NP-MRD: Showing NP-Card for 6-Acytyl-N-phe-khamkhain C (NP0351374)

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Record Information

Version

2.0

Created at

2025-07-29 22:02:07 UTC

Updated at

2025-07-31 00:03:51 UTC

NP-MRD ID

NP0351374

Natural Product DOI

https://doi.org/10.57994/4414

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Acytyl-N-phe-khamkhain C

Description

6-Acytyl-N-phe-khamkhain C was first documented in 2025 (PMID: 40669013). Based on a literature review very few articles have been published on 6-Acytyl-N-phe-khamkhain C.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02022315122D          

 34 37  0  0  1  0            999 V2000
    1.1632    2.1984    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9878    2.2242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8124    2.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6439    3.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5785    2.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325    0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5978    1.4972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2079    0.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7732    1.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3386    2.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4626    1.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232    1.1532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2244    0.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1986   -0.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8999   -0.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8741   -1.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5754   -1.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3024   -1.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3281   -0.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6269   -0.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9514    1.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6526    0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772    1.9332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406    0.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373    0.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7286    2.8997    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2940    3.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532    2.9254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9432    3.6524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678    3.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1578    4.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024    2.9770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 14 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 12  1  0  0  0  0
 28 29  1  1  0  0  0
 30 28  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END


  Mrv2104 02022315122D          

 34 37  0  0  1  0            999 V2000
    1.1632    2.1984    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9878    2.2242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8124    2.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6439    3.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5785    2.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325    0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5978    1.4972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2079    0.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7732    1.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3386    2.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4626    1.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232    1.1532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2244    0.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1986   -0.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8999   -0.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8741   -1.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5754   -1.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3024   -1.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3281   -0.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6269   -0.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9514    1.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6526    0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772    1.9332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406    0.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373    0.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7286    2.8997    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2940    3.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532    2.9254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9432    3.6524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678    3.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1578    4.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024    2.9770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 14 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 12  1  0  0  0  0
 28 29  1  1  0  0  0
 30 28  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0351374

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@H](OC(C)=O)[C@H](O)C3=C(C(=O)N(C3)C(CC3=CC=CC=C3)C(O)=O)[C@@]1(C)CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H33NO6/c1-15(28)33-21-20(29)17-14-27(18(24(31)32)13-16-9-6-5-7-10-16)23(30)19(17)26(4)12-8-11-25(2,3)22(21)26/h5-7,9-10,18,20-22,29H,8,11-14H2,1-4H3,(H,31,32)/t18?,20-,21-,22+,26-/m1/s1

> <INCHI_KEY>
KOIFPIZDIMRKTB-PKBPADAASA-N

> <FORMULA>
C26H33NO6

> <MOLECULAR_WEIGHT>
455.551

> <EXACT_MASS>
455.230787787

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.40376930014834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(4R,5S,5aS,9aS)-5-(acetyloxy)-4-hydroxy-6,6,9a-trimethyl-1-oxo-1H,2H,3H,4H,5H,5aH,6H,7H,8H,9H,9aH-cyclohexa[e]isoindol-2-yl]-3-phenylpropanoic acid

> <JCHEM_LOGP>
2.6651222463333326

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.039890356628051

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.881662587324703

> <JCHEM_PKA_STRONGEST_BASIC>
0.4449392822335025

> <JCHEM_POLAR_SURFACE_AREA>
104.14000000000001

> <JCHEM_REFRACTIVITY>
121.27759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(4R,5S,5aS,9aS)-5-(acetyloxy)-4-hydroxy-6,6,9a-trimethyl-1-oxo-3H,4H,5H,5aH,7H,8H,9H-cyclohexa[e]isoindol-2-yl]-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-FEB-23         0                                  
HETATM    1  H   UNK     0       2.171   4.104   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       3.711   4.152   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.250   4.200   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.935   5.707   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.680   4.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.061   2.891   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.333   1.534   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.794   1.486   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.983   2.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.255   1.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.443   2.747   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.632   4.056   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.863   3.689   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -0.977   2.153   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -2.286   1.341   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.237  -0.198   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.546  -1.009   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.498  -2.548   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.807  -3.360   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.164  -2.632   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.212  -1.092   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.904  -0.281   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.643   2.069   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.952   1.258   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.691   3.609   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.449   1.571   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.816   0.075   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.360   5.413   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.549   6.722   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.899   5.461   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.627   6.818   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.167   6.866   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.895   8.223   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.978   5.557   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9   30                                             
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    2   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12   26                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   26                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   15   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   14   11   27                                                  
CONECT   27   26                                                            
CONECT   28   12   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    2   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₃NO₆

