NP-MRD: Showing NP-Card for 6',7'-Dihydroxybergamottin octanal acetal (NP0081519)

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Record Information

Version

2.0

Created at

2022-04-29 02:31:36 UTC

Updated at

2022-04-29 02:31:36 UTC

NP-MRD ID

NP0081519

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6',7'-Dihydroxybergamottin octanal acetal

Description

4-{[(2E)-5-[(2S,4S)-2-heptyl-5,5-dimethyl-1,3-dioxolan-4-yl]-3-methylpent-2-en-1-yl]oxy}-2H,3H,7H-furo[3,2-g]chromen-7-one belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. 6',7'-Dihydroxybergamottin octanal acetal is found in Citrus paradisi . Based on a literature review very few articles have been published on 4-{[(2E)-5-[(2S,4S)-2-heptyl-5,5-dimethyl-1,3-dioxolan-4-yl]-3-methylpent-2-en-1-yl]oxy}-2H,3H,7H-furo[3,2-g]chromen-7-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


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 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 13 30  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  1 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081519

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC[C@H]1O[C@@H](CC\C(C)=C\COC2=C3C=CC(=O)OC3=CC3=C2CCO3)C(C)(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O6/c1-5-6-7-8-9-10-27-34-25(29(3,4)35-27)13-11-20(2)15-17-32-28-21-12-14-26(30)33-24(21)19-23-22(28)16-18-31-23/h12,14-15,19,25,27H,5-11,13,16-18H2,1-4H3/b20-15+/t25-,27-/m0/s1

> <INCHI_KEY>
WJIIDSSFVWOLIZ-JZACSLLISA-N

> <FORMULA>
C29H40O6

> <MOLECULAR_WEIGHT>
484.633

> <EXACT_MASS>
484.282489008

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.82134734734639

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[(2E)-5-[(2S,4S)-2-heptyl-5,5-dimethyl-1,3-dioxolan-4-yl]-3-methylpent-2-en-1-yl]oxy}-2H,3H,7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
6.80

> <JCHEM_LOGP>
6.702505487333333

> <ALOGPS_LOGS>
-6.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.949385851695839

> <JCHEM_POLAR_SURFACE_AREA>
63.22

> <JCHEM_REFRACTIVITY>
137.71200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.65e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(2E)-5-[(2S,4S)-2-heptyl-5,5-dimethyl-1,3-dioxolan-4-yl]-3-methylpent-2-en-1-yl]oxy}-2H,3H-furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0     -28.702   6.832   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -27.170   6.671   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -26.265   7.917   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -26.891   9.324   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -28.423   9.484   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -29.328   8.239   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -28.743  10.991   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -27.409  11.761   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -26.265  10.730   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0     -24.733   7.756   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0     -23.828   9.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -22.297   8.841   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -21.670   7.434   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -20.139   7.273   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -19.512   5.866   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -17.981   5.705   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -16.950   6.849   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0     -15.544   6.223   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -15.704   4.691   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -17.211   4.371   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -17.066   2.838   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -18.447   3.453   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -14.210   6.993   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -12.876   6.223   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.542   6.993   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -10.209   6.223   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.875   6.993   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.541   6.223   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.208   6.993   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -22.576   6.188   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -26.544   5.264   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -27.449   4.018   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -28.981   4.179   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -29.886   2.933   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0     -29.607   5.586   0.000  0.00  0.00           O+0
CONECT    1    2    6   35                                                  
CONECT    2    1    3   31                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    3   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   30                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   16   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   13                                                            
CONECT   31    2   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    1                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀O₆

Average Mass

484.6330 Da

Monoisotopic Mass

484.28249 Da

IUPAC Name

4-{[(2E)-5-[(2S,4S)-2-heptyl-5,5-dimethyl-1,3-dioxolan-4-yl]-3-methylpent-2-en-1-yl]oxy}-2H,3H,7H-furo[3,2-g]chromen-7-one

Traditional Name

4-{[(2E)-5-[(2S,4S)-2-heptyl-5,5-dimethyl-1,3-dioxolan-4-yl]-3-methylpent-2-en-1-yl]oxy}-2H,3H-furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CCCCCCC[C@H]1O[C@@H](CC\C(C)=C\COC2=C3C=CC(=O)OC3=CC3=C2CCO3)C(C)(C)O1

InChI Identifier

InChI=1S/C29H40O6/c1-5-6-7-8-9-10-27-34-25(29(3,4)35-27)13-11-20(2)15-17-32-28-21-12-14-26(30)33-24(21)19-23-22(28)16-18-31-23/h12,14-15,19,25,27H,5-11,13,16-18H2,1-4H3/b20-15+/t25-,27-/m0/s1

InChI Key

WJIIDSSFVWOLIZ-JZACSLLISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Citrus paradisi	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

Psoralen
1-benzopyran
Benzopyran
Coumaran
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Meta-dioxolane
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	6.8	ALOGPS
logP	6.7	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	137.71 m³·mol⁻¹	ChemAxon
Polarizability	56.82 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

163106418

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6',7'-Dihydroxybergamottin octanal acetal (NP0081519)

MOL for NP0081519 (6',7'-Dihydroxybergamottin octanal acetal)

3D MOL for NP0081519 (6',7'-Dihydroxybergamottin octanal acetal)

3D SDF for NP0081519 (6',7'-Dihydroxybergamottin octanal acetal)

3D-SDF for NP0081519 (6',7'-Dihydroxybergamottin octanal acetal)

PDB for NP0081519 (6',7'-Dihydroxybergamottin octanal acetal)

3D PDB for NP0081519 (6',7'-Dihydroxybergamottin octanal acetal)

SMILES for NP0081519 (6',7'-Dihydroxybergamottin octanal acetal)

INCHI for NP0081519 (6',7'-Dihydroxybergamottin octanal acetal)

Structure for NP0081519 (6',7'-Dihydroxybergamottin octanal acetal)

3D Structure for NP0081519 (6',7'-Dihydroxybergamottin octanal acetal)