NP-MRD: Showing NP-Card for 8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde (NP0220823)

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Record Information

Version

2.0

Created at

2022-09-05 22:14:31 UTC

Updated at

2022-09-05 22:14:31 UTC

NP-MRD ID

NP0220823

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde

Description

10-Hydroxy-2,3,6-trimethyl-1-[3-methyl-1-(methylamino)butyl]-9,13-dioxo-2,4a,7,8,9,10,11,12,13,13a-decahydro-1H-benzo[11]annulene-13a-carbaldehyde belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). 8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde is found in Mariannaea elegans. 10-Hydroxy-2,3,6-trimethyl-1-[3-methyl-1-(methylamino)butyl]-9,13-dioxo-2,4a,7,8,9,10,11,12,13,13a-decahydro-1H-benzo[11]annulene-13a-carbaldehyde is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181500052D          

 30 31  0  0  0  0            999 V2000
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    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
   -0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8007   -2.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6077   -3.0545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432   -3.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0202   -2.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4681   -1.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1343   -0.3971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9139   -1.8076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
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  8 27  1  0  0  0  0
 13 27  1  0  0  0  0
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 11 30  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004181500052D          

 30 31  0  0  0  0            999 V2000
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0220823

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC(CC(C)C)C1C(C)C(C)=CC2C=C(C)CCC(=O)C(O)CCC(=O)C12C=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H39NO4/c1-15(2)11-20(26-6)24-18(5)17(4)13-19-12-16(3)7-8-21(28)22(29)9-10-23(30)25(19,24)14-27/h12-15,18-20,22,24,26,29H,7-11H2,1-6H3

> <INCHI_KEY>
LEEMIFWRBUAKCM-UHFFFAOYSA-N

> <FORMULA>
C25H39NO4

> <MOLECULAR_WEIGHT>
417.59

> <EXACT_MASS>
417.28790874

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
47.390461126072196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-hydroxy-2,3,6-trimethyl-1-[3-methyl-1-(methylamino)butyl]-9,13-dioxo-2,4a,7,8,9,10,11,12,13,13a-decahydro-1H-benzo[11]annulene-13a-carbaldehyde

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
3.4798377083333327

> <ALOGPS_LOGS>
-4.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.669132804373852

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.392576475106136

> <JCHEM_PKA_STRONGEST_BASIC>
10.42576225117345

> <JCHEM_POLAR_SURFACE_AREA>
83.47

> <JCHEM_REFRACTIVITY>
121.47229999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.001  -3.850   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.495  -5.382   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.001  -5.702   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.627  -7.109   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.771  -4.368   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.741  -3.224   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.984  -0.741   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334   0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.573  -3.374   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    3    9   27                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   27                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    8   13   28                                             
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   11                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₉NO₄

Average Mass

417.5900 Da

Monoisotopic Mass

417.28791 Da

IUPAC Name

10-hydroxy-2,3,6-trimethyl-1-[3-methyl-1-(methylamino)butyl]-9,13-dioxo-2,4a,7,8,9,10,11,12,13,13a-decahydro-1H-benzo[11]annulene-13a-carbaldehyde

Traditional Name

8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde

CAS Registry Number

Not Available

SMILES

CNC(CC(C)C)C1C(C)C(C)=CC2C=C(C)CCC(=O)C(O)CCC(=O)C12C=O

InChI Identifier

InChI=1S/C25H39NO4/c1-15(2)11-20(26-6)24-18(5)17(4)13-19-12-16(3)7-8-21(28)22(29)9-10-23(30)25(19,24)14-27/h12-15,18-20,22,24,26,29H,7-11H2,1-6H3

InChI Key

LEEMIFWRBUAKCM-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
Mariannaea elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Secondary alcohols

Alternative Parents

Substituents

Cyclic ketone
Secondary alcohol
Ketone
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Amine
Aldehyde
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	2.51	ALOGPS
logP	3.48	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.39	ChemAxon
pKa (Strongest Basic)	10.43	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.47 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.47 m³·mol⁻¹	ChemAxon
Polarizability	47.39 Å³	ChemAxon
Number of Rings	2	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

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 8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde (NP0220823)

MOL for NP0220823 (8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde)

3D MOL for NP0220823 (8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde)

3D SDF for NP0220823 (8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde)

3D-SDF for NP0220823 (8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde)

PDB for NP0220823 (8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde)

3D PDB for NP0220823 (8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde)

SMILES for NP0220823 (8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde)

INCHI for NP0220823 (8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde)

Structure for NP0220823 (8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde)

3D Structure for NP0220823 (8-hydroxy-2,3,12-trimethyl-4-[3-methyl-1-(methylamino)butyl]-5,9-dioxo-3,4,6,7,8,10,11,13a-octahydrobenzo[11]annulene-4a-carbaldehyde)