NP-MRD: Showing NP-Card for [4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate (NP0237646)

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Record Information

Version

2.0

Created at

2022-09-06 20:51:14 UTC

Updated at

2022-09-06 20:51:15 UTC

NP-MRD ID

NP0237646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate

Description

[4,5-Dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-decahydronaphthalen-4a-yl]methyl 2-methylbut-2-enoate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. [4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate is found in Ajuga ciliata and Ajuga decumbens. [4,5-Dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-decahydronaphthalen-4a-yl]methyl 2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191513282D          

 32 34  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004191513282D          

 32 34  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0237646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OCC12C(O)CC(C)C(C)(CCC3=CC(=O)OC3)C1CCCC2(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O7/c1-5-16(2)22(29)32-15-25-19(7-6-9-24(25,30)14-26)23(4,17(3)11-20(25)27)10-8-18-12-21(28)31-13-18/h5,12,17,19-20,26-27,30H,6-11,13-15H2,1-4H3

> <INCHI_KEY>
MIOANCGOVTTWSH-UHFFFAOYSA-N

> <FORMULA>
C25H38O7

> <MOLECULAR_WEIGHT>
450.572

> <EXACT_MASS>
450.261753564

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.19174551916778

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-decahydronaphthalen-4a-yl]methyl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
2.8614556459999982

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.37617296909788

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.471544284772939

> <JCHEM_PKA_STRONGEST_BASIC>
-3.008145238110064

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
120.69499999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2H-furan-3-yl)ethyl]-hexahydro-2H-naphthalen-4a-yl]methyl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   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  C   UNK     0       0.990   1.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.990   1.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.463   2.627   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.053   2.894   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.729   4.278   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.254   4.064   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.323   5.172   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.521   2.547   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.161   1.824   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.027  -3.803   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.929  -4.493   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                                                       
CONECT    9    8   10   25   29                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   25                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   19                                                       
CONECT   25   15    9   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    9   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
[4,5-Dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-decahydronaphthalen-4a-yl]methyl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₈O₇

Average Mass

450.5720 Da

Monoisotopic Mass

450.26175 Da

IUPAC Name

[4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-decahydronaphthalen-4a-yl]methyl 2-methylbut-2-enoate

Traditional Name

[4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2H-furan-3-yl)ethyl]-hexahydro-2H-naphthalen-4a-yl]methyl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OCC12C(O)CC(C)C(C)(CCC3=CC(=O)OC3)C1CCCC2(O)CO

InChI Identifier

InChI=1S/C25H38O7/c1-5-16(2)22(29)32-15-25-19(7-6-9-24(25,30)14-26)23(4,17(3)11-20(25)27)10-8-18-12-21(28)31-13-18/h5,12,17,19-20,26-27,30H,6-11,13-15H2,1-4H3

InChI Key

MIOANCGOVTTWSH-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

Species Name	Source	Reference
Ajuga ciliata	LOTUS Database	35616633
Ajuga decumbens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Fatty acid ester
2-furanone
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Dihydrofuran
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
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	2.43	ALOGPS
logP	2.86	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.47	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	120.7 m³·mol⁻¹	ChemAxon
Polarizability	49.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

78410299

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate (NP0237646)

MOL for NP0237646 ([4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate)

3D MOL for NP0237646 ([4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate)

3D SDF for NP0237646 ([4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate)

3D-SDF for NP0237646 ([4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate)

PDB for NP0237646 ([4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate)

3D PDB for NP0237646 ([4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate)

SMILES for NP0237646 ([4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate)

INCHI for NP0237646 ([4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate)

Structure for NP0237646 ([4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate)

3D Structure for NP0237646 ([4,5-dihydroxy-5-(hydroxymethyl)-1,2-dimethyl-1-[2-(5-oxo-2h-furan-3-yl)ethyl]-hexahydro-2h-naphthalen-4a-yl]methyl 2-methylbut-2-enoate)