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Showing NP-Card for (3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one (NP0241140)

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Record Information
Version2.0
Created at2022-09-07 01:08:07 UTC
Updated at2022-09-07 01:08:07 UTC
NP-MRD IDNP0241140
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one
DescriptionSalicifoliol belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. Salicifoliol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one is found in Magnolia kachirachirai. (3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one was first documented in 2005 (PMID: 15720788). Based on a literature review a small amount of articles have been published on salicifoliol (PMID: 26767291) (PMID: 30384535) (PMID: 24660446) (PMID: 23624606).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0241140 ((3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)


  Mrv1652309072203082D          

 18 20  0  0  1  0            999 V2000
   -1.1092   -3.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -2.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937    1.1971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5666   -2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -3.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498   -4.0609    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
  6 14  1  0  0  0  0
  9 14  1  0  0  0  0
  5 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
Download

3D MOL for NP0241140 ((3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

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3D SDF for NP0241140 ((3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)

  Mrv1652309072203082D          

 18 20  0  0  1  0            999 V2000
   -1.1092   -3.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -2.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937    1.1971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5666   -2.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -3.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498   -4.0609    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
  6 14  1  0  0  0  0
  9 14  1  0  0  0  0
  5 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0241140

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@H]1OC[C@H]2[C@@H]1COC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O5/c1-16-11-4-7(2-3-10(11)14)12-8-5-18-13(15)9(8)6-17-12/h2-4,8-9,12,14H,5-6H2,1H3/t8-,9-,12+/m0/s1

> <INCHI_KEY>
HYZRWYQBGNTGTK-HOTUBEGUSA-N

> <FORMULA>
C13H14O5

> <MOLECULAR_WEIGHT>
250.25

> <EXACT_MASS>
250.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.618603456654895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,6aR)-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-one

> <JCHEM_LOGP>
0.8663245363333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.91073582439074

> <JCHEM_PKA_STRONGEST_BASIC>
-4.10669101553383

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
62.17560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,6aR)-4-(4-hydroxy-3-methoxyphenyl)-tetrahydro-3H-furo[3,4-c]furan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0241140 ((3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)
Download
PDB for NP0241140 ((3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.071  -6.756   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.595  -5.291   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.088  -4.971   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.388  -3.507   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.894  -3.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.465  -0.476   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.775   2.235   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.204  -0.476   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.924  -4.331   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.449  -5.795   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.942  -6.116   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.466  -7.580   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6    9                                                  
CONECT   15    5   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    3   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

Download
3D PDB for NP0241140 ((3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)
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SMILES for NP0241140 ((3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)
COC1=CC(=CC=C1O)[C@H]1OC[C@H]2[C@@H]1COC2=O
Download
INCHI for NP0241140 ((3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)-tetrahydro-3h-furo[3,4-c]furan-1-one)
InChI=1S/C13H14O5/c1-16-11-4-7(2-3-10(11)14)12-8-5-18-13(15)9(8)6-17-12/h2-4,8-9,12,14H,5-6H2,1H3/t8-,9-,12+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC13H14O5
Average Mass250.2500 Da
Monoisotopic Mass250.08412 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC=C1O)[C@H]1OC[C@H]2[C@@H]1COC2=O
InChI Identifier
InChI=1S/C13H14O5/c1-16-11-4-7(2-3-10(11)14)12-8-5-18-13(15)9(8)6-17-12/h2-4,8-9,12,14H,5-6H2,1H3/t8-,9-,12+/m0/s1
InChI KeyHYZRWYQBGNTGTK-HOTUBEGUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Magnolia kachirachiraiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others.
KingdomOrganic compounds  
Super ClassLignans, neolignans and related compounds  
ClassLignan lactones  
Sub ClassNot Available
Direct ParentLignan lactones  
Alternative Parents
Substituents
  • Lignan lactone
    • 

  • Furanoid lignan
    • 

  • Furofuran lignan skeleton
    • 

  • Methoxyphenol
    • 

  • Phenoxy compound
    • 

  • Furofuran
    • 

  • Phenol ether
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Phenol
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Gamma butyrolactone
    • 

  • Monocyclic benzene moiety
    • 

  • Oxolane
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Dialkyl ether
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9131179  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10955962  
PDB IDNot Available
ChEBI ID132822  
Good Scents IDNot Available
References
General References
  1. Wu GH, Chen Y, Zheng LH, Huang T, Hao XJ, Zhang JX: [Chemical Constituents of Eucommia ulmoides in Guizhou Province]. Zhong Yao Cai. 2015 May;38(5):980-4. [PubMed:26767291  ] 
  2. Chen HY, Tu LF, Xiao CR, Luo YM: [Chemical constituents from fruits of Vitex trifolia var. simplicifolia]. Zhongguo Zhong Yao Za Zhi. 2018 Sep;43(18):3694-3700. doi:  10.19540/j.cnki.cjcmm.20180625.002. [PubMed:30384535  ] 
  3. Kato M, He YM, Dibwe DF, Li F, Awale S, Kadota S, Tezuka Y: New guaian-type sesquiterpene from Wikstroemia indica. Nat Prod Commun. 2014 Jan;9(1):1-2. [PubMed:24660446  ] 
  4. Yang CP, Huang GJ, Huang HC, Chen YC, Chang CI, Wang SY, Chang HS, Tseng YH, Chien SC, Kuo YH: The effect of the aerial part of Lindera akoensis on lipopolysaccharides (LPS)-induced nitric oxide production in RAW264.7 cells. Int J Mol Sci. 2013 Apr 26;14(5):9168-81. doi: 10.3390/ijms14059168. [PubMed:23624606  ] 
  5. Steffan B, Watjen W, Michels G, Niering P, Wray V, Ebel R, Edrada R, Kahl R, Proksch P: Polyphenols from plants used in traditional Indonesian medicine (Jamu): uptake and antioxidative effects in rat H4IIE hepatoma cells. J Pharm Pharmacol. 2005 Feb;57(2):233-40. doi: 10.1211/0022357055317. [PubMed:15720788  ] 
  6. LOTUS database [Link]