NP-MRD: Showing NP-Card for Erlangerin B (NP0024649)

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Record Information

Version

2.0

Created at

2021-06-19 16:58:18 UTC

Updated at

2021-06-29 23:49:07 UTC

NP-MRD ID

NP0024649

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Erlangerin B

Provided By

JEOL Database JEOL Logo

Description

(3AR,4R,9aS)-4-(2H-1,3-benzodioxol-5-yl)-5,6,7-trimethoxy-3-oxo-1H,3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-3a-yl acetate belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. Erlangerin B is found in Commiphora erlangeriana. Erlangerin B was first documented in 2002 (PMID: 12350141). Based on a literature review very few articles have been published on (3aR,4R,9aS)-4-(2H-1,3-benzodioxol-5-yl)-5,6,7-trimethoxy-3-oxo-1H,3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-3a-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192118583D          

 57 61  0  0  0  0            999 V2000
   -2.3455    3.7141    3.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2571    2.8080    3.9212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9718    2.0232    2.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4819    2.2229    1.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1149    1.3833    0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784    0.2754    0.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2558    0.0903    1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1710   -0.9224    2.1655 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8012   -1.8419    3.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0632    0.9780    3.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4869    0.8033    4.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6948    1.5575    4.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0886   -0.6917   -0.4336 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.7152   -5.7127    1.1651 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306192118583D          

 57 61  0  0  0  0            999 V2000
   -2.3455    3.7141    3.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2571    2.8080    3.9212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9718    2.0232    2.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3499   -1.3290   -3.2576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184    0.9220   -2.8425 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6150    1.8591   -2.1173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7445    1.2031   -2.0028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6448    1.7020   -0.8878 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1033    4.5270    3.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5193    4.1577    4.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2642    3.1991    3.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1544    3.0515    1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460   -2.8356    2.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822   -1.8961    3.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3122   -1.5851    4.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095    1.3872    5.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5075    2.6312    4.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    1.2248    3.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1898   -0.6523   -0.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748   -2.9554   -0.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9813   -5.3252   -0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -1.7206    0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4838   -6.2145    0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7727   -6.0861    2.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5643   -3.1639   -3.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256   -1.8865   -3.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0881   -2.3332   -4.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024    2.0637   -1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5615    2.7953   -2.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    1.3943   -2.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388    1.2466   -0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708    2.7864   -0.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
  6 13  1  0  0  0  0
 11 12  1  0  0  0  0
 13 23  1  0  0  0  0
  7  8  1  0  0  0  0
 32 33  1  0  0  0  0
  8  9  1  0  0  0  0
 32 23  1  0  0  0  0
 28 29  2  0  0  0  0
  5  4  1  0  0  0  0
 13 14  1  0  0  0  0
  4  3  2  0  0  0  0
 14 15  2  0  0  0  0
  5  6  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
 18 17  1  0  0  0  0
 10  7  2  0  0  0  0
 23 28  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 22  1  0  0  0  0
 22 21  1  0  0  0  0
 21 20  1  0  0  0  0
 20 18  1  0  0  0  0
  7  6  1  0  0  0  0
 32 55  1  6  0  0  0
  3  2  1  0  0  0  0
 23 24  1  6  0  0  0
  3 10  1  0  0  0  0
 24 25  1  0  0  0  0
  2  1  1  0  0  0  0
 25 26  1  0  0  0  0
  5 33  1  0  0  0  0
 25 27  2  0  0  0  0
  4 37  1  0  0  0  0
 13 44  1  6  0  0  0
 33 56  1  0  0  0  0
 33 57  1  0  0  0  0
 31 53  1  0  0  0  0
 31 54  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
  9 40  1  0  0  0  0
 15 45  1  0  0  0  0
 16 46  1  0  0  0  0
 19 47  1  0  0  0  0
 21 48  1  0  0  0  0
 21 49  1  0  0  0  0
 26 50  1  0  0  0  0
 26 51  1  0  0  0  0
 26 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0024649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C2OC([H])([H])OC2=C([H])C(=C1[H])[C@]1([H])C2=C(C([H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C2OC([H])([H])[H])C([H])([H])[C@@]2([H])C([H])([H])OC(=O)[C@@]12OC(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O9/c1-12(25)33-24-15(10-30-23(24)26)7-14-9-18(27-2)21(28-3)22(29-4)19(14)20(24)13-5-6-16-17(8-13)32-11-31-16/h5-6,8-9,15,20H,7,10-11H2,1-4H3/t15-,20+,24-/m0/s1

> <INCHI_KEY>
SEMJADKBFZYYKQ-VNJOCVIMSA-N

> <FORMULA>
C24H24O9

> <MOLECULAR_WEIGHT>
456.447

> <EXACT_MASS>
456.142032353

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
45.45600793584181

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4R,9aS)-4-(2H-1,3-benzodioxol-5-yl)-5,6,7-trimethoxy-3-oxo-1H,3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-3a-yl acetate

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
2.469355893666666

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.270496802759275

> <JCHEM_POLAR_SURFACE_AREA>
98.75000000000001

> <JCHEM_REFRACTIVITY>
113.018

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4R,9aS)-4-(2H-1,3-benzodioxol-5-yl)-5,6,7-trimethoxy-3-oxo-1H,4H,9H,9aH-naphtho[2,3-c]furan-3a-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 61  0  0  0  0  0  0  0  0999 V2000
   -2.3455    3.7141    3.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2571    2.8080    3.9212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9718    2.0232    2.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4819    2.2229    1.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1149    1.3833    0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784    0.2754    0.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2558    0.0903    1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1710   -0.9224    2.1655 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8012   -1.8419    3.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0632    0.9780    3.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4869    0.8033    4.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6948    1.5575    4.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0886   -0.6917   -0.4336 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2964   -2.1507   -0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6090   -3.1900   -0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2876   -4.5305   -0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9413   -4.8072    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341   -3.8110    0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5476   -2.4805    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9890   -4.2961    1.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7152   -5.7127    1.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4198   -6.0451    0.6252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3938   -0.2726   -1.8783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5131   -1.0858   -2.2716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392   -1.1690   -3.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9009   -2.2063   -3.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3679   -0.4793   -4.4777 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8610   -0.3286   -2.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499   -1.3290   -3.2576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184    0.9220   -2.8425 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6150    1.8591   -2.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7445    1.2031   -2.0028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6448    1.7020   -0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1033    4.5270    3.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5193    4.1577    4.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2642    3.1991    3.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1544    3.0515    1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460   -2.8356    2.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822   -1.8961    3.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3122   -1.5851    4.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095    1.3872    5.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5075    2.6312    4.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    1.2248    3.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1898   -0.6523   -0.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748   -2.9554   -0.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9813   -5.3252   -0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -1.7206    0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4838   -6.2145    0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7727   -6.0861    2.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5643   -3.1639   -3.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256   -1.8865   -3.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0881   -2.3332   -4.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024    2.0637   -1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5615    2.7953   -2.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    1.3943   -2.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388    1.2466   -0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708    2.7864   -0.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  6 13  1  0
 11 12  1  0
 13 23  1  0
  7  8  1  0
 32 33  1  0
  8  9  1  0
 32 23  1  0
 28 29  2  0
  5  4  1  0
 13 14  1  0
  4  3  2  0
 14 15  2  0
  5  6  2  0
 15 16  1  0
 16 17  2  0
 18 19  2  0
 19 14  1  0
 18 17  1  0
 10  7  2  0
 23 28  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 17 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
  7  6  1  0
 32 55  1  6
  3  2  1  0
 23 24  1  6
  3 10  1  0
 24 25  1  0
  2  1  1  0
 25 26  1  0
  5 33  1  0
 25 27  2  0
  4 37  1  0
 13 44  1  6
 33 56  1  0
 33 57  1  0
 31 53  1  0
 31 54  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
 15 45  1  0
 16 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.345   3.714   3.804  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.257   2.808   3.921  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.972   2.023   2.835  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.482   2.223   1.552  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.115   1.383   0.482  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.278   0.275   0.704  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.256   0.090   1.999  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.171  -0.922   2.166  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.801  -1.842   3.195  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.063   0.978   3.041  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.487   0.803   4.290  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.695   1.558   4.394  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.089  -0.692  -0.434  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.296  -2.151  -0.135  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.609  -3.190  -0.462  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.288  -4.531  -0.226  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.941  -4.807   0.329  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.834  -3.811   0.643  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.548  -2.481   0.422  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.989  -4.296   1.173  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.715  -5.713   1.165  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.420  -6.045   0.625  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.394  -0.273  -1.878  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.513  -1.086  -2.272  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.839  -1.169  -3.587  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.901  -2.206  -3.785  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.368  -0.479  -4.478  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.861  -0.329  -2.756  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.350  -1.329  -3.258  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.418   0.922  -2.842  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.615   1.859  -2.117  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.745   1.203  -2.003  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.645   1.702  -0.888  0.00  0.00           C+0
HETATM   34  H   UNK     0      -2.103   4.527   3.111  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.519   4.158   4.789  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.264   3.199   3.503  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.154   3.051   1.348  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.146  -2.836   2.893  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.282  -1.896   3.353  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.312  -1.585   4.128  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.110   1.387   5.391  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.508   2.631   4.284  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.436   1.225   3.659  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.190  -0.652  -0.430  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.575  -2.955  -0.909  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.981  -5.325  -0.476  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.279  -1.721   0.675  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.484  -6.215   0.566  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.773  -6.086   2.194  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.564  -3.164  -3.379  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.826  -1.887  -3.299  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.088  -2.333  -4.855  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.102   2.064  -1.159  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.562   2.795  -2.682  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.278   1.394  -2.943  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.639   1.247  -0.981  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.771   2.786  -0.998  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    3    1                                                       
CONECT    3    4    2   10                                                  
CONECT    4    5    3   37                                                  
CONECT    5    4    6   33                                                  
CONECT    6   13    5    7                                                  
CONECT    7    8   10    6                                                  
CONECT    8    7    9                                                       
CONECT    9    8   38   39   40                                             
CONECT   10   11    7    3                                                  
CONECT   11   10   12                                                       
CONECT   12   11   41   42   43                                             
CONECT   13    6   23   14   44                                             
CONECT   14   13   15   19                                                  
CONECT   15   14   16   45                                                  
CONECT   16   15   17   46                                                  
CONECT   17   16   18   22                                                  
CONECT   18   19   17   20                                                  
CONECT   19   18   14   47                                                  
CONECT   20   21   18                                                       
CONECT   21   22   20   48   49                                             
CONECT   22   17   21                                                       
CONECT   23   13   32   28   24                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   50   51   52                                             
CONECT   27   25                                                            
CONECT   28   29   23   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   53   54                                             
CONECT   32   33   23   31   55                                             
CONECT   33   32    5   56   57                                             
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    4                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   19                                                            
CONECT   48   21                                                            
CONECT   49   21                                                            
CONECT   50   26                                                            
CONECT   51   26                                                            
CONECT   52   26                                                            
CONECT   53   31                                                            
CONECT   54   31                                                            
CONECT   55   32                                                            
CONECT   56   33                                                            
CONECT   57   33                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  122    0
END

