NP-MRD: Showing NP-Card for (+)-Amentol chromane diacetate (NP0078912)

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Record Information

Version

2.0

Created at

2022-04-29 00:00:14 UTC

Updated at

2022-04-29 00:00:14 UTC

NP-MRD ID

NP0078912

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Amentol chromane diacetate

Description

(1S,4'S,4aR,7aR)-3-{[(2S)-5-(acetyloxy)-2,7-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]methyl}-4a,5',5',7a-tetramethyl-5,6,7,7a-tetrahydro-4aH-spiro[cyclopenta[c]pyran-1,2'-oxolane]-4'-yl acetate belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. (+)-Amentol chromane diacetate is found in Cystoseira sp. Based on a literature review very few articles have been published on (1S,4'S,4aR,7aR)-3-{[(2S)-5-(acetyloxy)-2,7-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]methyl}-4a,5',5',7a-tetramethyl-5,6,7,7a-tetrahydro-4aH-spiro[cyclopenta[c]pyran-1,2'-oxolane]-4'-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202002D          

 38 42  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652304292202002D          

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   -0.0980   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309   -1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454   -2.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165    0.1433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309    0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309    1.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454    0.1433    0.0000 C   0  0  0  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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 19  1  0  0  0  0
  4 20  1  6  0  0  0
  3 21  1  6  0  0  0
  1 22  1  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 26 33  1  0  0  0  0
 32 34  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078912

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@@]2(OC1(C)C)OC(C[C@]1(C)CCC3=C(O1)C=C(C)C=C3OC(C)=O)=C[C@@]1(C)CCC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C31H42O7/c1-19-14-24(34-20(2)32)23-10-13-29(7,37-25(23)15-19)17-22-16-28(6)11-9-12-30(28,8)31(36-22)18-26(35-21(3)33)27(4,5)38-31/h14-16,26H,9-13,17-18H2,1-8H3/t26-,28+,29-,30+,31-/m0/s1

> <INCHI_KEY>
VBJMVMOCCFVSFG-XICSTMNISA-N

> <FORMULA>
C31H42O7

> <MOLECULAR_WEIGHT>
526.67

> <EXACT_MASS>
526.293053692

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
58.50705513303075

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4'S,4aR,7aR)-3-{[(2S)-5-(acetyloxy)-2,7-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]methyl}-4a,5',5',7a-tetramethyl-5,6,7,7a-tetrahydro-4aH-spiro[cyclopenta[c]pyran-1,2'-oxolane]-4'-yl acetate

> <ALOGPS_LOGP>
6.96

> <JCHEM_LOGP>
5.782731178999999

> <ALOGPS_LOGS>
-6.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.188616131709122

> <JCHEM_POLAR_SURFACE_AREA>
80.29000000000002

> <JCHEM_REFRACTIVITY>
143.363

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.09e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4'S,4aR,7aR)-3-{[(2S)-5-(acetyloxy)-2,7-dimethyl-3,4-dihydro-1-benzopyran-2-yl]methyl}-4a,5',5',7a-tetramethyl-6,7-dihydro-5H-spiro[cyclopenta[c]pyran-1,2'-oxolane]-4'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -2.387  -6.209   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.870  -5.942   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.119  -7.122   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.407  -8.569   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.924  -8.836   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.914  -7.657   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.063 -10.113   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.011 -11.327   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.458 -10.800   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.404  -9.261   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.735 -11.661   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.119 -10.986   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.226  -9.450   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -7.396 -11.847   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.368 -12.825   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.914 -12.408   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.806  -9.517   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.083  -8.656   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.658  -7.175   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.300 -10.105   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.794  -5.738   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.377  -5.030   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.850  -3.583   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.367  -3.315   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.517  -4.353   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.183  -3.583   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.183  -2.043   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.517  -1.273   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.850  -2.043   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.151  -1.273   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.484  -2.043   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.484  -3.583   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.151  -4.353   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.818  -4.353   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.151   0.267   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.484   1.037   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.484   2.577   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.818   0.267   0.000  0.00  0.00           C+0
CONECT    1    2    6   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   19   21                                             
CONECT    4    3    5   17   20                                             
CONECT    5    4    6    7   10                                             
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   15   16                                             
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    8                                                            
CONECT   16    8                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    3                                                       
CONECT   20    4                                                            
CONECT   21    3                                                            
CONECT   22    1   23                                                       
CONECT   23   22   24   25   29                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28   23                                                       
CONECT   30   27   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32   26                                                       
CONECT   34   32                                                            
CONECT   35   30   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(1S,4's,4AR,7ar)-3-{[(2S)-5-(acetyloxy)-2,7-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]methyl}-4a,5',5',7a-tetramethyl-5,6,7,7a-tetrahydro-4ah-spiro[cyclopenta[c]pyran-1,2'-oxolane]-4'-yl acetic acid	Generator

Chemical Formula

C₃₁H₄₂O₇

Average Mass

526.6700 Da

Monoisotopic Mass

526.29305 Da

IUPAC Name

(1S,4'S,4aR,7aR)-3-{[(2S)-5-(acetyloxy)-2,7-dimethyl-3,4-dihydro-2H-1-benzopyran-2-yl]methyl}-4a,5',5',7a-tetramethyl-5,6,7,7a-tetrahydro-4aH-spiro[cyclopenta[c]pyran-1,2'-oxolane]-4'-yl acetate

Traditional Name

(1S,4'S,4aR,7aR)-3-{[(2S)-5-(acetyloxy)-2,7-dimethyl-3,4-dihydro-1-benzopyran-2-yl]methyl}-4a,5',5',7a-tetramethyl-6,7-dihydro-5H-spiro[cyclopenta[c]pyran-1,2'-oxolane]-4'-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@]2(OC1(C)C)OC(C[C@]1(C)CCC3=C(O1)C=C(C)C=C3OC(C)=O)=C[C@@]1(C)CCC[C@@]21C

InChI Identifier

InChI=1S/C31H42O7/c1-19-14-24(34-20(2)32)23-10-13-29(7,37-25(23)15-19)17-22-16-28(6)11-9-12-30(28,8)31(36-22)18-26(35-21(3)33)27(4,5)38-31/h14-16,26H,9-13,17-18H2,1-8H3/t26-,28+,29-,30+,31-/m0/s1

InChI Key

VBJMVMOCCFVSFG-XICSTMNISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cystoseira sp.	Algae	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Ketal
Alkyl aryl ether
Benzenoid
Monosaccharide
Dicarboxylic acid or derivatives
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	6.96	ALOGPS
logP	5.78	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	80.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	143.36 m³·mol⁻¹	ChemAxon
Polarizability	58.51 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

162903151

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Amentol chromane diacetate (NP0078912)

MOL for NP0078912 ((+)-Amentol chromane diacetate)

3D MOL for NP0078912 ((+)-Amentol chromane diacetate)

3D SDF for NP0078912 ((+)-Amentol chromane diacetate)

3D-SDF for NP0078912 ((+)-Amentol chromane diacetate)

PDB for NP0078912 ((+)-Amentol chromane diacetate)

3D PDB for NP0078912 ((+)-Amentol chromane diacetate)

SMILES for NP0078912 ((+)-Amentol chromane diacetate)

INCHI for NP0078912 ((+)-Amentol chromane diacetate)

Structure for NP0078912 ((+)-Amentol chromane diacetate)

3D Structure for NP0078912 ((+)-Amentol chromane diacetate)