NP-MRD: Showing NP-Card for (1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid (NP0190728)

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Record Information

Version

2.0

Created at

2022-09-04 07:27:16 UTC

Updated at

2022-09-04 07:27:16 UTC

NP-MRD ID

NP0190728

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid

Description

Bacosine belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid is found in Bacopa monnieri. (1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid was first documented in 2008 (PMID: 18478974). Based on a literature review a small amount of articles have been published on Bacosine (PMID: 24449518) (PMID: 34894460) (PMID: 32325509) (PMID: 21154199).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042209272D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042209272D          

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    3.9398   -5.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5382   -5.0935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6119   -5.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4868   -4.3477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 11 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  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 18 31  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  1  6  0  0  0
 15 33  1  0  0  0  0
 33  4  1  6  0  0  0
  7 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190728

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CC[C@]2(C)CC[C@@]3([C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-18(2)19-10-13-27(5)16-17-30(25(32)33)20(24(19)27)8-9-22-28(6)14-12-23(31)26(3,4)21(28)11-15-29(22,30)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23+,24+,27+,28-,29+,30+/m0/s1

> <INCHI_KEY>
CLOUCVRNYSHRCF-CHVGUTEKSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.711

> <EXACT_MASS>
456.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.444559430204244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5R,8R,9R,10R,13R,14R,17R,19R)-17-hydroxy-1,5,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-2-carboxylic acid

> <JCHEM_LOGP>
6.639739080000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.489433389651015

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.857195027923688

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351227687609107

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
132.62550000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R,8R,9R,10R,13R,14R,17R,19R)-17-hydroxy-1,5,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-2-carboxylic acid

> <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       0.977  -4.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.105  -5.454   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.577  -5.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.762  -6.956   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.346  -7.561   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.484  -9.094   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.985  -9.438   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.061 -10.670   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.735 -10.783   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.275 -10.806   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.065  -9.484   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.814 -10.830   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.046 -11.754   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.024 -12.151   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.315  -8.139   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.105  -6.817   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.645  -6.841   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.395  -8.186   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.935  -8.209   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.185  -6.864   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.725  -6.888   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.265  -6.911   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.014  -8.256   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.554  -8.280   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.224  -9.578   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.663 -10.127   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.934 -11.090   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.684  -9.555   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.894 -10.876   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.354 -10.853   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.605  -9.508   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.742 -11.042   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.775  -8.116   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   33                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15   31                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16   33                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20   21   28                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   19   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   18   11   32                                             
CONECT   32   31                                                            
CONECT   33   15    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₃

Average Mass

456.7110 Da

Monoisotopic Mass

456.36035 Da

IUPAC Name

(1R,2S,5R,8R,9R,10R,13R,14R,17R,19R)-17-hydroxy-1,5,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-2-carboxylic acid

Traditional Name

(1R,2S,5R,8R,9R,10R,13R,14R,17R,19R)-17-hydroxy-1,5,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1CC[C@]2(C)CC[C@@]3([C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(O)=O

InChI Identifier

InChI=1S/C30H48O3/c1-18(2)19-10-13-27(5)16-17-30(25(32)33)20(24(19)27)8-9-22-28(6)14-12-23(31)26(3,4)21(28)11-15-29(22,30)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23+,24+,27+,28-,29+,30+/m0/s1

InChI Key

CLOUCVRNYSHRCF-CHVGUTEKSA-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
Bacopa monnieri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
19-oxosteroid
Oxosteroid
Steroid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
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	6.64	ChemAxon
pKa (Strongest Acidic)	4.86	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	132.63 m³·mol⁻¹	ChemAxon
Polarizability	54.44 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00029785

Chemspider ID

28536201

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71312547

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Singh R, Ramakrishna R, Bhateria M, Bhatta RS: In vitro evaluation of Bacopa monniera extract and individual constituents on human recombinant monoamine oxidase enzymes. Phytother Res. 2014 Sep;28(9):1419-22. doi: 10.1002/ptr.5116. Epub 2014 Jan 21. [PubMed:24449518 ]
Yeggoni DP, Rachamallu A, Subramanyam R: Comparative binding studies of bacosine with human serum albumin and alpha-1-acid glycoprotein biophysical evaluation and computational approach. J Pharm Biomed Anal. 2022 Feb 5;209:114478. doi: 10.1016/j.jpba.2021.114478. Epub 2021 Nov 24. [PubMed:34894460 ]
Ritter S, Urmann C, Herzog R, Glaser J, Bieringer S, Geisberger T, Eisenreich W, Riepl H: Where Is Bacosine in Commercially Available Bacopa monnieri? Planta Med. 2020 May;86(8):565-570. doi: 10.1055/a-1137-4289. Epub 2020 Apr 23. [PubMed:32325509 ]
Ghosh T, Maity TK, Singh J: Antihyperglycemic activity of bacosine, a triterpene from Bacopa monnieri, in alloxan-induced diabetic rats. Planta Med. 2011 May;77(8):804-8. doi: 10.1055/s-0030-1250600. Epub 2010 Dec 10. [PubMed:21154199 ]
Deb DD, Kapoor P, Dighe RP, Padmaja R, Anand MS, D'Souza P, Deepak M, Murali B, Agarwal A: In vitro safety evaluation and anticlastogenic effect of BacoMind on human lymphocytes. Biomed Environ Sci. 2008 Feb;21(1):7-23. doi: 10.1016/S0895-3988(08)60002-1. [PubMed:18478974 ]
LOTUS database [Link]

Showing NP-Card for (1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid (NP0190728)

MOL for NP0190728 ((1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid)

3D MOL for NP0190728 ((1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid)

3D SDF for NP0190728 ((1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid)

3D-SDF for NP0190728 ((1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid)

PDB for NP0190728 ((1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid)

3D PDB for NP0190728 ((1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid)

SMILES for NP0190728 ((1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid)

INCHI for NP0190728 ((1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid)

Structure for NP0190728 ((1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid)

3D Structure for NP0190728 ((1r,3ar,5as,5br,7ar,9r,11ar,11br,13ar,13br)-9-hydroxy-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-5a-carboxylic acid)