NP-MRD: Showing NP-Card for (−)-loliolide (NP0331988)

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Record Information

Version

1.0

Created at

2023-10-17 16:08:49 UTC

Updated at

2024-05-14 21:46:44 UTC

NP-MRD ID

NP0331988

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(−)-loliolide

Description

10481-90-0 Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Based on a literature review very few articles have been published on 10481-90-0.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.4450    0.1112   -1.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0194    0.4838   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8763    1.6939    0.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111   -0.5883    1.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2783   -1.7252    0.8718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5464   -2.5632   -0.1854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1766   -1.3392    0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4701   -0.1878   -0.0318 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5364   -0.7190   -1.4802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6699    0.4411    0.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4588    1.7811    0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3639    2.6571    0.6204 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0234    1.9905    0.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4309    0.8482    0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5821    0.1471   -1.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454    0.8675   -2.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1344   -0.8701   -1.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1209    2.3315   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2753    2.2897    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8231    1.3469    0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9581   -0.0895    2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2739   -0.9071    1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4061   -2.3608    1.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5173   -2.7582   -0.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682   -2.2108    0.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620   -1.1008    1.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6114   -0.8266   -1.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479   -0.0031   -2.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0736   -1.7096   -1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5200    2.9697    0.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  6
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  2 14  1  0
 14 13  2  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 14  8  1  0
 10  8  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
  7 25  1  0
  7 26  1  0
  5 23  1  1
  6 24  1  0
  4 21  1  0
  4 22  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
 13 30  1  0
M  END


  Mrv1652309102202422D          

 14 15  0  0  1  0            999 V2000
    3.8092    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 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  2  0  0  0  0
  2 14  1  0  0  0  0
  8 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331988

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12C[C@H](O)CC(C)(C)C1=CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11+/m1/s1

> <INCHI_KEY>
XEVQXKKKAVVSMW-HQJQHLMTSA-N

> <FORMULA>
C11H16O3

> <MOLECULAR_WEIGHT>
196.246

> <EXACT_MASS>
196.109944375

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
20.69847030512578

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R,7aS)-6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

> <JCHEM_LOGP>
1.1080473940000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.127833489157034

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7428856318427135

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
52.558800000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6R,7aS)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       7.111   3.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.131   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.626  -1.532   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   14                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    2    8                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₆O₃

Average Mass

196.2460 Da

Monoisotopic Mass

196.10994 Da

IUPAC Name

(6R,7aS)-6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

Traditional Name

(6R,7aS)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one

CAS Registry Number

Not Available

SMILES

C[C@]12C[C@H](O)CC(C)(C)C1=CC(=O)O2

InChI Identifier

InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11+/m1/s1

InChI Key

XEVQXKKKAVVSMW-HQJQHLMTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
erecta		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen 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	1.11	ChemAxon
pKa (Strongest Acidic)	15.13	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	52.56 m³·mol⁻¹	ChemAxon
Polarizability	20.7 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

10472179

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12311357

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang X, Liu X, Wang X, Wang H, Zhang LH, Yu H, Yang W, Wu HH: Carotenoid-derived norsesquiterpenoids and sesquiterpenoids from Tagetes erecta L. Phytochemistry. 2023 Nov;215:113860. doi: 10.1016/j.phytochem.2023.113860. Epub 2023 Sep 14. [PubMed:37714249 ]

Showing NP-Card for (−)-loliolide (NP0331988)

MOL for NP0331988 ((−)-loliolide)

3D MOL for NP0331988 ((−)-loliolide)

3D SDF for NP0331988 ((−)-loliolide)

3D-SDF for NP0331988 ((−)-loliolide)

PDB for NP0331988 ((−)-loliolide)

3D PDB for NP0331988 ((−)-loliolide)

SMILES for NP0331988 ((−)-loliolide)

INCHI for NP0331988 ((−)-loliolide)

Structure for NP0331988 ((−)-loliolide)

3D Structure for NP0331988 ((−)-loliolide)