NP-MRD: Showing NP-Card for (2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate (NP0278645)

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Record Information

Version

2.0

Created at

2022-09-09 03:44:54 UTC

Updated at

2022-09-09 03:44:54 UTC

NP-MRD ID

NP0278645

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate

Description

(2S)-1-[(1S,2R,4aR,4bR,10aR)-2,4a,8,8,10a-pentamethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred. (2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate is found in Doris verrucosa. Based on a literature review very few articles have been published on (2S)-1-[(1S,2R,4aR,4bR,10aR)-2,4a,8,8,10a-pentamethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092205442D          

 33 35  0  0  1  0            999 V2000
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309092205442D          

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 14 15  1  0  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  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  1  0  0  0
  6 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0278645

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@]2(C)[C@H]3CCCC(C)(C)C3=CC[C@]2(C)[C@H]1C(=O)OC[C@H](COC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O6/c1-17-10-13-26(6)22-9-8-12-25(4,5)21(22)11-14-27(26,7)23(17)24(30)32-16-20(33-19(3)29)15-31-18(2)28/h11,17,20,22-23H,8-10,12-16H2,1-7H3/t17-,20+,22+,23-,26-,27-/m1/s1

> <INCHI_KEY>
MJBRTJPUYWTKEQ-GNXLMVSSSA-N

> <FORMULA>
C27H42O6

> <MOLECULAR_WEIGHT>
462.627

> <EXACT_MASS>
462.298139072

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.94645713999345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(1S,2R,4aR,4bR,10aR)-2,4a,8,8,10a-pentamethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate

> <JCHEM_LOGP>
4.665363737333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.554391521694543

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
125.53929999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(1S,2R,4aR,4bR,10aR)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1H-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.002 -13.860   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.670 -11.550   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.005 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.339 -10.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.673 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.006 -12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.006 -13.860   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.673 -14.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.662 -15.810   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.683 -15.810   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.672 -12.320   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.338 -13.090   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   28                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   28                                             
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   18   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   11   16   29                                             
CONECT   29   28                                                            
CONECT   30    6   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
(2S)-1-[(1S,2R,4AR,4BR,10ar)-2,4a,8,8,10a-pentamethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetic acid	Generator

Chemical Formula

C₂₇H₄₂O₆

Average Mass

462.6270 Da

Monoisotopic Mass

462.29814 Da

IUPAC Name

(2S)-1-[(1S,2R,4aR,4bR,10aR)-2,4a,8,8,10a-pentamethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate

Traditional Name

(2S)-1-[(1S,2R,4aR,4bR,10aR)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1H-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@]2(C)[C@H]3CCCC(C)(C)C3=CC[C@]2(C)[C@H]1C(=O)OC[C@H](COC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C27H42O6/c1-17-10-13-26(6)22-9-8-12-25(4,5)21(22)11-14-27(26,7)23(17)24(30)32-16-20(33-19(3)29)15-31-18(2)28/h11,17,20,22-23H,8-10,12-16H2,1-7H3/t17-,20+,22+,23-,26-,27-/m1/s1

InChI Key

MJBRTJPUYWTKEQ-GNXLMVSSSA-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
Doris verrucosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Not Available

Direct Parent

Steroids and steroid derivatives

Alternative Parents

Substituents

Steroid
Sesquiterpenoid
Phenanthrene
Hydrophenanthrene
Tricarboxylic acid or derivatives
Glycerolipid
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.67	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	125.54 m³·mol⁻¹	ChemAxon
Polarizability	51.95 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

10183023

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21574737

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate (NP0278645)

MOL for NP0278645 ((2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate)

3D MOL for NP0278645 ((2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate)

3D SDF for NP0278645 ((2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate)

3D-SDF for NP0278645 ((2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate)

PDB for NP0278645 ((2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate)

3D PDB for NP0278645 ((2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate)

SMILES for NP0278645 ((2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate)

INCHI for NP0278645 ((2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate)

Structure for NP0278645 ((2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate)

3D Structure for NP0278645 ((2s)-1-[(1s,2r,4ar,4br,10ar)-2,4a,8,8,10a-pentamethyl-2,3,4,4b,5,6,7,10-octahydro-1h-phenanthrene-1-carbonyloxy]-3-(acetyloxy)propan-2-yl acetate)