NP-MRD: Showing NP-Card for Alboleersin (NP0066348)

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Record Information

Version

2.0

Created at

2022-04-28 10:37:41 UTC

Updated at

2022-04-28 10:37:42 UTC

NP-MRD ID

NP0066348

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Alboleersin

Description

(2R,3S,4R)-2-[(2R,4aR,4bS,5S,10aR,12aR)-5,6,9-trihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-2,3,4,4a,4b,5,10a,11,12,12a-decahydro-1,10-dioxatetraphen-8-yl]-4-methylhexan-3-yl acetate belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring. Alboleersin is found in Cochliobolus miyabeanus and Leersia virginica. Based on a literature review very few articles have been published on (2R,3S,4R)-2-[(2R,4aR,4bS,5S,10aR,12aR)-5,6,9-trihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-2,3,4,4a,4b,5,10a,11,12,12a-decahydro-1,10-dioxatetraphen-8-yl]-4-methylhexan-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212372D          

 38 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282212372D          

 38 41  0  0  1  0            999 V2000
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    0.4125   -6.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -8.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4302   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 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
 14 19  1  6  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 15 24  1  6  0  0  0
 10 25  1  6  0  0  0
  8 26  1  1  0  0  0
  3 27  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 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
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0066348

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)[C@H](OC(C)=O)[C@H](C)C1=CC(O)=C2[C@@H](O)[C@H]3[C@@](C)(CC[C@H]4O[C@H](CC[C@]34C)C(C)(C)O)OC2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O8/c1-9-15(2)25(36-17(4)31)16(3)18-14-19(32)22-24(34)27-29(7)12-10-20(28(5,6)35)37-21(29)11-13-30(27,8)38-26(22)23(18)33/h14-16,20-21,24-25,27,32-35H,9-13H2,1-8H3/t15-,16-,20-,21-,24-,25+,27-,29+,30-/m1/s1

> <INCHI_KEY>
UQNKLYUSWJMMQQ-ZERWNYGASA-N

> <FORMULA>
C30H46O8

> <MOLECULAR_WEIGHT>
534.69

> <EXACT_MASS>
534.319268441

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
60.09248563351373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R)-2-[(2R,4aR,4bS,5S,10aR,12aR)-5,6,9-trihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-2,3,4,4a,4b,5,10a,11,12,12a-decahydro-1,10-dioxatetraphen-8-yl]-4-methylhexan-3-yl acetate

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
4.182419186333333

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.681158004164606

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.827770307662597

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0935564768373824

> <JCHEM_POLAR_SURFACE_AREA>
125.68

> <JCHEM_REFRACTIVITY>
143.05040000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R)-2-[(2R,4aR,4bS,5S,10aR,12aR)-5,6,9-trihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphen-8-yl]-4-methylhexan-3-yl acetate

> <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      -8.002  -6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336  -8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.335  -6.160   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -8.002 -10.780   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.668 -13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001 -13.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334 -13.090   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.770 -12.526   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.770 -15.194   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.001  -8.470   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0     -10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -12.003  -3.850   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -13.337  -1.540   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   28                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   26                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12   25                                             
CONECT   11   10    4                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14    9   16   24                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   15                                                            
CONECT   25   10                                                            
CONECT   26    8                                                            
CONECT   27    3                                                            
CONECT   28    2   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   30   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S,4R)-2-[(2R,4AR,4BS,5S,10ar,12ar)-5,6,9-trihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-2,3,4,4a,4b,5,10a,11,12,12a-decahydro-1,10-dioxatetraphen-8-yl]-4-methylhexan-3-yl acetic acid	Generator

Chemical Formula

C₃₀H₄₆O₈

Average Mass

534.6900 Da

Monoisotopic Mass

534.31927 Da

IUPAC Name

(2R,3S,4R)-2-[(2R,4aR,4bS,5S,10aR,12aR)-5,6,9-trihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-2,3,4,4a,4b,5,10a,11,12,12a-decahydro-1,10-dioxatetraphen-8-yl]-4-methylhexan-3-yl acetate

Traditional Name

(2R,3S,4R)-2-[(2R,4aR,4bS,5S,10aR,12aR)-5,6,9-trihydroxy-2-(2-hydroxypropan-2-yl)-4a,10a-dimethyl-2,3,4,4b,5,11,12,12a-octahydro-1,10-dioxatetraphen-8-yl]-4-methylhexan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)[C@H](OC(C)=O)[C@H](C)C1=CC(O)=C2[C@@H](O)[C@H]3[C@@](C)(CC[C@H]4O[C@H](CC[C@]34C)C(C)(C)O)OC2=C1O

InChI Identifier

InChI=1S/C30H46O8/c1-9-15(2)25(36-17(4)31)16(3)18-14-19(32)22-24(34)27-29(7)12-10-20(28(5,6)35)37-21(29)11-13-30(27,8)38-26(22)23(18)33/h14-16,20-21,24-25,27,32-35H,9-13H2,1-8H3/t15-,16-,20-,21-,24-,25+,27-,29+,30-/m1/s1

InChI Key

UQNKLYUSWJMMQQ-ZERWNYGASA-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
Bipolaris oryzae	Fungi	KNApSAcK
Leersia virginica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthenes

Alternative Parents

Substituents

Xanthene
Prenylbenzoquinol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxane
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	4.1	ALOGPS
logP	4.18	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.83	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	143.05 m³·mol⁻¹	ChemAxon
Polarizability	60.09 Å³	ChemAxon
Number of Rings	4	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

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

162844981

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Alboleersin (NP0066348)

MOL for NP0066348 (Alboleersin)

3D MOL for NP0066348 (Alboleersin)

3D SDF for NP0066348 (Alboleersin)

3D-SDF for NP0066348 (Alboleersin)

PDB for NP0066348 (Alboleersin)

3D PDB for NP0066348 (Alboleersin)

SMILES for NP0066348 (Alboleersin)

INCHI for NP0066348 (Alboleersin)

Structure for NP0066348 (Alboleersin)

3D Structure for NP0066348 (Alboleersin)