NP-MRD: Showing NP-Card for 4β,10β-dihydroxy-1β(H)-5α(H)-guai-11(13)-en-8α,12-olide (NP0332747)

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Record Information

Version

1.0

Created at

2024-03-29 14:18:18 UTC

Updated at

2024-04-09 04:23:33 UTC

NP-MRD ID

NP0332747

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4β,10β-dihydroxy-1β(H)-5α(H)-guai-11(13)-en-8α,12-olide

Description

(3AR,4aR,5S,7aS,8R,9aS)-5,8-dihydroxy-5,8-dimethyl-3-methylidene-octahydroazuleno[6,5-b]furan-2-one belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Based on a literature review very few articles have been published on (3aR,4aR,5S,7aS,8R,9aS)-5,8-dihydroxy-5,8-dimethyl-3-methylidene-octahydroazuleno[6,5-b]furan-2-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03292414182D          

 23 25  0  0  1  0            999 V2000
   -0.3150   -0.6364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893   -0.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -0.7003    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4638   -1.2147    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621   -0.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3054   -0.7003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2684    0.1239    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890   -1.5046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3107   -1.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349   -0.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0136   -0.2772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4814    0.4024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747    0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6847   -1.3210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9746   -2.1496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7179   -2.5076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7910   -2.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1496   -2.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352   -1.5046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3110   -2.2632    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8136   -1.5786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0366    0.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  1  0  0  0
  9 15  1  1  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  6  0  0  0
 16 19  1  0  0  0  0
 20 19  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
  2 22  1  0  0  0  0
  3 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332747

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@](C)(O)[C@@]3([H])CC[C@@](C)(O)[C@]3([H])C[C@]1([H])C(=C)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-8-9-6-11-10(4-5-14(11,2)17)15(3,18)7-12(9)19-13(8)16/h9-12,17-18H,1,4-7H2,2-3H3/t9-,10+,11-,12+,14-,15+/m1/s1

> <INCHI_KEY>
WSMKPZGGGQUUQW-NJTCAMEISA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.711684070608705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4aR,5R,7aS,8S,9aS)-5,8-dihydroxy-5,8-dimethyl-3-methylidene-dodecahydroazuleno[6,5-b]furan-2-one

> <JCHEM_LOGP>
0.9893846533333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.04206463579001

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.429586769736105

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8971347390267734

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
69.81399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4aR,5R,7aS,8S,9aS)-5,8-dihydroxy-5,8-dimethyl-3-methylidene-octahydroazuleno[6,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-MAR-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-MAR-24         0                                  
HETATM    1  O   UNK     0      -0.588  -1.188   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.913  -1.531   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.073  -0.517   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.395  -1.307   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       4.599  -2.267   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0       4.783  -0.639   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.170  -1.307   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0       6.101   0.231   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0       6.513  -2.809   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.047  -2.947   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.652  -1.531   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.492  -0.517   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.365   0.751   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.859   0.887   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       5.011  -2.466   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       5.553  -4.013   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.940  -4.681   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.210  -5.514   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.013  -4.013   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.052  -2.809   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       2.447  -4.225   0.000  0.00  0.00           H+0
HETATM   22  O   UNK     0       1.519  -2.947   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.935   1.016   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5    6   20                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   12                                             
CONECT    8    7                                                            
CONECT    9    7   10   15   16                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13   14                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9                                                            
CONECT   16    9   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19    4   21   22                                             
CONECT   21   20                                                            
CONECT   22   20    2                                                       
CONECT   23    3                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3370 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

(3aR,4aR,5R,7aS,8S,9aS)-5,8-dihydroxy-5,8-dimethyl-3-methylidene-dodecahydroazuleno[6,5-b]furan-2-one

Traditional Name

(3aR,4aR,5R,7aS,8S,9aS)-5,8-dihydroxy-5,8-dimethyl-3-methylidene-octahydroazuleno[6,5-b]furan-2-one

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@](C)(O)[C@@]3([H])CC[C@@](C)(O)[C@]3([H])C[C@]1([H])C(=C)C(=O)O2

InChI Identifier

InChI=1S/C15H22O4/c1-8-9-6-11-10(4-5-14(11,2)17)15(3,18)7-12(9)19-13(8)16/h9-12,17-18H,1,4-7H2,2-3H3/t9-,10+,11-,12+,14-,15+/m1/s1

InChI Key

WSMKPZGGGQUUQW-NJTCAMEISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 601 MHz, CD3OD, experimental)	kibrom.gebrehiwot@aau.edu.et	Addis Ababa University	Kibrom Bedane	2024-03-29	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 601 MHz, CD3OD, experimental)	kibrom.gebrehiwot@aau.edu.et	Addis Ababa University	Kibrom Bedane	2024-03-29	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 601 MHz, CD3OD, experimental)	kibrom.gebrehiwot@aau.edu.et	Addis Ababa University	Kibrom Bedane	2024-03-29	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 601 MHz, CD3OD, experimental)	kibrom.gebrehiwot@aau.edu.et	Addis Ababa University	Kibrom Bedane	2024-03-29	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	kibrom.gebrehiwot@aau.edu.et	Addis Ababa University	Kibrom Bedane	2024-03-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	kibrom.gebrehiwot@aau.edu.et	Addis Ababa University	Kibrom Bedane	2024-03-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 601 MHz, CD3OD, experimental)	kibrom.gebrehiwot@aau.edu.et	Addis Ababa University	Kibrom Bedane	2024-03-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.503603 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151.012454643 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
confertiflora		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	0.99	ChemAxon
pKa (Strongest Acidic)	14.43	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.81 m³·mol⁻¹	ChemAxon
Polarizability	28.71 Å³	ChemAxon
Number of Rings	3	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

15275590

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4β,10β-dihydroxy-1β(H)-5α(H)-guai-11(13)-en-8α,12-olide (NP0332747)

MOL for NP0332747 (4β,10β-dihydroxy-1β(H)-5α(H)-guai-11(13)-en-8α,12-olide)

3D MOL for NP0332747 (4β,10β-dihydroxy-1β(H)-5α(H)-guai-11(13)-en-8α,12-olide)

3D SDF for NP0332747 (4β,10β-dihydroxy-1β(H)-5α(H)-guai-11(13)-en-8α,12-olide)

3D-SDF for NP0332747 (4β,10β-dihydroxy-1β(H)-5α(H)-guai-11(13)-en-8α,12-olide)

PDB for NP0332747 (4β,10β-dihydroxy-1β(H)-5α(H)-guai-11(13)-en-8α,12-olide)

3D PDB for NP0332747 (4β,10β-dihydroxy-1β(H)-5α(H)-guai-11(13)-en-8α,12-olide)

SMILES for NP0332747 (4β,10β-dihydroxy-1β(H)-5α(H)-guai-11(13)-en-8α,12-olide)

INCHI for NP0332747 (4β,10β-dihydroxy-1β(H)-5α(H)-guai-11(13)-en-8α,12-olide)

Structure for NP0332747 (4β,10β-dihydroxy-1β(H)-5α(H)-guai-11(13)-en-8α,12-olide)

3D Structure for NP0332747 (4β,10β-dihydroxy-1β(H)-5α(H)-guai-11(13)-en-8α,12-olide)