NP-MRD: Showing NP-Card for [6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate (NP0182175)

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Record Information

Version

2.0

Created at

2022-09-03 20:48:50 UTC

Updated at

2022-09-03 20:48:50 UTC

NP-MRD ID

NP0182175

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate

Description

[6,9-Dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2H,3H,3aH,4H,5H,5aH,6H,9H,10H,10aH-cyclohepta[e]inden-8-yl]methyl benzoate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. [6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate is found in Sarcodon scabrosus. Based on a literature review very few articles have been published on [6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2H,3H,3aH,4H,5H,5aH,6H,9H,10H,10aH-cyclohepta[e]inden-8-yl]methyl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032222482D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032222482D          

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M  END
> <DATABASE_ID>
NP0182175

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CO)C1=C2C3CC(O)C(COC(=O)C4=CC=CC=C4)=CC(O)C3(C)CCC2(CO)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O6/c1-17(14-28)20-8-9-27(16-29)11-10-26(2)21(24(20)27)13-22(30)19(12-23(26)31)15-33-25(32)18-6-4-3-5-7-18/h3-7,12,17,21-23,28-31H,8-11,13-16H2,1-2H3

> <INCHI_KEY>
VNIWCINJZQJXFB-UHFFFAOYSA-N

> <FORMULA>
C27H36O6

> <MOLECULAR_WEIGHT>
456.579

> <EXACT_MASS>
456.251188879

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.01207193618692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2H,3H,3aH,4H,5H,5aH,6H,9H,10H,10aH-cyclohepta[e]inden-8-yl]methyl benzoate

> <JCHEM_LOGP>
1.9865326113333341

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.73499619177252

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.085554802710849

> <JCHEM_PKA_STRONGEST_BASIC>
-1.065008692167027

> <JCHEM_POLAR_SURFACE_AREA>
107.22

> <JCHEM_REFRACTIVITY>
127.33050000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2H,3H,4H,5H,6H,9H,10H,10aH-cyclohepta[e]inden-8-yl]methyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.741  -0.579   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.251  -0.969   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.169   0.127   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.321  -0.263   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.844  -2.454   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.806  -3.656   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.343  -3.746   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.988  -2.348   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.484  -1.981   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.802  -0.474   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.703  -2.921   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.080  -2.230   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.366  -3.077   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.743  -2.386   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.832  -0.848   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.029  -3.232   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.405  -2.541   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.692  -3.388   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.602  -4.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.226  -5.616   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.939  -4.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.729  -4.461   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.541  -5.441   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.908  -6.936   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.034  -5.123   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.620  -6.547   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.187  -6.409   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.650  -6.319   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.959  -4.943   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.017  -6.134   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.537  -5.884   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.526  -4.535   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.597  -2.997   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6   33                                                  
CONECT    6    5    7   29                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   11   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    7   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    6   30   32                                             
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33                                                       
CONECT   33   32    5                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
[6,9-Dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2H,3H,3ah,4H,5H,5ah,6H,9H,10H,10ah-cyclohepta[e]inden-8-yl]methyl benzoic acid	Generator

Chemical Formula

C₂₇H₃₆O₆

Average Mass

456.5790 Da

Monoisotopic Mass

456.25119 Da

IUPAC Name

[6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2H,3H,3aH,4H,5H,5aH,6H,9H,10H,10aH-cyclohepta[e]inden-8-yl]methyl benzoate

Traditional Name

[6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2H,3H,4H,5H,6H,9H,10H,10aH-cyclohepta[e]inden-8-yl]methyl benzoate

CAS Registry Number

Not Available

SMILES

CC(CO)C1=C2C3CC(O)C(COC(=O)C4=CC=CC=C4)=CC(O)C3(C)CCC2(CO)CC1

InChI Identifier

InChI=1S/C27H36O6/c1-17(14-28)20-8-9-27(16-29)11-10-26(2)21(24(20)27)13-22(30)19(12-23(26)31)15-33-25(32)18-6-4-3-5-7-18/h3-7,12,17,21-23,28-31H,8-11,13-16H2,1-2H3

InChI Key

VNIWCINJZQJXFB-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
Sarcodon scabrosus	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

Diterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organic oxygen compound
Alcohol
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	1.99	ChemAxon
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	127.33 m³·mol⁻¹	ChemAxon
Polarizability	51.01 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

76012475

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate (NP0182175)

MOL for NP0182175 ([6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate)

3D MOL for NP0182175 ([6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate)

3D SDF for NP0182175 ([6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate)

3D-SDF for NP0182175 ([6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate)

PDB for NP0182175 ([6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate)

3D PDB for NP0182175 ([6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate)

SMILES for NP0182175 ([6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate)

INCHI for NP0182175 ([6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate)

Structure for NP0182175 ([6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate)

3D Structure for NP0182175 ([6,9-dihydroxy-3a-(hydroxymethyl)-1-(1-hydroxypropan-2-yl)-5a-methyl-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl benzoate)