NP-MRD: Showing NP-Card for 1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol (NP0309150)

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Record Information

Version

2.0

Created at

2022-09-11 03:31:43 UTC

Updated at

2022-09-11 03:31:43 UTC

NP-MRD ID

NP0309150

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol

Description

14-(5,6-Dimethylhept-3-en-2-yl)-7-methoxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-ene-1,4-diol belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position. 1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol is found in Fusarium solani. Based on a literature review very few articles have been published on 14-(5,6-dimethylhept-3-en-2-yl)-7-methoxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-ene-1,4-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205312D          

 32 35  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309112205312D          

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  7  8  1  0  0  0  0
  8  9  1  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 11  1  4  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 10 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
  3 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309150

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC12CCC(O)CC1(C)C1(O)CCC3(C)C(CCC3C1=CC2)C(C)C=CC(C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O3/c1-19(2)20(3)8-9-21(4)23-10-11-24-25-13-15-28(32-7)14-12-22(30)18-27(28,6)29(25,31)17-16-26(23,24)5/h8-9,13,19-24,30-31H,10-12,14-18H2,1-7H3

> <INCHI_KEY>
OZENNGVRVKCACI-UHFFFAOYSA-N

> <FORMULA>
C29H48O3

> <MOLECULAR_WEIGHT>
444.7

> <EXACT_MASS>
444.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
53.82317391844271

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(5,6-dimethylhept-3-en-2-yl)-7-methoxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-1,4-diol

> <JCHEM_LOGP>
5.518420904000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.248723050307152

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.731969217950564

> <JCHEM_PKA_STRONGEST_BASIC>
-2.698943631214493

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
133.93509999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
14-(5,6-dimethylhept-3-en-2-yl)-7-methoxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-ene-1,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       4.288   1.357   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.804   1.086   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.883  -3.790   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.303  -5.217   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.408  -3.579   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.354  -4.795   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.879  -4.585   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.459  -3.158   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.824  -5.800   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.350  -5.590   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.244  -7.227   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.374  -3.259   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.423  -3.290   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.349  -3.895   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26   32                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   10    7   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    6   25   26                                             
CONECT   25   24                                                            
CONECT   26   24    3   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    3                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₈O₃

Average Mass

444.7000 Da

Monoisotopic Mass

444.36035 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC12CCC(O)CC1(C)C1(O)CCC3(C)C(CCC3C1=CC2)C(C)C=CC(C)C(C)C

InChI Identifier

InChI=1S/C29H48O3/c1-19(2)20(3)8-9-21(4)23-10-11-24-25-13-15-28(32-7)14-12-22(30)18-27(28,6)29(25,31)17-16-26(23,24)5/h8-9,13,19-24,30-31H,10-12,14-18H2,1-7H3

InChI Key

OZENNGVRVKCACI-UHFFFAOYSA-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
Fusarium solani	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergostane steroids

Alternative Parents

Substituents

Ergostane-skeleton
Hydroxysteroid
2-hydroxysteroid
Delta-7-steroid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ether
Dialkyl ether
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
logP	5.52	ChemAxon
pKa (Strongest Acidic)	13.73	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

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

162979639

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol (NP0309150)

MOL for NP0309150 (1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol)

3D MOL for NP0309150 (1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol)

3D SDF for NP0309150 (1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol)

3D-SDF for NP0309150 (1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol)

PDB for NP0309150 (1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol)

3D PDB for NP0309150 (1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol)

SMILES for NP0309150 (1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol)

INCHI for NP0309150 (1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol)

Structure for NP0309150 (1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol)

3D Structure for NP0309150 (1-(5,6-dimethylhept-3-en-2-yl)-5a-methoxy-9a,11a-dimethyl-1h,2h,3h,3ah,5h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-8,9b-diol)