NP-MRD: Showing NP-Card for 1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one (NP0299291)

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Record Information

Version

2.0

Created at

2022-09-10 11:02:35 UTC

Updated at

2022-09-10 11:02:35 UTC

NP-MRD ID

NP0299291

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one

Description

1-{2,4-Dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]Nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propan-2-one belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. 1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one is found in Cystoseira mediterranea. 1-{2,4-Dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]Nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propan-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161522092D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161522092D          

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M  END
> <DATABASE_ID>
NP0299291

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=CC2=C1OC(C)(CC(=O)CC1(C)CC3C(O)=CC(O)=CC1(C)C3(C)C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O5/c1-16-9-18(28)10-17-7-8-26(5,32-23(16)17)13-20(30)12-25(4)15-21-22(31)11-19(29)14-27(25,6)24(21,2)3/h9-11,14,21,28-29,31H,7-8,12-13,15H2,1-6H3

> <INCHI_KEY>
FFULEBUZIACVCW-UHFFFAOYSA-N

> <FORMULA>
C27H36O5

> <MOLECULAR_WEIGHT>
440.58

> <EXACT_MASS>
440.256274259

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.00472955225395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propan-2-one

> <ALOGPS_LOGP>
4.83

> <JCHEM_LOGP>
4.795507365666667

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.160418176235195

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.797962446985714

> <JCHEM_PKA_STRONGEST_BASIC>
-4.85315645859133

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
127.83940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.185  -2.043   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.195  -3.757   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.205  -4.937   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.689  -4.669   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.732  -6.384   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.742  -7.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.138  -8.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.859  -6.302   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.342  -6.035   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.081  -6.918   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.813  -8.435   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.697  -9.696   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.213  -9.964   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.475  -9.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.773  -9.908   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.789  -7.291   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.856  -8.516   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.319  -7.748   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.869 -10.995   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.782  -6.091   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   32                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   31                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18   24                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   16   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   19   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   22                                                            
CONECT   30   20                                                            
CONECT   31   10   32                                                       
CONECT   32   31    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆O₅

Average Mass

440.5800 Da

Monoisotopic Mass

440.25627 Da

IUPAC Name

1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propan-2-one

Traditional Name

1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC2=C1OC(C)(CC(=O)CC1(C)CC3C(O)=CC(O)=CC1(C)C3(C)C)CC2

InChI Identifier

InChI=1S/C27H36O5/c1-16-9-18(28)10-17-7-8-26(5,32-23(16)17)13-20(30)12-25(4)15-21-22(31)11-19(29)14-27(25,6)24(21,2)3/h9-11,14,21,28-29,31H,7-8,12-13,15H2,1-6H3

InChI Key

FFULEBUZIACVCW-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
Ericaria mediterranea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Ketone
Oxacycle
Ether
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.83	ALOGPS
logP	4.8	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	8.8	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.84 m³·mol⁻¹	ChemAxon
Polarizability	49 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

73836484

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one (NP0299291)

MOL for NP0299291 (1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one)

3D MOL for NP0299291 (1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one)

3D SDF for NP0299291 (1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one)

3D-SDF for NP0299291 (1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one)

PDB for NP0299291 (1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one)

3D PDB for NP0299291 (1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one)

SMILES for NP0299291 (1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one)

INCHI for NP0299291 (1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one)

Structure for NP0299291 (1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one)

3D Structure for NP0299291 (1-{2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-3-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)propan-2-one)