NP-MRD: Showing NP-Card for Glenthol A (NP0333203)

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Record Information

Version

2.0

Created at

2024-05-12 13:41:28 UTC

Updated at

2024-09-03 04:21:34 UTC

NP-MRD ID

NP0333203

Natural Product DOI

https://doi.org/10.57994/2528

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glenthol A

Description

Glenthol A belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Glenthol A was first documented in 2021 (PMID: 34652159). Based on a literature review very few articles have been published on Glenthol A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01242316172D          

 22 24  0  0  1  0            999 V2000
    5.5756   -0.3478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3468    0.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9188    1.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6900    1.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8892    2.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3171    1.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5460    0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9739    0.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1731    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9443    1.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3722    0.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5714    0.6430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9993    0.0485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1985    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3735   -0.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0303    1.0393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3426    1.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9146    2.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7154    1.8320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6858    2.8228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5163    1.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2027   -0.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 18 20  2  0  0  0  0
 10 21  1  0  0  0  0
  6 21  1  0  0  0  0
  8 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333203

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1CC(=O)OC2(C1)CC(=O)C1=C(C2)C=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-9(17)21-11-5-14(20)22-16(7-11)6-10-3-2-4-12(18)15(10)13(19)8-16/h2-4,11,18H,5-8H2,1H3/t11-,16?/m1/s1

> <INCHI_KEY>
RYUNJDVLZRCLLD-ZVDHGWRTSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.298

> <EXACT_MASS>
304.094688235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.05060271181434

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4'S)-5-hydroxy-4,6'-dioxo-3,4-dihydro-1H-spiro[naphthalene-2,2'-oxan]-4'-yl acetate

> <JCHEM_LOGP>
1.5707343699999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.537954766662558

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.660035232256778

> <JCHEM_PKA_STRONGEST_BASIC>
-5.60429911243226

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
74.98389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4'S)-5-hydroxy-4,6'-dioxo-1,3-dihydrospiro[naphthalene-2,2'-oxan]-4'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JAN-23         0                                  
HETATM    1  O   UNK     0      10.408  -0.649   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.981   0.830   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.049   1.940   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.621   3.420   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.126   3.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.059   2.680   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.486   1.200   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.418   0.091   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.923   0.461   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.496   1.940   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.428   0.830   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.933   1.200   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.865   0.091   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.371   0.461   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.697  -0.649   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.057   1.940   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.506   2.680   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.574   3.790   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.069   3.420   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.147   5.269   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.564   3.050   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.845  -1.389   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19   21                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   10                                                       
CONECT   20   18                                                            
CONECT   21   10    6                                                       
CONECT   22    8                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₆

Average Mass

304.2980 Da

Monoisotopic Mass

304.09469 Da

IUPAC Name

(4'S)-5-hydroxy-4,6'-dioxo-3,4-dihydro-1H-spiro[naphthalene-2,2'-oxan]-4'-yl acetate

Traditional Name

(4'S)-5-hydroxy-4,6'-dioxo-1,3-dihydrospiro[naphthalene-2,2'-oxan]-4'-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1CC(=O)OC2(C1)CC(=O)C1=C(C2)C=CC=C1O

InChI Identifier

InChI=1S/C16H16O6/c1-9(17)21-11-5-14(20)22-16(7-11)6-10-3-2-4-12(18)15(10)13(19)8-16/h2-4,11,18H,5-8H2,1H3/t11-,16?/m1/s1

InChI Key

RYUNJDVLZRCLLD-ZVDHGWRTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C6D6, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2024-05-12	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces sp. CMB-PB042		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohol esters

Direct Parent

Fatty alcohol esters

Alternative Parents

Substituents

Fatty alcohol ester
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Delta_valerolactone
Fatty acid ester
Delta valerolactone
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Oxane
Dicarboxylic acid or derivatives
Beta-hydroxy ketone
Vinylogous acid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
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	1.57	ChemAxon
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.98 m³·mol⁻¹	ChemAxon
Polarizability	30.05 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1021/acs.orglett.1c02954

Showing NP-Card for Glenthol A (NP0333203)

MOL for NP0333203 (Glenthol A)

3D MOL for NP0333203 (Glenthol A)

3D SDF for NP0333203 (Glenthol A)

3D-SDF for NP0333203 (Glenthol A)

PDB for NP0333203 (Glenthol A)

3D PDB for NP0333203 (Glenthol A)

SMILES for NP0333203 (Glenthol A)

INCHI for NP0333203 (Glenthol A)

Structure for NP0333203 (Glenthol A)

3D Structure for NP0333203 (Glenthol A)