RDKit          3D

57 61  0  0  0  0  0  0  0  0999 V2000
   -2.3455    3.7141    3.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2571    2.8080    3.9212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9718    2.0232    2.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4819    2.2229    1.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1149    1.3833    0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2784    0.2754    0.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2558    0.0903    1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1710   -0.9224    2.1655 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8012   -1.8419    3.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0632    0.9780    3.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4869    0.8033    4.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6948    1.5575    4.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0886   -0.6917   -0.4336 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2964   -2.1507   -0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6090   -3.1900   -0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2876   -4.5305   -0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9413   -4.8072    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341   -3.8110    0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5476   -2.4805    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9890   -4.2961    1.1726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7152   -5.7127    1.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4198   -6.0451    0.6252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3938   -0.2726   -1.8783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5131   -1.0858   -2.2716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392   -1.1690   -3.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9009   -2.2063   -3.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3679   -0.4793   -4.4777 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8610   -0.3286   -2.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499   -1.3290   -3.2576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184    0.9220   -2.8425 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6150    1.8591   -2.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7445    1.2031   -2.0028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6448    1.7020   -0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1033    4.5270    3.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5193    4.1577    4.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2642    3.1991    3.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1544    3.0515    1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1460   -2.8356    2.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822   -1.8961    3.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3122   -1.5851    4.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095    1.3872    5.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5075    2.6312    4.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    1.2248    3.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1898   -0.6523   -0.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748   -2.9554   -0.9086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9813   -5.3252   -0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -1.7206    0.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4838   -6.2145    0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7727   -6.0861    2.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5643   -3.1639   -3.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8256   -1.8865   -3.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0881   -2.3332   -4.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024    2.0637   -1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5615    2.7953   -2.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    1.3943   -2.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388    1.2466   -0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708    2.7864   -0.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  6 13  1  0
 11 12  1  0
 13 23  1  0
  7  8  1  0
 32 33  1  0
  8  9  1  0
 32 23  1  0
 28 29  2  0
  5  4  1  0
 13 14  1  0
  4  3  2  0
 14 15  2  0
  5  6  2  0
 15 16  1  0
 16 17  2  0
 18 19  2  0
 19 14  1  0
 18 17  1  0
 10  7  2  0
 23 28  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 17 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
  7  6  1  0
 32 55  1  6
  3  2  1  0
 23 24  1  6
  3 10  1  0
 24 25  1  0
  2  1  1  0
 25 26  1  0
  5 33  1  0
 25 27  2  0
  4 37  1  0
 13 44  1  6
 33 56  1  0
 33 57  1  0
 31 53  1  0
 31 54  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
 15 45  1  0
 16 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(3AR,4R,9as)-4-(2H-1,3-benzodioxol-5-yl)-5,6,7-trimethoxy-3-oxo-1H,3H,3ah,4H,9H,9ah-naphtho[2,3-c]furan-3a-yl acetic acid	Generator

