NP-MRD: Showing NP-Card for (1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid (NP0330391)

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Record Information

Version

2.0

Created at

2022-09-12 15:42:01 UTC

Updated at

2022-09-12 15:42:01 UTC

NP-MRD ID

NP0330391

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid

Description

19-Hydroxygrindelic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid was first documented in 2017 (PMID: 28135782). Based on a literature review very few articles have been published on 19-Hydroxygrindelic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122217422D          

 24 26  0  0  1  0            999 V2000
    2.2871    1.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765    1.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6789    1.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4683    1.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6553    0.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447    0.5021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5437    1.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2685    0.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6417    1.2826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6317   -0.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0294   -0.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2400   -0.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0530    0.1782    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6543   -0.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2636    0.4179    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3656   -0.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6185   -0.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548   -0.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3781    0.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5147   -0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045   -0.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1644   -1.2397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4345    0.1635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4534    0.5739    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  1  0  0  0
  8  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  2 15  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
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 18 24  1  0  0  0  0
 15 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0330391

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC2[C@@](C)(CO)CCC[C@]2(C)[C@@]11CCC(C)(CC(O)=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-14-6-7-15-17(2,13-21)8-5-9-19(15,4)20(14)11-10-18(3,24-20)12-16(22)23/h6,15,21H,5,7-13H2,1-4H3,(H,22,23)/t15?,17-,18?,19+,20-/m1/s1

> <INCHI_KEY>
DJSOIWVYQLXAFK-IIJMLMANSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
37.87587436605581

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.107772264666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.652022843695658

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6886908050465514

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2010131149815058

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
93.41079999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       4.269   2.728   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.743   2.280   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.867   3.332   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.341   2.885   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.690   1.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.163   0.937   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.348   2.466   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.701   1.021   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.398   2.394   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.513  -0.563   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.388  -1.615   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.915  -1.167   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.566   0.333   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.821  -1.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.092   0.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.282  -0.748   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.888  -1.401   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.836  -0.277   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.572   0.604   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.827  -1.441   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.315  -1.150   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.307  -2.314   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.811   0.305   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.580   1.071   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    8   10                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13    2   16   24                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   24                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   18   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
19-Hydroxygrindelate	Generator

Chemical Formula

C₂₀H₃₂O₄

Average Mass

336.4720 Da

Monoisotopic Mass

336.23006 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC1=CCC2[C@@](C)(CO)CCC[C@]2(C)[C@@]11CCC(C)(CC(O)=O)O1

InChI Identifier

InChI=1S/C20H32O4/c1-14-6-7-15-17(2,13-21)8-5-9-19(15,4)20(14)11-10-18(3,24-20)12-16(22)23/h6,15,21H,5,7-13H2,1-4H3,(H,22,23)/t15?,17-,18?,19+,20-/m1/s1

InChI Key

DJSOIWVYQLXAFK-IIJMLMANSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Oxolane
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Organic oxide
Alcohol
Organooxygen compound
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Organic oxygen 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	3.11	ChemAxon
pKa (Strongest Acidic)	4.69	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.41 m³·mol⁻¹	ChemAxon
Polarizability	37.88 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

C00022281

Chemspider ID

9122915

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10947690

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

de Los A Mesurado M, Arias Cassara ML, Misico R, Bardon A, Ybarra MI, Cartagena E: A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis. Chem Biodivers. 2017 May;14(5). doi: 10.1002/cbdv.201600426. Epub 2017 Apr 5. [PubMed:28135782 ]
LOTUS database [Link]

Showing NP-Card for (1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid (NP0330391)

MOL for NP0330391 ((1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D MOL for NP0330391 ((1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D SDF for NP0330391 ((1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D-SDF for NP0330391 ((1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

PDB for NP0330391 ((1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D PDB for NP0330391 ((1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

SMILES for NP0330391 ((1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

INCHI for NP0330391 ((1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

Structure for NP0330391 ((1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)

3D Structure for NP0330391 ((1r,5s,8as)-5-(hydroxymethyl)-2,5,5',8a-tetramethyl-4a,6,7,8-tetrahydro-4h-spiro[naphthalene-1,2'-oxolan]-5'-ylacetic acid)