NP-MRD: Showing NP-Card for 7-Butyl-6,8-dihydroxy-3(R)-pent-9,11-dienylisochroman-1-one (NP0333157)

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Record Information

Version

1.0

Created at

2024-05-11 19:25:33 UTC

Updated at

2024-05-11 19:51:18 UTC

NP-MRD ID

NP0333157

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-Butyl-6,8-dihydroxy-3(R)-pent-9,11-dienylisochroman-1-one

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232322022D          

 22 23  0  0  0  0            999 V2000
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  9 20  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333157

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC1=C(O)C=C2CC(OC(=O)C2=C1O)\C=C\C=C\C

> <INCHI_IDENTIFIER>
InChI=1/C18H22O4/c1-3-5-7-8-13-10-12-11-15(19)14(9-6-4-2)17(20)16(12)18(21)22-13/h3,5,7-8,11,13,19-20H,4,6,9-10H2,1-2H3/b5-3+,8-7+

> <INCHI_KEY>
BOLVLKQIZCZQPH-VSAQMIDANA-N

> <FORMULA>
C18H22O4

> <MOLECULAR_WEIGHT>
302.37

> <EXACT_MASS>
302.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
34.602438880975775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-butyl-6,8-dihydroxy-3-[(1E,3E)-penta-1,3-dien-1-yl]-3,4-dihydro-1H-2-benzopyran-1-one

> <JCHEM_LOGP>
5.411475588666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.61455999850698

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.860372820880768

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9984838568777987

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
89.02389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
7-butyl-6,8-dihydroxy-3-[(1E,3E)-penta-1,3-dien-1-yl]-3,4-dihydro-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JAN-23         0                                  
HETATM    1  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   11   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20    9   18   21                                                  
CONECT   21   20    5   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₂O₄

Average Mass

302.3700 Da

Monoisotopic Mass

302.15181 Da

IUPAC Name

7-butyl-6,8-dihydroxy-3-[(1E,3E)-penta-1,3-dien-1-yl]-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

7-butyl-6,8-dihydroxy-3-[(1E,3E)-penta-1,3-dien-1-yl]-3,4-dihydro-2-benzopyran-1-one

CAS Registry Number

Not Available

SMILES

CCCCC1=C(O)C=C2CC(OC(=O)C2=C1O)\C=C\C=C\C

InChI Identifier

InChI=1/C18H22O4/c1-3-5-7-8-13-10-12-11-15(19)14(9-6-4-2)17(20)16(12)18(21)22-13/h3,5,7-8,11,13,19-20H,4,6,9-10H2,1-2H3/b5-3+,8-7+

InChI Key

BOLVLKQIZCZQPH-VSAQMIDANA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3CN, experimental)	s_kali03@wwu.de	Not Available	Not Available	2024-05-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3CN, experimental)	s_kali03@wwu.de	Not Available	Not Available	2024-05-11	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3CN, experimental)	s_kali03@wwu.de	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3CN, experimental)	s_kali03@wwu.de	Not Available	Not Available	2024-05-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3CN, experimental)	s_kali03@wwu.de	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
mangiferae		Not Available

Chemical Taxonomy

Classification

Not classified

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	5.41	ChemAxon
pKa (Strongest Acidic)	8.86	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	89.02 m³·mol⁻¹	ChemAxon
Polarizability	34.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Atanasoff-Kardjalieff AK, Seidl B, Steinert K, Daniliuc CG, Schuhmacher R, Humpf HU, Kalinina S, Studt-Reinhold L: Biosynthesis of the Isocoumarin Derivatives Fusamarins is Mediated by the PKS8 Gene Cluster in Fusarium. Chembiochem. 2023 Mar 14;24(6):e202200342. doi: 10.1002/cbic.202200342. Epub 2022 Oct 18. [PubMed:36137261 ]

Showing NP-Card for 7-Butyl-6,8-dihydroxy-3(R)-pent-9,11-dienylisochroman-1-one (NP0333157)

MOL for NP0333157 (7-Butyl-6,8-dihydroxy-3(R)-pent-9,11-dienylisochroman-1-one)

3D MOL for NP0333157 (7-Butyl-6,8-dihydroxy-3(R)-pent-9,11-dienylisochroman-1-one)

3D SDF for NP0333157 (7-Butyl-6,8-dihydroxy-3(R)-pent-9,11-dienylisochroman-1-one)

3D-SDF for NP0333157 (7-Butyl-6,8-dihydroxy-3(R)-pent-9,11-dienylisochroman-1-one)

PDB for NP0333157 (7-Butyl-6,8-dihydroxy-3(R)-pent-9,11-dienylisochroman-1-one)

3D PDB for NP0333157 (7-Butyl-6,8-dihydroxy-3(R)-pent-9,11-dienylisochroman-1-one)

SMILES for NP0333157 (7-Butyl-6,8-dihydroxy-3(R)-pent-9,11-dienylisochroman-1-one)

INCHI for NP0333157 (7-Butyl-6,8-dihydroxy-3(R)-pent-9,11-dienylisochroman-1-one)

Structure for NP0333157 (7-Butyl-6,8-dihydroxy-3(R)-pent-9,11-dienylisochroman-1-one)

3D Structure for NP0333157 (7-Butyl-6,8-dihydroxy-3(R)-pent-9,11-dienylisochroman-1-one)