Natural Product: NPC109322

Natural Product ID:  NPC109322
Common Name:   Etofylline
IUPAC Name:   7-(2-hydroxyethyl)-1,3-dimethylpurine-2,6-dione
Synonyms:   Beta-hydroxyethyl theophylline; Etofylline; Oxyethyltheophylline; Oxyphylline
Molecular Formula:   C9H12N4O3
Standard InCHIKey:  NWPRCRWQMGIBOT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H12N4O3/c1-11-7-6(8(15)12(2)9(11)16)13(3-4-14)5-10-7/h5,14H,3-4H2,1-2H3
Canonical SMILES:  OCCn1cnc2c1c(=O)n(C)c(=O)n2C
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO22033 Cnidium officinale Species Apiaceae Eukaryota TM-MC*
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota TM-MC*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1315 Individual Protein Adenosine A1 receptor Rattus norvegicus Ki = 105000 nM 3806581
NPT4262 Individual Protein Adenosine A2a receptor Cavia porcellus Ki = 135000 nM 3806581
NPT4059 Individual Protein Adenosine A2b receptor Homo sapiens Ki = 17300 nM 12014951
NPT2 Others Unspecified Activity = 43 % 10411473
NPT4059 Individual Protein Adenosine A2b receptor Homo sapiens Ki = 17300 nM 20537438
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 3162.3 nM PubChem BioAssay data set
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 2238.7 nM PubChem BioAssay data set
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 17782.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 4466.8 nM PubChem BioAssay data set
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency 89125.1 nM PubChem BioAssay data set
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency 4256.2 nM PubChem BioAssay data set
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency 22387.2 nM PubChem BioAssay data set
NPT698 Individual Protein Regulator of G-protein signaling 4 Homo sapiens Potency 67 nM PubChem BioAssay data set
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency 35481.3 nM PubChem BioAssay data set
NPT10 Individual Protein Geminin Homo sapiens Potency 461.1 nM PubChem BioAssay data set
NPT4263 Tissue Tissue Cavia porcellus Activity = 40 % 10.1007/s00044-006-0141-7
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 64.41 % 23571415
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 86.25 % 23571415
NPT2 Others Unspecified Potency 29847 nM PubChem BioAssay data set
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency 223.9 nM PubChem BioAssay data set
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency 3.2 nM PubChem BioAssay data set
NPT2 Others Unspecified AC50 10000 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 13333.2 nM PubChem BioAssay data set
NPT2 Others Unspecified AC50 6309.6 nM PubChem BioAssay data set

