NP-MRD: Showing NP-Card for Desacetylovatifolin (NP0044146)

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Record Information

Version

1.0

Created at

2021-11-12 23:52:36 UTC

Updated at

2021-11-26 17:45:56 UTC

NP-MRD ID

NP0044146

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Desacetylovatifolin

Description

Desacetylovatifolin belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. It was first documented in 1981 (Werner Herz, Narendra Kumar). Based on a literature review very few articles have been published on Desacetylovatifolin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -3.2665   -0.8115    1.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0279   -1.1238    1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3062   -2.2220    1.9816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6731   -2.9312    2.9839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0826   -2.4071    1.3093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3362   -1.8031    0.0257 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6484   -1.9440   -0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8453   -1.4137   -0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8654   -1.5994   -1.9898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1880   -0.6088    0.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809    0.8440   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    1.7343    0.4636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0454    1.9464    0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897    2.8939    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397    3.4442    1.9508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7071    1.3911   -1.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5638    0.2021   -0.7460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8270   -0.5947   -1.8281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9953   -0.5558    0.4317 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7469    0.0150    1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9019   -1.3332    2.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -2.4372   -0.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4673   -2.5408   -1.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4106   -2.0431   -2.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2091   -0.5752   -2.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216   -2.1889   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2512   -0.9457    0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6758   -0.8105    1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3258    1.2103    0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316    0.9138   -1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6503    2.2637    1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099    2.3853    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1950    3.7215    0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3667    4.2714    1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0253    1.0610   -1.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3548    2.1507   -1.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5355    0.6241   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5467   -0.2987   -2.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4824    0.1158    1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6 19  1  0
 19 17  1  0
 17 16  1  0
 16 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 13 14  1  0
 14 15  1  0
 17 18  1  0
 19  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
 10  8  1  0
  5  6  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
  7 23  1  0
  6 22  1  6
 19 39  1  1
 17 37  1  1
 16 35  1  0
 16 36  1  0
 12 31  1  0
 11 29  1  0
 11 30  1  0
 10 27  1  0
 10 28  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 18 38  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652311132100522D          

 19 20  0  0  1  0            999 V2000
    2.3186   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817    0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589    0.9365    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7502    1.7084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5643    1.8420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8556    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012    1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    1.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9610    3.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7751    3.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3624    1.6330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061    2.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1447    3.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832    1.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551    2.0620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652    0.9751    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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 14  1  1  0  0  0
  5 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  4 19  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044146

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C\[C@H]2OC(=O)C(=C)[C@@H]2[C@H](O)C\C(CO)=C/CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-9-4-3-5-11(8-16)7-12(17)14-10(2)15(18)19-13(14)6-9/h5-6,12-14,16-17H,2-4,7-8H2,1H3/b9-6-,11-5+/t12-,13-,14-/m1/s1

> <INCHI_KEY>
IAYQFYAFBVYKJZ-CMKLNOBNSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.84443318268744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4R,11aR)-4-hydroxy-6-(hydroxymethyl)-10-methyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
1.1902336900000001

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.291965707857152

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.569385722571603

> <JCHEM_PKA_STRONGEST_BASIC>
-2.729995939261908

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
73.2918

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4R,11aR)-4-hydroxy-6-(hydroxymethyl)-10-methyl-3-methylidene-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       4.328  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.352   0.806   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.832   0.557   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.857   1.748   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.400   3.189   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.920   3.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.464   4.879   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.983   5.129   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.959   3.937   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.416   2.497   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.896   2.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.527   6.570   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.047   6.819   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.410   3.048   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.198   4.151   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.270   5.690   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.089   3.305   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.529   3.849   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.682   1.820   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2                                                       
CONECT   12    8   13                                                       
CONECT   13   12                                                            
CONECT   14    6                                                            
CONECT   15    5   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    4                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

(3aR,4R,11aR)-4-hydroxy-6-(hydroxymethyl)-10-methyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

Traditional Name

(3aR,4R,11aR)-4-hydroxy-6-(hydroxymethyl)-10-methyl-3-methylidene-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

CAS Registry Number

Not Available

SMILES

C\C1=C\[C@H]2OC(=O)C(=C)[C@@H]2[C@H](O)C\C(CO)=C/CC1

InChI Identifier

InChI=1S/C15H20O4/c1-9-4-3-5-11(8-16)7-12(17)14-10(2)15(18)19-13(14)6-9/h5-6,12-14,16-17H,2-4,7-8H2,1H3/b9-6-,11-5+/t12-,13-,14-/m1/s1

InChI Key

IAYQFYAFBVYKJZ-CMKLNOBNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Helianthus grosseserratus

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	1.18	ALOGPS
logP	1.19	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.57	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.29 m³·mol⁻¹	ChemAxon
Polarizability	27.84 Å³	ChemAxon
Number of Rings	2	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

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

92446265

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Werner Herz, Narendra Kumar (1981). Sesquiterpene lactones from Helianthus grosseserratus. Phytochemistry, Volume 20, Issue 1, 1981, Pages 99-104. DOI: 10.1016/0031-9422(81)85225-9. Phytochemistry.

Showing NP-Card for Desacetylovatifolin (NP0044146)

MOL for NP0044146 (Desacetylovatifolin)

3D MOL for NP0044146 (Desacetylovatifolin)

3D SDF for NP0044146 (Desacetylovatifolin)

3D-SDF for NP0044146 (Desacetylovatifolin)

PDB for NP0044146 (Desacetylovatifolin)

3D PDB for NP0044146 (Desacetylovatifolin)

SMILES for NP0044146 (Desacetylovatifolin)

INCHI for NP0044146 (Desacetylovatifolin)

Structure for NP0044146 (Desacetylovatifolin)

3D Structure for NP0044146 (Desacetylovatifolin)