NP-MRD: Showing NP-Card for Duclauxin (NP0021495)

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Record Information

Version

1.0

Created at

2021-01-06 06:46:35 UTC

Updated at

2024-04-19 09:45:40 UTC

NP-MRD ID

NP0021495

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Duclauxin

Provided By

NPAtlas

Description

Duclauxin belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. Duclauxin is found in Penicillium, Penicillium herquei, Talaromyces bacillisporus, Talaromyces emodensis and Talaromyces stipitatus. It was first documented in 1974 (PMID: 4856962). Based on a literature review a significant number of articles have been published on Duclauxin (PMID: 31480659) (PMID: 32492551) (PMID: 32119543) (PMID: 29741874).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105163D          

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M  END

     RDKit          3D

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  Mrv1652306242105163D          

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   -1.6285    0.5797    0.3424 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5029    1.3380    1.2635 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6130    0.6380    1.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2586   -0.3755    1.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4008   -0.7125    1.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5211   -1.0082   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540   -2.0632   -0.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2867   -2.5556   -0.5648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2865   -2.6502   -1.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0305   -2.1792   -2.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1675   -2.7620   -3.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -1.1311   -1.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2452   -0.5531   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1442   -0.5899   -1.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880   -1.3224   -2.1936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1555    0.7974   -1.1489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1330    1.5055   -0.7930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8939    2.7607   -0.2376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5173    3.9239   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885    5.2093   -0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3341    3.8736   -1.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6017    3.2131    2.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4867    1.6524    2.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7863    1.7935    2.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8144    2.6168    0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1245    2.0870   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4936    2.5364   -0.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3123    0.2885   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4646   -1.7540   -0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -3.9678    1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3623    0.4079    2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9060    1.7813    2.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8870    2.2362    0.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9760   -2.3276    0.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7001   -3.4571   -2.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8042   -1.9698   -3.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8026   -3.4896   -3.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260   -3.3542   -2.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7544    1.3526   -1.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8657    1.5142   -1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444    5.6200    0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079    5.0714    0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942    5.8872   -0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 19  3  1  0  0  0  0
 32 20  1  0  0  0  0
 35  3  1  0  0  0  0
 16  4  1  0  0  0  0
 36 20  1  0  0  0  0
 16 10  2  0  0  0  0
 32 25  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  1 43  1  0  0  0  0
  6 44  1  0  0  0  0
  6 45  1  0  0  0  0
  6 46  1  0  0  0  0
  7 47  1  0  0  0  0
  9 48  1  0  0  0  0
 14 49  1  0  0  0  0
 19 50  1  1  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
 27 53  1  0  0  0  0
 28 54  1  0  0  0  0
 30 55  1  0  0  0  0
 30 56  1  0  0  0  0
 30 57  1  0  0  0  0
 35 58  1  6  0  0  0
 36 59  1  6  0  0  0
 39 60  1  0  0  0  0
 39 61  1  0  0  0  0
 39 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021495

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C2C3=C1C(=O)OC([H])=C3C(=O)[C@@]1([H])[C@]2(OC([H])([H])[H])[C@@]2([H])C(=O)C3=C4C(C(=O)OC([H])([H])[C@@]14[C@@]2([H])OC(=O)C([H])([H])[H])=C(O[H])C([H])=C3C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C29H22O11/c1-9-5-14(32)18-20-15(9)23(34)21-25(40-11(3)30)28(20,8-39-27(18)36)24-22(33)12-7-38-26(35)17-13(31)6-10(2)19(16(12)17)29(21,24)37-4/h5-7,21,24-25,31-32H,8H2,1-4H3/t21-,24+,25-,28-,29+/m0/s1

> <INCHI_KEY>
WBQDAYWQELBEPU-UHFFFAOYSA-N

> <FORMULA>
C29H22O11

> <MOLECULAR_WEIGHT>
546.484

> <EXACT_MASS>
546.116211528

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
51.84074123220203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,13S,14S,24S)-9,19-dihydroxy-13-methoxy-11,17-dimethyl-3,7,15,21-tetraoxo-6,22-dioxaheptacyclo[12.9.1.1^{1,16}.1^{4,8}.0^{2,13}.0^{12,26}.0^{20,25}]hexacosa-4,8(26),9,11,16(25),17,19-heptaen-24-yl acetate

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
3.638080272333333

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.111553983413136

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.989877736572929

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1856419493741335

> <JCHEM_POLAR_SURFACE_AREA>
162.73000000000002

> <JCHEM_REFRACTIVITY>
135.40799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,13S,14S,24S)-9,19-dihydroxy-13-methoxy-11,17-dimethyl-3,7,15,21-tetraoxo-6,22-dioxaheptacyclo[12.9.1.1^{1,16}.1^{4,8}.0^{2,13}.0^{12,26}.0^{20,25}]hexacosa-4,8(26),9,11,16(25),17,19-heptaen-24-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 68  0  0  0  0  0  0  0  0999 V2000
    1.4835    2.0958    1.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    2.0150    0.7323 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0451   -0.0404    0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2110    0.5932   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3549    1.9996   -0.5572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -0.1792   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4388   -1.4976    0.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6166   -2.2323    0.0114 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2892   -2.1271    0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386   -3.4594    0.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4113   -4.0978    0.7275 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2490   -4.0735    1.1760 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -3.4132    1.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9962   -2.0901    0.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003   -1.3878    0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2570   -1.3815    1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3134   -2.0299    1.1878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    0.1092    1.0246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6285    0.5797    0.3424 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5029    1.3380    1.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6130    0.6380    1.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2586   -0.3755    1.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4008   -0.7125    1.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5211   -1.0082   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540   -2.0632   -0.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2867   -2.5556   -0.5648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2865   -2.6502   -1.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0305   -2.1792   -2.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1675   -2.7620   -3.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -1.1311   -1.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2452   -0.5531   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1442   -0.5899   -1.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880   -1.3224   -2.1936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1555    0.7974   -1.1489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1330    1.5055   -0.7930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8939    2.7607   -0.2376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5173    3.9239   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885    5.2093   -0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3341    3.8736   -1.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6017    3.2131    2.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4867    1.6524    2.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7863    1.7935    2.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8144    2.6168    0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1245    2.0870   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4936    2.5364   -0.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3123    0.2885   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4646   -1.7540   -0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -3.9678    1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3623    0.4079    2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9060    1.7813    2.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8870    2.2362    0.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9760   -2.3276    0.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7001   -3.4571   -2.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8042   -1.9698   -3.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8026   -3.4896   -3.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260   -3.3542   -2.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7544    1.3526   -1.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8657    1.5142   -1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444    5.6200    0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079    5.0714    0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942    5.8872   -0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  1
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 38 40  2  0
 19  3  1  0
 32 20  1  0
 35  3  1  0
 16  4  1  0
 36 20  1  0
 16 10  2  0
 32 25  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  6 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  9 48  1  0
 14 49  1  0
 19 50  1  1
 21 51  1  0
 21 52  1  0
 27 53  1  0
 28 54  1  0
 30 55  1  0
 30 56  1  0
 30 57  1  0
 35 58  1  6
 36 59  1  6
 39 60  1  0
 39 61  1  0
 39 62  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       1.484   2.096   1.996  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.978   2.015   0.732  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.790   0.735   0.250  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.045  -0.040   0.211  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.211   0.593  -0.188  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.355   2.000  -0.557  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.385  -0.179  -0.241  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.439  -1.498   0.075  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.617  -2.232   0.011  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.289  -2.127   0.471  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.339  -3.459   0.793  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.411  -4.098   0.728  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.249  -4.074   1.176  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.096  -3.413   1.254  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.996  -2.090   0.944  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.100  -1.388   0.535  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.257  -1.381   1.057  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.313  -2.030   1.188  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.335   0.109   1.025  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.629   0.580   0.342  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.503   1.338   1.264  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.613   0.638   1.678  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.259  -0.376   1.020  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.401  -0.713   1.357  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.521  -1.008  -0.074  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.054  -2.063  -0.800  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.287  -2.556  -0.565  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.287  -2.650  -1.824  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.030  -2.179  -2.093  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.167  -2.762  -3.168  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.499  -1.131  -1.373  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.245  -0.553  -0.372  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.144  -0.590  -1.613  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.688  -1.322  -2.194  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.156   0.797  -1.149  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.133   1.506  -0.793  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.894   2.761  -0.238  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.517   3.924  -0.673  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.188   5.209  -0.011  0.00  0.00           C+0
HETATM   40  O   UNK     0      -2.334   3.874  -1.604  0.00  0.00           O+0
HETATM   41  H   UNK     0       1.602   3.213   2.202  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.487   1.652   2.138  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.786   1.794   2.818  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.814   2.617   0.264  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.125   2.087  -1.385  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.494   2.536  -0.913  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.312   0.289  -0.550  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.465  -1.754  -0.284  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.222  -3.968   1.576  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.362   0.408   2.103  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.906   1.781   2.093  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.887   2.236   0.687  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.976  -2.328   0.060  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.700  -3.457  -2.376  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.804  -1.970  -3.871  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.803  -3.490  -3.715  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.326  -3.354  -2.746  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.754   1.353  -1.878  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.866   1.514  -1.615  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.144   5.620   0.387  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.508   5.071   0.832  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.794   5.887  -0.795  0.00  0.00           H+0
CONECT    1    2   41   42   43                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   19   35                                             
CONECT    4    3    5   16                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   44   45   46                                             
CONECT    7    5    8   47                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   48                                                       
CONECT   10    8   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   49                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15    4   10                                                  
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20    3   50                                             
CONECT   20   19   21   32   36                                             
CONECT   21   20   22   51   52                                             
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   32                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   53                                                       
CONECT   28   26   29   54                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   55   56   57                                             
CONECT   31   29   32   33                                                  
CONECT   32   31   20   25                                                  
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36    3   58                                             
CONECT   36   35   37   20   59                                             
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38   60   61   62                                             
CONECT   40   38                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    6                                                            
CONECT   45    6                                                            
CONECT   46    6                                                            
CONECT   47    7                                                            
CONECT   48    9                                                            
CONECT   49   14                                                            
CONECT   50   19                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   27                                                            
CONECT   54   28                                                            
CONECT   55   30                                                            
CONECT   56   30                                                            
CONECT   57   30                                                            
CONECT   58   35                                                            
CONECT   59   36                                                            
CONECT   60   39                                                            
CONECT   61   39                                                            
CONECT   62   39                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  136    0
END

RDKit          3D

62 68  0  0  0  0  0  0  0  0999 V2000
    1.4835    2.0958    1.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    2.0150    0.7323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7897    0.7353    0.2502 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0451   -0.0404    0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2110    0.5932   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3549    1.9996   -0.5572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -0.1792   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4388   -1.4976    0.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6166   -2.2323    0.0114 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2892   -2.1271    0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386   -3.4594    0.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4113   -4.0978    0.7275 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2490   -4.0735    1.1760 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -3.4132    1.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9962   -2.0901    0.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003   -1.3878    0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2570   -1.3815    1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3134   -2.0299    1.1878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    0.1092    1.0246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6285    0.5797    0.3424 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5029    1.3380    1.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6130    0.6380    1.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2586   -0.3755    1.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4008   -0.7125    1.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5211   -1.0082   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540   -2.0632   -0.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2867   -2.5556   -0.5648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2865   -2.6502   -1.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0305   -2.1792   -2.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1675   -2.7620   -3.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -1.1311   -1.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2452   -0.5531   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1442   -0.5899   -1.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6880   -1.3224   -2.1936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1555    0.7974   -1.1489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1330    1.5055   -0.7930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8939    2.7607   -0.2376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5173    3.9239   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885    5.2093   -0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3341    3.8736   -1.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6017    3.2131    2.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4867    1.6524    2.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7863    1.7935    2.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8144    2.6168    0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1245    2.0870   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4936    2.5364   -0.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3123    0.2885   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4646   -1.7540   -0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -3.9678    1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3623    0.4079    2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9060    1.7813    2.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8870    2.2362    0.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9760   -2.3276    0.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7001   -3.4571   -2.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8042   -1.9698   -3.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8026   -3.4896   -3.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260   -3.3542   -2.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7544    1.3526   -1.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8657    1.5142   -1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444    5.6200    0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079    5.0714    0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942    5.8872   -0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  1
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 38 40  2  0
 19  3  1  0
 32 20  1  0
 35  3  1  0
 16  4  1  0
 36 20  1  0
 16 10  2  0
 32 25  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  6 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  9 48  1  0
 14 49  1  0
 19 50  1  1
 21 51  1  0
 21 52  1  0
 27 53  1  0
 28 54  1  0
 30 55  1  0
 30 56  1  0
 30 57  1  0
 35 58  1  6
 36 59  1  6
 39 60  1  0
 39 61  1  0
 39 62  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
9,19-Dihydroxy-13-methoxy-11,17-dimethyl-3,7,15,21-tetraoxo-6,22-dioxaheptacyclo[12.9.1.1¹,¹⁶.1⁴,⁸.0²,¹³.0¹²,²⁶.0²⁰,²⁵]hexacosa-4,8,10,12(26),16(25),17,19-heptaen-24-yl acetic acid	Generator
9,19-Dihydroxy-13-methoxy-11,17-dimethyl-3,7,15,21-tetraoxo-6,22-dioxaheptacyclo[12.9.1.1,.1,.0,.0,.0,]hexacosa-4,8,10,12(26),16(25),17,19-heptaen-24-yl acetic acid	Generator