  Similar Natural Products 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 NPC109322 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
0.9402 High Similarity NPC180493
0.9115 High Similarity NPC256849
0.8947 High Similarity NPC303899
0.8609 High Similarity NPC47936
0.8347 Intermediate Similarity NPC252603
0.8276 Intermediate Similarity NPC75131
0.8115 Intermediate Similarity NPC158847
0.8017 Intermediate Similarity NPC148385
0.7886 Intermediate Similarity NPC278549
0.7872 Intermediate Similarity NPC321052
0.7591 Intermediate Similarity NPC226184
0.7591 Intermediate Similarity NPC167285
0.7591 Intermediate Similarity NPC76544
0.75 Intermediate Similarity NPC199790
0.7395 Intermediate Similarity NPC476561
0.7213 Intermediate Similarity NPC119133
0.7131 Intermediate Similarity NPC476099
0.7123 Intermediate Similarity NPC326694
0.6992 Remote Similarity NPC476562
0.6911 Remote Similarity NPC10466
0.6621 Remote Similarity NPC317821
0.6615 Remote Similarity NPC41958
0.6573 Remote Similarity NPC320818
0.6571 Remote Similarity NPC246193
0.6552 Remote Similarity NPC129756
0.6457 Remote Similarity NPC476564
0.6444 Remote Similarity NPC327579
0.6439 Remote Similarity NPC313547
0.6419 Remote Similarity NPC229974
0.64 Remote Similarity NPC189068
0.637 Remote Similarity NPC33996
0.6364 Remote Similarity NPC57279
0.6358 Remote Similarity NPC309832
0.6358 Remote Similarity NPC219313
0.6357 Remote Similarity NPC144223
0.6349 Remote Similarity NPC174114
0.6349 Remote Similarity NPC87981
0.6338 Remote Similarity NPC104011
0.6333 Remote Similarity NPC107374
0.6333 Remote Similarity NPC156461
0.6333 Remote Similarity NPC21448
0.6331 Remote Similarity NPC248007
0.6291 Remote Similarity NPC164665
0.6284 Remote Similarity NPC161659
0.6284 Remote Similarity NPC209525
0.6275 Remote Similarity NPC136349
0.625 Remote Similarity NPC269827
0.62 Remote Similarity NPC314152
0.6135 Remote Similarity NPC325906
0.6115 Remote Similarity NPC139776
0.609 Remote Similarity NPC185991
0.609 Remote Similarity NPC312187
0.609 Remote Similarity NPC211025
0.609 Remote Similarity NPC4837
0.609 Remote Similarity NPC85689
0.6074 Remote Similarity NPC324484
0.6054 Remote Similarity NPC262926
0.6051 Remote Similarity NPC321814
0.6051 Remote Similarity NPC472816
0.6051 Remote Similarity NPC328479
0.6051 Remote Similarity NPC207633
0.6026 Remote Similarity NPC150853
0.6016 Remote Similarity NPC293163
0.6014 Remote Similarity NPC61198
0.6013 Remote Similarity NPC212551
0.6013 Remote Similarity NPC130586
0.6013 Remote Similarity NPC302778
0.6013 Remote Similarity NPC164952
0.6 Remote Similarity NPC121222
0.6 Remote Similarity NPC59314
0.6 Remote Similarity NPC239737
0.5975 Remote Similarity NPC174802
0.5964 Remote Similarity NPC290959
0.5963 Remote Similarity NPC195140
0.5938 Remote Similarity NPC224076
0.5938 Remote Similarity NPC52238
0.5923 Remote Similarity NPC273327
0.5912 Remote Similarity NPC63433
0.5901 Remote Similarity NPC316618
0.5901 Remote Similarity NPC226245
0.5901 Remote Similarity NPC311197
0.5901 Remote Similarity NPC93365
0.5901 Remote Similarity NPC54320
0.5901 Remote Similarity NPC313754
0.5886 Remote Similarity NPC161224
0.5867 Remote Similarity NPC470141
0.5833 Remote Similarity NPC18335
0.5828 Remote Similarity NPC30326
0.5817 Remote Similarity NPC186619
0.5811 Remote Similarity NPC324009
0.5806 Remote Similarity NPC274384
0.5806 Remote Similarity NPC89147
0.58 Remote Similarity NPC470140
0.5789 Remote Similarity NPC470139
0.5782 Remote Similarity NPC287876
0.5779 Remote Similarity NPC74306
0.5779 Remote Similarity NPC315642
0.5772 Remote Similarity NPC319221
0.5742 Remote Similarity NPC251233
0.5742 Remote Similarity NPC318590
0.5742 Remote Similarity NPC211820
0.5723 Remote Similarity NPC323091
0.5714 Remote Similarity NPC14330
0.5705 Remote Similarity NPC177169
0.5705 Remote Similarity NPC317746
0.5686 Remote Similarity NPC210947
0.5669 Remote Similarity NPC232408
0.5669 Remote Similarity NPC64705
0.5655 Remote Similarity NPC261595
0.5649 Remote Similarity NPC332382
0.5644 Remote Similarity NPC472833
0.5639 Remote Similarity NPC317307
0.5638 Remote Similarity NPC470138
0.5629 Remote Similarity NPC126634
0.5621 Remote Similarity NPC324033
0.5621 Remote Similarity NPC321458
0.5612 Remote Similarity NPC327613
0.5607 Remote Similarity NPC164845
0.5606 Remote Similarity NPC326248
0.5606 Remote Similarity NPC187191
0.5603 Remote Similarity NPC68938

