Structure

Physi-Chem Properties

Molecular Weight:  316.12
Volume:  296.0
LogP:  -1.062
LogD:  -0.63
LogS:  -0.462
# Rotatable Bonds:  5
TPSA:  139.84
# H-Bond Aceptor:  8
# H-Bond Donor:  6
# Rings:  2
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.359
Synthetic Accessibility Score:  3.567
Fsp3:  0.571
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.831
MDCK Permeability:  2.6619505661074072e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.052
Human Intestinal Absorption (HIA):  0.971
20% Bioavailability (F20%):  0.987
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.254
Plasma Protein Binding (PPB):  46.41109848022461%
Volume Distribution (VD):  1.138
Pgp-substrate:  51.08352279663086%

ADMET: Metabolism

CYP1A2-inhibitor:  0.055
CYP1A2-substrate:  0.053
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.071
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.289
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.184
CYP3A4-inhibitor:  0.011
CYP3A4-substrate:  0.038

ADMET: Excretion

Clearance (CL):  5.751
Half-life (T1/2):  0.898

ADMET: Toxicity

hERG Blockers:  0.089
Human Hepatotoxicity (H-HT):  0.054
Drug-inuced Liver Injury (DILI):  0.033
AMES Toxicity:  0.449
Rat Oral Acute Toxicity:  0.046
Maximum Recommended Daily Dose:  0.003
Skin Sensitization:  0.92
Carcinogencity:  0.155
Eye Corrosion:  0.004
Eye Irritation:  0.523
Respiratory Toxicity:  0.023

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

  Natural Product: NPC266045

Natural Product ID:  NPC266045
Common Name*:   3,4-Dihydroxyphenylethyl Beta-D-Glucopyranoside
IUPAC Name:   (2R,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  PQQITYGQJLPDFC-RKQHYHRCSA-N
Standard InCHI:  InChI=1S/C14H20O8/c15-6-10-11(18)12(19)13(20)14(22-10)21-4-3-7-1-2-8(16)9(17)5-7/h1-2,5,10-20H,3-4,6H2/t10-,11-,12+,13-,14-/m1/s1
SMILES:  OC[C@H]1O[C@@H](OCCc2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1689261
PubChem CID:   5316821
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO12173 Zantedeschia aethiopica Species Araceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(98)00092-2]
NPO6987 Tolypothrix byssoidea Species Tolypothrichaceae Bacteria n.a. n.a. n.a. PMID[11429991]
NPO30241 Picrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. root n.a. PMID[15133218]
NPO30241 Picrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. root n.a. PMID[15706916]
NPO23838 Kitasatospora kifunensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17191679]
NPO19548 Lepisorus contortus Species Polypodiaceae Eukaryota n.a. whole plant n.a. PMID[21261296]
NPO19548 Lepisorus contortus Species Polypodiaceae Eukaryota whole plant Gongshan County, Yunnan, China n.a. PMID[21261296]
NPO16259 Syringa reticulata Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[21955940]
NPO30241 Picrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[24035096]
NPO12173 Zantedeschia aethiopica Species Araceae Eukaryota n.a. n.a. n.a. PMID[25924520]
NPO30241 Picrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5788 Millingtonia hortensis Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO228 Physostigma venenosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO201 Gmelina arborea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO228 Physostigma venenosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19361 Herba meconpsis integrifoliae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO4853 Carduus crispus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5788 Millingtonia hortensis Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14460 Berberis aquifolium Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO201 Gmelina arborea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4853 Carduus crispus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5788 Millingtonia hortensis Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30241 Picrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO228 Physostigma venenosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO201 Gmelina arborea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8719 Fusarium vasinfectum Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23838 Kitasatospora kifunensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11437 Alluaudia ascendens Species Didiereaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10826 Rabdosia weisiensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11012 Knema attenuata Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO228 Physostigma venenosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8024 Diplopteraster multipes Species Pterasteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4669 Hydnocarpus octandra Species Achariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4214 Centaurea collina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11822 Antitrogus consanguineus Species Scarabaeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19548 Lepisorus contortus Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8231 Jaspis digonoxea Species Ancorinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14460 Berberis aquifolium Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO201 Gmelina arborea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20649 Rhizopogon pumilionus Species Rhizopogonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6710 Sinapis nigra Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5788 Millingtonia hortensis Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5445 Euonymus nanus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10196 Echinocereus blanckii Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4489 Achillea serbica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2994 Hornschuchia citriodora Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12173 Zantedeschia aethiopica Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16259 Syringa reticulata Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10544 Centaurea napifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11189 Anabaena sphaerica Species 0stocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6987 Tolypothrix byssoidea Species Tolypothrichaceae Bacteria 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 4970.0 nM PMID[505178]
NPT1 Others Radical scavenging activity EC50 = 32960.0 nM PMID[505178]

