NP-MRD: Showing NP-Card for 3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate (NP0304980)

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Record Information

Version

1.0

Created at

2022-09-10 20:26:53 UTC

Updated at

2022-09-10 20:26:53 UTC

NP-MRD ID

NP0304980

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate

Description

3-({6,6,9,10,12A-pentamethyl-3-oxo-1H,2H,3H,6H,7H,8H,8aH,9H,10H,11H,12H,12aH-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate is found in Stypopodium zonale and Taonia atomaria. 3-({6,6,9,10,12A-pentamethyl-3-oxo-1H,2H,3H,6H,7H,8H,8aH,9H,10H,11H,12H,12aH-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251514252D          

 35 38  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1533004251514252D          

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  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  7 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 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
 26 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 24 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304980

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(C)C(CCC3=C2CCC(=O)OOC3(C)C)C1(C)CC1=CC(OC(C)=O)=CC(C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O6/c1-17-14-21(33-19(3)30)15-20(26(17)32)16-29(7)18(2)12-13-28(6)23-9-11-25(31)34-35-27(4,5)22(23)8-10-24(28)29/h14-15,18,24,32H,8-13,16H2,1-7H3

> <INCHI_KEY>
PFIJWBMKLUYYTJ-UHFFFAOYSA-N

> <FORMULA>
C29H40O6

> <MOLECULAR_WEIGHT>
484.633

> <EXACT_MASS>
484.282489008

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.71831685029554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-({6,6,9,10,12a-pentamethyl-3-oxo-1H,2H,3H,6H,7H,8H,8aH,9H,10H,11H,12H,12aH-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate

> <ALOGPS_LOGP>
6.65

> <JCHEM_LOGP>
6.162134764666665

> <ALOGPS_LOGS>
-5.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.115338644710054

> <JCHEM_PKA_STRONGEST_BASIC>
-5.413621131379761

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
134.23860000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-({6,6,9,10,12a-pentamethyl-3-oxo-1H,2H,7H,8H,8aH,10H,11H,12H-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      10.017   0.611   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.479   0.690   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.641  -0.602   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.103  -0.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.403   0.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.565  -0.443   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.241   2.142   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.541   3.513   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.003   3.593   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.165   2.301   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.865   0.929   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.390  -0.536   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.018  -1.236   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.553  -0.761   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.446  -1.933   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.147   0.611   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.328   2.076   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.700   2.776   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.269   4.207   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.912   4.099   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.779   2.062   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.912   3.596   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.125   2.810   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.151   4.349   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.830   5.142   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.856   6.681   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.536   7.474   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.561   9.014   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.241   9.806   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.908   9.761   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.203   7.429   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.523   6.637   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.870   7.384   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.497   5.097   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      11.818   4.305   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   19   20                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    7    2   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   34                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   26   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   24   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
3-({6,6,9,10,12a-pentamethyl-3-oxo-1H,2H,3H,6H,7H,8H,8ah,9H,10H,11H,12H,12ah-naphtho[2,1-D][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetic acid	Generator

Chemical Formula

C₂₉H₄₀O₆

Average Mass

484.6330 Da

Monoisotopic Mass

484.28249 Da

IUPAC Name

3-({6,6,9,10,12a-pentamethyl-3-oxo-1H,2H,3H,6H,7H,8H,8aH,9H,10H,11H,12H,12aH-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate

Traditional Name

3-({6,6,9,10,12a-pentamethyl-3-oxo-1H,2H,7H,8H,8aH,10H,11H,12H-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate

CAS Registry Number

Not Available

SMILES

CC1CCC2(C)C(CCC3=C2CCC(=O)OOC3(C)C)C1(C)CC1=CC(OC(C)=O)=CC(C)=C1O

InChI Identifier

InChI=1S/C29H40O6/c1-17-14-21(33-19(3)30)15-20(26(17)32)16-29(7)18(2)12-13-28(6)23-9-11-25(31)34-35-27(4,5)22(23)8-10-24(28)29/h14-15,18,24,32H,8-13,16H2,1-7H3

InChI Key

PFIJWBMKLUYYTJ-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
Stypopodium zonale	LOTUS Database	35616633
Taonia atomaria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Phenol ester
Phenoxy compound
O-cresol
Oxocin
Phenol
Toluene
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Carboxylic acid ester
Carboxylic acid salt
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Organic salt
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	6.65	ALOGPS
logP	6.16	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	10.12	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	134.24 m³·mol⁻¹	ChemAxon
Polarizability	53.72 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

74051432

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate (NP0304980)

MOL for NP0304980 (3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate)

3D MOL for NP0304980 (3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate)

3D SDF for NP0304980 (3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate)

3D-SDF for NP0304980 (3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate)

PDB for NP0304980 (3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate)

3D PDB for NP0304980 (3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate)

SMILES for NP0304980 (3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate)

INCHI for NP0304980 (3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate)

Structure for NP0304980 (3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate)

3D Structure for NP0304980 (3-({6,6,9,10,12a-pentamethyl-3-oxo-1h,2h,7h,8h,8ah,10h,11h,12h-naphtho[2,1-d][1,2]dioxocin-9-yl}methyl)-4-hydroxy-5-methylphenyl acetate)