NP-MRD: Showing NP-Card for dammaradienol (NP0197150)

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Record Information

Version

2.0

Created at

2022-09-04 15:21:26 UTC

Updated at

2022-09-04 15:21:26 UTC

NP-MRD ID

NP0197150

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dammaradienol

Description

Dammaradienol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. dammaradienol is found in Artemisia xerophytica, Bejaranoa semistriata, Bryonia dioica, Camellia japonica, Camellia oleifera, Camellia sasanqua, Chrysanthemum morifolium, Duhaldea cappa, Euphorbia kansui, Euphorbia segetalis, Helianthus annuus, Ixeridium gracile, Ixeris chinensis, Lasiolaena morii, Mangifera indica, Olea capensis, Olea europaea, Olearia pimeleoides, Pisum sativum, Dysoxylum hongkongense, Santolina oblongifolia, Santolina rosmarinifolia, Tripetalum cymosum and Vismia laurentii. dammaradienol was first documented in 2007 (PMID: 17479428). Based on a literature review a small amount of articles have been published on Dammaradienol (PMID: 32671418) (PMID: 27379760) (PMID: 20513968).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217212D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042217212D          

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 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 17 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0197150

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(=C)[C@H]1CC[C@]2(C)[C@@H]1CC[C@@H]1[C@@]3(C)CC[C@H](O)C(C)(C)[C@@H]3CC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-29(7)23(22)12-13-25-28(6)17-16-26(31)27(4,5)24(28)15-19-30(25,29)8/h10,22-26,31H,3,9,11-19H2,1-2,4-8H3/t22-,23-,24+,25-,26+,28+,29-,30-/m1/s1

> <INCHI_KEY>
WZAMDSBJONFHAO-WJQSYXMBSA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.729

> <EXACT_MASS>
426.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.939317535620404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,7R,10R,11R,14S,15R)-2,6,6,10,11-pentamethyl-14-(6-methylhepta-1,5-dien-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

> <JCHEM_LOGP>
7.808264016000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.489433390177716

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351218351362667

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
133.7388

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,7R,10R,11R,14S,15R)-2,6,6,10,11-pentamethyl-14-(6-methylhepta-1,5-dien-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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       1.362  -2.246   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.781  -3.673   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.744  -3.883   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.690  -2.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.215  -2.878   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.160  -1.662   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.686  -1.873   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.580  -0.236   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.158  -7.782   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.290  -4.203   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.184  -8.144   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.322  -8.817   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.724  -7.984   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   30                                             
CONECT   13   12                                                            
CONECT   14   12    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   19   20   27                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   18   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   17   12   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7290 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

(1R,2R,5S,7R,10R,11R,14S,15R)-2,6,6,10,11-pentamethyl-14-(6-methylhepta-1,5-dien-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

Traditional Name

(1R,2R,5S,7R,10R,11R,14S,15R)-2,6,6,10,11-pentamethyl-14-(6-methylhepta-1,5-dien-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(=C)[C@H]1CC[C@]2(C)[C@@H]1CC[C@@H]1[C@@]3(C)CC[C@H](O)C(C)(C)[C@@H]3CC[C@@]21C

InChI Identifier

InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-29(7)23(22)12-13-25-28(6)17-16-26(31)27(4,5)24(28)15-19-30(25,29)8/h10,22-26,31H,3,9,11-19H2,1-2,4-8H3/t22-,23-,24+,25-,26+,28+,29-,30-/m1/s1

InChI Key

WZAMDSBJONFHAO-WJQSYXMBSA-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
Artemisia xerophytica	LOTUS Database	35616633
Bejaranoa semistriata	LOTUS Database	35616633
Bryonia dioica	LOTUS Database	35616633
Camellia japonica	LOTUS Database	35616633
Camellia oleifera	LOTUS Database	35616633
Camellia sasanqua	LOTUS Database	35616633
Chrysanthemum morifolium	LOTUS Database	35616633
Duhaldea cappa	LOTUS Database	35616633
Euphorbia kansui	LOTUS Database	35616633
Euphorbia segetalis	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Ixeridium gracile	LOTUS Database	35616633
Ixeris chinensis	LOTUS Database	35616633
Lasiolaena morii	LOTUS Database	35616633
Mangifera indica	LOTUS Database	35616633
Olea capensis	LOTUS Database	35616633
Olea europaea	LOTUS Database	35616633
Olearia pimeleoides	LOTUS Database	35616633
Pisum sativum	LOTUS Database	35616633
Prasoxylon hongkongense	LOTUS Database	35616633
Santolina oblongifolia	LOTUS Database	35616633
Santolina rosmarinifolia	LOTUS Database	35616633
Tripetalum cymosum	LOTUS Database	35616633
Vismia laurentii	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
14-alpha-methylsteroid
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
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	7.81	ChemAxon
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	4	ChemAxon
Refractivity	133.74 m³·mol⁻¹	ChemAxon
Polarizability	54.94 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00042449

Chemspider ID

20119990

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13893946

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bouslama L, Benzekri R, Nsaibia S, Papetti A, Limam F: Identification of an antiviral compound isolated from Pistacia lentiscus. Arch Microbiol. 2020 Nov;202(9):2569-2578. doi: 10.1007/s00203-020-01980-2. Epub 2020 Jul 15. [PubMed:32671418 ]
Giongo AM, Vendramim JD, Freitas SD, Silva MF: Toxicity of Secondary Metabolites from Meliaceae Against Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae). Neotrop Entomol. 2016 Dec;45(6):725-733. doi: 10.1007/s13744-016-0418-6. Epub 2016 Jul 5. [PubMed:27379760 ]
Akihisa T, Kojima N, Katoh N, Ichimura Y, Suzuki H, Fukatsu M, Maranz S, Masters ET: Triterpene alcohol and fatty acid composition of shea nuts from seven African countries. J Oleo Sci. 2010;59(7):351-60. doi: 10.5650/jos.59.351. [PubMed:20513968 ]
Shen CC, Tsai SY, Wei SL, Wang ST, Shieh BJ, Chen CC: Flavonoids isolated from Draconis Resina. Nat Prod Res. 2007 Apr;21(4):377-80. doi: 10.1080/14786410701194575. [PubMed:17479428 ]
LOTUS database [Link]

Showing NP-Card for dammaradienol (NP0197150)

MOL for NP0197150 (dammaradienol)

3D MOL for NP0197150 (dammaradienol)

3D SDF for NP0197150 (dammaradienol)

3D-SDF for NP0197150 (dammaradienol)

PDB for NP0197150 (dammaradienol)

3D PDB for NP0197150 (dammaradienol)

SMILES for NP0197150 (dammaradienol)

INCHI for NP0197150 (dammaradienol)

Structure for NP0197150 (dammaradienol)

3D Structure for NP0197150 (dammaradienol)