NP-MRD: Showing NP-Card for (4s,4ar,5s,8r,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl (2z)-2-methylbut-2-enoate (NP0323604)

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Record Information

Version

2.0

Created at

2022-09-12 03:08:17 UTC

Updated at

2022-09-12 03:08:17 UTC

NP-MRD ID

NP0323604

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,4ar,5s,8r,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl (2z)-2-methylbut-2-enoate

Description

(4S,4aR,5S,8R,8aR)-4-(acetyloxy)-3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review very few articles have been published on (4S,4aR,5S,8R,8aR)-4-(acetyloxy)-3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl (2Z)-2-methylbut-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122205082D          

 27 29  0  0  1  0            999 V2000
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119    0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  2  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
  8 27  1  0  0  0  0
 13 27  1  0  0  0  0
M  END


  Mrv1652309122205082D          

 27 29  0  0  1  0            999 V2000
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119    0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  2  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
  8 27  1  0  0  0  0
 13 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0323604

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@@H]1CC[C@H](C)[C@]2(C)[C@H]1CC1=C([C@H]2OC(C)=O)C(C)=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-7-12(2)21(24)27-17-9-8-14(4)22(6)16(17)10-18-19(13(3)11-25-18)20(22)26-15(5)23/h7,11,14,16-17,20H,8-10H2,1-6H3/b12-7-/t14-,16-,17+,20+,22+/m0/s1

> <INCHI_KEY>
HLYBLRRKNWNJDY-MCLQFBEPSA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.477

> <EXACT_MASS>
374.209324066

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.64304052536393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,4aR,5S,8R,8aR)-4-(acetyloxy)-3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
4.700170672666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8118665315683264

> <JCHEM_POLAR_SURFACE_AREA>
65.74000000000001

> <JCHEM_REFRACTIVITY>
102.58229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aR,5S,8R,8aR)-4-(acetyloxy)-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.133  -0.294   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.609   1.171   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   27                                             
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   25                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26    8   13                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
(4S,4AR,5S,8R,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-8-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₂H₃₀O₅

Average Mass

374.4770 Da

Monoisotopic Mass

374.20932 Da

IUPAC Name

(4S,4aR,5S,8R,8aR)-4-(acetyloxy)-3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(4S,4aR,5S,8R,8aR)-4-(acetyloxy)-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-8-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@@H]1CC[C@H](C)[C@]2(C)[C@H]1CC1=C([C@H]2OC(C)=O)C(C)=CO1

InChI Identifier

InChI=1S/C22H30O5/c1-7-12(2)21(24)27-17-9-8-14(4)22(6)16(17)10-18-19(13(3)11-25-18)20(22)26-15(5)23/h7,11,14,16-17,20H,8-10H2,1-6H3/b12-7-/t14-,16-,17+,20+,22+/m0/s1

InChI Key

HLYBLRRKNWNJDY-MCLQFBEPSA-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 eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Furan
Heteroaromatic compound
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	4.7	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.74 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	102.58 m³·mol⁻¹	ChemAxon
Polarizability	41.64 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

163188853

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,4ar,5s,8r,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl (2z)-2-methylbut-2-enoate (NP0323604)

MOL for NP0323604 ((4s,4ar,5s,8r,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0323604 ((4s,4ar,5s,8r,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0323604 ((4s,4ar,5s,8r,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0323604 ((4s,4ar,5s,8r,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl (2z)-2-methylbut-2-enoate)

PDB for NP0323604 ((4s,4ar,5s,8r,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0323604 ((4s,4ar,5s,8r,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0323604 ((4s,4ar,5s,8r,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0323604 ((4s,4ar,5s,8r,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl (2z)-2-methylbut-2-enoate)

Structure for NP0323604 ((4s,4ar,5s,8r,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0323604 ((4s,4ar,5s,8r,8ar)-4-(acetyloxy)-3,4a,5-trimethyl-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-8-yl (2z)-2-methylbut-2-enoate)