NP-MRD: Showing NP-Card for Lactoside B (NP0073601)

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Record Information

Version

2.0

Created at

2022-04-28 18:49:35 UTC

Updated at

2022-04-28 18:49:35 UTC

NP-MRD ID

NP0073601

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lactoside B

Description

(1S,8R,9S,12S,14R,16R)-8-hydroxy-1,12-dimethyl-6-(propan-2-yl)-14-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-2,6-diene-4,11-dione belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Lactoside B is found in Lactuca laciniata Roth, Notoseris gracilipes C. Shih and Notoseris psilolepis C. Shih. Based on a literature review very few articles have been published on (1S,8R,9S,12S,14R,16R)-8-hydroxy-1,12-dimethyl-6-(propan-2-yl)-14-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-2,6-diene-4,11-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220492D          

 36 40  0  0  1  0            999 V2000
    1.1355    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.3509   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3509    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.7079    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2 13  1  0  0  0  0
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  5 27  1  1  0  0  0
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  3 35  2  0  0  0  0
  2 36  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282220492D          

 36 40  0  0  1  0            999 V2000
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 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  1  0  0  0
 21 22  1  0  0  0  0
 18 23  1  6  0  0  0
 17 24  1  1  0  0  0
 16 25  1  6  0  0  0
 10 26  1  6  0  0  0
  5 27  1  1  0  0  0
  4 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 28 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  3 35  2  0  0  0  0
  2 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0073601

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2[C@@H](O)[C@H]3OC(=O)[C@@]4(C)C[C@@H](C[C@@](C)([C@@H]34)C2=CC(=O)O1)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O11/c1-9(2)19-14-11(5-13(27)35-19)24(3)6-10(7-25(4)21(24)20(16(14)29)36-23(25)32)33-22-18(31)17(30)15(28)12(8-26)34-22/h5,9-10,12,15-18,20-22,26,28-31H,6-8H2,1-4H3/t10-,12-,15-,16-,17+,18-,20-,21-,22-,24-,25+/m1/s1

> <INCHI_KEY>
WXRVPRKVIDFJHO-KCCYGGLPSA-N

> <FORMULA>
C25H34O11

> <MOLECULAR_WEIGHT>
510.536

> <EXACT_MASS>
510.210111915

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.762298404358546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,8R,9S,12S,14R,16R)-8-hydroxy-1,12-dimethyl-6-(propan-2-yl)-14-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,10-dioxatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2,6-diene-4,11-dione

> <ALOGPS_LOGP>
0.05

> <JCHEM_LOGP>
-0.8948640293333335

> <ALOGPS_LOGS>
-2.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.017553515347089

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.18387420313357

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835415469468

> <JCHEM_POLAR_SURFACE_AREA>
172.21

> <JCHEM_REFRACTIVITY>
121.97759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,8R,9S,12S,14R,16R)-8-hydroxy-6-isopropyl-1,12-dimethyl-14-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,10-dioxatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2,6-diene-4,11-dione

> <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       2.120   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.787  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.655  -0.476   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.790   0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.479   4.553   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.159   6.059   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.306   6.535   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.450   5.504   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.915   5.980   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.235   7.487   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.090   8.517   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.626   8.041   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.411  10.024   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.875  10.499   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.699   7.963   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.059   4.950   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.130   3.998   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.851   2.336   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.453  -2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.787  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.454  -0.000   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.788   2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.666   3.259   0.000  0.00  0.00           C+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3   13   36                                             
CONECT    3    2    4   35                                                  
CONECT    4    3    5   28                                                  
CONECT    5    4    6   27                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    1   11   26                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    2                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   15                                                       
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   18                                                            
CONECT   24   17                                                            
CONECT   25   16                                                            
CONECT   26   10                                                            
CONECT   27    5                                                            
CONECT   28    4   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    3                                                       
CONECT   36    2                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄O₁₁

Average Mass

510.5360 Da

Monoisotopic Mass

510.21011 Da

IUPAC Name

Traditional Name

(1S,8R,9S,12S,14R,16R)-8-hydroxy-6-isopropyl-1,12-dimethyl-14-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,10-dioxatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2,6-diene-4,11-dione

CAS Registry Number

Not Available

SMILES

CC(C)C1=C2[C@@H](O)[C@H]3OC(=O)[C@@]4(C)C[C@@H](C[C@@](C)([C@@H]34)C2=CC(=O)O1)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C25H34O11/c1-9(2)19-14-11(5-13(27)35-19)24(3)6-10(7-25(4)21(24)20(16(14)29)36-23(25)32)33-22-18(31)17(30)15(28)12(8-26)34-22/h5,9-10,12,15-18,20-22,26,28-31H,6-8H2,1-4H3/t10-,12-,15-,16-,17+,18-,20-,21-,22-,24-,25+/m1/s1

InChI Key

WXRVPRKVIDFJHO-KCCYGGLPSA-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
Lactuca laciniata Roth	Plant	KNApSAcK
Notoseris gracilipes C. Shih	Plant	KNApSAcK
Notoseris psilolepis C. Shih	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Naphthalene
Pyranone
Pyran
Oxane
Monosaccharide
Gamma butyrolactone
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
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	0.05	ALOGPS
logP	-0.89	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.98 m³·mol⁻¹	ChemAxon
Polarizability	51.76 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	No	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

163084023

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lactoside B (NP0073601)

MOL for NP0073601 (Lactoside B)

3D MOL for NP0073601 (Lactoside B)

3D SDF for NP0073601 (Lactoside B)

3D-SDF for NP0073601 (Lactoside B)

PDB for NP0073601 (Lactoside B)

3D PDB for NP0073601 (Lactoside B)

SMILES for NP0073601 (Lactoside B)

INCHI for NP0073601 (Lactoside B)

Structure for NP0073601 (Lactoside B)

3D Structure for NP0073601 (Lactoside B)