NP-MRD: Showing NP-Card for 8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide (NP0335409)

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Record Information

Version

2.0

Created at

2024-09-11 01:28:57 UTC

Updated at

2024-09-11 01:28:58 UTC

NP-MRD ID

NP0335409

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide

Description

8Beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review very few articles have been published on 8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262304012D          

 30 31  0  0  0  0            999 V2000
    1.1813   -1.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3021   -1.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1377   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6867   -0.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3021    0.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7967    1.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207    1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5107   -0.1101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854   -0.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7306   -1.0437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5768   -2.4171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3460   -2.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6094   -1.2085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5216   -1.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7415   -2.6370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6207   -2.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7745    1.1537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6094    0.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1809    0.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5216    0.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5216    1.8130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3021    2.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    2.8569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1700    0.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152   -0.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999   -0.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7745   -0.2201    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
  2 11  1  0  0  0  0
  2 16  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5 23  1  0  0  0  0
  6  7  2  0  0  0  0
  6 25  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 28  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
M  END


  Mrv2104 05262304012D          

 30 31  0  0  0  0            999 V2000
    1.1813   -1.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3021   -1.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1377   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6867   -0.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3021    0.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7967    1.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207    1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5107   -0.1101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854   -0.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7306   -1.0437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5768   -2.4171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3460   -2.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6094   -1.2085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5216   -1.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7415   -2.6370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6207   -2.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7745    1.1537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6094    0.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1809    0.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5216    0.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5216    1.8130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3021    2.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5220    2.8569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1700    0.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1152   -0.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999   -0.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7745   -0.2201    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
  2 11  1  0  0  0  0
  2 16  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5 23  1  0  0  0  0
  6  7  2  0  0  0  0
  6 25  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 28  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335409

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC(=O)C(CO)CC2OC(=O)C(=C)C2C(CC1(C)OC)OC(=O)C(\C)=C\C

> <INCHI_IDENTIFIER>
InChI=1/C22H32O8/c1-7-12(2)20(25)30-17-10-22(4,28-6)18(27-5)9-15(24)14(11-23)8-16-19(17)13(3)21(26)29-16/h7,14,16-19,23H,3,8-11H2,1-2,4-6H3/b12-7+

> <INCHI_KEY>
LOQBOYSPYWSYGO-KPKJPENVNA-N

> <FORMULA>
C22H32O8

> <MOLECULAR_WEIGHT>
424.49

> <EXACT_MASS>
424.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.893034058920236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-dodecahydrocyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
2.0364737833333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.05754642811784

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.310836227386584

> <JCHEM_PKA_STRONGEST_BASIC>
-2.662786412852663

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
108.66829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       2.205  -2.768   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -2.974   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.257  -1.436   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.282  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564   1.333   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.487   2.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.025   2.666   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.820  -0.206   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.333  -0.923   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.230  -1.948   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.077  -4.512   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.513  -5.333   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.871  -2.256   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.333  -1.538   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.102  -2.461   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.974  -3.384   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.384  -4.922   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.025  -4.922   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.179   2.154   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.871   0.615   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.333  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.204   1.025   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.974   1.743   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.974   3.384   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.564   3.897   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.974   5.333   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.051   0.821   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.948  -0.308   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.666  -0.923   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.179  -0.411   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11   16                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6   23                                                  
CONECT    6    5    7   25                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   28                                                  
CONECT   10    9                                                            
CONECT   11    2   12                                                       
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16    2   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   20                                                            
CONECT   20   19   21                                                       
CONECT   21   14   20   22                                                  
CONECT   22   21   23                                                       
CONECT   23    5   22   24                                                  
CONECT   24   23   25                                                       
CONECT   25    6   24   26                                                  
CONECT   26   25                                                            
CONECT   27   28                                                            
CONECT   28    9   27   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
8b-Angeloyloxy-15-hydroxy-1a,10R-dimethoxy-3-oxo-11(13)-germacren-12,6a-olide	Generator
8Β-angeloyloxy-15-hydroxy-1α,10R-dimethoxy-3-oxo-11(13)-germacren-12,6α-olide	Generator

Chemical Formula

C₂₂H₃₂O₈

Average Mass

424.4900 Da

Monoisotopic Mass

424.20972 Da

IUPAC Name

10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-dodecahydrocyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate

Traditional Name

10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC1CC(=O)C(CO)CC2OC(=O)C(=C)C2C(CC1(C)OC)OC(=O)C(\C)=C\C

InChI Identifier

InChI=1/C22H32O8/c1-7-12(2)20(25)30-17-10-22(4,28-6)18(27-5)9-15(24)14(11-23)8-16-19(17)13(3)21(26)29-16/h7,14,16-19,23H,3,8-11H2,1-2,4-6H3/b12-7+

InChI Key

LOQBOYSPYWSYGO-KPKJPENVNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Fatty acid ester
Cyclitol or derivatives
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Cyclic ketone
Carboxylic acid ester
Lactone
Ketone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Alcohol
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	2.04	ChemAxon
pKa (Strongest Acidic)	15.31	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.67 m³·mol⁻¹	ChemAxon
Polarizability	43.89 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide (NP0335409)

MOL for NP0335409 (8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide)

3D MOL for NP0335409 (8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide)

3D SDF for NP0335409 (8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide)

3D-SDF for NP0335409 (8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide)

PDB for NP0335409 (8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide)

3D PDB for NP0335409 (8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide)

SMILES for NP0335409 (8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide)

INCHI for NP0335409 (8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide)

Structure for NP0335409 (8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide)

3D Structure for NP0335409 (8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide)