NP-MRD: Showing NP-Card for (3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol (NP0149568)

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Record Information

Version

2.0

Created at

2022-09-02 05:28:45 UTC

Updated at

2022-09-02 05:28:45 UTC

NP-MRD ID

NP0149568

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol

Description

Mahanine, also known as isomahanine, 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. (3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol is found in Murraya euchrestifolia and Murraya koenigii. (3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol was first documented in 2020 (PMID: 33208840). Based on a literature review a small amount of articles have been published on Mahanine (PMID: 35661126) (PMID: 34643999) (PMID: 34175718) (PMID: 32851075).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207282D          

 26 29  0  0  1  0            999 V2000
    6.9578   -2.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2965   -2.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5387   -2.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3931   -1.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7319   -0.8530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8285   -0.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.4596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7678    1.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8092    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801   -0.3254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521   -0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145    1.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  1  0  0  0
  7  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 19 25  2  0  0  0  0
 16 25  1  0  0  0  0
 12 26  1  0  0  0  0
  7 26  1  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    4.9744   -1.3353   -1.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3288   -0.3931   -0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4333   -0.7822    0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7328    0.7467   -0.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6378    1.2238   -1.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4062    1.5765   -0.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7220    0.4965    0.2005 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5992   -0.1489    1.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1724   -0.4996   -0.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1063   -0.7870   -0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850   -0.0773   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6454    0.8807    0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5480    1.5812    1.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0886    2.6127    2.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8798    1.2708    1.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3227    0.3144    0.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4210   -0.3793   -0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0955   -1.2512   -1.0200 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4286   -1.1594   -0.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5252   -1.8098   -1.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7841   -1.4849   -0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9357   -2.0991   -1.3450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9264   -0.5023    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8190    0.1459    0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5588   -0.1823    0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6876    1.1593    0.9605 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0589   -1.9053   -1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8410   -2.0559   -1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8213   -0.8517   -2.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0738   -1.6128    0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3370   -1.1140   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7404    0.0508    0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0571    1.4110    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9673    2.1338   -1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4304    0.4490   -2.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984    2.4415    0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6589    1.9630   -1.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9273   -0.4559    2.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3268    0.5358    1.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0193   -1.1094    0.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8749   -1.0399   -1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4688   -1.5306   -1.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9668    3.2263    2.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2482    3.1980    2.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7141    2.0917    3.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6080    1.8089    2.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739   -1.9064   -1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4231   -2.5689   -2.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3217   -2.9530   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9236   -0.2381    0.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9089    0.9151    1.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  7  6  1  6
  7  8  1  0
  7 26  1  0
 26 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
 11 17  1  0
 17 16  2  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 16 25  1  0
 25 19  2  0
 19 18  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
  9  7  1  0
 18 17  1  0
 13 12  1  0
 24 25  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
 10 42  1  0
  9 41  1  0
 15 46  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 18 47  1  0
 20 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
M  END


  Mrv1652309022207282D          

 26 29  0  0  1  0            999 V2000
    6.9578   -2.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2965   -2.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5387   -2.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3931   -1.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7319   -0.8530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8285   -0.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.4596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7678    1.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8092    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801   -0.3254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521   -0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145    1.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  1  0  0  0
  7  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 19 25  2  0  0  0  0
 16 25  1  0  0  0  0
 12 26  1  0  0  0  0
  7 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149568

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC[C@@]1(C)OC2=C(C=C1)C1=C(C=C2C)C2=C(N1)C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C23H25NO2/c1-14(2)6-5-10-23(4)11-9-18-21-19(12-15(3)22(18)26-23)17-8-7-16(25)13-20(17)24-21/h6-9,11-13,24-25H,5,10H2,1-4H3/t23-/m1/s1

> <INCHI_KEY>
DWMBXHWBPZZCTN-HSZRJFAPSA-N

> <FORMULA>
C23H25NO2

> <MOLECULAR_WEIGHT>
347.458

> <EXACT_MASS>
347.188529049

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
41.34486938472054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-3H,11H-pyrano[3,2-a]carbazol-9-ol

> <ALOGPS_LOGP>
5.88

> <JCHEM_LOGP>
5.9390331640000005

> <ALOGPS_LOGS>
-6.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.502762017894955

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.771592594962259

> <JCHEM_PKA_STRONGEST_BASIC>
-4.920524559485762

> <JCHEM_POLAR_SURFACE_AREA>
45.25

> <JCHEM_REFRACTIVITY>
108.61330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.28e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11H-pyrano[3,2-a]carbazol-9-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      12.988  -4.963   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.754  -4.043   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.339  -4.651   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.934  -2.513   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.699  -1.592   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.880  -0.063   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.645   0.858   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.767   1.914   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.953  -0.517   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.415  -0.606   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.570   0.682   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.263   2.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.418   3.345   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.111   4.720   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.881   3.257   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.188   1.881   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.033   0.594   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.070  -0.607   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       2.629  -0.063   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.260  -0.768   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.035   0.064   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.404  -0.641   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.038   1.603   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.407   2.308   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.702   1.476   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.800   2.146   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   26                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   26                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   11   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   19   16                                                  
CONECT   26   12    7                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
Isomahanine	MeSH
Bisisomahanine	MeSH

Chemical Formula

C₂₃H₂₅NO₂

Average Mass

347.4580 Da

Monoisotopic Mass

347.18853 Da

IUPAC Name

(3R)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-3H,11H-pyrano[3,2-a]carbazol-9-ol

Traditional Name

(3R)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11H-pyrano[3,2-a]carbazol-9-ol

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@@]1(C)OC2=C(C=C1)C1=C(C=C2C)C2=C(N1)C=C(O)C=C2

InChI Identifier

InChI=1S/C23H25NO2/c1-14(2)6-5-10-23(4)11-9-18-21-19(12-15(3)22(18)26-23)17-8-7-16(25)13-20(17)24-21/h6-9,11-13,24-25H,5,10H2,1-4H3/t23-/m1/s1

InChI Key

DWMBXHWBPZZCTN-HSZRJFAPSA-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
Murraya euchrestifolia	LOTUS Database	35616633
Murraya koenigii	LOTUS Database	35616633

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
Benzopyran
1-benzopyran
Hydroxyindole
Indole
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Heteroaromatic compound
Pyrrole
Oxacycle
Azacycle
Ether
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
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	5.88	ALOGPS
logP	5.94	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	9.77	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	45.25 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	108.61 m³·mol⁻¹	ChemAxon
Polarizability	41.34 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024713

Chemspider ID

23350668

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

36689305

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Samanta SK, Choudhury P, Sarma PP, Gogoi B, Gogoi N, Devi R: Dietary phytochemicals/nutrients as promising protector of breast cancer development: a comprehensive analysis. Pharmacol Rep. 2022 Aug;74(4):583-601. doi: 10.1007/s43440-022-00373-0. Epub 2022 Jun 4. [PubMed:35661126 ]
Nandan S, Singh SK, Singh P, Bajpai V, Mishra AK, Joshi T, Mahar R, Shukla SK, Mishra DK, Kanojiya S: Quantitative Analysis of Bioactive Carbazole Alkaloids in Murraya koenigii (L.) from Six Different Climatic Zones of India Using UPLC/MS/MS and Their Principal Component Analysis. Chem Biodivers. 2021 Dec;18(12):e2100557. doi: 10.1002/cbdv.202100557. Epub 2021 Oct 27. [PubMed:34643999 ]
Ma XL, Zhu SS, Liu Y, Chen HW, Shi YT, Zeng KW, Tu PF, Jiang Y: Carbazole alkaloids with potential cytotoxic activities targeted on PCK2 protein from Murraya microphylla. Bioorg Chem. 2021 Sep;114:105113. doi: 10.1016/j.bioorg.2021.105113. Epub 2021 Jun 21. [PubMed:34175718 ]
Kandimalla R, Das M, Barge SR, Sarma PP, Koiri DJ, Devi A, Karki AK, Kumar A, Devi R, Pal BC, Talukdar NC, Samanta SK: Variation in biosynthesis of an effective anticancer secondary metabolite, mahanine in Murraya koenigii, conditional on soil physicochemistry and weather suitability. Sci Rep. 2020 Nov 18;10(1):20096. doi: 10.1038/s41598-020-77113-y. [PubMed:33208840 ]
Satyavarapu EM, Sinha PK, Mandal C: Preclinical Development of Mahanine-Enriched Fraction from Indian Spice Murraya koenigii for the Management of Cancer: Efficacy, Temperature/pH stability, Pharmacokinetics, Acute and Chronic Toxicity (14-180 Days) Studies. Biomed Res Int. 2020 Aug 10;2020:4638132. doi: 10.1155/2020/4638132. eCollection 2020. [PubMed:32851075 ]
LOTUS database [Link]

Showing NP-Card for (3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol (NP0149568)

MOL for NP0149568 ((3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol)

3D MOL for NP0149568 ((3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol)

3D SDF for NP0149568 ((3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol)

3D-SDF for NP0149568 ((3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol)

PDB for NP0149568 ((3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol)

3D PDB for NP0149568 ((3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol)

SMILES for NP0149568 ((3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol)

INCHI for NP0149568 ((3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol)

Structure for NP0149568 ((3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol)

3D Structure for NP0149568 ((3r)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11h-pyrano[3,2-a]carbazol-9-ol)