NP-MRD: Showing NP-Card for Girinimbin (NP0067424)

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Record Information

Version

2.0

Created at

2022-04-28 12:17:10 UTC

Updated at

2022-04-28 12:17:10 UTC

NP-MRD ID

NP0067424

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Girinimbin

Description

Girinimbine, also known as NSC 94932, belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. Girinimbine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Girinimbine has been detected, but not quantified in, herbs and spices. Girinimbin is found in Clausena anisata, Clausena excavata, Clausena harmandiana, Clausena vestita, Murraya euchrestifolia, Murraya koenigii , Murraya microphylla and Murraya siamensis Craib. Girinimbin was first documented in 1994 (PMID: 8053931). This could make girinimbine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -0.9060   -2.8801    1.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691   -1.6549    0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0989   -1.4887    0.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6776   -0.3591    0.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9018    0.6307   -0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925    1.6152   -0.9036 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908    1.3095   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1914    1.9378   -0.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3506    1.3131   -0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3396    0.0800    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1410   -0.5301    0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9740    0.0688   -0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894    0.4891   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0310   -0.6588    0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066   -0.7870    0.0865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3038    0.1347   -0.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2009    0.6190    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1332   -0.5934   -1.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6479    1.3357   -1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3438    1.5081   -1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167   -3.7194    0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9863   -2.6663    1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4579   -3.1246    2.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6990   -2.2772    1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961    2.4871   -1.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1829    2.8942   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167    1.7818   -0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684   -0.4053    0.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1210   -1.4985    0.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6142    1.4295    1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1433    1.0518    0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3649   -0.1865    1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6412   -0.4950   -2.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2276   -1.6700   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1515   -0.1661   -1.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2782    2.0790   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9286    2.3958   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  2  0
 20 13  1  0
 13  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  4  1  0
  4  3  2  0
  3  2  1  0
 13 14  1  0
  4  5  1  0
 12  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
  3 24  1  0
M  END


  Mrv0541 05061305062D          

 20 23  0  0  0  0            999 V2000
    2.6777    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6585   -0.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191    1.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4665    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5058    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7333    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8117   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5144   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6908   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0487    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0392    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9671    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2434    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0784   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7907    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5961    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3198    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3068   -0.3254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7724    1.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 11  1  1  0  0  0  0
 11 10  1  0  0  0  0
 12  6  2  0  0  0  0
 13  8  1  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15  7  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 16 14  1  0  0  0  0
 17 11  2  0  0  0  0
 17 13  1  0  0  0  0
 18  2  1  0  0  0  0
 18  3  1  0  0  0  0
 18  9  1  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 20 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067424

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2OC(C)(C)C=CC2=C2NC3=CC=CC=C3C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO/c1-11-10-14-12-6-4-5-7-15(12)19-16(14)13-8-9-18(2,3)20-17(11)13/h4-10,19H,1-3H3

> <INCHI_KEY>
GAEQWKVGMHUUKO-UHFFFAOYSA-N

> <FORMULA>
C18H17NO

> <MOLECULAR_WEIGHT>
263.3337

> <EXACT_MASS>
263.131014171

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
30.801638238253393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,3,5-trimethyl-3H,11H-pyrano[3,2-a]carbazole

> <ALOGPS_LOGP>
5.03

> <JCHEM_LOGP>
4.504930480666667

> <ALOGPS_LOGS>
-5.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.849801921735594

> <JCHEM_PKA_STRONGEST_BASIC>
-4.919571545196121

> <JCHEM_POLAR_SURFACE_AREA>
25.02

> <JCHEM_REFRACTIVITY>
82.90680000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.19e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,3,5-trimethyl-11H-pyrano[3,2-a]carbazole

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.998   4.720   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.229  -0.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.342   1.914   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.071   1.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.144   0.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.702   2.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.849  -0.768   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.694  -0.606   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.156  -0.517   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.228   3.257   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.691   3.345   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.407   1.476   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.539   0.682   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.921   1.881   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.480  -0.063   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.076   0.594   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.846   2.057   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.464   0.858   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       8.039  -0.607   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       3.308   2.146   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   18                                                            
CONECT    3   18                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   15                                                       
CONECT    8    9   13                                                       
CONECT    9    8   18                                                       
CONECT   10   11   14                                                       
CONECT   11    1   10   17                                                  
CONECT   12    6   14   15                                                  
CONECT   13    8   16   17                                                  
CONECT   14   10   12   16                                                  
CONECT   15    7   12   19                                                  
CONECT   16   13   14   19                                                  
CONECT   17   11   13   20                                                  
CONECT   18    2    3    9   20                                             
CONECT   19   15   16                                                       
CONECT   20   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
3,11-Dihydro-3,3,5-trimethyl-pyrano(3,2-a)carbazole	HMDB
3,11-Dihydro-3,3,5-trimethylpyrano[3,2-a]carbazole, 9ci	HMDB
Girinimbin	HMDB
NSC 94932	HMDB
Girinimbine	ChEMBL, MeSH

Chemical Formula

C₁₈H₁₇NO

Average Mass

263.3337 Da

Monoisotopic Mass

263.13101 Da

IUPAC Name

3,3,5-trimethyl-3H,11H-pyrano[3,2-a]carbazole

Traditional Name

3,3,5-trimethyl-11H-pyrano[3,2-a]carbazole

CAS Registry Number

Not Available

SMILES

CC1=C2OC(C)(C)C=CC2=C2NC3=CC=CC=C3C2=C1

InChI Identifier

InChI=1S/C18H17NO/c1-11-10-14-12-6-4-5-7-15(12)19-16(14)13-8-9-18(2,3)20-17(11)13/h4-10,19H,1-3H3

InChI Key

GAEQWKVGMHUUKO-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
Clausena anisata	LOTUS Database	35616633
Clausena excavata	LOTUS Database	35616633
Clausena harmandiana	LOTUS Database	35616633
Clausena vestita	LOTUS Database	35616633
Murraya euchrestifolia	LOTUS Database	35616633
Murraya koenigii	Plant	KNApSAcK
Murraya microphylla	Plant	KNApSAcK
Murraya siamensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
2,2-dimethyl-1-benzopyran
Benzopyran
1-benzopyran
Indole
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Pyrrole
Ether
Oxacycle
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbazoles (CHEBI:69926 )

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	5.03	ALOGPS
logP	4.5	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	14.85	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	25.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	82.91 m³·mol⁻¹	ChemAxon
Polarizability	30.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030241

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002064

KNApSAcK ID

C00025171

Chemspider ID

87534

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Girinimbine

METLIN ID

Not Available

PubChem Compound

96943

PDB ID

Not Available

ChEBI ID

1001644

Good Scents ID

Not Available

References

General References

Ko FN, Lee YS, Wu TS, Teng CM: Inhibition of cyclooxygenase activity and increase in platelet cyclic AMP by girinimbine, isolated from Murraya euchrestifolia. Biochem Pharmacol. 1994 Jul 19;48(2):353-60. doi: 10.1016/0006-2952(94)90107-4. [PubMed:8053931 ]

Showing NP-Card for Girinimbin (NP0067424)

MOL for NP0067424 (Girinimbin)

3D MOL for NP0067424 (Girinimbin)

3D SDF for NP0067424 (Girinimbin)

3D-SDF for NP0067424 (Girinimbin)

PDB for NP0067424 (Girinimbin)

3D PDB for NP0067424 (Girinimbin)

SMILES for NP0067424 (Girinimbin)

INCHI for NP0067424 (Girinimbin)

Structure for NP0067424 (Girinimbin)

3D Structure for NP0067424 (Girinimbin)