NP-MRD: Showing NP-Card for Dihydroornativolide (NP0064059)

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Record Information

Version

2.0

Created at

2022-04-28 08:21:15 UTC

Updated at

2022-04-28 08:21:15 UTC

NP-MRD ID

NP0064059

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydroornativolide

Description

(1R,1'S,2S,3'R,4R,7R,7'R,8R,9R,11S,12R,13'R,14S)-2,7,12,13'-tetramethyl-4',5,10,14',16'-pentaoxaspiro[pentacyclo[10.2.2.0¹,¹¹.0⁴,⁸.0⁹,¹¹]Hexadecane-14,6'-tetracyclo[11.2.1.0¹,¹⁰.0³,⁷]Hexadecane]-9',15-diene-5',6-dione belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring. Dihydroornativolide is found in Geigeria ornativa. Based on a literature review very few articles have been published on (1R,1'S,2S,3'R,4R,7R,7'R,8R,9R,11S,12R,13'R,14S)-2,7,12,13'-tetramethyl-4',5,10,14',16'-pentaoxaspiro[pentacyclo[10.2.2.0¹,¹¹.0⁴,⁸.0⁹,¹¹]Hexadecane-14,6'-tetracyclo[11.2.1.0¹,¹⁰.0³,⁷]Hexadecane]-9',15-diene-5',6-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282210212D          

 37 45  0  0  1  0            999 V2000
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  1 37  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282210212D          

 37 45  0  0  1  0            999 V2000
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   -0.6720    0.2159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0364   -0.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0672    1.3997    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  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
  1 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
  8 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  6  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 21  1  6  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  6  0  0  0
 26 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  1  0  0  0
 24 35  1  6  0  0  0
 23 35  1  6  0  0  0
 19 36  1  1  0  0  0
  1 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0064059

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@H]2[C@H]3O[C@]33[C@]4(C)C[C@]5([C@H]6CC=C7CC[C@]8(C)OC[C@@]7(C[C@H]6OC5=O)O8)[C@]3(C=C4)[C@@H](C)C[C@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O7/c1-15-11-19-21(16(2)23(31)34-19)22-30(36-22)25(3)9-10-29(15,30)28(13-25)18-6-5-17-7-8-26(4)33-14-27(17,37-26)12-20(18)35-24(28)32/h5,9-10,15-16,18-22H,6-8,11-14H2,1-4H3/t15-,16+,18-,19+,20+,21+,22+,25-,26+,27+,28+,29-,30-/m0/s1

> <INCHI_KEY>
KDUACHYNPUQAPN-XWGDFHDWSA-N

> <FORMULA>
C30H36O7

> <MOLECULAR_WEIGHT>
508.611

> <EXACT_MASS>
508.246103499

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.614373013986494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,1'S,2S,3'R,4R,7R,7'R,8R,9R,11S,12R,13'R,14S)-2,7,12,13'-tetramethyl-4',5,10,14',16'-pentaoxaspiro[pentacyclo[10.2.2.0^{1,11}.0^{4,8}.0^{9,11}]hexadecane-14,6'-tetracyclo[11.2.1.0^{1,10}.0^{3,7}]hexadecane]-9',15-diene-5',6-dione

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
2.873455554333331

> <ALOGPS_LOGS>
-5.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.856610863461174

> <JCHEM_POLAR_SURFACE_AREA>
83.59

> <JCHEM_REFRACTIVITY>
131.9989

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,1'S,2S,3'R,4R,7R,7'R,8R,9R,11S,12R,13'R,14S)-2,7,12,13'-tetramethyl-4',5,10,14',16'-pentaoxaspiro[pentacyclo[10.2.2.0^{1,11}.0^{4,8}.0^{9,11}]hexadecane-14,6'-tetracyclo[11.2.1.0^{1,10}.0^{3,7}]hexadecane]-9',15-diene-5',6-dione

> <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       9.908   2.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.093   3.419   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.497   3.398   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.793   1.946   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.276   2.251   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.096   1.267   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.127  -0.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.339  -1.245   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.850  -0.866   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.623   0.522   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.716   1.317   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.995  -0.438   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.361   0.440   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.792  -2.681   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.254  -2.614   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.295  -3.819   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.843  -1.130   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.051  -1.063   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.542  -1.051   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.443  -2.234   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.873  -1.662   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.771  -0.126   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.278   0.252   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.357   1.655   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.343   3.026   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.852   3.334   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.033   2.346   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.997   0.806   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.518   0.564   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.026   4.864   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.624   5.502   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.317   7.011   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.416   4.366   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.946   4.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.254   0.403   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.935  -0.393   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.325   2.613   0.000  0.00  0.00           C+0
CONECT    1    2   11   13   37                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11   12                                             
CONECT   11   10    1                                                       
CONECT   12   10   13                                                       
CONECT   13   12    1                                                       
CONECT   14    8   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    7   18   22                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   23   36                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   23   28                                             
CONECT   23   22   19   24   35                                             
CONECT   24   23   25   35                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   22   29                                                  
CONECT   29   28                                                            
CONECT   30   26   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   25   34                                                  
CONECT   34   33                                                            
CONECT   35   24   23                                                       
CONECT   36   19                                                            
CONECT   37    1                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆O₇

Average Mass

508.6110 Da

Monoisotopic Mass

508.24610 Da

IUPAC Name

(1R,1'S,2S,3'R,4R,7R,7'R,8R,9R,11S,12R,13'R,14S)-2,7,12,13'-tetramethyl-4',5,10,14',16'-pentaoxaspiro[pentacyclo[10.2.2.0^{1,11}.0^{4,8}.0^{9,11}]hexadecane-14,6'-tetracyclo[11.2.1.0^{1,10}.0^{3,7}]hexadecane]-9',15-diene-5',6-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@H]2[C@H]3O[C@]33[C@]4(C)C[C@]5([C@H]6CC=C7CC[C@]8(C)OC[C@@]7(C[C@H]6OC5=O)O8)[C@]3(C=C4)[C@@H](C)C[C@H]2OC1=O

InChI Identifier

InChI=1S/C30H36O7/c1-15-11-19-21(16(2)23(31)34-19)22-30(36-22)25(3)9-10-29(15,30)28(13-25)18-6-5-17-7-8-26(4)33-14-27(17,37-26)12-20(18)35-24(28)32/h5,9-10,15-16,18-22H,6-8,11-14H2,1-4H3/t15-,16+,18-,19+,20+,21+,22+,25-,26+,27+,28+,29-,30-/m0/s1

InChI Key

KDUACHYNPUQAPN-XWGDFHDWSA-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
Geigeria ornativa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Sesquiterpene lactones

Alternative Parents

Substituents

Helenalin-skeleton
Germacranolide
Sesquiterpenoid
Ketal
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxane
Meta-dioxolane
Tetrahydrofuran
Carboxylic acid ester
Lactone
Acetal
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen 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	3.93	ALOGPS
logP	2.87	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	83.59 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	132 m³·mol⁻¹	ChemAxon
Polarizability	54.61 Å³	ChemAxon
Number of Rings	9	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

162881564

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dihydroornativolide (NP0064059)

MOL for NP0064059 (Dihydroornativolide)

3D MOL for NP0064059 (Dihydroornativolide)

3D SDF for NP0064059 (Dihydroornativolide)

3D-SDF for NP0064059 (Dihydroornativolide)

PDB for NP0064059 (Dihydroornativolide)

3D PDB for NP0064059 (Dihydroornativolide)

SMILES for NP0064059 (Dihydroornativolide)

INCHI for NP0064059 (Dihydroornativolide)

Structure for NP0064059 (Dihydroornativolide)

3D Structure for NP0064059 (Dihydroornativolide)