NP-MRD: Showing NP-Card for 4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate (NP0214349)

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Record Information

Version

2.0

Created at

2022-09-05 13:37:25 UTC

Updated at

2022-09-05 13:37:25 UTC

NP-MRD ID

NP0214349

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate

Description

Chaxine B belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate is found in Agrocybe chaxingu. 4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate was first documented in 2017 (PMID: 28414246). Based on a literature review a small amount of articles have been published on Chaxine B (PMID: 32090579) (PMID: 28121455).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052215372D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052215372D          

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 19 26  1  0  0  0  0
 26 27  2  0  0  0  0
 14 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 13 32  1  0  0  0  0
 10 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0214349

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)\C=C\C(C)[C@H]1CC[C@H]2\C(=C\C(=O)OC3(C)CCC(O)CC3=O)C(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O5/c1-17(2)18(3)7-8-19(4)22-9-10-23-21(24(30)12-13-27(22,23)5)16-26(32)33-28(6)14-11-20(29)15-25(28)31/h7-8,16-20,22-23,29H,9-15H2,1-6H3/b8-7+,21-16-/t18?,19?,20?,22-,23+,27-,28?/m1/s1

> <INCHI_KEY>
HTXUAQKMNHGMFH-BUQUEDMSSA-N

> <FORMULA>
C28H42O5

> <MOLECULAR_WEIGHT>
458.639

> <EXACT_MASS>
458.303224452

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.79882010810722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1R,3aR,4Z,7aR)-1-[(3E)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-octahydro-1H-inden-4-ylidene]acetate

> <JCHEM_LOGP>
5.946454039666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.60003062850019

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.92005210890703

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7666143551099074

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
131.10419999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-1-methyl-2-oxocyclohexyl [(1R,3aR,4Z,7aR)-1-[(3E)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       3.789 -10.376   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.759  -9.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.253  -9.552   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.235  -7.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.741  -7.447   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.258   4.087   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.591   1.777   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.925   2.547   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.452   1.100   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.935   3.727   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.462   5.174   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.978   5.441   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.505   6.889   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.968   4.262   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.442   2.815   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.431   1.635   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.429  -3.604   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   26                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19   27                                                  
CONECT   27   26                                                            
CONECT   28   14   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   13   10   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂O₅

Average Mass

458.6390 Da

Monoisotopic Mass

458.30322 Da

IUPAC Name

4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1R,3aR,4Z,7aR)-1-[(3E)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-octahydro-1H-inden-4-ylidene]acetate

Traditional Name

4-hydroxy-1-methyl-2-oxocyclohexyl [(1R,3aR,4Z,7aR)-1-[(3E)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate

CAS Registry Number

Not Available

SMILES

CC(C)C(C)\C=C\C(C)[C@H]1CC[C@H]2\C(=C\C(=O)OC3(C)CCC(O)CC3=O)C(=O)CC[C@]12C

InChI Identifier

InChI=1S/C28H42O5/c1-17(2)18(3)7-8-19(4)22-9-10-23-21(24(30)12-13-27(22,23)5)16-26(32)33-28(6)14-11-20(29)15-25(28)31/h7-8,16-20,22-23,29H,9-15H2,1-6H3/b8-7+,21-16-/t18?,19?,20?,22-,23+,27-,28?/m1/s1

InChI Key

HTXUAQKMNHGMFH-BUQUEDMSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agrocybe chaxingu	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Alpha-acyloxy ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.95	ChemAxon
pKa (Strongest Acidic)	14.92	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	131.1 m³·mol⁻¹	ChemAxon
Polarizability	52.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00054307

Chemspider ID

78445277

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587340

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ge FH, Duan MH, Li J, Shi QL: Ganoderin A, a novel 9,11-secosterol from Ganoderma lucidum spores oil. J Asian Nat Prod Res. 2017 Dec;19(12):1252-1257. doi: 10.1080/10286020.2017.1313834. Epub 2017 Apr 17. [PubMed:28414246 ]
Niki M, Hirata Y, Nakazaki A, Wu J, Kawagishi H, Nishikawa T: Biomimetic Synthesis of Chaxine and its Related Compounds. J Org Chem. 2020 Apr 3;85(7):4848-4860. doi: 10.1021/acs.joc.9b03482. Epub 2020 Mar 12. [PubMed:32090579 ]
Hirata Y, Nakazaki A, Kawagishi H, Nishikawa T: Biomimetic Synthesis and Structural Revision of Chaxine B and Its Analogues. Org Lett. 2017 Feb 3;19(3):560-563. doi: 10.1021/acs.orglett.6b03724. Epub 2017 Jan 25. [PubMed:28121455 ]
LOTUS database [Link]

Showing NP-Card for 4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate (NP0214349)

MOL for NP0214349 (4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate)

3D MOL for NP0214349 (4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate)

3D SDF for NP0214349 (4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate)

3D-SDF for NP0214349 (4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate)

PDB for NP0214349 (4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate)

3D PDB for NP0214349 (4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate)

SMILES for NP0214349 (4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate)

INCHI for NP0214349 (4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate)

Structure for NP0214349 (4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate)

3D Structure for NP0214349 (4-hydroxy-1-methyl-2-oxocyclohexyl 2-[(1r,3ar,4z,7ar)-1-[(3e)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-5-oxo-hexahydroinden-4-ylidene]acetate)