NP-MRD: Showing NP-Card for 2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol (NP0311990)

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Record Information

Version

2.0

Created at

2022-09-11 08:23:17 UTC

Updated at

2022-09-11 08:23:17 UTC

NP-MRD ID

NP0311990

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol

Description

2-{[4-Hydroxy-4b,8,8-trimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-3-yl]oxy}oxane-3,4,5-triol belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol is found in Avicennia marina. 2-{[4-Hydroxy-4b,8,8-trimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-3-yl]oxy}oxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251516082D          

 31 34  0  0  0  0            999 V2000
    0.7954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5206    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6021    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    3.2704   -2.9684    0.0000 O   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
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    3.6829   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2079   -3.6829    0.0000 O   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
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  9 16  1  0  0  0  0
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  6 18  2  0  0  0  0
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  4 21  1  0  0  0  0
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 28 30  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004251516082D          

 31 34  0  0  0  0            999 V2000
    0.7954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0311990

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC2=C(C(O)=C1OC1OCC(O)C(O)C1O)C1(C)CCCC(C)(C)C1CC2

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O6/c1-13(2)15-11-14-7-8-17-24(3,4)9-6-10-25(17,5)18(14)20(28)22(15)31-23-21(29)19(27)16(26)12-30-23/h11,13,16-17,19,21,23,26-29H,6-10,12H2,1-5H3

> <INCHI_KEY>
HTEXSXCVDJMYMF-UHFFFAOYSA-N

> <FORMULA>
C25H38O6

> <MOLECULAR_WEIGHT>
434.573

> <EXACT_MASS>
434.266838944

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
48.96687329624272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[4-hydroxy-4b,8,8-trimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-3-yl]oxy}oxane-3,4,5-triol

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
4.312208334333332

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.244015065537475

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.575503887236204

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265985260502335

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
117.87049999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-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  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.645  -2.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.875  -4.207   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.795  -4.207   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.565  -5.541   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.105  -5.541   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.875  -6.875   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.105  -8.208   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.875  -9.542   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.565  -8.208   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.795  -9.542   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.795  -6.875   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.255  -6.875   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    9   17   18                                             
CONECT   17   16                                                            
CONECT   18   16    6   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    4   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   23   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₈O₆

Average Mass

434.5730 Da

Monoisotopic Mass

434.26684 Da

IUPAC Name

2-{[4-hydroxy-4b,8,8-trimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthren-3-yl]oxy}oxane-3,4,5-triol

Traditional Name

2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC2=C(C(O)=C1OC1OCC(O)C(O)C1O)C1(C)CCCC(C)(C)C1CC2

InChI Identifier

InChI=1S/C25H38O6/c1-13(2)15-11-14-7-8-17-24(3,4)9-6-10-25(17,5)18(14)20(28)22(15)31-23-21(29)19(27)16(26)12-30-23/h11,13,16-17,19,21,23,26-29H,6-10,12H2,1-5H3

InChI Key

HTEXSXCVDJMYMF-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
Avicennia marina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Abietane diterpenoid
Diterpenoid
Phenolic glycoside
Hydrophenanthrene
Phenanthrene
Glycosyl compound
O-glycosyl compound
Pentose monosaccharide
Tetralin
1-hydroxy-4-unsubstituted benzenoid
Oxane
Benzenoid
Monosaccharide
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.91	ALOGPS
logP	4.31	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	10.58	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	117.87 m³·mol⁻¹	ChemAxon
Polarizability	48.97 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	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

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 2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol (NP0311990)

MOL for NP0311990 (2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol)

3D MOL for NP0311990 (2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol)

3D SDF for NP0311990 (2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol)

3D-SDF for NP0311990 (2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol)

PDB for NP0311990 (2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol)

3D PDB for NP0311990 (2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol)

SMILES for NP0311990 (2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol)

INCHI for NP0311990 (2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol)

Structure for NP0311990 (2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol)

3D Structure for NP0311990 (2-[(4-hydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-3-yl)oxy]oxane-3,4,5-triol)