NP-MRD: Showing NP-Card for Lamellarin alpha (NP0079134)

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Record Information

Version

2.0

Created at

2022-04-29 00:11:23 UTC

Updated at

2022-04-29 00:11:23 UTC

NP-MRD ID

NP0079134

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lamellarin alpha

Description

Lamellarin alpha 20-hydrogen sulfate, also known as lamellarin α 20-hydrogen sulphuric acid, belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond. Lamellarin alpha is found in Didemnum obscurum. Based on a literature review very few articles have been published on lamellarin alpha 20-hydrogen sulfate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202112D          

 42 47  0  0  0  0            999 V2000
    2.9959    0.2706    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


  Mrv1652304292202112D          

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  6 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 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
 21 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  2  0  0  0  0
 28 31  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
  1 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 38 40  1  0  0  0  0
 37 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079134

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1O)C1=C2N(C=CC3=CC(OC)=C(OC)C=C23)C2=C1C1=CC(OC)=C(OS(O)(=O)=O)C=C1OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H23NO11S/c1-36-19-6-5-15(9-18(19)31)25-26-17-12-23(39-4)24(41-42(33,34)35)13-20(17)40-29(32)28(26)30-8-7-14-10-21(37-2)22(38-3)11-16(14)27(25)30/h5-13,31H,1-4H3,(H,33,34,35)

> <INCHI_KEY>
JMOHRMCZYHDLSW-UHFFFAOYSA-N

> <FORMULA>
C29H23NO11S

> <MOLECULAR_WEIGHT>
593.56

> <EXACT_MASS>
593.099181739

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
59.0542034793129

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[12-(3-hydroxy-4-methoxyphenyl)-8,16,17-trimethoxy-3-oxo-4-oxa-1-azapentacyclo[11.8.0.0^{2,11}.0^{5,10}.0^{14,19}]henicosa-2(11),5,7,9,12,14,16,18,20-nonaen-7-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
3.4054156116666663

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.697419134658833

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.955019928595874

> <JCHEM_PKA_STRONGEST_BASIC>
-4.303657513038097

> <JCHEM_POLAR_SURFACE_AREA>
151.45999999999998

> <JCHEM_REFRACTIVITY>
150.29209999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[12-(3-hydroxy-4-methoxyphenyl)-8,16,17-trimethoxy-3-oxo-4-oxa-1-azapentacyclo[11.8.0.0^{2,11}.0^{5,10}.0^{14,19}]henicosa-2(11),5,7,9,12,14,16,18,20-nonaen-7-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       5.592   0.505   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.346   1.410   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.822   2.875   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       6.362   2.875   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.838   1.410   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.344   1.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.375   2.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.899   3.699   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.393   4.019   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.881   1.914   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.357   0.450   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.327  -0.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.820  -0.374   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.803  -2.159   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.309  -2.479   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.864   0.130   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.339  -1.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.792   4.019   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.268   5.484   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.285   3.699   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.679   0.130   0.000  0.00  0.00           O+0
HETATM   28  S   UNK     0      -2.155  -1.335   0.000  0.00  0.00           S+0
HETATM   29  O   UNK     0      -3.620  -0.859   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.690  -1.811   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.631  -2.800   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.382  -2.159   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.412  -3.304   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.592  -1.035   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.926  -1.805   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.926  -3.345   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.592  -4.115   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.259  -3.345   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.259  -1.805   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.925  -4.115   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       5.592  -5.655   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.259  -6.425   0.000  0.00  0.00           C+0
CONECT    1    2    5   34                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    6                                                       
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   11   17                                                       
CONECT   17   16                                                            
CONECT   18    3   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21    2   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32   24   33                                                       
CONECT   33   32                                                            
CONECT   34    1   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   41                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38   34                                                       
CONECT   40   38                                                            
CONECT   41   37   42                                                       
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
Lamellarin a 20-hydrogen sulfate	Generator
Lamellarin a 20-hydrogen sulfuric acid	Generator
Lamellarin a 20-hydrogen sulphate	Generator
Lamellarin a 20-hydrogen sulphuric acid	Generator
Lamellarin alpha 20-hydrogen sulfuric acid	Generator
Lamellarin alpha 20-hydrogen sulphate	Generator
Lamellarin alpha 20-hydrogen sulphuric acid	Generator
Lamellarin α 20-hydrogen sulfate	Generator
Lamellarin α 20-hydrogen sulfuric acid	Generator
Lamellarin α 20-hydrogen sulphate	Generator
Lamellarin α 20-hydrogen sulphuric acid	Generator
Lamellarin alpha 20-sulfate	MeSH

