NP-MRD: Showing NP-Card for didehydrotuberostemonine A (NP0331795)

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Record Information

Version

1.0

Created at

2023-09-08 08:03:10 UTC

Updated at

2024-04-19 09:51:51 UTC

NP-MRD ID

NP0331795

Secondary Accession Numbers

None

Natural Product Identification

Common Name

didehydrotuberostemonine A

Description

Didehydrotuberostemonine A belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively. Based on a literature review very few articles have been published on Didehydrotuberostemonine A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 09082308032D          

 30 34  0  0  1  0            999 V2000
    3.5468    0.4401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7220    0.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2251    1.0837    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4658    1.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4452    0.8147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7383    0.3893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234    1.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0165    0.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6065    1.3297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846    2.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7099    2.7963    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1130    2.8543    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5318    2.8677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    3.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110    4.0967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9396    4.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880    3.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4775    3.9933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5373    2.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4178    1.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -0.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6839   -0.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0180   -0.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532   -0.4355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7792   -1.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5063   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4601   -0.0102    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5611   -0.8290    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2492   -0.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  6  0  0  0
  5  3  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  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  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 14 18  2  0  0  0  0
 10 19  2  0  0  0  0
  7 19  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  8 24  1  0  0  0  0
 25 24  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 28 25  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
  2 30  1  0  0  0  0
M  END


  Mrv2104 09082308032D          

 30 34  0  0  1  0            999 V2000
    3.5468    0.4401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7220    0.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2251    1.0837    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4658    1.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4452    0.8147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7383    0.3893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234    1.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0165    0.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6065    1.3297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846    2.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7099    2.7963    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1130    2.8543    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5318    2.8677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    3.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0110    4.0967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9396    4.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3880    3.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4775    3.9933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5373    2.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4178    1.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4799   -0.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6839   -0.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0180   -0.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532   -0.4355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7792   -1.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5063   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4601   -0.0102    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5611   -0.8290    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2492   -0.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  6  0  0  0
  5  3  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  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  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 14 18  2  0  0  0  0
 10 19  2  0  0  0  0
  7 19  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  8 24  1  0  0  0  0
 25 24  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 28 25  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
  2 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331795

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(C[C@H](C)C(=O)O1)C1=CC2=C3N1CCCC=C3[C@@H](CC)[C@]1([H])OC(=O)[C@@H](C)[C@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H27NO4/c1-4-13-14-7-5-6-8-23-16(17-9-11(2)21(24)26-17)10-15(19(14)23)18-12(3)22(25)27-20(13)18/h7,10-13,17-18,20H,4-6,8-9H2,1-3H3/t11-,12-,13+,17-,18+,20-/m0/s1

> <INCHI_KEY>
NXXRQRYLLDGROE-NRIDCKAISA-N

> <FORMULA>
C22H27NO4

> <MOLECULAR_WEIGHT>
369.461

> <EXACT_MASS>
369.194008353

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.714666016659585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10R,11S,14S,15R)-10-ethyl-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadeca-1(16),2,8-trien-13-one

> <JCHEM_LOGP>
3.6279518919999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.789614322454037

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
101.48949999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11S,14S,15R)-10-ethyl-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadeca-1(16),2,8-trien-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-23         0                                  
HETATM    1  O   UNK     0       6.621   0.821   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.081   0.794   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.153   2.023   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.603   3.496   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.698   1.521   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       1.378   0.727   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       1.350   2.267   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.031   1.473   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.132   2.482   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.531   3.900   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.325   5.220   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       0.211   5.328   0.000  0.00  0.00           H+0
HETATM   13  O   UNK     0      -2.859   5.353   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.207   6.853   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.887   7.647   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.754   9.181   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.724   6.638   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.625   7.454   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.003   3.767   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.646   2.202   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.372   0.844   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.762  -0.570   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.277  -0.975   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.034  -0.066   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.406  -0.813   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.454  -2.352   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.812  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.726  -0.019   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       2.914  -1.547   0.000  0.00  0.00           H+0
HETATM   30  O   UNK     0       4.198  -0.468   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   28                                             
CONECT    6    5                                                            
CONECT    7    5    8   19                                                  
CONECT    8    7    9   24                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   12   13   17                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11                                                       
CONECT   18   14                                                            
CONECT   19   10    7                                                       
CONECT   20    9   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    8   25                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25    5   29   30                                             
CONECT   29   28                                                            
CONECT   30   28    2                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇NO₄

Average Mass

369.4610 Da

Monoisotopic Mass

369.19401 Da

IUPAC Name

(10R,11S,14S,15R)-10-ethyl-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadeca-1(16),2,8-trien-13-one

Traditional Name

(10R,11S,14S,15R)-10-ethyl-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadeca-1(16),2,8-trien-13-one

CAS Registry Number

Not Available

SMILES

[H][C@]1(C[C@H](C)C(=O)O1)C1=CC2=C3N1CCCC=C3[C@@H](CC)[C@]1([H])OC(=O)[C@@H](C)[C@]21[H]

InChI Identifier

InChI=1S/C22H27NO4/c1-4-13-14-7-5-6-8-23-16(17-9-11(2)21(24)26-17)10-15(19(14)23)18-12(3)22(25)27-20(13)18/h7,10-13,17-18,20H,4-6,8-9H2,1-3H3/t11-,12-,13+,17-,18+,20-/m0/s1

InChI Key

NXXRQRYLLDGROE-NRIDCKAISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-09-08	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-09-08	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Stemona alkaloids

Sub Class

Stemoamide-type alkaloids

Direct Parent

Stichoneurine-type alkaloids

Alternative Parents

Substituents

Stichoneurine-type alkaloid
Pyrroloazepine
Indole or derivatives
Azepine
Dicarboxylic acid or derivatives
Gamma butyrolactone
Substituted pyrrole
Heteroaromatic compound
Tetrahydrofuran
Pyrrole
Carboxylic acid ester
Lactone
Azacycle
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Organic oxide
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	3.63	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.49 m³·mol⁻¹	ChemAxon
Polarizability	40.71 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

28286897

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102421988

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for didehydrotuberostemonine A (NP0331795)

MOL for NP0331795 (didehydrotuberostemonine A)

3D MOL for NP0331795 (didehydrotuberostemonine A)

3D SDF for NP0331795 (didehydrotuberostemonine A)

3D-SDF for NP0331795 (didehydrotuberostemonine A)

PDB for NP0331795 (didehydrotuberostemonine A)

3D PDB for NP0331795 (didehydrotuberostemonine A)

SMILES for NP0331795 (didehydrotuberostemonine A)

INCHI for NP0331795 (didehydrotuberostemonine A)

Structure for NP0331795 (didehydrotuberostemonine A)

3D Structure for NP0331795 (didehydrotuberostemonine A)