NP-MRD: Showing NP-Card for 3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3h-spiro[1-benzofuran-2,1'-cyclohexan]-2'-yl]propanoic acid (NP0181305)

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Record Information

Version

2.0

Created at

2022-09-03 19:48:15 UTC

Updated at

2022-09-03 19:48:15 UTC

NP-MRD ID

NP0181305

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3h-spiro[1-benzofuran-2,1'-cyclohexan]-2'-yl]propanoic acid

Description

3-[5'-(2-Hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-3a,4,5,6-tetrahydro-3H-spiro[1-benzofuran-2,1'-cyclohexane]-6'-yl]propanoic acid belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Based on a literature review very few articles have been published on 3-[5'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-3a,4,5,6-tetrahydro-3H-spiro[1-benzofuran-2,1'-cyclohexane]-6'-yl]propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032221482D          

 33 35  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652309032221482D          

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 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0181305

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1C(C)C2(C)CC3(OC2=C(C)C1=O)C(C)CCC(C(C)(C)O)C3(C)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H40O7/c1-14-9-10-17(23(4,5)31)25(7,12-11-18(27)28)26(14)13-24(6)16(3)19(22(30)32-8)20(29)15(2)21(24)33-26/h14,16-17,19,31H,9-13H2,1-8H3,(H,27,28)

> <INCHI_KEY>
DBVLHWIPFHLNFC-UHFFFAOYSA-N

> <FORMULA>
C26H40O7

> <MOLECULAR_WEIGHT>
464.599

> <EXACT_MASS>
464.277403628

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
49.562796254322734

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-3a,4,5,6-tetrahydro-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2'-yl]propanoic acid

> <JCHEM_LOGP>
3.630001312666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.44760923667665

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.659259008939001

> <JCHEM_PKA_STRONGEST_BASIC>
-2.778340609475368

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
123.81260000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2'-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.132   2.016   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.132  -0.476   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.828  -1.532   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.807   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.037   3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.347   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.117   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.347  -0.564   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.117  -1.897   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.887  -3.231   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.783  -2.667   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.451  -1.127   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.807  -0.564   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.753  -2.103   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.501  -1.380   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.555  -2.919   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.249  -3.735   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.889  -3.012   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.303  -5.274   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   16                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18   27                                             
CONECT   13   12   14                                                       
CONECT   14   13   10   15   16                                             
CONECT   15   14                                                            
CONECT   16   14    5   17                                                  
CONECT   17   16                                                            
CONECT   18   12   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   22   12   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
3-[5'-(2-Hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-3a,4,5,6-tetrahydro-3H-spiro[1-benzofuran-2,1'-cyclohexane]-6'-yl]propanoate	Generator

Chemical Formula

C₂₆H₄₀O₇

Average Mass

464.5990 Da

Monoisotopic Mass

464.27740 Da

IUPAC Name

3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-3a,4,5,6-tetrahydro-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2'-yl]propanoic acid

Traditional Name

3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2'-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C1C(C)C2(C)CC3(OC2=C(C)C1=O)C(C)CCC(C(C)(C)O)C3(C)CCC(O)=O

InChI Identifier

InChI=1S/C26H40O7/c1-14-9-10-17(23(4,5)31)25(7,12-11-18(27)28)26(14)13-24(6)16(3)19(22(30)32-8)20(29)15(2)21(24)33-26/h14,16-17,19,31H,9-13H2,1-8H3,(H,27,28)

InChI Key

DBVLHWIPFHLNFC-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

Not Available

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

P-menthane monoterpenoid
Bicyclic monoterpenoid
Carbocyclic fatty acid
Benzofuran
Cyclohexenone
Hydroxy fatty acid
Fatty acyl
1,3-dicarbonyl compound
Dicarboxylic acid or derivatives
Vinylogous ester
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Cyclic ketone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.63	ChemAxon
pKa (Strongest Acidic)	4.66	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.81 m³·mol⁻¹	ChemAxon
Polarizability	49.56 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

162816045

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3h-spiro[1-benzofuran-2,1'-cyclohexan]-2'-yl]propanoic acid (NP0181305)

MOL for NP0181305 (3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3h-spiro[1-benzofuran-2,1'-cyclohexan]-2'-yl]propanoic acid)

3D MOL for NP0181305 (3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3h-spiro[1-benzofuran-2,1'-cyclohexan]-2'-yl]propanoic acid)

3D SDF for NP0181305 (3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3h-spiro[1-benzofuran-2,1'-cyclohexan]-2'-yl]propanoic acid)

3D-SDF for NP0181305 (3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3h-spiro[1-benzofuran-2,1'-cyclohexan]-2'-yl]propanoic acid)

PDB for NP0181305 (3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3h-spiro[1-benzofuran-2,1'-cyclohexan]-2'-yl]propanoic acid)

3D PDB for NP0181305 (3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3h-spiro[1-benzofuran-2,1'-cyclohexan]-2'-yl]propanoic acid)

SMILES for NP0181305 (3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3h-spiro[1-benzofuran-2,1'-cyclohexan]-2'-yl]propanoic acid)

INCHI for NP0181305 (3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3h-spiro[1-benzofuran-2,1'-cyclohexan]-2'-yl]propanoic acid)

Structure for NP0181305 (3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3h-spiro[1-benzofuran-2,1'-cyclohexan]-2'-yl]propanoic acid)

3D Structure for NP0181305 (3-[3'-(2-hydroxypropan-2-yl)-5-(methoxycarbonyl)-2',3a,4,6',7-pentamethyl-6-oxo-4,5-dihydro-3h-spiro[1-benzofuran-2,1'-cyclohexan]-2'-yl]propanoic acid)