NP-MRD: Showing NP-Card for 3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide (NP0050200)

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Record Information

Version

2.0

Created at

2022-04-27 20:45:37 UTC

Updated at

2022-04-27 20:45:37 UTC

NP-MRD ID

NP0050200

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide

Description

(9S,11aR)-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-2H,4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl acetate 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. 3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide is found in Pentzia eenii. Based on a literature review very few articles have been published on (9S,11aR)-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-2H,4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222452D          

 22 23  0  0  1  0            999 V2000
    3.1925   -1.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697   -1.9226    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8556   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502   -0.8834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4589   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652   -0.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832   -0.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551   -1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061   -1.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808    0.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6963    0.3695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817    0.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393   -1.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3328   -2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9610   -2.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7751   -2.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2979   -2.1899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0664   -3.5999    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  2  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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  1  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  1 16  1  0  0  0  0
 15 17  1  0  0  0  0
  3 18  1  0  0  0  0
  2 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050200

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C\C=C(C)\CCC2=C(CO)C(=O)O[C@@H]2\C=C1/C

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-10-4-6-13-14(9-18)17(20)22-16(13)8-11(2)15(7-5-10)21-12(3)19/h5,8,15-16,18H,4,6-7,9H2,1-3H3/b10-5+,11-8+/t15-,16+/m0/s1

> <INCHI_KEY>
KHGWZYVQWFPLPX-JBYUELLOSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.358

> <EXACT_MASS>
306.146723808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.421127206231205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S,11aR)-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-2H,4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl acetate

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
1.7220720683333335

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.96511073550371

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.242495816043395

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8601246924380668

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
83.117

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S,11aR)-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl acetate

> <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       5.959  -2.397   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.983  -3.589   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.464  -3.339   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.920  -1.898   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.400  -1.649   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.857  -0.208   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.682  -0.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.089  -1.765   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.529  -2.309   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.198  -2.611   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.644   0.922   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.166   0.690   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.832   0.983   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.352   0.734   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.896  -0.707   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.416  -0.957   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.807  -2.245   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.488  -4.531   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.527  -5.030   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.047  -5.279   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.023  -4.088   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.591  -6.720   0.000  0.00  0.00           C+0
CONECT    1    2   16                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    5                                                       
CONECT   11    7   12                                                       
CONECT   12   11                                                            
CONECT   13    6   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15    1                                                       
CONECT   17   15                                                            
CONECT   18    3                                                            
CONECT   19    2   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
(9S,11AR)-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-2H,4H,5H,8H,9H,11ah-cyclodeca[b]furan-9-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₅

Average Mass

306.3580 Da

Monoisotopic Mass

306.14672 Da

IUPAC Name

(9S,11aR)-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-2H,4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl acetate

Traditional Name

(9S,11aR)-3-(hydroxymethyl)-6,10-dimethyl-2-oxo-4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C\C=C(C)\CCC2=C(CO)C(=O)O[C@@H]2\C=C1/C

InChI Identifier

InChI=1S/C17H22O5/c1-10-4-6-13-14(9-18)17(20)22-16(13)8-11(2)15(7-5-10)21-12(3)19/h5,8,15-16,18H,4,6-7,9H2,1-3H3/b10-5+,11-8+/t15-,16+/m0/s1

InChI Key

KHGWZYVQWFPLPX-JBYUELLOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pentzia eenii	Plant	KNApSAcK

Chemical Taxonomy

Description

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
Sesquiterpenoid
Germacrane sesquiterpenoid
Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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	2.45	ALOGPS
logP	1.72	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.24	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.12 m³·mol⁻¹	ChemAxon
Polarizability	31.42 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

14466127

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide (NP0050200)

MOL for NP0050200 (3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide)

3D MOL for NP0050200 (3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide)

3D SDF for NP0050200 (3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide)

3D-SDF for NP0050200 (3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide)

PDB for NP0050200 (3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide)

3D PDB for NP0050200 (3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide)

SMILES for NP0050200 (3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide)

INCHI for NP0050200 (3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide)

Structure for NP0050200 (3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide)

3D Structure for NP0050200 (3-Acetoxy-13-hydroxy-1(10),4,7(11)-germacratrien-12,6-olide)