NP-MRD: Showing NP-Card for 3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid (NP0256570)

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Record Information

Version

2.0

Created at

2022-09-07 21:26:53 UTC

Updated at

2022-09-07 21:26:54 UTC

NP-MRD ID

NP0256570

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid

Description

3-({6-[(5,5,8A-trimethyl-2-methylidene-decahydronaphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]Hept-3-en-3-yl}methoxy)-3-oxopropanoic acid belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid is found in Botryosphaeria berengeriana. 3-({6-[(5,5,8A-trimethyl-2-methylidene-decahydronaphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]Hept-3-en-3-yl}methoxy)-3-oxopropanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161504112D          

 32 35  0  0  0  0            999 V2000
   -4.7771    1.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6956    0.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0954    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0954   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5079   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3329   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0954   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0954   -1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3809   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6664   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6664   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5230   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9059   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1579   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3329   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  7 32  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004161504112D          

 32 35  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0256570

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCCC2(C)C(CC34OC3C(O)C(COC(=O)CC(O)=O)=CC4=O)C(=C)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O7/c1-14-6-7-17-23(2,3)8-5-9-24(17,4)16(14)12-25-18(26)10-15(21(30)22(25)32-25)13-31-20(29)11-19(27)28/h10,16-17,21-22,30H,1,5-9,11-13H2,2-4H3,(H,27,28)

> <INCHI_KEY>
SRCFAZGFCQQNCT-UHFFFAOYSA-N

> <FORMULA>
C25H34O7

> <MOLECULAR_WEIGHT>
446.54

> <EXACT_MASS>
446.230453435

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.79420989276653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-({6-[(5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
3.4614919996666655

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.113333426604097

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.49597213576783

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5039714490765936

> <JCHEM_POLAR_SURFACE_AREA>
113.42999999999999

> <JCHEM_REFRACTIVITY>
116.15369999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic 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      -8.917   2.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.185   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.632   1.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.645   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.875   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.645  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.185  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.415  -2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.955  -2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.185  -4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.645  -4.001   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -7.645  -2.461   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -6.311  -3.231   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.977  -4.001   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.644  -3.231   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.977  -5.541   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.311  -6.311   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.645  -5.541   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.978  -6.311   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.644  -6.311   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.310  -5.541   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.976  -6.311   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.976  -7.851   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.357  -5.541   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.691  -6.311   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.025  -5.541   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.691  -7.851   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -11.495  -2.667   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -12.265  -4.001   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -12.265  -1.334   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -11.495  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.955  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   32                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   32                                             
CONECT    8    7                                                            
CONECT    9    7   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   18                                             
CONECT   12   11   13                                                       
CONECT   13   12   11   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   11   19                                                  
CONECT   19   18                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    9   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
3-({6-[(5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoate	Generator

Chemical Formula

C₂₅H₃₄O₇

Average Mass

446.5400 Da

Monoisotopic Mass

446.23045 Da

IUPAC Name

3-({6-[(5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid

Traditional Name

3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CCCC2(C)C(CC34OC3C(O)C(COC(=O)CC(O)=O)=CC4=O)C(=C)CCC12

InChI Identifier

InChI=1S/C25H34O7/c1-14-6-7-17-23(2,3)8-5-9-24(17,4)16(14)12-25-18(26)10-15(21(30)22(25)32-25)13-31-20(29)11-19(27)28/h10,16-17,21-22,30H,1,5-9,11-13H2,2-4H3,(H,27,28)

InChI Key

SRCFAZGFCQQNCT-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
Botryosphaeria berengeriana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Dicarboxylic acid or derivatives
1,3-dicarbonyl compound
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Alcohol
Hydrocarbon derivative
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	2.81	ALOGPS
logP	3.46	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	3.5	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	113.43 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	116.15 m³·mol⁻¹	ChemAxon
Polarizability	47.79 Å³	ChemAxon
Number of Rings	4	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid (NP0256570)

MOL for NP0256570 (3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid)

3D MOL for NP0256570 (3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid)

3D SDF for NP0256570 (3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid)

3D-SDF for NP0256570 (3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid)

PDB for NP0256570 (3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid)

3D PDB for NP0256570 (3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid)

SMILES for NP0256570 (3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid)

INCHI for NP0256570 (3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid)

Structure for NP0256570 (3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid)

3D Structure for NP0256570 (3-({6-[(5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methoxy)-3-oxopropanoic acid)