NP-MRD: Showing NP-Card for 3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one (NP0191685)

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Record Information

Version

2.0

Created at

2022-09-04 08:43:23 UTC

Updated at

2022-09-04 08:43:23 UTC

NP-MRD ID

NP0191685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one

Description

CHEMBL3581591 belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one is found in Hypericum henryi. Based on a literature review very few articles have been published on CHEMBL3581591.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042210432D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042210432D          

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    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  1  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 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
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 27 34  2  0  0  0  0
 11 34  1  0  0  0  0
 34 35  1  0  0  0  0
 10 36  1  0  0  0  0
  4 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)C1=C(O)C([C@H]2C[C@H](CC[C@@]2(C)O)C(C)=C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H46O5/c1-10-21(8)26(32)25-27(33)24(23-17-22(20(6)7)13-14-30(23,9)36)28(34)31(29(25)35,15-11-18(2)3)16-12-19(4)5/h11-12,21-23,33-34,36H,6,10,13-17H2,1-5,7-9H3/t21?,22-,23+,30+/m0/s1

> <INCHI_KEY>
LVXMXPFAKOESBU-HBGBDTIESA-N

> <FORMULA>
C31H46O5

> <MOLECULAR_WEIGHT>
498.704

> <EXACT_MASS>
498.334524581

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.004759523069346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5-dihydroxy-4-[(1R,2R,5S)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one

> <JCHEM_LOGP>
6.404355544666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.034286779271726

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.53992815109545

> <JCHEM_PKA_STRONGEST_BASIC>
-2.930975121799529

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
150.28719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dihydroxy-4-[(1R,2R,5S)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.344  -1.130   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.324  -1.130   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.828   0.912   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.838   2.092   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.322   1.825   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.365   3.539   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.841   0.912   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.831   2.092   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.348   1.825   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.304   3.539   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   36                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   36                                                  
CONECT   11   10   12   34                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20   25                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   14   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   34                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   27   11   35                                                  
CONECT   35   34                                                            
CONECT   36   10    4                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₆O₅

Average Mass

498.7040 Da

Monoisotopic Mass

498.33452 Da

IUPAC Name

3,5-dihydroxy-4-[(1R,2R,5S)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one

Traditional Name

3,5-dihydroxy-4-[(1R,2R,5S)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)C1=C(O)C([C@H]2C[C@H](CC[C@@]2(C)O)C(C)=C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O

InChI Identifier

InChI=1S/C31H46O5/c1-10-21(8)26(32)25-27(33)24(23-17-22(20(6)7)13-14-30(23,9)36)28(34)31(29(25)35,15-11-18(2)3)16-12-19(4)5/h11-12,21-23,33-34,36H,6,10,13-17H2,1-5,7-9H3/t21?,22-,23+,30+/m0/s1

InChI Key

LVXMXPFAKOESBU-HBGBDTIESA-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
Hypericum henryi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
P-menthane monoterpenoid
Cyclohexanol
Cyclic alcohol
Tertiary alcohol
Vinylogous acid
Ketone
Cyclic ketone
Enol
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
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
logP	6.4	ChemAxon
pKa (Strongest Acidic)	4.54	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	150.29 m³·mol⁻¹	ChemAxon
Polarizability	57 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

59006459

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122178962

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one (NP0191685)

MOL for NP0191685 (3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D MOL for NP0191685 (3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D SDF for NP0191685 (3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D-SDF for NP0191685 (3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

PDB for NP0191685 (3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D PDB for NP0191685 (3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

SMILES for NP0191685 (3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

INCHI for NP0191685 (3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

Structure for NP0191685 (3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)

3D Structure for NP0191685 (3,5-dihydroxy-4-[(1r,2r,5s)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexyl]-6,6-bis(3-methylbut-2-en-1-yl)-2-(2-methylbutanoyl)cyclohexa-2,4-dien-1-one)