NP-MRD: Showing NP-Card for Carolenalone (NP0064036)

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Record Information

Version

2.0

Created at

2022-04-28 08:19:58 UTC

Updated at

2022-04-28 08:19:58 UTC

NP-MRD ID

NP0064036

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Carolenalone

Description

Carolenalone belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom). Carolenalone is found in Helenium autumnale. Based on a literature review very few articles have been published on Carolenalone.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    1.6605    3.0673   -0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6759    1.9821   -0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460    0.9124    0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5642    0.7404    0.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8486   -0.6592    0.0798 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9566   -1.2224    0.6887 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610   -1.3779    0.4242 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2646   -2.3892   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8340   -2.1121    1.6011 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4940   -0.3682    0.6266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7931   -0.6058   -0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8302    0.3529    0.4357 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2303   -0.1927    0.3380 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3490   -1.6379    0.6667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5824    0.1202   -1.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5893   -0.3432   -1.6714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    0.9927   -1.5766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9508    1.5723   -0.4443 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6977    2.1874   -0.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    3.0712   -1.7453 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1724    4.0202   -0.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775    2.8103   -1.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2199    3.2380    0.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2396    1.4787    0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6317    0.7817    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0004   -0.6027   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843   -1.2948    0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391   -2.7555   -1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7646   -3.2801   -0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -1.9745   -1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3215   -1.5422    2.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2555   -0.2805    1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7034   -0.3892   -1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819   -1.6535    0.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5573    0.6818    1.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8754    0.3842    1.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0391   -2.3252   -0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8197   -1.8236    1.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4240   -1.8528    0.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408    2.2894    0.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  1
  3  2  2  0
  2  1  1  0
  2 19  1  0
 19 20  2  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 13  1  0
 18 12  1  0
  7 10  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 13 36  1  1
 12 35  1  1
 11 33  1  0
 11 34  1  0
 10 32  1  1
  4 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 18 40  1  1
M  END


  Mrv1652304282210192D          

 20 22  0  0  1  0            999 V2000
    1.6352   -0.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1496    0.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9746    0.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3326    0.9407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890   -0.4476    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3054   -1.2519    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5621   -1.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -1.2519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1106   -1.6751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4893   -1.1323    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8136   -0.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150   -1.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495   -2.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6428   -2.3546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0136   -1.6751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6349   -1.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4392   -1.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107   -0.3737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876   -2.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7917    0.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  1  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 10 12  1  6  0  0  0
  9 13  1  1  0  0  0
  9 14  1  6  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  5 18  1  1  0  0  0
 15 19  1  1  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0064036

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2C[C@@H]3C(C[C@@H](O)[C@@]3(C)O)=C(C)C(=O)[C@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O5/c1-6-8-5-11(16)15(3,19)10(8)4-9-7(2)14(18)20-13(9)12(6)17/h7,9-11,13,16,19H,4-5H2,1-3H3/t7-,9+,10+,11+,13-,15-/m0/s1

> <INCHI_KEY>
VWGLVYYBDXRCST-YXOFDIGKSA-N

> <FORMULA>
C15H20O5

> <MOLECULAR_WEIGHT>
280.32

> <EXACT_MASS>
280.131073744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.924111514840295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aR,4aR,5S,6R,9aS)-5,6-dihydroxy-3,5,8-trimethyl-2H,3H,3aH,4H,4aH,5H,6H,7H,9H,9aH-azuleno[6,5-b]furan-2,9-dione

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
0.5599595119999998

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.918370576067339

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.53051562148034

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2711597607307867

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
70.83290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,4aR,5S,6R,9aS)-5,6-dihydroxy-3,5,8-trimethyl-3H,3aH,4H,4aH,6H,7H,9aH-azuleno[6,5-b]furan-2,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.052  -0.836   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.013   0.368   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.553   0.368   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.221   1.756   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.513  -0.836   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.170  -2.337   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.783  -3.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.395  -2.337   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.073  -3.127   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.913  -2.114   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.519  -0.698   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.588  -2.456   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.706  -4.531   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.200  -4.395   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.492  -3.127   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.652  -2.114   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.153  -2.456   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.047  -0.698   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.630  -4.661   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.344   1.756   0.000  0.00  0.00           C+0
CONECT    1    2    8   11                                                  
CONECT    2    1    3   20                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   18                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    1    9                                                  
CONECT    9    8   10   13   14                                             
CONECT   10    9   11   12                                                  
CONECT   11   10    1                                                       
CONECT   12   10                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15    6   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    5                                                       
CONECT   19   15                                                            
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₅

Average Mass

280.3200 Da

Monoisotopic Mass

280.13107 Da

IUPAC Name

(3S,3aR,4aR,5S,6R,9aS)-5,6-dihydroxy-3,5,8-trimethyl-2H,3H,3aH,4H,4aH,5H,6H,7H,9H,9aH-azuleno[6,5-b]furan-2,9-dione

Traditional Name

(3S,3aR,4aR,5S,6R,9aS)-5,6-dihydroxy-3,5,8-trimethyl-3H,3aH,4H,4aH,6H,7H,9aH-azuleno[6,5-b]furan-2,9-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2C[C@@H]3C(C[C@@H](O)[C@@]3(C)O)=C(C)C(=O)[C@H]2OC1=O

InChI Identifier

InChI=1S/C15H20O5/c1-6-8-5-11(16)15(3,19)10(8)4-9-7(2)14(18)20-13(9)12(6)17/h7,9-11,13,16,19H,4-5H2,1-3H3/t7-,9+,10+,11+,13-,15-/m0/s1

InChI Key

VWGLVYYBDXRCST-YXOFDIGKSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Helenium autumnale	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-acyloxy ketones

Alternative Parents

Substituents

Alpha-acyloxy ketone
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
1,2-diol
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
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	0.21	ALOGPS
logP	0.56	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	13.53	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.83 m³·mol⁻¹	ChemAxon
Polarizability	28.92 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00020956

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

101277360

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Carolenalone (NP0064036)

MOL for NP0064036 (Carolenalone)

3D MOL for NP0064036 (Carolenalone)

3D SDF for NP0064036 (Carolenalone)

3D-SDF for NP0064036 (Carolenalone)

PDB for NP0064036 (Carolenalone)

3D PDB for NP0064036 (Carolenalone)

SMILES for NP0064036 (Carolenalone)

INCHI for NP0064036 (Carolenalone)

Structure for NP0064036 (Carolenalone)

3D Structure for NP0064036 (Carolenalone)