NP-MRD: Showing NP-Card for (1ar,3ar,4r,5s,7s,7ar,7bs)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-5-hydroxy-7a-(hydroxymethyl)-1a,4,7b-trimethyl-hexahydronaphtho[1,2-b]oxiren-7-yl benzoate (NP0157749)

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Record Information

Version

2.0

Created at

2022-09-02 15:12:02 UTC

Updated at

2022-09-02 15:12:02 UTC

NP-MRD ID

NP0157749

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1ar,3ar,4r,5s,7s,7ar,7bs)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-5-hydroxy-7a-(hydroxymethyl)-1a,4,7b-trimethyl-hexahydronaphtho[1,2-b]oxiren-7-yl benzoate

Description

Scuterivulactone A belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Based on a literature review very few articles have been published on Scuterivulactone A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217122D          

 38 42  0  0  1  0            999 V2000
    6.2844   -1.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4975   -0.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4484    0.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9611    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022217122D          

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  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 13  5  1  6  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 13 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 34 37  1  0  0  0  0
 28 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0157749

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H](CC1=CC(=O)OC1)[C@@]1(C)[C@@H](O)C[C@H](OC(=O)C2=CC=CC=C2)[C@]2(CO)[C@@H]1CC[C@@]1(C)O[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O9/c1-17(31)36-22(12-18-13-24(33)35-15-18)27(3)20-10-11-26(2)28(4,38-26)29(20,16-30)23(14-21(27)32)37-25(34)19-8-6-5-7-9-19/h5-9,13,20-23,30,32H,10-12,14-16H2,1-4H3/t20-,21+,22+,23+,26-,27-,28-,29+/m1/s1

> <INCHI_KEY>
OROSEBUCDUVSEX-ARBBAGNKSA-N

> <FORMULA>
C29H36O9

> <MOLECULAR_WEIGHT>
528.598

> <EXACT_MASS>
528.235932739

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.456927408183276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1aS,1bR,2S,4S,5R,5aR,7aR)-5-[(1S)-1-(acetyloxy)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-4-hydroxy-1b-(hydroxymethyl)-1a,5,7a-trimethyl-decahydronaphtho[1,2-b]oxiren-2-yl benzoate

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
2.177795034333333

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.387027931538313

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.105384425521819

> <JCHEM_PKA_STRONGEST_BASIC>
-2.83074703851739

> <JCHEM_POLAR_SURFACE_AREA>
131.89000000000001

> <JCHEM_REFRACTIVITY>
135.2234

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1aS,1bR,2S,4S,5R,5aR,7aR)-5-[(1S)-1-(acetyloxy)-2-(5-oxo-2H-furan-3-yl)ethyl]-4-hydroxy-1b-(hydroxymethyl)-1a,5,7a-trimethyl-hexahydronaphtho[1,2-b]oxiren-2-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      11.731  -2.711   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.445  -3.559   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.537  -5.096   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.068  -2.870   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.977  -1.332   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.262  -0.484   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.170   1.053   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.873   1.882   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.261   3.373   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.347   4.132   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      10.798   3.464   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.360   2.031   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.599  -0.643   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.160  -2.119   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.517   0.593   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.047   0.417   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.905   2.007   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.376   2.183   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.764   3.596   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.682   4.833   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.211   4.656   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.070   6.246   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.540   6.423   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.928   7.836   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.846   9.073   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.376   8.896   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.987   7.483   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.458   0.947   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.846   2.360   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.316   2.537   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.070  -0.467   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.152  -1.703   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.622  -1.526   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.010  -0.113   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.597  -0.725   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.398   1.300   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.928   1.123   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.794   2.165   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    7                                                       
CONECT   13    5   14   15   31                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   18   29   31   37                                             
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   13   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   34   28   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₉

Average Mass

528.5980 Da

Monoisotopic Mass

528.23593 Da

IUPAC Name

(1aS,1bR,2S,4S,5R,5aR,7aR)-5-[(1S)-1-(acetyloxy)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-4-hydroxy-1b-(hydroxymethyl)-1a,5,7a-trimethyl-decahydronaphtho[1,2-b]oxiren-2-yl benzoate

