NP-MRD: Showing NP-Card for (1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol (NP0328342)

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Record Information

Version

2.0

Created at

2022-09-12 11:43:57 UTC

Updated at

2022-09-12 11:43:57 UTC

NP-MRD ID

NP0328342

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol

Description

Tetrahydroalstonine belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor. (1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol is found in Alsophila podophylla, Alsophila spinulosa, Cannabis sativa, Costus tonkinensis, Cymbopogon martinii, Festuca argentina, Festuca hieronymi, Lessingianthus mollissimus, Panax quinquefolius, Salpa thompsoni and Setaria italica. (1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol was first documented in 1972 (PMID: 5050366). Tetrahydroalstonine is a very strong basic compound (based on its pKa) (PMID: 23285803) (PMID: 17340319) (PMID: 19403195).

Structure

MOL 3D MOL SDF PDB SMILES InChI

sitostanol
  Mrv1572001071617112D          

 30 33  0  0  1  0            999 V2000
    8.2924   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4674   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0549   -0.9035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2299   -0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8174   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.6180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5799   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799   -0.9035    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7594   -0.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    0.4022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4739    1.2091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8608    1.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0323    2.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170    2.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885    3.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7731    3.8850    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9446    4.6920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3862    3.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2147    2.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4301    2.2711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0432    1.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2585    1.4641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8716    0.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7001    0.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155   -0.1499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4675   -0.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4674   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2924   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0549   -2.3325    0.0000 C   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
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  1  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 82 85  0  0  0  0  0  0  0  0999 V2000
   -5.9547    0.2307   -2.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1388   -0.5196   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6332    0.0992    0.4065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1811    0.3725    0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5468    1.2931   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8478   -0.3234   -0.9601 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.3518    0.4276   -0.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5896   -1.2205    0.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1098   -1.3272    0.8945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3308   -0.1493    0.4222 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5245    0.9781    1.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8833   -0.5426    0.2929 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1312   -0.1755    1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6305   -0.3277    1.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1928    0.4402    0.1584 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6513    1.8429    0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1995   -0.5981    1.6490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7104   -0.4824    1.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8422   -2.0536    1.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6743   -0.4404    0.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2012   -1.4807   -1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1741   -0.5056   -3.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0227   -1.5028   -2.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7121    1.2784   -0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0078   -1.6331   -1.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  1  0
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 26  8  1  0
 26 11  1  0
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 30 80  1  0
 30 81  1  0
 30 82  1  0
M  END

sitostanol
  Mrv1572001071617112D          

 30 33  0  0  1  0            999 V2000
    8.2924   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4674   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0549   -0.9035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2299   -0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5799   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799   -0.9035    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7594   -0.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    0.4022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  1  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328342

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H52O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h19-27,30H,7-18H2,1-6H3/t20-,21-,22?,23+,24+,25-,26+,27+,28+,29-/m1/s1

> <INCHI_KEY>
LGJMUZUPVCAVPU-KZXGMYDKSA-N

> <FORMULA>
C29H52O

> <MOLECULAR_WEIGHT>
416.734

> <EXACT_MASS>
416.401816294

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
54.930718670985364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,10R,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol

> <ALOGPS_LOGP>
7.23

> <JCHEM_LOGP>
8.250056273333334

> <ALOGPS_LOGS>
-7.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.296396321121705

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569562491413656

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
128.91609999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.14e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
stigmastane-3-β-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: sitostanol                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      15.479  -0.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.939  -0.353   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.169  -1.687   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.629  -1.687   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.859  -3.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.319  -3.020   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.549  -4.354   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.549  -1.687   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.018  -1.526   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.697  -0.019   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.031   0.751   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.351   2.257   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.207   3.288   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.527   4.794   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.992   5.270   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.312   6.776   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.776   7.252   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.097   8.758   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.921   6.222   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.601   4.715   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.136   4.239   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.281   3.209   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.816   2.733   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.960   1.703   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.640   0.196   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.176  -0.280   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.206  -1.424   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.939  -3.020   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.479  -3.020   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.169  -4.354   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   26                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   12   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    8   11   27                                             
CONECT   27   26                                                            
CONECT   28    3   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methyl (20alpha)-16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylate	ChEBI
Methyl (20a)-16,17-didehydro-19a-methyl-18-oxayohimban-16-carboxylate	Generator
Methyl (20a)-16,17-didehydro-19a-methyl-18-oxayohimban-16-carboxylic acid	Generator
Methyl (20alpha)-16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylic acid	Generator
Methyl (20α)-16,17-didehydro-19α-methyl-18-oxayohimban-16-carboxylate	Generator
Methyl (20α)-16,17-didehydro-19α-methyl-18-oxayohimban-16-carboxylic acid	Generator
(3b)-Stigmastan-3-ol	HMDB
(3beta)-Stigmastan-3-ol	HMDB
(3beta,5alpha)-Stigmastan-3-ol	HMDB
24-alpha-Ethylcholestanol	HMDB
24a-Ethylcholestanol	HMDB
4a-Methyl-5a,14a-lumistan-3b-ol	HMDB
4a-Methylcampestanol	HMDB
5,6-dihydro-b-Sitosterol	HMDB
5,6-dihydro-beta-Sitosterol	HMDB
5a-Stigmastan-3b-ol	HMDB
5alpha-Stigmastan-3beta-ol	HMDB
b-Sitostanol	HMDB
beta-dihydro-Sitosterol	HMDB
beta-Sitostanol	HMDB, MeSH
dihydro-b-Sitosterol	HMDB
dihydro-beta-Sitosterol	HMDB
Dihydrositosterin	HMDB
Dihydrositosterol	HMDB, MeSH
Fucostanol	HMDB
Sitostanol	HMDB, MeSH
Spinastanol	HMDB
Stigmastan-3-ol	HMDB
Stigmastane-3-beta-ol	HMDB
24 alpha-Ethyl-5 alpha-cholestan-3 beta-ol	MeSH, HMDB
Stigmastanol, (3beta,5beta,24S)-isomer	MeSH, HMDB
24 alpha-Ethyl-5 beta-cholestan-3 alpha-ol	MeSH, HMDB
Stigmastanol	MeSH

Chemical Formula

C₂₉H₅₂O

Average Mass

416.7340 Da

Monoisotopic Mass

416.40182 Da

IUPAC Name

(1S,2S,5S,10R,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol

Traditional Name

stigmastane-3-β-ol

CAS Registry Number

Not Available

SMILES

CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

InChI Identifier

InChI=1S/C29H52O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h19-27,30H,7-18H2,1-6H3/t20-,21-,22?,23+,24+,25-,26+,27+,28+,29-/m1/s1

InChI Key

LGJMUZUPVCAVPU-KZXGMYDKSA-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
Alsophila podophylla	LOTUS Database	35616633
Alsophila spinulosa	LOTUS Database	35616633
Cannabis sativa	LOTUS Database	35616633
Costus tonkinensis	LOTUS Database	35616633
Cymbopogon martinii	LOTUS Database	35616633
Festuca argentina	LOTUS Database	35616633
Festuca hieronymi	LOTUS Database	35616633
Lessingianthus mollissimus	LOTUS Database	35616633
Panax quinquefolius	LOTUS Database	35616633
Salpa thompsoni	LOTUS Database	35616633
Setaria italica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Yohimbine alkaloids

Sub Class

Not Available

Direct Parent

Yohimbine alkaloids

Alternative Parents

Substituents

Ajmalicine-skeleton
18-oxayohimban
Corynanthean skeleton
Yohimbine alkaloid
Beta-carboline
Pyridoindole
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Benzenoid
Piperidine
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

yohimban alkaloid (CHEBI:9479 )
Indole alkaloids (C11682 )

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	7.23	ALOGPS
logP	8.25	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	128.92 m³·mol⁻¹	ChemAxon
Polarizability	54.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

C00025214

Chemspider ID

Not Available

KEGG Compound ID

C11682

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72340

PDB ID

Not Available

ChEBI ID

9479

Good Scents ID

Not Available

References

General References

Paniagua-Vega D, Cerda-Garcia-Rojas CM, Ponce-Noyola T, Ramos-Valdivia AC: A new monoterpenoid oxindole alkaloid from Hamelia patens micropropagated plantlets. Nat Prod Commun. 2012 Nov;7(11):1441-4. [PubMed:23285803 ]
Malik S: Tetrahydroalstonine from Fruits of Rhazya stricta. Planta Med. 1984 Jun;50(3):283. doi: 10.1055/s-2007-969707. [PubMed:17340319 ]
Pomahacova B, Dusek J, Duskova J, Yazaki K, Roytrakul S, Verpoorte R: Improved accumulation of ajmalicine and tetrahydroalstonine in Catharanthus cells expressing an ABC transporter. J Plant Physiol. 2009 Sep 1;166(13):1405-12. doi: 10.1016/j.jplph.2009.02.015. Epub 2009 Apr 29. [PubMed:19403195 ]
Kocialski AB, Marozzi FJ Jr, Malone MH: Effects of certain nonsteroid anti-inflammatory drugs, tolbutamide, and tetrahydroalstonine on blood glucose and carrageen in-induced pedal edema in rats. J Pharm Sci. 1972 Aug;61(8):1202-5. doi: 10.1002/jps.2600610805. [PubMed:5050366 ]
LOTUS database [Link]

Showing NP-Card for (1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol (NP0328342)

MOL for NP0328342 ((1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D MOL for NP0328342 ((1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D SDF for NP0328342 ((1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D-SDF for NP0328342 ((1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

PDB for NP0328342 ((1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D PDB for NP0328342 ((1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

SMILES for NP0328342 ((1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

INCHI for NP0328342 ((1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

Structure for NP0328342 ((1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D Structure for NP0328342 ((1r,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)