NP-MRD: Showing NP-Card for (3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one (NP0272522)

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Record Information

Version

2.0

Created at

2022-09-08 19:10:19 UTC

Updated at

2022-09-08 19:10:19 UTC

NP-MRD ID

NP0272522

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one

Description

(3R,6R)-3-[(2S,5S,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-1(17),9-dien-14-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one is found in Inonotus obliquus. Based on a literature review very few articles have been published on (3R,6R)-3-[(2S,5S,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-1(17),9-dien-14-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309082221102D          

 34 38  0  0  1  0            999 V2000
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M  END

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M  END

  Mrv1652309082221102D          

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    1.3416   -1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6168   -0.6798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3365    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411   -0.9702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0532   -1.1154    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  2  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7 27  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  6  0  0  0
  8 29  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0272522

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@H]1CC[C@H]([C@H]2CC[C@@]3(C)C4=CCC5C(C)(C)[C@@H](O)CC[C@]5(C)C4=CC[C@]23C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-26(2)22-10-9-21-20(28(22,5)15-14-23(26)31)13-17-29(6)19(12-16-30(21,29)7)18-8-11-24(27(3,4)33)34-25(18)32/h9,13,18-19,22-24,31,33H,8,10-12,14-17H2,1-7H3/t18-,19-,22?,23+,24-,28-,29-,30+/m1/s1

> <INCHI_KEY>
XQNCFMBNMADTHB-AJIBSGPHSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.694

> <EXACT_MASS>
470.339609961

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.67467606478159

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,6R)-3-[(2S,5S,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one

> <JCHEM_LOGP>
4.804508595333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.618794118233346

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.302778254453212

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7785392407181128

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
136.20800000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,6R)-3-[(2S,5S,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.660  -4.434   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.191  -2.988   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.522  -3.762   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.675  -2.717   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.682  -3.895   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.834  -3.624   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.357  -2.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.365  -0.998   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.888   0.451   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.404   0.722   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.396  -0.456   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.068   0.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.936  -0.506   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.881   0.710   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.301   2.137   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.246   3.352   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.771   3.142   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.716   4.357   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.662   5.573   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.501   5.303   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.932   3.412   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.352   1.715   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.406   0.499   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.987  -0.927   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.364  -1.985   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.089  -2.849   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.873  -1.904   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.504  -3.399   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.151  -1.269   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.628   0.179   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.144  -0.092   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.660  -0.363   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.183  -1.811   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.699  -2.082   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   33                                             
CONECT    3    2                                                            
CONECT    4    2    5   29                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   27                                             
CONECT   12   11                                                            
CONECT   13   11   14   25                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   17   23                                                       
CONECT   23   22   14   24                                                  
CONECT   24   23                                                            
CONECT   25   13   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    7   11   28                                             
CONECT   28   27                                                            
CONECT   29    8    4   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    2   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6940 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

(3R,6R)-3-[(2S,5S,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one

Traditional Name

(3R,6R)-3-[(2S,5S,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@H]1CC[C@H]([C@H]2CC[C@@]3(C)C4=CCC5C(C)(C)[C@@H](O)CC[C@]5(C)C4=CC[C@]23C)C(=O)O1

InChI Identifier

InChI=1S/C30H46O4/c1-26(2)22-10-9-21-20(28(22,5)15-14-23(26)31)13-17-29(6)19(12-16-30(21,29)7)18-8-11-24(27(3,4)33)34-25(18)32/h9,13,18-19,22-24,31,33H,8,10-12,14-17H2,1-7H3/t18-,19-,22?,23+,24-,28-,29-,30+/m1/s1

InChI Key

XQNCFMBNMADTHB-AJIBSGPHSA-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
Inonotus obliquus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Steroid lactone
3-hydroxy-delta-7-steroid
3-hydroxysteroid
14-alpha-methylsteroid
Hydroxysteroid
3-beta-hydroxysteroid
Delta-7-steroid
Steroid
Delta valerolactone
Delta_valerolactone
Oxane
Cyclic alcohol
Tertiary alcohol
Lactone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	4.8	ChemAxon
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-0.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	136.21 m³·mol⁻¹	ChemAxon
Polarizability	55.67 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

78436575

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583900

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one (NP0272522)

MOL for NP0272522 ((3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one)

3D MOL for NP0272522 ((3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one)

3D SDF for NP0272522 ((3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one)

3D-SDF for NP0272522 ((3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one)

PDB for NP0272522 ((3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one)

3D PDB for NP0272522 ((3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one)

SMILES for NP0272522 ((3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one)

INCHI for NP0272522 ((3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one)

Structure for NP0272522 ((3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one)

3D Structure for NP0272522 ((3r,6r)-3-[(1r,3ar,7s,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-6-(2-hydroxypropan-2-yl)oxan-2-one)