NP-MRD: Showing NP-Card for (-)-abscisic acid (NP0280090)

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Record Information

Version

2.0

Created at

2022-09-09 05:42:31 UTC

Updated at

2022-09-09 05:42:31 UTC

NP-MRD ID

NP0280090

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-abscisic acid

Description

(-)-Abscisic acid, also known as (R)-abscisate, belongs to the class of organic compounds known as abscisic acids and derivatives. (-)-abscisic acid is found in Lygodium japonicum and Pisum sativum. These are terpene compounds containing the abscisic acid moiety, which is characterized by a 3-methylpenta-2,4-dienoic acid attached to the C1 carbon of a 4-oxocyclohex-2-ene moiety (-)-abscisic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
   -1.4918   -0.8158   -1.9675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8335   -0.5175   -0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0881   -0.5941   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4224   -0.3010    1.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5197   -0.6555    1.7575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4798    0.4364    2.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244    1.0462    1.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302    1.9788    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3959    1.8263    1.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208   -0.1240    0.4611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7081   -1.2245    1.3419 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767    0.2265   -0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4953   -0.6551   -0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7425   -0.2486   -0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9260    1.1731   -1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7523   -1.0540   -1.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7414   -2.4310   -0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8003   -3.0379   -0.0915 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9149   -3.1822   -0.8498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4253   -0.7926   -2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711   -1.8490   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160   -0.1349   -2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015   -0.8712   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918    1.1992    2.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9371   -0.3068    2.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8900    3.0430    0.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2463    1.9034    0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9092    1.7286   -0.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0716    2.6956    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8490    2.2757    2.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274    1.2648    2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024   -2.0749    0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6439    1.2326   -0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2348   -1.6278    0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5707    1.8883   -0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3590    1.3753   -2.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9958    1.3882   -1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6968   -0.6564   -1.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1484   -3.5272   -1.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  2  0
 12 10  1  0
 10 11  1  1
 10  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 19  1  0
 17 18  2  0
  7 10  1  0
 13 34  1  0
 12 33  1  0
 11 32  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 19 39  1  0
M  END


  Mrv0541 05031423352D          

 22 22  0  0  1  0            999 V2000
   -0.8764    3.1335    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
   -0.8125    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663    2.6447    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
    0.2182    4.0520    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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640    3.2767    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0307    4.1952    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    1.2375    0.0000 C   0  0  2  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
    1.3128    4.9705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610    3.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788    2.7880    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    1.7262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121    4.6840    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
 10  1  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  2  0  0  0  0
 11  2  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 14  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14  9  1  0  0  0  0
 15  6  1  6  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16 12  2  0  0  0  0
 17 13  2  0  0  0  0
 18 13  1  0  0  0  0
 15 19  1  1  0  0  0
 20  5  1  0  0  0  0
 21  6  1  0  0  0  0
 22  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0280090

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-10(7-13(17)18)5-6-15(19)11(2)8-12(16)9-14(15,3)4/h5-8,19H,9H2,1-4H3,(H,17,18)/b6-5+,10-7-/t15-/m0/s1

> <INCHI_KEY>
JLIDBLDQVAYHNE-QHFMCZIYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.84182236447717

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
2.0932754933333335

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.403514092027617

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.738149522274699

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4976545251493247

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
74.97639999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-abscisic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   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   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5    6   10   20                                                  
CONECT    6    5   15   21                                                  
CONECT    7   10   13   22                                                  
CONECT    8   11   12                                                       
CONECT    9   12   14                                                       
CONECT   10    1    5    7                                                  
CONECT   11    2    8   15                                                  
CONECT   12    8    9   16                                                  
CONECT   13    7   17   18                                                  
CONECT   14    3    4    9   15                                             
CONECT   15    6   11   14   19                                             
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18   13                                                            
CONECT   19   15                                                            
CONECT   20    5                                                            
CONECT   21    6                                                            
CONECT   22    7                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
(-)-ABA	ChEBI
(7E,9Z)-(6R)-6-Hydroxy-3-oxo-11-apo-epsilon-caroten-11-Oic acid	ChEBI
(R)-Abscisic acid	ChEBI
(7E,9Z)-(6R)-6-Hydroxy-3-oxo-11-apo-epsilon-caroten-11-Oate	Generator
(R)-Abscisate	Generator
(-)-Abscisate	Generator
Abscisic acid monoammonium salt, (R)-isomer	MeSH
Abscisic acid, (e,e)-(+-)-isomer	MeSH
Abscisic acid, (e,Z)-(+,-)-isomer	MeSH
Abscisic acid, (R)-isomer	MeSH
Abscisic acid, (Z,e)-isomer	MeSH
Abscisic acid	MeSH
Abscisic acid, (+,-)-isomer	MeSH
Abscissins	MeSH
Abscissic acid	MeSH

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3169 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

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

Traditional Name

(-)-abscisic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H20O4/c1-10(7-13(17)18)5-6-15(19)11(2)8-12(16)9-14(15,3)4/h5-8,19H,9H2,1-4H3,(H,17,18)/b6-5+,10-7-/t15-/m0/s1

InChI Key

JLIDBLDQVAYHNE-QHFMCZIYSA-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
Lygodium japonicum	LOTUS Database	35616633
Pisum sativum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as abscisic acids and derivatives. These are terpene compounds containing the abscisic acid moiety, which is characterized by a 3-methylpenta-2,4-dienoic acid attached to the C1 carbon of a 4-oxocyclohex-2-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Abscisic acids and derivatives

Alternative Parents

Substituents

Abscisic acid
Medium-chain fatty acid
Branched fatty acid
Cyclohexenone
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Tertiary alcohol
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

2-cis-abscisic acid (CHEBI:28937 )
Cyclofarnesane sesquiterpenoids (C11060 )
Farnesenes (C11060 )
Cyclofarnesane sesquiterpenoids (LMPR0103050008 )

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	1.88	ALOGPS
logP	2.09	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.98 m³·mol⁻¹	ChemAxon
Polarizability	27.84 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

Not Available

KEGG Compound ID

C11060

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

643732

PDB ID

Not Available

ChEBI ID

28937

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (-)-abscisic acid (NP0280090)

MOL for NP0280090 ((-)-abscisic acid)

3D MOL for NP0280090 ((-)-abscisic acid)

3D SDF for NP0280090 ((-)-abscisic acid)

3D-SDF for NP0280090 ((-)-abscisic acid)

PDB for NP0280090 ((-)-abscisic acid)

3D PDB for NP0280090 ((-)-abscisic acid)

SMILES for NP0280090 ((-)-abscisic acid)

INCHI for NP0280090 ((-)-abscisic acid)

Structure for NP0280090 ((-)-abscisic acid)

3D Structure for NP0280090 ((-)-abscisic acid)