NP-MRD: Showing NP-Card for methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate (NP0218597)

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Record Information

Version

2.0

Created at

2022-09-05 19:18:24 UTC

Updated at

2022-09-05 19:18:24 UTC

NP-MRD ID

NP0218597

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate

Description

Methyl (4R,6S,8R,10S)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate is found in Actinopolyspora erythraea. Based on a literature review very few articles have been published on methyl (4R,6S,8R,10S)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052221182D          

 20 19  0  0  1  0            999 V2000
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    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
   -0.4125   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -2.1434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250   -2.8579    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5375   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5375   -2.1434    0.0000 O   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  1  4  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0218597

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(C)=C[C@H](C)C[C@H](C)C[C@@](C)(O)C[C@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C16H30O4/c1-11(8-13(3)15(18)20-6)7-12(2)9-16(5,19)10-14(4)17/h8,11-12,14,17,19H,7,9-10H2,1-6H3/t11-,12+,14+,16-/m1/s1

> <INCHI_KEY>
IQQFJADQXWBZGX-TWJWRFFLSA-N

> <FORMULA>
C16H30O4

> <MOLECULAR_WEIGHT>
286.412

> <EXACT_MASS>
286.214409446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
33.679607021244976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (4R,6S,8R,10S)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate

> <JCHEM_LOGP>
2.7367708919999987

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.769657722309141

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.87246084589487

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5487863511632938

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
81.40589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4R,6S,8R,10S)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310  -1.334   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      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.310  -4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.620  -2.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.390  -4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.724  -3.231   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.056  -4.771   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -6.160  -5.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.700  -5.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.470  -6.668   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.470  -4.001   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
Methyl (4R,6S,8R,10S)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoic acid	Generator

Chemical Formula

C₁₆H₃₀O₄

Average Mass

286.4120 Da

Monoisotopic Mass

286.21441 Da

IUPAC Name

methyl (4R,6S,8R,10S)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate

Traditional Name

methyl (4R,6S,8R,10S)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(C)=C[C@H](C)C[C@H](C)C[C@@](C)(O)C[C@H](C)O

InChI Identifier

InChI=1S/C16H30O4/c1-11(8-13(3)15(18)20-6)7-12(2)9-16(5,19)10-14(4)17/h8,11-12,14,17,19H,7,9-10H2,1-6H3/t11-,12+,14+,16-/m1/s1

InChI Key

IQQFJADQXWBZGX-TWJWRFFLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actinopolyspora erythraea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

Acyclic monoterpenoid
Fatty alcohol
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	2.74	ChemAxon
pKa (Strongest Acidic)	14.87	ChemAxon
pKa (Strongest Basic)	-2.5	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	9	ChemAxon
Refractivity	81.41 m³·mol⁻¹	ChemAxon
Polarizability	33.68 Å³	ChemAxon
Number of Rings	0	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

163069739

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate (NP0218597)

MOL for NP0218597 (methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate)

3D MOL for NP0218597 (methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate)

3D SDF for NP0218597 (methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate)

3D-SDF for NP0218597 (methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate)

PDB for NP0218597 (methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate)

3D PDB for NP0218597 (methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate)

SMILES for NP0218597 (methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate)

INCHI for NP0218597 (methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate)

Structure for NP0218597 (methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate)

3D Structure for NP0218597 (methyl (4r,6s,8r,10s)-8,10-dihydroxy-2,4,6,8-tetramethylundec-2-enoate)