NP-MRD: Showing NP-Card for (1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol (NP0330692)

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Record Information

Version

1.0

Created at

2022-09-12 16:17:03 UTC

Updated at

2022-09-12 16:17:03 UTC

NP-MRD ID

NP0330692

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol

Description

(1S,2S,5R,7S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-ol 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. (1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol is found in Amphilectus fucorum. It was first documented in 2022 (PMID: 36130844). Based on a literature review a significant number of articles have been published on (1S,2S,5R,7S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-ol (PMID: 36130843) (PMID: 36130842) (PMID: 36130841) (PMID: 36130840) (PMID: 36130836) (PMID: 36130839).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122218172D          

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M  END

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  Mrv1652309122218172D          

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 23 25  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 13 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0330692

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H50O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18-26,29H,7-17H2,1-6H3/t19-,20-,21+,22-,23+,24-,25+,26+,27+,28-/m1/s1

> <INCHI_KEY>
ARYTXMNEANMLMU-UOYMAXTLSA-N

> <FORMULA>
C28H50O

> <MOLECULAR_WEIGHT>
402.707

> <EXACT_MASS>
402.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
52.82711606507928

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
7.805487608333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.296396321121705

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569562491413656

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
124.31509999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-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  C   UNK     0      18.394  -3.899   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.728  -4.669   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.728  -6.209   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.061  -3.899   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.222  -2.367   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.729  -2.047   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.499  -3.381   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.005  -3.701   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.035  -2.556   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.542  -2.877   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.018  -4.341   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.524  -4.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.000  -6.126   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      31.506  -6.446   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      28.969  -7.271   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.463  -6.950   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.987  -5.486   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.957  -6.630   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.481  -5.166   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.450  -6.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.944  -5.990   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.468  -4.525   0.000  0.00  0.00           C+0
HETATM   29  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                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   14   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   13   10   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₅₀O

Average Mass

402.7070 Da

Monoisotopic Mass

402.38617 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H50O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18-26,29H,7-17H2,1-6H3/t19-,20-,21+,22-,23+,24-,25+,26+,27+,28-/m1/s1

InChI Key

ARYTXMNEANMLMU-UOYMAXTLSA-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
Amphilectus fucorum	LOTUS Database	35616633

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-alpha-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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

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

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

162919680

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cani I, Righini M, Cenni P, Foschi M: Teaching NeuroImage: Partially Reversible Widespread Leukoencephalopathy Associated With Atypical Hemolytic Uremic Syndrome. Neurology. 2022 Sep 21. pii: WNL.0000000000201378. doi: 10.1212/WNL.0000000000201378. [PubMed:36130844 ]
Sasaki R, Morimoto S, Ozawa F, Okano H, Yoshida M, Ishiura H, Tsuji S, Kuzuhara S, Kokubo Y: APOE Alleles With Tau and Abeta Pathology In Patients With Amyotrophic Lateral Sclerosis and Parkinsonism-Dementia Complex in the Kii Peninsula. Neurology. 2022 Sep 21. pii: WNL.0000000000201156. doi: 10.1212/WNL.0000000000201156. [PubMed:36130843 ]
Zhang Z, Wang M, Gill D, Liu X: Genetically Predicted Smoking and Alcohol Consumption and Functional Outcome After Ischemic Stroke. Neurology. 2022 Sep 21. pii: WNL.0000000000201291. doi: 10.1212/WNL.0000000000201291. [PubMed:36130842 ]
Khamis S, Mitakidou MR, Champion M, Goyal S, Jones RL, Siddiqui A, Sabanathan S, Hedderly T, Lin JP, Jungbluth H, Papandreou A: Clinical Reasoning: A Teenage Girl With Progressive Hyperkinetic Movements, Seizures, and Encephalopathy. Neurology. 2022 Sep 21. pii: WNL.0000000000201385. doi: 10.1212/WNL.0000000000201385. [PubMed:36130841 ]
Rosenberg A, Ohlund-Wistbacka U, Hall A, Bonnard A, Hagman G, Ryden M, Thunborg C, Wiggenraad F, Sandebring-Matton A, Solomon A, Kivipelto M: beta-Amyloid, Tau, Neurodegeneration Classification and Eligibility for Anti-amyloid Treatment in a Memory Clinic Population. Neurology. 2022 Sep 21. pii: WNL.0000000000201043. doi: 10.1212/WNL.0000000000201043. [PubMed:36130840 ]
Yu H, Cai G, Wu J, Li Q: Clinical Phenotypic Variability and Significance of Pneumolabyrinth After Tympanum-Penetrating Injury. Ear Nose Throat J. 2022 Sep 21:1455613221128132. doi: 10.1177/01455613221128132. [PubMed:36130836 ]
Silverman A, Beres S: Child Neurology: Horner Syndrome in an Otherwise Well-Appearing Infant. Neurology. 2022 Sep 21. pii: WNL.0000000000201377. doi: 10.1212/WNL.0000000000201377. [PubMed:36130839 ]
Harada Y, Wang SH, Juel VC: Clinical Reasoning: A 36-Year-Old Man With Asymmetric Muscle Weakness. Neurology. 2022 Sep 21. pii: WNL.0000000000201379. doi: 10.1212/WNL.0000000000201379. [PubMed:36130838 ]
Guest O, Memon AA, Chukweubuka A, Zaheer M, Siddiqi N: Robotic low anterior resection for locally advanced rectal cancer - A video vignette. Colorectal Dis. 2022 Sep 21. doi: 10.1111/codi.16345. [PubMed:36130837 ]
Pellicori P, Kalra PR, Clark AL, Friday JM, Cleland JGF: Chronic kidney disease (CKD) and CKD-ism in heart failure - what a mess! Eur J Heart Fail. 2022 Sep 21. doi: 10.1002/ejhf.2696. [PubMed:36130835 ]
LOTUS database [Link]

Showing NP-Card for (1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol (NP0330692)

MOL for NP0330692 ((1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D MOL for NP0330692 ((1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D SDF for NP0330692 ((1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D-SDF for NP0330692 ((1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

PDB for NP0330692 ((1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D PDB for NP0330692 ((1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

SMILES for NP0330692 ((1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

INCHI for NP0330692 ((1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

Structure for NP0330692 ((1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)

3D Structure for NP0330692 ((1r,3as,3br,5as,7r,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol)