NP-MRD: Showing NP-Card for Clavilactone J (NP0333177)

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Record Information

Version

2.0

Created at

2024-05-12 03:48:24 UTC

Updated at

2024-09-03 04:21:29 UTC

NP-MRD ID

NP0333177

Natural Product DOI

https://doi.org/10.57994/2502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Clavilactone J

Description

Clavilactone J belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Clavilactone J was first documented in 2022 (PMID: 35803523). Based on a literature review very few articles have been published on Clavilactone J.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01242306242D          

 22 26  0  0  1  0            999 V2000
    4.1124    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327    0.1007    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5768    0.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028    0.8802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428    0.2566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0829   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -1.3025    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4627   -0.6789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1926   -1.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -0.8348    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7255   -1.6904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5050   -1.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7448   -2.7499    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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  1  0  0  0
 16 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19  7  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333177

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CC3=C([C@H]4OC(=O)[C@]5(CC[C@@H]1O2)O[C@H]45)C(O)=CC=C3O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-15-6-7-8(17)2-3-9(18)11(7)12-13-16(22-13,14(19)20-12)5-4-10(15)21-15/h2-3,10,12-13,17-18H,4-6H2,1H3/t10-,12+,13+,15+,16+/m0/s1

> <INCHI_KEY>
DXMADUIHYYUTNU-POGFSQCLSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.298

> <EXACT_MASS>
304.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.918982750515063

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,6R,14R,15R)-9,12-dihydroxy-6-methyl-5,16,18-trioxapentacyclo[12.2.2.0^{1,15}.0^{4,6}.0^{8,13}]octadeca-8(13),9,11-trien-17-one

> <JCHEM_LOGP>
1.7289890186666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.359898675391996

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.417750803210371

> <JCHEM_PKA_STRONGEST_BASIC>
-3.971181070464122

> <JCHEM_POLAR_SURFACE_AREA>
91.82

> <JCHEM_REFRACTIVITY>
73.4257

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,6R,14R,15R)-9,12-dihydroxy-6-methyl-5,16,18-trioxapentacyclo[12.2.2.0^{1,15}.0^{4,6}.0^{8,13}]octadeca-8(13),9,11-trien-17-one

> <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       7.677   3.680   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.172   2.225   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.660   1.934   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.156   0.479   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.164  -0.685   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.660  -2.140   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.677  -0.394   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.181   1.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.693   1.352   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.701   0.188   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.410   1.700   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.205   1.643   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.213   0.479   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.221  -0.685   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.717  -2.140   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.205  -2.431   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.197  -1.267   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.693  -2.722   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.685  -1.558   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.821  -3.155   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.276  -3.660   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.724  -5.133   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   19                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   10   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   21                                             
CONECT   17   16   18   19                                                  
CONECT   18   17   16                                                       
CONECT   19   17    7   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₆

Average Mass

304.2980 Da

Monoisotopic Mass

304.09469 Da

IUPAC Name

(1R,4S,6R,14R,15R)-9,12-dihydroxy-6-methyl-5,16,18-trioxapentacyclo[12.2.2.0^{1,15}.0^{4,6}.0^{8,13}]octadeca-8(13),9,11-trien-17-one

Traditional Name

(1R,4S,6R,14R,15R)-9,12-dihydroxy-6-methyl-5,16,18-trioxapentacyclo[12.2.2.0^{1,15}.0^{4,6}.0^{8,13}]octadeca-8(13),9,11-trien-17-one

CAS Registry Number

Not Available

SMILES

C[C@@]12CC3=C([C@H]4OC(=O)[C@]5(CC[C@@H]1O2)O[C@H]45)C(O)=CC=C3O

InChI Identifier

InChI=1S/C16H16O6/c1-15-6-7-8(17)2-3-9(18)11(7)12-13-16(22-13,14(19)20-12)5-4-10(15)21-15/h2-3,10,12-13,17-18H,4-6H2,1H3/t10-,12+,13+,15+,16+/m0/s1

InChI Key

DXMADUIHYYUTNU-POGFSQCLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	mgxfl8785@163.com	Not Available	Not Available	2024-05-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	mgxfl8785@163.com	Not Available	Not Available	2024-05-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	mgxfl8785@163.com	Not Available	Not Available	2024-05-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	mgxfl8785@163.com	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	mgxfl8785@163.com	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	mgxfl8785@163.com	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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, simulated)	Not Available	Not Available	Not Available	2024-05-12	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Clitocybe clavipes		Not Available

Chemical Taxonomy

Description

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
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Benzenoid
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Monosaccharide
Gamma butyrolactone
Para-dioxane
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
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	1.73	ChemAxon
pKa (Strongest Acidic)	9.42	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.82 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.43 m³·mol⁻¹	ChemAxon
Polarizability	28.92 Å³	ChemAxon
Number of Rings	5	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

170988446

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hou Y, Li Q, Chen M, Wu H, Yang J, Sun Z, Xu X, Ma G: Novel geranylhydroquinone derived meroterpenoids from the fungus Clitocybe clavipes and their cytotoxic activity. Fitoterapia. 2022 Sep;161:105251. doi: 10.1016/j.fitote.2022.105251. Epub 2022 Jul 6. [PubMed:35803523 ]
DOI: 10.1016/j.fitote.2022.105251
PII: s0367326x22001290

Showing NP-Card for Clavilactone J (NP0333177)

MOL for NP0333177 (Clavilactone J)

3D MOL for NP0333177 (Clavilactone J)

3D SDF for NP0333177 (Clavilactone J)

3D-SDF for NP0333177 (Clavilactone J)

PDB for NP0333177 (Clavilactone J)

3D PDB for NP0333177 (Clavilactone J)

SMILES for NP0333177 (Clavilactone J)

INCHI for NP0333177 (Clavilactone J)

Structure for NP0333177 (Clavilactone J)

3D Structure for NP0333177 (Clavilactone J)