NP-MRD: Showing NP-Card for 12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde (NP0183284)

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Record Information

Version

2.0

Created at

2022-09-03 22:10:01 UTC

Updated at

2022-09-03 22:10:01 UTC

NP-MRD ID

NP0183284

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde

Description

12-({7A-hydroxy-2a,5,7-trimethyl-1H,2H,2aH,3H,3aH,4H,5H,6H,7aH-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]Tridec-2-ene-2-carbaldehyde belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde is found in Phlebia uda. Based on a literature review very few articles have been published on 12-({7a-hydroxy-2a,5,7-trimethyl-1H,2H,2aH,3H,3aH,4H,5H,6H,7aH-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]Tridec-2-ene-2-carbaldehyde.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042200102D          

 35 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042200102D          

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    1.3233   -4.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8440   -5.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0903   -5.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -4.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8864   -5.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  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
  8  9  1  0  0  0  0
  9 10  1  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
 13 14  1  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
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 22 25  1  0  0  0  0
  9 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
 13 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
 30 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183284

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2CC(C)(COC3OC(=O)C45CC34C(C=O)=C3CC(C)(C)CC3C5)CC2CC2(C)CCC12O

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O5/c1-17-20-13-26(4,9-19(20)10-27(5)6-7-30(17,27)33)16-34-24-29-15-28(29,23(32)35-24)11-18-8-25(2,3)12-21(18)22(29)14-31/h14,18-19,24,33H,6-13,15-16H2,1-5H3

> <INCHI_KEY>
JVSGWCCMXPFMRE-UHFFFAOYSA-N

> <FORMULA>
C30H40O5

> <MOLECULAR_WEIGHT>
480.645

> <EXACT_MASS>
480.287574388

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.32096498033219

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-({7a-hydroxy-2a,5,7-trimethyl-1H,2H,2aH,3H,3aH,4H,5H,6H,7aH-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0^{1,9}.0^{3,7}]tridec-2-ene-2-carbaldehyde

> <JCHEM_LOGP>
4.092264261000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.70704464481052

> <JCHEM_PKA_STRONGEST_BASIC>
-0.739811890344856

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
132.18980000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
12-({2a-hydroxy-3,5,7a-trimethyl-1H,2H,4H,6H,6aH,7H-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0^{1,9}.0^{3,7}]tridec-2-ene-2-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.110  -8.361   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.704  -7.735   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.543  -6.203   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.573  -5.059   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.803  -3.725   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.210  -3.099   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.327  -2.261   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.179  -1.941   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.250   0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.179   3.481   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.252   2.016   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.157   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.301   1.800   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.301  -0.260   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.252  -0.476   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.453  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.120  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.453   0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.297  -4.046   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.136  -5.577   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.110  -6.482   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.949  -8.014   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.470  -7.773   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.575  -9.421   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.169 -10.047   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.458  -8.640   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.655  -9.609   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   27                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   25   26                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22    9   13   26                                             
CONECT   26   25   13                                                       
CONECT   27    5   28                                                       
CONECT   28   27    3   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32   34                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    2   30   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₅

Average Mass

480.6450 Da

Monoisotopic Mass

480.28757 Da

IUPAC Name

12-({7a-hydroxy-2a,5,7-trimethyl-1H,2H,2aH,3H,3aH,4H,5H,6H,7aH-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0^{1,9}.0^{3,7}]tridec-2-ene-2-carbaldehyde

Traditional Name

12-({2a-hydroxy-3,5,7a-trimethyl-1H,2H,4H,6H,6aH,7H-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0^{1,9}.0^{3,7}]tridec-2-ene-2-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC1=C2CC(C)(COC3OC(=O)C45CC34C(C=O)=C3CC(C)(C)CC3C5)CC2CC2(C)CCC12O

InChI Identifier

InChI=1S/C30H40O5/c1-17-20-13-26(4,9-19(20)10-27(5)6-7-30(17,27)33)16-34-24-29-15-28(29,23(32)35-24)11-18-8-25(2,3)12-21(18)22(29)14-31/h14,18-19,24,33H,6-13,15-16H2,1-5H3

InChI Key

JVSGWCCMXPFMRE-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
Phlebia uda	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Sterpuran sesquiterpenoid
Delta valerolactone
Delta_valerolactone
Gamma butyrolactone
Oxane
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Cyclobutanol
Lactone
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Aldehyde
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
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	4.09	ChemAxon
pKa (Strongest Acidic)	19.71	ChemAxon
pKa (Strongest Basic)	-0.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	132.19 m³·mol⁻¹	ChemAxon
Polarizability	53.32 Å³	ChemAxon
Number of Rings	7	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

72681723

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde (NP0183284)

MOL for NP0183284 (12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde)

3D MOL for NP0183284 (12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde)

3D SDF for NP0183284 (12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde)

3D-SDF for NP0183284 (12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde)

PDB for NP0183284 (12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde)

3D PDB for NP0183284 (12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde)

SMILES for NP0183284 (12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde)

INCHI for NP0183284 (12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde)

Structure for NP0183284 (12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde)

3D Structure for NP0183284 (12-({2a-hydroxy-3,5,7a-trimethyl-1h,2h,4h,6h,6ah,7h-cyclobuta[f]inden-5-yl}methoxy)-5,5-dimethyl-10-oxo-11-oxatetracyclo[7.3.1.0¹,⁹.0³,⁷]tridec-2-ene-2-carbaldehyde)