Chemical Formula

C₂₉H₂₂O₁₁

Average Mass

546.4840 Da

Monoisotopic Mass

546.11621 Da

IUPAC Name

(1R,2R,13S,14S,24S)-9,19-dihydroxy-13-methoxy-11,17-dimethyl-3,7,15,21-tetraoxo-6,22-dioxaheptacyclo[12.9.1.1^{1,16}.1^{4,8}.0^{2,13}.0^{12,26}.0^{20,25}]hexacosa-4,8(26),9,11,16(25),17,19-heptaen-24-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC12C3C(OC(C)=O)C4(COC(=O)C5=C(O)C=C(C)C(C3=O)=C45)C1C(=O)C1=COC(=O)C3=C(O)C=C(C)C2=C13

InChI Identifier

InChI=1S/C29H22O11/c1-9-5-14(32)18-20-15(9)23(34)21-25(40-11(3)30)28(20,8-39-27(18)36)24-22(33)12-7-38-26(35)17-13(31)6-10(2)19(16(12)17)29(21,24)37-4/h5-7,21,24-25,31-32H,8H2,1-4H3

InChI Key

WBQDAYWQELBEPU-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2023-03-17	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2023-03-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2023-03-17	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2023-03-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2023-03-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2023-03-17	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2023-03-17	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	taizong.wu@uq.edu.au	Not Available	Not Available	2023-03-17	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Penicillium	NPAtlas	4856962
Penicillium herquei	LOTUS Database	35616633
Talaromyces bacillisporus	LOTUS Database	35616633
Talaromyces emodensis	LOTUS Database	35616633
Talaromyces stipitatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isocoumarins and derivatives

Sub Class

Not Available

Direct Parent

Isocoumarins and derivatives

Alternative Parents

Substituents

Isocoumarin
Benzopyran
Isochromane
Tetralin
2-benzopyran
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Dicarboxylic acid or derivatives
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
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	2.75	ALOGPS
logP	3.64	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.99	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	162.73 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	135.41 m³·mol⁻¹	ChemAxon
Polarizability	51.84 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA010037

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4526566

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Duclauxin

METLIN ID

Not Available

PubChem Compound

5377538

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang M, Yang L, Feng L, Hu F, Zhang F, Ren J, Qiu Y, Wang Z: Verruculosins A-B, New Oligophenalenone Dimers from the Soft Coral-Derived Fungus Talaromyces verruculosus. Mar Drugs. 2019 Sep 2;17(9). pii: md17090516. doi: 10.3390/md17090516. [PubMed:31480659 ]
Fuska J, Kuhr I, Nemec P, Fuskova A: Antitumor antibiotics produced by Penicillium stipitatum Thom. J Antibiot (Tokyo). 1974 Feb;27(2):123-7. doi: 10.7164/antibiotics.27.123. [PubMed:4856962 ]
Jimenez-Arreola BS, Aguilar-Ramirez E, Cano-Sanchez P, Morales-Jimenez J, Gonzalez-Andrade M, Medina-Franco JL, Rivera-Chavez J: Dimeric phenalenones from Talaromyces sp. (IQ-313) inhibit hPTP1B1-400: Insights into mechanistic kinetics from in vitro and in silico studies. Bioorg Chem. 2020 Aug;101:103893. doi: 10.1016/j.bioorg.2020.103893. Epub 2020 May 4. [PubMed:32492551 ]
Chaudhary NK, Crombie A, Vuong D, Lacey E, Piggott AM, Karuso P: Talauxins: Hybrid Phenalenone Dimers from Talaromyces stipitatus. J Nat Prod. 2020 Apr 24;83(4):1051-1060. doi: 10.1021/acs.jnatprod.9b01066. Epub 2020 Mar 2. [PubMed:32119543 ]
Gao SS, Zhang T, Garcia-Borras M, Hung YS, Billingsley JM, Houk KN, Hu Y, Tang Y: Biosynthesis of Heptacyclic Duclauxins Requires Extensive Redox Modifications of the Phenalenone Aromatic Polyketide. J Am Chem Soc. 2018 Jun 6;140(22):6991-6997. doi: 10.1021/jacs.8b03705. Epub 2018 May 24. [PubMed:29741874 ]

Showing NP-Card for Duclauxin (NP0021495)

MOL for NP0021495 (Duclauxin)

3D MOL for NP0021495 (Duclauxin)

3D SDF for NP0021495 (Duclauxin)

3D-SDF for NP0021495 (Duclauxin)

PDB for NP0021495 (Duclauxin)

3D PDB for NP0021495 (Duclauxin)

SMILES for NP0021495 (Duclauxin)

INCHI for NP0021495 (Duclauxin)

Structure for NP0021495 (Duclauxin)

3D Structure for NP0021495 (Duclauxin)