NP-MRD: Showing NP-Card for trans-(3S,6R)-3-Hydroxyl-α-ionylideneacetic acid (NP0331985)

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Record Information

Version

1.0

Created at

2023-10-17 16:07:04 UTC

Updated at

2024-05-14 21:46:43 UTC

NP-MRD ID

NP0331985

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trans-(3S,6R)-3-Hydroxyl-α-ionylideneacetic acid

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 10172316072D          

 18 18  0  0  1  0            999 V2000
    1.2448    1.8695    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
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  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
    2.8579    0.8250    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   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
    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  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  0  0  0  0
  4  5  1  1  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
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331985

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\[C@H]1C(C)=C[C@@H](O)CC1(C)C)=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-10(7-14(17)18)5-6-13-11(2)8-12(16)9-15(13,3)4/h5-8,12-13,16H,9H2,1-4H3,(H,17,18)/b6-5+,10-7+/t12-,13+/m1/s1

> <INCHI_KEY>
IGUWZNQUMTWGPH-DYFNGHAXSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.338

> <EXACT_MASS>
250.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.45043018873334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E)-5-[(1R,4S)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid

> <JCHEM_LOGP>
2.5294218503333328

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.217272339876406

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.705114964613129

> <JCHEM_PKA_STRONGEST_BASIC>
-1.391565528062598

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
74.6537

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E)-5-[(1R,4S)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-OCT-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-OCT-23         0                                  
HETATM    1  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   18                                             
CONECT    3    2                                                            
CONECT    4    2    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    4   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₃

Average Mass

250.3380 Da

Monoisotopic Mass

250.15689 Da

IUPAC Name

(2E,4E)-5-[(1R,4S)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid

Traditional Name

(2E,4E)-5-[(1R,4S)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid

CAS Registry Number

Not Available

SMILES

C\C(\C=C\[C@H]1C(C)=C[C@@H](O)CC1(C)C)=C/C(O)=O

InChI Identifier

InChI=1S/C15H22O3/c1-10(7-14(17)18)5-6-13-11(2)8-12(16)9-15(13,3)4/h5-8,12-13,16H,9H2,1-4H3,(H,17,18)/b6-5+,10-7+/t12-,13+/m1/s1

InChI Key

IGUWZNQUMTWGPH-DYFNGHAXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
erecta		Not Available

Chemical Taxonomy

Classification

Not classified

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	2.53	ChemAxon
pKa (Strongest Acidic)	4.71	ChemAxon
pKa (Strongest Basic)	-1.4	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	3	ChemAxon
Refractivity	74.65 m³·mol⁻¹	ChemAxon
Polarizability	28.45 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

Not Available

References

General References

Wang X, Liu X, Wang X, Wang H, Zhang LH, Yu H, Yang W, Wu HH: Carotenoid-derived norsesquiterpenoids and sesquiterpenoids from Tagetes erecta L. Phytochemistry. 2023 Nov;215:113860. doi: 10.1016/j.phytochem.2023.113860. Epub 2023 Sep 14. [PubMed:37714249 ]

Showing NP-Card for trans-(3S,6R)-3-Hydroxyl-α-ionylideneacetic acid (NP0331985)

MOL for NP0331985 (trans-(3S,6R)-3-Hydroxyl-α-ionylideneacetic acid)

3D MOL for NP0331985 (trans-(3S,6R)-3-Hydroxyl-α-ionylideneacetic acid)

3D SDF for NP0331985 (trans-(3S,6R)-3-Hydroxyl-α-ionylideneacetic acid)

3D-SDF for NP0331985 (trans-(3S,6R)-3-Hydroxyl-α-ionylideneacetic acid)

PDB for NP0331985 (trans-(3S,6R)-3-Hydroxyl-α-ionylideneacetic acid)

3D PDB for NP0331985 (trans-(3S,6R)-3-Hydroxyl-α-ionylideneacetic acid)

SMILES for NP0331985 (trans-(3S,6R)-3-Hydroxyl-α-ionylideneacetic acid)

INCHI for NP0331985 (trans-(3S,6R)-3-Hydroxyl-α-ionylideneacetic acid)

Structure for NP0331985 (trans-(3S,6R)-3-Hydroxyl-α-ionylideneacetic acid)

3D Structure for NP0331985 (trans-(3S,6R)-3-Hydroxyl-α-ionylideneacetic acid)