NP-MRD: Showing NP-Card for [(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate (NP0245326)

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Record Information

Version

2.0

Created at

2022-09-07 06:22:05 UTC

Updated at

2022-09-07 06:22:05 UTC

NP-MRD ID

NP0245326

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate

Description

[(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate is found in Melampodium linearilobum. Based on a literature review very few articles have been published on Linearilobin E.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072208222D          

 28 29  0  0  1  0            999 V2000
    0.4566    3.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9415    2.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    3.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3577    1.7927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    1.1119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8862    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2364    0.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433    0.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186    0.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5870    0.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9800    1.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5484    2.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2763    2.1332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7079    2.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5326    2.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148    3.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8047    1.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1978    2.1999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9218    2.9774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5759    3.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5536    4.3048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    3.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0336    3.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225    2.2222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4541    1.5191    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2788    1.5414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0611    0.7938    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 12 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25 23  1  6  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
  8 28  1  0  0  0  0
M  END


  Mrv1652309072208222D          

 28 29  0  0  1  0            999 V2000
    0.4566    3.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9415    2.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    3.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4670    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3577    1.7927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    1.1119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8862    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2364    0.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433    0.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186    0.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5870    0.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9800    1.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5484    2.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2763    2.1332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7079    2.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5326    2.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148    3.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8047    1.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1978    2.1999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9218    2.9774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5759    3.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5536    4.3048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    3.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0336    3.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225    2.2222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4541    1.5191    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2788    1.5414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0611    0.7938    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 12 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25 23  1  6  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
  8 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245326

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC\C1=C/[C@H]2OC(=O)C(=C)[C@@H]2[C@H](O)C\C(COC(=O)C(C)=C)=C\CC1

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O7/c1-12(2)20(24)27-11-15-6-5-7-16(10-26-14(4)22)9-18-19(17(23)8-15)13(3)21(25)28-18/h6,9,17-19,23H,1,3,5,7-8,10-11H2,2,4H3/b15-6-,16-9-/t17-,18-,19-/m1/s1

> <INCHI_KEY>
QZSVNNCXCGAUDT-MANFWZSISA-N

> <FORMULA>
C21H26O7

> <MOLECULAR_WEIGHT>
390.432

> <EXACT_MASS>
390.167853177

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.56504590156865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3aR,4R,11aR)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate

> <JCHEM_LOGP>
2.176890183666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.699099714938047

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9304137846860945

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
102.37429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(3aR,4R,11aR)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.852   6.623   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.757   5.377   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.865   5.640   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.872   3.388   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.668   3.346   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.677   2.076   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.521   3.388   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.175   1.440   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.441   0.086   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.901   0.045   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.096   1.357   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.829   2.711   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.024   4.023   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.516   3.982   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.321   5.294   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.861   5.253   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.588   6.648   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.369   2.753   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.103   4.107   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.587   5.558   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.808   6.496   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.767   8.036   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.078   5.625   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.529   6.140   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.642   4.148   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.448   2.836   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.987   2.877   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.714   1.482   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   19   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    8                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆O₇

Average Mass

390.4320 Da

Monoisotopic Mass

390.16785 Da

IUPAC Name

[(3aR,4R,11aR)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate

Traditional Name

[(3aR,4R,11aR)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC\C1=C/[C@H]2OC(=O)C(=C)[C@@H]2[C@H](O)C\C(COC(=O)C(C)=C)=C\CC1

InChI Identifier

InChI=1S/C21H26O7/c1-12(2)20(24)27-11-15-6-5-7-16(10-26-14(4)22)9-18-19(17(23)8-15)13(3)21(25)28-18/h6,9,17-19,23H,1,3,5,7-8,10-11H2,2,4H3/b15-6-,16-9-/t17-,18-,19-/m1/s1

InChI Key

QZSVNNCXCGAUDT-MANFWZSISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melampodium linearilobum	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	ChemAxon
pKa (Strongest Acidic)	14.7	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	102.37 m³·mol⁻¹	ChemAxon
Polarizability	40.57 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

C00012275

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

102117137

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate (NP0245326)

MOL for NP0245326 ([(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate)

3D MOL for NP0245326 ([(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate)

3D SDF for NP0245326 ([(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate)

3D-SDF for NP0245326 ([(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate)

PDB for NP0245326 ([(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate)

3D PDB for NP0245326 ([(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate)

SMILES for NP0245326 ([(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate)

INCHI for NP0245326 ([(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate)

Structure for NP0245326 ([(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate)

3D Structure for NP0245326 ([(3ar,4r,11ar)-10-[(acetyloxy)methyl]-4-hydroxy-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-yl]methyl 2-methylprop-2-enoate)