NP-MRD: Showing NP-Card for trans,trans-Xanthoxin (NP0075845)

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Record Information

Version

2.0

Created at

2022-04-28 21:04:05 UTC

Updated at

2022-04-28 21:04:05 UTC

NP-MRD ID

NP0075845

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trans,trans-Xanthoxin

Description

2-Trans,4-trans-xanthoxin, also known as (e,e)-xanthoxin, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. trans,trans-Xanthoxin is found in Codium latum, Pueraia thunbergiana, Pueraria montana and Zea mays. trans,trans-Xanthoxin was first documented in 2002 (PMID: 12172025). Based on a literature review very few articles have been published on 2-trans,4-trans-xanthoxin (PMID: 12809718).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -2.9227    2.3591   -0.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461    1.1575    0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5456    0.6420    0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8161   -0.4032    0.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -0.9481    0.0839 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4757   -2.4181    0.0167 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107   -1.5881   -1.1053 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6739   -1.8665   -2.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7778   -1.3834   -1.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0272   -1.3408   -1.0821 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8638   -0.2953   -1.5159 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8528   -1.2447    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6552   -0.4298    0.7220 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4505   -0.5681    2.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838    1.0393    0.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6658    1.6353    1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6691    2.6055    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8865    3.4378    0.3131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7258    3.2111    0.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1103    1.9807   -1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8298    1.9002   -0.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0552    0.9037   -0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2139   -0.7455    1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5565   -1.9695   -1.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788   -2.8501   -2.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817   -1.0399   -2.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6675   -0.4430   -2.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8401   -2.1965   -2.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6384   -2.2730   -1.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2027    0.2570   -0.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6676   -2.2721    0.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7299   -0.8020    0.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7106   -1.3841    2.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0952    0.3777    2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804   -0.8995    2.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9054    1.5323    0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7428    1.4523    0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6253    1.1774   -0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556    1.0079    2.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4409    2.6845    2.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  4  1  6
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
  2 16  2  0
 16 17  1  0
 17 18  2  0
  7  5  1  0
 13  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
M  END


  Mrv1652304282223042D          

 18 19  0  0  1  0            999 V2000
    0.4763   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4763   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9053   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5781   -1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8035   -1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7612   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1737   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4112   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7612   -2.9684    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  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  1  0  0  0
  2 10  1  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  1  0  0  0
  1 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 14 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075845

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C)=C/C=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-11(6-8-16)5-7-15-13(2,3)9-12(17)10-14(15,4)18-15/h5-8,12,17H,9-10H2,1-4H3/b7-5+,11-6+/t12-,14+,15-/m0/s1

> <INCHI_KEY>
ZTALKMXOHWQNIA-LVMPZUNDSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.338

> <EXACT_MASS>
250.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.19374324404533

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E)-5-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3-methylpenta-2,4-dienal

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
1.6246488456666666

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.13968403410598

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7377022034820433

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
72.3038

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E)-5-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3-methylpenta-2,4-dienal

> <JCHEM_VEBER_RULE>
0

$$$$

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       0.889  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.889  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.223   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.556  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.556  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.223  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.946  -3.670   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.500  -3.670   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.890   0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.445  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.119   1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.119  -2.874   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.421  -2.874   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.191  -4.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.731  -4.207   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.501  -5.541   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.731  -6.875   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.421  -5.541   0.000  0.00  0.00           C+0
CONECT    1    2    6   10   12                                             
CONECT    2    1    3   10   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4                                                            
CONECT   10    2    1                                                       
CONECT   11    2                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
(e,e)-Xanthoxin	ChEBI
2E,4E-Xanthoxin	ChEBI
trans,trans-Xanthoxin	ChEBI
Xanthoxin, (1S-(1alpha(2E,4E),4alpha,6alpha))-isomer	MeSH
Xanthoxin, (1R-(1alpha(2E,4E),4beta,6alpha))-isomer	MeSH
Xanthoxin, (1S-(1alpha(2Z,4E),4alpha,6alpha))-isomer	MeSH
cis,trans-Xanthoxin	MeSH
Xanthoxin	MeSH
trans,trans-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'- trimethyl-1'-cyclohexyl)-3-methylpentadienal	MeSH

Chemical Formula

C₁₅H₂₂O₃

Average Mass

250.3380 Da

Monoisotopic Mass

250.15689 Da

IUPAC Name

(2E,4E)-5-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3-methylpenta-2,4-dienal

Traditional Name

(2E,4E)-5-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3-methylpenta-2,4-dienal

CAS Registry Number

Not Available

SMILES

C\C(\C=C\[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C)=C/C=O

InChI Identifier

InChI=1S/C15H22O3/c1-11(6-8-16)5-7-15-13(2,3)9-12(17)10-14(15,4)18-15/h5-8,12,17H,9-10H2,1-4H3/b7-5+,11-6+/t12-,14+,15-/m0/s1

InChI Key

ZTALKMXOHWQNIA-LVMPZUNDSA-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
Codium latum	LOTUS Database	35616633
Pueraia thunbergiana	-	KNApSAcK
Pueraria montana	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633

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

Cyclofarsesane sesquiterpenoid
Sesquiterpenoid
Oxepane
Alpha,beta-unsaturated aldehyde
Cyclic alcohol
Enal
Secondary alcohol
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxide
Aldehyde
Organooxygen compound
Organic oxygen compound
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	2.56	ALOGPS
logP	1.62	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	15.14	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.3 m³·mol⁻¹	ChemAxon
Polarizability	28.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

C00037925

Chemspider ID

5004934

KEGG Compound ID

Not Available

BioCyc ID

CPD-14384

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6504642

PDB ID

Not Available

ChEBI ID

91126

Good Scents ID

Not Available

References

General References

Gonzalez-Guzman M, Apostolova N, Belles JM, Barrero JM, Piqueras P, Ponce MR, Micol JL, Serrano R, Rodriguez PL: The short-chain alcohol dehydrogenase ABA2 catalyzes the conversion of xanthoxin to abscisic aldehyde. Plant Cell. 2002 Aug;14(8):1833-46. doi: 10.1105/tpc.002477. [PubMed:12172025 ]
Kato-Noguchi H: Allelopathic substances in Pueraria thunbergiana. Phytochemistry. 2003 Jul;63(5):577-80. doi: 10.1016/s0031-9422(03)00195-x. [PubMed:12809718 ]

Showing NP-Card for trans,trans-Xanthoxin (NP0075845)

MOL for NP0075845 (trans,trans-Xanthoxin)

3D MOL for NP0075845 (trans,trans-Xanthoxin)

3D SDF for NP0075845 (trans,trans-Xanthoxin)

3D-SDF for NP0075845 (trans,trans-Xanthoxin)

PDB for NP0075845 (trans,trans-Xanthoxin)

3D PDB for NP0075845 (trans,trans-Xanthoxin)

SMILES for NP0075845 (trans,trans-Xanthoxin)

INCHI for NP0075845 (trans,trans-Xanthoxin)

Structure for NP0075845 (trans,trans-Xanthoxin)

3D Structure for NP0075845 (trans,trans-Xanthoxin)