Summary

Full namehydroxy-N6-threonylcarbamoyladenosine
Short nameht6A
MODOMICS code2165A
Nature of the modified residueNatural
RNAMods code«
Residue unique ID181
Found in RNAYes
Related nucleotides417
Found in phylogenyEukaryota
Found naturally in RNA typestRNA

Chemical information

Sum formulaC15H20N6O9
Type of moietynucleoside
Degeneracynot applicable
SMILESOC(C(NC(Nc1ncnc2c1nc[n]2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)=O)C(O)CO)=O
logP-3.1704
TPSA232.41
Number of atoms30
Number of Hydrogen Bond Acceptors 1 (HBA1)14
Number of Hydrogen Bond Acceptors 2 (HBA2)15
Number of Hydrogen Bond Donors (HBD)8
PDB no exac match , link to the most similar ligand AET
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0041623
InChIInChI=1S/C15H20N6O9/c22-1-5(24)7(14(27)28)19-15(29)20-11-8-12(17-3-16-11)21(4-18-8)13-10(26)9(25)6(2-23)30-13/h3-7,9-10,13,22-26H,1-2H2,(H,27,28)(H2,16,17,19,20,29)/t5?,6-,7?,9-,10-,13-/m1/s1
InChIKeyVNCHNCDAHRIAAU-HZPYULPISA-N
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 

* Chemical properties calculated with Open Babel - O'Boyle et al. Open Babel: An open chemical toolbox. J Cheminform 3, 33 (2011) (link)


Download Structures

2D   .png .mol .mol2 .sdf .pdb .smi
3D   .mol .mol2 .sdf .pdb

Tautomers

Tautomers SMILES
O=C(C(NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #0
OC(C(NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)C=O)O tautomer #1
OC(C(NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(=O)CO)O tautomer #2
OC(C(=NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #3
O=C(C(NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #4
OC(C(NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)C=O)O tautomer #5
OC(C(NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(=O)CO)O tautomer #6
OC(C(=NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #7
OC(C(NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)=C(O)CO)O tautomer #8
O=C(C(NC(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #9
OC(C(NC(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)C=O)O tautomer #10
OC(C(NC(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)C(=O)CO)O tautomer #11
OC(C(=NC(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #12
OC(C(NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)=C(O)CO)O tautomer #13
O=C(C(NC(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #14
OC(C(NC(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)C=O)O tautomer #15
OC(C(NC(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(=O)CO)O tautomer #16
OC(C(=NC(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #17
OC(C(NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)=CO)O tautomer #18
OC(=C(NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #19
O=C(C(N=C(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #20
OC(C(NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)=CO)O tautomer #21
OC(C(NC(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)=C(O)CO)O tautomer #22
OC(=C(NC(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #23
O=C(C(N=C(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #24
O=C(C(NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #25
OC(C(NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)C=O)O tautomer #26
OC(C(NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(=O)CO)O tautomer #27
OC(C(=NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #28
OC(C(NC(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)=O)=C(O)CO)O tautomer #29
O=C(C(NC(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #30
OC(C(NC(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)=O)C(O)C=O)O tautomer #31
OC(C(NC(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)=O)C(=O)CO)O tautomer #32
OC(C(=NC(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #33
O=C(C(NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #34
OC(C(NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)C=O)O tautomer #35
OC(C(NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(=O)CO)O tautomer #36
OC(C(=NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #37
OC(C(NC(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)=CO)O tautomer #38
OC(=C(NC(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #39
O=C(C(N=C(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #40
OC(C(NC(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)=CO)O tautomer #41
OC(C(NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)=C(O)CO)O tautomer #42
OC(=C(NC(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #43
O=C(C(N=C(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #44
OC(C(NC(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)=O)=C(O)CO)O tautomer #45
OC(C(NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)=C(O)CO)O tautomer #46
OC(=C(N=C(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #47
OC(=C(N=C(Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #48
OC(C(NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)=CO)O tautomer #49
OC(=C(NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #50
OC(C(NC(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)=O)C(O)=CO)O tautomer #51
OC(=C(NC(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)=O)C(O)CO)O tautomer #52
O=C(C(N=C(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #53
OC(C(NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)=CO)O tautomer #54
OC(=C(NC(=Nc1ncnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #55
OC(=C(N=C(N=c1nc[nH]c2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #56
OC(=C(N=C(N=c1[nH]cnc2c1ncn2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #57
OC(=C(N=C(N=C1N=CN=C2C1N=CN2C3OC(CO)C(O)C3O)O)C(O)CO)O tautomer #58

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
ht6A ht6A ht6A

* CYP Metabolic sites predicted with SMARTCyp. SMARTCyp is a method for prediction of which sites in a molecule that are most liable to metabolism by Cytochrome P450. It has been shown to be applicable to metabolism by the isoforms 1A2, 2A6, 2B6, 2C8, 2C19, 2E1, and 3A4 (CYP3A4), and specific models for the isoform 2C9 (CYP2C9) and isoform 2D6 (CYP2D6). CYP3A4, CYP2D6, and CYP2C9 are the three of the most important enzymes in drug metabolism since they are involved in the metabolism of more than half of the drugs used today. The three top-ranked atoms are highlighted. See: SmartCYP and SmartCYP - background; Patrik Rydberg, David E. Gloriam, Lars Olsen, The SMARTCyp cytochrome P450 metabolism prediction server, Bioinformatics, Volume 26, Issue 23, 1 December 2010, Pages 2988–2989 (link)


LC-MS Information

Monoisotopic mass428.1292
Average mass428.354
[M+H]+ not available
Product ions not available
Normalized LC elution time * not available
LC elution order/characteristics not available

* normalized to guanosine (G), measured with a RP C-18 column with acetonitrile/ammonium acetate as mobile phase.

Publications

Title Authors Journal Details PubMed Id DOI
Hydroxylation of a conserved tRNA modification establishes non-universal genetic code in echinoderm mitochondria. Nagao A, Ohara M, Miyauchi K, Yokobori SI, Yamagishi A, Watanabe K, Suzuki T... Nat Struct Mol Biol [details] 28783151 -

Last modification of this entry: Sept. 29, 2021


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