NP-MRD: Showing NP-Card for Rumphellolide H (NP0331819)

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Record Information

Version

1.0

Created at

2023-09-13 16:02:20 UTC

Updated at

2024-05-14 21:29:57 UTC

NP-MRD ID

NP0331819

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rumphellolide H

Description

(1R,2S,5R,8R,9R)-1-(hydroxymethyl)-4,4,8-trimethyl-12-oxatricyclo[6.3.1.0²,⁵]Dodecan-9-ol belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Based on a literature review very few articles have been published on (1R,2S,5R,8R,9R)-1-(hydroxymethyl)-4,4,8-trimethyl-12-oxatricyclo[6.3.1.0²,⁵]Dodecan-9-ol.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 09132316022D          

 20 22  0  0  1  0            999 V2000
   -1.7041    0.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8926    0.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0414    1.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438   -0.0676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0676    0.0812    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7793    0.4985    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7032   -0.4448    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4263   -1.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9609   -1.8504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0319    0.7345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5282   -0.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566    0.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    0.9088    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1058    1.0576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8769    1.6204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4029    2.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0998    1.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3265    1.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812    0.8926    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5589    1.5652    0.0000 H   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
  2  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 10  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  0  0  0  0
 19  2  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0331819

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC(C)(C)[C@]1([H])CC[C@]1(C)O[C@@]2(CO)CC[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O3/c1-13(2)8-11-10(13)4-6-14(3)12(17)5-7-15(11,9-16)18-14/h10-12,16-17H,4-9H2,1-3H3/t10-,11+,12-,14+,15-/m1/s1

> <INCHI_KEY>
HDEDHTVUKLACPT-FMKNKJFCSA-N

> <FORMULA>
C15H26O3

> <MOLECULAR_WEIGHT>
254.37

> <EXACT_MASS>
254.188194697

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
29.314304571555432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,8S,9R)-1-(hydroxymethyl)-4,4,8-trimethyl-12-oxatricyclo[6.3.1.0^{2,5}]dodecan-9-ol

> <JCHEM_LOGP>
1.6040565026666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.514157983070831

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.839237669982257

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0803513153937345

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
69.6612

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,8S,9R)-1-(hydroxymethyl)-4,4,8-trimethyl-12-oxatricyclo[6.3.1.0^{2,5}]dodecan-9-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-SEP-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-23         0                                  
HETATM    1  C   UNK     0      -3.181   1.111   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.666   1.389   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.944   2.903   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.389  -0.126   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.126   0.151   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       1.455   0.931   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       1.313  -0.830   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.796  -2.281   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.794  -3.454   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.926   1.371   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.853  -0.820   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.026   0.178   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.283   1.696   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.797   1.974   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.504   3.025   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.485   4.211   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.053   3.542   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.609   3.005   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.151   1.666   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      -1.043   2.922   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4   19                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   19                                             
CONECT    6    5                                                            
CONECT    7    5    8   10   11                                             
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   15                                                       
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   10   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    2    5   20                                             
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O₃

Average Mass

254.3700 Da

Monoisotopic Mass

254.18819 Da

IUPAC Name

(1S,2S,5R,8S,9R)-1-(hydroxymethyl)-4,4,8-trimethyl-12-oxatricyclo[6.3.1.0^{2,5}]dodecan-9-ol

Traditional Name

(1S,2S,5R,8S,9R)-1-(hydroxymethyl)-4,4,8-trimethyl-12-oxatricyclo[6.3.1.0^{2,5}]dodecan-9-ol

CAS Registry Number

Not Available

SMILES

[H][C@]12CC(C)(C)[C@]1([H])CC[C@]1(C)O[C@@]2(CO)CC[C@H]1O

InChI Identifier

InChI=1S/C15H26O3/c1-13(2)8-11-10(13)4-6-14(3)12(17)5-7-15(11,9-16)18-14/h10-12,16-17H,4-9H2,1-3H3/t10-,11+,12-,14+,15-/m1/s1

InChI Key

HDEDHTVUKLACPT-FMKNKJFCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 101 MHz, CDCl3, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 101 MHz, CDCl3, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100.578570142, CDCl₃, simulated)	st_george@inbox.lv	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2024-05-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101, CDCl₃, simulated)	st_george@inbox.lv	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2024-05-08	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Oxane
Cyclic alcohol
Secondary alcohol
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	1.6	ChemAxon
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.66 m³·mol⁻¹	ChemAxon
Polarizability	29.31 Å³	ChemAxon
Number of Rings	3	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

Not Available

Chemspider ID

29214043

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Rumphellolide H (NP0331819)

MOL for NP0331819 (Rumphellolide H)

3D MOL for NP0331819 (Rumphellolide H)

3D SDF for NP0331819 (Rumphellolide H)

3D-SDF for NP0331819 (Rumphellolide H)

PDB for NP0331819 (Rumphellolide H)

3D PDB for NP0331819 (Rumphellolide H)

SMILES for NP0331819 (Rumphellolide H)

INCHI for NP0331819 (Rumphellolide H)

Structure for NP0331819 (Rumphellolide H)

3D Structure for NP0331819 (Rumphellolide H)