NP-MRD: Showing NP-Card for methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0240348)

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Record Information

Version

2.0

Created at

2022-09-07 00:09:22 UTC

Updated at

2022-09-07 00:09:22 UTC

NP-MRD ID

NP0240348

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate

Description

Brachycerine belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate is found in Psychotria brachyceras. methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate was first documented in 2007 (PMID: 17973310). Based on a literature review a small amount of articles have been published on Brachycerine (PMID: 26043882) (PMID: 25026705) (PMID: 24045228) (PMID: 22562190).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072202092D          

 39 44  0  0  1  0            999 V2000
    2.1382   -6.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1382   -5.4304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8526   -5.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -5.4304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8526   -4.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -3.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -2.9554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8526   -2.5429    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8526   -1.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -1.3054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5671   -0.4804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2816   -0.0679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2816    0.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9960    1.1696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9960   -0.4804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  8 21  1  0  0  0  0
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 22 36  1  0  0  0  0
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 36 38  1  0  0  0  0
 39 38  1  6  0  0  0
  5 39  1  0  0  0  0
 21 39  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309072202092D          

 39 44  0  0  1  0            999 V2000
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    0.0367   -0.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2916   -1.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3758   -2.2293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0433   -1.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8502   -1.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4023   -1.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1473   -0.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3403   -0.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883   -0.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -3.3679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0436   -3.3679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3535   -4.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1382   -3.7804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 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
 27 35  1  0  0  0  0
 30 35  1  0  0  0  0
 22 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 39 38  1  6  0  0  0
  5 39  1  0  0  0  0
 21 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240348

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2[C@H]1C[C@@H](O)[C@H]2[C@H]1CCCC2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C28H35NO10/c1-36-26(35)16-11-37-27(39-28-25(34)24(33)23(32)19(10-30)38-28)21-15(16)9-18(31)20(21)14-7-4-6-13-12-5-2-3-8-17(12)29-22(13)14/h2-3,5,8,11,14-15,18-21,23-25,27-34H,4,6-7,9-10H2,1H3/t14-,15+,18-,19-,20-,21-,23-,24+,25-,27+,28+/m1/s1

> <INCHI_KEY>
ZHFNEDGXVCJJIB-KIZNPYPLSA-N

> <FORMULA>
C28H35NO10

> <MOLECULAR_WEIGHT>
545.585

> <EXACT_MASS>
545.226096331

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.99947920252351

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,4aR,6R,7S,7aR)-6-hydroxy-7-[(1R)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_LOGP>
0.4633198080000001

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19079238336068

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.206122140060222

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8476061189631094

> <JCHEM_POLAR_SURFACE_AREA>
170.93

> <JCHEM_REFRACTIVITY>
135.60000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,4aR,6R,7S,7aR)-6-hydroxy-7-[(1R)-2,3,4,9-tetrahydro-1H-carbazol-1-yl]-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.991 -11.677   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.991 -10.137   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.325  -9.367   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.659 -10.137   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.325  -7.827   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.659  -7.057   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.659  -5.517   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.325  -4.747   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.325  -3.207   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.659  -2.437   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.659  -0.897   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.992  -0.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.992   1.413   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.326   2.183   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.326  -0.897   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.660  -0.127   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.326  -2.437   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.660  -3.207   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.992  -3.207   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.992  -4.747   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.991  -5.517   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.527  -5.041   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.051  -3.576   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.081  -2.432   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.605  -0.967   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.099  -0.647   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.068  -1.791   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.544  -3.256   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      -0.702  -4.161   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -1.947  -3.256   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.454  -3.576   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.484  -2.432   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.008  -0.967   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.502  -0.647   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.472  -1.791   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.621  -6.287   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.081  -6.287   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.527  -7.533   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.991  -7.057   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   39                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22   39                                                  
CONECT   22   21   23   36                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   35                                                  
CONECT   28   27   23   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   27   30                                                  
CONECT   36   22   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38    5   21                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₅NO₁₀

Average Mass

545.5850 Da

Monoisotopic Mass

545.22610 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2[C@H]1C[C@@H](O)[C@H]2[C@H]1CCCC2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C28H35NO10/c1-36-26(35)16-11-37-27(39-28-25(34)24(33)23(32)19(10-30)38-28)21-15(16)9-18(31)20(21)14-7-4-6-13-12-5-2-3-8-17(12)29-22(13)14/h2-3,5,8,11,14-15,18-21,23-25,27-34H,4,6-7,9-10H2,1H3/t14-,15+,18-,19-,20-,21-,23-,24+,25-,27+,28+/m1/s1

InChI Key

ZHFNEDGXVCJJIB-KIZNPYPLSA-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
Psychotria brachyceras	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Carbazole
Hexose monosaccharide
O-glycosyl compound
Iridoid-skeleton
Glycosyl compound
3-alkylindole
Monoterpenoid
Aromatic monoterpenoid
Indole or derivatives
Indole
Benzenoid
Oxane
Monosaccharide
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrole
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00027031

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

101110452

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Berger A, Kostyan MK, Klose SI, Gastegger M, Lorbeer E, Brecker L, Schinnerl J: Loganin and secologanin derived tryptamine-iridoid alkaloids from Palicourea crocea and Palicourea padifolia (Rubiaceae). Phytochemistry. 2015 Aug;116:162-169. doi: 10.1016/j.phytochem.2015.05.013. Epub 2015 Jun 1. [PubMed:26043882 ]
Porto DD, Matsuura HN, Vargas LR, Henriques AT, Fett-Neto AG: Shoot accumulation kinetics and effects on herbivores of the wound-induced antioxidant indole alkaloid brachycerine of Psychotria brachyceras. Nat Prod Commun. 2014 May;9(5):629-32. [PubMed:25026705 ]
do Nascimento NC, Menguer PK, Henriques AT, Fett-Neto AG: Accumulation of brachycerine, an antioxidant glucosidic indole alkaloid, is induced by abscisic acid, heavy metal, and osmotic stress in leaves of Psychotria brachyceras. Plant Physiol Biochem. 2013 Dec;73:33-40. doi: 10.1016/j.plaphy.2013.08.007. Epub 2013 Aug 31. [PubMed:24045228 ]
do Nascimento NC, Menguer PK, Sperotto RA, de Almeida MR, Fett-Neto AG: Early changes in gene expression induced by acute UV exposure in leaves of Psychotria brachyceras, a bioactive alkaloid accumulating plant. Mol Biotechnol. 2013 May;54(1):79-91. doi: 10.1007/s12033-012-9546-3. [PubMed:22562190 ]
do Nascimento NC, Fragoso V, Moura DJ, e Silva AC, Fett-Neto AG, Saffi J: Antioxidant and antimutagenic effects of the crude foliar extract and the alkaloid brachycerine of Psychotria brachyceras. Environ Mol Mutagen. 2007 Dec;48(9):728-34. doi: 10.1002/em.20349. [PubMed:17973310 ]
LOTUS database [Link]

Showing NP-Card for methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0240348)

MOL for NP0240348 (methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D MOL for NP0240348 (methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D SDF for NP0240348 (methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D-SDF for NP0240348 (methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

PDB for NP0240348 (methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D PDB for NP0240348 (methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

SMILES for NP0240348 (methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

INCHI for NP0240348 (methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

Structure for NP0240348 (methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D Structure for NP0240348 (methyl (1s,4ar,6r,7s,7ar)-6-hydroxy-7-[(1r)-2,3,4,9-tetrahydro-1h-carbazol-1-yl]-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)