NP-MRD: Showing NP-Card for 10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one (NP0296505)

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Record Information

Version

2.0

Created at

2022-09-10 06:07:29 UTC

Updated at

2022-09-10 06:07:29 UTC

NP-MRD ID

NP0296505

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one

Description

10-Hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]Dodecan-3-one belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. 10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one is found in Salvia hypoleuca. 10-Hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]Dodecan-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161519252D          

 30 33  0  0  0  0            999 V2000
    1.2602   -3.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5927   -3.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2472   -4.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1729   -4.6747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0303   -5.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7901   -5.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3422   -6.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9617   -4.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6790   -2.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -1.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9463    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    1.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004161519252D          

 30 33  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0296505

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC1C(C)(O)CC2OC(=O)C3(C)CCCC1(C)C23)=CC1C(O)C=C(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O5/c1-14(11-16-17(26)12-15(2)20(16)27)7-8-19-23(3)9-6-10-24(4)21(23)18(30-22(24)28)13-25(19,5)29/h11-12,16-19,21,26,29H,6-10,13H2,1-5H3

> <INCHI_KEY>
FJSZKXFVEBZQTH-UHFFFAOYSA-N

> <FORMULA>
C25H36O5

> <MOLECULAR_WEIGHT>
416.558

> <EXACT_MASS>
416.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.88740724090113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
3.4993441269999987

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.640237217988947

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.379811717969137

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9359306409170234

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
115.98619999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       2.352  -6.763   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.106  -5.858   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.300  -6.484   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.461  -8.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.683  -9.046   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.189  -8.726   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.057 -10.453   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.475 -10.292   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.505 -11.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.795  -8.786   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.202  -8.159   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.267  -4.326   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.674  -3.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.835  -2.168   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.589  -1.263   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.914  -2.647   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.109  -0.839   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.750   0.268   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.157   0.895   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.633   2.359   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.173   2.359   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.078   3.605   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.649   0.895   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.793   1.925   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.056   0.268   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.217  -1.263   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.971  -2.168   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.242  -1.542   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.297  -3.081   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.403  -0.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10                                                            
CONECT   12    2   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   28                                                  
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   30                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   30                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   14   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   19   23                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₆O₅

Average Mass

416.5580 Da

Monoisotopic Mass

416.25627 Da

IUPAC Name

10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one

Traditional Name

10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one

CAS Registry Number

Not Available

SMILES

CC(CCC1C(C)(O)CC2OC(=O)C3(C)CCCC1(C)C23)=CC1C(O)C=C(C)C1=O

InChI Identifier

InChI=1S/C25H36O5/c1-14(11-16-17(26)12-15(2)20(16)27)7-8-19-23(3)9-6-10-24(4)21(23)18(30-22(24)28)13-25(19,5)29/h11-12,16-19,21,26,29H,6-10,13H2,1-5H3

InChI Key

FJSZKXFVEBZQTH-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
Salvia hypoleuca	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	3.11	ALOGPS
logP	3.5	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	115.99 m³·mol⁻¹	ChemAxon
Polarizability	46.89 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 10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one (NP0296505)

MOL for NP0296505 (10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one)

3D MOL for NP0296505 (10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one)

3D SDF for NP0296505 (10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one)

3D-SDF for NP0296505 (10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one)

PDB for NP0296505 (10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one)

3D PDB for NP0296505 (10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one)

SMILES for NP0296505 (10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one)

INCHI for NP0296505 (10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one)

Structure for NP0296505 (10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one)

3D Structure for NP0296505 (10-hydroxy-9-[4-(5-hydroxy-3-methyl-2-oxocyclopent-3-en-1-yl)-3-methylbut-3-en-1-yl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-3-one)