NP-MRD: Showing NP-Card for methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate (NP0277610)

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Record Information

Version

2.0

Created at

2022-09-09 02:20:43 UTC

Updated at

2022-09-09 02:20:43 UTC

NP-MRD ID

NP0277610

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate

Description

Methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate is found in Lansium domesticum. Methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171515422D          

 38 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171515422D          

 38 41  0  0  0  0            999 V2000
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    5.9420    1.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7618   -0.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4391   -0.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0964   -0.6578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8254   -1.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0006   -1.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  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
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 20 32  1  0  0  0  0
 32 33  2  0  0  0  0
 25 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 34 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0277610

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(OC(C)=O)C1C(C)(C)C(=O)C=CC1(C)C1CCC2(C)C(OC(=O)CC2(O)C1=C)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O9/c1-16-19(8-12-28(6)24(18-10-13-36-15-18)38-21(32)14-29(16,28)34)27(5)11-9-20(31)26(3,4)23(27)22(25(33)35-7)37-17(2)30/h9-11,13,15,19,22-24,34H,1,8,12,14H2,2-7H3

> <INCHI_KEY>
VTJUVXVINSZWCE-UHFFFAOYSA-N

> <FORMULA>
C29H36O9

> <MOLECULAR_WEIGHT>
528.598

> <EXACT_MASS>
528.235932739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.24478762689066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
3.3773920053333315

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.482024846457175

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8861324094073924

> <JCHEM_POLAR_SURFACE_AREA>
129.34

> <JCHEM_REFRACTIVITY>
135.20469999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       7.106   1.534   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.604   3.074   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.902   4.186   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.517   5.003   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.663   4.505   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.046   3.504   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      13.824   3.074   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      15.068   4.430   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      14.637   1.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.223   5.143   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.257   6.343   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.633   6.296   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.234   7.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.813   7.779   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.527   9.385   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.335   8.015   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.301   6.816   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.744   5.380   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.310   6.095   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.033   3.867   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.488   3.361   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.777   1.849   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.612   0.842   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.416   1.062   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.901  -0.671   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.736  -1.678   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.281  -1.172   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.506  -2.600   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.992   0.341   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.157   1.348   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.474   1.222   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.868   2.860   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.092   3.186   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.355  -1.177   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      17.620  -0.297   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      18.847  -1.228   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      18.341  -2.682   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      16.801  -2.651   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   18                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   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   21   32                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   30                                             
CONECT   24   23                                                            
CONECT   25   23   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   23   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   20   33                                                  
CONECT   33   32                                                            
CONECT   34   25   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   34                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetic acid	Generator

Chemical Formula

C₂₉H₃₆O₉

Average Mass

528.5980 Da

Monoisotopic Mass

528.23593 Da

IUPAC Name

methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate

Traditional Name

methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1H-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C(OC(C)=O)C1C(C)(C)C(=O)C=CC1(C)C1CCC2(C)C(OC(=O)CC2(O)C1=C)C1=COC=C1

InChI Identifier

InChI=1S/C29H36O9/c1-16-19(8-12-28(6)24(18-10-13-36-15-18)38-21(32)14-29(16,28)34)27(5)11-9-20(31)26(3,4)23(27)22(25(33)35-7)37-17(2)30/h9-11,13,15,19,22-24,34H,1,8,12,14H2,2-7H3

InChI Key

VTJUVXVINSZWCE-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
Lansium domesticum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Tricarboxylic acid or derivatives
Cyclohexenone
Delta valerolactone
Delta_valerolactone
Oxane
Cyclic alcohol
Heteroaromatic compound
Methyl ester
Tertiary alcohol
Furan
Carboxylic acid ester
Cyclic ketone
Lactone
Ketone
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	3.46	ALOGPS
logP	3.38	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.48	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	129.34 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	135.2 m³·mol⁻¹	ChemAxon
Polarizability	54.24 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	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

56671366

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate (NP0277610)

MOL for NP0277610 (methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate)

3D MOL for NP0277610 (methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate)

3D SDF for NP0277610 (methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate)

3D-SDF for NP0277610 (methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate)

PDB for NP0277610 (methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate)

3D PDB for NP0277610 (methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate)

SMILES for NP0277610 (methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate)

INCHI for NP0277610 (methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate)

Structure for NP0277610 (methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate)

3D Structure for NP0277610 (methyl 2-(acetyloxy)-2-{2-[1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl}acetate)