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Showing NP-Card for Heliannuol D (NP0048161)

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Record Information
Version2.0
Created at2022-03-17 20:52:05 UTC
Updated at2022-03-17 20:52:05 UTC
NP-MRD IDNP0048161
Secondary Accession NumbersNone
Natural Product Identification
Common NameHeliannuol D
DescriptionHeliannuol D, also known as THDU, belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom). Heliannuol D is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Heliannuol D has been detected, but not quantified in, fats and oils and sunflowers. Heliannuol D is found in Helianthus annuus and Helianthus annuus L.cv.Peredovick . This could make heliannuol D a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048161 (Heliannuol D)


  Mrv0541 05061308152D          

 18 19  0  0  0  0            999 V2000
    2.3821    0.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    2.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3987    3.9775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    3.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    1.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7279    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    2.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    1.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    1.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    2.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8843    3.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    1.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5293    2.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    2.8710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  1  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15 14  1  0  0  0  0
 16 12  1  0  0  0  0
 17 15  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
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3D MOL for NP0048161 (Heliannuol D)

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3D SDF for NP0048161 (Heliannuol D)

  Mrv0541 05061308152D          

 18 19  0  0  0  0            999 V2000
    2.3821    0.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    2.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3987    3.9775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    3.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    1.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7279    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    2.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    1.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    1.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    2.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8843    3.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    1.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5293    2.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    2.8710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  1  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15 14  1  0  0  0  0
 16 12  1  0  0  0  0
 17 15  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048161

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-9-5-6-14(15(3,4)17)18-13-7-10(2)12(16)8-11(9)13/h7-9,14,16-17H,5-6H2,1-4H3

> <INCHI_KEY>
BIIJJHXLFCDTIZ-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.345062523177376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-hydroxypropan-2-yl)-5,8-dimethyl-2,3,4,5-tetrahydro-1-benzoxepin-7-ol

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.3082923016666665

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.308343663872293

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.337484152401386

> <JCHEM_PKA_STRONGEST_BASIC>
-3.101350820629431

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
71.623

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-hydroxypropan-2-yl)-5,8-dimethyl-2,3,4,5-tetrahydro-1-benzoxepin-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0048161 (Heliannuol D)
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PDB for NP0048161 (Heliannuol D)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.447   0.398   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.416   5.169   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.211   7.425   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.047   7.181   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.291   2.241   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.959   3.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.252   5.169   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.252   2.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.789   1.899   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.918   4.399   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.585   2.859   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.918   2.859   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.585   4.399   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.291   5.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.251   6.221   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.416   2.089   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.455   5.260   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.789   5.359   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5    6    9                                                       
CONECT    6    5   14                                                       
CONECT    7   10   13                                                       
CONECT    8   11   12                                                       
CONECT    9    1    5   11                                                  
CONECT   10    2    7   12                                                  
CONECT   11    8    9   13                                                  
CONECT   12    8   10   16                                                  
CONECT   13    7   11   18                                                  
CONECT   14    6   15   18                                                  
CONECT   15    3    4   14   17                                             
CONECT   16   12                                                            
CONECT   17   15                                                            
CONECT   18   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

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3D PDB for NP0048161 (Heliannuol D)
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SMILES for NP0048161 (Heliannuol D)
CC1CCC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O
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INCHI for NP0048161 (Heliannuol D)
InChI=1S/C15H22O3/c1-9-5-6-14(15(3,4)17)18-13-7-10(2)12(16)8-11(9)13/h7-9,14,16-17H,5-6H2,1-4H3
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View in JSmol
Synonyms
ValueSource
(+)-Heliannuol DHMDB
2'-DeoxytetrahydrouridineHMDB
3,4,5,6-TetrahydrodeoxyuridineHMDB
5,10-Epoxy-1,3,5-bisabolatriene-2,11-diolHMDB
Tetrahydro-2'-deoxyuridineHMDB
THDUHMDB
Heliannuol DMeSH
Chemical FormulaC15H22O3
Average Mass250.3334 Da
Monoisotopic Mass250.15689 Da
IUPAC Name2-(2-hydroxypropan-2-yl)-5,8-dimethyl-2,3,4,5-tetrahydro-1-benzoxepin-7-ol
Traditional Name2-(2-hydroxypropan-2-yl)-5,8-dimethyl-2,3,4,5-tetrahydro-1-benzoxepin-7-ol
CAS Registry Number161730-09-2
SMILES
CC1CCC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O
InChI Identifier
InChI=1S/C15H22O3/c1-9-5-6-14(15(3,4)17)18-13-7-10(2)12(16)8-11(9)13/h7-9,14,16-17H,5-6H2,1-4H3
InChI KeyBIIJJHXLFCDTIZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Helianthus annuusLOTUS Database
Helianthus annuus L.FooDB
Helianthus annuus L.cv.PeredovickPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom).
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzoxepines  
Sub ClassNot Available
Direct ParentBenzoxepines  
Alternative Parents
Substituents
  • Benzoxepine
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Tertiary alcohol
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.1ALOGPS
logP3.31ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)10.34ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.62 m³·mol⁻¹ChemAxon
Polarizability28.35 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035137  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013773  
KNApSAcK IDC00037241  
Chemspider ID9600106  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11425230  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available