Natural Product: NPC319221

Natural Product ID:  NPC319221
Common Name:   8-Hydroxyguanosine
IUPAC Name:   2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,7-dihydropurine-6,8-dione
Synonyms:   8-Hydroxyguanosine
Molecular Formula:   C10H13N5O6
Standard InCHIKey:  FPGSEBKFEJEOSA-UMMCILCDSA-N
Standard InCHI:  InChI=1S/C10H13N5O6/c11-9-13-6-3(7(19)14-9)12-10(20)15(6)8-5(18)4(17)2(1-16)21-8/h2,4-5,8,16-18H,1H2,(H,12,20)(H3,11,13,14,19)/t2-,4-,5-,8-/m1/s1
Canonical SMILES:  OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1c(O)nc2c1[nH]c(=N)nc2O
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
NPO1797 Homo sapiens Species Hominidae Eukaryota blood PMID[12391605]
NPO1797 Homo sapiens Species Hominidae Eukaryota cerebrospinal fluid PMID[12391605]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2813 Cell Line Friend leukemia cell line ID50 = 8.00E-06 nM 3861870
NPT116 Cell Line HL-60 Homo sapiens ID50 = 8.00E-06 nM 3861870

  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 NPC319221 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
0.9918 High Similarity NPC324009
0.968 High Similarity NPC61198
0.96 High Similarity NPC262926
0.9167 High Similarity NPC211820
0.9167 High Similarity NPC251233
0.916 High Similarity NPC186619
0.9098 High Similarity NPC89147
0.9098 High Similarity NPC177169
0.9098 High Similarity NPC274384
0.903 High Similarity NPC232408
0.903 High Similarity NPC64705
0.9023 High Similarity NPC318590
0.8955 High Similarity NPC317746
0.8923 High Similarity NPC320818
0.8788 High Similarity NPC30326
0.848 Intermediate Similarity NPC327579
0.8394 Intermediate Similarity NPC315642
0.8394 Intermediate Similarity NPC74306
0.8176 Intermediate Similarity NPC14590
0.8085 Intermediate Similarity NPC164665
0.8014 Intermediate Similarity NPC156461
0.8014 Intermediate Similarity NPC107374
0.8014 Intermediate Similarity NPC21448
0.7958 Intermediate Similarity NPC189068
0.7902 Intermediate Similarity NPC309832
0.7902 Intermediate Similarity NPC269827
0.7902 Intermediate Similarity NPC219313
0.7872 Intermediate Similarity NPC229974
0.7785 Intermediate Similarity NPC311197
0.7785 Intermediate Similarity NPC54320
0.7785 Intermediate Similarity NPC313754
0.7755 Intermediate Similarity NPC321052
0.773 Intermediate Similarity NPC161659
0.773 Intermediate Similarity NPC209525
0.7718 Intermediate Similarity NPC52238
0.7687 Intermediate Similarity NPC211025
0.7687 Intermediate Similarity NPC185991
0.7687 Intermediate Similarity NPC85689
0.7635 Intermediate Similarity NPC321814
0.7635 Intermediate Similarity NPC472816
0.7622 Intermediate Similarity NPC314152
0.7606 Intermediate Similarity NPC317821
0.7584 Intermediate Similarity NPC130586
0.7584 Intermediate Similarity NPC302778
0.7584 Intermediate Similarity NPC164952