☑ 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 NPC266045 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
0.9661 High Similarity NPC90318
0.95 High Similarity NPC108659
0.95 High Similarity NPC231607
0.95 High Similarity NPC79715
0.95 High Similarity NPC264900
0.9421 High Similarity NPC148982
0.9417 High Similarity NPC94179
0.9344 High Similarity NPC184092
0.9298 High Similarity NPC157338
0.9194 High Similarity NPC65942
0.9194 High Similarity NPC248307
0.9138 High Similarity NPC148055
0.912 High Similarity NPC254275
0.9106 High Similarity NPC232880
0.9068 High Similarity NPC477803
0.9032 High Similarity NPC307110
0.9032 High Similarity NPC477293
0.9032 High Similarity NPC229784
0.9032 High Similarity NPC477294
0.9024 High Similarity NPC476873
0.8992 High Similarity NPC469702
0.8992 High Similarity NPC282409
0.8976 High Similarity NPC35731
0.8976 High Similarity NPC886
0.8976 High Similarity NPC470881
0.8976 High Similarity NPC287597
0.8976 High Similarity NPC34293
0.8974 High Similarity NPC175771
0.8966 High Similarity NPC313193
0.8917 High Similarity NPC201402
0.8917 High Similarity NPC476445
0.8917 High Similarity NPC469704
0.8917 High Similarity NPC476448
0.8917 High Similarity NPC469703
0.8917 High Similarity NPC469548
0.8917 High Similarity NPC160854
0.8906 High Similarity NPC123988
0.8898 High Similarity NPC6836
0.8889 High Similarity NPC219677
0.888 High Similarity NPC166040
0.8843 High Similarity NPC469686
0.8843 High Similarity NPC55608
0.8837 High Similarity NPC199459
0.8837 High Similarity NPC52277
0.8837 High Similarity NPC177035
0.8828 High Similarity NPC107478
0.8819 High Similarity NPC252833
0.8819 High Similarity NPC473924
0.8819 High Similarity NPC473285
0.8819 High Similarity NPC470270
0.881 High Similarity NPC472024
0.881 High Similarity NPC80600
0.877 High Similarity NPC471067
0.8769 High Similarity NPC310252
0.8769 High Similarity NPC304152
0.8769 High Similarity NPC84789
0.8769 High Similarity NPC302583
0.8769 High Similarity NPC78363
0.8769 High Similarity NPC100558
0.8769 High Similarity NPC260425
0.8769 High Similarity NPC470413
0.8769 High Similarity NPC138738
0.876 High Similarity NPC180171
0.876 High Similarity NPC103398
0.876 High Similarity NPC158325
0.875 High Similarity NPC254398
0.875 High Similarity NPC132895
0.874 High Similarity NPC166168
0.874 High Similarity NPC9912
0.873 High Similarity NPC26653
0.873 High Similarity NPC248355
0.873 High Similarity NPC270849
0.8702 High Similarity NPC476383
0.8702 High Similarity NPC472350
0.8702 High Similarity NPC68092
0.8702 High Similarity NPC89105
0.8702 High Similarity NPC321638
0.8702 High Similarity NPC328273
0.8702 High Similarity NPC321184
0.8702 High Similarity NPC81515
0.8702 High Similarity NPC197316
0.8702 High Similarity NPC64141
0.8702 High Similarity NPC171134
0.8702 High Similarity NPC205195
0.8699 High Similarity NPC232454
0.8699 High Similarity NPC178449
0.8699 High Similarity NPC470907
0.8682 High Similarity NPC471883
0.8651 High Similarity NPC302378
0.8636 High Similarity NPC106944
0.8626 High Similarity NPC476376
0.8615 High Similarity NPC476870
0.8605 High Similarity NPC25821
0.8571 High Similarity NPC476385
0.8571 High Similarity NPC134405
0.8571 High Similarity NPC476377
0.8571 High Similarity NPC472711
0.8571 High Similarity NPC47471
0.8571 High Similarity NPC469661
0.855 High Similarity NPC470572
0.855 High Similarity NPC203230
0.855 High Similarity NPC157554
0.855 High Similarity NPC186418
0.855 High Similarity NPC242028
0.8548 High Similarity NPC212176
0.8538 High Similarity NPC476411
0.8538 High Similarity NPC87696
0.8538 High Similarity NPC187194
0.8538 High Similarity NPC48863
0.8538 High Similarity NPC13745
0.8538 High Similarity NPC251981
0.8537 High Similarity NPC11724
0.8537 High Similarity NPC470804
0.8527 High Similarity NPC299144
0.8507 High Similarity NPC469559
0.8507 High Similarity NPC265648
0.8507 High Similarity NPC48309
0.8507 High Similarity NPC140502
0.8507 High Similarity NPC296643
0.8507 High Similarity NPC189115
0.8507 High Similarity NPC222433
0.8496 Intermediate Similarity NPC473799
0.8496 Intermediate Similarity NPC475530
0.8485 Intermediate Similarity NPC59324
0.8485 Intermediate Similarity NPC195196
0.8485 Intermediate Similarity NPC65530
0.8473 Intermediate Similarity NPC101624
0.8473 Intermediate Similarity NPC184938
0.8468 Intermediate Similarity NPC52097
0.8462 Intermediate Similarity NPC49074
0.8462 Intermediate Similarity NPC69513
0.8462 Intermediate Similarity NPC215833
0.8455 Intermediate Similarity NPC269242
0.8455 Intermediate Similarity NPC476872
0.845 Intermediate Similarity NPC476407
0.8444 Intermediate Similarity NPC264632
0.8444 Intermediate Similarity NPC247032
0.8444 Intermediate Similarity NPC476381
0.8444 Intermediate Similarity NPC76406
0.8444 Intermediate Similarity NPC185307
0.8444 Intermediate Similarity NPC470950
0.8444 Intermediate Similarity NPC269141
0.8444 Intermediate Similarity NPC476375
0.8444 Intermediate Similarity NPC96795
0.8444 Intermediate Similarity NPC278961
0.8444 Intermediate Similarity NPC298257
0.8444 Intermediate Similarity NPC40305
0.8444 Intermediate Similarity NPC476397
0.8444 Intermediate Similarity NPC477898
0.8444 Intermediate Similarity NPC473044
0.8444 Intermediate Similarity NPC205864
0.8444 Intermediate Similarity NPC175214
0.8444 Intermediate Similarity NPC476378
0.8444 Intermediate Similarity NPC113680
0.8444 Intermediate Similarity NPC105005
0.8444 Intermediate Similarity NPC119537
0.8444 Intermediate Similarity NPC46092
0.8444 Intermediate Similarity NPC476380
0.8444 Intermediate Similarity NPC112
0.8444 Intermediate Similarity NPC476384
0.8433 Intermediate Similarity NPC186406
0.8425 Intermediate Similarity NPC469687
0.8425 Intermediate Similarity NPC288416
0.8421 Intermediate Similarity NPC12278
0.8421 Intermediate Similarity NPC212770
0.8421 Intermediate Similarity NPC98777
0.8421 Intermediate Similarity NPC220942
0.8421 Intermediate Similarity NPC226005
0.8421 Intermediate Similarity NPC100389
0.8413 Intermediate Similarity NPC126991
0.8413 Intermediate Similarity NPC83218
0.8403 Intermediate Similarity NPC264558
0.84 Intermediate Similarity NPC473451
0.839 Intermediate Similarity NPC179002
0.839 Intermediate Similarity NPC187583
0.839 Intermediate Similarity NPC257430
0.8385 Intermediate Similarity NPC162093
0.8382 Intermediate Similarity NPC84181
0.8382 Intermediate Similarity NPC25292
0.8382 Intermediate Similarity NPC283995
0.8382 Intermediate Similarity NPC469313
0.8382 Intermediate Similarity NPC168579
0.8382 Intermediate Similarity NPC138227
0.8382 Intermediate Similarity NPC76176
0.8382 Intermediate Similarity NPC470235
0.8382 Intermediate Similarity NPC300894
0.8382 Intermediate Similarity NPC473045
0.8382 Intermediate Similarity NPC141455
0.8382 Intermediate Similarity NPC129417
0.8382 Intermediate Similarity NPC296954
0.8382 Intermediate Similarity NPC196063
0.8382 Intermediate Similarity NPC64195
0.8374 Intermediate Similarity NPC469708
0.8374 Intermediate Similarity NPC148615
0.8374 Intermediate Similarity NPC35071
0.8374 Intermediate Similarity NPC177475
0.8374 Intermediate Similarity NPC60589
0.837 Intermediate Similarity NPC472714
0.837 Intermediate Similarity NPC475084
0.837 Intermediate Similarity NPC476356

  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 NPC266045 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
0.8702 High Similarity NPD7266 Discontinued
0.8095 Intermediate Similarity NPD1091 Approved
0.8015 Intermediate Similarity NPD3027 Phase 3
0.797 Intermediate Similarity NPD1613 Approved
0.797 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7958 Intermediate Similarity NPD1653 Approved
0.7769 Intermediate Similarity NPD3021 Approved
0.7769 Intermediate Similarity NPD3022 Approved
0.7717 Intermediate Similarity NPD1357 Approved
0.7674 Intermediate Similarity NPD3705 Approved
0.7669 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7656 Intermediate Similarity NPD9384 Approved
0.7656 Intermediate Similarity NPD9381 Approved
0.7642 Intermediate Similarity NPD228 Approved
0.7594 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7535 Intermediate Similarity NPD6190 Approved
0.7424 Intermediate Similarity NPD9622 Approved
0.7419 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD6674 Discontinued
0.7319 Intermediate Similarity NPD3061 Approved
0.7319 Intermediate Similarity NPD3062 Approved
0.7319 Intermediate Similarity NPD3059 Approved
0.7259 Intermediate Similarity NPD9621 Approved
0.7259 Intermediate Similarity NPD9620 Approved
0.7259 Intermediate Similarity NPD9619 Approved
0.7254 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD1242 Phase 1
0.7215 Intermediate Similarity NPD7054 Approved
0.7214 Intermediate Similarity NPD823 Approved
0.7214 Intermediate Similarity NPD5314 Approved
0.7214 Intermediate Similarity NPD817 Approved
0.7185 Intermediate Similarity NPD3094 Phase 2
0.7174 Intermediate Similarity NPD597 Approved
0.7174 Intermediate Similarity NPD598 Approved
0.7174 Intermediate Similarity NPD601 Approved
0.717 Intermediate Similarity NPD7472 Approved
0.717 Intermediate Similarity NPD7074 Phase 3
0.7165 Intermediate Similarity NPD9377 Approved
0.7165 Intermediate Similarity NPD9379 Approved
0.7152 Intermediate Similarity NPD7228 Approved
0.7152 Intermediate Similarity NPD3818 Discontinued
0.7143 Intermediate Similarity NPD6234 Discontinued
0.7143 Intermediate Similarity NPD230 Phase 1
0.7125 Intermediate Similarity NPD6797 Phase 2
0.7122 Intermediate Similarity NPD1136 Approved
0.7122 Intermediate Similarity NPD1132 Approved
0.7122 Intermediate Similarity NPD1130 Approved
0.7121 Intermediate Similarity NPD5125 Phase 3
0.7121 Intermediate Similarity NPD5126 Approved
0.7119 Intermediate Similarity NPD2933 Approved
0.7119 Intermediate Similarity NPD2934 Approved
0.7105 Intermediate Similarity NPD2977 Approved
0.7105 Intermediate Similarity NPD2978 Approved
0.7081 Intermediate Similarity NPD7251 Discontinued
0.708 Intermediate Similarity NPD2861 Phase 2
0.7063 Intermediate Similarity NPD9570 Approved
0.7059 Intermediate Similarity NPD2859 Approved
0.7059 Intermediate Similarity NPD2860 Approved
0.7049 Intermediate Similarity NPD940 Approved
0.7049 Intermediate Similarity NPD846 Approved
0.7039 Intermediate Similarity NPD37 Approved
0.7037 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD7843 Approved
