NP-MRD: Showing NP-Card for Hopan-22-ol (NP0084103)

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Record Information

Version

1.0

Created at

2022-04-29 04:56:28 UTC

Updated at

2022-04-29 04:56:28 UTC

NP-MRD ID

NP0084103

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hopan-22-ol

Description

Hopan-22-ol, also known as 22-hopanol or 22-hydroxyhopane, 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). Thus, hopan-22-ol is considered to be a hopanoid lipid molecule. Hopan-22-ol is found in Acetobacter pasteurianus, Adiantum capillus-veneris, Adiantum raddianum, Adiantum edgeworthii, Adiantum pedatum, Aleuritopteris kuhnii, Alsophila gigantea, Alsophila podophylla, Alsophila spinulosa, Asterella blumeana, Azolla nilotica, Cheilanthes marantae, Cheiropleuria bicuspis, Cyathea lepifera, Davallia mariesii, Dryopteris crassirhizoma, Fossombronia pusilla, Laurencia dendroidea, Lepisorus contortus, Lophosoria quadripinnata, Oleandra wallichii, Plagiochasma rupestre, Plagiogyria glauca, Pleopeltis polypodioides, Polypodium aureum and Polypodium formosanum. It was first documented in 2011 (PMID: 21261296). Hopan-22-ol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv1533006041518142D          
 
 36 40  0  0  1  0            999 V2000
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   15.3659  -11.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 36  1  6  0  0  0
M  END

     RDKit          3D

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M  END

 
  Mrv1533006041518142D          
 
 36 40  0  0  1  0            999 V2000
   14.6660  -12.1456    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   18.2334  -10.9333    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1985  -10.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4471  -11.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0259  -12.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0313  -12.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2428  -11.5130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9450  -14.0839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.0980  -10.5001    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.5195  -10.5071    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0259  -10.7172    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6579  -12.9630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  1  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  1  0  0  0
  4 11  1  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
  5 14  1  6  0  0  0
  6 15  1  0  0  0  0
  8 16  1  0  0  0  0
  9 17  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  1  0  0  0  0
 16 20  1  0  0  0  0
 16 21  1  0  0  0  0
 16 22  1  0  0  0  0
 18 23  1  0  0  0  0
 18 24  1  0  0  0  0
 18 25  1  6  0  0  0
 23 26  1  0  0  0  0
 24 27  1  0  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
  8 15  1  0  0  0  0
 11 12  1  0  0  0  0
 17 20  1  0  0  0  0
 19 23  1  0  0  0  0
 26 27  1  0  0  0  0
  8 32  1  6  0  0  0
 12 33  1  1  0  0  0
 23 34  1  1  0  0  0
 26 35  1  1  0  0  0
  1 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0084103

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2(C)[C@@]1([H])CC[C@]1(C)[C@]2([H])CC[C@]2([H])[C@@]3(C)CCCC(C)(C)[C@]3([H])CC[C@@]12C)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C30H52O/c1-25(2)15-9-16-28(6)22(25)14-19-30(8)24(28)11-10-23-27(5)17-12-20(26(3,4)31)21(27)13-18-29(23,30)7/h20-24,31H,9-19H2,1-8H3/t20-,21-,22-,23+,24+,27-,28-,29+,30+/m0/s1

> <INCHI_KEY>
PNJBOAVCVAVRGR-UDCAXGDQSA-N

> <FORMULA>
C30H52O

> <MOLECULAR_WEIGHT>
428.745

> <EXACT_MASS>
428.401816294

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
54.757945188547495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R,2R,5S,6S,9S,10R,13R,14S,19S)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-6-yl]propan-2-ol

> <ALOGPS_LOGP>
6.47

> <JCHEM_LOGP>
7.633342403999999

> <ALOGPS_LOGS>
-7.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.477491190507745

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8403453532719122

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
131.3744

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.34e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diplopterol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      27.376 -22.672   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.710 -23.454   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.044 -23.448   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.319 -21.126   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.050 -22.685   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.710 -24.999   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.683 -22.216   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.037 -24.986   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.690 -22.658   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.031 -21.896   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.730 -20.363   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.056 -21.146   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.377 -23.461   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.043 -24.231   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.363 -25.762   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.690 -25.762   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.364 -23.448   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.403 -20.389   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.703 -22.704   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.364 -24.986   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.980 -27.476   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.402 -27.398   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.710 -21.165   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      31.416 -18.865   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      31.312 -21.465   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      34.036 -20.409   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      33.970 -18.891   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      34.435 -21.896   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      35.515 -22.983   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      33.658 -23.228   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      35.920 -21.491   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0      26.031 -26.290   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      30.050 -19.600   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      32.703 -19.613   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      35.515 -20.005   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      27.361 -24.198   0.000  0.00  0.00           H+0
CONECT    1    2    3    4   36                                             
CONECT    2    1    5    6    7                                             
CONECT    3    1    8    9   10                                             
CONECT    4    1   11                                                       
CONECT    5    2   12   13   14                                             
CONECT    6    2   15                                                       
CONECT    7    2                                                            
CONECT    8    3   16   15   32                                             
CONECT    9    3   17                                                       
CONECT   10    3                                                            
CONECT   11    4   12                                                       
CONECT   12    5   18   11   33                                             
CONECT   13    5   19                                                       
CONECT   14    5                                                            
CONECT   15    6    8                                                       
CONECT   16    8   20   21   22                                             
CONECT   17    9   20                                                       
CONECT   18   12   23   24   25                                             
CONECT   19   13   23                                                       
CONECT   20   16   17                                                       
CONECT   21   16                                                            
CONECT   22   16                                                            
CONECT   23   18   26   19   34                                             
CONECT   24   18   27                                                       
CONECT   25   18                                                            
CONECT   26   23   28   27   35                                             
CONECT   27   24   26                                                       
CONECT   28   26   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32    8                                                            
CONECT   33   12                                                            
CONECT   34   23                                                            
CONECT   35   26                                                            
CONECT   36    1                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
22-Hopanol	ChEBI
22-Hydroxyhopane	ChEBI
29,29-Dimethyl-21,30-dinorgammaceran-29-ol	ChEBI
A'-neogammaceran-22-ol	ChEBI
Diplopterol	ChEBI
Hopan-22-ol	MeSH, KEGG

Chemical Formula

C₃₀H₅₂O

Average Mass

428.7450 Da

Monoisotopic Mass

428.40182 Da

IUPAC Name

2-[(1R,2R,5S,6S,9S,10R,13R,14S,19S)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-6-yl]propan-2-ol

Traditional Name

diplopterol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2(C)[C@@]1([H])CC[C@]1(C)[C@]2([H])CC[C@]2([H])[C@@]3(C)CCCC(C)(C)[C@]3([H])CC[C@@]12C)C(C)(C)O

InChI Identifier

InChI=1S/C30H52O/c1-25(2)15-9-16-28(6)22(25)14-19-30(8)24(28)11-10-23-27(5)17-12-20(26(3,4)31)21(27)13-18-29(23,30)7/h20-24,31H,9-19H2,1-8H3/t20-,21-,22-,23+,24+,27-,28-,29+,30+/m0/s1

InChI Key

PNJBOAVCVAVRGR-UDCAXGDQSA-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
Acetobacter pasteurianus	LOTUS Database	35616633
Adiantum capillus-veneris	LOTUS Database	35616633
Adiantum cuneatum	LOTUS Database	35616633
Adiantum edgeworthii	LOTUS Database	35616633
Adiantum pedatum	LOTUS Database	35616633
Aleuritopteris kuhnii	LOTUS Database	35616633
Alsophila gigantea	LOTUS Database	35616633
Alsophila podophylla	LOTUS Database	35616633
Alsophila spinulosa	LOTUS Database	35616633
Asterella blumeana	LOTUS Database	35616633
Azolla nilotica	LOTUS Database	35616633
Cheilanthes marantae	LOTUS Database	35616633
Cheiropleuria bicuspis	LOTUS Database	35616633
Cyathea lepifera	LOTUS Database	35616633
Davallia mariesii	LOTUS Database	35616633
Dryopteris crassirhizoma	LOTUS Database	35616633
Fossombronia pusilla	LOTUS Database	35616633
Laurencia dendroidea	-	KNApSAcK
Lepisorus contortus	LOTUS Database	35616633
Lophosoria quadripinnata	LOTUS Database	35616633
Oleandra wallichii	LOTUS Database	35616633
Plagiochasma rupestre	LOTUS Database	35616633
Plagiogyria glauca	LOTUS Database	35616633
Pleopeltis polypodioides	LOTUS Database	35616633
Polypodium aureum	LOTUS Database	35616633
Polypodium formosanum	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

Triterpenoid
Hopane-skeleton
20-hydroxysteroid
Hydroxysteroid
Steroid
Tertiary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

tertiary alcohol (CHEBI:36484 )
hopanoid (CHEBI:36484 )
pentacyclic triterpenoid (CHEBI:36484 )
Hopanoids (C06309 )
Hopanoids (LMPR04000002 )

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	6.47	ALOGPS
logP	7.63	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	19.48	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	131.37 m³·mol⁻¹	ChemAxon
Polarizability	54.76 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

C06309

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

164874

PDB ID

Not Available

ChEBI ID

36484

Good Scents ID

Not Available

References

General References

Yang JH, Kondratyuk TP, Jermihov KC, Marler LE, Qiu X, Choi Y, Cao H, Yu R, Sturdy M, Huang R, Liu Y, Wang LQ, Mesecar AD, van Breemen RB, Pezzuto JM, Fong HH, Chen YG, Zhang HJ: Bioactive compounds from the fern Lepisorus contortus. J Nat Prod. 2011 Feb 25;74(2):129-36. doi: 10.1021/np100373f. Epub 2011 Jan 24. [PubMed:21261296 ]

Showing NP-Card for Hopan-22-ol (NP0084103)

MOL for NP0084103 (Hopan-22-ol)

3D MOL for NP0084103 (Hopan-22-ol)

3D SDF for NP0084103 (Hopan-22-ol)

3D-SDF for NP0084103 (Hopan-22-ol)

PDB for NP0084103 (Hopan-22-ol)

3D PDB for NP0084103 (Hopan-22-ol)

SMILES for NP0084103 (Hopan-22-ol)

INCHI for NP0084103 (Hopan-22-ol)

Structure for NP0084103 (Hopan-22-ol)

3D Structure for NP0084103 (Hopan-22-ol)