NP-MRD: Showing NP-Card for Scuterivulactone A (NP0066484)

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Record Information

Version

2.0

Created at

2022-04-28 10:44:56 UTC

Updated at

2022-04-28 10:44:56 UTC

NP-MRD ID

NP0066484

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Scuterivulactone A

Description

(1AS,1bS,2S,4S,5S,5aR,7aR)-5-[(1S)-1-(acetyloxy)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-4-hydroxy-1a,1b,4,5-tetramethyl-decahydronaphtho[1,2-b]oxiren-2-yl benzoate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Scuterivulactone A is found in Scutellaria rivularis Wall. . Based on a literature review very few articles have been published on (1aS,1bS,2S,4S,5S,5aR,7aR)-5-[(1S)-1-(acetyloxy)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-4-hydroxy-1a,1b,4,5-tetramethyl-decahydronaphtho[1,2-b]oxiren-2-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212442D          

 37 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282212442D          

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 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  6  0  0  0
 17 20  1  6  0  0  0
 16 20  1  0  0  0  0
 16 21  1  1  0  0  0
  5 22  1  6  0  0  0
  3 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 23 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  3 35  1  6  0  0  0
  2 36  1  6  0  0  0
  2 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0066484

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H](CC1=CC(=O)OC1)[C@]1(C)[C@H]2CC[C@H]3O[C@@]3(C)[C@]2(C)[C@H](C[C@]1(C)O)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O8/c1-17(30)35-22(13-18-14-24(31)34-16-18)27(3)20-11-12-21-29(5,37-21)28(20,4)23(15-26(27,2)33)36-25(32)19-9-7-6-8-10-19/h6-10,14,20-23,33H,11-13,15-16H2,1-5H3/t20-,21-,22+,23+,26+,27+,28+,29-/m1/s1

> <INCHI_KEY>
AMHXSCQUXNYYCR-XXEZFEIISA-N

> <FORMULA>
C29H36O8

> <MOLECULAR_WEIGHT>
512.599

> <EXACT_MASS>
512.241018119

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.808791244835064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
3.458566190999999

> <ALOGPS_LOGS>
-5.48

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.400349128614426

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.105245050757551

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0611377901677717

> <JCHEM_POLAR_SURFACE_AREA>
111.66000000000001

> <JCHEM_REFRACTIVITY>
133.4487

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.68e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.238   1.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.850   2.487   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.932   3.723   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.402   3.547   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.790   2.133   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.708   0.897   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.096  -0.516   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.014  -1.753   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.402  -3.166   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.544  -1.576   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.156  -0.163   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.686   0.014   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.604  -1.223   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.992  -2.636   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.462  -2.813   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.260   1.957   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.343   3.193   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.955   4.606   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.484   4.783   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.269   1.780   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.437   0.427   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.178   0.720   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.136   4.684   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.570   4.121   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.773   5.082   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.704   6.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.145   7.162   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.555   8.646   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      11.106   5.958   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.258   4.673   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.906   6.206   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.472   6.769   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.268   5.808   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.242   8.291   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.809   5.258   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.284   1.924   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       7.118   3.361   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   36   37                                             
CONECT    3    2    4   23   35                                             
CONECT    4    3    5   19                                                  
CONECT    5    4    6   16   22                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    5   17   20   21                                             
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18    4                                                       
CONECT   20   17   16                                                       
CONECT   21   16                                                            
CONECT   22    5                                                            
CONECT   23    3   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   25                                                       
CONECT   31   23   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35    3                                                            
CONECT   36    2                                                            
CONECT   37    2                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
(1AS,1BS,2S,4S,5S,5ar,7ar)-5-[(1S)-1-(acetyloxy)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-4-hydroxy-1a,1b,4,5-tetramethyl-decahydronaphtho[1,2-b]oxiren-2-yl benzoic acid	Generator

Chemical Formula

C₂₉H₃₆O₈

Average Mass

512.5990 Da

Monoisotopic Mass

512.24102 Da

IUPAC Name

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

Traditional Name

(1aS,1bS,2S,4S,5S,5aR,7aR)-5-[(1S)-1-(acetyloxy)-2-(5-oxo-2H-furan-3-yl)ethyl]-4-hydroxy-1a,1b,4,5-tetramethyl-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]2CC[C@H]3O[C@@]3(C)[C@]2(C)[C@H](C[C@]1(C)O)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C29H36O8/c1-17(30)35-22(13-18-14-24(31)34-16-18)27(3)20-11-12-21-29(5,37-21)28(20,4)23(15-26(27,2)33)36-25(32)19-9-7-6-8-10-19/h6-10,14,20-23,33H,11-13,15-16H2,1-5H3/t20-,21-,22+,23+,26+,27+,28+,29-/m1/s1

InChI Key

AMHXSCQUXNYYCR-XXEZFEIISA-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
Scutellaria rivularis Wall.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Oxepane
Monocyclic benzene moiety
2-furanone
Benzenoid
Dihydrofuran
Cyclic alcohol
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Dialkyl ether
Oxirane
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	3.55	ALOGPS
logP	3.46	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.66 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	133.45 m³·mol⁻¹	ChemAxon
Polarizability	53.81 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

Not Available

Chemspider ID

9974589

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11799919

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Scuterivulactone A (NP0066484)

MOL for NP0066484 (Scuterivulactone A)

3D MOL for NP0066484 (Scuterivulactone A)

3D SDF for NP0066484 (Scuterivulactone A)

3D-SDF for NP0066484 (Scuterivulactone A)

PDB for NP0066484 (Scuterivulactone A)

3D PDB for NP0066484 (Scuterivulactone A)

SMILES for NP0066484 (Scuterivulactone A)

INCHI for NP0066484 (Scuterivulactone A)

Structure for NP0066484 (Scuterivulactone A)

3D Structure for NP0066484 (Scuterivulactone A)