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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:44 UTC
HMDB IDHMDB0014789
Secondary Accession Numbers
  • HMDB14789
Metabolite Identification
Common NameDyphylline
DescriptionDyphylline is only found in individuals that have used or taken this drug. It is a theophylline derivative with broncho- and vasodilator properties. It is used in the treatment of asthma, cardiac dyspnea, and bronchitis. [PubChem]The bronchodilatory action of dyphylline, as with other xanthines, is thought to be mediated through competitive inhibition of phosphodiesterase with a resulting increase in cyclic AMP producing relaxation of bronchial smooth muscle as well as antagonism of adenosine receptors.
Structure
Data?1582753221
Synonyms
ValueSource
(+-)-7-(2,3-Dihydroxypropyl)theophyllineChEBI
(+-)-DiprophyllineChEBI
(+-)-DyphyllineChEBI
(1,2-Dihydroxy-3-propyl)thiophyllinChEBI
1,3-Dimethyl-7-(2,3-dihydroxypropyl)xanthineChEBI
7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthineChEBI
7-(2,3-Dihydroxypropyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dioneChEBI
7-(2,3-Dihydroxypropyl)theophyllineChEBI
7-(beta,gamma-Dihydroxypropyl)theophyllineChEBI
Dihydroxypropyl theopylinChEBI
DiprofilinaChEBI
DiprophyllineChEBI
DiprophyllinumChEBI
LufyllinKegg
7-(b,g-Dihydroxypropyl)theophyllineGenerator
7-(Β,γ-dihydroxypropyl)theophyllineGenerator
Dihydroxypropyl theophyllineHMDB
DiprofillinHMDB
DiprofillineHMDB
DiprophyllinHMDB
DipropyllineHMDB
DTHMDB
NeothyllineHMDB
DihydroxypropyltheophyllineHMDB
DiphyllineHMDB
Savage brand OF dyphyllineHMDB
Wallace brand OF dyphyllineHMDB
DilinHMDB
Dilor brand OF dyphyllineHMDB
Hauck brand OF dyphyllineHMDB
DylixHMDB
Lunsco brand OF dyphyllineHMDB
Major brand OF dyphyllineHMDB
Chemical FormulaC10H14N4O4
Average Molecular Weight254.2426
Monoisotopic Molecular Weight254.101504956
IUPAC Name7-(2,3-dihydroxypropyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Namedyphylline
CAS Registry Number479-18-5
SMILES
CN1C2=C(N(CC(O)CO)C=N2)C(=O)N(C)C1=O
InChI Identifier
InChI=1S/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3
InChI KeyKSCFJBIXMNOVSH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,2-diol
  • Lactam
  • Urea
  • Secondary alcohol
  • Azacycle
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point161.5 °CNot Available
Boiling Point589.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility14.3 g/LNot Available
LogP-1.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility14.3 g/LALOGPS
logP-0.98ALOGPS
logP-1.9ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)13.91ChemAxon
pKa (Strongest Basic)-0.97ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.9 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.09 m³·mol⁻¹ChemAxon
Polarizability24.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+157.031661259
DarkChem[M-H]-155.29431661259
DeepCCS[M+H]+156.14730932474
DeepCCS[M-H]-153.75230932474
DeepCCS[M-2H]-187.01730932474
DeepCCS[M+Na]+162.15130932474
AllCCS[M+H]+155.732859911
AllCCS[M+H-H2O]+152.132859911
AllCCS[M+NH4]+158.932859911
AllCCS[M+Na]+159.932859911
AllCCS[M-H]-157.432859911
AllCCS[M+Na-2H]-157.432859911
AllCCS[M+HCOO]-157.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DyphyllineCN1C2=C(N(CC(O)CO)C=N2)C(=O)N(C)C1=O2897.7Standard polar33892256
DyphyllineCN1C2=C(N(CC(O)CO)C=N2)C(=O)N(C)C1=O1800.0Standard non polar33892256
DyphyllineCN1C2=C(N(CC(O)CO)C=N2)C(=O)N(C)C1=O2385.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dyphylline,1TMS,isomer #1CN1C(=O)C2=C(N=CN2CC(CO)O[Si](C)(C)C)N(C)C1=O2343.5Semi standard non polar33892256
Dyphylline,1TMS,isomer #2CN1C(=O)C2=C(N=CN2CC(O)CO[Si](C)(C)C)N(C)C1=O2350.7Semi standard non polar33892256
Dyphylline,2TMS,isomer #1CN1C(=O)C2=C(N=CN2CC(CO[Si](C)(C)C)O[Si](C)(C)C)N(C)C1=O2324.8Semi standard non polar33892256
Dyphylline,1TBDMS,isomer #1CN1C(=O)C2=C(N=CN2CC(CO)O[Si](C)(C)C(C)(C)C)N(C)C1=O2589.5Semi standard non polar33892256
Dyphylline,1TBDMS,isomer #2CN1C(=O)C2=C(N=CN2CC(O)CO[Si](C)(C)C(C)(C)C)N(C)C1=O2595.7Semi standard non polar33892256
Dyphylline,2TBDMS,isomer #1CN1C(=O)C2=C(N=CN2CC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N(C)C1=O2799.7Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00651 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00651 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00651
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00030143
Chemspider ID3070
KEGG Compound IDC07819
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDyphylline
METLIN IDNot Available
PubChem Compound3182
PDB IDNot Available
ChEBI ID4728
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1213631
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in 3',5'-cyclic-AMP phosphodiesterase activity
Specific function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May have a role in muscle signal transduction.
Gene Name:
PDE7A
Uniprot ID:
Q13946
Molecular weight:
55504.475
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents.
Gene Name:
PDE4B
Uniprot ID:
Q07343
Molecular weight:
64351.765
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [PubMed:225216 ]
  4. Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [PubMed:7925603 ]
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in the control of cAMP-mediated neural activity and cAMP metabolism in the brain.
Gene Name:
PDE7B
Uniprot ID:
Q9NP56
Molecular weight:
51834.855
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:
PDE4C
Uniprot ID:
Q08493
Molecular weight:
79900.795
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [PubMed:225216 ]
  4. Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [PubMed:7925603 ]
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:
PDE4D
Uniprot ID:
Q08499
Molecular weight:
91114.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [PubMed:7925603 ]
General function:
Involved in 3',5'-cyclic-nucleotide phosphodiesterase activity
Specific function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:
PDE4A
Uniprot ID:
P27815
Molecular weight:
98142.155
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  4. Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [PubMed:225216 ]
  5. Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [PubMed:7925603 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
ADORA1
Uniprot ID:
P30542
Molecular weight:
36511.3
References
  1. Schwabe U, Ukena D, Lohse MJ: Xanthine derivatives as antagonists at A1 and A2 adenosine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1985 Sep;330(3):212-21. [PubMed:2997628 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:
ADORA2A
Uniprot ID:
P29274
Molecular weight:
44706.9
References
  1. Schwabe U, Ukena D, Lohse MJ: Xanthine derivatives as antagonists at A1 and A2 adenosine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1985 Sep;330(3):212-21. [PubMed:2997628 ]