0.7584 Intermediate Similarity NPC212551
0.755 Intermediate Similarity NPC239737
0.7533 Intermediate Similarity NPC174802
0.75 Intermediate Similarity NPC150853
0.75 Intermediate Similarity NPC326694
0.7483 Intermediate Similarity NPC121222
0.7483 Intermediate Similarity NPC224076
0.7436 Intermediate Similarity NPC261595
0.7434 Intermediate Similarity NPC316618
0.7434 Intermediate Similarity NPC226245
0.74 Intermediate Similarity NPC207633
0.7389 Intermediate Similarity NPC321458
0.7389 Intermediate Similarity NPC324033
0.7333 Intermediate Similarity NPC161224
0.7292 Intermediate Similarity NPC129756
0.72 Intermediate Similarity NPC136349
0.7197 Intermediate Similarity NPC323091
0.7059 Intermediate Similarity NPC328479
0.6992 Remote Similarity NPC313547
0.6986 Remote Similarity NPC33996
0.6953 Remote Similarity NPC10466
0.6943 Remote Similarity NPC195140
0.6909 Remote Similarity NPC189261
0.6848 Remote Similarity NPC326529
0.6825 Remote Similarity NPC320256
0.6822 Remote Similarity NPC59314
0.6807 Remote Similarity NPC324198
0.6807 Remote Similarity NPC319100
0.6772 Remote Similarity NPC93365
0.6728 Remote Similarity NPC324484
0.6718 Remote Similarity NPC119133
0.6707 Remote Similarity NPC290959
0.6707 Remote Similarity NPC326082
0.6687 Remote Similarity NPC325906
0.6667 Remote Similarity NPC41958
0.6647 Remote Similarity NPC313897
0.6589 Remote Similarity NPC293163
0.6457 Remote Similarity NPC313514
0.6449 Remote Similarity NPC63433
0.6369 Remote Similarity NPC222174
0.6341 Remote Similarity NPC321393
0.6286 Remote Similarity NPC24589
0.6271 Remote Similarity NPC282458
0.6271 Remote Similarity NPC78941
0.619 Remote Similarity NPC33382
0.6154 Remote Similarity NPC125659
0.6154 Remote Similarity NPC168702
0.6127 Remote Similarity NPC240084
0.6119 Remote Similarity NPC476561
0.5979 Remote Similarity NPC157821
0.5973 Remote Similarity NPC180462
0.5957 Remote Similarity NPC276373
0.5926 Remote Similarity NPC5802
0.5879 Remote Similarity NPC250178
0.5875 Remote Similarity NPC174020
0.585 Remote Similarity NPC139776
0.5797 Remote Similarity NPC476562
0.5779 Remote Similarity NPC57279
0.5772 Remote Similarity NPC109322
0.5752 Remote Similarity NPC287876
0.5749 Remote Similarity NPC60537
0.5743 Remote Similarity NPC470142
0.5736 Remote Similarity NPC328806
0.5733 Remote Similarity NPC248007
0.5732 Remote Similarity NPC470141
0.5729 Remote Similarity NPC103388
0.5686 Remote Similarity NPC14330
0.5683 Remote Similarity NPC476564
0.5674 Remote Similarity NPC75131
0.566 Remote Similarity NPC210947
0.5659 Remote Similarity NPC190334
0.5659 Remote Similarity NPC62927
0.5658 Remote Similarity NPC144223
0.5649 Remote Similarity NPC246193
0.5625 Remote Similarity NPC185903
0.5613 Remote Similarity NPC470138
0.5604 Remote Similarity NPC107160
0.56 Remote Similarity NPC5707

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC319221 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
0.968 High Similarity NPD252 Clinical (unspecified phase)
0.9291 High Similarity NPD194 Clinical (unspecified phase)
0.928 High Similarity NPD9632 Phase 3
0.9231 High Similarity NPD549 Approved
0.8571 High Similarity NPD3086 Phase 3
0.85 High Similarity NPD3085 Phase 1
0.848 Intermediate Similarity NPD9607 Approved
0.84 Intermediate Similarity NPD9606 Approved
0.8394 Intermediate Similarity NPD582 Approved
0.8345 Intermediate Similarity NPD4074 Clinical (unspecified phase)
0.8209 Intermediate Similarity NPD209 Clinical (unspecified phase)
0.816 Intermediate Similarity NPD9374 Approved
0.8134 Intermediate Similarity NPD545 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD307 Approved
0.8014 Intermediate Similarity NPD250 Approved
0.8014 Intermediate Similarity NPD249 Approved
0.8 Intermediate Similarity NPD547 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD536 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD9373 Approved
0.7902 Intermediate Similarity NPD195 Approved
0.7902 Intermediate Similarity NPD186 Discovery
0.7785 Intermediate Similarity NPD217 Approved
0.7785 Intermediate Similarity NPD216 Approved
0.7785 Intermediate Similarity NPD220 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD219 Phase 3
0.7785 Intermediate Similarity NPD218 Approved
0.7703 Intermediate Similarity NPD1369 Phase 2
0.7703 Intermediate Similarity NPD1750 Clinical (unspecified phase)
0.7687 Intermediate Similarity NPD283 Approved
0.7676 Intermediate Similarity NPD1430 Approved
0.7676 Intermediate Similarity NPD1431 Approved
0.7667 Intermediate Similarity NPD2624 Phase 2
0.7622 Intermediate Similarity NPD185 Approved
0.7603 Intermediate Similarity NPD775 Approved
0.7584 Intermediate Similarity NPD338 Approved
0.7584 Intermediate Similarity NPD242 Approved
0.7584 Intermediate Similarity NPD3107 Discontinued
0.7584 Intermediate Similarity NPD214 Approved
0.7584 Intermediate Similarity NPD213 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD9409 Discontinued
0.755 Intermediate Similarity NPD2646 Discontinued
0.755 Intermediate Similarity NPD1732 Phase 3
0.7533 Intermediate Similarity NPD339 Approved
0.7517 Intermediate Similarity NPD166 Approved
0.75 Intermediate Similarity NPD9375 Discontinued
0.7483 Intermediate Similarity NPD169 Phase 2
0.7483 Intermediate Similarity NPD193 Suspended
0.7465 Intermediate Similarity NPD1808 Phase 1
0.745 Intermediate Similarity NPD353 Discontinued
0.7436 Intermediate Similarity NPD247 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD1120 Approved
0.7324 Intermediate Similarity NPD1121 Approved
0.7293 Intermediate Similarity NPD237 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD9605 Phase 3
0.7246 Intermediate Similarity NPD515 Phase 1
0.72 Intermediate Similarity NPD548 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD4716 Approved
0.7068 Intermediate Similarity NPD9584 Phase 2
0.7063 Intermediate Similarity NPD2647 Phase 3
0.7048 Intermediate Similarity NPD4744 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD9360 Approved
0.6993 Remote Similarity NPD7842 Phase 2
0.6951 Remote Similarity NPD5666 Phase 2
0.6899 Remote Similarity NPD9626 Clinical (unspecified phase)
0.6864 Remote Similarity NPD1692 Approved
0.6822 Remote Similarity NPD8837 Clinical (unspecified phase)
0.6807 Remote Similarity NPD4171 Clinical (unspecified phase)
0.679 Remote Similarity NPD7988 Suspended
0.6786 Remote Similarity NPD798 Discontinued
0.6772 Remote Similarity NPD546 Clinical (unspecified phase)
0.6766 Remote Similarity NPD1412 Clinical (unspecified phase)
0.6736 Remote Similarity NPD248 Discontinued
0.6718 Remote Similarity NPD9291 Approved
0.6705 Remote Similarity NPD2152 Clinical (unspecified phase)
0.6687 Remote Similarity NPD1776 Approved
0.6687 Remote Similarity NPD1777 Approved
0.6667 Remote Similarity NPD1816 Clinical (unspecified phase)
0.6646 Remote Similarity NPD516 Clinical (unspecified phase)
0.6605 Remote Similarity NPD3083 Approved
0.6597 Remote Similarity NPD870 Clinical (unspecified phase)
0.659 Remote Similarity NPD5683 Clinical (unspecified phase)
0.659 Remote Similarity NPD6417 Clinical (unspecified phase)
0.659 Remote Similarity NPD5684 Clinical (unspecified phase)
0.659 Remote Similarity NPD5682 Phase 3
0.6514 Remote Similarity NPD2630 Approved
0.6514 Remote Similarity NPD2631 Clinical (unspecified phase)
0.6514 Remote Similarity NPD2632 Approved
0.6493 Remote Similarity NPD9416 Phase 3
0.6493 Remote Similarity NPD9417 Phase 3
0.6477 Remote Similarity NPD4054 Clinical (unspecified phase)
0.6457 Remote Similarity NPD7138 Phase 2
0.6357 Remote Similarity NPD1368 Approved
0.6242 Remote Similarity NPD282 Approved
0.6234 Remote Similarity NPD1118 Discontinued
0.6225 Remote Similarity NPD1119 Phase 2
0.6188 Remote Similarity NPD3708 Phase 2
0.6149 Remote Similarity NPD1354 Approved
0.6149 Remote Similarity NPD1355 Clinical (unspecified phase)
0.6149 Remote Similarity NPD1356 Approved
0.6142 Remote Similarity NPD6381 Phase 2
0.6107 Remote Similarity NPD9633 Phase 3
0.6101 Remote Similarity NPD7531 Clinical (unspecified phase)
0.6099 Remote Similarity NPD9406 Approved
0.609 Remote Similarity NPD2253 Discontinued
0.6085 Remote Similarity NPD2877 Clinical (unspecified phase)
0.6085 Remote Similarity NPD2876 Phase 3
0.6076 Remote Similarity NPD7158 Phase 1
0.6032 Remote Similarity NPD2965 Clinical (unspecified phase)
0.6022 Remote Similarity NPD5665 Clinical (unspecified phase)
0.6021 Remote Similarity NPD2824 Phase 2
0.6014 Remote Similarity NPD9408 Phase 3
0.6012 Remote Similarity NPD231 Clinical (unspecified phase)
0.6012 Remote Similarity NPD5768 Phase 2
0.6 Remote Similarity NPD1061 Clinical (unspecified phase)
0.5966 Remote Similarity NPD1046 Clinical (unspecified phase)
0.595 Remote Similarity NPD6036 Suspended
0.5933 Remote Similarity NPD1127 Approved
0.5933 Remote Similarity NPD1128 Approved
0.5906 Remote Similarity NPD281 Approved
0.5868 Remote Similarity NPD3697 Discontinued
0.5868 Remote Similarity NPD2604 Approved
0.5854 Remote Similarity NPD9429 Discontinued
0.5849 Remote Similarity NPD1117 Clinical (unspecified phase)
0.5839 Remote Similarity NPD1730 Discontinued
0.58 Remote Similarity NPD4812 Phase 1
0.5783 Remote Similarity NPD1731 Clinical (unspecified phase)
0.5778 Remote Similarity NPD223 Clinical (unspecified phase)
0.5769 Remote Similarity NPD535 Approved
0.5769 Remote Similarity NPD1063 Phase 2
0.5752 Remote Similarity NPD8829 Clinical (unspecified phase)
0.5749 Remote Similarity NPD2180 Approved
0.5745 Remote Similarity NPD691 Discontinued
0.5742 Remote Similarity NPD9083 Clinical (unspecified phase)
0.5737 Remote Similarity NPD4599 Clinical (unspecified phase)
0.5736 Remote Similarity NPD2902 Phase 2
0.5736 Remote Similarity NPD2903 Clinical (unspecified phase)
0.5733 Remote Similarity NPD9084 Phase 2
0.5725 Remote Similarity NPD9585 Discontinued
0.5714 Remote Similarity NPD4495 Phase 1
0.5692 Remote Similarity NPD9102 Approved
0.5692 Remote Similarity NPD9103 Approved
0.5659 Remote Similarity NPD9603 Phase 3
0.5659 Remote Similarity NPD9604 Approved
0.5659 Remote Similarity NPD9602 Phase 3
0.5646 Remote Similarity NPD578 Discontinued
0.5643 Remote Similarity NPD9415 Clinical (unspecified phase)
0.5625 Remote Similarity NPD3695 Approved
0.5625 Remote Similarity NPD3696 Approved
0.5607 Remote Similarity NPD527 Clinical (unspecified phase)
0.56 Remote Similarity NPD8830 Phase 3

Structure

External Identifiers

PubChem CID   65131
ChEMBL   CHEMBL1688964
ZINC  

Physicochemical Properties

Molecular Weight:  299.09
ALogP:  -2.6755
MLogP:  1.35
XLogP:  -2.111
# Rotatable Bonds:  7
Polar Surface Area:  176.44
# H-Bond Aceptor:  10
# H-Bond Donor:  7
# Rings:  3
# Heavy Atoms:  21

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