NP-MRD: Showing NP-Card for 12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one (NP0253733)

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Record Information

Version

2.0

Created at

2022-09-07 17:41:12 UTC

Updated at

2022-09-07 17:41:12 UTC

NP-MRD ID

NP0253733

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one

Description

12-[(6-Hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]Dodeca-1(12),10-dien-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. 12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one is found in Cystoseira amentacea and Cystoseira mediterranea. 12-[(6-Hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]Dodeca-1(12),10-dien-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191522562D          

 31 34  0  0  0  0            999 V2000
    0.1993    5.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1993    4.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5152    3.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5152    3.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2296    2.7127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1993    2.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9138    3.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6283    2.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    3.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    3.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2924    3.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1456    4.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4374    4.8687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908    4.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4711    4.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0640    4.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9190    5.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4538    5.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6290    6.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6283    4.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004191522562D          

 31 34  0  0  0  0            999 V2000
    0.1993    5.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1993    4.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0253733

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=CC2=C1OC(C)(CC1=C3C=CC(C)(C)OC1C(C)(C)CCCC3=O)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O4/c1-17-14-19(28)15-18-9-13-27(6,30-23(17)18)16-21-20-10-12-26(4,5)31-24(21)25(2,3)11-7-8-22(20)29/h10,12,14-15,24,28H,7-9,11,13,16H2,1-6H3

> <INCHI_KEY>
KBFOCGHMSLRJND-UHFFFAOYSA-N

> <FORMULA>
C27H36O4

> <MOLECULAR_WEIGHT>
424.581

> <EXACT_MASS>
424.261359639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.587111231167974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one

> <ALOGPS_LOGP>
6.26

> <JCHEM_LOGP>
6.008227881333332

> <ALOGPS_LOGS>
-5.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.140608211134753

> <JCHEM_PKA_STRONGEST_BASIC>
-4.144699749778097

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
125.23789999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       0.372   9.684   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.372   8.144   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.962   7.374   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.962   5.834   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.295   5.064   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.372   5.064   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.706   5.834   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.039   5.064   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.373   5.834   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.373   7.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.146   6.468   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.872   7.921   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.416   9.088   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.703   7.678   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.346   7.676   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.453   8.832   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.182  10.367   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.738  10.778   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.856  11.869   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.747  11.075   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.203  10.512   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.580  10.778   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.907  12.372   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.736  12.219   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.182   9.966   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.677   8.606   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.677   7.157   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.269   6.872   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.966   4.976   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.039   8.144   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.706   7.374   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   31                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   30                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   13   22                                                  
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   14   29                                                  
CONECT   29   28                                                            
CONECT   30   10   31                                                       
CONECT   31   30    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆O₄

Average Mass

424.5810 Da

Monoisotopic Mass

424.26136 Da

IUPAC Name

12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one

Traditional Name

12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC2=C1OC(C)(CC1=C3C=CC(C)(C)OC1C(C)(C)CCCC3=O)CC2

InChI Identifier

InChI=1S/C27H36O4/c1-17-14-19(28)15-18-9-13-27(6,30-23(17)18)16-21-20-10-12-26(4,5)31-24(21)25(2,3)11-7-8-22(20)29/h10,12,14-15,24,28H,7-9,11,13,16H2,1-6H3

InChI Key

KBFOCGHMSLRJND-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
Cystoseira amentacea	LOTUS Database	35616633
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
Phenol
Alkyl aryl ether
Benzenoid
Ketone
Oxacycle
Ether
Dialkyl ether
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	6.26	ALOGPS
logP	6.01	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	10.14	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	125.24 m³·mol⁻¹	ChemAxon
Polarizability	47.59 Å³	ChemAxon
Number of Rings	4	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

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

21637516

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one (NP0253733)

MOL for NP0253733 (12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one)

3D MOL for NP0253733 (12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one)

3D SDF for NP0253733 (12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one)

3D-SDF for NP0253733 (12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one)

PDB for NP0253733 (12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one)

3D PDB for NP0253733 (12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one)

SMILES for NP0253733 (12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one)

INCHI for NP0253733 (12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one)

Structure for NP0253733 (12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one)

3D Structure for NP0253733 (12-[(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodeca-1(12),10-dien-2-one)