NP-MRD: Showing NP-Card for 3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol (NP0154932)

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Record Information

Version

2.0

Created at

2022-09-02 11:55:06 UTC

Updated at

2022-09-02 11:55:06 UTC

NP-MRD ID

NP0154932

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol

Description

6-(2-Hydroxypropan-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosane-4,17,20-triol belongs to the class of organic compounds known as hopanoids. These are terpenoids containing hopane skeleton(A'-Neogammacerane), a pentacyclic structure with four cyclohexane rings and one cyclopentane ring (and often, a side chain emerging from C30). 3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol is found in Trigastrotheca pentaphylla. 6-(2-Hydroxypropan-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosane-4,17,20-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261506382D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004261506382D          

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    1.3893   -1.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3040    0.0297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427    1.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2506   -1.6617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3238   -0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8208   -1.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3752   -1.7244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5937    1.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4700    0.3874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0662   -1.1184    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 19 27  1  0  0  0  0
 17 28  1  0  0  0  0
 15 29  1  0  0  0  0
 10 30  1  0  0  0  0
  8 31  1  0  0  0  0
  6 32  1  0  0  0  0
  3 33  1  0  0  0  0
  2 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154932

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1CCC2(C)C1C(O)CC1(C)C2CCC2C3(C)CCC(O)C(C)(C)C3C(O)CC12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H52O4/c1-25(2)22(33)12-14-28(6)21-10-9-20-27(5)13-11-17(26(3,4)34)23(27)18(31)15-29(20,7)30(21,8)16-19(32)24(25)28/h17-24,31-34H,9-16H2,1-8H3

> <INCHI_KEY>
USLXSBTYECTZSS-UHFFFAOYSA-N

> <FORMULA>
C30H52O4

> <MOLECULAR_WEIGHT>
476.742

> <EXACT_MASS>
476.386560154

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
57.40550279020874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(2-hydroxypropan-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-4,17,20-triol

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
3.7850017429999987

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.709255257823074

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.268735086800007

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7748901101266448

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
136.07490000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(2-hydroxypropan-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-4,17,20-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      14.920  -1.124   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.481  -0.575   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.271   0.747   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.521   2.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.981   2.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.191   0.793   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.941  -0.552   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.151  -1.874   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.611  -1.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.861  -0.505   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.651   0.817   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.902   2.162   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.362   2.185   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.572   0.864   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.321  -0.482   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.531  -1.803   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.991  -1.780   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.242  -0.435   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.032   0.887   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.019   2.047   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.603   1.442   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.740  -0.092   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.580  -1.105   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.420  -2.118   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.593  -2.265   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.568   0.055   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.680   2.284   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.201  -3.102   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.071  -1.827   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.999  -2.039   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.900  -3.219   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.442   2.139   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.811   0.723   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      13.190  -2.088   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   34                                             
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11   32                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9   31                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15   30                                             
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   10   16   29                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   14   20   27                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18   23                                                  
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   19                                                            
CONECT   28   17                                                            
CONECT   29   15                                                            
CONECT   30   10                                                            
CONECT   31    8                                                            
CONECT   32    6                                                            
CONECT   33    3                                                            
CONECT   34    2                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₂O₄

Average Mass

476.7420 Da

Monoisotopic Mass

476.38656 Da

IUPAC Name

6-(2-hydroxypropan-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-4,17,20-triol

Traditional Name

6-(2-hydroxypropan-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-4,17,20-triol

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1CCC2(C)C1C(O)CC1(C)C2CCC2C3(C)CCC(O)C(C)(C)C3C(O)CC12C

InChI Identifier

InChI=1S/C30H52O4/c1-25(2)22(33)12-14-28(6)21-10-9-20-27(5)13-11-17(26(3,4)34)23(27)18(31)15-29(20,7)30(21,8)16-19(32)24(25)28/h17-24,31-34H,9-16H2,1-8H3

InChI Key

USLXSBTYECTZSS-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
Mollugo pentaphylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hopanoids. These are terpenoids containing hopane skeleton(A'-Neogammacerane), a pentacyclic structure with four cyclohexane rings and one cyclopentane ring (and often, a side chain emerging from C30).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Hopanoids

Direct Parent

Hopanoids

Alternative Parents

Substituents

Hopane-skeleton
Triterpenoid
20-hydroxysteroid
12-hydroxysteroid
2-hydroxysteroid
Hydroxysteroid
Steroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Polyol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
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	4.09	ALOGPS
logP	3.79	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	14.27	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	136.07 m³·mol⁻¹	ChemAxon
Polarizability	57.41 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

3824975

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol (NP0154932)

MOL for NP0154932 (3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol)

3D MOL for NP0154932 (3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol)

3D SDF for NP0154932 (3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol)

3D-SDF for NP0154932 (3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol)

PDB for NP0154932 (3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol)

3D PDB for NP0154932 (3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol)

SMILES for NP0154932 (3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol)

INCHI for NP0154932 (3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol)

Structure for NP0154932 (3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol)

3D Structure for NP0154932 (3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysene-4,7,9-triol)