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC109322 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
0.9826 High Similarity NPD281 Approved
0.9658 High Similarity NPD1127 Approved
0.9658 High Similarity NPD1128 Approved
0.9417 High Similarity NPD282 Approved
0.9402 High Similarity NPD9544 Approved
0.9402 High Similarity NPD78 Approved
0.9138 High Similarity NPD580 Discontinued
0.9115 High Similarity NPD9358 Approved
0.9115 High Similarity NPD9359 Approved
0.8983 High Similarity NPD2221 Clinical (unspecified phase)
0.8898 High Similarity NPD9290 Approved
0.888 High Similarity NPD1119 Phase 2
0.8729 High Similarity NPD578 Discontinued
0.8661 High Similarity NPD535 Approved
0.8618 High Similarity NPD1775 Approved
0.8618 High Similarity NPD1085 Approved
0.8607 High Similarity NPD579 Clinical (unspecified phase)
0.8443 Intermediate Similarity NPD4262 Discontinued
0.8433 Intermediate Similarity NPD7531 Clinical (unspecified phase)
0.8347 Intermediate Similarity NPD76 Approved
0.8347 Intermediate Similarity NPD9289 Approved
0.8347 Intermediate Similarity NPD9292 Approved
0.8347 Intermediate Similarity NPD9288 Approved
0.8333 Intermediate Similarity NPD2253 Discontinued
0.8017 Intermediate Similarity NPD9086 Approved
0.7868 Intermediate Similarity NPD1117 Clinical (unspecified phase)
0.7852 Intermediate Similarity NPD1118 Discontinued
0.7398 Intermediate Similarity NPD8954 Approved
0.7398 Intermediate Similarity NPD8955 Approved
0.7213 Intermediate Similarity NPD9291 Approved
0.7113 Intermediate Similarity NPD2179 Discontinued
0.7 Intermediate Similarity NPD9360 Approved
0.6889 Remote Similarity NPD9408 Phase 3
0.6871 Remote Similarity NPD4183 Phase 3
0.6871 Remote Similarity NPD4182 Phase 3
0.6861 Remote Similarity NPD9633 Phase 3
0.6832 Remote Similarity NPD4155 Approved
0.6744 Remote Similarity NPD9373 Approved
0.6735 Remote Similarity NPD1730 Discontinued
0.672 Remote Similarity NPD9626 Clinical (unspecified phase)
0.6692 Remote Similarity NPD307 Approved
0.6689 Remote Similarity NPD9605 Phase 3
0.6667 Remote Similarity NPD870 Clinical (unspecified phase)
0.6645 Remote Similarity NPD5321 Phase 3
0.6641 Remote Similarity NPD9374 Approved
0.6571 Remote Similarity NPD248 Discontinued
0.6538 Remote Similarity NPD9375 Discontinued
0.6519 Remote Similarity NPD9409 Discontinued
0.6493 Remote Similarity NPD9606 Approved
0.6493 Remote Similarity NPD237 Clinical (unspecified phase)
0.6486 Remote Similarity NPD4240 Approved
0.6483 Remote Similarity NPD1808 Phase 1
0.6447 Remote Similarity NPD3708 Phase 2
0.6444 Remote Similarity NPD9607 Approved
0.6424 Remote Similarity NPD3041 Approved
0.6395 Remote Similarity NPD3696 Approved
0.6395 Remote Similarity NPD3695 Approved
0.6391 Remote Similarity NPD757 Phase 3
0.6345 Remote Similarity NPD1120 Approved
0.6345 Remote Similarity NPD1121 Approved
0.6333 Remote Similarity NPD249 Approved
0.6333 Remote Similarity NPD250 Approved
0.6331 Remote Similarity NPD9084 Phase 2
0.6284 Remote Similarity NPD193 Suspended
0.6275 Remote Similarity NPD548 Clinical (unspecified phase)
0.625 Remote Similarity NPD186 Discovery
0.625 Remote Similarity NPD195 Approved
0.6242 Remote Similarity NPD1017 Clinical (unspecified phase)
0.6242 Remote Similarity NPD1430 Approved
0.6242 Remote Similarity NPD3081 Clinical (unspecified phase)
0.6242 Remote Similarity NPD1431 Approved
0.6241 Remote Similarity NPD515 Phase 1
0.6225 Remote Similarity NPD7158 Phase 1
0.62 Remote Similarity NPD185 Approved
0.6148 Remote Similarity NPD9584 Phase 2
0.6138 Remote Similarity NPD547 Clinical (unspecified phase)
0.6138 Remote Similarity NPD545 Clinical (unspecified phase)
0.6135 Remote Similarity NPD1777 Approved
0.6135 Remote Similarity NPD1776 Approved
0.6118 Remote Similarity NPD166 Approved
0.6115 Remote Similarity NPD3107 Discontinued
0.6111 Remote Similarity NPD9632 Phase 3
0.609 Remote Similarity NPD283 Approved
0.6056 Remote Similarity NPD4812 Phase 1
0.6054 Remote Similarity NPD194 Clinical (unspecified phase)
0.6014 Remote Similarity NPD252 Clinical (unspecified phase)
0.6013 Remote Similarity NPD214 Approved
0.6013 Remote Similarity NPD213 Clinical (unspecified phase)
0.6013 Remote Similarity NPD338 Approved
0.6013 Remote Similarity NPD1369 Phase 2
0.6013 Remote Similarity NPD242 Approved
0.6013 Remote Similarity NPD1750 Clinical (unspecified phase)
0.6 Remote Similarity NPD2624 Phase 2
0.6 Remote Similarity NPD1250 Clinical (unspecified phase)
0.6 Remote Similarity NPD2646 Discontinued
0.6 Remote Similarity NPD8837 Clinical (unspecified phase)
0.5975 Remote Similarity NPD339 Approved
0.596 Remote Similarity NPD549 Approved
0.5951 Remote Similarity NPD3083 Approved
0.5942 Remote Similarity NPD1368 Approved
0.5938 Remote Similarity NPD169 Phase 2
0.5917 Remote Similarity NPD5666 Phase 2
0.5915 Remote Similarity NPD798 Discontinued
0.5909 Remote Similarity NPD171 Discontinued
0.5901 Remote Similarity NPD219 Phase 3
0.5901 Remote Similarity NPD216 Approved
0.5901 Remote Similarity NPD220 Clinical (unspecified phase)
0.5901 Remote Similarity NPD546 Clinical (unspecified phase)
0.5901 Remote Similarity NPD1732 Phase 3
0.5901 Remote Similarity NPD217 Approved
0.5901 Remote Similarity NPD218 Approved
0.5896 Remote Similarity NPD613 Phase 2
0.5886 Remote Similarity NPD7842 Phase 2
0.5878 Remote Similarity NPD9083 Clinical (unspecified phase)
0.5878 Remote Similarity NPD209 Clinical (unspecified phase)
0.5865 Remote Similarity NPD1816 Clinical (unspecified phase)
0.5833 Remote Similarity NPD8836 Approved
0.5806 Remote Similarity NPD9627 Approved
0.5802 Remote Similarity NPD2604 Approved
0.5793 Remote Similarity NPD516 Clinical (unspecified phase)
0.5782 Remote Similarity NPD8829 Clinical (unspecified phase)
0.5779 Remote Similarity NPD582 Approved
0.5775 Remote Similarity NPD1790 Clinical (unspecified phase)
0.5762 Remote Similarity NPD6112 Approved
0.5762 Remote Similarity NPD2602 Clinical (unspecified phase)
0.5753 Remote Similarity NPD2191 Discontinued
0.575 Remote Similarity NPD536 Clinical (unspecified phase)
0.5714 Remote Similarity NPD9195 Approved
0.5703 Remote Similarity NPD9189 Discontinued
0.5696 Remote Similarity NPD775 Approved
0.5678 Remote Similarity NPD3043 Approved
0.5678 Remote Similarity NPD3042 Approved
0.5676 Remote Similarity NPD1705 Discontinued
0.5674 Remote Similarity NPD8824 Phase 3
0.5667 Remote Similarity NPD1058 Discontinued
0.5655 Remote Similarity NPD247 Clinical (unspecified phase)
0.5649 Remote Similarity NPD9135 Approved
0.5649 Remote Similarity NPD9134 Approved
0.5649 Remote Similarity NPD9255 Phase 2
0.5639 Remote Similarity NPD9629 Approved
0.5629 Remote Similarity NPD9484 Clinical (unspecified phase)
0.5621 Remote Similarity NPD2647 Phase 3
0.5617 Remote Similarity NPD1731 Clinical (unspecified phase)
0.5612 Remote Similarity NPD1623 Approved

Structure

External Identifiers

PubChem CID   1892
ChEMBL   CHEMBL699
ZINC  

Physicochemical Properties

Molecular Weight:  224.09
ALogP:  -0.9705
MLogP:  1.68
XLogP:  -1.334
# Rotatable Bonds:  5
Polar Surface Area:  78.67
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  16

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