NP-MRD: Showing NP-Card for [(3ar,4s,6r,7r,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3ah-1-benzofuran-6-yl]methyl acetate (NP0223878)

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Record Information

Version

2.0

Created at

2022-09-06 02:05:58 UTC

Updated at

2022-09-06 02:05:58 UTC

NP-MRD ID

NP0223878

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3ar,4s,6r,7r,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3ah-1-benzofuran-6-yl]methyl acetate

Description

[(3AR,4S,6R,7R,7aR)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-octahydro-1-benzofuran-6-yl]methyl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review very few articles have been published on [(3aR,4S,6R,7R,7aR)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-octahydro-1-benzofuran-6-yl]methyl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204052D          

 26 27  0  0  1  0            999 V2000
    4.4469    2.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6345    2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1648    1.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    1.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2594    0.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5416    0.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7897    1.5057    0.0000 O   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  2  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   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
   -0.1712    1.5229    0.0000 O   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
    1.9233    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END


  Mrv1652309062204052D          

 26 27  0  0  1  0            999 V2000
    4.4469    2.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6345    2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1648    1.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    1.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2594    0.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5416    0.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7897    1.5057    0.0000 O   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  2  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   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
   -0.1712    1.5229    0.0000 O   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
    1.9233    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0223878

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@]1(C[C@H](OC(C)=O)[C@@H]2[C@H](OC(=O)C2=C)[C@H]1C(=C)C=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O7/c1-6-19(9-24-12(4)21)7-14(25-13(5)22)15-11(3)18(23)26-17(15)16(19)10(2)8-20/h6,8,14-17H,1-3,7,9H2,4-5H3/t14-,15+,16+,17-,19+/m0/s1

> <INCHI_KEY>
YOZNVFKYBMWRIK-WAXPSYRMSA-N

> <FORMULA>
C19H22O7

> <MOLECULAR_WEIGHT>
362.378

> <EXACT_MASS>
362.136553048

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.429777486231785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3aR,4S,6R,7R,7aR)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-octahydro-1-benzofuran-6-yl]methyl acetate

> <JCHEM_LOGP>
0.8850611790000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.808998992813923

> <JCHEM_POLAR_SURFACE_AREA>
95.97

> <JCHEM_REFRACTIVITY>
90.4069

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(3aR,4S,6R,7R,7aR)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3aH-1-benzofuran-6-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       8.301   5.327   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.784   5.060   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.774   3.345   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.301   1.898   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.818   1.631   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.344   0.184   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.807   2.811   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.258  -1.007   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591  -0.237   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.258  -2.547   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.590   8.233   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9   22                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21    3   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
[(3AR,4S,6R,7R,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-octahydro-1-benzofuran-6-yl]methyl acetic acid	Generator

Chemical Formula

C₁₉H₂₂O₇

Average Mass

362.3780 Da

Monoisotopic Mass

362.13655 Da

IUPAC Name

[(3aR,4S,6R,7R,7aR)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-octahydro-1-benzofuran-6-yl]methyl acetate

Traditional Name

[(3aR,4S,6R,7R,7aR)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3aH-1-benzofuran-6-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@]1(C[C@H](OC(C)=O)[C@@H]2[C@H](OC(=O)C2=C)[C@H]1C(=C)C=O)C=C

InChI Identifier

InChI=1S/C19H22O7/c1-6-19(9-24-12(4)21)7-14(25-13(5)22)15-11(3)18(23)26-17(15)16(19)10(2)8-20/h6,8,14-17H,1-3,7,9H2,4-5H3/t14-,15+,16+,17-,19+/m0/s1

InChI Key

YOZNVFKYBMWRIK-WAXPSYRMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Elemanolide-skeleton
Benzofuran
Tricarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated aldehyde
Enal
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aldehyde
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.89	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	95.97 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	90.41 m³·mol⁻¹	ChemAxon
Polarizability	36.43 Å³	ChemAxon
Number of Rings	2	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

162930686

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(3ar,4s,6r,7r,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3ah-1-benzofuran-6-yl]methyl acetate (NP0223878)

MOL for NP0223878 ([(3ar,4s,6r,7r,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3ah-1-benzofuran-6-yl]methyl acetate)

3D MOL for NP0223878 ([(3ar,4s,6r,7r,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3ah-1-benzofuran-6-yl]methyl acetate)

3D SDF for NP0223878 ([(3ar,4s,6r,7r,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3ah-1-benzofuran-6-yl]methyl acetate)

3D-SDF for NP0223878 ([(3ar,4s,6r,7r,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3ah-1-benzofuran-6-yl]methyl acetate)

PDB for NP0223878 ([(3ar,4s,6r,7r,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3ah-1-benzofuran-6-yl]methyl acetate)

3D PDB for NP0223878 ([(3ar,4s,6r,7r,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3ah-1-benzofuran-6-yl]methyl acetate)

SMILES for NP0223878 ([(3ar,4s,6r,7r,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3ah-1-benzofuran-6-yl]methyl acetate)

INCHI for NP0223878 ([(3ar,4s,6r,7r,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3ah-1-benzofuran-6-yl]methyl acetate)

Structure for NP0223878 ([(3ar,4s,6r,7r,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3ah-1-benzofuran-6-yl]methyl acetate)

3D Structure for NP0223878 ([(3ar,4s,6r,7r,7ar)-4-(acetyloxy)-6-ethenyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-tetrahydro-3ah-1-benzofuran-6-yl]methyl acetate)