Traditional Name

(1aS,1bR,2S,4S,5R,5aR,7aR)-5-[(1S)-1-(acetyloxy)-2-(5-oxo-2H-furan-3-yl)ethyl]-4-hydroxy-1b-(hydroxymethyl)-1a,5,7a-trimethyl-hexahydronaphtho[1,2-b]oxiren-2-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H](CC1=CC(=O)OC1)[C@@]1(C)[C@@H](O)C[C@H](OC(=O)C2=CC=CC=C2)[C@]2(CO)[C@@H]1CC[C@@]1(C)O[C@@]21C

InChI Identifier

InChI=1S/C29H36O9/c1-17(31)36-22(12-18-13-24(33)35-15-18)27(3)20-10-11-26(2)28(4,38-26)29(20,16-30)23(14-21(27)32)37-25(34)19-8-6-5-7-9-19/h5-9,13,20-23,30,32H,10-12,14-16H2,1-4H3/t20-,21+,22+,23+,26-,27-,28-,29+/m1/s1

InChI Key

OROSEBUCDUVSEX-ARBBAGNKSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Tricarboxylic acid or derivatives
Benzoyl
Oxepane
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	2.56	ALOGPS
logP	2.18	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	131.89 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	135.22 m³·mol⁻¹	ChemAxon
Polarizability	54.46 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

C00024036

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

101661883

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1ar,3ar,4r,5s,7s,7ar,7bs)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-5-hydroxy-7a-(hydroxymethyl)-1a,4,7b-trimethyl-hexahydronaphtho[1,2-b]oxiren-7-yl benzoate (NP0157749)

MOL for NP0157749 ((1ar,3ar,4r,5s,7s,7ar,7bs)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-5-hydroxy-7a-(hydroxymethyl)-1a,4,7b-trimethyl-hexahydronaphtho[1,2-b]oxiren-7-yl benzoate)

3D MOL for NP0157749 ((1ar,3ar,4r,5s,7s,7ar,7bs)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-5-hydroxy-7a-(hydroxymethyl)-1a,4,7b-trimethyl-hexahydronaphtho[1,2-b]oxiren-7-yl benzoate)

3D SDF for NP0157749 ((1ar,3ar,4r,5s,7s,7ar,7bs)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-5-hydroxy-7a-(hydroxymethyl)-1a,4,7b-trimethyl-hexahydronaphtho[1,2-b]oxiren-7-yl benzoate)

3D-SDF for NP0157749 ((1ar,3ar,4r,5s,7s,7ar,7bs)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-5-hydroxy-7a-(hydroxymethyl)-1a,4,7b-trimethyl-hexahydronaphtho[1,2-b]oxiren-7-yl benzoate)

PDB for NP0157749 ((1ar,3ar,4r,5s,7s,7ar,7bs)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-5-hydroxy-7a-(hydroxymethyl)-1a,4,7b-trimethyl-hexahydronaphtho[1,2-b]oxiren-7-yl benzoate)

3D PDB for NP0157749 ((1ar,3ar,4r,5s,7s,7ar,7bs)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-5-hydroxy-7a-(hydroxymethyl)-1a,4,7b-trimethyl-hexahydronaphtho[1,2-b]oxiren-7-yl benzoate)

SMILES for NP0157749 ((1ar,3ar,4r,5s,7s,7ar,7bs)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-5-hydroxy-7a-(hydroxymethyl)-1a,4,7b-trimethyl-hexahydronaphtho[1,2-b]oxiren-7-yl benzoate)

INCHI for NP0157749 ((1ar,3ar,4r,5s,7s,7ar,7bs)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-5-hydroxy-7a-(hydroxymethyl)-1a,4,7b-trimethyl-hexahydronaphtho[1,2-b]oxiren-7-yl benzoate)

Structure for NP0157749 ((1ar,3ar,4r,5s,7s,7ar,7bs)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-5-hydroxy-7a-(hydroxymethyl)-1a,4,7b-trimethyl-hexahydronaphtho[1,2-b]oxiren-7-yl benzoate)

3D Structure for NP0157749 ((1ar,3ar,4r,5s,7s,7ar,7bs)-4-[(1s)-1-(acetyloxy)-2-(5-oxo-2h-furan-3-yl)ethyl]-5-hydroxy-7a-(hydroxymethyl)-1a,4,7b-trimethyl-hexahydronaphtho[1,2-b]oxiren-7-yl benzoate)