NP-MRD: Showing NP-Card for 2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal (NP0154827)

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Record Information

Version

2.0

Created at

2022-09-02 11:47:56 UTC

Updated at

2022-09-02 11:47:56 UTC

NP-MRD ID

NP0154827

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal

Description

2-(4-Hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. 2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal is found in Iris tectorum. 2-(4-Hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191520402D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004191520402D          

 35 36  0  0  0  0            999 V2000
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   -1.9634   -6.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4331   -6.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207   -6.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7153   -7.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1850   -8.1512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7759   -6.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3062   -5.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0240   -4.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7890   -4.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1956   -4.0410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5876   -2.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4021   -2.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  4  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 17 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  6 34  1  0  0  0  0
  2 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154827

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(C)=CCC(O)C1(C)OC1CCC1(C)C(CCCO)C(CCC1(C)O)=C(C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O5/c1-21(2)10-8-11-22(3)13-14-26(33)30(7)27(35-30)16-17-28(5)25(12-9-19-31)24(23(4)20-32)15-18-29(28,6)34/h10,13,20,25-27,31,33-34H,8-9,11-12,14-19H2,1-7H3

> <INCHI_KEY>
PWIUYVBRAXUOPC-UHFFFAOYSA-N

> <FORMULA>
C30H50O5

> <MOLECULAR_WEIGHT>
490.725

> <EXACT_MASS>
490.36582471

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
58.32016219081661

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal

> <ALOGPS_LOGP>
4.78

> <JCHEM_LOGP>
4.649625225333333

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.85557133079531

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.859017265066171

> <JCHEM_PKA_STRONGEST_BASIC>
-0.303469095424301

> <JCHEM_POLAR_SURFACE_AREA>
90.29

> <JCHEM_REFRACTIVITY>
145.0659

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.26e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal

> <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      10.996  -1.526   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.816  -2.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.369  -1.989   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.190  -2.979   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.742  -2.452   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.563  -3.442   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.116  -2.915   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.936  -3.905   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.489  -3.379   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.221  -1.862   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.691  -4.369   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.871  -3.379   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.079  -5.702   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.461  -5.702   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.795  -6.472   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.795  -8.012   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.128  -8.782   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.655  -7.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.138  -9.962   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.622  -9.694   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.095  -8.247   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.422  -7.980   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.411  -9.160   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.665 -11.409   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.675 -12.589   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.159 -12.321   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.202 -14.036   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.212 -15.216   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.182 -11.676   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.172 -10.497   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.645  -9.050   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -7.073  -8.473   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.965  -7.543   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.830  -4.959   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.084  -4.032   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   11   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   31                                             
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   19   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   24   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   17   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    6                                                            
CONECT   35    2                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₀O₅

Average Mass

490.7250 Da

Monoisotopic Mass

490.36582 Da

IUPAC Name

2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal

Traditional Name

2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(C)=CCC(O)C1(C)OC1CCC1(C)C(CCCO)C(CCC1(C)O)=C(C)C=O

InChI Identifier

InChI=1S/C30H50O5/c1-21(2)10-8-11-22(3)13-14-26(33)30(7)27(35-30)16-17-28(5)25(12-9-19-31)24(23(4)20-32)15-18-29(28,6)34/h10,13,20,25-27,31,33-34H,8-9,11-12,14-19H2,1-7H3

InChI Key

PWIUYVBRAXUOPC-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
Iris tectorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Fatty alcohol
Fatty acyl
Alpha,beta-unsaturated aldehyde
Cyclic alcohol
Enal
Tertiary alcohol
Secondary alcohol
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Aldehyde
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	4.78	ALOGPS
logP	4.65	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-0.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.29 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	145.07 m³·mol⁻¹	ChemAxon
Polarizability	58.32 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

73307303

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal (NP0154827)

MOL for NP0154827 (2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal)

3D MOL for NP0154827 (2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal)

3D SDF for NP0154827 (2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal)

3D-SDF for NP0154827 (2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal)

PDB for NP0154827 (2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal)

3D PDB for NP0154827 (2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal)

SMILES for NP0154827 (2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal)

INCHI for NP0154827 (2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal)

Structure for NP0154827 (2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal)

3D Structure for NP0154827 (2-(4-hydroxy-3-{2-[3-(1-hydroxy-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl]ethyl}-2-(3-hydroxypropyl)-3,4-dimethylcyclohexylidene)propanal)