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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:54:33 UTC

Update Date

2022-09-22 18:34:53 UTC

HMDB ID

HMDB0341395

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Solstitialin A 13-acetic acid

Description

24470-33-5 belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 24470-33-5 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004181501132D          

 23 25  0  0  0  0            999 V2000
    1.3481    2.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7604    1.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349    1.8059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9680    0.7879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803    0.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878   -0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2280   -0.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602   -0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871    0.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754    1.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140   -0.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864   -0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -1.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944   -1.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541   -1.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -2.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -1.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -1.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202   -1.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341395

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCC1(O)C2CCC(=C)C3CC(O)C(=C)C3C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O6/c1-8-4-5-12-15(14-9(2)13(19)6-11(8)14)23-16(20)17(12,21)7-22-10(3)18/h11-15,19,21H,1-2,4-7H2,3H3

> <INCHI_KEY>
XIVYFPUTCCJWCJ-UHFFFAOYSA-N

> <FORMULA>
C17H22O6

> <MOLECULAR_WEIGHT>
322.357

> <EXACT_MASS>
322.141638428

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.221339306225474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{3,8-dihydroxy-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-3-yl}methyl acetate

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
0.15727530366666687

> <ALOGPS_LOGS>
-1.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.600267569828162

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.327245198384656

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9737452639536404

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
79.9109

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{3,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-3-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       2.516   4.042   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.419   2.961   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.065   3.371   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.807   1.471   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.710   0.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.097  -1.100   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.426  -1.330   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.539  -0.559   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.882   0.942   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.269   1.610   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.657   0.942   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.861   1.902   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.999  -0.559   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.441  -1.100   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.372  -2.639   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.576  -3.599   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.888  -3.049   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.346  -4.490   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.039  -1.763   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.499  -1.763   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.651  -3.049   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.166  -2.639   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.038  -3.599   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   22                                             
CONECT    7    6                                                            
CONECT    8    6    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13   20                                                  
CONECT   20   19    8   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    6   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Solstitialin a 13-acetate	MeSH
{3,8-dihydroxy-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-3-yl}methyl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₆

Average Molecular Weight

322.357

Monoisotopic Molecular Weight

322.141638428

IUPAC Name

{3,8-dihydroxy-6,9-dimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-3-yl}methyl acetate

Traditional Name

{3,8-dihydroxy-6,9-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-3-yl}methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1(O)C2CCC(=C)C3CC(O)C(=C)C3C2OC1=O

InChI Identifier

InChI=1S/C17H22O6/c1-8-4-5-12-15(14-9(2)13(19)6-11(8)14)23-16(20)17(12,21)7-22-10(3)18/h11-15,19,21H,1-2,4-7H2,3H3

InChI Key

XIVYFPUTCCJWCJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.52	ALOGPS
logP	0.16	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	11.33	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.91 m³·mol⁻¹	ChemAxon
Polarizability	33.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Retention Times

Not Available

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

434576

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for Solstitialin A 13-acetic acid (HMDB0341395)

MOL for HMDB0341395 (Solstitialin A 13-acetic acid)

3D MOL for HMDB0341395 (Solstitialin A 13-acetic acid)

3D SDF for HMDB0341395 (Solstitialin A 13-acetic acid)

3D-SDF for HMDB0341395 (Solstitialin A 13-acetic acid)

PDB for HMDB0341395 (Solstitialin A 13-acetic acid)

3D PDB for HMDB0341395 (Solstitialin A 13-acetic acid)

SMILES for HMDB0341395 (Solstitialin A 13-acetic acid)

INCHI for HMDB0341395 (Solstitialin A 13-acetic acid)

Structure for HMDB0341395 (Solstitialin A 13-acetic acid)

3D Structure for HMDB0341395 (Solstitialin A 13-acetic acid)

Predicted Retention Times

Predicted Kovats Retention Indices