NP-MRD: Showing NP-Card for 5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol (NP0143054)

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Record Information

Version

2.0

Created at

2022-09-01 21:43:44 UTC

Updated at

2022-09-01 21:43:44 UTC

NP-MRD ID

NP0143054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol

Description

3-Epimoretenol 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-Epimoretenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-epimoretenol has been detected, but not quantified in, fats and oils. 5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol is found in Celtis laevigata, Elateriospermum tapos, Euphorbia maculata, Euphorbia trigona, Ficus macrophylla, Swertia chirayita and Triadica sebifera. This could make 3-epimoretenol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241208162D          

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M  END

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M  END


  Mrv0541 02241208162D          

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 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 27  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  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
 23 27  1  0  0  0  0
 24 25  1  0  0  0  0
 24 30  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0143054

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1CCC2(C)C1CCC1(C)C2CCC2C3(C)CCC(O)C(C)(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-19(2)20-11-15-27(5)21(20)12-17-29(7)23(27)9-10-24-28(6)16-14-25(31)26(3,4)22(28)13-18-30(24,29)8/h20-25,31H,1,9-18H2,2-8H3

> <INCHI_KEY>
LFPVZIIPFONRSW-UHFFFAOYSA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.7174

> <EXACT_MASS>
426.386166222

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
54.09484979913826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2,9,14,18,18-hexamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol

> <ALOGPS_LOGP>
6.26

> <JCHEM_LOGP>
7.448046480999999

> <ALOGPS_LOGS>
-6.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.48943339017772

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351218351362649

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
130.90829999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.95e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2,9,14,18,18-hexamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.175  -2.169   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.840  -2.939   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.642  -2.163   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.505  -0.629   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.583  -1.717   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.175   0.911   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.175  -0.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.507   0.141   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.842  -0.629   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.842  -2.169   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -7.176  -2.939   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.735   0.200   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.840   1.681   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.505   2.451   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.826   1.681   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.826   0.141   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.826  -1.399   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.498  -4.120   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.507  -2.939   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.519  -4.120   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.161  -0.629   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.493   0.141   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.493   1.681   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.638   2.710   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.012   4.120   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.482   3.958   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.161   2.451   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.914   3.357   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.176   3.537   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.145   2.392   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.622   0.926   0.000  0.00  0.00           C+0
CONECT    1    2    7   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12   16                                             
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    1    6    8   12                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10                                                            
CONECT   12    4    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16    4   15   17   21                                             
CONECT   17   16                                                            
CONECT   18   19                                                            
CONECT   19    1   10   18   20                                             
CONECT   20   19                                                            
CONECT   21   16   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   15   23   26   28                                             
CONECT   28   27                                                            
CONECT   29   30                                                            
CONECT   30   24   29   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
3-Epi-moretenol	HMDB

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7174 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

1,2,9,14,18,18-hexamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol

Traditional Name

1,2,9,14,18,18-hexamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol

CAS Registry Number

Not Available

SMILES

CC(=C)C1CCC2(C)C1CCC1(C)C2CCC2C3(C)CCC(O)C(C)(C)C3CCC12C

InChI Identifier

InChI=1S/C30H50O/c1-19(2)20-11-15-27(5)21(20)12-17-29(7)23(27)9-10-24-28(6)16-14-25(31)26(3,4)22(28)13-18-30(24,29)8/h20-25,31H,1,9-18H2,2-8H3

InChI Key

LFPVZIIPFONRSW-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
Celtis laevigata	LOTUS Database	35616633
Elateriospermum tapos	LOTUS Database	35616633
Euphorbia maculata	LOTUS Database	35616633
Euphorbia trigona	LOTUS Database	35616633
Ficus macrophylla	LOTUS Database	35616633
Swertia chirata	LOTUS Database	35616633
Triadica sebifera	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
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	6.26	ALOGPS
logP	7.45	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	19.49	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	130.91 m³·mol⁻¹	ChemAxon
Polarizability	54.09 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

HMDB0035123

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013756

KNApSAcK ID

C00036122

Chemspider ID

525874

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

604951

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol (NP0143054)

MOL for NP0143054 (5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D MOL for NP0143054 (5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D SDF for NP0143054 (5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D-SDF for NP0143054 (5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

PDB for NP0143054 (5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D PDB for NP0143054 (5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

SMILES for NP0143054 (5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

INCHI for NP0143054 (5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

Structure for NP0143054 (5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D Structure for NP0143054 (5a,5b,8,8,11a,13b-hexamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)