NP-MRD: Showing NP-Card for 4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one (NP0311346)

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Record Information

Version

2.0

Created at

2022-09-11 07:16:47 UTC

Updated at

2022-09-11 07:16:47 UTC

NP-MRD ID

NP0311346

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one

Description

4-Hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one is found in Hypericum geminiflorum. 4-Hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261504542D          

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  7 28  1  0  0  0  0
 28 29  2  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0311346

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)C1=C(O)C2(C)CC(OC2=C(CC2C(CCC2(C)O)C(C)=C)C1=O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O6/c1-9-15(4)21(28)20-22(29)17(12-18-16(14(2)3)10-11-27(18,8)32)24-26(7,23(20)30)13-19(33-24)25(5,6)31/h15-16,18-19,30-32H,2,9-13H2,1,3-8H3

> <INCHI_KEY>
ORJPPNKFLPAUGB-UHFFFAOYSA-N

> <FORMULA>
C27H40O6

> <MOLECULAR_WEIGHT>
460.611

> <EXACT_MASS>
460.282489008

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.87762105849291

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
3.680175582

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.307378879183759

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8949836165538763

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6701605775175631

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
129.9231

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       9.199   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.865   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.198  -0.237   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.530  -0.237   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.036   0.541   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.864   6.693   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.271   6.066   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.301   7.211   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.531   8.545   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.025   8.224   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.522   8.560   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.534   9.684   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.591   4.560   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.447   3.530   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.056   4.084   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.009   2.582   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.253   2.843   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.713   4.383   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.713   1.303   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   28                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   15                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   30                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18   23   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   19   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   16    7   29                                                  
CONECT   29   28                                                            
CONECT   30   13   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀O₆

Average Mass

460.6110 Da

Monoisotopic Mass

460.28249 Da

IUPAC Name

4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one

Traditional Name

4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)C1=C(O)C2(C)CC(OC2=C(CC2C(CCC2(C)O)C(C)=C)C1=O)C(C)(C)O

InChI Identifier

InChI=1S/C27H40O6/c1-9-15(4)21(28)20-22(29)17(12-18-16(14(2)3)10-11-27(18,8)32)24-26(7,23(20)30)13-19(33-24)25(5,6)31/h15-16,18-19,30-32H,2,9-13H2,1,3-8H3

InChI Key

ORJPPNKFLPAUGB-UHFFFAOYSA-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 geminiflorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Benzofuran
Cyclopentanol
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Vinylogous acid
Vinylogous ester
Ketone
Cyclic ketone
Enol
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	2.94	ALOGPS
logP	3.68	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	-0.67	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.92 m³·mol⁻¹	ChemAxon
Polarizability	50.88 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one (NP0311346)

MOL for NP0311346 (4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

3D MOL for NP0311346 (4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

3D SDF for NP0311346 (4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

3D-SDF for NP0311346 (4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

PDB for NP0311346 (4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

3D PDB for NP0311346 (4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

SMILES for NP0311346 (4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

INCHI for NP0311346 (4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

Structure for NP0311346 (4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)

3D Structure for NP0311346 (4-hydroxy-7-{[2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclopentyl]methyl}-2-(2-hydroxypropan-2-yl)-3a-methyl-5-(2-methylbutanoyl)-2,3-dihydro-1-benzofuran-6-one)