NP-MRD: Showing NP-Card for 1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione (NP0204627)

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Record Information

Version

2.0

Created at

2022-09-05 00:20:30 UTC

Updated at

2022-09-05 00:20:30 UTC

NP-MRD ID

NP0204627

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione

Description

3-Dehydroteasterone belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. 3-Dehydroteasterone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-dehydroteasterone has been detected, but not quantified in, several different foods, such as calabash, lemon verbena, docks, olives, and watercress. 1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione is found in Lilium longiflorum. This could make 3-dehydroteasterone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061312442D          

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M  END

     RDKit          3D

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  Mrv0541 05061312442D          

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 27  5  1  0  0  0  0
 27 12  1  0  0  0  0
 27 20  1  0  0  0  0
 27 21  1  0  0  0  0
 28  6  1  0  0  0  0
 28 11  1  0  0  0  0
 28 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29 18  2  0  0  0  0
 30 24  2  0  0  0  0
 31 25  1  0  0  0  0
 32 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204627

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)C(O)C(O)C(C)C1CCC2C3CC(=O)C4CC(=O)CCC4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O4/c1-15(2)16(3)25(31)26(32)17(4)20-7-8-21-19-14-24(30)23-13-18(29)9-11-28(23,6)22(19)10-12-27(20,21)5/h15-17,19-23,25-26,31-32H,7-14H2,1-6H3

> <INCHI_KEY>
SVBMASFUJDIDJC-UHFFFAOYSA-N

> <FORMULA>
C28H46O4

> <MOLECULAR_WEIGHT>
446.6624

> <EXACT_MASS>
446.33960996

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
53.42710506238984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,8-dione

> <ALOGPS_LOGP>
3.83

> <JCHEM_LOGP>
4.784023192666669

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.079935513869657

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.655641230567355

> <JCHEM_PKA_STRONGEST_BASIC>
-3.254723053919168

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
126.83129999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.27e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       3.153 -10.179   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.487 -12.489   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.820  -8.639   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.821 -12.489   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.418 -11.836   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.051 -12.910   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.316  -8.647   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.823  -8.327   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.063 -13.551   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.544 -12.590   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.557 -13.231   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.038 -12.270   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.618 -10.942   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.129  -8.837   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.487 -10.949   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.820 -10.179   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.821 -10.949   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.094 -12.406   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.099  -9.981   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.155 -10.179   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.593  -9.661   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.575 -11.446   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.112 -10.621   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.636  -9.157   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.154 -10.949   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.488 -10.179   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.562 -10.805   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.081 -11.766   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      21.600 -12.726   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      18.666  -8.012   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       7.154 -12.489   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.488  -8.639   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   17                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7    8   20                                                       
CONECT    8    7   21                                                       
CONECT    9   11   18                                                       
CONECT   10   12   22                                                       
CONECT   11    9   28                                                       
CONECT   12   10   27                                                       
CONECT   13   18   23                                                       
CONECT   14   19   24                                                       
CONECT   15    1    2   16                                                  
CONECT   16    3   15   25                                                  
CONECT   17    4   20   26                                                  
CONECT   18    9   13   29                                                  
CONECT   19   14   21   22                                                  
CONECT   20    7   17   27                                                  
CONECT   21    8   19   27                                                  
CONECT   22   10   19   28                                                  
CONECT   23   13   24   28                                                  
CONECT   24   14   23   30                                                  
CONECT   25   16   26   31                                                  
CONECT   26   17   25   32                                                  
CONECT   27    5   12   20   21                                             
CONECT   28    6   11   22   23                                             
CONECT   29   18                                                            
CONECT   30   24                                                            
CONECT   31   25                                                            
CONECT   32   26                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
22,23-Dihydroxy-24-methylcholestane-3,6-dione	HMDB
22,23-Dihydroxyergostane-3,6-dione	HMDB

Chemical Formula

C₂₈H₄₆O₄

Average Mass

446.6624 Da

Monoisotopic Mass

446.33961 Da

IUPAC Name

14-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,8-dione

Traditional Name

14-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,8-dione

CAS Registry Number

Not Available

SMILES

CC(C)C(C)C(O)C(O)C(C)C1CCC2C3CC(=O)C4CC(=O)CCC4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H46O4/c1-15(2)16(3)25(31)26(32)17(4)20-7-8-21-19-14-24(30)23-13-18(29)9-11-28(23,6)22(19)10-12-27(20,21)5/h15-17,19-23,25-26,31-32H,7-14H2,1-6H3

InChI Key

SVBMASFUJDIDJC-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
Lilium longiflorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Not Available

Substituents

Not Available

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	3.83	ALOGPS
logP	4.78	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.66	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.83 m³·mol⁻¹	ChemAxon
Polarizability	53.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041527

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021504

KNApSAcK ID

C00007262

Chemspider ID

21234468

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14353978

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione (NP0204627)

MOL for NP0204627 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione)

3D MOL for NP0204627 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione)

3D SDF for NP0204627 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione)

3D-SDF for NP0204627 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione)

PDB for NP0204627 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione)

3D PDB for NP0204627 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione)

SMILES for NP0204627 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione)

INCHI for NP0204627 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione)

Structure for NP0204627 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione)

3D Structure for NP0204627 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione)