NP-MRD: Showing NP-Card for (4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate (NP0326486)

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Record Information

Version

2.0

Created at

2022-09-12 08:05:04 UTC

Updated at

2022-09-12 08:05:04 UTC

NP-MRD ID

NP0326486

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate

Description

(4S,10aR)-4,5,6,6a,7,8,9,10-Octahydro-3-(acetoxymethyl)-10beta-acetoxy-6abeta,9beta-dihydroxy-6beta,9-dimethyl-4beta-[(E)-2-methyl-2-butenoyloxy]-2H-naphtho[8a,1-b]furan-2-one belongs to the class of organic compounds known as cadinanolides. These are sesquiterpene lactones based on 2-dioxonaphtho[4a,4-b]furan. (4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate is found in Vernonanthura nudiflora. Based on a literature review very few articles have been published on (4S,10aR)-4,5,6,6a,7,8,9,10-Octahydro-3-(acetoxymethyl)-10beta-acetoxy-6abeta,9beta-dihydroxy-6beta,9-dimethyl-4beta-[(E)-2-methyl-2-butenoyloxy]-2H-naphtho[8a,1-b]furan-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122210052D          

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M  END

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  Mrv1652309122210052D          

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M  END
> <DATABASE_ID>
NP0326486

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)O[C@H]1C[C@@H](C)[C@]2(O)CC[C@@](C)(O)[C@@H](OC(C)=O)[C@@]22OC(=O)C(COC(C)=O)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O10/c1-7-12(2)19(27)33-17-10-13(3)23(30)9-8-22(6,29)21(32-15(5)26)24(23)18(17)16(20(28)34-24)11-31-14(4)25/h7,13,17,21,29-30H,8-11H2,1-6H3/b12-7+/t13-,17+,21-,22-,23-,24-/m1/s1

> <INCHI_KEY>
XLWNGNNGOIARMC-YGLUXQSESA-N

> <FORMULA>
C24H32O10

> <MOLECULAR_WEIGHT>
480.51

> <EXACT_MASS>
480.19954723

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.194409941391946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,6R,6aR,9R,10R,10aR)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-2H,4H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4a,4-b]furan-4-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
1.2423842610000002

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.024951008235362

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.210903850225236

> <JCHEM_PKA_STRONGEST_BASIC>
-3.272493821683116

> <JCHEM_POLAR_SURFACE_AREA>
145.66

> <JCHEM_REFRACTIVITY>
116.76759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,6R,6aR,9R,10R,10aR)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4H,5H,6H,7H,8H,10H-naphtho[4a,4-b]furan-4-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.688  -0.665   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.344   0.087   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.021  -0.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.041  -2.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.677   0.052   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.657   1.592   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.354  -0.735   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.010   0.018   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.010   1.557   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.354   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.374   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.677   1.522   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.697   3.062   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.021   2.275   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.344   1.488   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.324  -0.052   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.844   0.195   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.832  -1.506   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.040  -0.595   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.960  -2.345   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.284  -3.132   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.628  -2.380   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.264  -4.672   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.657  -0.017   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.788  -1.063   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.143  -2.461   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.896  -3.805   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.614  -2.280   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.569  -3.411   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.933  -3.071   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.979  -4.202   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.522  -5.673   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.481  -3.862   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.314  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   34                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   24                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   12   25   34                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   28    8   24                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
(4S,10AR)-4,5,6,6a,7,8,9,10-octahydro-3-(acetoxymethyl)-10b-acetoxy-6abeta,9b-dihydroxy-6b,9-dimethyl-4b-[(e)-2-methyl-2-butenoyloxy]-2H-naphtho[8a,1-b]furan-2-one	Generator
(4S,10AR)-4,5,6,6a,7,8,9,10-octahydro-3-(acetoxymethyl)-10β-acetoxy-6abeta,9β-dihydroxy-6β,9-dimethyl-4β-[(e)-2-methyl-2-butenoyloxy]-2H-naphtho[8a,1-b]furan-2-one	Generator

Chemical Formula

C₂₄H₃₂O₁₀

Average Mass

480.5100 Da

Monoisotopic Mass

480.19955 Da

IUPAC Name

(4S,6R,6aR,9R,10R,10aR)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-2H,4H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4a,4-b]furan-4-yl (2E)-2-methylbut-2-enoate

Traditional Name

(4S,6R,6aR,9R,10R,10aR)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4H,5H,6H,7H,8H,10H-naphtho[4a,4-b]furan-4-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)O[C@H]1C[C@@H](C)[C@]2(O)CC[C@@](C)(O)[C@@H](OC(C)=O)[C@@]22OC(=O)C(COC(C)=O)=C12

InChI Identifier

InChI=1S/C24H32O10/c1-7-12(2)19(27)33-17-10-13(3)23(30)9-8-22(6,29)21(32-15(5)26)24(23)18(17)16(20(28)34-24)11-31-14(4)25/h7,13,17,21,29-30H,8-11H2,1-6H3/b12-7+/t13-,17+,21-,22-,23-,24-/m1/s1

InChI Key

XLWNGNNGOIARMC-YGLUXQSESA-N

Experimental Spectra

Not Available

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

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vernonanthura nudiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cadinanolides. These are sesquiterpene lactones based on 2-dioxonaphtho[4a,4-b]furan.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Cadinanolides

Alternative Parents

Substituents

Cadinanolide skeleton
Sesquiterpenoid
Cadinane sesquiterpenoid
Tetracarboxylic acid or derivatives
Naphthofuran
Fatty acid ester
2-furanone
Fatty acyl
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
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	1.24	ChemAxon
pKa (Strongest Acidic)	13.21	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.66 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	116.77 m³·mol⁻¹	ChemAxon
Polarizability	48.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

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

15139442

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate (NP0326486)

MOL for NP0326486 ((4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0326486 ((4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0326486 ((4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0326486 ((4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate)

PDB for NP0326486 ((4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0326486 ((4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0326486 ((4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0326486 ((4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate)

Structure for NP0326486 ((4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate)

3D Structure for NP0326486 ((4s,6r,6ar,9r,10r,10ar)-10-(acetyloxy)-3-[(acetyloxy)methyl]-6a,9-dihydroxy-6,9-dimethyl-2-oxo-4h,5h,6h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl (2e)-2-methylbut-2-enoate)