NP-MRD: Showing NP-Card for n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid (NP0248002)

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Record Information

Version

2.0

Created at

2022-09-07 10:04:09 UTC

Updated at

2022-09-07 10:04:09 UTC

NP-MRD ID

NP0248002

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid

Description

N-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-tetradecahydrophenanthren-2-ylidene]ethanimidic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid is found in Erythrophleum africanum. N-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-tetradecahydrophenanthren-2-ylidene]ethanimidic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201505292D          

 32 34  0  0  0  0            999 V2000
   -2.8057    9.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5236    8.3435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7111    8.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808    8.8322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    7.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 31 32  1  0  0  0  0
  5 32  1  0  0  0  0
 11 32  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004201505292D          

 32 34  0  0  0  0            999 V2000
   -2.8057    9.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0248002

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(C)C(O)CCC2(C)C3CCC(=CC(=O)NCCN(C)C)C(C)C3C(=O)CC12

> <INCHI_IDENTIFIER>
InChI=1S/C25H40N2O5/c1-15-16(13-21(30)26-11-12-27(4)5)7-8-17-22(15)18(28)14-19-24(17,2)10-9-20(29)25(19,3)23(31)32-6/h13,15,17,19-20,22,29H,7-12,14H2,1-6H3,(H,26,30)

> <INCHI_KEY>
TZEBUKDWHLEPOL-UHFFFAOYSA-N

> <FORMULA>
C25H40N2O5

> <MOLECULAR_WEIGHT>
448.604

> <EXACT_MASS>
448.293722396

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.90767997978807

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 7-({[2-(dimethylamino)ethyl]carbamoyl}methylidene)-2-hydroxy-1,4a,8-trimethyl-9-oxo-tetradecahydrophenanthrene-1-carboxylate

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
1.8248583429999983

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.88993093986835

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.436871688073918

> <JCHEM_PKA_STRONGEST_BASIC>
7.808385046591987

> <JCHEM_POLAR_SURFACE_AREA>
95.94

> <JCHEM_REFRACTIVITY>
123.69619999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 7-({[2-(dimethylamino)ethyl]carbamoyl}methylidene)-2-hydroxy-1,4a,8-trimethyl-9-oxo-decahydrophenanthrene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -5.237  17.022   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.711  15.575   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.194  15.307   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.204  16.487   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.184  13.593   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  14.630   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  16.170   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.000  13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000  12.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.000  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000   7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.000   3.080   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       1.334   5.390   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.335   9.240   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667  12.320   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    7   32                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   32                                             
CONECT   12   11                                                            
CONECT   13   11   14   28                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   16   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   13   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    5   11                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
N-[2-(Dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-tetradecahydrophenanthren-2-ylidene]ethanimidate	Generator

Chemical Formula

C₂₅H₄₀N₂O₅

Average Mass

448.6040 Da

Monoisotopic Mass

448.29372 Da

IUPAC Name

methyl 7-({[2-(dimethylamino)ethyl]carbamoyl}methylidene)-2-hydroxy-1,4a,8-trimethyl-9-oxo-tetradecahydrophenanthrene-1-carboxylate

Traditional Name

methyl 7-({[2-(dimethylamino)ethyl]carbamoyl}methylidene)-2-hydroxy-1,4a,8-trimethyl-9-oxo-decahydrophenanthrene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(C)C(O)CCC2(C)C3CCC(=CC(=O)NCCN(C)C)C(C)C3C(=O)CC12

InChI Identifier

InChI=1S/C25H40N2O5/c1-15-16(13-21(30)26-11-12-27(4)5)7-8-17-22(15)18(28)14-19-24(17,2)10-9-20(29)25(19,3)23(31)32-6/h13,15,17,19-20,22,29H,7-12,14H2,1-6H3,(H,26,30)

InChI Key

TZEBUKDWHLEPOL-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, 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
Erythrophleum africanum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Cassane diterpenoid
Diterpenoid
Steroid
Hydrophenanthrene
Phenanthrene
Beta-hydroxy acid
Hydroxy acid
Cyclic alcohol
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ketone
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Organic oxide
Organopnictogen compound
Amine
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.2	ALOGPS
logP	1.82	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.44	ChemAxon
pKa (Strongest Basic)	7.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.94 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.7 m³·mol⁻¹	ChemAxon
Polarizability	50.91 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid (NP0248002)

MOL for NP0248002 (n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid)

3D MOL for NP0248002 (n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid)

3D SDF for NP0248002 (n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid)

3D-SDF for NP0248002 (n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid)

PDB for NP0248002 (n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid)

3D PDB for NP0248002 (n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid)

SMILES for NP0248002 (n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid)

INCHI for NP0248002 (n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid)

Structure for NP0248002 (n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid)

3D Structure for NP0248002 (n-[2-(dimethylamino)ethyl]-2-[7-hydroxy-8-(methoxycarbonyl)-1,4b,8-trimethyl-10-oxo-decahydrophenanthren-2-ylidene]ethanimidic acid)