NP-MRD: Showing NP-Card for 15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one (NP0147586)

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Record Information

Version

2.0

Created at

2022-09-02 03:13:12 UTC

Updated at

2022-09-02 03:13:12 UTC

NP-MRD ID

NP0147586

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one

Description

2-Deoxybrassinolide belongs to the class of organic compounds known as brassinolides and derivatives. These are cholestane based steroid lactones containing benzo[c]indeno[5,4-e]oxepin-3-one. 2-Deoxybrassinolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-deoxybrassinolide has been detected, but not quantified in, a few different foods, such as common pea, green vegetables, and pulses. 15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one is found in Arabidopsis thaliana. This could make 2-deoxybrassinolide a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241211242D          

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M  END

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M  END


  Mrv0541 02241211242D          

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  1  9  1  0  0  0  0
  1 13  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
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7 23  1  0  0  0  0
  8  9  1  0  0  0  0
  9 25  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 22  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  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
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25 26  1  0  0  0  0
 25 30  1  0  0  0  0
 26 27  1  0  0  0  0
 26 31  1  0  0  0  0
 27 28  1  0  0  0  0
 27 32  1  0  0  0  0
 28 29  1  0  0  0  0
 28 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147586

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)CCC4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O5/c1-15(2)16(3)24(30)25(31)17(4)20-7-8-21-19-14-33-26(32)23-13-18(29)9-11-28(23,6)22(19)10-12-27(20,21)5/h15-25,29-31H,7-14H2,1-6H3

> <INCHI_KEY>
LLFIMDUWAVPJEJ-UHFFFAOYSA-N

> <FORMULA>
C28H48O5

> <MOLECULAR_WEIGHT>
464.6777

> <EXACT_MASS>
464.350174646

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
53.88086765890961

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
4.204970492

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.859298646706513

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.644245350899563

> <JCHEM_PKA_STRONGEST_BASIC>
-2.698325938373002

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
129.04509999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.921   2.152   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.164   1.244   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.684  -0.219   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.144  -0.219   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.891  -1.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.205  -2.738   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.855  -4.134   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.411   4.460   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.921   3.693   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.395  -1.033   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.867   0.433   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.835   1.575   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.328   1.244   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.644   2.758   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.722  -0.476   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.591  -2.019   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.926  -1.249   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.266  -2.019   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -7.583  -4.339   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -6.266  -3.582   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.911  -4.368   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.591  -3.549   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.351  -4.496   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.677  -6.001   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.254   4.460   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.586   3.693   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.918   4.460   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.251   3.693   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.583   4.460   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.254   6.001   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.586   2.152   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.918   6.001   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.251   2.152   0.000  0.00  0.00           C+0
CONECT    1    2    9   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6   23                                                       
CONECT    8    9                                                            
CONECT    9    1    8   25                                                  
CONECT   10    5   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13    1    4   12   14                                             
CONECT   14   13                                                            
CONECT   15   16                                                            
CONECT   16   10   15   17   22                                             
CONECT   17   16   18                                                       
CONECT   18   17   20                                                       
CONECT   19   20                                                            
CONECT   20   18   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   16   21   23                                                  
CONECT   23    7   22   24                                                  
CONECT   24   23                                                            
CONECT   25    9   26   30                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28                                                            
CONECT   30   25                                                            
CONECT   31   26                                                            
CONECT   32   27                                                            
CONECT   33   28                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
3,22,23-Trihydroxy-24-methyl-b-homo-7-oxacholestan-6-one	HMDB

Chemical Formula

C₂₈H₄₈O₅

Average Mass

464.6777 Da

Monoisotopic Mass

464.35017 Da

IUPAC Name

15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one

Traditional Name

15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one

CAS Registry Number

Not Available

SMILES

CC(C)C(C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)CCC4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H48O5/c1-15(2)16(3)24(30)25(31)17(4)20-7-8-21-19-14-33-26(32)23-13-18(29)9-11-28(23,6)22(19)10-12-27(20,21)5/h15-25,29-31H,7-14H2,1-6H3

InChI Key

LLFIMDUWAVPJEJ-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
Arabidopsis thaliana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as brassinolides and derivatives. These are cholestane based steroid lactones containing benzo[c]indeno[5,4-e]oxepin-3-one.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Brassinolides and derivatives

Alternative Parents

Substituents

Brassinolide-skeleton
Caprolactone
Oxepane
Cyclic alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

a brassinosteroids (CPD-12498 )

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	3.44	ALOGPS
logP	4.2	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	13.64	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	129.05 m³·mol⁻¹	ChemAxon
Polarizability	53.88 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

HMDB0041135

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021019

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

14153905

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one (NP0147586)

MOL for NP0147586 (15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one)

3D MOL for NP0147586 (15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one)

3D SDF for NP0147586 (15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one)

3D-SDF for NP0147586 (15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one)

PDB for NP0147586 (15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one)

3D PDB for NP0147586 (15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one)

SMILES for NP0147586 (15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one)

INCHI for NP0147586 (15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one)

Structure for NP0147586 (15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one)

3D Structure for NP0147586 (15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one)