NP-MRD: Showing NP-Card for Bis-cephalezomine D (NP0069003)

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Record Information

Version

2.0

Created at

2022-04-28 14:16:42 UTC

Updated at

2022-04-28 14:16:42 UTC

NP-MRD ID

NP0069003

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bis-cephalezomine D

Description

(2S,3S,6S,8S)-8-[(2S,3S,6S,9S)-3-{[(2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)-4-methoxy-4-oxobutanoyl]oxy}-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]Icosa-1(20),4,13,15(19)-tetraen-9-yl]-4-methoxy-9-oxo-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]Icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl (2S,3S)-2,3-dihydroxy-3-(3-methylbutyl)butanedioate belongs to the class of organic compounds known as cephalotaxus alkaloids. These are alkaloids with a structure based on the cephalotaxine skeleton, a tetracyclic 1,3-benzodioxole-containing compound which arises from the skeletal rearrangement of the hydroaromatic component of the Erythrina group. Bis-cephalezomine D is found in Cephalotaxus harringtonia. Based on a literature review very few articles have been published on (2S,3S,6S,8S)-8-[(2S,3S,6S,9S)-3-{[(2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)-4-methoxy-4-oxobutanoyl]oxy}-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]Icosa-1(20),4,13,15(19)-tetraen-9-yl]-4-methoxy-9-oxo-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]Icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl (2S,3S)-2,3-dihydroxy-3-(3-methylbutyl)butanedioate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216162D          

 78 87  0  0  1  0            999 V2000
   -3.1311    2.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7302    3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9054    3.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4813    2.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8821    2.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7070    2.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5683    1.3009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7761    1.0705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1021    1.5463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0538    2.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6676    2.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5587    1.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3467    1.2965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2930    0.2712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4559    0.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688   -0.4028    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5937   -0.4140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0576    0.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8802    0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421   -0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2097    0.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8554   -0.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7335   -1.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9659   -1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3202   -1.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6063   -1.5025    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.5580   -2.3261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1959   -2.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0618   -3.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2898   -3.9541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6998   -4.1864    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.4675   -5.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9444   -6.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1303   -6.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3377   -4.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1097   -4.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6135   -5.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6438   -3.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1639   -1.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8121   -0.8354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0713   -0.1599    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8959   -0.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3305    0.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1551    0.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5897    1.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5451   -0.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0456   -0.9845    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7468   -1.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7211   -2.2437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4738   -1.0291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1751   -1.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3186   -1.3745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7569   -0.8256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5582   -1.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2922    4.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0403    3.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407    2.9165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 14 16  1  6  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 17  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 34 32  1  6  0  0  0
 34 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  1  0  0  0  0
 38 41  1  0  0  0  0
 34 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 34 47  1  1  0  0  0
 29 48  1  0  0  0  0
 48 49  1  0  0  0  0
 27 50  1  0  0  0  0
 50 51  1  0  0  0  0
 16 51  1  0  0  0  0
 23 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 22 54  1  0  0  0  0
  8 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
  7 57  1  0  0  0  0
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 59 60  2  0  0  0  0
 61 59  1  1  0  0  0
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  2 76  1  0  0  0  0
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 77 78  1  0  0  0  0
  1 78  1  0  0  0  0
M  END

     RDKit          3D

150159  0  0  0  0  0  0  0  0999 V2000
   10.5952    1.3089   -2.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2513   -2.8030   -1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1405   -3.1959    1.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1232   -1.2463    0.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5913    2.4362    1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4554    3.5248    1.8254 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4194    1.8350    0.7723 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1740    2.4843    0.9902 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4643    1.7193    2.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6797    1.9469    3.4372 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8611    0.1247   -0.7492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9485   -0.0668   -1.8026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1979    1.5843   -0.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1628    1.9832    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4066    3.4850    0.2922 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.9931    3.7950   -1.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0973   -0.6884   -1.0447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7010   -2.0626   -1.0749 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.2784    0.8457   -2.7028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8417    1.0676   -3.9849 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8394   -4.7282    1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6668   -4.8573    2.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873   -3.5554    2.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0311   -2.5549    1.9147 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200   -2.2994    1.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2906   -2.4924    1.5815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7396   -7.2450   -0.4344 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282216162D          

