NP-MRD: Showing NP-Card for Laurycolactone B (NP0140592)

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Record Information

Version

2.0

Created at

2022-06-29 21:42:07 UTC

Updated at

2022-06-29 21:42:07 UTC

NP-MRD ID

NP0140592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Laurycolactone B

Description

Laurycolactone B belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. Laurycolactone B is found in Eurycoma longifolia. Laurycolactone B was first documented in 2002 (PMID: 11937162). Based on a literature review very few articles have been published on Laurycolactone B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
    4.5844    0.2616    1.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4257    0.5144    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5021    0.8964   -0.8697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1113    1.0140   -1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7128    1.7759   -2.2642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3546    0.0415   -0.5137 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6968   -1.3167   -0.9858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0371    0.3756    0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906    0.4970    1.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0536    0.3199    2.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6843    0.6302    3.0296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7326   -0.2532    0.8251 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6011   -1.7449    0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2002    0.1069    0.8889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2823    1.5719    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118    2.4274    1.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431    1.7797   -0.7132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3413    0.5235   -1.4032 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9098   -0.4080   -0.3449 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3949   -0.0926   -0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8727    0.2515   -1.6391 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7614   -0.9137   -2.3383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1030    0.3655   -0.3748 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3538    0.6987    2.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8028   -0.8087    1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5008    0.7242    0.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4094    1.0813   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3818   -1.2697   -1.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8863   -2.0289   -1.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570   -1.7896   -0.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9284    0.7403    2.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1792   -1.9998    1.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819   -2.3315    0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4387   -2.0711    1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6710   -0.2120    1.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9003    0.5113   -2.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7668   -1.4601   -0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7563    0.5088   -1.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6552    0.3855    0.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9667   -1.0566   -0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5203    1.0814   -2.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6779   -0.8045   -3.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1064    1.4819   -0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 12  1  0
 12 13  1  6
 12 23  1  0
 23 21  1  0
 21 22  1  0
 23  6  1  0
  6  7  1  6
  6  4  1  0
  4  5  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 14 19  1  0
 10 12  1  0
 21 18  1  0
  8  6  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 19 37  1  6
 18 36  1  6
 14 35  1  1
 13 32  1  0
 13 33  1  0
 13 34  1  0
 23 43  1  1
 21 41  1  6
 22 42  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  3 27  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  9 31  1  0
M  END


  Mrv1652306292223422D          

 23 26  0  0  1  0            999 V2000
    6.1112   -1.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2863   -1.5488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0420   -0.6251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2402   -0.8196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8924   -1.5677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2604   -2.3061    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0672   -2.4787    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7051   -1.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4532   -2.3034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6939   -1.1307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8050   -2.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1730   -3.7324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9816   -2.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6135   -2.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0690   -1.5173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5555   -0.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7760   -0.0766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7827   -1.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186   -1.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1729   -2.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500   -0.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5723   -3.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7171   -0.1817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  3 10  1  6  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 21  1  1  0  0  0
  6 22  1  1  0  0  0
  4 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0140592

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O5/c1-7-5-10(19)17(3)9(7)6-11(20)18(4)12-8(2)14(23-16(12)22)13(21)15(17)18/h5-6,8,12-15,21H,1-4H3/t8-,12-,13+,14-,15-,17-,18+/m1/s1

> <INCHI_KEY>
CHTGFNQFMFSMRT-SGRYNZJISA-N

> <FORMULA>
C18H20O5

> <MOLECULAR_WEIGHT>
316.353

> <EXACT_MASS>
316.131073744

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      11.408  -2.870   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.868  -2.891   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.412  -1.167   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.915  -1.530   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.266  -2.926   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.953  -4.305   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.459  -4.627   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.650  -3.650   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.046  -4.300   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      10.629  -2.111   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.103  -5.589   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.790  -6.967   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.566  -5.495   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.879  -4.116   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.729  -2.832   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.770  -1.627   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.182  -0.143   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.328  -2.166   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.395  -3.705   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.189  -4.663   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.440  -1.466   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.535  -5.730   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.939  -0.339   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7   11   22                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3                                                       
CONECT   11    6   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14    5   16   21                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19                                                            
CONECT   21   15                                                            
CONECT   22    6                                                            
CONECT   23    4                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₀O₅

Average Mass

316.3530 Da

Monoisotopic Mass

316.13107 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2OC(=O)[C@@H]1[C@@]1(C)[C@H]([C@H]2O)[C@@]2(C)C(=O)C=C(C)C2=CC1=O

InChI Identifier

InChI=1S/C18H20O5/c1-7-5-10(19)17(3)9(7)6-11(20)18(4)12-8(2)14(23-16(12)22)13(21)15(17)18/h5-6,8,12-15,21H,1-4H3/t8-,12-,13+,14-,15-,17-,18+/m1/s1

InChI Key

CHTGFNQFMFSMRT-SGRYNZJISA-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
Eurycoma longifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

C-18 quassinoid skeleton
Caprolactone
Cyclohexenone
Oxepane
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organooxygen compound
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

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

24660540

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46878903

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ang HH, Hitotsuyanagi Y, Fukaya H, Takeya K: Quassinoids from Eurycoma longifolia. Phytochemistry. 2002 Apr;59(8):833-7. doi: 10.1016/s0031-9422(01)00480-0. [PubMed:11937162 ]

Showing NP-Card for Laurycolactone B (NP0140592)

MOL for NP0140592 (Laurycolactone B)

3D MOL for NP0140592 (Laurycolactone B)

3D SDF for NP0140592 (Laurycolactone B)

3D-SDF for NP0140592 (Laurycolactone B)

PDB for NP0140592 (Laurycolactone B)

3D PDB for NP0140592 (Laurycolactone B)

SMILES for NP0140592 (Laurycolactone B)

INCHI for NP0140592 (Laurycolactone B)

Structure for NP0140592 (Laurycolactone B)

3D Structure for NP0140592 (Laurycolactone B)