NP-MRD: Showing NP-Card for (3as,4s,4ar,6s,8s,8as,9r,10r)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2e)-3-phenylprop-2-enoyl]oxy}-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-10-yl benzoate (NP0273476)

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Record Information

Version

2.0

Created at

2022-09-08 20:32:09 UTC

Updated at

2022-09-08 20:32:09 UTC

NP-MRD ID

NP0273476

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,4s,4ar,6s,8s,8as,9r,10r)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2e)-3-phenylprop-2-enoyl]oxy}-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-10-yl benzoate

Description

(3AS,4S,4aR,6S,8S,8aS,9R,10R)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2E)-3-phenylprop-2-enoyl]oxy}-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-10-yl benzoate belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system. Based on a literature review very few articles have been published on (3aS,4S,4aR,6S,8S,8aS,9R,10R)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2E)-3-phenylprop-2-enoyl]oxy}-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-10-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082222322D          

 54 58  0  0  1  0            999 V2000
    3.7448    0.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194    0.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050    1.2468    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3160    0.6924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795    2.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685    2.6074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4431    3.4137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2287    3.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4033    4.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8397    3.1114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829    2.3555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7173    3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084    1.5491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5691    1.1829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5783    0.3580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2974   -0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3066   -0.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1188   -0.1236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9143   -0.1149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1734    3.4902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2427    4.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8387    4.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1883    5.1656    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  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13  2  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 25 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 19 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
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 40 50  1  0  0  0  0
 11 50  1  0  0  0  0
 50 51  1  6  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  2  0  0  0  0
M  END

     RDKit          3D

102106  0  0  0  0  0  0  0  0999 V2000
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   -4.6220    6.1033   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3389    4.0205   -0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8430    0.0959   -0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0003   -0.1152    3.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3655   -0.5504    2.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9661    1.1644    2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  0
  2  1  2  3
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 14 19  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 25 37  1  0
 37 38  1  0
 37 39  2  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  2  0
 42 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 47 48  1  0
 48 49  2  0
 40 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  1  0
 52 54  2  0
 50 11  1  0
 11 12  1  6
 19 20  1  6
 20 21  1  0
 20 22  1  0
 20 23  1  0
 11  6  1  0
 11 13  1  0
 39 19  1  0
 49 44  1  0
 36 31  1  0
  9 62  1  0
  9 63  1  0
  9 64  1  0
  6 61  1  1
  5 59  1  0
  5 60  1  0
  3 57  1  1
  4 58  1  0
  1 55  1  0
  1 56  1  0
 13 68  1  1
 14 69  1  6
 17 70  1  0
 17 71  1  0
 17 72  1  0
 24 80  1  0
 24 81  1  0
 25 82  1  6
 29 83  1  0
 30 84  1  0
 32 85  1  0
 33 86  1  0
 34 87  1  0
 35 88  1  0
 36 89  1  0
 38 90  1  0
 38 91  1  0
 38 92  1  0
 40 93  1  1
 45 94  1  0
 46 95  1  0
 47 96  1  0
 48 97  1  0
 49 98  1  0
 50 99  1  6
 53100  1  0
 53101  1  0
 53102  1  0
 12 65  1  0
 12 66  1  0
 12 67  1  0
 21 73  1  0
 21 74  1  0
 21 75  1  0
 22 76  1  0
 22 77  1  0
 22 78  1  0
 23 79  1  0
M  END


  Mrv1652309082222322D          

 54 58  0  0  1  0            999 V2000
    3.7448    0.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194    0.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050    1.2468    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3160    0.6924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795    2.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685    2.6074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4431    3.4137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2287    3.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4033    4.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8397    3.1114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829    2.3555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7173    3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084    1.5491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5691    1.1829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5783    0.3580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2974   -0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3066   -0.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1188   -0.1236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219    1.5325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8681    0.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0444    0.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3896    0.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143   -0.1149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184    1.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    1.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3111    1.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8790    2.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6446    2.8342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6812    1.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9155    1.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    0.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9521    0.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7543   -0.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3222    0.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0878    1.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2856    1.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8068    2.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758    3.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6293    2.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1364    2.9855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7702    3.7247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9469    3.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1734    3.4902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806    4.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427    4.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6089    5.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1519    5.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6715    5.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0377    5.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9614    2.9947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3110    3.7419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8387    4.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    4.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1883    5.1656    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  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13  2  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 25 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 19 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 44 49  1  0  0  0  0
 40 50  1  0  0  0  0
 11 50  1  0  0  0  0
 50 51  1  6  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0273476

