NP-MRD: Showing NP-Card for 1(10)E,8E-Millerdienolide (NP0050209)

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Record Information

Version

2.0

Created at

2022-04-27 20:48:13 UTC

Updated at

2022-04-27 20:48:13 UTC

NP-MRD ID

NP0050209

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1(10)E,8E-Millerdienolide

Description

(3AS,11S,11aS)-6-formyl-11-hydroxy-3,10-dimethylidene-2-oxo-2H,3H,3aH,8H,9H,10H,11H,11aH-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 1(10)E,8E-Millerdienolide is found in Milleria quinqueflora. Based on a literature review very few articles have been published on (3aS,11S,11aS)-6-formyl-11-hydroxy-3,10-dimethylidene-2-oxo-2H,3H,3aH,8H,9H,10H,11H,11aH-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222482D          

 25 26  0  0  1  0            999 V2000
    5.7288    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2137    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2137   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7288   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9441   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9441   -1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1595   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6746    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6746    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1595    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9441    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102    2.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252    3.5810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8306    2.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662    3.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3156    2.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6350    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5801    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2137    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781    2.9136    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  1 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  9 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  8 22  1  1  0  0  0
  7 23  1  6  0  0  0
  1 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050209

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C(=O)O\C1=C\C(\C=O)=C/CCC(=C)[C@H](O)[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O6/c1-10(2)18(22)24-14-8-13(9-20)7-5-6-11(3)16(21)17-15(14)12(4)19(23)25-17/h7-9,15-17,21H,1,3-6H2,2H3/b13-7+,14-8+/t15-,16+,17+/m1/s1

> <INCHI_KEY>
MFFGLCYYMGFWST-UXYUZHAGSA-N

> <FORMULA>
C19H20O6

> <MOLECULAR_WEIGHT>
344.363

> <EXACT_MASS>
344.125988364

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.89800276259473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,11S,11aS)-6-formyl-11-hydroxy-3,10-dimethylidene-2-oxo-2H,3H,3aH,8H,9H,10H,11H,11aH-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.981156893666666

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.906147836454775

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.663970136503996

> <JCHEM_PKA_STRONGEST_BASIC>
-3.423861569258107

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
92.24759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,11S,11aS)-6-formyl-11-hydroxy-3,10-dimethylidene-2-oxo-3aH,8H,9H,11H,11aH-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      10.694   2.786   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.599   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.599  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.694  -1.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.229  -1.722   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.229  -3.262   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.764  -1.246   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.859   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.859   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.764   2.786   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.229   3.262   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.859   4.032   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.486   5.439   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.580   6.685   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.017   5.600   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.644   7.006   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.922   4.354   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.395   2.016   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.919   3.481   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.489   0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.949   0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.395  -0.476   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.859  -2.492   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.599   4.032   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.973   5.439   0.000  0.00  0.00           O+0
CONECT    1    2   11   24                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   23                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    1                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    9   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    8                                                       
CONECT   23    7                                                            
CONECT   24    1   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
(3AS,11S,11as)-6-formyl-11-hydroxy-3,10-dimethylidene-2-oxo-2H,3H,3ah,8H,9H,10H,11H,11ah-cyclodeca[b]furan-4-yl 2-methylprop-2-enoic acid	Generator

Chemical Formula

C₁₉H₂₀O₆

Average Mass

344.3630 Da

Monoisotopic Mass

344.12599 Da

IUPAC Name

(3aS,11S,11aS)-6-formyl-11-hydroxy-3,10-dimethylidene-2-oxo-2H,3H,3aH,8H,9H,10H,11H,11aH-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

Traditional Name

(3aS,11S,11aS)-6-formyl-11-hydroxy-3,10-dimethylidene-2-oxo-3aH,8H,9H,11H,11aH-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=C)C(=O)O\C1=C\C(\C=O)=C/CCC(=C)[C@H](O)[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C19H20O6/c1-10(2)18(22)24-14-8-13(9-20)7-5-6-11(3)16(21)17-15(14)12(4)19(23)25-17/h7-9,15-17,21H,1,3-6H2,2H3/b13-7+,14-8+/t15-,16+,17+/m1/s1

InChI Key

MFFGLCYYMGFWST-UXYUZHAGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Milleria quinqueflora	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Germacrane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Enol ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Aldehyde
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
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	1.67	ALOGPS
logP	1.98	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.66	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.25 m³·mol⁻¹	ChemAxon
Polarizability	33.9 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

163046813

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1(10)E,8E-Millerdienolide (NP0050209)

MOL for NP0050209 (1(10)E,8E-Millerdienolide)

3D MOL for NP0050209 (1(10)E,8E-Millerdienolide)

3D SDF for NP0050209 (1(10)E,8E-Millerdienolide)

3D-SDF for NP0050209 (1(10)E,8E-Millerdienolide)

PDB for NP0050209 (1(10)E,8E-Millerdienolide)

3D PDB for NP0050209 (1(10)E,8E-Millerdienolide)

SMILES for NP0050209 (1(10)E,8E-Millerdienolide)

INCHI for NP0050209 (1(10)E,8E-Millerdienolide)

Structure for NP0050209 (1(10)E,8E-Millerdienolide)

3D Structure for NP0050209 (1(10)E,8E-Millerdienolide)