NP-MRD: Showing NP-Card for (4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one (NP0219528)

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Record Information

Version

2.0

Created at

2022-09-05 20:32:35 UTC

Updated at

2022-09-05 20:32:36 UTC

NP-MRD ID

NP0219528

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one

Description

Farformolide B belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one is found in Farfugium japonicum and Ligularia sagitta. (4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one was first documented in 2005 (PMID: 15792856). Based on a literature review very few articles have been published on Farformolide B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052222322D          

 22 24  0  0  1  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9441   -0.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2767   -1.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
  3 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0219528

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C2=C(C)C(=O)O[C@]2(C[C@@]2(O)CCC[C@H](C)[C@@]12C)OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O5/c1-10-7-6-8-16(19)9-17(21-5)12(11(2)14(18)22-17)13(20-4)15(10,16)3/h10,13,19H,6-9H2,1-5H3/t10-,13+,15-,16-,17-/m0/s1

> <INCHI_KEY>
YXGXDLSSHQUMKC-ROBJAKRVSA-N

> <FORMULA>
C17H26O5

> <MOLECULAR_WEIGHT>
310.39

> <EXACT_MASS>
310.178023937

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
32.84929686916113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,4aS,5S,8aS,9aS)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

> <JCHEM_LOGP>
2.6818983376666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.083310113575639

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1997601563220135

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
80.5509

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aS,5S,8aS,9aS)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,9H-naphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.799   2.016   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.275   3.481   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.705   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.245   0.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       6.799  -0.476   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.496  -1.532   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.250  -2.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4   11   13                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   16   21                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3   14   22                                             
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₆O₅

Average Mass

310.3900 Da

Monoisotopic Mass

310.17802 Da

IUPAC Name

(4S,4aS,5S,8aS,9aS)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

Traditional Name

(4S,4aS,5S,8aS,9aS)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,9H-naphtho[2,3-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C2=C(C)C(=O)O[C@]2(C[C@@]2(O)CCC[C@H](C)[C@@]12C)OC

InChI Identifier

InChI=1S/C17H26O5/c1-10-7-6-8-16(19)9-17(21-5)12(11(2)14(18)22-17)13(20-4)15(10,16)3/h10,13,19H,6-9H2,1-5H3/t10-,13+,15-,16-,17-/m0/s1

InChI Key

YXGXDLSSHQUMKC-ROBJAKRVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Farfugium japonicum	LOTUS Database	35616633
Ligularia sagitta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Eremophilanolide or secoeremophilanolide
Sesquiterpenoid
Naphthofuran
Ketal
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Ether
Oxacycle
Dialkyl ether
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen 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	2.68	ChemAxon
pKa (Strongest Acidic)	14.08	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.55 m³·mol⁻¹	ChemAxon
Polarizability	32.85 Å³	ChemAxon
Number of Rings	3	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

C00050523

Chemspider ID

136824

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155319

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hsieh TJ, Lu LH, Su CC: NMR spectroscopic, mass spectroscopic, X-ray crystallographic, and theoretical studies of molecular mechanics of natural products: farformolide B and sesamin. Biophys Chem. 2005 Apr 1;114(1):13-20. doi: 10.1016/j.bpc.2004.10.001. Epub 2004 Nov 5. [PubMed:15792856 ]
LOTUS database [Link]

Showing NP-Card for (4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one (NP0219528)

MOL for NP0219528 ((4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one)

3D MOL for NP0219528 ((4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one)

3D SDF for NP0219528 ((4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one)

3D-SDF for NP0219528 ((4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one)

PDB for NP0219528 ((4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one)

3D PDB for NP0219528 ((4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one)

SMILES for NP0219528 ((4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one)

INCHI for NP0219528 ((4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one)

Structure for NP0219528 ((4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one)

3D Structure for NP0219528 ((4s,4as,5s,8as,9as)-8a-hydroxy-4,9a-dimethoxy-3,4a,5-trimethyl-4h,5h,6h,7h,8h,9h-naphtho[2,3-b]furan-2-one)