NP-MRD: Showing NP-Card for Clavilactone K (NP0333178)

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Record Information

Version

2.0

Created at

2024-05-12 03:52:57 UTC

Updated at

2026-02-18 13:03:14 UTC

NP-MRD ID

NP0333178

Natural Product DOI

https://doi.org/10.57994/2503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Clavilactone K

Description

Clavilactone K belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Clavilactone K was first documented in 2022 (PMID: 35803523). Based on a literature review very few articles have been published on Clavilactone K.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01242306292D          

 27 30  0  0  1  0            999 V2000
    4.7504    0.4013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3021   -0.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777   -1.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5016   -1.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2294   -1.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782   -0.2493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1025    0.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2786    0.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303   -0.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9030    1.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1332    0.9649    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3456    1.7621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3094    0.9205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5056    1.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0126    1.6903    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6530    2.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086    3.0343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    1.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3069    2.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868    3.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2351    4.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9896    3.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198    3.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2285    2.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1752    1.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6235    2.6049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5508    1.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  1  0  0  0
 13 11  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
  7 27  1  0  0  0  0
M  END


  Mrv2104 01242306292D          

 27 30  0  0  1  0            999 V2000
    4.7504    0.4013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3021   -0.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777   -1.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5016   -1.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2294   -1.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4782   -0.2493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1025    0.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2786    0.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303   -0.1654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9030    1.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1332    0.9649    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3456    1.7621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3094    0.9205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5056    1.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0126    1.6903    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6530    2.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086    3.0343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    1.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3069    2.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868    3.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2351    4.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9896    3.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198    3.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2285    2.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1752    1.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6235    2.6049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5508    1.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  1  0  0  0
 13 11  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
  7 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333178

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)NC1=C(O)C2=C(C\C(C)=C/CC[C@@]34O[C@@H]3[C@@H]2OC4=O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO6/c1-9(2)18(24)21-12-8-13(22)11-7-10(3)5-4-6-20-17(27-20)16(26-19(20)25)14(11)15(12)23/h5,8-9,16-17,22-23H,4,6-7H2,1-3H3,(H,21,24)/b10-5-/t16-,17-,20-/m1/s1

> <INCHI_KEY>
VQOIHQFCIVFBEC-IQPAJRPASA-N

> <FORMULA>
C20H23NO6

> <MOLECULAR_WEIGHT>
373.405

> <EXACT_MASS>
373.152537465

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.18011248399564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(1R,4Z,13R,14R)-8,11-dihydroxy-5-methyl-16-oxo-15,17-dioxatetracyclo[11.2.2.0^{1,14}.0^{7,12}]heptadeca-4,7(12),8,10-tetraen-10-yl]-2-methylpropanamide

> <JCHEM_LOGP>
3.1110030196666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.67696483869976

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.619830719733763

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6817542109511376

> <JCHEM_POLAR_SURFACE_AREA>
108.39

> <JCHEM_REFRACTIVITY>
98.7296

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1R,4Z,13R,14R)-8,11-dihydroxy-5-methyl-16-oxo-15,17-dioxatetracyclo[11.2.2.0^{1,14}.0^{7,12}]heptadeca-4,7(12),8,10-tetraen-10-yl]-2-methylpropanamide

> <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       8.867   0.749   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.031  -0.544   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.732  -1.915   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.270  -1.993   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.895  -3.208   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       6.493  -0.465   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.791   0.906   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.253   0.984   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.417  -0.309   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.552   2.355   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.115   1.801   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.512   3.289   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.578   1.718   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.944   1.957   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.024   3.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.219   4.126   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.136   5.664   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.389   3.648   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.306   5.186   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.335   6.381   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.172   7.674   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.847   6.778   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.410   6.224   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.427   4.931   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.927   3.570   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.764   4.862   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.628   2.199   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   16                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   13   14   16   24                                             
CONECT   16   15   12   17                                                  
CONECT   17   16                                                            
CONECT   18   10   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   15                                                       
CONECT   25   18   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    7                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₃NO₆

Average Mass

373.4050 Da

Monoisotopic Mass

373.15254 Da

IUPAC Name

N-[(1R,4Z,13R,14R)-8,11-dihydroxy-5-methyl-16-oxo-15,17-dioxatetracyclo[11.2.2.0^{1,14}.0^{7,12}]heptadeca-4,7(12),8,10-tetraen-10-yl]-2-methylpropanamide

Traditional Name

N-[(1R,4Z,13R,14R)-8,11-dihydroxy-5-methyl-16-oxo-15,17-dioxatetracyclo[11.2.2.0^{1,14}.0^{7,12}]heptadeca-4,7(12),8,10-tetraen-10-yl]-2-methylpropanamide

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)NC1=C(O)C2=C(C\C(C)=C/CC[C@@]34O[C@@H]3[C@@H]2OC4=O)C(O)=C1

InChI Identifier

InChI=1S/C20H23NO6/c1-9(2)18(24)21-12-8-13(22)11-7-10(3)5-4-6-20-17(27-20)16(26-19(20)25)14(11)15(12)23/h5,8-9,16-17,22-23H,4,6-7H2,1-3H3,(H,21,24)/b10-5-/t16-,17-,20-/m1/s1

InChI Key

VQOIHQFCIVFBEC-IQPAJRPASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	[email protected]	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, 600.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-18	View Spectrum
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
Clitocybe clavipes		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Monoterpenoid
Aromatic monoterpenoid
N-arylamide
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Fatty acyl
Benzenoid
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Monosaccharide
Gamma butyrolactone
Para-dioxane
Tetrahydrofuran
Lactone
Carboxylic acid ester
Carboxamide group
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	3.11	ChemAxon
pKa (Strongest Acidic)	8.62	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.39 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.73 m³·mol⁻¹	ChemAxon
Polarizability	38.18 Å³	ChemAxon
Number of Rings	4	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

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 K (NP0333178)

MOL for NP0333178 (Clavilactone K)

3D MOL for NP0333178 (Clavilactone K)

3D SDF for NP0333178 (Clavilactone K)

3D-SDF for NP0333178 (Clavilactone K)

PDB for NP0333178 (Clavilactone K)

3D PDB for NP0333178 (Clavilactone K)

SMILES for NP0333178 (Clavilactone K)

INCHI for NP0333178 (Clavilactone K)

Structure for NP0333178 (Clavilactone K)

3D Structure for NP0333178 (Clavilactone K)