NP-MRD: Showing NP-Card for 4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one (NP0274745)

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Record Information

Version

2.0

Created at

2022-09-08 22:14:41 UTC

Updated at

2022-09-08 22:14:41 UTC

NP-MRD ID

NP0274745

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one

Description

4-[1-(5-Hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]but-3-en-2-one belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 4-[1-(5-Hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]but-3-en-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261502162D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004261502162D          

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    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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  4  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 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
 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
 18 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 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
  8 30  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32  9  1  4  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0274745

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C=CC1=C(CCC(C)=CCO)C2(C)CCCC(C)(CO)C2C(C1)OC1OCC(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O8/c1-17(10-13-29)6-9-20-19(8-7-18(2)31)14-22(36-26-24(34)23(33)21(32)15-35-26)25-27(3,16-30)11-5-12-28(20,25)4/h7-8,10,21-26,29-30,32-34H,5-6,9,11-16H2,1-4H3

> <INCHI_KEY>
AWVSBBCABYAQJD-UHFFFAOYSA-N

> <FORMULA>
C28H44O8

> <MOLECULAR_WEIGHT>
508.652

> <EXACT_MASS>
508.303618377

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.22119271824147

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]but-3-en-2-one

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
1.224026871333331

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.394793148617161

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.245624443578697

> <JCHEM_PKA_STRONGEST_BASIC>
-2.217047425569678

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
138.1895

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.841   0.912   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13   21                                                  
CONECT   21   20                                                            
CONECT   22   11   23   30                                                  
CONECT   23   22   24   25   27                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   23   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    8   22   31                                             
CONECT   31   30                                                            
CONECT   32    9   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₄O₈

Average Mass

508.6520 Da

Monoisotopic Mass

508.30362 Da

IUPAC Name

4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,5,6,7,8,8a-octahydronaphthalen-2-yl]but-3-en-2-one

Traditional Name

4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one

CAS Registry Number

Not Available

SMILES

CC(=O)C=CC1=C(CCC(C)=CCO)C2(C)CCCC(C)(CO)C2C(C1)OC1OCC(O)C(O)C1O

InChI Identifier

InChI=1S/C28H44O8/c1-17(10-13-29)6-9-20-19(8-7-18(2)31)14-22(36-26-24(34)23(33)21(32)15-35-26)25-27(3,16-30)11-5-12-28(20,25)4/h7-8,10,21-26,29-30,32-34H,5-6,9,11-16H2,1-4H3

InChI Key

AWVSBBCABYAQJD-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 diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Labdane diterpenoid
Diterpenoid
Glycosyl compound
O-glycosyl compound
Fatty alcohol
Fatty acyl
Oxane
Monosaccharide
Enone
Alpha,beta-unsaturated ketone
Acryloyl-group
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Acetal
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Primary alcohol
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	1.51	ALOGPS
logP	1.22	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	12.25	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	138.19 m³·mol⁻¹	ChemAxon
Polarizability	57.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

LOTUS database [Link]

Showing NP-Card for 4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one (NP0274745)

MOL for NP0274745 (4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one)

3D MOL for NP0274745 (4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one)

3D SDF for NP0274745 (4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one)

3D-SDF for NP0274745 (4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one)

PDB for NP0274745 (4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one)

3D PDB for NP0274745 (4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one)

SMILES for NP0274745 (4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one)

INCHI for NP0274745 (4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one)

Structure for NP0274745 (4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one)

3D Structure for NP0274745 (4-[1-(5-hydroxy-3-methylpent-3-en-1-yl)-5-(hydroxymethyl)-5,8a-dimethyl-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]but-3-en-2-one)