NP-MRD: Showing NP-Card for (9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione (NP0154894)

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Record Information

Version

2.0

Created at

2022-09-02 11:52:37 UTC

Updated at

2022-09-02 11:52:37 UTC

NP-MRD ID

NP0154894

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione

Description

Cyathisterone 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. (9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione is found in Calvatia cyathiformis. (9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione was first documented in 2017 (PMID: 28509846). Based on a literature review a small amount of articles have been published on cyathisterone (PMID: 29194412) (PMID: 28278634).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022213522D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022213522D          

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M  END
> <DATABASE_ID>
NP0154894

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](C)\C=C\[C@@H](C)C1CCC2C3=CC(=O)C4CC(=O)CC[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-16-26(30)25-15-20(29)11-13-28(25,6)24(21)12-14-27(22,23)5/h7-8,16-19,22-25H,9-15H2,1-6H3/b8-7+/t18-,19+,22?,23?,24?,25?,27+,28+/m0/s1

> <INCHI_KEY>
AGFWEYQAOQMEEO-OPJDNOSMSA-N

> <FORMULA>
C28H42O2

> <MOLECULAR_WEIGHT>
410.642

> <EXACT_MASS>
410.318480592

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
49.71926663032071

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,8-dione

> <ALOGPS_LOGP>
5.38

> <JCHEM_LOGP>
6.681981875000002

> <ALOGPS_LOGS>
-6.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.05361811050644

> <JCHEM_PKA_STRONGEST_BASIC>
-5.003602593257746

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
125.89759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.38e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-5,8-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.955  -2.378   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.571  -2.589   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.516  -1.373   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.595  -6.083   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   29                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   18   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   14   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   13   10   30                                             
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂O₂

Average Mass

410.6420 Da

Monoisotopic Mass

410.31848 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](C)\C=C\[C@@H](C)C1CCC2C3=CC(=O)C4CC(=O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C28H42O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-16-26(30)25-15-20(29)11-13-28(25,6)24(21)12-14-27(22,23)5/h7-8,16-19,22-25H,9-15H2,1-6H3/b8-7+/t18-,19+,22?,23?,24?,25?,27+,28+/m0/s1

InChI Key

AGFWEYQAOQMEEO-OPJDNOSMSA-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
Calvatia cyathiformis	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
Ecdysteroid
3-oxo-delta-7-steroid
3-oxosteroid
Oxosteroid
6-oxosteroid
Delta-7-steroid
Cyclohexenone
Ketone
Cyclic ketone
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
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	5.38	ALOGPS
logS	-6.1	ALOGPS

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

78445756

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584155

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Noinart J, Buttachon S, Dethoup T, Gales L, Pereira JA, Urbatzka R, Freitas S, Lee M, Silva AMS, Pinto MMM, Vasconcelos V, Kijjoa A: A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207. Mar Drugs. 2017 May 16;15(5). pii: md15050139. doi: 10.3390/md15050139. [PubMed:28509846 ]
Kumla D, Shine Aung T, Buttachon S, Dethoup T, Gales L, Pereira JA, Inacio A, Costa PM, Lee M, Sekeroglu N, Silva AMS, Pinto MMM, Kijjoa A: A New Dihydrochromone Dimer and Other Secondary Metabolites from Cultures of the Marine Sponge-Associated Fungi Neosartorya fennelliae KUFA 0811 and Neosartorya tsunodae KUFC 9213. Mar Drugs. 2017 Dec 1;15(12). pii: md15120375. doi: 10.3390/md15120375. [PubMed:29194412 ]
Arthan S, Tantapakul C, Kanokmedhakul K, Soytong K, Kanokmedhakul S: A new xanthone from the fungus Apiospora montagnei. Nat Prod Res. 2017 Aug;31(15):1766-1771. doi: 10.1080/14786419.2017.1290622. Epub 2017 Feb 28. [PubMed:28278634 ]
LOTUS database [Link]

Showing NP-Card for (9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione (NP0154894)

MOL for NP0154894 ((9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione)

3D MOL for NP0154894 ((9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione)

3D SDF for NP0154894 ((9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione)

3D-SDF for NP0154894 ((9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione)

PDB for NP0154894 ((9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione)

3D PDB for NP0154894 ((9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione)

SMILES for NP0154894 ((9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione)

INCHI for NP0154894 ((9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione)

Structure for NP0154894 ((9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione)

3D Structure for NP0154894 ((9ar,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5ah,6h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione)