NP-MRD: Showing NP-Card for 6-Acytyl-N-isoleucyl-khamkhain C (NP0351373)

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Record Information

Version

2.0

Created at

2025-07-29 21:57:03 UTC

Updated at

2025-07-31 00:03:51 UTC

NP-MRD ID

NP0351373

Natural Product DOI

https://doi.org/10.57994/4413

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Acytyl-N-isoleucyl-khamkhain C

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02022315072D          

 31 33  0  0  1  0            999 V2000
   -0.8006   -0.3763    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131   -1.0908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6256   -1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8503   -2.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688   -2.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506   -1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8631   -1.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506   -0.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6256   -0.3763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0381    0.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131    0.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881    0.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1331    1.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8006    1.6077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8006    2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5150    2.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295    2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5150    3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295    4.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0861    2.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0861    3.6702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284    2.4327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4680    1.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2526    1.3777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244   -0.3763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8494   -0.3763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -1.0908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0244   -1.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -2.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244   -3.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131   -2.5197    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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 14 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25 12  1  0  0  0  0
 25 26  1  1  0  0  0
 27 25  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END


  Mrv2104 02022315072D          

 31 33  0  0  1  0            999 V2000
   -0.8006   -0.3763    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131   -1.0908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6256   -1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8503   -2.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688   -2.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506   -1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8631   -1.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506   -0.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6256   -0.3763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0381    0.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131    0.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881    0.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1331    1.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8006    1.6077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8006    2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5150    2.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295    2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5150    3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295    4.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0861    2.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0861    3.6702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284    2.4327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4680    1.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2526    1.3777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244   -0.3763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8494   -0.3763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -1.0908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0244   -1.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -2.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244   -3.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131   -2.5197    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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 14 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25 12  1  0  0  0  0
 25 26  1  1  0  0  0
 27 25  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0351373

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H35NO6/c1-7-12(2)16(21(28)29)24-11-14-15(20(24)27)23(6)10-8-9-22(4,5)19(23)18(17(14)26)30-13(3)25/h12,16-19,26H,7-11H2,1-6H3,(H,28,29)/t12?,16?,17-,18-,19+,23-/m1/s1

> <INCHI_KEY>
JCIQUEVQPHXHQE-NIYUMCJISA-N

> <FORMULA>
C23H35NO6

> <MOLECULAR_WEIGHT>
421.534

> <EXACT_MASS>
421.246437851

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.00532055342445

> <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-methylpentanoic acid

> <JCHEM_LOGP>
2.3408597650000003

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.040245495360645

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9346329899003973

> <JCHEM_PKA_STRONGEST_BASIC>
0.7806989233740054

> <JCHEM_POLAR_SURFACE_AREA>
104.14000000000001

> <JCHEM_REFRACTIVITY>
110.25519999999999

> <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-methylpentanoic 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      -1.494  -0.702   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -2.264  -2.036   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.034  -3.370   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.587  -3.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.302  -4.886   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.574  -3.370   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.344  -2.036   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.574  -0.702   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.034  -0.702   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.804   0.631   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.264   0.631   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.724   0.631   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.249   2.096   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.494   3.001   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -1.494   4.541   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.828   5.311   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.162   4.541   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.828   6.851   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.162   7.621   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.161   5.311   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.161   6.851   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.173   4.541   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.740   2.096   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.205   2.572   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.046  -0.702   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.586  -0.702   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.724  -2.036   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.046  -3.370   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.724  -4.704   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.046  -6.037   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.264  -4.704   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9   27                                             
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   23                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   14   11   24                                                  
CONECT   24   23                                                            
CONECT   25   12   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    2   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₅NO₆

Average Mass

421.5340 Da

Monoisotopic Mass

421.24644 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-methylpentanoic 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-methylpentanoic 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(C(C)CC)C(O)=O)[C@@]1(C)CCCC2(C)C

InChI Identifier

InChI=1S/C23H35NO6/c1-7-12(2)16(21(28)29)24-11-14-15(20(24)27)23(6)10-8-9-22(4,5)19(23)18(17(14)26)30-13(3)25/h12,16-19,26H,7-11H2,1-6H3,(H,28,29)/t12?,16?,17-,18-,19+,23-/m1/s1

InChI Key

JCIQUEVQPHXHQE-NIYUMCJISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 700 MHz, C3D6O, experimental)	Not Available	Helmholtz Centre for Infection Research	Not Available	2025-07-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, C2D6OS, experimental)	Not Available	Helmholtz Centre for Infection Research	Not Available	2025-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 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	2.34	ChemAxon
pKa (Strongest Acidic)	3.93	ChemAxon
pKa (Strongest Basic)	0.78	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	110.26 m³·mol⁻¹	ChemAxon
Polarizability	46.01 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	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

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

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-isoleucyl-khamkhain C (NP0351373)

MOL for NP0351373 (6-Acytyl-N-isoleucyl-khamkhain C)

3D MOL for NP0351373 (6-Acytyl-N-isoleucyl-khamkhain C)

3D SDF for NP0351373 (6-Acytyl-N-isoleucyl-khamkhain C)

3D-SDF for NP0351373 (6-Acytyl-N-isoleucyl-khamkhain C)

PDB for NP0351373 (6-Acytyl-N-isoleucyl-khamkhain C)

3D PDB for NP0351373 (6-Acytyl-N-isoleucyl-khamkhain C)

SMILES for NP0351373 (6-Acytyl-N-isoleucyl-khamkhain C)

INCHI for NP0351373 (6-Acytyl-N-isoleucyl-khamkhain C)

Structure for NP0351373 (6-Acytyl-N-isoleucyl-khamkhain C)

3D Structure for NP0351373 (6-Acytyl-N-isoleucyl-khamkhain C)