NP-MRD: Showing NP-Card for typhasterol (NP0162090)

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Record Information

Version

2.0

Created at

2022-09-02 20:25:33 UTC

Updated at

2022-09-02 20:25:33 UTC

NP-MRD ID

NP0162090

Secondary Accession Numbers

None

Natural Product Identification

Common Name

typhasterol

Description

Typhasterol 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. Thus, typhasterol is considered to be a sterol lipid molecule. typhasterol is found in Camellia sinensis, Catharanthus roseus, Cryptomeria japonica, Distylium racemosum, Erythronium japonicum, Lilium maculatum, Marchantia polymorpha, Picea sitchensis, Pinus thunbergii, Robinia pseudoacacia, Secale cereale, Senna tora, Triticum aestivum, Typha capensis and Zea mays. typhasterol was first documented in 2018 (PMID: 30302404). Typhasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 30594955) (PMID: 32146811) (PMID: 31031786) (PMID: 30241414).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306182020112D          

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M  END

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M  END


  Mrv1652306182020112D          

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10002.908510002.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337810001.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210000.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479210001.0567    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11  4  1  6  0  0  0
 19  3  2  0  0  0  0
 12 18  1  0  0  0  0
 18  8  1  6  0  0  0
  9 17  1  0  0  0  0
 17  2  1  1  0  0  0
 15 17  1  0  0  0  0
 15  6  1  6  0  0  0
 20 16  1  0  0  0  0
 16  5  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 37  1  6  0  0  0
 26 27  1  0  0  0  0
 26 28  1  6  0  0  0
 27 29  1  0  0  0  0
 27 30  1  1  0  0  0
 29 31  1  0  0  0  0
 29 32  1  1  0  0  0
 31 33  1  0  0  0  0
 31 34  1  1  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 16 22  1  0  0  0  0
 22  7  1  6  0  0  0
 13 21  1  0  0  0  0
 21  1  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0162090

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC(=O)[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C(C)C

> <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-SELDZKRUSA-N

> <FORMULA>
C28H48O4

> <MOLECULAR_WEIGHT>
448.688

> <EXACT_MASS>
448.355260026

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.04643122128781

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5R,7S,10S,11S,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>
14.861077440618988

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.644363838141157

> <JCHEM_PKA_STRONGEST_BASIC>
-2.696313461282922

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
127.8594

> <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,11S,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                                 18-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-JUN-20         0                                  
HETATM    1  C   UNK     0    8666.6228668.946   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.6338666.617   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8663.9638661.210   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8658.6368662.757   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8665.2928666.617   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8663.9638664.313   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8666.6228664.313   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0    8662.6338661.985   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8661.3028665.841   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8659.9688665.071   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8659.9688663.531   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.3028662.761   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.2948668.167   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.9608667.397   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.9608665.857   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.2948665.087   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.6308665.071   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8662.6308663.531   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.9648662.761   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8665.2978663.531   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.6278667.397   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.6278665.857   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.0928665.381   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.9978666.627   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.0928667.873   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8668.0928669.413   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8669.4288670.179   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8666.7608670.179   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8670.7608669.413   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8669.4288671.719   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0    8672.0968670.179   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0    8670.7608667.873   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0    8673.4328669.413   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8672.0968671.719   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8674.7648670.179   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8673.4328667.873   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0    8669.4288668.639   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   17                                                            
CONECT    3   19                                                            
CONECT    4   11                                                            
CONECT    5   16                                                            
CONECT    6   15                                                            
CONECT    7   22                                                            
CONECT    8   18                                                            
CONECT    9   10   17                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    4                                                  
CONECT   12   11   18                                                       
CONECT   13   14   21                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17    6                                             
CONECT   16   15   20    5   22                                             
CONECT   17   18    9    2   15                                             
CONECT   18   17   19   12    8                                             
CONECT   19   18   20    3                                                  
CONECT   20   19   16                                                       
CONECT   21   22   25   13    1                                             
CONECT   22   21   23   16    7                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   26   37   21   24                                             
CONECT   26   25   27   28                                                  
CONECT   27   26   29   30                                                  
CONECT   28   26                                                            
CONECT   29   27   31   32                                                  
CONECT   30   27                                                            
CONECT   31   29   33   34                                                  
CONECT   32   29                                                            
CONECT   33   31   35   36                                                  
CONECT   34   31                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   25                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
2-Deoxycastasterone	ChEBI
(3alpha,5alpha,22R,23R,24S)-3,22,23-Trihydroxyergostan-6-one	HMDB
(3α,5α,22R,23R,24S)-3,22,23-Trihydroxyergostan-6-one	HMDB
Typhasterol	HMDB

Chemical Formula

C₂₈H₄₈O₄

Average Mass

448.6880 Da

Monoisotopic Mass

448.35526 Da

IUPAC Name

(1S,2R,5R,7S,10S,11S,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

Traditional Name

(1S,2R,5R,7S,10S,11S,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

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC(=O)[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C(C)C

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-SELDZKRUSA-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
Erythronium japonicum	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 tora	LOTUS Database	35616633
Triticum aestivum	LOTUS Database	35616633
Typha capensis	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

23-hydroxy steroid (CHEBI:27173 )
3alpha-sterol (CHEBI:27173 )
6-oxo steroid (CHEBI:27173 )
22-hydroxy steroid (CHEBI:27173 )
brassinosteroid (CHEBI:27173 )
Ergosterols and C24-methyl derivatives (LMST01030130 )

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
logP	4.58	ChemAxon
logS	-4.4	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	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.86 m³·mol⁻¹	ChemAxon
Polarizability	54.05 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

HMDB0034423

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13475120

PDB ID

Not Available

ChEBI ID

27173

Good Scents ID

Not Available

References

General References

Bajguz A, Orczyk W, Golebiewska A, Chmur M, Piotrowska-Niczyporuk A: Occurrence of brassinosteroids and influence of 24-epibrassinolide with brassinazole on their content in the leaves and roots of Hordeum vulgare L. cv. Golden Promise. Planta. 2019 Jan;249(1):123-137. doi: 10.1007/s00425-018-03081-3. Epub 2018 Dec 29. [PubMed:30594955 ]
Roh J, Moon J, Youn JH, Seo C, Park YJ, Kim SK: Establishment of Biosynthetic Pathways To Generate Castasterone as the Biologically Active Brassinosteroid in Brachypodium distachyon. J Agric Food Chem. 2020 Apr 1;68(13):3912-3923. doi: 10.1021/acs.jafc.9b07963. Epub 2020 Mar 18. [PubMed:32146811 ]
Pavlovic I, Mlinaric S, Tarkowska D, Oklestkova J, Novak O, Lepedus H, Bok VV, Brkanac SR, Strnad M, Salopek-Sondi B: Early Brassica Crops Responses to Salinity Stress: A Comparative Analysis Between Chinese Cabbage, White Cabbage, and Kale. Front Plant Sci. 2019 Apr 11;10:450. doi: 10.3389/fpls.2019.00450. eCollection 2019. [PubMed:31031786 ]
Kumbhar ST, Patil SP, Une HD: Phytochemical analysis of Canna indica L. roots and rhizomes extract. Biochem Biophys Rep. 2018 Oct 5;16:50-55. doi: 10.1016/j.bbrep.2018.09.002. eCollection 2018 Dec. [PubMed:30302404 ]
Pavlovic I, Petrik I, Tarkowska D, Lepedus H, Vujcic Bok V, Radic Brkanac S, Novak O, Salopek-Sondi B: Correlations between Phytohormones and Drought Tolerance in Selected Brassica Crops: Chinese Cabbage, White Cabbage and Kale. Int J Mol Sci. 2018 Sep 21;19(10):2866. doi: 10.3390/ijms19102866. [PubMed:30241414 ]
LOTUS database [Link]

Showing NP-Card for typhasterol (NP0162090)

MOL for NP0162090 (typhasterol)

3D MOL for NP0162090 (typhasterol)

3D SDF for NP0162090 (typhasterol)

3D-SDF for NP0162090 (typhasterol)

PDB for NP0162090 (typhasterol)

3D PDB for NP0162090 (typhasterol)

SMILES for NP0162090 (typhasterol)

INCHI for NP0162090 (typhasterol)

Structure for NP0162090 (typhasterol)

3D Structure for NP0162090 (typhasterol)