NP-MRD: Showing NP-Card for rearranged OCT (NP0332420)

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Record Information

Version

2.0

Created at

2024-01-23 04:22:55 UTC

Updated at

2024-09-03 04:19:07 UTC

NP-MRD ID

NP0332420

Natural Product DOI

https://doi.org/10.57994/1639

Secondary Accession Numbers

None

Natural Product Identification

Common Name

rearranged OCT

Description

Rearranged OCT belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on rearranged OCT.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232404222D          

 22 25  0  0  1  0            999 V2000
   -0.3889    1.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074    1.2614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6775    1.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5457    1.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7942    0.9034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4924   -0.2362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6563    0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792    0.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484   -0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917   -0.4361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1537   -1.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0651   -0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2031    0.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5676    1.1906    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7056    2.0040    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9419    0.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8298    0.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762    0.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1319    0.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5692   -0.4646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3350   -0.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5158    0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  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  0  0  0  0
  7  9  1  0  0  0  0
 10  7  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 18  1  0  0  0  0
 20  6  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332420

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H](C)C(C)(C)[C@@]11CC[C@]3(C)CC[C@H](O1)C(C)=C3C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O/c1-13-6-7-15-12-16-14(2)17-8-9-19(16,5)10-11-20(15,21-17)18(13,3)4/h13,15,17H,6-12H2,1-5H3/t13-,15-,17-,19-,20+/m0/s1

> <INCHI_KEY>
WQEFYMFITTVIMZ-HRSMJWBKSA-N

> <FORMULA>
C20H32O

> <MOLECULAR_WEIGHT>
288.475

> <EXACT_MASS>
288.24531565

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
34.6686283778503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,6S,10S,13S)-2,2,3,9,13-pentamethyl-16-oxatetracyclo[8.5.1.0^{1,6}.0^{8,13}]hexadec-8-ene

> <JCHEM_LOGP>
4.972340588333331

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2231963330196765

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
87.83689999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,6S,10S,13S)-2,2,3,9,13-pentamethyl-16-oxatetracyclo[8.5.1.0^{1,6}.0^{8,13}]hexadec-8-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-JAN-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JAN-24         0                                  
HETATM    1  C   UNK     0      -0.726   3.419   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.387   2.355   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.265   3.679   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.885   3.602   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.349   1.686   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.786  -0.441   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.092   0.168   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.641   0.685   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.330  -1.171   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.278  -0.814   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.020  -2.332   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.721  -0.278   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.979   1.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.793   2.222   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       5.050   3.741   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       3.625   0.825   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.549   1.488   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.262   0.143   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.246   0.453   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.063  -0.867   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.625  -0.263   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.963   1.370   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   14                                             
CONECT    6    5   20                                                       
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14    5   13   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    2   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    6   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O

Average Mass

288.4750 Da

Monoisotopic Mass

288.24532 Da

IUPAC Name

(1R,3S,6S,10S,13S)-2,2,3,9,13-pentamethyl-16-oxatetracyclo[8.5.1.0^{1,6}.0^{8,13}]hexadec-8-ene

Traditional Name

(1R,3S,6S,10S,13S)-2,2,3,9,13-pentamethyl-16-oxatetracyclo[8.5.1.0^{1,6}.0^{8,13}]hexadec-8-ene

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H](C)C(C)(C)[C@@]11CC[C@]3(C)CC[C@H](O1)C(C)=C3C2

InChI Identifier

InChI=1S/C20H32O/c1-13-6-7-15-12-16-14(2)17-8-9-19(16,5)10-11-20(15,21-17)18(13,3)4/h13,15,17H,6-12H2,1-5H3/t13-,15-,17-,19-,20+/m0/s1

InChI Key

WQEFYMFITTVIMZ-HRSMJWBKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-29	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-29	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-29	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-27	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-27	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-27	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-27	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-26	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-26	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-26	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-26	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-26	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-25	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-25	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-25	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-25	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCL3, experimental)	ctliu@stanford.edu	Stanford	Jack Liu	2024-01-23	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
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	4.97	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.84 m³·mol⁻¹	ChemAxon
Polarizability	34.67 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for rearranged OCT (NP0332420)

MOL for NP0332420 (rearranged OCT)

3D MOL for NP0332420 (rearranged OCT)

3D SDF for NP0332420 (rearranged OCT)

3D-SDF for NP0332420 (rearranged OCT)

PDB for NP0332420 (rearranged OCT)

3D PDB for NP0332420 (rearranged OCT)

SMILES for NP0332420 (rearranged OCT)

INCHI for NP0332420 (rearranged OCT)

Structure for NP0332420 (rearranged OCT)

3D Structure for NP0332420 (rearranged OCT)