NP-MRD: Showing NP-Card for 10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid (NP0201102)

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Record Information

Version

2.0

Created at

2022-09-04 20:04:58 UTC

Updated at

2022-09-04 20:04:58 UTC

NP-MRD ID

NP0201102

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid

Description

10-{4,10-Dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]Undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid is found in Streptomyces griseochromogenes. Based on a literature review very few articles have been published on 10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]Undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042222042D          

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M  END

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M  END


  Mrv1652309042222042D          

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  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  3  9  2  0  0  0  0
  9 10  1  4  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
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 24 32  1  0  0  0  0
 24 33  1  0  0  0  0
 18 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201102

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=CCCC(CO)CC(C)C1CC(O)C(C)C2(CC(O)C(C)C(C)O2)C1)C=CC(O)=N

> <INCHI_IDENTIFIER>
InChI=1S/C27H47NO5/c1-6-21(10-11-26(28)32)8-7-9-22(16-29)12-17(2)23-13-24(30)19(4)27(14-23)15-25(31)18(3)20(5)33-27/h8,10-11,17-20,22-25,29-31H,6-7,9,12-16H2,1-5H3,(H2,28,32)

> <INCHI_KEY>
PHXYBYWODHKWQV-UHFFFAOYSA-N

> <FORMULA>
C27H47NO5

> <MOLECULAR_WEIGHT>
465.675

> <EXACT_MASS>
465.345423617

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.958025959455085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid

> <JCHEM_LOGP>
0.9562781992449385

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.524975107873178

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4305614490546645

> <JCHEM_PKA_STRONGEST_BASIC>
12.767800322633446

> <JCHEM_POLAR_SURFACE_AREA>
114.00000000000001

> <JCHEM_REFRACTIVITY>
144.9417

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -5.335  -0.000   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.003  -8.470   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   33                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   32   33                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   24                                                       
CONECT   33   24   18                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidate	Generator

Chemical Formula

C₂₇H₄₇NO₅

Average Mass

465.6750 Da

Monoisotopic Mass

465.34542 Da

IUPAC Name

10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid

Traditional Name

10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid

CAS Registry Number

Not Available

SMILES

CCC(=CCCC(CO)CC(C)C1CC(O)C(C)C2(CC(O)C(C)C(C)O2)C1)C=CC(O)=N

InChI Identifier

InChI=1S/C27H47NO5/c1-6-21(10-11-26(28)32)8-7-9-22(16-29)12-17(2)23-13-24(30)19(4)27(14-23)15-25(31)18(3)20(5)33-27/h8,10-11,17-20,22-25,29-31H,6-7,9,12-16H2,1-5H3,(H2,28,32)

InChI Key

PHXYBYWODHKWQV-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
Streptomyces griseochromogenes	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Oxane
Cyclic alcohol
Secondary alcohol
Primary carboxylic acid amide
Carboxamide group
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	0.96	ChemAxon
pKa (Strongest Acidic)	1.43	ChemAxon
pKa (Strongest Basic)	12.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	114 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	144.94 m³·mol⁻¹	ChemAxon
Polarizability	54.96 Å³	ChemAxon
Number of Rings	2	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

162816285

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid (NP0201102)

MOL for NP0201102 (10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid)

3D MOL for NP0201102 (10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid)

3D SDF for NP0201102 (10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid)

3D-SDF for NP0201102 (10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid)

PDB for NP0201102 (10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid)

3D PDB for NP0201102 (10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid)

SMILES for NP0201102 (10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid)

INCHI for NP0201102 (10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid)

Structure for NP0201102 (10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid)

3D Structure for NP0201102 (10-{4,10-dihydroxy-2,3,11-trimethyl-1-oxaspiro[5.5]undecan-8-yl}-4-ethyl-8-(hydroxymethyl)undeca-2,4-dienimidic acid)