NP-MRD: Showing NP-Card for 21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione (NP0256837)

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Record Information

Version

2.0

Created at

2022-09-07 21:47:38 UTC

Updated at

2022-09-07 21:47:38 UTC

NP-MRD ID

NP0256837

Secondary Accession Numbers

None

Natural Product Identification

Common Name

21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione

Description

21'-(Hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]Tetracosane]-5'(13'),10',18'-triene-12',23'-dione belongs to the class of organic compounds known as illudanes and illudins. These are sesquiterpenoids containing either the illudane moiety (based on a 3,6,6,7b-tetramethyl-decahydro-1H-cyclobuta[e]indene ring system), the illudin moiety (2',2',4',6'-tetramethyl-octahydrospiro[cyclopropane-1,5'-indene]), or a derivative thereof. 21'-(Hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]Tetracosane]-5'(13'),10',18'-triene-12',23'-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191517082D          

 35 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004191517082D          

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  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  0  0  0  0
 12 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 28 31  1  0  0  0  0
 10 31  1  0  0  0  0
 31 32  2  0  0  0  0
 28 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256837

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2CC(C)(CO)CC22OC3OC4(C)C5CC(C)(C)C=C5C(=O)C5=C4C3C(CC5)(C2=O)C11CC1

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O5/c1-15-18-12-26(4,14-31)13-30(18)24(33)29(28(15)8-9-28)7-6-16-20-21(29)23(35-30)34-27(20,5)19-11-25(2,3)10-17(19)22(16)32/h10,19,21,23,31H,6-9,11-14H2,1-5H3

> <INCHI_KEY>
AHANYUXVBOKBMV-UHFFFAOYSA-N

> <FORMULA>
C30H36O5

> <MOLECULAR_WEIGHT>
476.613

> <EXACT_MASS>
476.256274259

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.59657909452858

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
3.8200921326666655

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.101924865669226

> <JCHEM_PKA_STRONGEST_BASIC>
-2.75421806375628

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
131.93449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       2.681  -7.484   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.806  -6.432   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.496  -4.841   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.099  -4.084   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.343  -2.566   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.805  -2.476   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.278  -1.027   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.578  -0.201   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.874  -2.345   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.671  -3.731   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.877  -2.655   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.422  -2.990   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.806  -2.283   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.955  -3.359   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.532  -1.931   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.512  -3.383   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.536  -2.233   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.946  -2.852   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.415  -1.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.454  -3.165   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.793  -4.385   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.288  -4.713   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.493  -6.069   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.285  -7.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.918  -6.131   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.234  -4.742   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.722  -4.564   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.643  -5.795   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.399  -7.213   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.957  -7.380   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.664  -4.806   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.551  -5.870   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.353  -6.843   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.343  -8.023   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.826  -8.290   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7    9                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9    3   11   31                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16   26                                             
CONECT   15   14                                                            
CONECT   16   14   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   16   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   14   27                                                  
CONECT   27   26   12   28                                                  
CONECT   28   27   29   31   33                                             
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   28   10   32                                                  
CONECT   32   31                                                            
CONECT   33   28    2   34   35                                             
CONECT   34   33   35                                                       
CONECT   35   34   33                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆O₅

Average Mass

476.6130 Da

Monoisotopic Mass

476.25627 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1=C2CC(C)(CO)CC22OC3OC4(C)C5CC(C)(C)C=C5C(=O)C5=C4C3C(CC5)(C2=O)C11CC1

InChI Identifier

InChI=1S/C30H36O5/c1-15-18-12-26(4,14-31)13-30(18)24(33)29(28(15)8-9-28)7-6-16-20-21(29)23(35-30)34-27(20,5)19-11-25(2,3)10-17(19)22(16)32/h10,19,21,23,31H,6-9,11-14H2,1-5H3

InChI Key

AHANYUXVBOKBMV-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as illudanes and illudins. These are sesquiterpenoids containing either the illudane moiety (based on a 3,6,6,7b-tetramethyl-decahydro-1H-cyclobuta[e]indene ring system), the illudin moiety (2',2',4',6'-tetramethyl-octahydrospiro[cyclopropane-1,5'-indene]), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Illudanes and illudins

Alternative Parents

Substituents

Illudine sesquiterpenoid
Naphthopyran
Naphthalene
Furopyran
Cyclohexenone
Pyran
Oxane
Furan
Oxolane
Ketone
Acetal
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aldehyde
Primary alcohol
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	3.03	ALOGPS
logP	3.82	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	15.1	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	131.93 m³·mol⁻¹	ChemAxon
Polarizability	52.6 Å³	ChemAxon
Number of Rings	8	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

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

46853512

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione (NP0256837)

MOL for NP0256837 (21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione)

3D MOL for NP0256837 (21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione)

3D SDF for NP0256837 (21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione)

3D-SDF for NP0256837 (21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione)

PDB for NP0256837 (21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione)

3D PDB for NP0256837 (21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione)

SMILES for NP0256837 (21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione)

INCHI for NP0256837 (21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione)

Structure for NP0256837 (21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione)

3D Structure for NP0256837 (21'-(hydroxymethyl)-6',9',9',18',21'-pentamethyl-2',24'-dioxaspiro[cyclopropane-1,17'-heptacyclo[14.6.1.1³,⁶.0¹,¹⁹.0⁴,¹⁶.0⁵,¹³.0⁷,¹¹]tetracosane]-5'(13'),10',18'-triene-12',23'-dione)