NP-MRD: Showing NP-Card for 3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid (NP0304879)

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Record Information

Version

2.0

Created at

2022-09-10 20:16:32 UTC

Updated at

2022-09-10 20:16:32 UTC

NP-MRD ID

NP0304879

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid

Description

3-Hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). 3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid is found in Hymenaea courbaril. 3-Hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004231515282D          

 24 25  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171   -2.4072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5991    1.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8707    1.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3276    1.0983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    2.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8109    2.2429    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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  6 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0304879

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2C(=CC(O)CC2(C)C(O)=O)C1(C)CCC(C)(O)C=C

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

> <INCHI_KEY>
FGKUISKCUDFGTR-UHFFFAOYSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.04633481019218

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.207367464666667

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.875606778580607

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.641992104021658

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3681733790219655

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
95.38349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.405  -4.493   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.760  -5.746   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.723   1.360   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.723   1.360   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.262   1.413   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.985   2.773   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.625   3.496   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.345   2.050   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.708   4.133   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.247   4.187   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    6    2   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-1-carboxylate	Generator

Chemical Formula

C₂₀H₃₂O₄

Average Mass

336.4720 Da

Monoisotopic Mass

336.23006 Da

IUPAC Name

3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

Traditional Name

3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1CCC2C(=CC(O)CC2(C)C(O)=O)C1(C)CCC(C)(O)C=C

InChI Identifier

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

InChI Key

FGKUISKCUDFGTR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hymenaea courbaril	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.17	ALOGPS
logP	3.21	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.38 m³·mol⁻¹	ChemAxon
Polarizability	38.05 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

85354228

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid (NP0304879)

MOL for NP0304879 (3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid)

3D MOL for NP0304879 (3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid)

3D SDF for NP0304879 (3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid)

3D-SDF for NP0304879 (3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid)

PDB for NP0304879 (3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid)

3D PDB for NP0304879 (3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid)

SMILES for NP0304879 (3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid)

INCHI for NP0304879 (3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid)

Structure for NP0304879 (3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid)

3D Structure for NP0304879 (3-hydroxy-5-(3-hydroxy-3-methylpent-4-en-1-yl)-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid)