NP-MRD: Showing NP-Card for 5a-(hydroxymethyl)-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol (NP0202540)

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Record Information

Version

2.0

Created at

2022-09-04 21:46:21 UTC

Updated at

2022-09-04 21:46:21 UTC

NP-MRD ID

NP0202540

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Dehydrocyanaropicrin belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Dehydrocyanaropicrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Dehydrocyanaropicrin has been detected, but not quantified in, globe artichokes and root vegetables. 5a-(hydroxymethyl)-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol is found in Bersama swinnyi and Diospyros malabarica. This could make dehydrocyanaropicrin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308122D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 05061308122D          

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 21  8  1  0  0  0  0
 22 11  1  0  0  0  0
 23  9  1  0  0  0  0
 24 12  1  0  0  0  0
 25 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 22  1  0  0  0  0
 26 24  1  0  0  0  0
 27  5  1  0  0  0  0
 27 13  1  0  0  0  0
 27 16  1  0  0  0  0
 27 25  1  0  0  0  0
 28  6  1  0  0  0  0
 28 14  1  0  0  0  0
 28 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29  7  1  0  0  0  0
 29 15  1  0  0  0  0
 29 23  1  0  0  0  0
 30 17  1  0  0  0  0
 30 18  1  0  0  0  0
 30 21  1  0  0  0  0
 30 29  1  0  0  0  0
 31 18  1  0  0  0  0
 32 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202540

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1CCC2(C)CCC3(CO)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O2/c1-19(2)20-10-13-27(5)16-17-30(18-31)21(25(20)27)8-9-23-28(6)14-12-24(32)26(3,4)22(28)11-15-29(23,30)7/h20-25,31-32H,1,8-18H2,2-7H3

> <INCHI_KEY>
XHOGEOQSRLNKKB-UHFFFAOYSA-N

> <FORMULA>
C30H50O2

> <MOLECULAR_WEIGHT>
442.7168

> <EXACT_MASS>
442.381080844

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
54.593083489460085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxymethyl)-1,5,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol

> <ALOGPS_LOGP>
5.30

> <JCHEM_LOGP>
6.167275324333334

> <ALOGPS_LOGS>
-6.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.660972720626912

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.4894333901713

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4949578422018014

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
132.68299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.83e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(hydroxymethyl)-1,5,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol

> <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      -0.357   6.669   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.244   6.075   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.329   0.949   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.600  -0.015   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.273   0.406   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.851   4.212   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.409   0.034   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.772   4.258   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.312   4.235   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.987   3.515   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.560   0.199   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.931   4.165   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.850   1.981   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.391   4.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.021   0.223   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.401   0.293   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.941   0.270   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.481   0.246   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.772   5.621   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.429   4.120   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.981   2.936   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.351   1.521   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.061   2.890   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.681   2.819   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.442   2.960   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.890   1.498   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.651   1.638   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.601   2.866   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.271   1.568   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.731   1.591   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.691  -1.076   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      12.221   2.796   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   19                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7   29                                                            
CONECT    8    9   21                                                       
CONECT    9    8   23                                                       
CONECT   10   13   20                                                       
CONECT   11   15   22                                                       
CONECT   12   14   24                                                       
CONECT   13   10   27                                                       
CONECT   14   12   28                                                       
CONECT   15   11   29                                                       
CONECT   16   17   27                                                       
CONECT   17   16   30                                                       
CONECT   18   30   31                                                       
CONECT   19    1    2   20                                                  
CONECT   20   10   19   25                                                  
CONECT   21    8   25   30                                                  
CONECT   22   11   26   28                                                  
CONECT   23    9   28   29                                                  
CONECT   24   12   26   32                                                  
CONECT   25   20   21   27                                                  
CONECT   26    3    4   22   24                                             
CONECT   27    5   13   16   25                                             
CONECT   28    6   14   22   23                                             
CONECT   29    7   15   23   30                                             
CONECT   30   17   18   21   29                                             
CONECT   31   18                                                            
CONECT   32   24                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
3b-20(29)-Lupene-3,27-diol	Generator
3Β-20(29)-lupene-3,27-diol	Generator

Chemical Formula

C₃₀H₅₀O₂

Average Mass

442.7168 Da

Monoisotopic Mass

442.38108 Da

IUPAC Name

2-(hydroxymethyl)-1,5,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol

Traditional Name

2-(hydroxymethyl)-1,5,14,18,18-pentamethyl-8-(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)CCC3(CO)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C12

InChI Identifier

InChI=1S/C30H50O2/c1-19(2)20-10-13-27(5)16-17-30(18-31)21(25(20)27)8-9-23-28(6)14-12-24(32)26(3,4)22(28)11-15-29(23,30)7/h20-25,31-32H,1,8-18H2,2-7H3

InChI Key

XHOGEOQSRLNKKB-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
Bersama swinnyi	LOTUS Database	35616633
Diospyros malabarica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	5.3	ALOGPS
logP	6.17	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	19.49	ChemAxon
pKa (Strongest Basic)	-0.49	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	2	ChemAxon
Refractivity	132.68 m³·mol⁻¹	ChemAxon
Polarizability	54.59 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

HMDB0035029

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013635

KNApSAcK ID

C00020513

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

71437252

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5a-(hydroxymethyl)-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol (NP0202540)

MOL for NP0202540 (5a-(hydroxymethyl)-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D MOL for NP0202540 (5a-(hydroxymethyl)-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D SDF for NP0202540 (5a-(hydroxymethyl)-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D-SDF for NP0202540 (5a-(hydroxymethyl)-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

PDB for NP0202540 (5a-(hydroxymethyl)-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D PDB for NP0202540 (5a-(hydroxymethyl)-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

SMILES for NP0202540 (5a-(hydroxymethyl)-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

INCHI for NP0202540 (5a-(hydroxymethyl)-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

Structure for NP0202540 (5a-(hydroxymethyl)-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)

3D Structure for NP0202540 (5a-(hydroxymethyl)-3a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol)