NP-MRD: Showing NP-Card for (+)-S-Myricanol glucoside (NP0138589)

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Record Information

Version

1.0

Created at

2022-06-29 17:36:31 UTC

Updated at

2022-06-29 17:36:32 UTC

NP-MRD ID

NP0138589

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-S-Myricanol glucoside

Description

5-Dodecyldihydro-2(3H)-furanone, also known as 4-dodecyl-g-butyrolactone or 4-hexadecanolide, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. 5-Dodecyldihydro-2(3H)-furanone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-Dodecyldihydro-2(3H)-furanone has been detected, but not quantified in, a few different foods, such as fruits, parsnips, and root vegetables. (+)-S-Myricanol glucoside is found in Morella nana and Morella rubra. This could make 5-dodecyldihydro-2(3H)-furanone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061311022D          

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M  END

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 17 18  1  0  0  0  0
 17 22  2  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 26 27  1  0  0  0  0
 26 31  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 32  1  0  0  0  0
 29 30  1  0  0  0  0
 29 34  1  0  0  0  0
 30 31  1  0  0  0  0
 30 35  1  0  0  0  0
 31 36  1  0  0  0  0
 32 33  1  0  0  0  0
  4 37  1  0  0  0  0
  3 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138589

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC2OC(CO)C(O)C(O)C2O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(O)CCCC2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O10/c1-34-25-18-12-15(5-3-4-6-16(29)9-7-14-8-10-19(30)17(18)11-14)24(26(25)35-2)37-27-23(33)22(32)21(31)20(13-28)36-27/h8,10-12,16,20-23,27-33H,3-7,9,13H2,1-2H3

> <INCHI_KEY>
NPSYWDNXSMBWKP-UHFFFAOYSA-N

> <FORMULA>
C27H36O10

> <MOLECULAR_WEIGHT>
520.5687

> <EXACT_MASS>
520.230847372

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
54.010294522526806

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-({11,17-dihydroxy-3,4-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-5-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.8291715840000005

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.201138159783833

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.790824635091658

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6891361697500304

> <JCHEM_POLAR_SURFACE_AREA>
158.3

> <JCHEM_REFRACTIVITY>
133.18149999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-({11,17-dihydroxy-3,4-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-5-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

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  O   UNK     0      -6.548   1.088   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.981  -1.911   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.369  -1.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.309   1.557   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.446   2.916   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.803   5.324   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.704   4.075   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.074   2.671   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.975   1.422   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.507   1.578   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.138   2.983   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.236   4.232   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.867   5.637   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.399   5.794   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.670   3.140   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -6.301   4.545   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.083  -1.055   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.055   0.139   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.576  -0.106   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.123  -1.545   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.151  -2.739   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.630  -2.494   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.658  -3.688   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.137  -3.443   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.229  -1.009   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.433   6.729   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.965   6.886   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.596   8.291   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.694   9.539   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.162   9.383   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.532   7.978   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.128   8.447   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.758   9.852   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -3.325  10.944   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -0.261  10.631   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.000   7.821   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.251   0.252   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2    3   24   25                                                  
CONECT    3    2   37                                                       
CONECT    4    5   37                                                       
CONECT    5    4    8                                                       
CONECT    6    7   26                                                       
CONECT    7    6    8   12                                                  
CONECT    8    5    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   15                                                  
CONECT   12    7   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   11   16                                                       
CONECT   16   15                                                            
CONECT   17   18   22                                                       
CONECT   18   10   17   19                                                  
CONECT   19    1   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   17   21   23                                                  
CONECT   23   22   24                                                       
CONECT   24    2   23                                                       
CONECT   25    2                                                            
CONECT   26    6   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31   35                                                  
CONECT   31   26   30   36                                                  
CONECT   32   28   33                                                       
CONECT   33   32                                                            
CONECT   34   29                                                            
CONECT   35   30                                                            
CONECT   36   31                                                            
CONECT   37    4    3                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
2(3H)-Furanone, 5-dodecyldihydro- (9ci)	HMDB
4-Dodecyl-g-butyrolactone	HMDB
4-Hexadecanolide	HMDB
g-Palmitolactone	HMDB
gamma-Hydroxypalmitic acid lactone	HMDB
gamma-Palmitolactone	HMDB
Hexadeca-1,4-lactone	HMDB
Hexadecanoic acid, 4-hydroxy-, gamma-lactone (8ci)	HMDB
Hexadecanoic acid, 4-hydroxy-, laquo gammaraquo -lactone	HMDB
Laquo gammaraquo -hexadecalactone	HMDB
Laquo gammaraquo -palmitolactone	HMDB
Palmito-laquo gammaraquo -lactone	HMDB
Myricanol glucoside	HMDB
Myricanol-15-glucoside	HMDB

Chemical Formula

C₂₇H₃₆O₁₀

Average Mass

520.5687 Da

Monoisotopic Mass

520.23085 Da

IUPAC Name

2-({11,17-dihydroxy-3,4-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-5-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-({11,17-dihydroxy-3,4-dimethoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2,4,6(19),14(18),15-hexaen-5-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

449729-89-9

SMILES

COC1=C(OC2OC(CO)C(O)C(O)C2O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(O)CCCC2)=C1

InChI Identifier

InChI=1S/C27H36O10/c1-34-25-18-12-15(5-3-4-6-16(29)9-7-14-8-10-19(30)17(18)11-14)24(26(25)35-2)37-27-23(33)22(32)21(31)20(13-28)36-27/h8,10-12,16,20-23,27-33H,3-7,9,13H2,1-2H3

InChI Key

NPSYWDNXSMBWKP-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Morella nana	LOTUS Database	35616633
Morella rubra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	1.42	ALOGPS
logP	1.83	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.79	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	158.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	133.18 m³·mol⁻¹	ChemAxon
Polarizability	54.01 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	No	ChemAxon

External Links

HMDB ID

HMDB0031145

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003157

KNApSAcK ID

Not Available

Chemspider ID

88223

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

97747

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-S-Myricanol glucoside (NP0138589)

MOL for NP0138589 ((+)-S-Myricanol glucoside)

3D MOL for NP0138589 ((+)-S-Myricanol glucoside)

3D SDF for NP0138589 ((+)-S-Myricanol glucoside)

3D-SDF for NP0138589 ((+)-S-Myricanol glucoside)

PDB for NP0138589 ((+)-S-Myricanol glucoside)

3D PDB for NP0138589 ((+)-S-Myricanol glucoside)

SMILES for NP0138589 ((+)-S-Myricanol glucoside)

INCHI for NP0138589 ((+)-S-Myricanol glucoside)

Structure for NP0138589 ((+)-S-Myricanol glucoside)

3D Structure for NP0138589 ((+)-S-Myricanol glucoside)