NP-MRD: Showing NP-Card for (4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one (NP0254139)

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Record Information

Version

2.0

Created at

2022-09-07 18:12:37 UTC

Updated at

2022-09-07 18:12:37 UTC

NP-MRD ID

NP0254139

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one

Description

Herbertenone b belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, herbertenone b is considered to be an isoprenoid. (4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one is found in Herbertus sakuraii. (4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one was first documented in 2000 (PMID: 11142851). Based on a literature review very few articles have been published on Herbertenone b.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -2.6009   -1.2957   -0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7440   -0.0489   -0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110    0.1264   -1.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7084    1.0889   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5471    1.4872    1.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4643    0.6496    1.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8256   -0.1684    0.5783 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8755   -1.6239    1.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621    0.2049    0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5871   -0.6203    0.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9832   -0.2722    0.2187 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6138   -1.2014   -0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6573   -0.4474    1.4510 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2554    1.0935   -0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2855    1.9661   -0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9190    1.5500   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0200    2.3745   -0.2518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3684   -1.3373    0.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0456   -2.2158   -0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1744   -1.1272   -1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3430   -0.6095   -2.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3065    1.1227   -2.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0760   -0.0027   -1.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5955    1.9246   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7875    0.7772   -0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080    1.3688    1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3341    2.5925    1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9048    0.0103    2.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6785    1.2486    2.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9120   -1.8705    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4580   -2.3362    0.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2453   -1.6462    1.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3851   -1.6345    0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7195   -1.0472   -0.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402   -0.8417   -1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3521   -2.2449   -0.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9982   -1.3693    1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3062    1.3911   -0.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5176    2.9847   -0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  1
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  7  2  1  0
 16  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
M  END

  Mrv1652309072220122D          

 17 18  0  0  1  0            999 V2000
    1.6110   -0.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590   -1.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5069   -0.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7264   -1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4715   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6465   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3915   -1.6320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4172   -1.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1669   -1.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9720   -1.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5304   -0.5975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0315   -1.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2629   -0.2178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837    0.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4786    0.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0798   -0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850   -0.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  6  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0254139

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@]1(C)C1=C[C@](C)(O)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-13(2)7-5-8-15(13,4)11-10-14(3,17)9-6-12(11)16/h6,9-10,17H,5,7-8H2,1-4H3/t14-,15-/m1/s1

> <INCHI_KEY>
IAHVMQAYDBMMQB-HUUCEWRRSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.60641089271782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-hydroxy-4-methyl-2-[(1S)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one

> <JCHEM_LOGP>
3.129177319666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.21031962520886

> <JCHEM_PKA_STRONGEST_BASIC>
-3.144206195933644

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.83899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-hydroxy-4-methyl-2-[(1S)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.007  -0.997   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.977  -2.141   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.946  -0.997   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.223  -3.046   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.747  -4.511   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.207  -4.511   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.731  -3.046   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.779  -3.351   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.312  -1.913   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.814  -2.249   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.857  -1.115   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.792  -2.339   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.224  -0.407   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.396   0.354   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.893   0.690   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.149  -0.443   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.652  -0.107   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3390 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]1(C)C1=C[C@](C)(O)C=CC1=O

InChI Identifier

InChI=1S/C15H22O2/c1-13(2)7-5-8-15(13,4)11-10-14(3,17)9-6-12(11)16/h6,9-10,17H,5,7-8H2,1-4H3/t14-,15-/m1/s1

InChI Key

IAHVMQAYDBMMQB-HUUCEWRRSA-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
Herbertus sakuraii	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

Herbertane sesquiterpenoid
Sesquiterpenoid
Tertiary alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00037265

Chemspider ID

74105200

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15545712

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Irita H, Hashimoto T, Fukuyama Y, Asakawa Y: Herbertane-type sesquiterpenoids from the liverwort Herbertus sakuraii. Phytochemistry. 2000 Oct;55(3):247-53. doi: 10.1016/s0031-9422(00)00317-4. [PubMed:11142851 ]
LOTUS database [Link]

Showing NP-Card for (4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one (NP0254139)

MOL for NP0254139 ((4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one)

3D MOL for NP0254139 ((4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one)

3D SDF for NP0254139 ((4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one)

3D-SDF for NP0254139 ((4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one)

PDB for NP0254139 ((4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one)

3D PDB for NP0254139 ((4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one)

SMILES for NP0254139 ((4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one)

INCHI for NP0254139 ((4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one)

Structure for NP0254139 ((4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one)

3D Structure for NP0254139 ((4r)-4-hydroxy-4-methyl-2-[(1s)-1,2,2-trimethylcyclopentyl]cyclohexa-2,5-dien-1-one)