NP-MRD: Showing NP-Card for Valerenal (NP0064337)

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Record Information

Version

2.0

Created at

2022-04-28 08:35:29 UTC

Updated at

2022-04-28 08:35:29 UTC

NP-MRD ID

NP0064337

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Valerenal

Description

Valerenal belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, valerenal is considered to be an isoprenoid. Valerenal is found in Cymbopogon flexuosus, Rhododendron tomentosum, Nardostachys jatamansi and Valeriana officinalis . Valerenal was first documented in 2010 (PMID: 21104529). Based on a literature review a small amount of articles have been published on Valerenal (PMID: 35199395) (PMID: 31108854) (PMID: 26920719) (PMID: 24427929).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.9967    1.8027   -1.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2274    1.3065   -1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3140    0.3320   -0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835   -0.5386    0.3326 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5951    0.2736    1.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8843    0.4353    1.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5119   -0.1823   -0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825    1.2387    1.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9136    1.4270    1.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1930   -1.7071    1.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0849   -2.1782    0.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1262   -1.1506    0.6384 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4693   -1.4664    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7128    0.2151    0.1908 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4604    0.6642   -1.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5972    1.8955   -1.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7961    2.7040   -2.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4504    1.0350   -2.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7864    2.0943   -1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3890   -0.9425   -0.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1092    0.7306    2.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002    0.2334   -1.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573   -1.2944   -0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6338   -0.0948    0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2268    1.7031    2.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1176   -1.4701    2.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8707   -2.5968    1.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4046   -3.1437    0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9132   -2.2677   -0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900   -1.1534    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4356   -1.5739   -1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1491   -0.6177    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189   -2.3859    0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9484    0.9995    0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3122   -0.0733   -1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4963    0.9424   -0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6804    2.0743   -2.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220    2.7303   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 16  1  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 14  3  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 12 30  1  1
 11 28  1  0
 11 29  1  0
 10 26  1  0
 10 27  1  0
  4 20  1  6
  5 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
 16 37  1  0
 16 38  1  0
 15 35  1  0
 15 36  1  0
 14 34  1  1
M  END


  Mrv1652304282210352D          

 16 17  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  6  9  1  0  0  0  0
  5 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 16  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0064337

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@H](\C=C(/C)C=O)C2=C(C)CC[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-10(9-16)8-13-6-4-11(2)14-7-5-12(3)15(13)14/h8-9,11,13-14H,4-7H2,1-3H3/b10-8+/t11-,13+,14-/m1/s1

> <INCHI_KEY>
RJZWGDPBGWGJNU-MTXIQXFFSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.34

> <EXACT_MASS>
218.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
25.934877767781405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enal

> <ALOGPS_LOGP>
4.28

> <JCHEM_LOGP>
3.4377662196666665

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.44602561182563

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
69.1236

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
valerenal

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.591   9.003   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.924  -0.237   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    4                                                       
CONECT    9    6                                                            
CONECT   10    5    1   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16    3                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O

Average Mass

218.3400 Da

Monoisotopic Mass

218.16707 Da

IUPAC Name

(2E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enal

Traditional Name

valerenal

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@H](\C=C(/C)C=O)C2=C(C)CC[C@H]12

InChI Identifier

InChI=1S/C15H22O/c1-10(9-16)8-13-6-4-11(2)14-7-5-12(3)15(13)14/h8-9,11,13-14H,4-7H2,1-3H3/b10-8+/t11-,13+,14-/m1/s1

InChI Key

RJZWGDPBGWGJNU-MTXIQXFFSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cymbopogon flexuosus	LOTUS Database	35616633
Ledum palustre	LOTUS Database	35616633
Nardostachys jatamansi	LOTUS Database	35616633
Valeriana officinalis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Cyclobutane and cyclopentane sesquiterpenoids (LMPR0103040001 )

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	4.28	ALOGPS
logP	3.44	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.12 m³·mol⁻¹	ChemAxon
Polarizability	25.93 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00021295

Chemspider ID

4945178

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440942

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nagpal K, Garg M, Arora D, Dubey A, Grewal AS: An extensive review on phytochemistry and pharmacological activities of Indian medicinal plant Celastrus paniculatus Willd. Phytother Res. 2022 May;36(5):1930-1951. doi: 10.1002/ptr.7424. Epub 2022 Feb 23. [PubMed:35199395 ]
David A, Wang F, Sun X, Li H, Lin J, Li P, Deng G: Chemical Composition, Antioxidant, and Antimicrobial Activities of Vetiveria zizanioides (L.) Nash Essential Oil Extracted by Carbon Dioxide Expanded Ethanol. Molecules. 2019 May 17;24(10). pii: molecules24101897. doi: 10.3390/molecules24101897. [PubMed:31108854 ]
Ricigliano V, Kumar S, Kinison S, Brooks C, Nybo SE, Chappell J, Howarth DG: Regulation of sesquiterpenoid metabolism in recombinant and elicited Valeriana officinalis hairy roots. Phytochemistry. 2016 May;125:43-53. doi: 10.1016/j.phytochem.2016.02.011. Epub 2016 Feb 23. [PubMed:26920719 ]
Kadam SH, Paknikar SK, Rao GV: Revised structures of nardal and nardin: identity with valerenal and valerenic acid. Nat Prod Commun. 2013 Nov;8(11):1513-4. [PubMed:24427929 ]
Samaneh ET, Tayebeh R, Hassan E, Vahid N: Composition of essential oils in subterranean organs of three species of Valeriana L. Nat Prod Res. 2010 Nov;24(19):1834-42. doi: 10.1080/14786419.2010.482051. [PubMed:21104529 ]

Showing NP-Card for Valerenal (NP0064337)

MOL for NP0064337 (Valerenal)

3D MOL for NP0064337 (Valerenal)

3D SDF for NP0064337 (Valerenal)

3D-SDF for NP0064337 (Valerenal)

PDB for NP0064337 (Valerenal)

3D PDB for NP0064337 (Valerenal)

SMILES for NP0064337 (Valerenal)

INCHI for NP0064337 (Valerenal)

Structure for NP0064337 (Valerenal)

3D Structure for NP0064337 (Valerenal)