NP-MRD: Showing NP-Card for (4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione (NP0305885)

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Record Information

Version

2.0

Created at

2022-09-10 22:02:32 UTC

Updated at

2022-09-10 22:02:32 UTC

NP-MRD ID

NP0305885

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione

Description

(4AS,6bR,8S,8aR,12aR,12bR,13R,14aS,14bS)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-3,5,10-trione belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. (4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione is found in Morella rubra. Based on a literature review very few articles have been published on (4aS,6bR,8S,8aR,12aR,12bR,13R,14aS,14bS)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-3,5,10-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112200022D          

 35 39  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309112200022D          

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    1.1270   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 18  1  1  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 26 24  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 26 34  1  0  0  0  0
 20 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0305885

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C[C@H]2[C@]3(C)C[C@@H](O)[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5[C@@H](O)C[C@@]4(C)C3=CC(=O)[C@@]2(C)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O5/c1-25(2)14-19-28(6)12-17(32)24-27(5)10-9-20(33)26(3,4)23(27)16(31)13-30(24,8)18(28)11-21(34)29(19,7)15-22(25)35/h11,16-17,19,23-24,31-32H,9-10,12-15H2,1-8H3/t16-,17+,19-,23-,24+,27-,28+,29-,30-/m0/s1

> <INCHI_KEY>
XUTQPHXQIAVXGA-JBRIXDRLSA-N

> <FORMULA>
C30H44O5

> <MOLECULAR_WEIGHT>
484.677

> <EXACT_MASS>
484.318874517

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.47288270740828

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,6bR,8S,8aR,12aR,12bR,13R,14aS,14bS)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-3,5,10-trione

> <JCHEM_LOGP>
4.374317369666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.337669791828482

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.871066031422181

> <JCHEM_PKA_STRONGEST_BASIC>
-0.1284779882473771

> <JCHEM_POLAR_SURFACE_AREA>
91.67000000000002

> <JCHEM_REFRACTIVITY>
135.6331

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6bR,8S,8aR,12aR,12bR,13R,14aS,14bS)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1H-picene-3,5,10-trione

> <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      11.076   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.791   2.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.574  -1.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.804  -3.231   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.264   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7    8   11                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    2   10                                                  
CONECT   10    9                                                            
CONECT   11    6   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14    5   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   34                                                  
CONECT   21   20   14   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   34                                                  
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   26   20   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₅

Average Mass

484.6770 Da

Monoisotopic Mass

484.31887 Da

IUPAC Name

(4aS,6bR,8S,8aR,12aR,12bR,13R,14aS,14bS)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-3,5,10-trione

Traditional Name

(4aS,6bR,8S,8aR,12aR,12bR,13R,14aS,14bS)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1H-picene-3,5,10-trione

CAS Registry Number

Not Available

SMILES

CC1(C)C[C@H]2[C@]3(C)C[C@@H](O)[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5[C@@H](O)C[C@@]4(C)C3=CC(=O)[C@@]2(C)CC1=O

InChI Identifier

InChI=1S/C30H44O5/c1-25(2)14-19-28(6)12-17(32)24-27(5)10-9-20(33)26(3,4)23(27)16(31)13-30(24,8)18(28)11-21(34)29(19,7)15-22(25)35/h11,16-17,19,23-24,31-32H,9-10,12-15H2,1-8H3/t16-,17+,19-,23-,24+,27-,28+,29-,30-/m0/s1

InChI Key

XUTQPHXQIAVXGA-JBRIXDRLSA-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
Morella rubra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
Cyclohexenone
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.37	ChemAxon
pKa (Strongest Acidic)	14.87	ChemAxon
pKa (Strongest Basic)	-0.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	135.63 m³·mol⁻¹	ChemAxon
Polarizability	55.47 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

163031787

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione (NP0305885)

MOL for NP0305885 ((4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione)

3D MOL for NP0305885 ((4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione)

3D SDF for NP0305885 ((4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione)

3D-SDF for NP0305885 ((4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione)

PDB for NP0305885 ((4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione)

3D PDB for NP0305885 ((4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione)

SMILES for NP0305885 ((4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione)

INCHI for NP0305885 ((4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione)

Structure for NP0305885 ((4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione)

3D Structure for NP0305885 ((4as,6br,8s,8ar,12ar,12br,13r,14as,14bs)-8,13-dihydroxy-2,2,4a,6b,9,9,12a,14a-octamethyl-4,7,8,8a,11,12,12b,13,14,14b-decahydro-1h-picene-3,5,10-trione)