NP-MRD: Showing NP-Card for 3-(furan-3-yl)-4a,7a-dihydroxy-5,8,8-trimethyl-hexahydro-3h-naphtho[4a,4-c]pyran-1,11-dione (NP0179335)

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Record Information

Version

2.0

Created at

2022-09-03 17:30:16 UTC

Updated at

2022-09-03 17:30:16 UTC

NP-MRD ID

NP0179335

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(furan-3-yl)-4a,7a-dihydroxy-5,8,8-trimethyl-hexahydro-3h-naphtho[4a,4-c]pyran-1,11-dione

Description

3-(Furan-3-yl)-7a,11b-dihydroxy-5,8,8-trimethyl-dodecahydronaphtho[4a,4-c]pyran-1,11-dione belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 3-(Furan-3-yl)-7a,11b-dihydroxy-5,8,8-trimethyl-dodecahydronaphtho[4a,4-c]pyran-1,11-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161507302D          

 26 29  0  0  0  0            999 V2000
    3.4939   -0.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8086    0.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682   -0.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3828    0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7466    0.6878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5946    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2503    0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2248    1.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3007    2.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927    2.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5126    2.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9109    1.5358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1784    1.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2335    2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5482    2.7843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739    2.6888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6593    2.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6041    1.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8637    1.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5490    0.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3997    2.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5406    3.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3572    3.5235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7210    2.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1293    2.2082    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 22 26  1  0  0  0  0
M  END


  Mrv1533004161507302D          

 26 29  0  0  0  0            999 V2000
    3.4939   -0.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8086    0.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682   -0.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3828    0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7466    0.6878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5946    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2503    0.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2248    1.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3007    2.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927    2.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5126    2.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9109    1.5358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1784    1.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2335    2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5482    2.7843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739    2.6888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6593    2.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6041    1.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8637    1.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5490    0.5832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3997    2.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5406    3.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3572    3.5235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7210    2.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1293    2.2082    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 22 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0179335

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(O)C(C)(C)CCC(=O)C22C(=O)OC(CC12O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O6/c1-12-4-8-19(24)17(2,3)7-5-15(21)20(19)16(22)26-14(10-18(12,20)23)13-6-9-25-11-13/h6,9,11-12,14,23-24H,4-5,7-8,10H2,1-3H3

> <INCHI_KEY>
DHVIVSFSRBQHPI-UHFFFAOYSA-N

> <FORMULA>
C20H26O6

> <MOLECULAR_WEIGHT>
362.422

> <EXACT_MASS>
362.172938557

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.5264023052636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(furan-3-yl)-7a,11b-dihydroxy-5,8,8-trimethyl-dodecahydronaphtho[4a,4-c]pyran-1,11-dione

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
2.0917369113333333

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.940962797868991

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.240893988956394

> <JCHEM_PKA_STRONGEST_BASIC>
-2.888640314872574

> <JCHEM_POLAR_SURFACE_AREA>
96.97

> <JCHEM_REFRACTIVITY>
91.7247

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(furan-3-yl)-7a,11b-dihydroxy-5,8,8-trimethyl-hexahydro-3H-naphtho[4a,4-c]pyran-1,11-dione

> <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       6.522  -0.448   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.243   0.409   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.861  -0.270   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.581   0.588   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.684   2.124   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.394   1.284   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.110   2.698   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.467   1.299   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.420   2.518   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.561   4.199   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.853   5.150   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.823   3.920   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.700   2.867   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.066   2.803   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.169   4.340   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.890   5.197   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.551   5.019   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.831   4.162   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.728   2.625   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.346   1.946   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.625   1.089   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.213   4.841   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.476   6.358   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.000   6.577   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.679   5.195   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.575   4.122   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   14                                             
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15   20                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19    2   14   21                                             
CONECT   21   20                                                            
CONECT   22   18   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₆

Average Mass

362.4220 Da

Monoisotopic Mass

362.17294 Da

IUPAC Name

3-(furan-3-yl)-7a,11b-dihydroxy-5,8,8-trimethyl-dodecahydronaphtho[4a,4-c]pyran-1,11-dione

Traditional Name

3-(furan-3-yl)-7a,11b-dihydroxy-5,8,8-trimethyl-hexahydro-3H-naphtho[4a,4-c]pyran-1,11-dione

CAS Registry Number

Not Available

SMILES

CC1CCC2(O)C(C)(C)CCC(=O)C22C(=O)OC(CC12O)C1=COC=C1

InChI Identifier

InChI=1S/C20H26O6/c1-12-4-8-19(24)17(2,3)7-5-15(21)20(19)16(22)26-14(10-18(12,20)23)13-6-9-25-11-13/h6,9,11-12,14,23-24H,4-5,7-8,10H2,1-3H3

InChI Key

DHVIVSFSRBQHPI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Naphthopyranone
Naphthopyran
Delta valerolactone
Delta_valerolactone
Oxane
Tertiary alcohol
Cyclic alcohol
Heteroaromatic compound
Furan
Carboxylic acid ester
Ketone
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
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	1.89	ALOGPS
logP	2.09	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.24	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.97 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.72 m³·mol⁻¹	ChemAxon
Polarizability	37.53 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 3-(furan-3-yl)-4a,7a-dihydroxy-5,8,8-trimethyl-hexahydro-3h-naphtho[4a,4-c]pyran-1,11-dione (NP0179335)

MOL for NP0179335 (3-(furan-3-yl)-4a,7a-dihydroxy-5,8,8-trimethyl-hexahydro-3h-naphtho[4a,4-c]pyran-1,11-dione)

3D MOL for NP0179335 (3-(furan-3-yl)-4a,7a-dihydroxy-5,8,8-trimethyl-hexahydro-3h-naphtho[4a,4-c]pyran-1,11-dione)

3D SDF for NP0179335 (3-(furan-3-yl)-4a,7a-dihydroxy-5,8,8-trimethyl-hexahydro-3h-naphtho[4a,4-c]pyran-1,11-dione)

3D-SDF for NP0179335 (3-(furan-3-yl)-4a,7a-dihydroxy-5,8,8-trimethyl-hexahydro-3h-naphtho[4a,4-c]pyran-1,11-dione)

PDB for NP0179335 (3-(furan-3-yl)-4a,7a-dihydroxy-5,8,8-trimethyl-hexahydro-3h-naphtho[4a,4-c]pyran-1,11-dione)

3D PDB for NP0179335 (3-(furan-3-yl)-4a,7a-dihydroxy-5,8,8-trimethyl-hexahydro-3h-naphtho[4a,4-c]pyran-1,11-dione)

SMILES for NP0179335 (3-(furan-3-yl)-4a,7a-dihydroxy-5,8,8-trimethyl-hexahydro-3h-naphtho[4a,4-c]pyran-1,11-dione)

INCHI for NP0179335 (3-(furan-3-yl)-4a,7a-dihydroxy-5,8,8-trimethyl-hexahydro-3h-naphtho[4a,4-c]pyran-1,11-dione)

Structure for NP0179335 (3-(furan-3-yl)-4a,7a-dihydroxy-5,8,8-trimethyl-hexahydro-3h-naphtho[4a,4-c]pyran-1,11-dione)

3D Structure for NP0179335 (3-(furan-3-yl)-4a,7a-dihydroxy-5,8,8-trimethyl-hexahydro-3h-naphtho[4a,4-c]pyran-1,11-dione)