Structure

Physi-Chem Properties

Molecular Weight:  316.12
Volume:  296.0
LogP:  -0.812
LogD:  -0.859
LogS:  -0.83
# Rotatable Bonds:  5
TPSA:  128.84
# H-Bond Aceptor:  8
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.438
Synthetic Accessibility Score:  3.405
Fsp3:  0.571
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.621
MDCK Permeability:  7.492152508348227e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.065
Human Intestinal Absorption (HIA):  0.695
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.682

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.338
Plasma Protein Binding (PPB):  22.993803024291992%
Volume Distribution (VD):  0.395
Pgp-substrate:  55.82593536376953%

ADMET: Metabolism

CYP1A2-inhibitor:  0.059
CYP1A2-substrate:  0.085
CYP2C19-inhibitor:  0.014
CYP2C19-substrate:  0.749
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.247
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.373
CYP3A4-inhibitor:  0.004
CYP3A4-substrate:  0.05

ADMET: Excretion

Clearance (CL):  1.911
Half-life (T1/2):  0.872

ADMET: Toxicity

hERG Blockers:  0.156
Human Hepatotoxicity (H-HT):  0.05
Drug-inuced Liver Injury (DILI):  0.11
AMES Toxicity:  0.161
Rat Oral Acute Toxicity:  0.006
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.147
Carcinogencity:  0.056
Eye Corrosion:  0.003
Eye Irritation:  0.113
Respiratory Toxicity:  0.014

Download Data

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC166040

Natural Product ID:  NPC166040
Common Name*:   Vanilloloside
IUPAC Name:   (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxane-3,4,5-triol
Synonyms:   Vanilloloside
Standard InCHIKey:  SIMPNXWTAVEOTO-RKQHYHRCSA-N
Standard InCHI:  InChI=1S/C14H20O8/c1-20-9-4-7(5-15)2-3-8(9)21-14-13(19)12(18)11(17)10(6-16)22-14/h2-4,10-19H,5-6H2,1H3/t10-,11-,12+,13-,14-/m1/s1
SMILES:  COc1cc(ccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL468568
PubChem CID:   44577222
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:0004165] Phenolic glycosides

*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
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[11520233]
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[12932145]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. bulb n.a. PMID[14994197]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[15844951]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota tubers n.a. n.a. PMID[16792409]
NPO9317 Itoa orientalis Species Salicaceae Eukaryota bark, twigs, and leaves n.a. n.a. PMID[18412396]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota bark n.a. n.a. PMID[22032697]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. bark n.a. PMID[22032697]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[23627123]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. kernel n.a. PMID[7092570]
NPO14992 Prunus persica Species Rosaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO16693 Byrsonima crassifolia Species Malpighiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16693 Byrsonima crassifolia Species Malpighiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO16693 Byrsonima crassifolia Species Malpighiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9141 Epimedium wushanense Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26304 Hymenocallis littoralis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15954 Pyrenula japonica Species Pyrenulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26304 Hymenocallis littoralis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9141 Epimedium wushanense Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12875 Pleione yunnanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9141 Epimedium wushanense Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26538 Phellodendron chinese Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12875 Pleione yunnanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16326 Scopolia parviflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO619 Ankistrodesmus braunii Species Selenastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15594 Aplidiopsis confluata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO24476 Phellodendron amurense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14001 Ceroplastes pseudoceriferus Species Coccidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16326 Scopolia parviflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9141 Epimedium wushanense Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17141 Lonchocarpus longistylus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5016 Glossogyne tenuifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17444 Gleichenia japonica Species Gleicheniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18071 Euryops pedunculatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26304 Hymenocallis littoralis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15954 Pyrenula japonica Species Pyrenulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17917 Thamnophis sirtalis Species Colubridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15740 Garcinia purpurea Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12630 Senecio oxyodontus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14507.1 Quercus ithaburensis subsp. macrolepis Subspecies Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9317 Itoa orientalis Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14559 Acer saccharum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16049 Cryptocarya pleurosperma Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11755 Banisteriopsis caapi Species Malpighiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17757 Plectranthus saccatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16210 Androcymbium palaestinum Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10751 Bothriocline laxa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16693 Byrsonima crassifolia Species Malpighiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17600 Gnathotrichus sulcatus Species Curculionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12875 Pleione yunnanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11280 Aphanoascus terreus Species Onygenaceae 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
NPT31 Individual Protein Cyclooxygenase-2 Homo sapiens Inhibition = 41.0 % PMID[452711]
NPT393 Cell Line HCT-116 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[452713]
NPT492 Cell Line Caco-2 Homo sapiens IC50 < 5.0 ug.mL-1 PMID[452713]
NPT27 Others Unspecified IC50 < 5.0 ug.mL-1 PMID[452713]

