NP-MRD: Showing NP-Card for (4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid (NP0330430)

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Record Information

Version

1.0

Created at

2022-09-12 15:46:36 UTC

Updated at

2022-09-12 15:46:36 UTC

NP-MRD ID

NP0330430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid

Description

(4R)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid belongs to the class of organic compounds known as naphthalenecarboxylic acids. Naphthalenecarboxylic acids are compounds containing a naphthalene moiety, which bears a carboxylic acid group one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring. (4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid is found in Peganum nigellastrum. It was first documented in 2003 (PMID: 12820211). Based on a literature review a small amount of articles have been published on (4R)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid (PMID: 33524854) (PMID: 14733519) (PMID: 32726026) (PMID: 16032352).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122217462D          

 14 15  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.0000    0.8250    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   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  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CC(=CC2=CC=CC=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O3/c12-10-6-8(11(13)14)5-7-3-1-2-4-9(7)10/h1-5,10,12H,6H2,(H,13,14)/t10-/m1/s1

> <INCHI_KEY>
SGBGJSLWUVWLBW-SNVBAGLBSA-N

> <FORMULA>
C11H10O3

> <MOLECULAR_WEIGHT>
190.198

> <EXACT_MASS>
190.062994182

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.10720509515887

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid

> <JCHEM_LOGP>
1.3505211689999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.356703724493833

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.109694173925331

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0982294242783777

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
52.1715

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic 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  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    4                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
(4R)-4-Hydroxy-3,4-dihydronaphthalene-2-carboxylate	Generator

Chemical Formula

C₁₁H₁₀O₃

Average Mass

190.1980 Da

Monoisotopic Mass

190.06299 Da

IUPAC Name

(4R)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid

Traditional Name

(4R)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC(=CC2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C11H10O3/c12-10-6-8(11(13)14)5-7-3-1-2-4-9(7)10/h1-5,10,12H,6H2,(H,13,14)/t10-/m1/s1

InChI Key

SGBGJSLWUVWLBW-SNVBAGLBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Peganum nigellastrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenecarboxylic acids. Naphthalenecarboxylic acids are compounds containing a naphthalene moiety, which bears a carboxylic acid group one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthalenecarboxylic acids and derivatives

Direct Parent

Naphthalenecarboxylic acids

Alternative Parents

Substituents

2-naphthalenecarboxylic acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	1.35	ChemAxon
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	52.17 m³·mol⁻¹	ChemAxon
Polarizability	19.11 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

162905794

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kaunda JS, Qin XJ, Zhu HT, Wang D, Yang CR, Zhang YJ: Previously undescribed pyridyl-steroidal glycoalkaloids and 23S,26R-hydroxylated spirostanoid saponin from the fruits of Solanum violaceum ortega and their bioactivities. Phytochemistry. 2021 Apr;184:112656. doi: 10.1016/j.phytochem.2021.112656. Epub 2021 Jan 29. [PubMed:33524854 ]
Kikuzaki H, Kayano S, Fukutsuka N, Aoki A, Kasamatsu K, Yamasaki Y, Mitani T, Nakatani N: Abscisic acid related compounds and lignans in prunes (Prunus domestica L.) and their oxygen radical absorbance capacity (ORAC). J Agric Food Chem. 2004 Jan 28;52(2):344-9. doi: 10.1021/jf034954v. [PubMed:14733519 ]
Liu W, Chen L, Wang ZG, Cui H, Yuan T: [Study on chemical constituents from Mastic (Pistacia lentiscus)]. Zhongguo Zhong Yao Za Zhi. 2020 Jul;45(13):3169-3174. doi: 10.19540/j.cnki.cjcmm.20200403.201. [PubMed:32726026 ]
Anderson JC, O'Loughlin JM, Tornos JA: Asymmetric aza-[2,3]-Wittig sigmatropic rearrangements: chiral auxiliary control and formal asymmetric synthesis of (2S, 3R, 4R)-4-hydroxy-3-methylproline and (-)-kainic acid. Org Biomol Chem. 2005 Aug 7;3(15):2741-9. doi: 10.1039/b506198a. Epub 2005 Jun 30. [PubMed:16032352 ]
Segura M, Ortuno J, Farre M, Pacifici R, Pichini S, Joglar J, Segura J, de la Torre R: Quantitative determination of paroxetine and its 4-hydroxy-3-methoxy metabolite in plasma by high-performance liquid chromatography/electrospray ion trap mass spectrometry: application to pharmacokinetic studies. Rapid Commun Mass Spectrom. 2003;17(13):1455-61. doi: 10.1002/rcm.1067. [PubMed:12820211 ]
LOTUS database [Link]

Showing NP-Card for (4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid (NP0330430)

MOL for NP0330430 ((4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid)

3D MOL for NP0330430 ((4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid)

3D SDF for NP0330430 ((4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid)

3D-SDF for NP0330430 ((4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid)

PDB for NP0330430 ((4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid)

3D PDB for NP0330430 ((4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid)

SMILES for NP0330430 ((4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid)

INCHI for NP0330430 ((4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid)

Structure for NP0330430 ((4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid)

3D Structure for NP0330430 ((4r)-4-hydroxy-3,4-dihydronaphthalene-2-carboxylic acid)