NP-MRD: Showing NP-Card for 23-methylergosta-7,22-diene-3β,5α,6β-triol (NP0332551)

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Record Information

Version

1.0

Created at

2024-02-22 12:18:31 UTC

Updated at

2024-04-19 10:11:05 UTC

NP-MRD ID

NP0332551

Secondary Accession Numbers

None

Natural Product Identification

Common Name

23-methylergosta-7,22-diene-3β,5α,6β-triol

Description

(22E)-23-Methyl-5alpha-ergosta-7,22-diene-3beta,5,6beta-triol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. It was first documented in 2011 (PMID: 21985077). Based on a literature review a significant number of articles have been published on (22E)-23-Methyl-5alpha-ergosta-7,22-diene-3beta,5,6beta-triol (PMID: 36057450) (PMID: 36057449) (PMID: 36057448) (PMID: 36057447) (PMID: 36057446) (PMID: 36057445).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032220542D          

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M  END


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 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 10  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  9 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  1  0  0  0
  2 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332551

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](C)C(\C)=C\[C@@H](C)[C@H]1CC[C@H]2C3=C[C@@H](O)[C@@]4(O)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O3/c1-17(2)20(5)18(3)14-19(4)23-8-9-24-22-15-26(31)29(32)16-21(30)10-13-28(29,7)25(22)11-12-27(23,24)6/h14-15,17,19-21,23-26,30-32H,8-13,16H2,1-7H3/b18-14+/t19-,20-,21+,23-,24+,25+,26-,27-,28-,29+/m1/s1

> <INCHI_KEY>
CZRJCGNHTAJYEV-JFEPHHBUSA-N

> <FORMULA>
C29H48O3

> <MOLECULAR_WEIGHT>
444.7

> <EXACT_MASS>
444.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.63591035271348

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,7R,8R,11R,14R,15R)-2,15-dimethyl-14-[(2R,3E,5R)-4,5,6-trimethylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,7,8-triol

> <JCHEM_LOGP>
5.130257824

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.481621457260868

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.126600421564376

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7283051033051207

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
133.2557

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7R,8R,11R,14R,15R)-2,15-dimethyl-14-[(2R,3E,5R)-4,5,6-trimethylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,7,8-triol

> <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       2.892  -8.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.417  -8.505   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.861  -0.987   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.998  -9.932   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.523 -10.142   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.053 -11.147   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.633 -12.574   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.527 -10.937   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   21                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   14   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   10   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    9    6   27                                             
CONECT   27   26                                                            
CONECT   28    2   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(22E)-23-Methyl-5a-ergosta-7,22-diene-3b,5,6b-triol	Generator
(22E)-23-Methyl-5α-ergosta-7,22-diene-3β,5,6β-triol	Generator

Chemical Formula

C₂₉H₄₈O₃

Average Mass

444.7000 Da

Monoisotopic Mass

444.36035 Da

IUPAC Name

(1S,2R,5S,7R,8R,11R,14R,15R)-2,15-dimethyl-14-[(2R,3E,5R)-4,5,6-trimethylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,7,8-triol

Traditional Name

(1S,2R,5S,7R,8R,11R,14R,15R)-2,15-dimethyl-14-[(2R,3E,5R)-4,5,6-trimethylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,7,8-triol

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](C)C(\C)=C\[C@@H](C)[C@H]1CC[C@H]2C3=C[C@@H](O)[C@@]4(O)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C29H48O3/c1-17(2)20(5)18(3)14-19(4)23-8-9-24-22-15-26(31)29(32)16-21(30)10-13-28(29,7)25(22)11-12-27(23,24)6/h14-15,17,19-21,23-26,30-32H,8-13,16H2,1-7H3/b18-14+/t19-,20-,21+,23-,24+,25+,26-,27-,28-,29+/m1/s1

InChI Key

CZRJCGNHTAJYEV-JFEPHHBUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	yijing0212@163.com	南方医科大学	Jing Yi	2024-02-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	yijing0212@163.com	南方医科大学	Jing Yi	2024-02-22	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, C2D6OS, experimental)	yijing0212@163.com	南方医科大学	Jing Yi	2024-02-22	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	yijing0212@163.com	南方医科大学	Jing Yi	2024-02-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802 MHz, C2D6OS, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.918653341 MHz, C2D6OS, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
3-hydroxy-delta-7-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
6-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
Delta-7-steroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Polyol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

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	5.13	ChemAxon
pKa (Strongest Acidic)	13.13	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	133.26 m³·mol⁻¹	ChemAxon
Polarizability	54.64 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

8798542

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10623178

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Micalizzi E, Vaudano AE, Ballerini A, Talami F, Giovannini G, Turchi G, Cioclu MC, Giunta L, Meletti S: Ictal Apnea: a prospective monocentric study in patients with epilepsy. Eur J Neurol. 2022 Sep 3. doi: 10.1111/ene.15547. [PubMed:36057450 ]
Jiang S, Guo P, Heo HY, Zhang Y, Wu J, Jin Y, Laterra J, Eberhart CG, Lim M, Blakeley JO: Radiomics analysis of amide proton transfer-weighted and structural MR images for treatment response assessment in malignant gliomas. NMR Biomed. 2022 Sep 3:e4824. doi: 10.1002/nbm.4824. [PubMed:36057449 ]
Agarwal K, Saikia P, Podder I: Metabolic syndrome and Dyslipidemia in xanthelasma palpebrarum and associated risk-factors- a case-control study. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15353. [PubMed:36057448 ]
Lebel V, Argiropoulos N, Robins S, Charbonneau L, Feeley N: Family-centred care and breastfeeding self-efficacy determined how ready mothers were for their infants to be discharged from a neonatal intensive care unit. Acta Paediatr. 2022 Sep 3. doi: 10.1111/apa.16538. [PubMed:36057447 ]
Park JI, Kim SJ, Kim YJ, Lee SJ: Protective role of Caesalpinia sappan extract and its main component brazilin against blue light-induced damage in human fibroblasts. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15354. [PubMed:36057446 ]
Laccourreye O: Dog days.... Eur Ann Otorhinolaryngol Head Neck Dis. 2022 Aug;139(4):171-172. doi: 10.1016/j.anorl.2022.08.003. [PubMed:36057445 ]
Prissel MA, Solomon M: RE: Fellowships in Podiatric Medicine. J Foot Ankle Surg. 2022 Sep-Oct;61(5):1137. doi: 10.1053/j.jfas.2021.03.013. [PubMed:36057444 ]
Ishikawa T, Inoue S, Kawaguchi M: A pediatric case of severe systemic pneumatosis during airway pressure release ventilation. Med Intensiva (Engl Ed). 2022 Sep;46(9):544-545. doi: 10.1016/j.medine.2020.03.007. [PubMed:36057443 ]
Isidoro Duarte T, Amaral M, Pires C, Casimiro J, Germano N: Hemodynamic monitoring for liver transplantation: Agreement between invasive and non-invasive devices? Med Intensiva (Engl Ed). 2022 Sep;46(9):527-529. doi: 10.1016/j.medine.2021.06.006. [PubMed:36057442 ]
Nazir M, Sultan M, Riaz N, Hafeez M, Hussain H, Ahmed I, Schulz B, Draeger S, Jabbar A, Krohn K, Ashraf M, Saleem M: Depsitinuside: a new depside galactoside from an endophytic fungus isolated from Viburnum tinus. J Asian Nat Prod Res. 2011 Oct;13(11):1056-60. doi: 10.1080/10286020.2011.606811. Epub 2011 Oct 10. [PubMed:21985077 ]

Showing NP-Card for 23-methylergosta-7,22-diene-3β,5α,6β-triol (NP0332551)

MOL for NP0332551 (23-methylergosta-7,22-diene-3β,5α,6β-triol)

3D MOL for NP0332551 (23-methylergosta-7,22-diene-3β,5α,6β-triol)

3D SDF for NP0332551 (23-methylergosta-7,22-diene-3β,5α,6β-triol)

3D-SDF for NP0332551 (23-methylergosta-7,22-diene-3β,5α,6β-triol)

PDB for NP0332551 (23-methylergosta-7,22-diene-3β,5α,6β-triol)

3D PDB for NP0332551 (23-methylergosta-7,22-diene-3β,5α,6β-triol)

SMILES for NP0332551 (23-methylergosta-7,22-diene-3β,5α,6β-triol)

INCHI for NP0332551 (23-methylergosta-7,22-diene-3β,5α,6β-triol)

Structure for NP0332551 (23-methylergosta-7,22-diene-3β,5α,6β-triol)

3D Structure for NP0332551 (23-methylergosta-7,22-diene-3β,5α,6β-triol)