☑ 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 NPC166040 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
0.9837 High Similarity NPC248355
0.9758 High Similarity NPC472024
0.9758 High Similarity NPC80600
0.9756 High Similarity NPC302378
0.9683 High Similarity NPC25821
0.9677 High Similarity NPC270849
0.9677 High Similarity NPC26653
0.9603 High Similarity NPC299144
0.9528 High Similarity NPC49074
0.9524 High Similarity NPC65942
0.9524 High Similarity NPC248307
0.9524 High Similarity NPC9912
0.952 High Similarity NPC307110
0.9453 High Similarity NPC48863
0.9453 High Similarity NPC187194
0.9453 High Similarity NPC251981
0.9453 High Similarity NPC13745
0.9449 High Similarity NPC162093
0.9385 High Similarity NPC470413
0.9385 High Similarity NPC138738
0.9375 High Similarity NPC69513
0.9375 High Similarity NPC215833
0.9375 High Similarity NPC6836
0.937 High Similarity NPC166168
0.9308 High Similarity NPC37468
0.9308 High Similarity NPC164857
0.9302 High Similarity NPC476411
0.9302 High Similarity NPC35731
0.9302 High Similarity NPC470881
0.9297 High Similarity NPC470270
0.9297 High Similarity NPC252833
0.9262 High Similarity NPC269242
0.9231 High Similarity NPC55040
0.9231 High Similarity NPC470236
0.9225 High Similarity NPC132895
0.9167 High Similarity NPC212770
0.9167 High Similarity NPC100389
0.9167 High Similarity NPC98777
0.916 High Similarity NPC52277
0.916 High Similarity NPC199459
0.916 High Similarity NPC104167
0.916 High Similarity NPC177035
0.916 High Similarity NPC186418
0.9154 High Similarity NPC87696
0.9154 High Similarity NPC107478
0.9106 High Similarity NPC469412
0.9106 High Similarity NPC198734
0.9104 High Similarity NPC189115
0.9104 High Similarity NPC469559
0.9104 High Similarity NPC60249
0.9104 High Similarity NPC475084
0.9098 High Similarity NPC106944
0.9091 High Similarity NPC304152
0.9091 High Similarity NPC65530
0.9091 High Similarity NPC59324
0.9037 High Similarity NPC185307
0.9037 High Similarity NPC46092
0.9037 High Similarity NPC478239
0.9037 High Similarity NPC470950
0.903 High Similarity NPC76871
0.903 High Similarity NPC469661
0.9024 High Similarity NPC60589
0.9024 High Similarity NPC469708
0.9015 High Similarity NPC157554
0.9015 High Similarity NPC242028
0.9015 High Similarity NPC203230
0.9015 High Similarity NPC172818
0.9015 High Similarity NPC25695
0.8984 High Similarity NPC40377
0.8971 High Similarity NPC473045
0.8971 High Similarity NPC25292
0.8971 High Similarity NPC283995
0.8971 High Similarity NPC129417
0.8971 High Similarity NPC470235
0.8968 High Similarity NPC109822
0.8968 High Similarity NPC94276
0.8963 High Similarity NPC246947
0.8963 High Similarity NPC476356
0.8963 High Similarity NPC157816
0.8955 High Similarity NPC202700
0.8955 High Similarity NPC210478
0.8947 High Similarity NPC195196
0.8943 High Similarity NPC135961
0.8931 High Similarity NPC115022
0.8931 High Similarity NPC294166
0.8915 High Similarity NPC86030
0.8915 High Similarity NPC97326
0.8915 High Similarity NPC5851
0.8906 High Similarity NPC41706
0.8906 High Similarity NPC118787
0.8906 High Similarity NPC147821
0.8906 High Similarity NPC292056
0.8906 High Similarity NPC111247
0.8906 High Similarity NPC319625
0.8906 High Similarity NPC183181
0.8906 High Similarity NPC163332
0.8905 High Similarity NPC279298
0.8905 High Similarity NPC18979
0.8905 High Similarity NPC476301
0.8905 High Similarity NPC22150
0.8905 High Similarity NPC475096
0.8905 High Similarity NPC38041
0.8905 High Similarity NPC43508
0.8898 High Similarity NPC12308
0.8897 High Similarity NPC252169
0.8897 High Similarity NPC473044
0.8889 High Similarity NPC186406
0.8889 High Similarity NPC472711
0.8881 High Similarity NPC226005
0.888 High Similarity NPC470804
0.888 High Similarity NPC226712
0.888 High Similarity NPC266045
0.8855 High Similarity NPC303422
0.8855 High Similarity NPC165686
0.8855 High Similarity NPC85799
0.8855 High Similarity NPC26080
0.8841 High Similarity NPC112861
0.8841 High Similarity NPC190714
0.8841 High Similarity NPC125755
0.8841 High Similarity NPC99515
0.8841 High Similarity NPC199928
0.8837 High Similarity NPC72529
0.8832 High Similarity NPC471063
0.8832 High Similarity NPC79429
0.8832 High Similarity NPC471667
0.8832 High Similarity NPC217635
0.8832 High Similarity NPC232228
0.8828 High Similarity NPC178284
0.8828 High Similarity NPC58607
0.8828 High Similarity NPC191037
0.8824 High Similarity NPC140502
0.8824 High Similarity NPC48309
0.8819 High Similarity NPC48990
0.8819 High Similarity NPC293701
0.8819 High Similarity NPC287429
0.8819 High Similarity NPC114901
0.881 High Similarity NPC71090
0.881 High Similarity NPC476142
0.8806 High Similarity NPC477797
0.8806 High Similarity NPC477798
0.8797 High Similarity NPC184938
0.8797 High Similarity NPC101624
0.8797 High Similarity NPC238243
0.8779 High Similarity NPC469625
0.8779 High Similarity NPC121376
0.8779 High Similarity NPC30043
0.8779 High Similarity NPC469698
0.8779 High Similarity NPC469613
0.8779 High Similarity NPC473412
0.8777 High Similarity NPC213074
0.8777 High Similarity NPC15956
0.8777 High Similarity NPC227902
0.8777 High Similarity NPC39657
0.8777 High Similarity NPC275284
0.8777 High Similarity NPC224674
0.8777 High Similarity NPC31325
0.8777 High Similarity NPC114505
0.8777 High Similarity NPC193473
0.8769 High Similarity NPC226788
0.8769 High Similarity NPC210623
0.8769 High Similarity NPC470258
0.8769 High Similarity NPC285339
0.8769 High Similarity NPC218856
0.8769 High Similarity NPC202582
0.8769 High Similarity NPC222004
0.8769 High Similarity NPC190629
0.8769 High Similarity NPC3439
0.8769 High Similarity NPC273295
0.8768 High Similarity NPC277867
0.8768 High Similarity NPC469586
0.8768 High Similarity NPC161700
0.8759 High Similarity NPC113680
0.8759 High Similarity NPC278961
0.8759 High Similarity NPC477898
0.875 High Similarity NPC470510
0.875 High Similarity NPC194519
0.8741 High Similarity NPC156376
0.8731 High Similarity NPC197723
0.8731 High Similarity NPC165482
0.8731 High Similarity NPC3293
0.8731 High Similarity NPC138350
0.8731 High Similarity NPC40664
0.8722 High Similarity NPC170694
0.8722 High Similarity NPC130496
0.8722 High Similarity NPC188555
0.872 High Similarity NPC177475
0.872 High Similarity NPC35071
0.872 High Similarity NPC148615
0.8714 High Similarity NPC175976
0.8712 High Similarity NPC16208
0.8712 High Similarity NPC184447
0.8712 High Similarity NPC160991
0.8712 High Similarity NPC35932
0.8712 High Similarity NPC7903
0.8705 High Similarity NPC476865
0.8705 High Similarity NPC205796
0.8705 High Similarity NPC276753
0.8702 High Similarity NPC469612
0.8702 High Similarity NPC469614
0.8702 High Similarity NPC262606

