NP-MRD: Showing NP-Card for (3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate (NP0252111)

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Record Information

Version

2.0

Created at

2022-09-07 15:31:29 UTC

Updated at

2022-09-07 15:31:29 UTC

NP-MRD ID

NP0252111

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate

Description

(3AS,5R,5aS,6S,8R,9aS,9bS)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-6-yl acetate belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. (3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate is found in Cratystylis conocephala. Based on a literature review very few articles have been published on (3aS,5R,5aS,6S,8R,9aS,9bS)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-6-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072217312D          

 26 28  0  0  1  0            999 V2000
    4.2295   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.4640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7983   -0.2372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4083   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -0.9900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1937   -1.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.2887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7591   -1.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245   -0.3145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0655   -1.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8901   -1.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801   -1.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247   -0.3660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.1137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1547    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9793    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    2.4905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.4383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  6  0  0  0
  6 26  1  0  0  0  0
 11 26  1  0  0  0  0
M  END


  Mrv1652309072217312D          

 26 28  0  0  1  0            999 V2000
    4.2295   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.4640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7983   -0.2372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4083   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -0.9900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1937   -1.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.2887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7591   -1.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245   -0.3145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0655   -1.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8901   -1.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801   -1.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247   -0.3660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.1137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1547    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9793    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    2.4905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.4383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  6  0  0  0
  6 26  1  0  0  0  0
 11 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252111

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@H](OC(C)=O)[C@]2(C)[C@H](O)C[C@@H]3[C@H](OC(=O)C3=C)[C@H]2C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O7/c1-8-12-6-14(22)19(5)15(25-11(4)21)7-13(24-10(3)20)9(2)16(19)17(12)26-18(8)23/h12-17,22H,1-2,6-7H2,3-5H3/t12-,13+,14+,15-,16+,17-,19-/m0/s1

> <INCHI_KEY>
CYCAFAAOXPUZMW-XENJLOSESA-N

> <FORMULA>
C19H24O7

> <MOLECULAR_WEIGHT>
364.394

> <EXACT_MASS>
364.152203113

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.9305353736427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,5R,5aS,6S,8R,9aS,9bS)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-6-yl acetate

> <JCHEM_LOGP>
0.5529526656666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.582775214824949

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9812941210355675

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000002

> <JCHEM_REFRACTIVITY>
88.9263

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,5R,5aS,6S,8R,9aS,9bS)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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       7.895  -1.070   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.719  -0.076   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.832   1.460   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.141   2.271   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.406   2.042   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.412   0.866   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.223  -0.443   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.495  -1.800   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.956  -1.848   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.228  -3.205   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.145  -0.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.417  -1.896   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.606  -0.587   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.122  -1.944   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.662  -1.992   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.389  -3.349   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.473  -0.683   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.206   0.722   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.522   2.079   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.289   3.388   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.828   3.340   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.556   1.983   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.639   4.649   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.062   2.127   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.790   3.484   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.873   0.818   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   26                                             
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    6   11                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
(3AS,5R,5as,6S,8R,9as,9BS)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-6-yl acetic acid	Generator

Chemical Formula

C₁₉H₂₄O₇

Average Mass

364.3940 Da

Monoisotopic Mass

364.15220 Da

IUPAC Name

(3aS,5R,5aS,6S,8R,9aS,9bS)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-dodecahydronaphtho[1,2-b]furan-6-yl acetate

Traditional Name

(3aS,5R,5aS,6S,8R,9aS,9bS)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@H](OC(C)=O)[C@]2(C)[C@H](O)C[C@@H]3[C@H](OC(=O)C3=C)[C@H]2C1=C

InChI Identifier

InChI=1S/C19H24O7/c1-8-12-6-14(22)19(5)15(25-11(4)21)7-13(24-10(3)20)9(2)16(19)17(12)26-18(8)23/h12-17,22H,1-2,6-7H2,3-5H3/t12-,13+,14+,15-,16+,17-,19-/m0/s1

InChI Key

CYCAFAAOXPUZMW-XENJLOSESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cratystylis conocephala	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Tricarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	0.55	ChemAxon
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.93 m³·mol⁻¹	ChemAxon
Polarizability	36.93 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

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

163006811

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate (NP0252111)

MOL for NP0252111 ((3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate)

3D MOL for NP0252111 ((3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate)

3D SDF for NP0252111 ((3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate)

3D-SDF for NP0252111 ((3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate)

PDB for NP0252111 ((3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate)

3D PDB for NP0252111 ((3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate)

SMILES for NP0252111 ((3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate)

INCHI for NP0252111 ((3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate)

Structure for NP0252111 ((3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate)

3D Structure for NP0252111 ((3as,5r,5as,6s,8r,9as,9bs)-8-(acetyloxy)-5-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-octahydronaphtho[1,2-b]furan-6-yl acetate)