NP-MRD: Showing NP-Card for (6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid (NP0215911)

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Record Information

Version

2.0

Created at

2022-09-05 15:41:16 UTC

Updated at

2022-09-05 15:41:16 UTC

NP-MRD ID

NP0215911

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid

Description

2-[6-(1-Hydroxy-6-{[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]methyl}hepta-2,4-dien-2-yl)-5-methyloxan-2-yl]acetic acid belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 2-[6-(1-Hydroxy-6-{[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]methyl}hepta-2,4-dien-2-yl)-5-methyloxan-2-yl]acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161520512D          

 32 33  0  0  0  0            999 V2000
    0.6857   -8.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7432   -7.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0288   -5.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 31 32  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004161520512D          

 32 33  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0215911

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(C(C)O)C(C)C1OC1(C)CC(C)C=CC=C(CO)C1OC(CC(O)=O)CCC1C

> <INCHI_IDENTIFIER>
InChI=1S/C25H42O7/c1-15(13-25(5)24(32-25)17(3)23(30-6)18(4)27)8-7-9-19(14-26)22-16(2)10-11-20(31-22)12-21(28)29/h7-9,15-18,20,22-24,26-27H,10-14H2,1-6H3,(H,28,29)

> <INCHI_KEY>
RTVDEACIRKOYGE-UHFFFAOYSA-N

> <FORMULA>
C25H42O7

> <MOLECULAR_WEIGHT>
454.604

> <EXACT_MASS>
454.293053692

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.975704606323404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
2.6718472349999995

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.392566968706628

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.493045419609035

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7671637231555

> <JCHEM_POLAR_SURFACE_AREA>
108.75000000000001

> <JCHEM_REFRACTIVITY>
124.10869999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.280 -15.033   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.280 -13.493   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.054 -12.723   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.387 -13.493   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.721 -12.723   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.387 -15.033   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.054 -11.183   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.280 -10.413   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.387 -10.413   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.927 -10.413   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.157  -9.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.041  -7.818   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.274  -7.818   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.260  -7.952   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.911  -9.348   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.143  -6.690   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.678  -6.825   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.561  -5.563   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.095  -5.697   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.746  -7.093   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.280  -7.227   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.978  -4.436   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.327  -3.040   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.211  -1.779   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.560  -0.383   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.443   0.879   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.792   2.274   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       7.977   0.744   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.745  -1.913   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.396  -3.309   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.512  -4.570   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.163  -5.966   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9   11                                                       
CONECT   11   10    9   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   22   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
2-[6-(1-Hydroxy-6-{[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]methyl}hepta-2,4-dien-2-yl)-5-methyloxan-2-yl]acetate	Generator

Chemical Formula

C₂₅H₄₂O₇

Average Mass

454.6040 Da

Monoisotopic Mass

454.29305 Da

IUPAC Name

2-(6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid

Traditional Name

(6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid

CAS Registry Number

Not Available

SMILES

COC(C(C)O)C(C)C1OC1(C)CC(C)C=CC=C(CO)C1OC(CC(O)=O)CCC1C

InChI Identifier

InChI=1S/C25H42O7/c1-15(13-25(5)24(32-25)17(3)23(30-6)18(4)27)8-7-9-19(14-26)22-16(2)10-11-20(31-22)12-21(28)29/h7-9,15-18,20,22-24,26-27H,10-14H2,1-6H3,(H,28,29)

InChI Key

RTVDEACIRKOYGE-UHFFFAOYSA-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
Fatty alcohol
Oxane
Fatty acyl
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen compound
Primary alcohol
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	3.16	ALOGPS
logP	2.67	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.75 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	124.11 m³·mol⁻¹	ChemAxon
Polarizability	51.98 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

85046185

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid (NP0215911)

MOL for NP0215911 ((6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid)

3D MOL for NP0215911 ((6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid)

3D SDF for NP0215911 ((6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid)

3D-SDF for NP0215911 ((6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid)

PDB for NP0215911 ((6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid)

3D PDB for NP0215911 ((6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid)

SMILES for NP0215911 ((6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid)

INCHI for NP0215911 ((6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid)

Structure for NP0215911 ((6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid)

3D Structure for NP0215911 ((6-{1-hydroxy-7-[3-(4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl]-6-methylhepta-2,4-dien-2-yl}-5-methyloxan-2-yl)acetic acid)