NP-MRD: Showing NP-Card for methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate (NP0247323)

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Record Information

Version

2.0

Created at

2022-09-07 09:07:58 UTC

Updated at

2022-09-07 09:07:59 UTC

NP-MRD ID

NP0247323

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate

Description

Methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate is found in Herbertus aduncus. Methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
    5.3035    1.2992   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734    0.8084   -0.0813 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7376   -0.4946    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6999   -1.2359    0.6551 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3811   -1.0476    0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1419   -2.3369    0.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507   -2.8120    0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5877   -4.1278    1.1150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1962   -1.9856    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4536   -2.4971    0.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0044   -0.6783   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1191    0.1721   -0.4626 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8431   -0.4017   -1.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5382    1.5008   -0.9505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7342    2.4124   -1.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6490    1.9120   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0395    0.6714    0.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2048   -0.2161    0.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3210    1.0658    1.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3157   -0.2474   -0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7011    1.3722    0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3017    2.2822   -0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9576    0.5986   -0.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841   -2.9676    1.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977   -4.7655    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6318   -3.4452    0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0987   -0.4435   -2.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2585   -1.3927   -1.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5989    0.3610   -1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0325    1.4151   -1.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0508    1.9510   -0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4580    3.4672   -0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1667    2.3457   -2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8213    2.6467    0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6180    1.6582   -0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0999    0.4186    1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0101   -0.8136    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5881   -0.8064    0.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6654    2.0689    2.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2149    1.1320    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5219    0.3937    2.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5943    0.7622   -0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 20  2  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 20  5  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  0
  8 25  1  0
 10 26  1  0
 20 42  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
M  END


  Mrv1533004261503222D          

 20 21  0  0  0  0            999 V2000
    3.2516    6.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5065    6.0153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9545    5.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475    5.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094    4.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0164    4.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2713    3.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0783    3.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7193    3.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9742    2.2637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9123    3.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6574    4.0044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603    2.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8082    3.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0277    2.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7728    1.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9478    1.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6928    2.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8841    1.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1344    2.7291    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 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
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247323

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC(O)=C(O)C(=C1)C1(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O4/c1-15(2)6-5-7-16(15,3)11-8-10(14(19)20-4)9-12(17)13(11)18/h8-9,17-18H,5-7H2,1-4H3

> <INCHI_KEY>
GBHHPTZARQQNFO-UHFFFAOYSA-N

> <FORMULA>
C16H22O4

> <MOLECULAR_WEIGHT>
278.348

> <EXACT_MASS>
278.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.341847171341364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate

> <ALOGPS_LOGP>
3.95

> <JCHEM_LOGP>
3.927126051

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.366342655023946

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.003489960621243

> <JCHEM_PKA_STRONGEST_BASIC>
-5.844976911468085

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
77.13449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       6.070  12.693   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.545  11.228   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.515  10.084   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.009  10.404   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.991   8.619   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.497   8.299   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.973   6.835   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.479   6.514   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.943   5.690   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.419   4.226   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.436   6.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.960   7.475   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.406   4.866   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.375   6.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.652   3.961   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.176   2.496   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.636   2.496   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.160   3.961   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.650   3.656   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.118   5.094   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11    5                                                       
CONECT   13   11   14   15   18                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19   20                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoic acid	Generator

Chemical Formula

C₁₆H₂₂O₄

Average Mass

278.3480 Da

Monoisotopic Mass

278.15181 Da

IUPAC Name

methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate

Traditional Name

methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC(O)=C(O)C(=C1)C1(C)CCCC1(C)C

InChI Identifier

InChI=1S/C16H22O4/c1-15(2)6-5-7-16(15,3)11-8-10(14(19)20-4)9-12(17)13(11)18/h8-9,17-18H,5-7H2,1-4H3

InChI Key

GBHHPTZARQQNFO-UHFFFAOYSA-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
Herbertus aduncus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Herbertane sesquiterpenoid
Sesquiterpenoid
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Methyl ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	3.95	ALOGPS
logP	3.93	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	77.13 m³·mol⁻¹	ChemAxon
Polarizability	30.34 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate (NP0247323)

MOL for NP0247323 (methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate)

3D MOL for NP0247323 (methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate)

3D SDF for NP0247323 (methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate)

3D-SDF for NP0247323 (methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate)

PDB for NP0247323 (methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate)

3D PDB for NP0247323 (methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate)

SMILES for NP0247323 (methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate)

INCHI for NP0247323 (methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate)

Structure for NP0247323 (methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate)

3D Structure for NP0247323 (methyl 3,4-dihydroxy-5-(1,2,2-trimethylcyclopentyl)benzoate)