NP-MRD: Showing NP-Card for 1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one (NP0206689)

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Record Information

Version

2.0

Created at

2022-09-05 03:01:38 UTC

Updated at

2022-09-05 03:01:38 UTC

NP-MRD ID

NP0206689

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one

Description

Dendrocrepin belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. 1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one is found in Dendrobium crepidatum. Dendrocrepin is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251507362D          

 38 43  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004251507362D          

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    1.9160   -2.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -1.4281    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
    0.1100   -3.7413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773   -4.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5472   -4.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9844   -5.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -5.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2274   -5.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -5.1406    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  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  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  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
  9 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206689

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2CCCN2C(CC(=O)CC2N3CCCC3CC(C)C2(O)C2=CC=CC=C2)C1(O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H44N2O3/c1-23-19-27-15-9-17-34(27)30(32(23,37)25-11-5-3-6-12-25)21-29(36)22-31-33(38,26-13-7-4-8-14-26)24(2)20-28-16-10-18-35(28)31/h3-8,11-14,23-24,27-28,30-31,37-38H,9-10,15-22H2,1-2H3

> <INCHI_KEY>
JPVGVKCBHJUCQQ-UHFFFAOYSA-N

> <FORMULA>
C33H44N2O3

> <MOLECULAR_WEIGHT>
516.726

> <EXACT_MASS>
516.335193285

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
59.17281091269801

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-bis(6-hydroxy-7-methyl-6-phenyl-octahydroindolizin-5-yl)propan-2-one

> <ALOGPS_LOGP>
4.85

> <JCHEM_LOGP>
4.991319834999999

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
13.609755773745256

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.012512701013236

> <JCHEM_PKA_STRONGEST_BASIC>
10.267049554609256

> <JCHEM_POLAR_SURFACE_AREA>
64.01

> <JCHEM_REFRACTIVITY>
151.16899999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1H-indolizin-5-yl)propan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.145  -4.360   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.519  -2.953   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.988  -3.114   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -2.667  -4.620   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.465   2.016   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.206  -0.054   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.483  -1.306   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.022  -1.252   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.839  -2.558   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.116  -3.918   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.577  -3.972   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.760  -2.666   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.205  -6.984   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.518  -8.236   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.021  -8.182   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.838  -9.488   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.115 -10.848   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.425 -10.902   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.241  -9.596   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8   10   31                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31    9    2   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₄N₂O₃

Average Mass

516.7260 Da

Monoisotopic Mass

516.33519 Da

IUPAC Name

1,3-bis(6-hydroxy-7-methyl-6-phenyl-octahydroindolizin-5-yl)propan-2-one

Traditional Name

1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1H-indolizin-5-yl)propan-2-one

CAS Registry Number

Not Available

SMILES

CC1CC2CCCN2C(CC(=O)CC2N3CCCC3CC(C)C2(O)C2=CC=CC=C2)C1(O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C33H44N2O3/c1-23-19-27-15-9-17-34(27)30(32(23,37)25-11-5-3-6-12-25)21-29(36)22-31-33(38,26-13-7-4-8-14-26)24(2)20-28-16-10-18-35(28)31/h3-8,11-14,23-24,27-28,30-31,37-38H,9-10,15-22H2,1-2H3

InChI Key

JPVGVKCBHJUCQQ-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
Dendrobium crepidatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
Phenylpiperidine
Indolizidine
Aralkylamine
Monocyclic benzene moiety
Benzenoid
N-alkylpyrrolidine
Piperidine
Beta-aminoketone
Tertiary alcohol
Pyrrolidine
1,2-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Ketone
Azacycle
Organoheterocyclic compound
Organic oxide
Organonitrogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Amine
Alcohol
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	4.85	ALOGPS
logP	4.99	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.01	ChemAxon
pKa (Strongest Basic)	10.27	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.01 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	151.17 m³·mol⁻¹	ChemAxon
Polarizability	59.17 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

615602

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one (NP0206689)

MOL for NP0206689 (1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one)

3D MOL for NP0206689 (1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one)

3D SDF for NP0206689 (1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one)

3D-SDF for NP0206689 (1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one)

PDB for NP0206689 (1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one)

3D PDB for NP0206689 (1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one)

SMILES for NP0206689 (1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one)

INCHI for NP0206689 (1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one)

Structure for NP0206689 (1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one)

3D Structure for NP0206689 (1,3-bis(6-hydroxy-7-methyl-6-phenyl-hexahydro-1h-indolizin-5-yl)propan-2-one)