Chemical Formula

C₂₉H₂₃NO₁₁S

Average Mass

593.5600 Da

Monoisotopic Mass

593.09918 Da

IUPAC Name

[12-(3-hydroxy-4-methoxyphenyl)-8,16,17-trimethoxy-3-oxo-4-oxa-1-azapentacyclo[11.8.0.0^{2,11}.0^{5,10}.0^{14,19}]henicosa-2(11),5,7,9,12,14,16,18,20-nonaen-7-yl]oxidanesulfonic acid

Traditional Name

[12-(3-hydroxy-4-methoxyphenyl)-8,16,17-trimethoxy-3-oxo-4-oxa-1-azapentacyclo[11.8.0.0^{2,11}.0^{5,10}.0^{14,19}]henicosa-2(11),5,7,9,12,14,16,18,20-nonaen-7-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1O)C1=C2N(C=CC3=CC(OC)=C(OC)C=C23)C2=C1C1=CC(OC)=C(OS(O)(=O)=O)C=C1OC2=O

InChI Identifier

InChI=1S/C29H23NO11S/c1-36-19-6-5-15(9-18(19)31)25-26-17-12-23(39-4)24(41-42(33,34)35)13-20(17)40-29(32)28(26)30-8-7-14-10-21(37-2)22(38-3)11-16(14)27(25)30/h5-13,31H,1-4H3,(H,33,34,35)

InChI Key

JMOHRMCZYHDLSW-UHFFFAOYSA-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
Didemnum obscurum	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroles

Sub Class

Substituted pyrroles

Direct Parent

Phenylpyrroles

Alternative Parents

Substituents

3-phenylpyrrole
Coumarin
1-benzopyran
Isoquinoline
Methoxyphenol
Benzopyran
Arylsulfate
Pyrrolopyridine
Indolizine
Phenoxy compound
Methoxybenzene
Anisole
Phenol ether
Phenol
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Sulfuric acid monoester
Pyridine
Pyran
Sulfate-ester
Sulfuric acid ester
Organic sulfuric acid or derivatives
Heteroaromatic compound
Lactone
Azacycle
Oxacycle
Ether
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:72792 )
alkaloid (CHEBI:72792 )
monomethoxybenzene (CHEBI:72792 )
delta-lactone (CHEBI:72792 )
heterocyclyl sulfate (CHEBI:72792 )

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	2.74	ALOGPS
logP	3.41	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	151.46 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	150.29 m³·mol⁻¹	ChemAxon
Polarizability	59.05 Å³	ChemAxon
Number of Rings	6	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

C00043646

Chemspider ID

418712

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

476994

PDB ID

Not Available

ChEBI ID

72792

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lamellarin alpha (NP0079134)

MOL for NP0079134 (Lamellarin alpha)

3D MOL for NP0079134 (Lamellarin alpha)

3D SDF for NP0079134 (Lamellarin alpha)

3D-SDF for NP0079134 (Lamellarin alpha)

PDB for NP0079134 (Lamellarin alpha)

3D PDB for NP0079134 (Lamellarin alpha)

SMILES for NP0079134 (Lamellarin alpha)

INCHI for NP0079134 (Lamellarin alpha)

Structure for NP0079134 (Lamellarin alpha)

3D Structure for NP0079134 (Lamellarin alpha)