NP-MRD: Showing NP-Card for Jasmolactone D (NP0057664)

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Record Information

Version

2.0

Created at

2022-04-28 03:03:53 UTC

Updated at

2022-04-28 03:03:54 UTC

NP-MRD ID

NP0057664

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Jasmolactone D

Description

Jasmolactone B belongs to the class of organic compounds known as tyrosols and derivatives. Tyrosols and derivatives are compounds containing a hydroxyethyl group attached to the C4 carbon of a phenol group. Jasmolactone D is found in Jasminum multiflorum . Based on a literature review very few articles have been published on Jasmolactone B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205032D          

 37 40  0  0  1  0            999 V2000
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   -0.8374   -0.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1230   -1.6408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5915   -1.2283    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5915   -0.4033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2365    0.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408   -0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552    0.5725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988   -0.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408   -1.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282205032D          

 37 40  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0057664

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1OC=C([C@H]2CC(=O)OC[C@@H](OCCC3=CC(O)=C(O)C=C3)[C@@H]12)C(=O)OCCC1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O11/c27-18-3-1-14(9-20(18)29)5-7-34-22-13-36-23(31)11-16-17(12-37-26(33)24(16)22)25(32)35-8-6-15-2-4-19(28)21(30)10-15/h1-4,9-10,12,16,22,24,26-30,33H,5-8,11,13H2/t16-,22-,24+,26-/m1/s1

> <INCHI_KEY>
GJLGUDQPCIWEPW-MATHTASDSA-N

> <FORMULA>
C26H28O11

> <MOLECULAR_WEIGHT>
516.499

> <EXACT_MASS>
516.163161722

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
51.234880012433486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)ethyl (1R,4aS,9S,9aS)-9-[2-(3,4-dihydroxyphenyl)ethoxy]-1-hydroxy-6-oxo-1H,4aH,5H,6H,8H,9H,9aH-pyrano[3,4-d]oxepine-4-carboxylate

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
2.412590598333333

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.672837671172173

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.05698341136122

> <JCHEM_PKA_STRONGEST_BASIC>
-4.096485583712639

> <JCHEM_POLAR_SURFACE_AREA>
172.20999999999998

> <JCHEM_REFRACTIVITY>
127.83579999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)ethyl (1R,4aS,9S,9aS)-9-[2-(3,4-dihydroxyphenyl)ethoxy]-1-hydroxy-6-oxo-1H,4aH,5H,8H,9H,9aH-pyrano[3,4-d]oxepine-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.230   0.017   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.563  -0.753   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.563  -2.293   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.230  -3.063   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.104  -2.293   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.104  -0.753   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.308   0.207   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.810  -0.135   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.770   1.069   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.478  -1.523   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.810  -2.910   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.308  -3.253   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.965  -4.754   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.094  -5.802   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.752  -7.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.881  -8.351   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.352  -7.897   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.481  -8.944   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.138 -10.446   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.667 -10.900   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.538  -9.852   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.267 -11.493   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.953  -8.490   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.230  -4.603   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.230   1.557   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.104   2.327   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.563   2.327   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.563   3.867   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.897   4.637   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.897   6.177   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.231   6.947   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.231   8.487   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.897   9.257   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.563   8.487   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.563   6.947   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.230   9.257   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.897  10.797   0.000  0.00  0.00           O+0
CONECT    1    2    6   25                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19                                                            
CONECT   23   18                                                            
CONECT   24    4                                                            
CONECT   25    1   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   37                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   30                                                       
CONECT   36   34                                                            
CONECT   37   33                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₁₁

Average Mass

516.4990 Da

Monoisotopic Mass

516.16316 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)ethyl (1R,4aS,9S,9aS)-9-[2-(3,4-dihydroxyphenyl)ethoxy]-1-hydroxy-6-oxo-1H,4aH,5H,6H,8H,9H,9aH-pyrano[3,4-d]oxepine-4-carboxylate

Traditional Name

2-(3,4-dihydroxyphenyl)ethyl (1R,4aS,9S,9aS)-9-[2-(3,4-dihydroxyphenyl)ethoxy]-1-hydroxy-6-oxo-1H,4aH,5H,8H,9H,9aH-pyrano[3,4-d]oxepine-4-carboxylate

CAS Registry Number

Not Available

SMILES

O[C@@H]1OC=C([C@H]2CC(=O)OC[C@@H](OCCC3=CC(O)=C(O)C=C3)[C@@H]12)C(=O)OCCC1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C26H28O11/c27-18-3-1-14(9-20(18)29)5-7-34-22-13-36-23(31)11-16-17(12-37-26(33)24(16)22)25(32)35-8-6-15-2-4-19(28)21(30)10-15/h1-4,9-10,12,16,22,24,26-30,33H,5-8,11,13H2/t16-,22-,24+,26-/m1/s1

InChI Key

GJLGUDQPCIWEPW-MATHTASDSA-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
Jasminum multiflorum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tyrosols and derivatives. Tyrosols and derivatives are compounds containing a hydroxyethyl group attached to the C4 carbon of a phenol group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

Tyrosols and derivatives

Direct Parent

Tyrosols and derivatives

Alternative Parents

Substituents

Tyrosol derivative
Caprolactone
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxepane
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
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	2.2	ALOGPS
logP	2.41	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	127.84 m³·mol⁻¹	ChemAxon
Polarizability	51.23 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

C00010768

Chemspider ID

9224736

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11049569

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Jasmolactone D (NP0057664)

MOL for NP0057664 (Jasmolactone D)

3D MOL for NP0057664 (Jasmolactone D)

3D SDF for NP0057664 (Jasmolactone D)

3D-SDF for NP0057664 (Jasmolactone D)

PDB for NP0057664 (Jasmolactone D)

3D PDB for NP0057664 (Jasmolactone D)

SMILES for NP0057664 (Jasmolactone D)

INCHI for NP0057664 (Jasmolactone D)

Structure for NP0057664 (Jasmolactone D)

3D Structure for NP0057664 (Jasmolactone D)