Chemical Formula

C₂₄H₂₄O₉

Average Mass

456.4470 Da

Monoisotopic Mass

456.14203 Da

IUPAC Name

(3aR,4R,9aS)-4-(2H-1,3-benzodioxol-5-yl)-5,6,7-trimethoxy-3-oxo-1H,3H,3aH,4H,9H,9aH-naphtho[2,3-c]furan-3a-yl acetate

Traditional Name

(3aR,4R,9aS)-4-(2H-1,3-benzodioxol-5-yl)-5,6,7-trimethoxy-3-oxo-1H,4H,9H,9aH-naphtho[2,3-c]furan-3a-yl acetate

CAS Registry Number

Not Available

SMILES

[H]C1=C2OC([H])([H])OC2=C([H])C(=C1[H])[C@]1([H])C2=C(C([H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C2OC([H])([H])[H])C([H])([H])[C@@]2([H])C([H])([H])OC(=O)[C@@]12OC(=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C24H24O9/c1-12(25)33-24-15(10-30-23(24)26)7-14-9-18(27-2)21(28-3)22(29-4)19(14)20(24)13-5-6-16-17(8-13)32-11-31-16/h5-6,8-9,15,20H,7,10-11H2,1-4H3/t15-,20+,24-/m0/s1

InChI Key

SEMJADKBFZYYKQ-VNJOCVIMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Commiphora erlangeriana	JEOL database	Dekebo, A., et al, J. Nat. Prod. 65, 1252 (2002)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Not Available

Direct Parent

Lignan lactones

Alternative Parents

Substituents

Lignan lactone
1-aryltetralin lignan
Naphthofuran
Tetralin
Benzodioxole
Anisole
Alkyl aryl ether
Dicarboxylic acid or derivatives
Gamma butyrolactone
Benzenoid
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Acetal
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	3.17	ALOGPS
logP	2.47	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	98.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	113.02 m³·mol⁻¹	ChemAxon
Polarizability	45.46 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

552666

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636994

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dekebo A, Lang M, Polborn K, Dagne E, Steglich W: Four lignans from Commiphora erlangeriana. J Nat Prod. 2002 Sep;65(9):1252-7. doi: 10.1021/np020028j. [PubMed:12350141 ]
Dekebo, A., et al. (2002). Dekebo, A., et al, J. Nat. Prod. 65, 1252 (2002). J. Nat. Prod..

Showing NP-Card for Erlangerin B (NP0024649)

MOL for NP0024649 (Erlangerin B)

3D MOL for NP0024649 (Erlangerin B)

3D SDF for NP0024649 (Erlangerin B)

3D-SDF for NP0024649 (Erlangerin B)

PDB for NP0024649 (Erlangerin B)

3D PDB for NP0024649 (Erlangerin B)

SMILES for NP0024649 (Erlangerin B)

INCHI for NP0024649 (Erlangerin B)

Structure for NP0024649 (Erlangerin B)

3D Structure for NP0024649 (Erlangerin B)