NP-MRD: Showing NP-Card for (1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate (NP0183019)

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Record Information

Version

2.0

Created at

2022-09-03 21:51:18 UTC

Updated at

2022-09-03 21:51:19 UTC

NP-MRD ID

NP0183019

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate

Description

(3S)-3beta-(3-Furyl)-4alpha-(benzoyloxy)-7alpha,5alpha-(epoxymethano)-5-methyl-3,4,5,6,7,8-hexahydro-1H-2-benzopyran-1,10-dione belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. (1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate is found in Rhodocollybia maculata. Based on a literature review very few articles have been published on (3S)-3beta-(3-Furyl)-4alpha-(benzoyloxy)-7alpha,5alpha-(epoxymethano)-5-methyl-3,4,5,6,7,8-hexahydro-1H-2-benzopyran-1,10-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032223512D          

 29 33  0  0  1  0            999 V2000
    2.5390    0.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6465   -0.3236    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7514   -1.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2908   -2.0618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4729   -2.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8789   -1.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561   -0.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -0.2978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3607    0.5236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880    1.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208    1.1639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652    1.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0925    2.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1698    3.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197    3.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5924    2.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    2.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5334   -0.6416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1393   -0.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1483    0.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9356    0.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4132    0.2346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210   -0.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562   -1.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1289   -1.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0516   -2.7619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168   -1.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4300   -0.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0026    0.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  2  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END


  Mrv1652309032223512D          

 29 33  0  0  1  0            999 V2000
    2.5390    0.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6465   -0.3236    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7514   -1.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2908   -2.0618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4729   -2.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8789   -1.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561   -0.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2834   -0.2978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3607    0.5236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880    1.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208    1.1639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652    1.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0925    2.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1698    3.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197    3.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5924    2.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152    2.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5334   -0.6416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1393   -0.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1483    0.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9356    0.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4132    0.2346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210   -0.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562   -1.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1289   -1.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0516   -2.7619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168   -1.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4300   -0.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0026    0.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  2  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0183019

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12C[C@@H](CC3=C1[C@@H](OC(=O)C1=CC=CC=C1)[C@@H](OC3=O)C1=COC=C1)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H18O7/c1-22-10-14(27-21(22)25)9-15-16(22)18(29-19(23)12-5-3-2-4-6-12)17(28-20(15)24)13-7-8-26-11-13/h2-8,11,14,17-18H,9-10H2,1H3/t14-,17+,18-,22-/m1/s1

> <INCHI_KEY>
VMPUNXPSXDRNOX-AQHYUZTGSA-N

> <FORMULA>
C22H18O7

> <MOLECULAR_WEIGHT>
394.379

> <EXACT_MASS>
394.10525292

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
38.127365818880804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R,4S,9R)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0^{2,7}]dodec-2(7)-en-3-yl benzoate

> <JCHEM_LOGP>
3.446900804333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.889576898473835

> <JCHEM_POLAR_SURFACE_AREA>
92.04000000000002

> <JCHEM_REFRACTIVITY>
98.7852

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,4S,9R)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0^{2,7}]dodec-2(7)-en-3-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       4.739   0.923   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.940  -0.604   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.136  -2.377   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.143  -3.849   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.616  -4.049   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.507  -2.981   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.651  -1.447   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.396  -0.556   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.540   0.977   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.284   1.869   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.226   2.173   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.428   3.402   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.173   4.294   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.317   5.827   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.717   6.469   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.973   5.577   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.828   4.044   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.996  -1.198   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.260  -0.306   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.277   1.234   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.747   1.694   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.638   0.438   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.719  -0.798   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.852  -2.731   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.107  -3.622   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.963  -5.156   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.938  -2.530   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.403  -1.086   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.471   0.023   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   28                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    8   19   24                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19                                                       
CONECT   24   18   25                                                       
CONECT   25   24    6   26                                                  
CONECT   26   25                                                            
CONECT   27    4   28                                                       
CONECT   28   27    2   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
(3S)-3b-(3-Furyl)-4a-(benzoyloxy)-7a,5a-(epoxymethano)-5-methyl-3,4,5,6,7,8-hexahydro-1H-2-benzopyran-1,10-dione	Generator
(3S)-3Β-(3-furyl)-4α-(benzoyloxy)-7α,5α-(epoxymethano)-5-methyl-3,4,5,6,7,8-hexahydro-1H-2-benzopyran-1,10-dione	Generator

Chemical Formula

C₂₂H₁₈O₇

Average Mass

394.3790 Da

Monoisotopic Mass

394.10525 Da

IUPAC Name

(1R,3R,4S,9R)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0^{2,7}]dodec-2(7)-en-3-yl benzoate

Traditional Name

(1R,3R,4S,9R)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0^{2,7}]dodec-2(7)-en-3-yl benzoate

CAS Registry Number

Not Available

SMILES

C[C@@]12C[C@@H](CC3=C1[C@@H](OC(=O)C1=CC=CC=C1)[C@@H](OC3=O)C1=COC=C1)OC2=O

InChI Identifier

InChI=1S/C22H18O7/c1-22-10-14(27-21(22)25)9-15-16(22)18(29-19(23)12-5-3-2-4-6-12)17(28-20(15)24)13-7-8-26-11-13/h2-8,11,14,17-18H,9-10H2,1H3/t14-,17+,18-,22-/m1/s1

InChI Key

VMPUNXPSXDRNOX-AQHYUZTGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Collybia maculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Dihydropyranone
Dicarboxylic acid or derivatives
Pyran
Gamma butyrolactone
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Furan
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
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	3.45	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	92.04 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.79 m³·mol⁻¹	ChemAxon
Polarizability	38.13 Å³	ChemAxon
Number of Rings	5	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

10351808

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23245776

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate (NP0183019)

MOL for NP0183019 ((1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate)

3D MOL for NP0183019 ((1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate)

3D SDF for NP0183019 ((1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate)

3D-SDF for NP0183019 ((1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate)

PDB for NP0183019 ((1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate)

3D PDB for NP0183019 ((1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate)

SMILES for NP0183019 ((1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate)

INCHI for NP0183019 ((1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate)

Structure for NP0183019 ((1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate)

3D Structure for NP0183019 ((1r,3r,4s,9r)-4-(furan-3-yl)-1-methyl-6,11-dioxo-5,10-dioxatricyclo[7.2.1.0²,⁷]dodec-2(7)-en-3-yl benzoate)