NP-MRD: Showing NP-Card for (3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate (NP0207478)

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Record Information

Version

2.0

Created at

2022-09-05 04:06:33 UTC

Updated at

2022-09-05 04:06:33 UTC

NP-MRD ID

NP0207478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate

Description

DTXSID40949005 belongs to the class of organic compounds known as grayanoids. These are diterpenoids containing a skeleton based on or derived from the ent-kaurane moiety. Grayanoids usually possess either one of the grayanane, the 2,4-seco-grayanane, the 9,10-seco-grayanane, the 1,5-seco-grayanane, the kalmane, or the leucothane skeleton. Some derivatives also include the 1,5-seco-kalmane skeleton. (3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate is found in Rhododendron luteum and Rhododendron molle. Based on a literature review very few articles have been published on DTXSID40949005.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052206062D          

 32 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309052206062D          

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M  END
> <DATABASE_ID>
NP0207478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1[C@@H]2CC[C@@H]3C1(C[C@@]2(C)O)C[C@@H](OC(C)=O)[C@@]1(O)[C@@H]([C@@H]2O[C@@H]2C1(C)C)[C@]3(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O8/c1-11(25)30-15-9-23-10-21(5,27)13(18(23)31-12(2)26)7-8-14(23)22(6,28)17-16-19(32-16)20(3,4)24(15,17)29/h13-19,27-29H,7-10H2,1-6H3/t13-,14-,15+,16-,17-,18?,19-,21+,22+,23?,24+/m0/s1

> <INCHI_KEY>
BQXZYRJBFJGDSL-IDMDAGKXSA-N

> <FORMULA>
C24H36O8

> <MOLECULAR_WEIGHT>
452.544

> <EXACT_MASS>
452.241018119

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.35897848949398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R,6R,8S,9S,10R,11R,14S,15R)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0^{1,11}.0^{4,9}.0^{6,8}]heptadecan-3-yl acetate

> <JCHEM_LOGP>
0.01571311766666781

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.275023218098877

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.017596878113736

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9372974380097068

> <JCHEM_POLAR_SURFACE_AREA>
125.82000000000001

> <JCHEM_REFRACTIVITY>
110.74619999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R,6R,8S,9S,10R,11R,14S,15R)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0^{1,11}.0^{4,9}.0^{6,8}]heptadecan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       3.680   3.533   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.436   2.625   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.028   3.249   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.624   0.869   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.942  -0.510   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.806   0.272   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.726   1.615   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.316   1.472   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.908  -0.029   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.971  -1.386   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.637  -2.829   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.114  -3.322   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.661  -4.919   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.475  -5.982   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.791  -7.489   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.011  -5.502   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.396  -2.452   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.934  -3.915   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.544  -0.919   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.047  -0.586   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.587  -0.573   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.829  -1.914   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.808  -3.067   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.419  -3.465   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.496  -4.895   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.444   0.159   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.755   1.190   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.185   1.695   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.530  -2.239   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.235  -1.259   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.003  -2.324   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.195  -0.477   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9    5   11   29                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   20   26                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   22                                                       
CONECT   22   21   20   23                                                  
CONECT   23   22   17   24   25                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   19    9   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   10   30                                                       
CONECT   30   29    6   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₆O₈

Average Mass

452.5440 Da

Monoisotopic Mass

452.24102 Da

IUPAC Name

(3R,4R,6R,8S,9S,10R,11R,14S,15R)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0^{1,11}.0^{4,9}.0^{6,8}]heptadecan-3-yl acetate

Traditional Name

(3R,4R,6R,8S,9S,10R,11R,14S,15R)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0^{1,11}.0^{4,9}.0^{6,8}]heptadecan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1[C@@H]2CC[C@@H]3C1(C[C@@]2(C)O)C[C@@H](OC(C)=O)[C@@]1(O)[C@@H]([C@@H]2O[C@@H]2C1(C)C)[C@]3(C)O

InChI Identifier

InChI=1S/C24H36O8/c1-11(25)30-15-9-23-10-21(5,27)13(18(23)31-12(2)26)7-8-14(23)22(6,28)17-16-19(32-16)20(3,4)24(15,17)29/h13-19,27-29H,7-10H2,1-6H3/t13-,14-,15+,16-,17-,18?,19-,21+,22+,23?,24+/m0/s1

InChI Key

BQXZYRJBFJGDSL-IDMDAGKXSA-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
Rhododendron luteum	LOTUS Database	35616633
Rhododendron molle	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as grayanoids. These are diterpenoids containing a skeleton based on or derived from the ent-kaurane moiety. Grayanoids usually possess either one of the grayanane, the 2,4-seco-grayanane, the 9,10-seco-grayanane, the 1,5-seco-grayanane, the kalmane, or the leucothane skeleton. Some derivatives also include the 1,5-seco-kalmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Grayanoids

Alternative Parents

Substituents

Grayanoid
Oxane
Dicarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	0.016	ChemAxon
pKa (Strongest Acidic)	13.02	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	125.82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.75 m³·mol⁻¹	ChemAxon
Polarizability	47.36 Å³	ChemAxon
Number of Rings	5	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

171414

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

198050

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate (NP0207478)

MOL for NP0207478 ((3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

3D MOL for NP0207478 ((3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

3D SDF for NP0207478 ((3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

3D-SDF for NP0207478 ((3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

PDB for NP0207478 ((3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

3D PDB for NP0207478 ((3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

SMILES for NP0207478 ((3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

INCHI for NP0207478 ((3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

Structure for NP0207478 ((3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)

3D Structure for NP0207478 ((3r,4r,6r,8s,9s,10r,11r,14s,15r)-17-(acetyloxy)-4,10,15-trihydroxy-5,5,10,15-tetramethyl-7-oxapentacyclo[12.2.1.0¹,¹¹.0⁴,⁹.0⁶,⁸]heptadecan-3-yl acetate)