NP-MRD: Showing NP-Card for 3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one (NP0302429)

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Record Information

Version

2.0

Created at

2022-09-10 15:58:13 UTC

Updated at

2022-09-10 15:58:13 UTC

NP-MRD ID

NP0302429

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one

Description

3A-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-2H,3aH,4H,5H,5aH,6H,7H,8H,8aH-indeno[5,4-b]furan-2-one belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one is found in Phellinus igniarius. 3A-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-2H,3aH,4H,5H,5aH,6H,7H,8H,8aH-indeno[5,4-b]furan-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161522002D          

 26 28  0  0  0  0            999 V2000
    0.3925   -2.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210   -1.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5637   -1.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7352   -0.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5198   -0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6913    0.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4760    0.6592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329   -0.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7460   -1.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6849   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5809   -1.5678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341   -1.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7478   -0.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5015   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535   -0.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8785   -0.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4306   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1842   -0.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8987    0.0655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0980   -1.1675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910   -1.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7760   -2.0065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8785   -2.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535   -2.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410   -1.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1561   -2.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 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
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END


  Mrv1533004161522002D          

 26 28  0  0  0  0            999 V2000
    0.3925   -2.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210   -1.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5637   -1.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7352   -0.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5198   -0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6913    0.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4760    0.6592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329   -0.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7460   -1.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6849   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5809   -1.5678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341   -1.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7478   -0.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5015   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535   -0.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8785   -0.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4306   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1842   -0.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8987    0.0655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0980   -1.1675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910   -1.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7760   -2.0065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8785   -2.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535   -2.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410   -1.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1561   -2.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 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
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302429

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C=CC(CO)C(C)(C)O)C1CCC2C3=CC(=O)OC3(O)CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O5/c1-13(5-6-14(12-22)19(2,3)24)15-7-8-16-17-11-18(23)26-21(17,25)10-9-20(15,16)4/h5-6,11,13-16,22,24-25H,7-10,12H2,1-4H3

> <INCHI_KEY>
KNOYIRAECGPNAK-UHFFFAOYSA-N

> <FORMULA>
C21H32O5

> <MOLECULAR_WEIGHT>
364.482

> <EXACT_MASS>
364.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.089846726788906

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-2H,3aH,4H,5H,5aH,6H,7H,8H,8aH-indeno[5,4-b]furan-2-one

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.3571748186666657

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.793874573512024

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.270500398769995

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6482779340203546

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
101.12479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4H,5H,6H,7H,8H,8aH-indeno[5,4-b]furan-2-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       0.733  -4.716   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.412  -3.210   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.052  -2.734   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.372  -1.228   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.837  -0.752   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.157   0.755   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.622   1.231   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.981  -1.782   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.126  -2.813   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.012  -0.638   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.951  -2.927   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.557  -2.179   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.396  -0.648   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.803  -0.021   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.833  -1.166   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.373  -1.166   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.404  -0.021   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.811  -0.648   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.144   0.122   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.650  -2.179   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.143  -2.500   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.048  -3.745   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.373  -3.833   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.833  -3.833   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.063  -2.500   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.158  -3.745   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    2   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   16   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   12   15   26                                             
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₅

Average Mass

364.4820 Da

Monoisotopic Mass

364.22497 Da

IUPAC Name

3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-2H,3aH,4H,5H,5aH,6H,7H,8H,8aH-indeno[5,4-b]furan-2-one

Traditional Name

3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4H,5H,6H,7H,8H,8aH-indeno[5,4-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC(C=CC(CO)C(C)(C)O)C1CCC2C3=CC(=O)OC3(O)CCC12C

InChI Identifier

InChI=1S/C21H32O5/c1-13(5-6-14(12-22)19(2,3)24)15-7-8-16-17-11-18(23)26-21(17,25)10-9-20(15,16)4/h5-6,11,13-16,22,24-25H,7-10,12H2,1-4H3

InChI Key

KNOYIRAECGPNAK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phellinus igniarius	LOTUS Database	35616633

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
Fatty alcohol
2-furanone
Fatty acyl
Cyclic alcohol
Dihydrofuran
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Hemiacetal
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organic oxide
Alcohol
Organic oxygen compound
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	2.17	ALOGPS
logP	2.36	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	11.27	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.12 m³·mol⁻¹	ChemAxon
Polarizability	40.09 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

75238902

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one (NP0302429)

MOL for NP0302429 (3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one)

3D MOL for NP0302429 (3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one)

3D SDF for NP0302429 (3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one)

3D-SDF for NP0302429 (3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one)

PDB for NP0302429 (3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one)

3D PDB for NP0302429 (3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one)

SMILES for NP0302429 (3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one)

INCHI for NP0302429 (3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one)

Structure for NP0302429 (3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one)

3D Structure for NP0302429 (3a-hydroxy-6-[6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-5a-methyl-4h,5h,6h,7h,8h,8ah-indeno[5,4-b]furan-2-one)