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   -1.7569   -0.8256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5582   -1.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2922    4.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0403    3.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9407    2.9165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 14 16  1  6  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 17  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 34 32  1  6  0  0  0
 34 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  1  0  0  0  0
 38 41  1  0  0  0  0
 34 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 34 47  1  1  0  0  0
 29 48  1  0  0  0  0
 48 49  1  0  0  0  0
 27 50  1  0  0  0  0
 50 51  1  0  0  0  0
 16 51  1  0  0  0  0
 23 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 22 54  1  0  0  0  0
  8 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
  7 57  1  0  0  0  0
 57 58  1  1  0  0  0
 58 59  1  0  0  0  0
 59 60  2  0  0  0  0
 61 59  1  1  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 64 66  1  0  0  0  0
 61 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  2  0  0  0  0
 68 70  1  0  0  0  0
 70 71  1  0  0  0  0
 67 72  1  6  0  0  0
 61 73  1  6  0  0  0
 56 74  1  0  0  0  0
 74 75  1  0  0  0  0
  2 76  1  0  0  0  0
 76 77  1  0  0  0  0
 77 78  1  0  0  0  0
  1 78  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069003

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@](O)(CCCC(C)(C)O)C(=O)O[C@H]1[C@H]2C3=CC4=C(OCO4)C=C3CCN3[C@@H](CC[C@@]23C=C1OC)[C@@H]1C[C@@]23C=C(OC)[C@@H](OC(=O)[C@](O)(CCC(C)C)[C@H](O)C(=O)OC)[C@H]2C2=CC4=C(OCO4)C=C2CCN3C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C57H72N2O19/c1-30(2)10-17-57(68,48(61)50(63)72-8)52(65)78-47-42(70-6)26-55-24-35(49(62)59(55)19-13-32-21-38-40(76-29-74-38)23-34(32)45(47)55)36-11-16-54-25-41(69-5)46(77-51(64)56(67,27-43(60)71-7)15-9-14-53(3,4)66)44(54)33-22-39-37(73-28-75-39)20-31(33)12-18-58(36)54/h20-23,25-26,30,35-36,44-48,61,66-68H,9-19,24,27-29H2,1-8H3/t35-,36-,44+,45+,46+,47+,48+,54+,55+,56+,57-/m0/s1

> <INCHI_KEY>
UMHJWPUXUGZLSA-XREGAUGTSA-N

> <FORMULA>
C57H72N2O19

> <MOLECULAR_WEIGHT>
1089.198

> <EXACT_MASS>
1088.472928106

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
150

> <JCHEM_AVERAGE_POLARIZABILITY>
114.0732157822134

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,6S,8S)-8-[(2S,3S,6S,9S)-3-{[(2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)-4-methoxy-4-oxobutanoyl]oxy}-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0^{2,6}.0^{6,10}.0^{15,19}]icosa-1(20),4,13,15(19)-tetraen-9-yl]-4-methoxy-9-oxo-16,18-dioxa-10-azapentacyclo[11.7.0.0^{2,6}.0^{6,10}.0^{15,19}]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl (2S,3S)-2,3-dihydroxy-3-(3-methylbutyl)butanedioate

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.5112999981872126

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.941974770016543

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.033954271218828

> <JCHEM_PKA_STRONGEST_BASIC>
10.289815688348039

> <JCHEM_POLAR_SURFACE_AREA>
265.04999999999995

> <JCHEM_REFRACTIVITY>
276.43450000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,6S,8S)-8-[(2S,3S,6S,9S)-3-{[(2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)-4-methoxy-4-oxobutanoyl]oxy}-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0^{2,6}.0^{6,10}.0^{15,19}]icosa-1(20),4,13,15(19)-tetraen-9-yl]-4-methoxy-9-oxo-16,18-dioxa-10-azapentacyclo[11.7.0.0^{2,6}.0^{6,10}.0^{15,19}]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl (2S,3S)-2,3-dihydroxy-3-(3-methylbutyl)butanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -5.845   5.148   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.096   6.494   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.557   6.519   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.765   5.198   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.513   3.852   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.053   3.827   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.927   2.428   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.449   1.998   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.191   2.886   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.100   4.424   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.246   5.453   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.043   1.964   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.514   2.420   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.547   0.506   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.851   0.693   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.435  -0.752   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.975  -0.773   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.841   0.501   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.376   0.618   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.425  -0.510   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.858   0.055   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.063  -0.904   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.836  -2.427   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.403  -2.992   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.198  -2.033   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.865  -2.805   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.431  -2.244   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.620  -3.577   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.285  -4.731   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.775  -4.342   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.966  -5.319   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.715  -6.838   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.274  -7.381   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.906  -7.815   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.930  -9.005   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.473 -10.446   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.496 -11.637   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.977 -11.387   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.457 -11.137   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       3.726 -12.906   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.227  -9.867   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.097  -8.791   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.538  -8.248   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       9.788  -6.729   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      10.729  -9.225   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      10.479 -10.744   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       7.883  -6.624   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       2.724  -6.166   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       1.202  -6.397   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       2.173  -3.132   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       0.939  -2.210   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      10.214  -3.114   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      11.293  -2.016   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      10.582  -0.650   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -1.401   0.459   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -2.850  -0.062   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -3.793   1.155   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      -5.333   1.107   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      -6.061  -0.250   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      -5.249  -1.559   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -7.600  -0.298   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -9.139  -0.347   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -9.950   0.962   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0     -11.490   0.914   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0     -12.301   2.223   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0     -12.218  -0.443   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      -7.552  -1.838   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      -8.861  -2.649   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      -8.813  -4.188   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0     -10.218  -1.921   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0     -11.527  -2.732   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0      -6.195  -2.566   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      -7.648   1.241   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      -3.280  -1.541   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0      -4.775  -1.908   0.000  0.00  0.00           C+0
HETATM   76  O   UNK     0      -6.145   7.622   0.000  0.00  0.00           O+0
HETATM   77  C   UNK     0      -7.542   6.973   0.000  0.00  0.00           C+0
HETATM   78  O   UNK     0      -7.356   5.444   0.000  0.00  0.00           O+0
CONECT    1    2    6   78                                                  
CONECT    2    1    3   76                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   57                                                  
CONECT    8    7    9   15   55                                             
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    4                                                       
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14    8                                                       
CONECT   16   14   17   51                                                  
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   54                                                  
CONECT   23   22   24   52                                                  
CONECT   24   23   25                                                       
CONECT   25   24   20   26                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   17   28   50                                             
CONECT   28   27   29                                                       
CONECT   29   28   30   48                                                  
CONECT   30   29   26   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   42   47                                             
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40   41                                             
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   38                                                            
CONECT   42   34   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45                                                            
CONECT   47   34                                                            
CONECT   48   29   49                                                       
CONECT   49   48                                                            
CONECT   50   27   51                                                       
CONECT   51   50   16                                                       
CONECT   52   23   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   22                                                       
CONECT   55    8   56                                                       
CONECT   56   55   57   74                                                  
CONECT   57   56    7   58                                                  
CONECT   58   57   59                                                       
CONECT   59   58   60   61                                                  
CONECT   60   59                                                            
CONECT   61   59   62   67   73                                             
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65   66                                                  
CONECT   65   64                                                            
CONECT   66   64                                                            
CONECT   67   61   68   72                                                  
CONECT   68   67   69   70                                                  
CONECT   69   68                                                            
CONECT   70   68   71                                                       
CONECT   71   70                                                            
CONECT   72   67                                                            
CONECT   73   61                                                            
CONECT   74   56   75                                                       
CONECT   75   74                                                            
CONECT   76    2   77                                                       
CONECT   77   76   78                                                       
CONECT   78   77    1                                                       
MASTER        0    0    0    0    0    0    0    0   78    0  174    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,6S,8S)-8-[(2S,3S,6S,9S)-3-{[(2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)-4-methoxy-4-oxobutanoyl]oxy}-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0,.0,.0,]icosa-1(20),4,13,15(19)-tetraen-9-yl]-4-methoxy-9-oxo-16,18-dioxa-10-azapentacyclo[11.7.0.0,.0,.0,]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl (2S,3S)-2,3-dihydroxy-3-(3-methylbutyl)butanedioic acid	Generator

