NP-MRD: Showing NP-Card for (1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one (NP0171492)

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Record Information

Version

2.0

Created at

2022-09-03 08:02:07 UTC

Updated at

2022-09-03 08:02:07 UTC

NP-MRD ID

NP0171492

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one

Description

(1S,2R,5R,7S,10S,14R,15S)-14-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-8-one, also known as 2-deoxycastasterone or (3alpha,5alpha,22R,23R,24S)-3,22,23-trihydroxyergostan-6-one, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. (1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one is found in Camellia sinensis, Catharanthus roseus, Cryptomeria japonica, Distylium racemosum, Lilium maculatum, Marchantia polymorpha, Picea sitchensis, Pinus thunbergii, Robinia pseudoacacia, Secale cereale, Senna obtusifolia, Triticum aestivum, Typha latifolia and Zea mays. Based on a literature review very few articles have been published on (1S,2R,5R,7S,10S,14R,15S)-14-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-8-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032210022D          

 32 35  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309032210022D          

 32 35  0  0  1  0            999 V2000
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   13.0984   -3.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2914   -3.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0365   -2.4242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4234   -2.9762    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
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 10  1  1  0  0  0
 12 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  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 18  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 15 31  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0171492

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)[C@H]1CCC2[C@@H]3CC(=O)[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O4/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/h15-23,25-26,29,31-32H,7-14H2,1-6H3/t16-,17-,18+,19-,20+,21?,22-,23+,25+,26+,27+,28+/m0/s1

> <INCHI_KEY>
SBSXXCCMIWEPEE-KIAMPEDASA-N

> <FORMULA>
C28H48O4

> <MOLECULAR_WEIGHT>
448.688

> <EXACT_MASS>
448.355260026

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
53.776215032327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5R,7S,10S,14R,15S)-14-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-8-one

> <ALOGPS_LOGP>
3.73

> <JCHEM_LOGP>
4.576522391

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.861077440618985

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.644363838141157

> <JCHEM_PKA_STRONGEST_BASIC>
-2.696313461282922

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
127.85939999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5R,7S,10S,14R,15S)-14-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      13.059  -3.899   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.393  -4.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.393  -6.209   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.726  -3.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.726  -2.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.060  -4.669   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      17.060  -6.209   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      18.394  -3.899   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      18.394  -2.359   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      19.728  -4.669   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.728  -6.209   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.061  -3.899   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.222  -2.367   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.729  -2.047   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.499  -3.381   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.005  -3.701   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.035  -2.556   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.542  -2.877   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      28.572  -1.732   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      28.018  -4.341   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      29.524  -4.661   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.000  -6.126   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      31.506  -6.446   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      28.969  -7.271   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.463  -6.950   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      26.987  -5.486   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      25.957  -6.630   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      25.481  -5.166   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      24.450  -6.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      22.944  -5.990   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      22.468  -4.525   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      21.324  -5.556   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   31                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   20   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   16   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   15   12   32                                             
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
2-Deoxycastasterone	Kegg
(3alpha,5alpha,22R,23R,24S)-3,22,23-Trihydroxyergostan-6-one	Kegg
(3a,5a,22R,23R,24S)-3,22,23-Trihydroxyergostan-6-one	Generator
(3Α,5α,22R,23R,24S)-3,22,23-trihydroxyergostan-6-one	Generator

Chemical Formula

C₂₈H₄₈O₄

Average Mass

448.6880 Da

Monoisotopic Mass

448.35526 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)[C@H]1CCC2[C@@H]3CC(=O)[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C28H48O4/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/h15-23,25-26,29,31-32H,7-14H2,1-6H3/t16-,17-,18+,19-,20+,21?,22-,23+,25+,26+,27+,28+/m0/s1

InChI Key

SBSXXCCMIWEPEE-KIAMPEDASA-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
Camellia sinensis	LOTUS Database	35616633
Catharanthus roseus	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Distylium racemosum	LOTUS Database	35616633
Lilium maculatum	LOTUS Database	35616633
Marchantia polymorpha	LOTUS Database	35616633
Picea sitchensis	LOTUS Database	35616633
Pinus thunbergii	LOTUS Database	35616633
Robinia pseudoacacia	LOTUS Database	35616633
Secale cereale	LOTUS Database	35616633
Senna obtusifolia	LOTUS Database	35616633
Triticum aestivum	LOTUS Database	35616633
Typha latifolia	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl 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

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
Ergostane-skeleton
Ecdysteroid
Trihydroxy bile acid, alcohol, or derivatives
23-hydroxysteroid
22-hydroxysteroid
3-hydroxysteroid
Hydroxysteroid
Oxosteroid
6-oxosteroid
3-alpha-hydroxysteroid
Cyclic alcohol
Ketone
Secondary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

ergostane (C15793 )
Ergosterols and C24-methyl derivatives (C15793 )

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	3.73	ALOGPS
logS	-4.4	ALOGPS

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000185

Chemspider ID

30792028

KEGG Compound ID

C15793

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724585

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one (NP0171492)

MOL for NP0171492 ((1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D MOL for NP0171492 ((1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D SDF for NP0171492 ((1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D-SDF for NP0171492 ((1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

PDB for NP0171492 ((1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D PDB for NP0171492 ((1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

SMILES for NP0171492 ((1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

INCHI for NP0171492 ((1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

Structure for NP0171492 ((1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D Structure for NP0171492 ((1r,3bs,5as,7r,9ar,9bs,11as)-1-[(2s,3r,4r,5s)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)