NP-MRD: Showing NP-Card for 6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol (NP0237209)

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Record Information

Version

2.0

Created at

2022-09-06 20:17:12 UTC

Updated at

2022-09-06 20:17:13 UTC

NP-MRD ID

NP0237209

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol

Description

(3Beta,24xi)-Cycloartane-3,24,25-triol belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety (3beta,24xi)-Cycloartane-3,24,25-triol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (3beta,24XI)-cycloartane-3,24,25-triol has been detected, but not quantified in, fruits. 6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol is found in Aglaia elliptica, Dysoxylum malabaricum, Euphorbia petiolata, Euphorbia sessiliflora, Mangifera indica and Trivalvaria costata. This could make (3beta,24XI)-cycloartane-3,24,25-triol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308502D          

 33 37  0  0  0  0            999 V2000
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 33 26  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 05061308502D          

 33 37  0  0  0  0            999 V2000
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    2.9682    1.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8121    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    1.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0311    2.5168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8779    3.4260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 17 16  1  0  0  0  0
 19  1  1  0  0  0  0
 19  8  1  0  0  0  0
 20 12  1  0  0  0  0
 20 19  1  0  0  0  0
 21  9  1  0  0  0  0
 22 10  1  0  0  0  0
 23 13  1  0  0  0  0
 24 11  1  0  0  0  0
 25  2  1  0  0  0  0
 25  3  1  0  0  0  0
 25 21  1  0  0  0  0
 25 23  1  0  0  0  0
 26  4  1  0  0  0  0
 26  5  1  0  0  0  0
 26 24  1  0  0  0  0
 27  6  1  0  0  0  0
 27 16  1  0  0  0  0
 27 20  1  0  0  0  0
 28  7  1  0  0  0  0
 28 14  1  0  0  0  0
 28 22  1  0  0  0  0
 28 27  1  0  0  0  0
 29 15  1  0  0  0  0
 29 18  1  0  0  0  0
 29 21  1  0  0  0  0
 30 17  1  0  0  0  0
 30 18  1  0  0  0  0
 30 22  1  0  0  0  0
 30 29  1  0  0  0  0
 31 23  1  0  0  0  0
 32 24  1  0  0  0  0
 33 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237209

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC(O)C(C)(C)O)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H52O3/c1-19(8-11-24(32)26(4,5)33)20-12-14-28(7)22-10-9-21-25(2,3)23(31)13-15-29(21)18-30(22,29)17-16-27(20,28)6/h19-24,31-33H,8-18H2,1-7H3

> <INCHI_KEY>
BKRIPHYESIGPJC-UHFFFAOYSA-N

> <FORMULA>
C30H52O3

> <MOLECULAR_WEIGHT>
460.7321

> <EXACT_MASS>
460.39164553

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
57.21383008542864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol

> <ALOGPS_LOGP>
5.61

> <JCHEM_LOGP>
5.407223568666668

> <ALOGPS_LOGS>
-5.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.325111733999549

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.849642780302801

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351325136321276

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
134.38079999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.86e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.968   6.757   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.007   0.186   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.855   0.858   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.435   8.556   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.274   8.286   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.735   5.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.172   1.221   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.074   5.119   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.985   0.725   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.501   0.996   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.019   6.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.031   2.635   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.993   4.257   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.756   1.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.523   4.528   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.071   5.342   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.555   5.071   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.039   4.799   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.548   5.330   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.603   4.114   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.993   1.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.025   2.445   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.516   2.809   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.544   6.125   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.523   1.632   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.490   7.340   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.064   4.164   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.541   2.716   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.516   3.351   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.032   3.622   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.032   2.538   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      13.125   4.698   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      14.705   6.395   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   25                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5   26                                                            
CONECT    6   27                                                            
CONECT    7   28                                                            
CONECT    8   11   19                                                       
CONECT    9   10   21                                                       
CONECT   10    9   22                                                       
CONECT   11    8   24                                                       
CONECT   12   14   20                                                       
CONECT   13   15   23                                                       
CONECT   14   12   28                                                       
CONECT   15   13   29                                                       
CONECT   16   17   27                                                       
CONECT   17   16   30                                                       
CONECT   18   29   30                                                       
CONECT   19    1    8   20                                                  
CONECT   20   12   19   27                                                  
CONECT   21    9   25   29                                                  
CONECT   22   10   28   30                                                  
CONECT   23   13   25   31                                                  
CONECT   24   11   26   32                                                  
CONECT   25    2    3   21   23                                             
CONECT   26    4    5   24   33                                             
CONECT   27    6   16   20   28                                             
CONECT   28    7   14   22   27                                             
CONECT   29   15   18   21   30                                             
CONECT   30   17   18   22   29                                             
CONECT   31   23                                                            
CONECT   32   24                                                            
CONECT   33   26                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
(3b,24XI)-cycloartane-3,24,25-triol	Generator
(3Β,24xi)-cycloartane-3,24,25-triol	Generator

Chemical Formula

C₃₀H₅₂O₃

Average Mass

460.7321 Da

Monoisotopic Mass

460.39165 Da

IUPAC Name

6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol

Traditional Name

6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol

CAS Registry Number

Not Available

SMILES

CC(CCC(O)C(C)(C)O)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(O)C4(C)C

InChI Identifier

InChI=1S/C30H52O3/c1-19(8-11-24(32)26(4,5)33)20-12-14-28(7)22-10-9-21-25(2,3)23(31)13-15-29(21)18-30(22,29)17-16-27(20,28)6/h19-24,31-33H,8-18H2,1-7H3

InChI Key

BKRIPHYESIGPJC-UHFFFAOYSA-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
Aglaia elliptica	LOTUS Database	35616633
Dysoxylum malabaricum	LOTUS Database	35616633
Euphorbia petiolata	LOTUS Database	35616633
Euphorbia sessiliflora	LOTUS Database	35616633
Mangifera indica	LOTUS Database	35616633
Trivalvaria costata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cycloartanols and derivatives

Direct Parent

Cycloartanols and derivatives

Alternative Parents

Not Available

Substituents

Not Available

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	5.61	ALOGPS
logP	5.41	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	134.38 m³·mol⁻¹	ChemAxon
Polarizability	57.21 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

HMDB0035998

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014807

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

14314548

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol (NP0237209)

MOL for NP0237209 (6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol)

3D MOL for NP0237209 (6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol)

3D SDF for NP0237209 (6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol)

3D-SDF for NP0237209 (6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol)

PDB for NP0237209 (6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol)

3D PDB for NP0237209 (6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol)

SMILES for NP0237209 (6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol)

INCHI for NP0237209 (6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol)

Structure for NP0237209 (6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol)

3D Structure for NP0237209 (6-{6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl}-2-methylheptane-2,3-diol)