NP-MRD: Showing NP-Card for suberosol (NP0187421)

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Record Information

Version

2.0

Created at

2022-09-04 03:35:25 UTC

Updated at

2022-09-04 03:35:25 UTC

NP-MRD ID

NP0187421

Secondary Accession Numbers

None

Natural Product Identification

Common Name

suberosol

Description

Suberosol 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. suberosol is found in Polyalthia suberosa. suberosol was first documented in 1993 (PMID: 8377018). Based on a literature review very few articles have been published on suberosol (PMID: 12205865).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042205352D          

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M  END

     RDKit          3D

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M  END


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 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  7 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  1  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0187421

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=C)CC[C@@H](C)[C@H]1C[C@H](O)[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@@H](O)CC[C@]4(C)C3=CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C31H50O2/c1-19(2)20(3)10-11-21(4)24-18-27(33)31(9)23-12-13-25-28(5,6)26(32)15-16-29(25,7)22(23)14-17-30(24,31)8/h12,14,19,21,24-27,32-33H,3,10-11,13,15-18H2,1-2,4-9H3/t21-,24-,25+,26+,27+,29-,30-,31-/m1/s1

> <INCHI_KEY>
MJRURUDEESYVHI-UJZFCZBUSA-N

> <FORMULA>
C31H50O2

> <MOLECULAR_WEIGHT>
454.739

> <EXACT_MASS>
454.38108085

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
57.1624175025377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,7R,11R,12S,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-diene-5,12-diol

> <JCHEM_LOGP>
6.458892563999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.618794118226784

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2728515691272465

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
140.65290000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,7R,11R,12S,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-diene-5,12-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      13.320  -0.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.320  -2.250   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.987  -3.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.653  -2.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.319  -3.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.319  -4.560   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.986  -2.250   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.579  -2.877   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.548  -1.732   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.017  -1.893   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.318  -0.399   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.787  -0.238   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.842   1.066   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.336   1.386   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.860   2.851   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.891   3.995   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.415   5.460   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.055   4.737   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.467   6.674   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.445   6.604   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.969   8.069   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.951   6.284   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.427   4.820   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.397   3.675   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.903   3.355   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.873   2.211   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.379   1.890   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.855   0.426   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.825  -0.719   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.289  -1.195   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.654  -3.020   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.988  -2.250   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.654  -4.560   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   29                                             
CONECT   12   11                                                            
CONECT   13   11   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   16   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   13   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    7   11   30                                             
CONECT   30   29                                                            
CONECT   31    2   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₅₀O₂

Average Mass

454.7390 Da

Monoisotopic Mass

454.38108 Da

IUPAC Name

(2S,5S,7R,11R,12S,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-diene-5,12-diol

Traditional Name

(2S,5S,7R,11R,12S,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-diene-5,12-diol

CAS Registry Number

Not Available

SMILES

CC(C)C(=C)CC[C@@H](C)[C@H]1C[C@H](O)[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@@H](O)CC[C@]4(C)C3=CC[C@]12C

InChI Identifier

InChI=1S/C31H50O2/c1-19(2)20(3)10-11-21(4)24-18-27(33)31(9)23-12-13-25-28(5,6)26(32)15-16-29(25,7)22(23)14-17-30(24,31)8/h12,14,19,21,24-27,32-33H,3,10-11,13,15-18H2,1-2,4-9H3/t21-,24-,25+,26+,27+,29-,30-,31-/m1/s1

InChI Key

MJRURUDEESYVHI-UJZFCZBUSA-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
Polyalthia suberosa	LOTUS Database	35616633

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

Triterpenoid
Ergosterol-skeleton
3-hydroxy-delta-7-steroid
3-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
14-alpha-methylsteroid
3-beta-hydroxysteroid
Delta-7-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

diol (CHEBI:66531 )
tetracyclic triterpenoid (CHEBI:66531 )

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	6.46	ChemAxon
pKa (Strongest Acidic)	19.62	ChemAxon
pKa (Strongest Basic)	-0.27	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	140.65 m³·mol⁻¹	ChemAxon
Polarizability	57.16 Å³	ChemAxon
Number of Rings	4	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

C00047355

Chemspider ID

10214105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21592340

PDB ID

Not Available

ChEBI ID

66531

Good Scents ID

Not Available

References

General References

Zhao W, Fan C, Qin G: [A study on major chemical components of Uvaria grandiflora]. Zhongguo Zhong Yao Za Zhi. 1999 Aug;24(8):476-7, 510-1. [PubMed:12205865 ]
Li HY, Sun NJ, Kashiwada Y, Sun L, Snider JV, Cosentino LM, Lee KH: Anti-AIDS agents, 9. Suberosol, a new C31 lanostane-type triterpene and anti-HIV principle from Polyalthia suberosa. J Nat Prod. 1993 Jul;56(7):1130-3. doi: 10.1021/np50097a017. [PubMed:8377018 ]
LOTUS database [Link]

Showing NP-Card for suberosol (NP0187421)

MOL for NP0187421 (suberosol)

3D MOL for NP0187421 (suberosol)

3D SDF for NP0187421 (suberosol)

3D-SDF for NP0187421 (suberosol)

PDB for NP0187421 (suberosol)

3D PDB for NP0187421 (suberosol)

SMILES for NP0187421 (suberosol)

INCHI for NP0187421 (suberosol)

Structure for NP0187421 (suberosol)

3D Structure for NP0187421 (suberosol)