NP-MRD: Showing NP-Card for 3-methylthymidine (NP0258877)

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Record Information

Version

2.0

Created at

2022-09-08 00:32:54 UTC

Updated at

2022-09-08 00:32:55 UTC

NP-MRD ID

NP0258877

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-methylthymidine

Description

3-Methylthymidine belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. 3-methylthymidine is found in Streptomyces microflavus. 3-Methylthymidine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.8423    2.4109    1.7025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3945    1.2626    0.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0561    1.0636    0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6328    0.0287   -0.1947 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234   -0.2205   -0.5487 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5994    1.0145   -0.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9683    0.3397   -0.7302 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1933    0.3035   -2.1172 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6860   -1.0657   -0.2427 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7372   -1.4580    0.7712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7024   -0.5208    1.8047 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4093   -1.0474    0.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5988   -0.8194   -0.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2326   -1.8075   -1.3385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991   -0.6500   -0.3347 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8896   -1.5895   -0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3423    0.3763    0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5668    0.5148    0.6741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0038    3.1541    1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9613    2.1340    2.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7471    2.8981    1.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3151    1.7674    0.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8297   -0.6638   -1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3690    1.7012   -1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6478    1.4937    0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7565    0.8495   -0.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644   -0.5711   -2.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6663   -1.7787   -1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6098   -2.4917    1.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7259   -1.3544    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3529    0.2146    1.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9069   -1.1889   -0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6801   -1.6978   -1.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7721   -2.6019   -0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5 12  1  0
 12  9  1  0
  9 10  1  0
 10 11  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 17  1  0
 17 18  2  0
 17 15  1  0
 15 16  1  0
 15 13  1  0
 13 14  2  0
  9  7  1  0
 13  4  1  0
  7 26  1  1
  8 27  1  0
  6 24  1  0
  6 25  1  0
  5 23  1  6
  9 28  1  6
 10 29  1  0
 10 30  1  0
 11 31  1  0
  3 22  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
M  END


  Mrv0541 05031421412D          

 21 22  0  0  1  0            999 V2000
   -0.6110   -1.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7011   -0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7604   -0.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2754   -1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    2.2902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9897    1.8053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9097    1.0206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5450   -0.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3957    0.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8806   -0.2280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    0.3532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9458    2.8672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    3.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300   -1.6491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312    1.1931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347    1.0206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5872    2.6647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1187    2.6201    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949    1.1497    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  6  0  0  0
  8  7  1  0  0  0  0
  9  3  1  0  0  0  0
 10  6  1  0  0  0  0
 12  2  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  4  1  0  0  0  0
  9 13  1  6  0  0  0
 13 11  1  0  0  0  0
 14  5  1  0  0  0  0
  7 15  1  1  0  0  0
 16 10  2  0  0  0  0
 17 11  2  0  0  0  0
 18  8  1  0  0  0  0
 18  9  1  0  0  0  0
  7 19  1  6  0  0  0
  8 20  1  1  0  0  0
  9 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0258877

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(O)C[C@@]([H])(O[C@]1([H])CO)N1C=C(C)C(=O)N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N2O5/c1-6-4-13(11(17)12(2)10(6)16)9-3-7(15)8(5-14)18-9/h4,7-9,14-15H,3,5H2,1-2H3/t7-,8+,9+/m0/s1

> <INCHI_KEY>
JCVDICFLPGDHAT-DJLDLDEBSA-N

> <FORMULA>
C11H16N2O5

> <MOLECULAR_WEIGHT>
256.2551

> <EXACT_MASS>
256.105921632

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
25.00100814948253

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,5-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

> <ALOGPS_LOGP>
-1.14

> <JCHEM_LOGP>
-0.8953775236666662

> <ALOGPS_LOGS>
-0.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.787555381900546

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.894924423418356

> <JCHEM_PKA_STRONGEST_BASIC>
-2.978083590090309

> <JCHEM_POLAR_SURFACE_AREA>
90.30999999999999

> <JCHEM_REFRACTIVITY>
60.3087

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,5-dimethylpyrimidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   12                                                            
CONECT    3    7    9                                                       
CONECT    4    6   13                                                       
CONECT    5    8   14                                                       
CONECT    6    1    4   10                                                  
CONECT    7    3    8   15   19                                             
CONECT    8    5    7   18   20                                             
CONECT    9    3   13   18   21                                             
CONECT   10    6   12   16                                                  
CONECT   11   12   13   17                                                  
CONECT   12    2   10   11                                                  
CONECT   13    4    9   11                                                  
CONECT   14    5                                                            
CONECT   15    7                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18    8    9                                                       
CONECT   19    7                                                            
CONECT   20    8                                                            
CONECT   21    9                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
Methylthymidine	MeSH

Chemical Formula

C₁₁H₁₆N₂O₅

Average Mass

256.2551 Da

Monoisotopic Mass

256.10592 Da

IUPAC Name

1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,5-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,5-dimethylpyrimidine-2,4-dione

CAS Registry Number

Not Available

SMILES

[H][C@]1(O)C[C@@]([H])(O[C@]1([H])CO)N1C=C(C)C(=O)N(C)C1=O

InChI Identifier

InChI=1S/C11H16N2O5/c1-6-4-13(11(17)12(2)10(6)16)9-3-7(15)8(5-14)18-9/h4,7-9,14-15H,3,5H2,1-2H3/t7-,8+,9+/m0/s1

InChI Key

JCVDICFLPGDHAT-DJLDLDEBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces microflavus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Pyrimidine 2'-deoxyribonucleosides

Direct Parent

Pyrimidine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Pyrimidine 2'-deoxyribonucleoside
Pyrimidone
Hydropyrimidine
Pyrimidine
Heteroaromatic compound
Tetrahydrofuran
Vinylogous amide
Lactam
Secondary alcohol
Urea
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.1	ALOGPS
logP	-0.9	ChemAxon
logS	-0.35	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	90.31 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.31 m³·mol⁻¹	ChemAxon
Polarizability	25 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65062

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-methylthymidine (NP0258877)

MOL for NP0258877 (3-methylthymidine)

3D MOL for NP0258877 (3-methylthymidine)

3D SDF for NP0258877 (3-methylthymidine)

3D-SDF for NP0258877 (3-methylthymidine)

PDB for NP0258877 (3-methylthymidine)

3D PDB for NP0258877 (3-methylthymidine)

SMILES for NP0258877 (3-methylthymidine)

INCHI for NP0258877 (3-methylthymidine)

Structure for NP0258877 (3-methylthymidine)

3D Structure for NP0258877 (3-methylthymidine)