0.7025 Intermediate Similarity NPD3020 Approved
0.7015 Intermediate Similarity NPD3092 Approved
0.7013 Intermediate Similarity NPD4967 Phase 2
0.7013 Intermediate Similarity NPD4966 Approved
0.7013 Intermediate Similarity NPD4965 Approved
0.7007 Intermediate Similarity NPD5058 Phase 3
0.7 Intermediate Similarity NPD7157 Approved
0.6984 Remote Similarity NPD2684 Approved
0.6977 Remote Similarity NPD5283 Phase 1
0.6975 Remote Similarity NPD7685 Pre-registration
0.6975 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6968 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6959 Remote Similarity NPD6143 Clinical (unspecified phase)
0.695 Remote Similarity NPD3620 Phase 2
0.695 Remote Similarity NPD826 Approved
0.695 Remote Similarity NPD3619 Clinical (unspecified phase)
0.695 Remote Similarity NPD1558 Phase 1
0.695 Remote Similarity NPD825 Approved
0.6933 Remote Similarity NPD7808 Phase 3
0.6929 Remote Similarity NPD9380 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6917 Remote Similarity NPD844 Approved
0.6913 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6912 Remote Similarity NPD2983 Phase 2
0.6912 Remote Similarity NPD2982 Phase 2
0.6905 Remote Similarity NPD290 Approved
0.6903 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6897 Remote Similarity NPD1375 Discontinued
0.6889 Remote Similarity NPD1610 Phase 2
0.6883 Remote Similarity NPD8455 Phase 2
0.6842 Remote Similarity NPD3091 Approved
0.6842 Remote Similarity NPD1548 Phase 1
0.6838 Remote Similarity NPD2981 Phase 2
0.6838 Remote Similarity NPD9269 Phase 2
0.6835 Remote Similarity NPD3018 Phase 2
0.6829 Remote Similarity NPD289 Clinical (unspecified phase)
0.6822 Remote Similarity NPD969 Suspended
0.6818 Remote Similarity NPD1934 Approved
0.6806 Remote Similarity NPD4536 Approved
0.6806 Remote Similarity NPD4538 Approved
0.6806 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6803 Remote Similarity NPD4237 Approved
0.6803 Remote Similarity NPD3060 Approved
0.6803 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6803 Remote Similarity NPD4236 Phase 3
0.6797 Remote Similarity NPD4750 Phase 3
0.6786 Remote Similarity NPD4908 Phase 1
0.6783 Remote Similarity NPD555 Phase 2
0.6783 Remote Similarity NPD111 Approved
0.6774 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6759 Remote Similarity NPD5960 Phase 3
0.6759 Remote Similarity NPD5588 Approved
0.6742 Remote Similarity NPD6671 Approved
0.6741 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6739 Remote Similarity NPD5311 Approved
0.6739 Remote Similarity NPD5310 Approved
0.673 Remote Similarity NPD7199 Phase 2
0.6721 Remote Similarity NPD288 Approved
0.6713 Remote Similarity NPD943 Approved
0.6713 Remote Similarity NPD4060 Phase 1
0.6708 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6708 Remote Similarity NPD6166 Phase 2
0.6708 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6693 Remote Similarity NPD968 Approved
0.6691 Remote Similarity NPD3053 Approved
0.6691 Remote Similarity NPD3055 Approved
0.669 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6689 Remote Similarity NPD1652 Phase 2
0.6667 Remote Similarity NPD3687 Approved
0.6667 Remote Similarity NPD7240 Approved
0.6667 Remote Similarity NPD9614 Approved
0.6667 Remote Similarity NPD9618 Approved
0.6667 Remote Similarity NPD6559 Discontinued
0.6667 Remote Similarity NPD3686 Approved
0.6646 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6644 Remote Similarity NPD8166 Discontinued
0.6644 Remote Similarity NPD4108 Discontinued
0.6643 Remote Similarity NPD258 Approved
0.6643 Remote Similarity NPD257 Approved
0.6643 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6643 Remote Similarity NPD259 Phase 1
0.6643 Remote Similarity NPD2674 Phase 3
0.6643 Remote Similarity NPD6405 Approved
0.6643 Remote Similarity NPD6407 Approved
0.6642 Remote Similarity NPD16 Approved
0.6642 Remote Similarity NPD856 Approved
0.664 Remote Similarity NPD291 Approved
0.6623 Remote Similarity NPD1774 Approved
0.6623 Remote Similarity NPD1511 Approved
0.6621 Remote Similarity NPD2568 Approved
0.6621 Remote Similarity NPD6653 Approved
0.6619 Remote Similarity NPD9634 Clinical (unspecified phase)
0.6619 Remote Similarity NPD8651 Approved
0.6618 Remote Similarity NPD3095 Discontinued
0.661 Remote Similarity NPD9094 Approved
0.6607 Remote Similarity NPD8055 Clinical (unspecified phase)
0.66 Remote Similarity NPD2677 Approved
0.6596 Remote Similarity NPD5736 Approved
0.6596 Remote Similarity NPD9569 Approved
0.6596 Remote Similarity NPD9494 Approved
0.6594 Remote Similarity NPD2235 Phase 2
0.6594 Remote Similarity NPD2231 Phase 2
0.6593 Remote Similarity NPD9545 Approved
0.6585 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6581 Remote Similarity NPD4380 Phase 2
0.6575 Remote Similarity NPD7097 Phase 1
0.6573 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6561 Remote Similarity NPD2801 Approved
0.6561 Remote Similarity NPD5773 Approved
0.6561 Remote Similarity NPD5772 Approved
0.656 Remote Similarity NPD3028 Approved
0.6547 Remote Similarity NPD4749 Approved
0.6547 Remote Similarity NPD4659 Approved
0.6547 Remote Similarity NPD3685 Discontinued
0.6544 Remote Similarity NPD9268 Approved
0.6543 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6538 Remote Similarity NPD556 Approved
0.6536 Remote Similarity NPD1512 Approved
0.6533 Remote Similarity NPD4628 Phase 3
0.6531 Remote Similarity NPD651 Clinical (unspecified phase)
0.6528 Remote Similarity NPD6233 Phase 2
0.6522 Remote Similarity NPD422 Phase 1
0.6522 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6522 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6519 Remote Similarity NPD5536 Phase 2
0.6519 Remote Similarity NPD9616 Approved
0.6519 Remote Similarity NPD317 Approved
0.6519 Remote Similarity NPD9613 Approved
0.6519 Remote Similarity NPD9615 Approved
0.6519 Remote Similarity NPD318 Approved
0.6516 Remote Similarity NPD3455 Phase 2
0.6512 Remote Similarity NPD1358 Approved
0.6506 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6504 Remote Similarity NPD1809 Phase 2
0.6496 Remote Similarity NPD6516 Phase 2
0.6496 Remote Similarity NPD5846 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