NP-MRD: Showing NP-Card for (-)-Carbazomarine A (NP0076293)

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Record Information

Version

2.0

Created at

2022-04-28 21:26:41 UTC

Updated at

2022-04-28 21:26:41 UTC

NP-MRD ID

NP0076293

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Carbazomarine A

Description

Methyl 1-hydroxy-2-[(4S)-5-hydroxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-4-yl]-9H-carbazole-3-carboxylate belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. (-)-Carbazomarine A is found in Clausena excavata . Based on a literature review very few articles have been published on methyl 1-hydroxy-2-[(4S)-5-hydroxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-4-yl]-9H-carbazole-3-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223262D          

 41 46  0  0  1  0            999 V2000
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv1652304282223262D          

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    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1369    2.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482    2.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926    2.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9440    3.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3918    3.7878    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 17 23  1  0  0  0  0
  8 24  1  0  0  0  0
  4 25  1  0  0  0  0
  4 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
  1 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 28 36  1  0  0  0  0
 27 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
 40 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0076293

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC2=C(NC3=C2C=CC=C3)C(O)=C1[C@@H]1CC(C)(C)OC2=C1C(O)=C1C=CC(=O)OC1=C2C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C33H31NO7/c1-7-32(2,3)25-29-17(12-13-22(35)40-29)27(36)24-20(15-33(4,5)41-30(24)25)23-19(31(38)39-6)14-18-16-10-8-9-11-21(16)34-26(18)28(23)37/h7-14,20,34,36-37H,1,15H2,2-6H3/t20-/m0/s1

> <INCHI_KEY>
IIRBCWLZHUJBBE-FQEVSTJZSA-N

> <FORMULA>
C33H31NO7

> <MOLECULAR_WEIGHT>
553.611

> <EXACT_MASS>
553.210052342

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
59.567950764013496

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 1-hydroxy-2-[(7S)-9-hydroxy-5,5-dimethyl-2-(2-methylbut-3-en-2-yl)-13-oxo-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,11-tetraen-7-yl]-9H-carbazole-3-carboxylate

> <ALOGPS_LOGP>
6.01

> <JCHEM_LOGP>
6.427743426333333

> <ALOGPS_LOGS>
-5.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.135741152709404

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.763834232657375

> <JCHEM_PKA_STRONGEST_BASIC>
-4.896924179113025

> <JCHEM_POLAR_SURFACE_AREA>
118.08

> <JCHEM_REFRACTIVITY>
156.33530000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.97e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 1-hydroxy-2-[(7S)-9-hydroxy-5,5-dimethyl-2-(2-methylbut-3-en-2-yl)-13-oxo-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,11-tetraen-7-yl]-9H-carbazole-3-carboxylate

> <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       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.482  -2.934   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.001  -1.411   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.170  -3.935   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.749  -3.342   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.989  -6.896   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.520  -7.057   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       9.147  -5.650   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       9.147  -8.464   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.241  -9.710   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.710  -9.549   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.083  -8.142   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.641  -2.860   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.902   2.967   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.635   1.452   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.489  -2.211   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.410   2.270   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.989   4.088   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.703   5.106   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.400   4.959   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.629   5.780   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.598   7.071   0.000  0.00  0.00           C+0
CONECT    1    2    6   30                                                  
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   25   26                                             
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   24                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   10   18   23                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18    9                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17                                                       
CONECT   24    8                                                            
CONECT   25    4                                                            
CONECT   26    4                                                            
CONECT   27    2   28   37                                                  
CONECT   28   27   29   36                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29    1   31                                                  
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   28                                                       
CONECT   37   27   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37   41                                                       
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Value	Source
Methyl 1-hydroxy-2-[(4S)-5-hydroxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-4-yl]-9H-carbazole-3-carboxylic acid	Generator

Chemical Formula

C₃₃H₃₁NO₇

Average Mass

553.6110 Da

Monoisotopic Mass

553.21005 Da

IUPAC Name

methyl 1-hydroxy-2-[(7S)-9-hydroxy-5,5-dimethyl-2-(2-methylbut-3-en-2-yl)-13-oxo-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,11-tetraen-7-yl]-9H-carbazole-3-carboxylate

Traditional Name

methyl 1-hydroxy-2-[(7S)-9-hydroxy-5,5-dimethyl-2-(2-methylbut-3-en-2-yl)-13-oxo-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,11-tetraen-7-yl]-9H-carbazole-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC2=C(NC3=C2C=CC=C3)C(O)=C1[C@@H]1CC(C)(C)OC2=C1C(O)=C1C=CC(=O)OC1=C2C(C)(C)C=C

InChI Identifier

InChI=1S/C33H31NO7/c1-7-32(2,3)25-29-17(12-13-22(35)40-29)27(36)24-20(15-33(4,5)41-30(24)25)23-19(31(38)39-6)14-18-16-10-8-9-11-21(16)34-26(18)28(23)37/h7-14,20,34,36-37H,1,15H2,2-6H3/t20-/m0/s1

InChI Key

IIRBCWLZHUJBBE-FQEVSTJZSA-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
Clausena excavata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Linear pyranocoumarins

Alternative Parents

Substituents

Linear pyranocoumarin
Pyranochromene
Carbazole
2,2-dimethyl-1-benzopyran
Indolecarboxylic acid derivative
Indolecarboxylic acid
Hydroxyindole
1-benzopyran
Benzopyran
Chromane
Indole or derivatives
Indole
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Methyl ester
Pyrrole
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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	6.01	ALOGPS
logP	6.43	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	7.76	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	118.08 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	156.34 m³·mol⁻¹	ChemAxon
Polarizability	59.57 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	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

162821238

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Carbazomarine A (NP0076293)

MOL for NP0076293 ((-)-Carbazomarine A)

3D MOL for NP0076293 ((-)-Carbazomarine A)

3D SDF for NP0076293 ((-)-Carbazomarine A)

3D-SDF for NP0076293 ((-)-Carbazomarine A)

PDB for NP0076293 ((-)-Carbazomarine A)

3D PDB for NP0076293 ((-)-Carbazomarine A)

SMILES for NP0076293 ((-)-Carbazomarine A)

INCHI for NP0076293 ((-)-Carbazomarine A)

Structure for NP0076293 ((-)-Carbazomarine A)

3D Structure for NP0076293 ((-)-Carbazomarine A)