NP-MRD: Showing NP-Card for {5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate (NP0218954)

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Record Information

Version

2.0

Created at

2022-09-05 19:47:04 UTC

Updated at

2022-09-05 19:47:04 UTC

NP-MRD ID

NP0218954

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate

Description

{5-Hydroxy-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. {5-Hydroxy-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201502172D          

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M  END

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M  END


  Mrv1533004201502172D          

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    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
  6 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  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
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218954

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC2=C(C(O)=C1OC(=O)C=C(C)C)C1(C)CCCC(C)(COC(=O)C3=CC=C(O)C(O)=C3)C1CC2

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O7/c1-18(2)14-26(35)39-29-22(19(3)4)15-20-9-11-25-31(5,12-7-13-32(25,6)27(20)28(29)36)17-38-30(37)21-8-10-23(33)24(34)16-21/h8,10,14-16,19,25,33-34,36H,7,9,11-13,17H2,1-6H3

> <INCHI_KEY>
QIRPXSKEFCGQDR-UHFFFAOYSA-N

> <FORMULA>
C32H40O7

> <MOLECULAR_WEIGHT>
536.665

> <EXACT_MASS>
536.277403628

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
59.88112805136559

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{5-hydroxy-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate

> <ALOGPS_LOGP>
6.16

> <JCHEM_LOGP>
8.737788437

> <ALOGPS_LOGS>
-5.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.951055027266255

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.55888306841189

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9169587979126126

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
151.00180000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       1.485  -2.874   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.255  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.485  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.172   0.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.457   1.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.010   1.837   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.743   3.354   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.922   4.343   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.296   3.880   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.116   2.890   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.669   3.417   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.401   4.934   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.954   5.460   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.581   5.924   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.314   7.440   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.028   5.397   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.645  -2.874   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.875  -4.207   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.795  -4.207   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.565  -5.541   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.795  -6.875   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.105  -5.541   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.875  -6.875   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.415  -6.875   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.105  -8.208   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   27                                                  
CONECT   10    9   11   12   24                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16                                                       
CONECT   24   10   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    9   28   29                                             
CONECT   28   27                                                            
CONECT   29   27    6   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    4   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
{5-hydroxy-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoic acid	Generator

Chemical Formula

C₃₂H₄₀O₇

Average Mass

536.6650 Da

Monoisotopic Mass

536.27740 Da

IUPAC Name

{5-hydroxy-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate

Traditional Name

{5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC2=C(C(O)=C1OC(=O)C=C(C)C)C1(C)CCCC(C)(COC(=O)C3=CC=C(O)C(O)=C3)C1CC2

InChI Identifier

InChI=1S/C32H40O7/c1-18(2)14-26(35)39-29-22(19(3)4)15-20-9-11-25-31(5,12-7-13-32(25,6)27(20)28(29)36)17-38-30(37)21-8-10-23(33)24(34)16-21/h8,10,14-16,19,25,33-34,36H,7,9,11-13,17H2,1-6H3

InChI Key

QIRPXSKEFCGQDR-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

Diterpenoid
Abietane diterpenoid
Hydrophenanthrene
Phenanthrene
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Benzoate ester
Phenol ester
Tetralin
Benzoic acid or derivatives
Cumene
Benzoyl
Catechol
Phenol
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	6.16	ALOGPS
logP	8.74	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	8.56	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	151 m³·mol⁻¹	ChemAxon
Polarizability	59.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

77916021

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate (NP0218954)

MOL for NP0218954 ({5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate)

3D MOL for NP0218954 ({5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate)

3D SDF for NP0218954 ({5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate)

3D-SDF for NP0218954 ({5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate)

PDB for NP0218954 ({5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate)

3D PDB for NP0218954 ({5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate)

SMILES for NP0218954 ({5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate)

INCHI for NP0218954 ({5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate)

Structure for NP0218954 ({5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate)

3D Structure for NP0218954 ({5-hydroxy-7-isopropyl-1,4a-dimethyl-6-[(3-methylbut-2-enoyl)oxy]-2,3,4,9,10,10a-hexahydrophenanthren-1-yl}methyl 3,4-dihydroxybenzoate)