NP-MRD: Showing NP-Card for 1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide (NP0351058)

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Record Information

Version

2.0

Created at

2025-05-27 23:15:20 UTC

Updated at

2026-03-21 04:35:05 UTC

NP-MRD ID

NP0351058

Natural Product DOI

https://doi.org/10.57994/4047

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide

Description

1-Hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review very few articles have been published on 1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03102301392D          

 21 22  0  0  1  0            999 V2000
   -4.6119    3.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3570    2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6586    2.8830    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3309    1.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8612    0.4623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6586    0.4170    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3570    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8419    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6669    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13  6  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 13 16  1  0  0  0  0
 17 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0351058

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-9(5-4-6-16)12-7-11-10(2)14(17)19-13(11)8-15(12,3)18/h7,9,11,13,16,18H,2,4-6,8H2,1,3H3/t9-,11+,13+,15+/m0/s1

> <INCHI_KEY>
YIVYUJIDBUSQBF-AGNJHWRGSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.037504540861534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,6R,7aR)-6-hydroxy-5-[(2S)-5-hydroxypentan-2-yl]-6-methyl-3-methylidene-2,3,3a,6,7,7a-hexahydro-1-benzofuran-2-one

> <JCHEM_LOGP>
1.1615629816666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.85558954542758

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.351736894386177

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9871595221338993

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
72.6882

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,6R,7aR)-6-hydroxy-5-[(2S)-5-hydroxypentan-2-yl]-6-methyl-3-methylidene-7,7a-dihydro-3aH-1-benzofuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-23         0                                  
HETATM    1  C   UNK     0      -8.609   5.791   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.133   4.326   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      -6.829   5.382   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.484   2.577   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.474   0.863   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      -6.829   0.778   0.000  0.00  0.00           H+0
HETATM   19  O   UNK     0      -8.133   1.834   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -9.038   3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -10.578   3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4    5   17                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    6   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16    3   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    2   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3370 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

(3aR,6R,7aR)-6-hydroxy-5-[(2S)-5-hydroxypentan-2-yl]-6-methyl-3-methylidene-2,3,3a,6,7,7a-hexahydro-1-benzofuran-2-one

Traditional Name

(3aR,6R,7aR)-6-hydroxy-5-[(2S)-5-hydroxypentan-2-yl]-6-methyl-3-methylidene-7,7a-dihydro-3aH-1-benzofuran-2-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H22O4/c1-9(5-4-6-16)12-7-11-10(2)14(17)19-13(11)8-15(12,3)18/h7,9,11,13,16,18H,2,4-6,8H2,1,3H3/t9-,11+,13+,15+/m0/s1

InChI Key

YIVYUJIDBUSQBF-AGNJHWRGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	[email protected]	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2025-05-27	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2025-05-27	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	[email protected]	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2025-05-27	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	[email protected]	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2025-05-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	[email protected]	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2025-05-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	[email protected]	Tianjin University of Traditional Chinese Medicine	Zheng Niu	2025-05-27	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Inula japonica		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Benzofuran
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	1.16	ChemAxon
pKa (Strongest Acidic)	14.35	ChemAxon
pKa (Strongest Basic)	-2	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	4	ChemAxon
Refractivity	72.69 m³·mol⁻¹	ChemAxon
Polarizability	29.04 Å³	ChemAxon
Number of Rings	2	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

Showing NP-Card for 1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide (NP0351058)

MOL for NP0351058 (1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide)

3D MOL for NP0351058 (1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide)

3D SDF for NP0351058 (1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide)

3D-SDF for NP0351058 (1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide)

PDB for NP0351058 (1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide)

3D PDB for NP0351058 (1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide)

SMILES for NP0351058 (1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide)

INCHI for NP0351058 (1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide)

Structure for NP0351058 (1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide)

3D Structure for NP0351058 (1-hydroxy-4αH-10α-hydroxy-1,10-secoeudesma-5(6),11(13)-dien-12,8β-olide)