  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 NPC166040 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
0.888 High Similarity NPD1091 Approved
0.8521 High Similarity NPD1653 Approved
0.8492 Intermediate Similarity NPD1357 Approved
0.8346 Intermediate Similarity NPD3027 Phase 3
0.8296 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8296 Intermediate Similarity NPD1613 Approved
0.8295 Intermediate Similarity NPD3705 Approved
0.8214 Intermediate Similarity NPD6674 Discontinued
0.8201 Intermediate Similarity NPD7266 Discontinued
0.8 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD228 Approved
0.7926 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7823 Intermediate Similarity NPD290 Approved
0.7795 Intermediate Similarity NPD7843 Approved
0.776 Intermediate Similarity NPD2684 Approved
0.7752 Intermediate Similarity NPD7157 Approved
0.7722 Intermediate Similarity NPD7054 Approved
0.7705 Intermediate Similarity NPD291 Approved
0.7692 Intermediate Similarity NPD1375 Discontinued
0.7673 Intermediate Similarity NPD7472 Approved
0.7673 Intermediate Similarity NPD7074 Phase 3
0.7671 Intermediate Similarity NPD5058 Phase 3
0.763 Intermediate Similarity NPD2982 Phase 2
0.763 Intermediate Similarity NPD2983 Phase 2
0.7597 Intermediate Similarity NPD5283 Phase 1
0.7566 Intermediate Similarity NPD37 Approved
0.7559 Intermediate Similarity NPD556 Approved
0.7556 Intermediate Similarity NPD2981 Phase 2
0.7547 Intermediate Similarity NPD3818 Discontinued
0.7536 Intermediate Similarity NPD3018 Phase 2
0.7536 Intermediate Similarity NPD2861 Phase 2
0.7532 Intermediate Similarity NPD4965 Approved
0.7532 Intermediate Similarity NPD4966 Approved
0.7532 Intermediate Similarity NPD4967 Phase 2
0.7531 Intermediate Similarity NPD7808 Phase 3
0.7518 Intermediate Similarity NPD1558 Phase 1
0.7516 Intermediate Similarity NPD6797 Phase 2
0.75 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD4536 Approved
0.7483 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD4538 Approved
0.7469 Intermediate Similarity NPD7251 Discontinued
0.7466 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD7199 Phase 2
0.7447 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD7228 Approved
0.7436 Intermediate Similarity NPD6234 Discontinued
0.7423 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD3687 Approved
0.7417 Intermediate Similarity NPD3686 Approved
0.7403 Intermediate Similarity NPD2977 Approved
0.7403 Intermediate Similarity NPD8455 Phase 2
0.7403 Intermediate Similarity NPD2978 Approved
0.7383 Intermediate Similarity NPD1774 Approved
0.7372 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD7685 Pre-registration
0.7357 Intermediate Similarity NPD4908 Phase 1
0.7353 Intermediate Similarity NPD1610 Phase 2
0.7348 Intermediate Similarity NPD6671 Approved
0.7347 Intermediate Similarity NPD4237 Approved
0.7347 Intermediate Similarity NPD4236 Phase 3
0.7347 Intermediate Similarity NPD1652 Phase 2
0.7338 Intermediate Similarity NPD1934 Approved
0.7333 Intermediate Similarity NPD4123 Phase 3
0.7323 Intermediate Similarity NPD968 Approved
0.7319 Intermediate Similarity NPD8651 Approved
0.7313 Intermediate Similarity NPD1548 Phase 1
0.731 Intermediate Similarity NPD5960 Phase 3
0.731 Intermediate Similarity NPD5588 Approved
0.7292 Intermediate Similarity NPD6653 Approved
0.729 Intermediate Similarity NPD5772 Approved
0.729 Intermediate Similarity NPD5773 Approved
0.7273 Intermediate Similarity NPD4060 Phase 1
0.7273 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3620 Phase 2
0.7254 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD2677 Approved
0.7246 Intermediate Similarity NPD3685 Discontinued
0.7241 Intermediate Similarity NPD7097 Phase 1
0.7239 Intermediate Similarity NPD5536 Phase 2
0.723 Intermediate Similarity NPD3060 Approved
0.723 Intermediate Similarity NPD4162 Approved
0.7208 Intermediate Similarity NPD4675 Approved
0.7208 Intermediate Similarity NPD4678 Approved
0.7206 Intermediate Similarity NPD1778 Approved
0.7205 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD6166 Phase 2
0.7205 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD6233 Phase 2
0.7197 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD3180 Approved
0.7183 Intermediate Similarity NPD3179 Approved
0.7181 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD4110 Phase 3
0.7181 Intermediate Similarity NPD4628 Phase 3
0.7179 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD2231 Phase 2
0.7174 Intermediate Similarity NPD2235 Phase 2
0.7153 Intermediate Similarity NPD3496 Discontinued
0.7152 Intermediate Similarity NPD7240 Approved
0.7152 Intermediate Similarity NPD6559 Discontinued
0.7152 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD3817 Phase 2
0.7133 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD6190 Approved
0.7132 Intermediate Similarity NPD1358 Approved
0.7124 Intermediate Similarity NPD2122 Discontinued
0.7122 Intermediate Similarity NPD4749 Approved
0.7121 Intermediate Similarity NPD821 Approved
0.7113 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD447 Suspended
0.7103 Intermediate Similarity NPD5735 Approved
0.7101 Intermediate Similarity NPD422 Phase 1
0.7101 Intermediate Similarity NPD6842 Approved
0.7101 Intermediate Similarity NPD6841 Approved
0.7101 Intermediate Similarity NPD6843 Phase 3
0.7095 Intermediate Similarity NPD5762 Approved
0.7095 Intermediate Similarity NPD5763 Approved
0.708 Intermediate Similarity NPD5125 Phase 3
0.708 Intermediate Similarity NPD6516 Phase 2
0.708 Intermediate Similarity NPD5846 Approved
0.708 Intermediate Similarity NPD5126 Approved
0.7075 Intermediate Similarity NPD4108 Discontinued
0.7073 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD2801 Approved
0.7063 Intermediate Similarity NPD7095 Approved
0.7059 Intermediate Similarity NPD52 Approved
0.7059 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7526 Approved
0.7047 Intermediate Similarity NPD2424 Discontinued
0.7042 Intermediate Similarity NPD9494 Approved
0.7027 Intermediate Similarity NPD2161 Phase 2
0.7025 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD2560 Approved
0.7025 Intermediate Similarity NPD2563 Approved
0.7023 Intermediate Similarity NPD3022 Approved
0.7023 Intermediate Similarity NPD3021 Approved
0.7014 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD6798 Discontinued
0.7013 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5177 Phase 3
0.6986 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6986 Remote Similarity NPD4340 Discontinued
0.6986 Remote Similarity NPD6355 Discontinued
0.6986 Remote Similarity NPD5124 Phase 1
0.6986 Remote Similarity NPD230 Phase 1
0.6981 Remote Similarity NPD3882 Suspended
0.698 Remote Similarity NPD3540 Phase 1
0.6978 Remote Similarity NPD776 Approved
0.6975 Remote Similarity NPD3787 Discontinued
0.6972 Remote Similarity NPD6584 Phase 3
0.6972 Remote Similarity NPD558 Phase 2
0.697 Remote Similarity NPD5844 Phase 1
0.6967 Remote Similarity NPD9365 Approved
0.6966 Remote Similarity NPD2674 Phase 3
0.6966 Remote Similarity NPD4062 Phase 3
0.6954 Remote Similarity NPD4535 Phase 3
0.6954 Remote Similarity NPD6331 Phase 2
0.6948 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6944 Remote Similarity NPD4625 Phase 3
0.6935 Remote Similarity NPD9296 Approved
0.6934 Remote Similarity NPD1182 Approved
0.6929 Remote Similarity NPD1608 Approved
0.6928 Remote Similarity NPD1511 Approved
0.6923 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6918 Remote Similarity NPD4140 Approved
0.6918 Remote Similarity NPD2238 Phase 2
0.6914 Remote Similarity NPD8127 Discontinued
0.6913 Remote Similarity NPD3539 Phase 1
0.6908 Remote Similarity NPD2219 Phase 1
0.6908 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6901 Remote Similarity NPD1820 Approved
0.6901 Remote Similarity NPD1819 Approved
0.6901 Remote Similarity NPD1817 Approved
0.6901 Remote Similarity NPD1818 Approved
0.6899 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6897 Remote Similarity NPD3145 Approved
0.6897 Remote Similarity NPD3144 Approved
0.6884 Remote Similarity NPD5585 Approved
0.6883 Remote Similarity NPD4739 Approved
0.6882 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6871 Remote Similarity NPD1933 Approved
0.6871 Remote Similarity NPD6071 Discontinued
0.6867 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6866 Remote Similarity NPD5535 Approved
0.6863 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6855 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6853 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6849 Remote Similarity NPD554 Clinical (unspecified phase)
0.6846 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6846 Remote Similarity NPD7033 Discontinued
0.6846 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6839 Remote Similarity NPD1512 Approved
0.6835 Remote Similarity NPD9384 Approved
0.6835 Remote Similarity NPD9381 Approved
0.6832 Remote Similarity NPD5604 Discontinued
0.6829 Remote Similarity NPD2970 Approved
0.6829 Remote Similarity NPD2969 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