NP-MRD: Showing NP-Card for Roxburghiadiol A (NP0081684)

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Record Information

Version

2.0

Created at

2022-04-29 02:44:20 UTC

Updated at

2022-04-29 02:44:21 UTC

NP-MRD ID

NP0081684

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Roxburghiadiol A

Description

(1S,3R,6S,8S,9R,11S,12S,15R,16R)-12,16-dimethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecane-6,9-diol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Roxburghiadiol A is found in Aglaia roxburghiana and Swietenia macrophylla . Based on a literature review very few articles have been published on (1S,3R,6S,8S,9R,11S,12S,15R,16R)-12,16-dimethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecane-6,9-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204442D          

 31 35  0  0  1  0            999 V2000
    4.0480    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7677    0.7029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.1116    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.8601    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.1873    2.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 22 31  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292204442D          

 31 35  0  0  1  0            999 V2000
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 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  1  0  0  0
 27 29  1  1  0  0  0
 24 30  1  1  0  0  0
  2 30  1  1  0  0  0
 22 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081684

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3C[C@@H](O)[C@H]4C[C@@H](O)CC[C@@]44C[C@@]34CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O2/c1-18(2)19(3)7-8-20(4)22-10-11-27(6)25-16-24(31)23-15-21(30)9-12-28(23)17-29(25,28)14-13-26(22,27)5/h18,20-25,30-31H,3,7-17H2,1-2,4-6H3/t20-,21+,22-,23-,24-,25+,26-,27+,28-,29+/m1/s1

> <INCHI_KEY>
FLFAKBJFVNSCHC-MVJJFFPCSA-N

> <FORMULA>
C29H48O2

> <MOLECULAR_WEIGHT>
428.701

> <EXACT_MASS>
428.365430786

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
53.77012180131798

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,6S,8S,9R,11S,12S,15R,16R)-12,16-dimethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-6,9-diol

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
5.840876672666666

> <ALOGPS_LOGS>
-5.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.41946184827767

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.750208918563036

> <JCHEM_PKA_STRONGEST_BASIC>
-2.691009211408388

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
128.23209999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.87e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,6S,8S,9R,11S,12S,15R,16R)-12,16-dimethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-6,9-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       7.556   2.761   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.033   1.312   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.026   0.135   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.542   0.406   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.065   1.854   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.072   3.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.604   1.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.032   0.325   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.757  -0.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.549   3.020   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.075   2.809   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.020   4.025   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.545   3.815   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.126   2.388   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.491   5.030   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.016   4.820   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.910   6.457   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.969   4.447   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.737   3.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.173  -1.089   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.502  -1.314   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.986  -1.585   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.994  -0.407   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.517   1.041   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.524   2.218   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.008   1.947   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.485   0.499   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.478  -0.678   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.969   0.228   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.040   2.489   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.463  -3.033   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   24   30                                             
CONECT    3    2    4   21                                                  
CONECT    4    3    5    9   20                                             
CONECT    5    4    6    7   19                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   10                                                            
CONECT   19    5                                                            
CONECT   20    4                                                            
CONECT   21    3   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23    2   25   30                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27                                                            
CONECT   30   24    2                                                       
CONECT   31   22                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₈O₂

Average Mass

428.7010 Da

Monoisotopic Mass

428.36543 Da

IUPAC Name

(1S,3R,6S,8S,9R,11S,12S,15R,16R)-12,16-dimethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-6,9-diol

Traditional Name

(1S,3R,6S,8S,9R,11S,12S,15R,16R)-12,16-dimethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-6,9-diol

CAS Registry Number

Not Available

SMILES

CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3C[C@@H](O)[C@H]4C[C@@H](O)CC[C@@]44C[C@@]34CC[C@]12C

InChI Identifier

InChI=1S/C29H48O2/c1-18(2)19(3)7-8-20(4)22-10-11-27(6)25-16-24(31)23-15-21(30)9-12-28(23)17-29(25,28)14-13-26(22,27)5/h18,20-25,30-31H,3,7-17H2,1-2,4-6H3/t20-,21+,22-,23-,24-,25+,26-,27+,28-,29+/m1/s1

InChI Key

FLFAKBJFVNSCHC-MVJJFFPCSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aglaia roxburghiana	Plant	KNApSAcK
Swietenia macrophylla	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
3-beta-hydroxysteroid
Hydroxysteroid
6-hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
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	5.19	ALOGPS
logP	5.84	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	14.75	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	128.23 m³·mol⁻¹	ChemAxon
Polarizability	53.77 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

14680321

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Roxburghiadiol A (NP0081684)

MOL for NP0081684 (Roxburghiadiol A)

3D MOL for NP0081684 (Roxburghiadiol A)

3D SDF for NP0081684 (Roxburghiadiol A)

3D-SDF for NP0081684 (Roxburghiadiol A)

PDB for NP0081684 (Roxburghiadiol A)

3D PDB for NP0081684 (Roxburghiadiol A)

SMILES for NP0081684 (Roxburghiadiol A)

INCHI for NP0081684 (Roxburghiadiol A)

Structure for NP0081684 (Roxburghiadiol A)

3D Structure for NP0081684 (Roxburghiadiol A)