6828 Remote Similarity NPD3266 Approved
0.6824 Remote Similarity NPD5953 Discontinued
0.6818 Remote Similarity NPD2800 Approved
0.6815 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6815 Remote Similarity NPD4661 Approved
0.6815 Remote Similarity NPD642 Clinical (unspecified phase)
0.6815 Remote Similarity NPD4662 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