NP-MRD: Showing NP-Card for 5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate (NP0274300)

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Record Information

Version

2.0

Created at

2022-09-08 21:38:38 UTC

Updated at

2022-09-08 21:38:38 UTC

NP-MRD ID

NP0274300

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate

Description

5-(Furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]Dodecan]-1'(12')-en-10'-yl acetate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate is found in Teucrium webbianum. 5-(Furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]Dodecan]-1'(12')-en-10'-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241516062D          

 28 32  0  0  0  0            999 V2000
    2.9374   -1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3678   -0.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5662   -0.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966   -0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1719   -0.1670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1057    0.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974    0.8419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474    1.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286    0.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0303    0.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0346    1.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534    2.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6098    1.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4158    3.1166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7345    3.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7969    4.4045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091    3.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9134    1.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360    0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309    0.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2287   -0.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4236   -1.0889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2700    1.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0752    2.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7774    2.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4062    2.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0927    1.5139    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  2  0  0  0  0
 20 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  2  0  0  0  0
 24 28  1  0  0  0  0
M  END


  Mrv1533004241516062D          

 28 32  0  0  0  0            999 V2000
    2.9374   -1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3678   -0.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5662   -0.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966   -0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1719   -0.1670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1057    0.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974    0.8419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474    1.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286    0.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0303    0.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0346    1.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534    2.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6098    1.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4158    3.1166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7345    3.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7969    4.4045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091    3.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9134    1.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360    0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309    0.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2287   -0.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4236   -1.0889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2700    1.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0752    2.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7774    2.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4062    2.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0927    1.5139    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  2  0  0  0  0
 20 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  2  0  0  0  0
 24 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0274300

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2OC(=O)C3=C2C(CC(C3)OC(C)=O)C11CC(OC1=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O7/c1-10-5-16-18-14(19(23)27-16)6-13(26-11(2)22)7-15(18)21(10)8-17(28-20(21)24)12-3-4-25-9-12/h3-4,9-10,13,15-17H,5-8H2,1-2H3

> <INCHI_KEY>
GMHUPLXKKUACIO-UHFFFAOYSA-N

> <FORMULA>
C21H22O7

> <MOLECULAR_WEIGHT>
386.4

> <EXACT_MASS>
386.136553048

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.60871005781748

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
2.0803610660000005

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.220211492124182

> <JCHEM_PKA_STRONGEST_BASIC>
-2.888539787297253

> <JCHEM_POLAR_SURFACE_AREA>
92.04

> <JCHEM_REFRACTIVITY>
94.9197

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       5.483  -2.131   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.420  -1.017   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.924  -1.381   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.860  -0.267   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.321  -0.312   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.197   1.138   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.675   1.572   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.022   2.079   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.293   1.211   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.790   1.575   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.798   3.413   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.526   4.282   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.138   3.615   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.643   5.818   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.371   6.686   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.488   8.222   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.017   6.019   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.853   0.461   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.438   1.885   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.974   1.769   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.338   0.272   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.027  -0.536   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.391  -2.033   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.971   2.942   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.607   4.439   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.918   5.247   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.092   4.250   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.506   2.826   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   10    2   19   22                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   18   23                                                  
CONECT   23   22                                                            
CONECT   24   20   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Value	Source
5-(Furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0,]dodecan]-1'(12')-en-10'-yl acetic acid	Generator
5-(Furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetic acid	Generator

Chemical Formula

C₂₁H₂₂O₇

Average Mass

386.4000 Da

Monoisotopic Mass

386.13655 Da

IUPAC Name

5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate

Traditional Name

5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate

CAS Registry Number

Not Available

SMILES

CC1CC2OC(=O)C3=C2C(CC(C3)OC(C)=O)C11CC(OC1=O)C1=COC=C1

InChI Identifier

InChI=1S/C21H22O7/c1-10-5-16-18-14(19(23)27-16)6-13(26-11(2)22)7-15(18)21(10)8-17(28-20(21)24)12-3-4-25-9-12/h3-4,9-10,13,15-17H,5-8H2,1-2H3

InChI Key

GMHUPLXKKUACIO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Teucrium webbianum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
2-furanone
Gamma butyrolactone
Dihydrofuran
Furan
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen 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	2.18	ALOGPS
logP	2.08	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.22	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	3	ChemAxon
Refractivity	94.92 m³·mol⁻¹	ChemAxon
Polarizability	38.61 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate (NP0274300)

MOL for NP0274300 (5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate)

3D MOL for NP0274300 (5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate)

3D SDF for NP0274300 (5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate)

3D-SDF for NP0274300 (5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate)

PDB for NP0274300 (5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate)

3D PDB for NP0274300 (5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate)

SMILES for NP0274300 (5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate)

INCHI for NP0274300 (5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate)

Structure for NP0274300 (5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate)

3D Structure for NP0274300 (5-(furan-3-yl)-6'-methyl-2,2'-dioxo-3'-oxaspiro[oxolane-3,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-1'(12')-en-10'-yl acetate)