NP-MRD: Showing NP-Card for 18-Acetoxy-6-oxogrindelic acid (NP0065179)

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Record Information

Version

1.0

Created at

2022-04-28 09:26:12 UTC

Updated at

2022-04-28 09:26:12 UTC

NP-MRD ID

NP0065179

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18-Acetoxy-6-oxogrindelic acid

Description

(2R,5S)-4,4'aalpha,5,5',6',7',8',8'a-Octahydro-5'alpha-(hydroxymethyl)-2',5,5',8'abeta-tetramethyl-4'-oxospiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 18-Acetoxy-6-oxogrindelic acid is found in Grindelia hirsutula and Grindelia stricta. It was first documented in 2022 (PMID: 35487686). Based on a literature review a significant number of articles have been published on (2R,5S)-4,4'aalpha,5,5',6',7',8',8'a-Octahydro-5'alpha-(hydroxymethyl)-2',5,5',8'abeta-tetramethyl-4'-oxospiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetic acid (PMID: 35487685) (PMID: 35487684) (PMID: 35487683) (PMID: 35487682).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282211262D          

 25 27  0  0  1  0            999 V2000
    1.6704    0.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2728    0.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0857    1.7396    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2964    1.9794    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6940    1.4157    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8811    0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954    1.6554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2824    2.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3199    3.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1093    2.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7117    3.3467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    2.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0066    0.8368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7404    0.4868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3042    1.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9055    1.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4786   -0.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2740   -0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0857    0.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3639    0.7817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -0.6243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2953    0.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8822    1.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667    1.3723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3529    2.5202    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  4 10  1  1  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
  7 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 14 17  1  1  0  0  0
 14 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  5 22  1  1  0  0  0
  3 23  1  6  0  0  0
 23 24  1  0  0  0  0
  3 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0065179

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)[C@H]2[C@](C)(CO)CCC[C@]2(C)[C@@]11CC[C@@](C)(CC(O)=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c1-13-10-14(22)16-17(2,12-21)6-5-7-19(16,4)20(13)9-8-18(3,25-20)11-15(23)24/h10,16,21H,5-9,11-12H2,1-4H3,(H,23,24)/t16-,17-,18-,19-,20+/m0/s1

> <INCHI_KEY>
YKJKZQHYTCDZKN-VYJAJWGXSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.455

> <EXACT_MASS>
350.209324066

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.964639445147526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,4aS,5R,5'S,8aS)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4-oxo-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-yl]acetic acid

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
2.5442668676666664

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.092423201849478

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.498191176396872

> <JCHEM_PKA_STRONGEST_BASIC>
-2.758336468830457

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
94.05479999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aS,5R,5'S,8aS)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolane]-5'-ylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.118   0.695   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.243   1.747   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.893   3.247   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.420   3.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.295   2.643   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.645   1.143   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.178   3.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.527   4.590   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.597   5.642   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.071   5.195   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.195   6.247   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.001   5.038   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.012   1.562   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.382   0.909   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.434   2.033   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.690   3.381   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.893  -0.552   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.378  -0.266   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.893   0.009   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.413   1.459   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.889  -1.165   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.551   1.294   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.380   3.649   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.471   2.562   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.392   4.704   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   23   25                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   22                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   13   16                                             
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8                                                            
CONECT   13    7   14                                                       
CONECT   14   13   15   17   18                                             
CONECT   15   14   16                                                       
CONECT   16   15    7                                                       
CONECT   17   14                                                            
CONECT   18   14   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    5                                                            
CONECT   23    3   24                                                       
CONECT   24   23                                                            
CONECT   25    3                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
(2R,5S)-4,4'Aalpha,5,5',6',7',8',8'a-octahydro-5'a-(hydroxymethyl)-2',5,5',8'abeta-tetramethyl-4'-oxospiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetate	Generator
(2R,5S)-4,4'Aalpha,5,5',6',7',8',8'a-octahydro-5'a-(hydroxymethyl)-2',5,5',8'abeta-tetramethyl-4'-oxospiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetic acid	Generator
(2R,5S)-4,4'Aalpha,5,5',6',7',8',8'a-octahydro-5'alpha-(hydroxymethyl)-2',5,5',8'abeta-tetramethyl-4'-oxospiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetate	Generator
(2R,5S)-4,4'Aalpha,5,5',6',7',8',8'a-octahydro-5'α-(hydroxymethyl)-2',5,5',8'abeta-tetramethyl-4'-oxospiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetate	Generator
(2R,5S)-4,4'Aalpha,5,5',6',7',8',8'a-octahydro-5'α-(hydroxymethyl)-2',5,5',8'abeta-tetramethyl-4'-oxospiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetic acid	Generator

Chemical Formula

C₂₀H₃₀O₅

Average Mass

350.4550 Da

Monoisotopic Mass

350.20932 Da

IUPAC Name

2-[(1R,4aS,5R,5'S,8aS)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4-oxo-4a,5,6,7,8,8a-hexahydro-4H-spiro[naphthalene-1,2'-oxolane]-5'-yl]acetic acid

Traditional Name

(1R,4aS,5R,5'S,8aS)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydrospiro[naphthalene-1,2'-oxolane]-5'-ylacetic acid

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)[C@H]2[C@](C)(CO)CCC[C@]2(C)[C@@]11CC[C@@](C)(CC(O)=O)O1

InChI Identifier

InChI=1S/C20H30O5/c1-13-10-14(22)16-17(2,12-21)6-5-7-19(16,4)20(13)9-8-18(3,25-20)11-15(23)24/h10,16,21H,5-9,11-12H2,1-4H3,(H,23,24)/t16-,17-,18-,19-,20+/m0/s1

InChI Key

YKJKZQHYTCDZKN-VYJAJWGXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Grindelia hirsutula	LOTUS Database	35616633
Grindelia stricta	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Grindelane diterpenoid
Abscisic acid
Cyclohexenone
Oxolane
Ketone
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Primary 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	2.18	ALOGPS
logP	2.54	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.5	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.05 m³·mol⁻¹	ChemAxon
Polarizability	37.96 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

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

8673459

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10498058

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ridge KM, Eriksson JE, Pekny M, Goldman RD: Roles of vimentin in health and disease. Genes Dev. 2022 Apr 1;36(7-8):391-407. doi: 10.1101/gad.349358.122. [PubMed:35487686 ]
Comabella M, Sastre-Garriga J, Carbonell-Mirabent P, Fissolo N, Tur C, Malhotra S, Pareto D, Aymerich FX, Rio J, Rovira A, Tintore M, Montalban X: Serum neurofilament light chain levels predict long-term disability progression in patients with progressive multiple sclerosis. J Neurol Neurosurg Psychiatry. 2022 Apr 29. pii: jnnp-2022-329020. doi: 10.1136/jnnp-2022-329020. [PubMed:35487685 ]
Wezenbeek E, Denolf S, Willems TM, Pieters D, Bourgois JG, Philippaerts RM, De Winne B, Wieme M, Van Hecke R, Markey L, Schuermans J, Witvrouw E, Verstockt S: Association between SARS-COV-2 infection and muscle strain injury occurrence in elite male football players: a prospective study of 29 weeks including three teams from the Belgian professional football league. Br J Sports Med. 2022 Apr 29. pii: bjsports-2021-104595. doi: 10.1136/bjsports-2021-104595. [PubMed:35487684 ]
Wagner JL, Smith KJ, Johnson C, Hilaire ML, Medina MS: Best Practices in Syllabus Design. Am J Pharm Educ. 2022 Apr 29:8995. doi: 10.5688/ajpe8995. [PubMed:35487683 ]
Ahlvik-Harju C: Finding more constructive ways forward in the debate over vaccines with increased disability cultural competence. Med Humanit. 2022 Apr 29. pii: medhum-2021-012342. doi: 10.1136/medhum-2021-012342. [PubMed:35487682 ]

Showing NP-Card for 18-Acetoxy-6-oxogrindelic acid (NP0065179)

MOL for NP0065179 (18-Acetoxy-6-oxogrindelic acid)

3D MOL for NP0065179 (18-Acetoxy-6-oxogrindelic acid)

3D SDF for NP0065179 (18-Acetoxy-6-oxogrindelic acid)

3D-SDF for NP0065179 (18-Acetoxy-6-oxogrindelic acid)

PDB for NP0065179 (18-Acetoxy-6-oxogrindelic acid)

3D PDB for NP0065179 (18-Acetoxy-6-oxogrindelic acid)

SMILES for NP0065179 (18-Acetoxy-6-oxogrindelic acid)

INCHI for NP0065179 (18-Acetoxy-6-oxogrindelic acid)

Structure for NP0065179 (18-Acetoxy-6-oxogrindelic acid)

3D Structure for NP0065179 (18-Acetoxy-6-oxogrindelic acid)