NP-MRD: Showing NP-Card for Loliolide (NP0046457)

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Record Information

Version

2.0

Created at

2022-03-17 20:01:23 UTC

Updated at

2025-02-11 15:45:21 UTC

NP-MRD ID

NP0046457

Natural Product DOI

https://doi.org/10.57994/0834

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Loliolide

Description

Loliolide is found in Acanthospermum hispidum, Acanthosyris paulo-alvinii, Ajuga decumbens, Anacyclus monanthos, Annona muricata , Arctotis fastuosa, Artemisia ludoviciana, Athyrium yokoscense, Bacopa monnieri, Brachystemma calycinum, Broussonetia papyrifera, Bunias orientalis, Calendula officinalis, Calyptocarpus vialis, Canscora alata, Carpesium macrocephalum, Casearia sylvestris, Centaurea aspera, Centaurea diffusa, Cheirolophus uliginosus, Cichorium intybus, Cocculus carolinus, Securigera varia, Cota palaestina, Cycas circinalis, Cystophora moniliformis, Dictyopteris divaricata, Dictyota dichotoma, Digitalis purpurea, Erythrophleum fordii, Eucommia ulmoides, Euphorbia helioscopia, Euphorbia hirta, Euphorbia maculata, Euterpe oleracea, Excoecaria cochinchinensis, Helianthus annuus, Helianthus annuus L cv.Peredovick. , Helminthotheca echioides, Schefflera taiwaniana, Hydrocotyle leucocephala, Inula japonica, Jacobaea argunensis, Lactuca serriola, Lessingianthus mollissimus, Leucas aspera, Linzia glabra, Lolium perenne, Lythrum salicaria, Macaranga triloba, Mantisalca salmantica, Melia azedarach, Melilotus messanensis, Menyanthes trifoliata, Monteverdia apurimacensis, Morus bombycis, Otanthus maritimus, Oxalis pes-caprae, Padina tetrastromatica, Pellia epiphylla, Peperomia duclouxii C. DC., Peperomia heyneana, Pimelea simplex, Piper lolot, Piper sarmentosum, Plantago major, Polygonum aviculare, Potentilla anserina, Prangos pabularia, Pseudo-nitzschia multistriata, Pterocaulon polystachyum, Pulicaria incisa, Rhaponticum coniferum, Rhaponticum serratuloides, Rosa laevigata, Rosa taiwanensis, Salvia divinorum, Salvia sahendica, Saussurea medusa, Schkuhria pinnata, Senecio vulgaris, Sida acuta, Sinularia capillosa, Sphaeranthus suaveolens, Thuja plicata, Tridax procumbens, Urospermum picroides, Veronica persica, Viscum coloratum, Vitex quinata, Volutaria tubuliflora, Xanthium spinosum and Xanthium strumarium.

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>
NP0046457

> <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
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-05-09	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400, CDCl₃, simulated)	Not Available	Not Available	Not Available	2024-05-09	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Acanthospermum hispidum	LOTUS Database	35616633
Acanthosyris paulo-alvinii	LOTUS Database	35616633
Ajuga decumbens	LOTUS Database	35616633
Anacyclus monanthos	LOTUS Database	35616633
Annona muricata	Plant	KNApSAcK
Arctotis fastuosa	LOTUS Database	35616633
Artemisia ludoviciana	LOTUS Database	35616633
Athyrium yokoscense	LOTUS Database	35616633
Bacopa monnieri	LOTUS Database	35616633
Bixa orellana		Not Available
Brachystemma calycinum	LOTUS Database	35616633
Broussonetia papyrifera	LOTUS Database	35616633
Bunias orientalis	LOTUS Database	35616633
Calendula officinalis	LOTUS Database	35616633
Calyptocarpus vialis	LOTUS Database	35616633
Canscora alata	LOTUS Database	35616633
Carpesium macrocephalum	LOTUS Database	35616633
Casearia sylvestris	LOTUS Database	35616633
Centaurea aspera	LOTUS Database	35616633
Centaurea diffusa	LOTUS Database	35616633
Cheirolophus uliginosus	LOTUS Database	35616633
Cichorium intybus	LOTUS Database	35616633
Cocculus carolinus	LOTUS Database	35616633
Coronilla varia	LOTUS Database	35616633
Cota palaestina	LOTUS Database	35616633
Cycas circinalis	LOTUS Database	35616633
Cystophora moniliformis	LOTUS Database	35616633
Dictyopteris divaricata	Chromalveolata	KNApSAcK
Dictyota dichotoma	LOTUS Database	35616633
Digitalis purpurea	LOTUS Database	35616633
Erythrophleum fordii	LOTUS Database	35616633
Eucommia ulmoides	LOTUS Database	35616633
Euphorbia helioscopia	LOTUS Database	35616633
Euphorbia hirta	LOTUS Database	35616633
Euphorbia maculata	LOTUS Database	35616633
Euterpe oleracea	LOTUS Database	35616633
Excoecaria cochinchinensis	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Helianthus annuus L cv.Peredovick.	Plant	KNApSAcK
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helminthia echioides	LOTUS Database	35616633
Heptapleurum taiwanianum	LOTUS Database	35616633
Hydrocotyle leucocephala	LOTUS Database	35616633
Inula japonica	LOTUS Database	35616633
Jacobaea argunensis	LOTUS Database	35616633
Lactuca serriola	LOTUS Database	35616633
Lessingianthus mollissimus	LOTUS Database	35616633
Leucas aspera	LOTUS Database	35616633
Linzia glabra	LOTUS Database	35616633
Lolium perenne	LOTUS Database	35616633
Lythrum salicaria	LOTUS Database	35616633
Macaranga triloba	LOTUS Database	35616633
Mantisalca salmantica	LOTUS Database	35616633
Melia azedarach	LOTUS Database	35616633
Melilotus messanensis	Plant	KNApSAcK
Menyanthes trifoliata	LOTUS Database	35616633
Monteverdia apurimacensis	LOTUS Database	35616633
Morus bombycis	LOTUS Database	35616633
Otanthus maritimus	LOTUS Database	35616633
Oxalis pes-caprae	LOTUS Database	35616633
Padina tetrastromatica	LOTUS Database	35616633
Pellia epiphylla	LOTUS Database	35616633
Peperomia duclouxii C. DC.	Plant	KNApSAcK
Peperomia heyneana	LOTUS Database	35616633
Pimelea simplex	LOTUS Database	35616633
Piper lolot	LOTUS Database	35616633
Piper sarmentosum	LOTUS Database	35616633
Plantago major	LOTUS Database	35616633
Polygonum aviculare	LOTUS Database	35616633
Potentilla anserina	LOTUS Database	35616633
Prangos pabularia	LOTUS Database	35616633
Pseudo-nitzschia multistriata	LOTUS Database	35616633
Pterocaulon polystachyum	LOTUS Database	35616633
Pulicaria incisa	LOTUS Database	35616633
Rhaponticum coniferum	LOTUS Database	35616633
Rhaponticum serratuloides	LOTUS Database	35616633
Rosa laevigata	LOTUS Database	35616633
Rosa taiwanensis	LOTUS Database	35616633
Salvia divinorum	LOTUS Database	35616633
Salvia sahendica	LOTUS Database	35616633
Saussurea medusa	LOTUS Database	35616633
Schkuhria pinnata	LOTUS Database	35616633
Senecio vulgaris	LOTUS Database	35616633
Sida acuta	LOTUS Database	35616633
Sinularia capillosa	LOTUS Database	35616633
Sphaeranthus suaveolens	LOTUS Database	35616633
Thuja plicata	LOTUS Database	35616633
Tridax procumbens	LOTUS Database	35616633
Undaria pinnatifida	FooDB	KNAPSACK
Urospermum picroides	LOTUS Database	35616633
Veronica persica	LOTUS Database	35616633
Viscum coloratum	LOTUS Database	35616633
Vitex quinata	LOTUS Database	35616633
Volutaria tubuliflora	LOTUS Database	35616633
Xanthium spinosum	LOTUS Database	35616633
Xanthium strumarium	LOTUS Database	35616633

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 (NP0046457)

MOL for NP0046457 (Loliolide)

3D MOL for NP0046457 (Loliolide)

3D SDF for NP0046457 (Loliolide)

3D-SDF for NP0046457 (Loliolide)

PDB for NP0046457 (Loliolide)

3D PDB for NP0046457 (Loliolide)

SMILES for NP0046457 (Loliolide)

INCHI for NP0046457 (Loliolide)

Structure for NP0046457 (Loliolide)

3D Structure for NP0046457 (Loliolide)