NP-MRD: Showing NP-Card for (6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione (NP0269816)

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Record Information

Version

2.0

Created at

2022-09-08 15:25:19 UTC

Updated at

2022-09-08 15:25:19 UTC

NP-MRD ID

NP0269816

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione

Description

Sassafrin A belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione is found in Creosphaeria sassafras. Based on a literature review very few articles have been published on Sassafrin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082217252D          

 34 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082217252D          

 34 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0269816

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)\C=C(/C)\C=C\C(\O)=C\C(=O)[C@@H]1[C@@H]2C3=COC(CC(C)O)=CC3=CC(=O)[C@]2(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O7/c1-6-15(2)9-16(3)7-8-19(29)13-22(30)24-25-21-14-33-20(10-17(4)28)11-18(21)12-23(31)27(25,5)34-26(24)32/h7-9,11-15,17,24-25,28-29H,6,10H2,1-5H3/b8-7+,16-9+,19-13-/t15?,17?,24-,25+,27+/m1/s1

> <INCHI_KEY>
FRERSNXTZNXIGN-OGDDRNBVSA-N

> <FORMULA>
C27H32O7

> <MOLECULAR_WEIGHT>
468.546

> <EXACT_MASS>
468.21480337

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
50.15286162216296

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6aR,9S,9aR)-9-[(2Z,4E,6E)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromene-6,8-dione

> <JCHEM_LOGP>
2.9573829289999995

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.943552758083325

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.457313003357916

> <JCHEM_PKA_STRONGEST_BASIC>
-2.569218276244242

> <JCHEM_POLAR_SURFACE_AREA>
110.13

> <JCHEM_REFRACTIVITY>
133.8636

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6aR,9S,9aR)-9-[(2Z,4E,6E)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9H,9aH-furo[2,3-h]isochromene-6,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.888  -9.842   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.776  -8.777   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.297  -9.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.930 -10.702   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.185  -8.141   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.293  -8.571   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.660 -10.066   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.405  -7.505   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.884  -7.935   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.996  -6.869   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.474  -7.299   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.628  -5.374   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.740  -4.308   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.219  -4.738   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.373  -2.812   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.947  -2.230   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.638  -3.041   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.060  -0.694   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.556  -0.327   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.612   0.890   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.284   1.030   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.473   2.339   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.823   1.078   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.635  -0.231   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.174  -0.183   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.985  -1.492   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.524  -1.444   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.336  -2.753   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.875  -2.705   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.608  -4.110   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      10.257  -2.849   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.718  -2.897   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.907  -1.588   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.367  -1.636   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                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   34                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   34                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   26   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   24   34                                                  
CONECT   34   33   15   19                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₇

Average Mass

468.5460 Da

Monoisotopic Mass

468.21480 Da

IUPAC Name

(6aR,9S,9aR)-9-[(2Z,4E,6E)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromene-6,8-dione

Traditional Name

(6aR,9S,9aR)-9-[(2Z,4E,6E)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9H,9aH-furo[2,3-h]isochromene-6,8-dione

CAS Registry Number

Not Available

SMILES

CCC(C)\C=C(/C)\C=C\C(\O)=C\C(=O)[C@@H]1[C@@H]2C3=COC(CC(C)O)=CC3=CC(=O)[C@]2(C)OC1=O

InChI Identifier

InChI=1S/C27H32O7/c1-6-15(2)9-16(3)7-8-19(29)13-22(30)24-25-21-14-33-20(10-17(4)28)11-18(21)12-23(31)27(25,5)34-26(24)32/h7-9,11-15,17,24-25,28-29H,6,10H2,1-5H3/b8-7+,16-9+,19-13-/t15?,17?,24-,25+,27+/m1/s1

InChI Key

FRERSNXTZNXIGN-OGDDRNBVSA-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
Creosphaeria sassafras	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Alpha-acyloxy ketone
Gamma butyrolactone
Pyran
1,3-dicarbonyl compound
Acryloyl-group
Enone
Oxolane
Alpha,beta-unsaturated ketone
Vinylogous acid
Lactone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Enol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Aldehyde
Organic oxide
Alcohol
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	2.96	ChemAxon
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	133.86 m³·mol⁻¹	ChemAxon
Polarizability	50.15 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

C00053769

Chemspider ID

9926422

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11751719

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione (NP0269816)

MOL for NP0269816 ((6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D MOL for NP0269816 ((6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D SDF for NP0269816 ((6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D-SDF for NP0269816 ((6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

PDB for NP0269816 ((6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D PDB for NP0269816 ((6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

SMILES for NP0269816 ((6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

INCHI for NP0269816 ((6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

Structure for NP0269816 ((6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)

3D Structure for NP0269816 ((6ar,9s,9ar)-9-[(2z,4e,6e)-3-hydroxy-6,8-dimethyldeca-2,4,6-trienoyl]-3-(2-hydroxypropyl)-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione)