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Showing NP-Card for (2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one (NP0328535)

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Record Information
Version1.0
Created at2022-09-12 12:05:44 UTC
Updated at2022-09-12 12:05:44 UTC
NP-MRD IDNP0328535
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one
Description(2R,3S,3aS,7aS)-2-(1,3-Benzodioxole-5-yl)-2,3,3a,7a-tetrahydro-7a-hydroxy-3-methyl-3a-(2-propenyl)-7(4H)-benzofuranone belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. (2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one is found in Ocotea aciphylla. It was first documented in 2022 (PMID: 36130844). Based on a literature review a significant number of articles have been published on (2R,3S,3aS,7aS)-2-(1,3-Benzodioxole-5-yl)-2,3,3a,7a-tetrahydro-7a-hydroxy-3-methyl-3a-(2-propenyl)-7(4H)-benzofuranone (PMID: 36130843) (PMID: 36130842) (PMID: 36130841) (PMID: 36130840).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)


  Mrv1652309122214052D          

 24 27  0  0  1  0            999 V2000
    5.6311    4.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8106    4.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750    4.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    3.3400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3725    4.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1975    4.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6100    3.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1975    2.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6100    1.9110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725    2.6255    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7080    1.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8204    2.0124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530    3.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5399    3.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 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
 17 22  1  0  0  0  0
 13 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  1  0  0  0
M  END
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3D MOL for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)

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3D SDF for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)

  Mrv1652309122214052D          

 24 27  0  0  1  0            999 V2000
    5.6311    4.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8106    4.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750    4.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    3.3400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3725    4.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1975    4.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6100    3.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1975    2.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6100    1.9110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725    2.6255    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7080    1.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8204    2.0124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530    3.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5399    3.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 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
 17 22  1  0  0  0  0
 13 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0328535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H](O[C@]2(O)C(=O)C=CC[C@@]12CC=C)C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O5/c1-3-8-18-9-4-5-16(20)19(18,21)24-17(12(18)2)13-6-7-14-15(10-13)23-11-22-14/h3-7,10,12,17,21H,1,8-9,11H2,2H3/t12-,17-,18+,19-/m1/s1

> <INCHI_KEY>
ZWZOJVXHAOTSDM-GBRSUSRYSA-N

> <FORMULA>
C19H20O5

> <MOLECULAR_WEIGHT>
328.364

> <EXACT_MASS>
328.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.74131028022762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,3aS,7aS)-2-(2H-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-7-one

> <JCHEM_LOGP>
3.847620131666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.75665750688913

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.963582564051517

> <JCHEM_PKA_STRONGEST_BASIC>
-4.259294912522463

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
88.03200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,3aS,7aS)-2-(2H-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2H-1-benzofuran-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)
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PDB for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.511   9.048   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.980   8.887   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.353   7.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.259   6.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.029   7.568   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.569   7.568   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.339   6.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.569   4.901   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.339   3.567   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.029   4.901   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.655   3.494   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.998   3.756   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.752   5.914   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.608   6.945   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10   23                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   13    4   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

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3D PDB for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)
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SMILES for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)
C[C@@H]1[C@@H](O[C@]2(O)C(=O)C=CC[C@@]12CC=C)C1=CC=C2OCOC2=C1
Download
INCHI for NP0328535 ((2r,3s,3as,7as)-2-(2h-1,3-benzodioxol-5-yl)-7a-hydroxy-3-methyl-3a-(prop-2-en-1-yl)-3,4-dihydro-2h-1-benzofuran-7-one)
InChI=1S/C19H20O5/c1-3-8-18-9-4-5-16(20)19(18,21)24-17(12(18)2)13-6-7-14-15(10-13)23-11-22-14/h3-7,10,12,17,21H,1,8-9,11H2,2H3/t12-,17-,18+,19-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC19H20O5
Average Mass328.3640 Da
Monoisotopic Mass328.13107 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
C[C@@H]1[C@@H](O[C@]2(O)C(=O)C=CC[C@@]12CC=C)C1=CC=C2OCOC2=C1
InChI Identifier
InChI=1S/C19H20O5/c1-3-8-18-9-4-5-16(20)19(18,21)24-17(12(18)2)13-6-7-14-15(10-13)23-11-22-14/h3-7,10,12,17,21H,1,8-9,11H2,2H3/t12-,17-,18+,19-/m1/s1
InChI KeyZWZOJVXHAOTSDM-GBRSUSRYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ocotea aciphyllaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzodioxoles  
Sub ClassNot Available
Direct ParentBenzodioxoles  
Alternative Parents
Substituents
  • Benzofuran
    • 

  • Benzodioxole
    • 

  • Cyclohexenone
    • 

  • Benzenoid
    • 

  • Tetrahydrofuran
    • 

  • Ketone
    • 

  • Hemiacetal
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15126691  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Cani I, Righini M, Cenni P, Foschi M: Teaching NeuroImage: Partially Reversible Widespread Leukoencephalopathy Associated With Atypical Hemolytic Uremic Syndrome. Neurology. 2022 Sep 21. pii: WNL.0000000000201378. doi: 10.1212/WNL.0000000000201378. [PubMed:36130844  ] 
  2. Sasaki R, Morimoto S, Ozawa F, Okano H, Yoshida M, Ishiura H, Tsuji S, Kuzuhara S, Kokubo Y: APOE Alleles With Tau and Abeta Pathology In Patients With Amyotrophic Lateral Sclerosis and Parkinsonism-Dementia Complex in the Kii Peninsula. Neurology. 2022 Sep 21. pii: WNL.0000000000201156. doi: 10.1212/WNL.0000000000201156. [PubMed:36130843  ] 
  3. Zhang Z, Wang M, Gill D, Liu X: Genetically Predicted Smoking and Alcohol Consumption and Functional Outcome After Ischemic Stroke. Neurology. 2022 Sep 21. pii: WNL.0000000000201291. doi: 10.1212/WNL.0000000000201291. [PubMed:36130842  ] 
  4. Khamis S, Mitakidou MR, Champion M, Goyal S, Jones RL, Siddiqui A, Sabanathan S, Hedderly T, Lin JP, Jungbluth H, Papandreou A: Clinical Reasoning: A Teenage Girl With Progressive Hyperkinetic Movements, Seizures, and Encephalopathy. Neurology. 2022 Sep 21. pii: WNL.0000000000201385. doi: 10.1212/WNL.0000000000201385. [PubMed:36130841  ] 
  5. Rosenberg A, Ohlund-Wistbacka U, Hall A, Bonnard A, Hagman G, Ryden M, Thunborg C, Wiggenraad F, Sandebring-Matton A, Solomon A, Kivipelto M: beta-Amyloid, Tau, Neurodegeneration Classification and Eligibility for Anti-amyloid Treatment in a Memory Clinic Population. Neurology. 2022 Sep 21. pii: WNL.0000000000201043. doi: 10.1212/WNL.0000000000201043. [PubMed:36130840  ] 
  6. LOTUS database [Link]