Average Mass

455.5510 Da

Monoisotopic Mass

455.23079 Da

IUPAC Name

2-[(4R,5S,5aS,9aS)-5-(acetyloxy)-4-hydroxy-6,6,9a-trimethyl-1-oxo-1H,2H,3H,4H,5H,5aH,6H,7H,8H,9H,9aH-cyclohexa[e]isoindol-2-yl]-3-phenylpropanoic acid

Traditional Name

2-[(4R,5S,5aS,9aS)-5-(acetyloxy)-4-hydroxy-6,6,9a-trimethyl-1-oxo-3H,4H,5H,5aH,7H,8H,9H-cyclohexa[e]isoindol-2-yl]-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12[C@H](OC(C)=O)[C@H](O)C3=C(C(=O)N(C3)C(CC3=CC=CC=C3)C(O)=O)[C@@]1(C)CCCC2(C)C

InChI Identifier

InChI=1S/C26H33NO6/c1-15(28)33-21-20(29)17-14-27(18(24(31)32)13-16-9-6-5-7-10-16)23(30)19(17)26(4)12-8-11-25(2,3)22(21)26/h5-7,9-10,18,20-22,29H,8,11-14H2,1-4H3,(H,31,32)/t18?,20-,21-,22+,26-/m1/s1

InChI Key

KOIFPIZDIMRKTB-PKBPADAASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C3D6O, experimental)	Not Available	Helmholtz Centre for Infection Research	Not Available	2025-07-29	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
Cerrena sp.		Not Available

Chemical Taxonomy

Classification

Not classified

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	2.67	ChemAxon
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	0.44	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	104.14 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	121.28 m³·mol⁻¹	ChemAxon
Polarizability	49.4 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	Yes	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

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BiGG ID

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Wikipedia Link

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METLIN ID

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PubChem Compound

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PDB ID

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ChEBI ID

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Good Scents ID

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References

General References

Paomephan P, Hassan K, Kirchenwitz M, Pfutze S, Surup F, Cisarova I, Boonchird C, Stadler M: The Khamkhains, Neurotrophic Drimane-Type Sesquiterpenoids Derived from a Polyporaceous Basidiomycete Originating from Thailand. J Nat Prod. 2025 Jul 25;88(7):1840-1846. doi: 10.1021/acs.jnatprod.5c00669. Epub 2025 Jul 16. [PubMed:40669013 ]
DOI: 10.1021/acs.jnatprod.5c00669
PMID: 40669013

Showing NP-Card for 6-Acytyl-N-phe-khamkhain C (NP0351374)

MOL for NP0351374 (6-Acytyl-N-phe-khamkhain C)

3D MOL for NP0351374 (6-Acytyl-N-phe-khamkhain C)

3D SDF for NP0351374 (6-Acytyl-N-phe-khamkhain C)

3D-SDF for NP0351374 (6-Acytyl-N-phe-khamkhain C)

PDB for NP0351374 (6-Acytyl-N-phe-khamkhain C)

3D PDB for NP0351374 (6-Acytyl-N-phe-khamkhain C)

SMILES for NP0351374 (6-Acytyl-N-phe-khamkhain C)

INCHI for NP0351374 (6-Acytyl-N-phe-khamkhain C)

Structure for NP0351374 (6-Acytyl-N-phe-khamkhain C)

3D Structure for NP0351374 (6-Acytyl-N-phe-khamkhain C)