NP-MRD: Showing NP-Card for 9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol (NP0172591)

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Record Information

Version

2.0

Created at

2022-09-03 09:33:09 UTC

Updated at

2022-09-03 09:33:09 UTC

NP-MRD ID

NP0172591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol

Description

3,6-Ditigloyloxytropan-7-ol belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane. 3,6-Ditigloyloxytropan-7-ol is a very strong basic compound (based on its pKa). Outside of the human body, 3,6-Ditigloyloxytropan-7-ol has been detected, but not quantified in, fruits. 9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol is found in Myrtillocactus geometrizans, Peniocereus greggii and Peniocereus viperinus. This could make 3,6-ditigloyloxytropan-7-ol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061304442D          

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M  END

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M  END


  Mrv0541 05061304442D          

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M  END
> <DATABASE_ID>
NP0172591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCCC(C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)CC1C(O)C3

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-16-25(29)24-15-19(28)11-13-27(24,5)23(20)12-14-26(21,22)4/h17-19,21-22,24-25,28-29H,6-16H2,1-5H3

> <INCHI_KEY>
MPCLLXXLNXORCU-UHFFFAOYSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
51.14746108241461

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-5,8-diol

> <ALOGPS_LOGP>
5.69

> <JCHEM_LOGP>
5.760466409000001

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.398287459956563

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.702807643511896

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6914773041848523

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
121.94239999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-5,8-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       3.153 -10.179   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.487 -12.489   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.821 -12.489   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.418 -11.836   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.051 -12.910   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.154 -10.949   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.820 -10.179   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.488 -10.179   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.316  -8.647   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.823  -8.327   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.063 -13.551   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.544 -12.590   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.557 -13.231   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.038 -12.270   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.618 -10.942   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.129  -8.837   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.487 -10.949   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.821 -10.949   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.094 -12.406   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.099  -9.981   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.155 -10.179   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.593  -9.661   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.575 -11.446   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.112 -10.621   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.636  -9.157   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.562 -10.805   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.081 -11.766   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      21.600 -12.726   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      18.666  -8.012   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6    7    8                                                       
CONECT    7    6   17                                                       
CONECT    8    6   18                                                       
CONECT    9   10   21                                                       
CONECT   10    9   22                                                       
CONECT   11   13   19                                                       
CONECT   12   14   23                                                       
CONECT   13   11   27                                                       
CONECT   14   12   26                                                       
CONECT   15   19   24                                                       
CONECT   16   20   25                                                       
CONECT   17    1    2    7                                                  
CONECT   18    3    8   21                                                  
CONECT   19   11   15   28                                                  
CONECT   20   16   22   23                                                  
CONECT   21    9   18   26                                                  
CONECT   22   10   20   26                                                  
CONECT   23   12   20   27                                                  
CONECT   24   15   25   27                                                  
CONECT   25   16   24   29                                                  
CONECT   26    4   14   21   22                                             
CONECT   27    5   13   23   24                                             
CONECT   28   19                                                            
CONECT   29   25                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
Peniocerol	HMDB
(3b,5a,6a)-Cholest-8-ene-3,6-diol	Generator
(3Β,5α,6α)-cholest-8-ene-3,6-diol	Generator

Chemical Formula

C₂₇H₄₆O₂

Average Mass

402.6529 Da

Monoisotopic Mass

402.34978 Da

IUPAC Name

2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-5,8-diol

Traditional Name

2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-5,8-diol

CAS Registry Number

Not Available

SMILES

CC(C)CCCC(C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)CC1C(O)C3

InChI Identifier

InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-16-25(29)24-15-19(28)11-13-27(24,5)23(20)12-14-26(21,22)4/h17-19,21-22,24-25,28-29H,6-16H2,1-5H3

InChI Key

MPCLLXXLNXORCU-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
Myrtillocactus geometrizans	LOTUS Database	35616633
Peniocereus greggii	LOTUS Database	35616633
Peniocereus viperinus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane alkaloids

Alternative Parents

Substituents

Tropane alkaloid
Fatty acid ester
Dicarboxylic acid or derivatives
Piperidine
Fatty acyl
N-alkylpyrrolidine
Cyclic alcohol
Pyrrolidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	5.69	ALOGPS
logP	5.76	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	14.7	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.94 m³·mol⁻¹	ChemAxon
Polarizability	51.15 Å³	ChemAxon
Number of Rings	4	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

HMDB0029325

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000386

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

12960452

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol (NP0172591)

MOL for NP0172591 (9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol)

3D MOL for NP0172591 (9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol)

3D SDF for NP0172591 (9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol)

3D-SDF for NP0172591 (9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol)

PDB for NP0172591 (9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol)

3D PDB for NP0172591 (9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol)

SMILES for NP0172591 (9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol)

INCHI for NP0172591 (9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol)

Structure for NP0172591 (9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol)

3D Structure for NP0172591 (9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-5,7-diol)