NP-MRD: Showing NP-Card for (5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate (NP0264898)

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Record Information

Version

2.0

Created at

2022-09-08 08:40:56 UTC

Updated at

2022-09-08 08:40:56 UTC

NP-MRD ID

NP0264898

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate

Description

Hop-17(21)-en-3beta-ol acetate 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). (5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate is found in Centaurea ptosimopappoides. Based on a literature review very few articles have been published on Hop-17(21)-en-3beta-ol acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082210402D          

 34 38  0  0  1  0            999 V2000
    5.9273   -0.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3289   -0.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9056    0.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0806    0.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6791   -0.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8542   -0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4308    0.4000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.6736    1.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  5  6  1  0  0  0  0
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 30 31  1  6  0  0  0
 10 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END

     RDKit          3D

 86 90  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309082210402D          

 34 38  0  0  1  0            999 V2000
    5.9273   -0.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7178    1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984    1.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5586    2.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2921    1.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095    1.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9344    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3577    1.0830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2590    1.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6573    1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3502    1.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6736    1.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 23 27  2  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 18 30  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  6  0  0  0
 10 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0264898

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](OC(C)=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@]2(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C32H52O2/c1-20(2)22-12-16-29(6)23(22)13-18-31(8)25(29)10-11-26-30(7)17-15-27(34-21(3)33)28(4,5)24(30)14-19-32(26,31)9/h20,24-27H,10-19H2,1-9H3/t24-,25+,26+,27-,29-,30-,31+,32+/m0/s1

> <INCHI_KEY>
AKPPTDCKDJSINA-YRXYYLIWSA-N

> <FORMULA>
C32H52O2

> <MOLECULAR_WEIGHT>
468.766

> <EXACT_MASS>
468.396730914

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
58.58967566873417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,9R,10S,13R,14R,17S,19R)-1,2,9,14,18,18-hexamethyl-6-(propan-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5-en-17-yl acetate

> <JCHEM_LOGP>
7.7875803963333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.00377816438925

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
140.8657

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,9R,10S,13R,14R,17S,19R)-6-isopropyl-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5-en-17-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      11.064  -1.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.814  -0.505   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.354  -0.482   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.024   0.817   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.484   0.793   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.734  -0.552   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.194  -0.575   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.404   0.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.655  -0.599   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.154   2.092   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.364   3.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.824   3.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.074   2.045   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.284   3.367   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.864   0.723   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.115  -0.622   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.575  -0.645   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.785   0.676   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.245   0.653   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.893  -0.744   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.768  -0.507   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.184   0.098   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.047   1.632   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.207   2.645   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.664   2.146   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.909   4.156   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.545   1.975   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.204   3.320   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.744   3.343   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.534   2.022   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.350   3.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.694   2.115   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.987   2.951   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.724   3.655   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   15                                             
CONECT    9    8                                                            
CONECT   10    8   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   30                                             
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   30                                                  
CONECT   19   18   20   21   27                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   19   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   18   13   31                                             
CONECT   31   30                                                            
CONECT   32   10    5   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
HOP-17(21)-En-3b-ol acetate	Generator
HOP-17(21)-En-3b-ol acetic acid	Generator
HOP-17(21)-En-3beta-ol acetic acid	Generator
HOP-17(21)-En-3β-ol acetate	Generator
HOP-17(21)-En-3β-ol acetic acid	Generator

Chemical Formula

C₃₂H₅₂O₂

Average Mass

468.7660 Da

Monoisotopic Mass

468.39673 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C1=C2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](OC(C)=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@]2(C)CC1

InChI Identifier

InChI=1S/C32H52O2/c1-20(2)22-12-16-29(6)23(22)13-18-31(8)25(29)10-11-26-30(7)17-15-27(34-21(3)33)28(4,5)24(30)14-19-32(26,31)9/h20,24-27H,10-19H2,1-9H3/t24-,25+,26+,27-,29-,30-,31+,32+/m0/s1

InChI Key

AKPPTDCKDJSINA-YRXYYLIWSA-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
Centaurea ptosimopappoides	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
Steroid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

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

101280152

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate (NP0264898)

MOL for NP0264898 ((5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate)

3D MOL for NP0264898 ((5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate)

3D SDF for NP0264898 ((5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate)

3D-SDF for NP0264898 ((5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate)

PDB for NP0264898 ((5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate)

3D PDB for NP0264898 ((5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate)

SMILES for NP0264898 ((5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate)

INCHI for NP0264898 ((5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate)

Structure for NP0264898 ((5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate)

3D Structure for NP0264898 ((5ar,5br,7ar,9s,11ar,11br,13as,13br)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1h,2h,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13ah-cyclopenta[a]chrysen-9-yl acetate)