NP-MRD: Showing NP-Card for (2e,6e,8e)-10-{8-[(1e,3e)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid (NP0182518)

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Record Information

Version

2.0

Created at

2022-09-03 21:13:52 UTC

Updated at

2022-09-03 21:13:52 UTC

NP-MRD ID

NP0182518

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,6e,8e)-10-{8-[(1e,3e)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid

Description

(2E,6E,8E)-5-hydroxy-10-[10-[(1E,3E)-5-hydroxy-3-methyl-5-oxo-penta-1,3-dienyl]-3,9-dimethyl-5,11-dioxaspiro[5.5]Undecan-4-yl]-4,8-dimethyl-deca-2,6,8-trienoic acid belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. Based on a literature review very few articles have been published on (2E,6E,8E)-5-hydroxy-10-[10-[(1E,3E)-5-hydroxy-3-methyl-5-oxo-penta-1,3-dienyl]-3,9-dimethyl-5,11-dioxaspiro[5.5]Undecan-4-yl]-4,8-dimethyl-deca-2,6,8-trienoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032223132D          

 36 37  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309032223132D          

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    1.9520   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  2 14  2  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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 23 32  1  0  0  0  0
 18 32  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 16 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0182518

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(\C=C\C(O)=O)C(O)\C=C\C(\C)=C\CC1OC2(CCC1C)CCC(C)C(O2)\C=C\C(\C)=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O7/c1-19(6-10-24(30)21(3)9-13-27(31)32)7-11-25-22(4)14-16-29(35-25)17-15-23(5)26(36-29)12-8-20(2)18-28(33)34/h6-10,12-13,18,21-26,30H,11,14-17H2,1-5H3,(H,31,32)(H,33,34)/b10-6+,12-8+,13-9+,19-7+,20-18+

> <INCHI_KEY>
ZUPXAYGYALHVSA-GRUORMGSSA-N

> <FORMULA>
C29H42O7

> <MOLECULAR_WEIGHT>
502.648

> <EXACT_MASS>
502.293053692

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
56.916592057829156

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,6E,8E)-10-{8-[(1E,3E)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid

> <JCHEM_LOGP>
5.425674347333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.985799063079491

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.335252412753628

> <JCHEM_PKA_STRONGEST_BASIC>
-1.33587023645193

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
144.11010000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6E,8E)-10-{8-[(1E,3E)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.746   6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.516   4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.056   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.826   6.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.366   6.105   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -7.136   4.771   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -7.136   7.438   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.366   8.772   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.676   7.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.446   8.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -10.986   8.772   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0     -11.756  10.106   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0     -11.756   7.438   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.746   3.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.206   3.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.954   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.184  -3.231   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.954  -4.565   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.494  -4.565   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.184  -5.898   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.954  -7.232   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.494  -7.232   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.184  -8.566   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.644  -0.564   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    2   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   35                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   32   33                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   23   18                                                       
CONECT   33   18   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   16   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Value	Source
(2E,6E,8E)-5-Hydroxy-10-[10-[(1E,3E)-5-hydroxy-3-methyl-5-oxo-penta-1,3-dienyl]-3,9-dimethyl-5,11-dioxaspiro[5.5]undecan-4-yl]-4,8-dimethyl-deca-2,6,8-trienoate	Generator

Chemical Formula

C₂₉H₄₂O₇

Average Mass

502.6480 Da

Monoisotopic Mass

502.29305 Da

IUPAC Name

(2E,6E,8E)-10-{8-[(1E,3E)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid

Traditional Name

(2E,6E,8E)-10-{8-[(1E,3E)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid

CAS Registry Number

Not Available

SMILES

CC(\C=C\C(O)=O)C(O)\C=C\C(\C)=C\CC1OC2(CCC1C)CCC(C)C(O2)\C=C\C(\C)=C\C(O)=O

InChI Identifier

InChI=1S/C29H42O7/c1-19(6-10-24(30)21(3)9-13-27(31)32)7-11-25-22(4)14-16-29(35-25)17-15-23(5)26(36-29)12-8-20(2)18-28(33)34/h6-10,12-13,18,21-26,30H,11,14-17H2,1-5H3,(H,31,32)(H,33,34)/b10-6+,12-8+,13-9+,19-7+,20-18+

InChI Key

ZUPXAYGYALHVSA-GRUORMGSSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Medium-chain fatty acid
Branched fatty acid
Ketal
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Oxane
Unsaturated fatty acid
Fatty acid
Secondary alcohol
Oxacycle
Acetal
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	5.43	ChemAxon
pKa (Strongest Acidic)	4.34	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	144.11 m³·mol⁻¹	ChemAxon
Polarizability	56.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

4977745

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6476190

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e,6e,8e)-10-{8-[(1e,3e)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid (NP0182518)

MOL for NP0182518 ((2e,6e,8e)-10-{8-[(1e,3e)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid)

3D MOL for NP0182518 ((2e,6e,8e)-10-{8-[(1e,3e)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid)

3D SDF for NP0182518 ((2e,6e,8e)-10-{8-[(1e,3e)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid)

3D-SDF for NP0182518 ((2e,6e,8e)-10-{8-[(1e,3e)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid)

PDB for NP0182518 ((2e,6e,8e)-10-{8-[(1e,3e)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid)

3D PDB for NP0182518 ((2e,6e,8e)-10-{8-[(1e,3e)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid)

SMILES for NP0182518 ((2e,6e,8e)-10-{8-[(1e,3e)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid)

INCHI for NP0182518 ((2e,6e,8e)-10-{8-[(1e,3e)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid)

Structure for NP0182518 ((2e,6e,8e)-10-{8-[(1e,3e)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid)

3D Structure for NP0182518 ((2e,6e,8e)-10-{8-[(1e,3e)-4-carboxy-3-methylbuta-1,3-dien-1-yl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid)