NP-MRD: Showing NP-Card for 3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0287995)

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Record Information

Version

2.0

Created at

2022-09-09 17:30:48 UTC

Updated at

2022-09-09 17:30:49 UTC

NP-MRD ID

NP0287995

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

Description

3Beta-Tirucalla-7,24-dien-3-ol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3Beta-Tirucalla-7,24-dien-3-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3beta-tirucalla-7,24-dien-3-ol is found, on average, in the highest concentration in tea. 3Beta-tirucalla-7,24-dien-3-ol has also been detected, but not quantified in, shea tree and soy beans. 3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol is found in Arabidopsis thaliana, Camellia sinensis, Euphorbia guyoniana, Euphorbia kansui, Euphorbia oxyphylla, Euphorbia plumerioides, Euphorbia rigida, Euphorbia tithymaloides, Ixeris chinensis, Maclura pomifera, Picris hieracioides, Tovomita brasiliensis and Tripetalum cymosum. This could make 3beta-tirucalla-7,24-dien-3-ol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241210482D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241210482D          

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  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 24  1  0  0  0  0
  6  7  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 22  1  0  0  0  0
  9 28  1  0  0  0  0
 10 11  2  0  0  0  0
 10 19  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 14 29  1  0  0  0  0
 14 30  1  0  0  0  0
 15 16  1  0  0  0  0
 15 31  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 27  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)C)C1CCC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,12,21-23,25-26,31H,9,11,13-19H2,1-8H3

> <INCHI_KEY>
DICCPNLDOZNSML-UHFFFAOYSA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.7174

> <EXACT_MASS>
426.386166222

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
54.06877193558148

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

> <ALOGPS_LOGP>
7.98

> <JCHEM_LOGP>
7.750330345666665

> <ALOGPS_LOGS>
-6.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.554178983383924

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8068021126678707

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
134.8113

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.13e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-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       6.822  -1.609   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.749  -2.835   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.215  -2.376   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.296  -3.602   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.763  -3.296   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.149  -1.916   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.222  -0.689   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.302   0.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.231   0.230   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.609   0.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.609   2.376   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.990   3.143   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.369   2.376   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.595   3.296   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.976   2.682   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.129   1.150   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.749   0.382   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.369   0.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.990   0.230   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.835  -1.303   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.609  -2.069   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.231  -1.303   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.537  -2.989   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.996  -4.675   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.356  -1.916   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.362  -0.228   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.829  -0.689   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.383   1.609   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.515   4.675   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.676   4.675   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -8.356   3.296   0.000  0.00  0.00           O+0
CONECT    1    2   25   26                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   22   28                                             
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   29   30                                             
CONECT   15   14   16   31                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   13   17   19   27                                             
CONECT   19   10   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22    6    9   21   23                                             
CONECT   23   22                                                            
CONECT   24    5                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27   18                                                            
CONECT   28    9                                                            
CONECT   29   14                                                            
CONECT   30   14                                                            
CONECT   31   15                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
3b-Tirucalla-7,24-dien-3-ol	Generator
3Β-tirucalla-7,24-dien-3-ol	Generator

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7174 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

2,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

Traditional Name

2,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

CAS Registry Number

Not Available

SMILES

CC(CCC=C(C)C)C1CCC2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3CCC12C

InChI Identifier

InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,12,21-23,25-26,31H,9,11,13-19H2,1-8H3

InChI Key

DICCPNLDOZNSML-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
Arabidopsis thaliana	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Euphorbia guyoniana	LOTUS Database	35616633
Euphorbia kansui	LOTUS Database	35616633
Euphorbia oxyphylla	LOTUS Database	35616633
Euphorbia plumerioides	LOTUS Database	35616633
Euphorbia rigida	LOTUS Database	35616633
Euphorbia tithymaloides	LOTUS Database	35616633
Ixeris chinensis	LOTUS Database	35616633
Maclura pomifera	LOTUS Database	35616633
Picris hieracioides	LOTUS Database	35616633
Tovomita brasiliensis	LOTUS Database	35616633
Tripetalum cymosum	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
Cholesterol
Cholesterol-skeleton
Cholestane-skeleton
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Steroid
Delta-7-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a triterpenoid (CPD-13279 )

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	7.98	ALOGPS
logP	7.75	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	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	4	ChemAxon
Refractivity	134.81 m³·mol⁻¹	ChemAxon
Polarizability	54.07 Å³	ChemAxon
Number of Rings	4	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

HMDB0034929

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013519

KNApSAcK ID

C00011163

Chemspider ID

26516397

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12302181

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0287995)

MOL for NP0287995 (3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D MOL for NP0287995 (3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D SDF for NP0287995 (3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D-SDF for NP0287995 (3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

PDB for NP0287995 (3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D PDB for NP0287995 (3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

SMILES for NP0287995 (3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

INCHI for NP0287995 (3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

Structure for NP0287995 (3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D Structure for NP0287995 (3a,6,6,9a,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)