NP-MRD: Showing NP-Card for (2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate (NP0311484)

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Record Information

Version

2.0

Created at

2022-09-11 07:30:37 UTC

Updated at

2022-09-11 07:30:37 UTC

NP-MRD ID

NP0311484

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate

Description

CHEMBL532590 belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate is found in Aster oharai. Based on a literature review very few articles have been published on CHEMBL532590.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112209302D          

 34 36  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309112209302D          

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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  1  0  0  0
  3 21  1  6  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 22 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0311484

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@](C)(CC[C@H]2C(C)=CC[C@H]3C(C)(C)CCC[C@]23C)C=C)[C@H](O)[C@H](OC(C)=O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O6/c1-9-27(7,34-25-23(31)24(33-19(4)29)22(30)18(3)32-25)16-13-20-17(2)11-12-21-26(5,6)14-10-15-28(20,21)8/h9,11,18,20-25,30-31H,1,10,12-16H2,2-8H3/t18-,20-,21-,22-,23+,24+,25-,27-,28+/m0/s1

> <INCHI_KEY>
WWGDINVWMUFHKK-KHBQPQIGSA-N

> <FORMULA>
C28H46O6

> <MOLECULAR_WEIGHT>
478.67

> <EXACT_MASS>
478.329439201

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.1388164932806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5S,6S)-2-{[(3R)-5-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate

> <JCHEM_LOGP>
4.963685664000002

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.275108516482856

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.270481421935829

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6269685605929984

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
132.17190000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5S,6S)-2-{[(3R)-5-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       6.311  -5.596   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.541  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.461  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   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  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001  -8.470   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668  -8.470   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668 -13.090   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335 -15.400   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001 -13.090   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   21                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   12    7   20                                             
CONECT   20   19                                                            
CONECT   21    3   22                                                       
CONECT   22   21   23   33                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   22   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₆O₆

Average Mass

478.6700 Da

Monoisotopic Mass

478.32944 Da

IUPAC Name

(2S,3R,4R,5S,6S)-2-{[(3R)-5-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate

Traditional Name

(2S,3R,4R,5S,6S)-2-{[(3R)-5-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@](C)(CC[C@H]2C(C)=CC[C@H]3C(C)(C)CCC[C@]23C)C=C)[C@H](O)[C@H](OC(C)=O)[C@H]1O

InChI Identifier

InChI=1S/C28H46O6/c1-9-27(7,34-25-23(31)24(33-19(4)29)22(30)18(3)32-25)16-13-20-17(2)11-12-21-26(5,6)14-10-15-28(20,21)8/h9,11,18,20-25,30-31H,1,10,12-16H2,2-8H3/t18-,20-,21-,22-,23+,24+,25-,27-,28+/m0/s1

InChI Key

WWGDINVWMUFHKK-KHBQPQIGSA-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
Aster oharai	LOTUS Database	35616633

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
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty acyl
Oxane
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	4.96	ChemAxon
pKa (Strongest Acidic)	12.27	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	132.17 m³·mol⁻¹	ChemAxon
Polarizability	54.14 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

24660079

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44576000

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate (NP0311484)

MOL for NP0311484 ((2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate)

3D MOL for NP0311484 ((2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate)

3D SDF for NP0311484 ((2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate)

3D-SDF for NP0311484 ((2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate)

PDB for NP0311484 ((2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate)

3D PDB for NP0311484 ((2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate)

SMILES for NP0311484 ((2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate)

INCHI for NP0311484 ((2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate)

Structure for NP0311484 ((2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate)

3D Structure for NP0311484 ((2s,3r,4r,5s,6s)-2-{[(3r)-5-[(1s,4as,8as)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl acetate)