NP-MRD: Showing NP-Card for (-)-loliolide (NP0351068)

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Record Information

Version

2.0

Created at

2025-05-27 23:47:08 UTC

Updated at

2026-03-21 04:35:39 UTC

NP-MRD ID

NP0351068

Natural Product DOI

https://doi.org/10.57994/4057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-loliolide

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272007322D          

 14 15  0  0  0  0            999 V2000
   -3.3929  -14.8934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6830  -15.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9695  -14.8934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1831  -15.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7019  -14.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1910  -13.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172  -14.4684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1027  -15.3024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9752  -15.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2040  -13.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1614  -13.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9643  -14.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4018  -14.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6870  -13.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  2  3  1  0  0  0  0
  5  7  2  0  0  0  0
  1  8  1  1  0  0  0
  3  9  1  1  0  0  0
 13 14  1  0  0  0  0
 14 11  1  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
  6 12  2  0  0  0  0
 12  3  1  0  0  0  0
 13  1  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0351068

> <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+/m0/s1

> <INCHI_KEY>
XEVQXKKKAVVSMW-WRWORJQWSA-N

> <FORMULA>
C11H16O3

> <MOLECULAR_WEIGHT>
196.2429

> <EXACT_MASS>
196.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
20.69944776537595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
1.1080473940000004

> <ALOGPS_LOGS>
-1.19

> <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

> <ALOGPS_SOLUBILITY>
1.27e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -6.333 -27.801   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.008 -28.566   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.676 -27.801   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.208 -28.269   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.310 -27.017   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.223 -25.776   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.219 -27.008   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -7.658 -28.565   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.687 -29.326   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.981 -24.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.035 -24.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.667 -26.260   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.350 -26.266   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.016 -25.496   0.000  0.00  0.00           C+0
CONECT    1    2    8   13                                                  
CONECT    2    1    3                                                       
CONECT    3    4    2    9   12                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5   12                                                       
CONECT    7    5                                                            
CONECT    8    1                                                            
CONECT    9    3                                                            
CONECT   10   14                                                            
CONECT   11   14                                                            
CONECT   12   14    6    3                                                  
CONECT   13   14    1                                                       
CONECT   14   13   11   10   12                                             
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
1,3-Dihydroxy-3,5,5-trimethylcyclohexylidene-4-acetic acid lactone	MeSH
(3S5R)-Loliolide	ChEMBL
(-)-Loliolide	PhytoBank
Calendin	PhytoBank
Caulilide	PhytoBank
Digiprolactone	PhytoBank
Loliolid	PhytoBank

Chemical Formula

C₁₁H₁₆O₃

Average Mass

196.2429 Da

Monoisotopic Mass

196.10994 Da

IUPAC Name

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

Traditional Name

(6S,7aR)-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+/m0/s1

InChI Key

XEVQXKKKAVVSMW-WRWORJQWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2025-05-27	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2025-05-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	[email protected]	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2025-05-27	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2025-05-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	[email protected]	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2025-05-27	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2025-05-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	[email protected]	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2025-05-27	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Inula japonica		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

benzofurans (CHEBI:69774 )

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	1.66	ALOGPS
logP	1.11	ChemAxon
logS	-1.2	ALOGPS
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

FDB004536

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

100332

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-loliolide (NP0351068)

MOL for NP0351068 ((-)-loliolide)

3D MOL for NP0351068 ((-)-loliolide)

3D SDF for NP0351068 ((-)-loliolide)

3D-SDF for NP0351068 ((-)-loliolide)

PDB for NP0351068 ((-)-loliolide)

3D PDB for NP0351068 ((-)-loliolide)

SMILES for NP0351068 ((-)-loliolide)

INCHI for NP0351068 ((-)-loliolide)

Structure for NP0351068 ((-)-loliolide)

3D Structure for NP0351068 ((-)-loliolide)