NP-MRD: Showing NP-Card for macrophyllilactone E (NP0031653)

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Record Information

Version

2.0

Created at

2021-06-19 22:40:18 UTC

Updated at

2021-06-30 00:00:22 UTC

NP-MRD ID

NP0031653

Secondary Accession Numbers

None

Natural Product Identification

Common Name

macrophyllilactone E

Provided By

JEOL Database JEOL Logo

Description

Macrophyllilactone E belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. macrophyllilactone E is found in Inula helenium, Inula macrophylla and Inula racemosa. macrophyllilactone E was first documented in 2001 (Fu, B., et al.). Based on a literature review very few articles have been published on Macrophyllilactone E.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100403D          

 38 40  0  0  0  0            999 V2000
    1.9794   -0.4855   -2.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5299   -1.6961   -1.9804 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4795   -2.4863   -2.7773 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0477   -3.7560   -2.0509 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4850   -3.4396   -0.6561 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4939   -2.6174    0.2215 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6946   -3.4964    0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2854   -2.2003    1.5100 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4099   -1.0474    2.2149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3386   -0.5451    3.3138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4409    0.8069    3.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    1.5610    4.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0805    1.2220    1.8634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0631    2.6415    1.4650 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4672    2.8861    0.1692 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5155    0.1005    1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9834   -0.1458   -0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125   -1.3909   -0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7908    0.0566   -2.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1531    0.2113   -2.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.8077   -3.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4189   -2.3307   -1.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010   -1.8573   -2.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -2.7627   -3.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -4.2598   -2.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8892   -4.4551   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7474   -4.3777   -0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -2.8835   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2410   -3.8989   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -4.3530    1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4168   -2.9334    1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3135   -1.8986    1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -3.0481    2.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943   -1.3513    2.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199    2.9282    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4707    3.2859    2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179    3.8287   -0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2915    0.7214   -0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  2  0  0  0  0
 13 11  1  0  0  0  0
 11 10  1  0  0  0  0
 10  9  1  0  0  0  0
 17 16  1  0  0  0  0
 11 12  2  0  0  0  0
 18  2  1  0  0  0  0
  9 34  1  1  0  0  0
  6  5  1  0  0  0  0
  6  7  1  1  0  0  0
  9 16  1  0  0  0  0
  2  1  1  0  0  0  0
  9  8  1  0  0  0  0
 13 14  1  0  0  0  0
 18  6  1  0  0  0  0
 14 15  1  0  0  0  0
 16 13  2  0  0  0  0
  6  8  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  3  2  1  0  0  0  0
 17 38  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  2 22  1  1  0  0  0
  7 29  1  0  0  0  0
  7 30  1  0  0  0  0
  7 31  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
 15 37  1  0  0  0  0
  4 25  1  0  0  0  0
  4 26  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
M  END

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    1.9794   -0.4855   -2.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5299   -1.6961   -1.9804 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4795   -2.4863   -2.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0477   -3.7560   -2.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4850   -3.4396   -0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4939   -2.6174    0.2215 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6946   -3.4964    0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2854   -2.2003    1.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099   -1.0474    2.2149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3386   -0.5451    3.3138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4409    0.8069    3.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    1.5610    4.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0805    1.2220    1.8634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0631    2.6415    1.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    2.8861    0.1692 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5155    0.1005    1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9834   -0.1458   -0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125   -1.3909   -0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7908    0.0566   -2.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1531    0.2113   -2.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.8077   -3.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4189   -2.3307   -1.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010   -1.8573   -2.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -2.7627   -3.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -4.2598   -2.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8892   -4.4551   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7474   -4.3777   -0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -2.8835   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2410   -3.8989   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -4.3530    1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4168   -2.9334    1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3135   -1.8986    1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -3.0481    2.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943   -1.3513    2.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199    2.9282    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4707    3.2859    2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179    3.8287   -0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2915    0.7214   -0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  2  0
 13 11  1  0
 11 10  1  0
 10  9  1  0
 17 16  1  0
 11 12  2  0
 18  2  1  0
  9 34  1  1
  6  5  1  0
  6  7  1  1
  9 16  1  0
  2  1  1  0
  9  8  1  0
 13 14  1  0
 18  6  1  0
 14 15  1  0
 16 13  2  0
  6  8  1  0
  4  3  1  0
  5  4  1  0
  3  2  1  0
 17 38  1  0
  8 32  1  0
  8 33  1  0
  5 27  1  0
  5 28  1  0
  2 22  1  1
  7 29  1  0
  7 30  1  0
  7 31  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
  4 25  1  0
  4 26  1  0
  3 23  1  0
  3 24  1  0
M  END


  Mrv1652306202100403D          

 38 40  0  0  0  0            999 V2000
    1.9794   -0.4855   -2.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5299   -1.6961   -1.9804 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4795   -2.4863   -2.7773 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0477   -3.7560   -2.0509 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4850   -3.4396   -0.6561 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4939   -2.6174    0.2215 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6946   -3.4964    0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2854   -2.2003    1.5100 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4099   -1.0474    2.2149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3386   -0.5451    3.3138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4409    0.8069    3.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    1.5610    4.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0805    1.2220    1.8634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0631    2.6415    1.4650 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4672    2.8861    0.1692 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5155    0.1005    1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9834   -0.1458   -0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125   -1.3909   -0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7908    0.0566   -2.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1531    0.2113   -2.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.8077   -3.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4189   -2.3307   -1.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010   -1.8573   -2.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -2.7627   -3.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -4.2598   -2.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8892   -4.4551   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7474   -4.3777   -0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -2.8835   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2410   -3.8989   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -4.3530    1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4168   -2.9334    1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3135   -1.8986    1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -3.0481    2.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943   -1.3513    2.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199    2.9282    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4707    3.2859    2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179    3.8287   -0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2915    0.7214   -0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  2  0  0  0  0
 13 11  1  0  0  0  0
 11 10  1  0  0  0  0
 10  9  1  0  0  0  0
 17 16  1  0  0  0  0
 11 12  2  0  0  0  0
 18  2  1  0  0  0  0
  9 34  1  1  0  0  0
  6  5  1  0  0  0  0
  6  7  1  1  0  0  0
  9 16  1  0  0  0  0
  2  1  1  0  0  0  0
  9  8  1  0  0  0  0
 13 14  1  0  0  0  0
 18  6  1  0  0  0  0
 14 15  1  0  0  0  0
 16 13  2  0  0  0  0
  6  8  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  3  2  1  0  0  0  0
 17 38  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  2 22  1  1  0  0  0
  7 29  1  0  0  0  0
  7 30  1  0  0  0  0
  7 31  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
 15 37  1  0  0  0  0
  4 25  1  0  0  0  0
  4 26  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031653

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C2C([H])=C3[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])C([H])([H])[C@]2([H])OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-4-3-5-15(2)7-13-10(6-12(9)15)11(8-16)14(17)18-13/h6,9,13,16H,3-5,7-8H2,1-2H3/t9-,13+,15-/m1/s1

> <INCHI_KEY>
QBLRXHAPLQNELR-ZDBHGNHJSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.600998188803516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,8aR,9aS)-3-(hydroxymethyl)-5,8a-dimethyl-2H,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
1.99563273

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.955100891641102

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.085274567119427

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8644816728275346

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
69.7735

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,8aR,9aS)-3-(hydroxymethyl)-5,8a-dimethyl-5H,6H,7H,8H,9H,9aH-naphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    1.9794   -0.4855   -2.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5299   -1.6961   -1.9804 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4795   -2.4863   -2.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0477   -3.7560   -2.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4850   -3.4396   -0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4939   -2.6174    0.2215 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6946   -3.4964    0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2854   -2.2003    1.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099   -1.0474    2.2149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3386   -0.5451    3.3138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4409    0.8069    3.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    1.5610    4.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0805    1.2220    1.8634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0631    2.6415    1.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    2.8861    0.1692 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5155    0.1005    1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9834   -0.1458   -0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125   -1.3909   -0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7908    0.0566   -2.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1531    0.2113   -2.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.8077   -3.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4189   -2.3307   -1.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010   -1.8573   -2.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -2.7627   -3.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -4.2598   -2.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8892   -4.4551   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7474   -4.3777   -0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -2.8835   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2410   -3.8989   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -4.3530    1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4168   -2.9334    1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3135   -1.8986    1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -3.0481    2.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943   -1.3513    2.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199    2.9282    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4707    3.2859    2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179    3.8287   -0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2915    0.7214   -0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  2  0
 13 11  1  0
 11 10  1  0
 10  9  1  0
 17 16  1  0
 11 12  2  0
 18  2  1  0
  9 34  1  1
  6  5  1  0
  6  7  1  1
  9 16  1  0
  2  1  1  0
  9  8  1  0
 13 14  1  0
 18  6  1  0
 14 15  1  0
 16 13  2  0
  6  8  1  0
  4  3  1  0
  5  4  1  0
  3  2  1  0
 17 38  1  0
  8 32  1  0
  8 33  1  0
  5 27  1  0
  5 28  1  0
  2 22  1  1
  7 29  1  0
  7 30  1  0
  7 31  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
  4 25  1  0
  4 26  1  0
  3 23  1  0
  3 24  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       1.979  -0.486  -2.810  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.530  -1.696  -1.980  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.480  -2.486  -2.777  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.048  -3.756  -2.051  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.485  -3.440  -0.656  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.494  -2.617   0.222  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.695  -3.496   0.641  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.285  -2.200   1.510  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.410  -1.047   2.215  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.339  -0.545   3.314  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.441   0.807   3.176  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.927   1.561   4.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.081   1.222   1.863  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.063   2.642   1.465  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.467   2.886   0.169  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.516   0.101   1.289  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.983  -0.146  -0.047  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.012  -1.391  -0.571  0.00  0.00           C+0
HETATM   19  H   UNK     0       2.791   0.057  -2.312  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.153   0.211  -2.989  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.359  -0.808  -3.786  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.419  -2.331  -1.868  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.401  -1.857  -2.964  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.884  -2.763  -3.759  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.733  -4.260  -2.632  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.889  -4.455  -1.989  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.747  -4.378  -0.151  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.425  -2.884  -0.778  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.241  -3.899  -0.217  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.362  -4.353   1.239  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.417  -2.933   1.243  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.313  -1.899   1.262  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.398  -3.048   2.198  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.394  -1.351   2.590  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.120   2.928   1.458  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.471   3.286   2.171  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.318   3.829  -0.017  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.292   0.721  -0.623  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2   18    1    3   22                                             
CONECT    3    4    2   23   24                                             
CONECT    4    3    5   25   26                                             
CONECT    5    6    4   27   28                                             
CONECT    6    5    7   18    8                                             
CONECT    7    6   29   30   31                                             
CONECT    8    9    6   32   33                                             
CONECT    9   10   34   16    8                                             
CONECT   10   11    9                                                       
CONECT   11   13   10   12                                                  
CONECT   12   11                                                            
CONECT   13   11   14   16                                                  
CONECT   14   13   15   35   36                                             
CONECT   15   14   37                                                       
CONECT   16   17    9   13                                                  
CONECT   17   18   16   38                                                  
CONECT   18   17    2    6                                                  
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    4                                                            
CONECT   27    5                                                            
CONECT   28    5                                                            
CONECT   29    7                                                            
CONECT   30    7                                                            
CONECT   31    7                                                            
CONECT   32    8                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   14                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   17                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

RDKit          3D

38 40  0  0  0  0  0  0  0  0999 V2000
    1.9794   -0.4855   -2.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5299   -1.6961   -1.9804 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4795   -2.4863   -2.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0477   -3.7560   -2.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4850   -3.4396   -0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4939   -2.6174    0.2215 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6946   -3.4964    0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2854   -2.2003    1.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099   -1.0474    2.2149 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3386   -0.5451    3.3138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4409    0.8069    3.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    1.5610    4.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0805    1.2220    1.8634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0631    2.6415    1.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    2.8861    0.1692 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5155    0.1005    1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9834   -0.1458   -0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125   -1.3909   -0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7908    0.0566   -2.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1531    0.2113   -2.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.8077   -3.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4189   -2.3307   -1.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4010   -1.8573   -2.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -2.7627   -3.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -4.2598   -2.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8892   -4.4551   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7474   -4.3777   -0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249   -2.8835   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2410   -3.8989   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -4.3530    1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4168   -2.9334    1.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3135   -1.8986    1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -3.0481    2.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943   -1.3513    2.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199    2.9282    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4707    3.2859    2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179    3.8287   -0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2915    0.7214   -0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  2  0
 13 11  1  0
 11 10  1  0
 10  9  1  0
 17 16  1  0
 11 12  2  0
 18  2  1  0
  9 34  1  1
  6  5  1  0
  6  7  1  1
  9 16  1  0
  2  1  1  0
  9  8  1  0
 13 14  1  0
 18  6  1  0
 14 15  1  0
 16 13  2  0
  6  8  1  0
  4  3  1  0
  5  4  1  0
  3  2  1  0
 17 38  1  0
  8 32  1  0
  8 33  1  0
  5 27  1  0
  5 28  1  0
  2 22  1  1
  7 29  1  0
  7 30  1  0
  7 31  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
  4 25  1  0
  4 26  1  0
  3 23  1  0
  3 24  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(5R,8aR,9aS)-3-(hydroxymethyl)-5,8a-dimethyl-2H,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

Traditional Name

(5R,8aR,9aS)-3-(hydroxymethyl)-5,8a-dimethyl-5H,6H,7H,8H,9H,9aH-naphtho[2,3-b]furan-2-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C1=C2C([H])=C3[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])C([H])([H])[C@]2([H])OC1=O

InChI Identifier

InChI=1S/C15H20O3/c1-9-4-3-5-15(2)7-13-10(6-12(9)15)11(8-16)14(17)18-13/h6,9,13,16H,3-5,7-8H2,1-2H3/t9-,13+,15-/m1/s1

InChI Key

QBLRXHAPLQNELR-ZDBHGNHJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Inula helenium	LOTUS Database	35616633
Inula macrophylla	JEOL database	Fu, B., et al, Phytochemistry 58, 1121 (2001)
Inula racemosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
2-furanone
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
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	2.6	ALOGPS
logP	2	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.09	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.77 m³·mol⁻¹	ChemAxon
Polarizability	27.6 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

29420495

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12041559

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fu, B., et al. (2001). Fu, B., et al, Phytochemistry 58, 1121 (2001) . Phytochem..

Showing NP-Card for macrophyllilactone E (NP0031653)

MOL for NP0031653 (macrophyllilactone E)

3D MOL for NP0031653 (macrophyllilactone E)

3D SDF for NP0031653 (macrophyllilactone E)

3D-SDF for NP0031653 (macrophyllilactone E)

PDB for NP0031653 (macrophyllilactone E)

3D PDB for NP0031653 (macrophyllilactone E)

SMILES for NP0031653 (macrophyllilactone E)

INCHI for NP0031653 (macrophyllilactone E)

Structure for NP0031653 (macrophyllilactone E)

3D Structure for NP0031653 (macrophyllilactone E)