NP-MRD: Showing NP-Card for 2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate (NP0204533)

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Record Information

Version

2.0

Created at

2022-09-05 00:13:36 UTC

Updated at

2022-09-05 00:13:36 UTC

NP-MRD ID

NP0204533

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate

Description

24-Nor-9,11-seco-11-acetoxy-3,6-dihydroxycholest-7,22-dien-9-one, also known as NSADC, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, 24-nor-9,11-seco-11-acetoxy-3,6-dihydroxycholest-7,22-dien-9-one is considered to be a secosteroid. 2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate is found in Gersemia fruticosa. Based on a literature review very few articles have been published on 24-nor-9,11-seco-11-acetoxy-3,6-dihydroxycholest-7,22-dien-9-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309052202132D          

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  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  2  0  0  0  0
  9 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204533

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)\C=C\[C@@H](C)[C@H]1CC[C@@H](C2=C[C@H](O)[C@H]3C[C@@H](O)CC[C@]3(C)C2=O)[C@]1(C)CCOC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O5/c1-17(2)7-8-18(3)22-9-10-23(27(22,5)13-14-33-19(4)29)21-16-25(31)24-15-20(30)11-12-28(24,6)26(21)32/h7-8,16-18,20,22-25,30-31H,9-15H2,1-6H3/b8-7+/t18-,20+,22-,23+,24-,25+,27-,28+/m1/s1

> <INCHI_KEY>
HURHMFSVMAENRK-NQZWFRJXSA-N

> <FORMULA>
C28H44O5

> <MOLECULAR_WEIGHT>
460.655

> <EXACT_MASS>
460.318874517

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.86280534132743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R,2R,5R)-2-[(4S,4aS,6S,8aS)-4,6-dihydroxy-8a-methyl-1-oxo-1,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]-1-methyl-5-[(2R,3E)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate

> <JCHEM_LOGP>
4.623914639666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.320129186071412

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.414074017520765

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6918870534086583

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
132.25039999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1R,2R,5R)-2-[(4S,4aS,6S,8aS)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2R,3E)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.022  -5.945   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.312  -6.715   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.312  -8.255   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.646  -5.945   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.979  -6.715   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.313  -5.945   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.647  -6.715   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.742  -7.961   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.273  -5.308   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.503  -3.975   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.963  -3.975   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.193  -2.641   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.653  -2.641   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.963  -1.307   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.193   0.026   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.963   1.360   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.193   2.694   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.503   1.360   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.273   0.026   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.503  -1.307   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.043  -1.307   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.273  -2.641   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.813  -2.641   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.805  -5.469   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.125  -6.976   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.791  -7.746   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.630  -9.277   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.223  -9.904   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.876 -10.182   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.715 -11.714   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.961 -12.619   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.368 -11.993   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.800 -14.151   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   26                                             
CONECT    8    7                                                            
CONECT    9    7   10   24                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   10   23                                                  
CONECT   23   22                                                            
CONECT   24    9   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    7   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
24-Nor-9,11-seco-11-acetyloxy-3beta,6alpha-dihydroxycholest-7,22(e)-dien-9-one	MeSH
NSADC	MeSH

Chemical Formula

C₂₈H₄₄O₅

Average Mass

460.6550 Da

Monoisotopic Mass

460.31887 Da

IUPAC Name

2-[(1R,2R,5R)-2-[(4S,4aS,6S,8aS)-4,6-dihydroxy-8a-methyl-1-oxo-1,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]-1-methyl-5-[(2R,3E)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate

Traditional Name

2-[(1R,2R,5R)-2-[(4S,4aS,6S,8aS)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2R,3E)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate

CAS Registry Number

Not Available

SMILES

CC(C)\C=C\[C@@H](C)[C@H]1CC[C@@H](C2=C[C@H](O)[C@H]3C[C@@H](O)CC[C@]3(C)C2=O)[C@]1(C)CCOC(C)=O

InChI Identifier

InChI=1S/C28H44O5/c1-17(2)7-8-18(3)22-9-10-23(27(22,5)13-14-33-19(4)29)21-16-25(31)24-15-20(30)11-12-28(24,6)26(21)32/h7-8,16-18,20,22-25,30-31H,9-15H2,1-6H3/b8-7+/t18-,20+,22-,23+,24-,25+,27-,28+/m1/s1

InChI Key

HURHMFSVMAENRK-NQZWFRJXSA-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
Gersemia fruticosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Cyclohexenone
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Vitamin D3 and derivatives (LMST03020680 )

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	4.62	ChemAxon
pKa (Strongest Acidic)	14.41	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	132.25 m³·mol⁻¹	ChemAxon
Polarizability	53.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

8542456

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10367008

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate (NP0204533)

MOL for NP0204533 (2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate)

3D MOL for NP0204533 (2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate)

3D SDF for NP0204533 (2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate)

3D-SDF for NP0204533 (2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate)

PDB for NP0204533 (2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate)

3D PDB for NP0204533 (2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate)

SMILES for NP0204533 (2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate)

INCHI for NP0204533 (2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate)

Structure for NP0204533 (2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate)

3D Structure for NP0204533 (2-[(1r,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate)