NP-MRD: Showing NP-Card for Hydroxysydonic acid (NP0058292)

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Record Information

Version

2.0

Created at

2022-04-28 03:39:13 UTC

Updated at

2022-04-28 03:39:13 UTC

NP-MRD ID

NP0058292

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hydroxysydonic acid

Description

UNII-5Z130H67HJ belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Hydroxysydonic acid is found in Aspergillus sydowii. Based on a literature review very few articles have been published on UNII-5Z130H67HJ.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 42  0  0  0  0  0  0  0  0999 V2000
    4.1795    2.1670    1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1112    1.4833    0.2179 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8398    0.6632   -0.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485    2.4664   -0.4015 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2686    0.5881    1.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1840   -0.1178    0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4156   -0.9741    1.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6925   -1.7469    0.7112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1628   -2.7153   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1634   -2.6385    1.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8234   -1.0051    0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0048   -1.0038   -1.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0265   -0.2553   -1.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911    0.5029   -1.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9625    1.2858   -1.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7444    1.9729   -0.9056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1181    1.2670   -2.9825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7155    0.5046    0.3542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6818   -0.2527    0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5995   -0.1888    2.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1768    1.6796    0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2226    3.2505    0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8992    2.0625    2.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1609    0.1625   -1.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5676    1.3286   -1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4521   -0.0916   -0.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3673    2.3877   -1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8495    1.2189    1.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663   -0.1267    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5487    0.6615   -0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6453   -0.7118   -0.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1598   -1.7294    1.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1403   -0.3629    2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4703   -3.4976    0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4253   -2.2056   -1.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0625   -3.2380   -0.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028   -3.2301    1.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3391   -1.5945   -1.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1764   -0.2487   -2.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5045    1.8865   -3.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3675    1.0842    1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600   -0.6884    2.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  6
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  1
  8 11  1  0
 11 19  2  0
 19 20  1  0
 19 18  1  0
 18 14  2  0
 14 13  1  0
 13 12  2  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 12 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 20 42  1  0
 18 41  1  0
 13 39  1  0
 12 38  1  0
 17 40  1  0
M  END


  Mrv1652304282205392D          

 20 20  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    0.7145   -0.4125    0.0000 C   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 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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5559    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    1.9520    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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  6  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0058292

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)CCC[C@@](C)(O)C1=C(O)C=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-14(2,19)7-4-8-15(3,20)11-6-5-10(13(17)18)9-12(11)16/h5-6,9,16,19-20H,4,7-8H2,1-3H3,(H,17,18)/t15-/m1/s1

> <INCHI_KEY>
YCUWMGPYKGLQQF-OAHLLOKOSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.336

> <EXACT_MASS>
282.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.108799604779648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2R)-2,6-dihydroxy-6-methylheptan-2-yl]-3-hydroxybenzoic acid

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
1.9291981293333338

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.878913978289336

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8308172195092585

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2544731591162792

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
75.8797

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2R)-2,6-dihydroxy-6-methylheptan-2-yl]-3-hydroxybenzoic 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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334  -2.310   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  O   UNK     0       4.771   0.976   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.231   3.644   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.208   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.128   6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    2   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₅

Average Mass

282.3360 Da

Monoisotopic Mass

282.14672 Da

IUPAC Name

4-[(2R)-2,6-dihydroxy-6-methylheptan-2-yl]-3-hydroxybenzoic acid

Traditional Name

4-[(2R)-2,6-dihydroxy-6-methylheptan-2-yl]-3-hydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

CC(C)(O)CCC[C@@](C)(O)C1=C(O)C=C(C=C1)C(O)=O

InChI Identifier

InChI=1S/C15H22O5/c1-14(2,19)7-4-8-15(3,20)11-6-5-10(13(17)18)9-12(11)16/h5-6,9,16,19-20H,4,7-8H2,1-3H3,(H,17,18)/t15-/m1/s1

InChI Key

YCUWMGPYKGLQQF-OAHLLOKOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aspergillus sydowii	Fungi	KNApSAcK

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

Sesquiterpenoid
Bisabolane sesquiterpenoid
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Aromatic alcohol
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	1.71	ALOGPS
logP	1.93	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.83	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	75.88 m³·mol⁻¹	ChemAxon
Polarizability	30.11 Å³	ChemAxon
Number of Rings	1	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

58828500

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25775010

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Hydroxysydonic acid (NP0058292)

MOL for NP0058292 (Hydroxysydonic acid)

3D MOL for NP0058292 (Hydroxysydonic acid)

3D SDF for NP0058292 (Hydroxysydonic acid)

3D-SDF for NP0058292 (Hydroxysydonic acid)

PDB for NP0058292 (Hydroxysydonic acid)

3D PDB for NP0058292 (Hydroxysydonic acid)

SMILES for NP0058292 (Hydroxysydonic acid)

INCHI for NP0058292 (Hydroxysydonic acid)

Structure for NP0058292 (Hydroxysydonic acid)

3D Structure for NP0058292 (Hydroxysydonic acid)