NP-MRD: Showing NP-Card for (2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid (NP0284368)

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Record Information

Version

2.0

Created at

2022-09-09 12:01:57 UTC

Updated at

2022-09-09 12:01:57 UTC

NP-MRD ID

NP0284368

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid

Description

ZINC71758418 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. (2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid is found in Zea mays. Based on a literature review very few articles have been published on ZINC71758418.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092214012D          

 20 21  0  0  1  0            999 V2000
    2.2848   -2.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5634   -2.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3752   -1.8928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6538   -1.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4656   -0.9692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1206   -0.4867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0302   -1.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436   -0.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941   -0.0001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3642    0.5150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    0.9268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9285    1.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174   -0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624   -0.9270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7978   -1.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -0.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247   -0.0001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2471    0.1013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    0.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0284368

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\[C@]1(O)[C@]2(C)CO[C@@]1(C)C[C@H](O)C2)=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-10(6-12(17)18)4-5-15(19)13(2)7-11(16)8-14(15,3)20-9-13/h4-6,11,16,19H,7-9H2,1-3H3,(H,17,18)/b5-4+,10-6-/t11-,13+,14+,15+/m1/s1

> <INCHI_KEY>
XIVFQYWMMJWUCD-JKQLRLFLSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.336

> <EXACT_MASS>
282.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.48780309232635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4E)-5-[(1S,3R,5S,8S)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid

> <JCHEM_LOGP>
0.5024939413333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.891974587545853

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.566584044161994

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7397165799455063

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
75.0039

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4E)-5-[(1S,3R,5S,8S)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       4.265  -5.257   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.785  -3.808   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.300  -3.533   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.820  -2.084   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.336  -1.809   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.825  -0.908   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.790  -2.632   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.375  -1.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.602  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.413   0.961   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.170   1.730   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.733   3.354   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.966   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.966  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.170  -1.730   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.489  -3.244   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.671  -1.388   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.339  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.061   0.189   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.671   1.387   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   15                                             
CONECT   10    9                                                            
CONECT   11    9   12   13   20                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    9   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₅

Average Mass

282.3360 Da

Monoisotopic Mass

282.14672 Da

IUPAC Name

(2Z,4E)-5-[(1S,3R,5S,8S)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid

Traditional Name

(2Z,4E)-5-[(1S,3R,5S,8S)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid

CAS Registry Number

Not Available

SMILES

C\C(\C=C\[C@]1(O)[C@]2(C)CO[C@@]1(C)C[C@H](O)C2)=C\C(O)=O

InChI Identifier

InChI=1S/C15H22O5/c1-10(6-12(17)18)4-5-15(19)13(2)7-11(16)8-14(15,3)20-9-13/h4-6,11,16,19H,7-9H2,1-3H3,(H,17,18)/b5-4+,10-6-/t11-,13+,14+,15+/m1/s1

InChI Key

XIVFQYWMMJWUCD-JKQLRLFLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Zea mays	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
Heterocyclic fatty acid
Hydroxy fatty acid
Oxepane
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	0.5	ChemAxon
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75 m³·mol⁻¹	ChemAxon
Polarizability	29.49 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

65061214

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129008854

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid (NP0284368)

MOL for NP0284368 ((2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

3D MOL for NP0284368 ((2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

3D SDF for NP0284368 ((2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

3D-SDF for NP0284368 ((2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

PDB for NP0284368 ((2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

3D PDB for NP0284368 ((2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

SMILES for NP0284368 ((2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

INCHI for NP0284368 ((2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

Structure for NP0284368 ((2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)

3D Structure for NP0284368 ((2z,4e)-5-[(1s,3r,5s,8s)-3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid)