NP-MRD: Showing NP-Card for 7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol (NP0151784)

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Record Information

Version

2.0

Created at

2022-09-02 08:09:18 UTC

Updated at

2022-09-02 08:09:18 UTC

NP-MRD ID

NP0151784

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol

Description

Dimoracin, also known as chimassorb 944 or sanol LS 944, belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Dimoracin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Dimoracin has been detected, but not quantified in, fruits. 7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol is found in Cordyline stricta. This could make dimoracin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241214412D          

 31 36  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 02241214412D          

 31 36  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0151784

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3C4CCC5CC(O)CC(O)C5(C)C4CCC23C)OC11CCC(=C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h16-24,28-29H,1,5-14H2,2-4H3

> <INCHI_KEY>
XLHFBXMTUNORSV-UHFFFAOYSA-N

> <FORMULA>
C27H42O4

> <MOLECULAR_WEIGHT>
430.62

> <EXACT_MASS>
430.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
50.28688885912523

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
3.7595877813333334

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.374421973880075

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.504215441737195

> <JCHEM_PKA_STRONGEST_BASIC>
-2.725746678503633

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
120.58829999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol

> <JCHEM_VEBER_RULE>
0

$$$$

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      -4.850   5.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.463   4.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.540   5.542   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.850   0.462   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.617  -0.462   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.850  -5.388   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.617  -4.465   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.078   3.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.309   2.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.696   2.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.081   2.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.081   4.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -7.466   5.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.924   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.539   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.385   1.539   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.693   2.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.232   1.693   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.232   0.154   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.847  -0.616   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.693  -2.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.693  -2.463   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.462  -1.231   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.001  -1.539   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.079  -0.462   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.466  -5.542   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.235  -4.773   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.235  -3.232   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.850  -2.617   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.309  -3.078   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.924  -3.540   0.000  0.00  0.00           O+0
CONECT    1    2   12                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2                                                            
CONECT    4    5   10                                                       
CONECT    5    4   19                                                       
CONECT    6    7   27                                                       
CONECT    7    6   30                                                       
CONECT    8    9                                                            
CONECT    9    2    8   10   18                                             
CONECT   10    4    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12    1   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15   14   16   20   23                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18    9   17   19                                                  
CONECT   19    5   18   20                                                  
CONECT   20   15   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   15   22   24                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24                                                            
CONECT   26   27                                                            
CONECT   27    6   26   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30    7   24   29   31                                             
CONECT   31   22   30                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Value	Source
Chimassorb 944	HMDB
Chimassorb 944fd	HMDB
Chimassorb 944FL	HMDB
Chimassorb 944ld	HMDB
Chimassorb 994ld	HMDB
Chimassorb LS 944ld	HMDB
Hals 3	HMDB
Sanduvor 3944	HMDB
Sanol 944	HMDB
Sanol LS 944	HMDB
Sanol LS 944ld	HMDB

Chemical Formula

C₂₇H₄₂O₄

Average Mass

430.6200 Da

Monoisotopic Mass

430.30831 Da

IUPAC Name

7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol

Traditional Name

7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3C4CCC5CC(O)CC(O)C5(C)C4CCC23C)OC11CCC(=C)CO1

InChI Identifier

InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h16-24,28-29H,1,5-14H2,2-4H3

InChI Key

XLHFBXMTUNORSV-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
Cordyline stricta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
4'-prenylated 2-arybenzofuran
3-prenylated flavan
5-hydroxyflavonoid
Hydroxyflavonoid
Flavan
2-phenylbenzofuran
Phenylbenzofuran
Chromane
Benzopyran
1-benzopyran
Benzofuran
Resorcinol
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.63	ALOGPS
logP	3.76	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.5	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	120.59 m³·mol⁻¹	ChemAxon
Polarizability	50.29 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030068

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001378

KNApSAcK ID

Not Available

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

131750953

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol (NP0151784)

MOL for NP0151784 (7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol)

3D MOL for NP0151784 (7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol)

3D SDF for NP0151784 (7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol)

3D-SDF for NP0151784 (7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol)

PDB for NP0151784 (7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol)

3D PDB for NP0151784 (7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol)

SMILES for NP0151784 (7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol)

INCHI for NP0151784 (7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol)

Structure for NP0151784 (7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol)

3D Structure for NP0151784 (7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-14',16'-diol)