Chemical Formula

C₅₇H₇₂N₂O₁₉

Average Mass

1089.1980 Da

Monoisotopic Mass

1088.47293 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@](O)(CCCC(C)(C)O)C(=O)O[C@H]1[C@H]2C3=CC4=C(OCO4)C=C3CCN3[C@@H](CC[C@@]23C=C1OC)[C@@H]1C[C@@]23C=C(OC)[C@@H](OC(=O)[C@](O)(CCC(C)C)[C@H](O)C(=O)OC)[C@H]2C2=CC4=C(OCO4)C=C2CCN3C1=O

InChI Identifier

InChI=1S/C57H72N2O19/c1-30(2)10-17-57(68,48(61)50(63)72-8)52(65)78-47-42(70-6)26-55-24-35(49(62)59(55)19-13-32-21-38-40(76-29-74-38)23-34(32)45(47)55)36-11-16-54-25-41(69-5)46(77-51(64)56(67,27-43(60)71-7)15-9-14-53(3,4)66)44(54)33-22-39-37(73-28-75-39)20-31(33)12-18-58(36)54/h20-23,25-26,30,35-36,44-48,61,66-68H,9-19,24,27-29H2,1-8H3/t35-,36-,44+,45+,46+,47+,48+,54+,55+,56+,57-/m0/s1

InChI Key

UMHJWPUXUGZLSA-XREGAUGTSA-N

Experimental Spectra

Not Available

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
Cephalotaxus harringtonia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cephalotaxus alkaloids. These are alkaloids with a structure based on the cephalotaxine skeleton, a tetracyclic 1,3-benzodioxole-containing compound which arises from the skeletal rearrangement of the hydroaromatic component of the Erythrina group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cephalotaxus alkaloids

Sub Class

Not Available

Direct Parent

Cephalotaxus alkaloids

Alternative Parents

Substituents

Cephalotaxine
Cephalotaxus alkaloid skeleton
Tetracarboxylic acid or derivatives
Benzazepine
Benzodioxole
Aralkylamine
Fatty acid methyl ester
Fatty acid ester
Beta-hydroxy acid
Azepine
Fatty acyl
Benzenoid
N-alkylpyrrolidine
2-pyrrolidone
Pyrrolidone
Monosaccharide
Hydroxy acid
Methyl ester
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Lactam
Carboxylic acid ester
Carboxamide group
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	3.09	ALOGPS
logP	2.51	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	11.03	ChemAxon
pKa (Strongest Basic)	10.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	265.05 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	276.43 m³·mol⁻¹	ChemAxon
Polarizability	114.07 Å³	ChemAxon
Number of Rings	10	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163031565

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Bis-cephalezomine D (NP0069003)

MOL for NP0069003 (Bis-cephalezomine D)

3D MOL for NP0069003 (Bis-cephalezomine D)

3D SDF for NP0069003 (Bis-cephalezomine D)

3D-SDF for NP0069003 (Bis-cephalezomine D)

PDB for NP0069003 (Bis-cephalezomine D)

3D PDB for NP0069003 (Bis-cephalezomine D)

SMILES for NP0069003 (Bis-cephalezomine D)

INCHI for NP0069003 (Bis-cephalezomine D)

Structure for NP0069003 (Bis-cephalezomine D)

3D Structure for NP0069003 (Bis-cephalezomine D)