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@H](O)C(=C)[C@H]2[C@H](OC(C)=O)[C@@]3(CC(OC(=O)\C=C\C4=CC=CC=C4)C(C)=C3[C@@H](OC(=O)C3=CC=CC=C3)[C@H](OC(C)=O)[C@]12C)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C42H48O12/c1-23-30(46)21-32(50-25(3)43)41(8)35(23)37(51-26(4)44)42(40(6,7)49)22-31(53-33(47)20-19-28-15-11-9-12-16-28)24(2)34(42)36(38(41)52-27(5)45)54-39(48)29-17-13-10-14-18-29/h9-20,30-32,35-38,46,49H,1,21-22H2,2-8H3/b20-19+/t30-,31?,32-,35-,36+,37-,38-,41+,42-/m0/s1

> <INCHI_KEY>
GYHMHLLTYRDKBW-SMDJPFQXSA-N

> <FORMULA>
C42H48O12

> <MOLECULAR_WEIGHT>
744.834

> <EXACT_MASS>
744.314576986

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
78.9203750419077

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aS,4S,4aR,6S,8S,8aS,9R,10R)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2E)-3-phenylprop-2-enoyl]oxy}-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-10-yl benzoate

> <JCHEM_LOGP>
4.2446161216666685

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.896065664092372

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.286528754605484

> <JCHEM_PKA_STRONGEST_BASIC>
-2.952611471604481

> <JCHEM_POLAR_SURFACE_AREA>
171.95999999999998

> <JCHEM_REFRACTIVITY>
195.34859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,4S,4aR,6S,8S,8aS,9R,10R)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2E)-3-phenylprop-2-enoyl]oxy}-2H,3H,4H,4aH,6H,7H,8H,9H,10H-cyclohexa[f]azulen-10-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       6.990   0.352   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.316   1.857   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.783   2.327   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.923   1.293   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.108   3.832   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.968   4.867   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.294   6.372   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.760   6.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.086   8.348   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.901   5.808   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.501   4.397   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.939   5.873   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.176   2.892   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.796   2.208   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.813   0.668   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.155  -0.087   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.172  -1.627   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.688  -0.231   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.401   2.861   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.487   1.323   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.950   1.237   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.461   0.130   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.573  -0.214   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.088   2.056   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.917   3.056   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.581   2.697   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.641   3.814   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.203   5.291   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.138   3.455   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.576   1.978   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.073   1.619   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.511   0.142   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -7.008  -0.217   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -8.068   0.900   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -7.631   2.376   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.133   2.736   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.506   4.479   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.702   5.792   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.041   4.358   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.988   5.573   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.304   6.953   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       1.767   7.051   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       0.324   6.515   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       1.084   8.431   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -0.453   8.529   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -1.137   9.908   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -0.283  11.191   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.253  11.093   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       1.937   9.713   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.528   5.590   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       6.181   6.985   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       5.299   8.248   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       3.765   8.115   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       5.951   9.642   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   13   50                                             
CONECT   12   11                                                            
CONECT   13   11    2   14                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   24   39                                             
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   19   25                                                       
CONECT   25   24   26   37                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
CONECT   37   25   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   19   40                                                  
CONECT   40   39   41   50                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   44                                                       
CONECT   50   40   11   51                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  116    0
END

View in JSmol

Synonyms

Value	Source
(3AS,4S,4ar,6S,8S,8as,9R,10R)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2E)-3-phenylprop-2-enoyl]oxy}-2H,3H,3ah,4H,4ah,5H,6H,7H,8H,8ah,9H,10H-cyclohexa[F]azulen-10-yl benzoic acid	Generator

Chemical Formula

C₄₂H₄₈O₁₂

Average Mass

744.8340 Da

Monoisotopic Mass

744.31458 Da

IUPAC Name

(3aS,4S,4aR,6S,8S,8aS,9R,10R)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2E)-3-phenylprop-2-enoyl]oxy}-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-10-yl benzoate

Traditional Name

(3aS,4S,4aR,6S,8S,8aS,9R,10R)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2E)-3-phenylprop-2-enoyl]oxy}-2H,3H,4H,4aH,6H,7H,8H,9H,10H-cyclohexa[f]azulen-10-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@H](O)C(=C)[C@H]2[C@H](OC(C)=O)[C@@]3(CC(OC(=O)\C=C\C4=CC=CC=C4)C(C)=C3[C@@H](OC(=O)C3=CC=CC=C3)[C@H](OC(C)=O)[C@]12C)C(C)(C)O

InChI Identifier

InChI=1S/C42H48O12/c1-23-30(46)21-32(50-25(3)43)41(8)35(23)37(51-26(4)44)42(40(6,7)49)22-31(53-33(47)20-19-28-15-11-9-12-16-28)24(2)34(42)36(38(41)52-27(5)45)54-39(48)29-17-13-10-14-18-29/h9-20,30-32,35-38,46,49H,1,21-22H2,2-8H3/b20-19+/t30-,31?,32-,35-,36+,37-,38-,41+,42-/m0/s1

InChI Key

GYHMHLLTYRDKBW-SMDJPFQXSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Taxanes and derivatives

Alternative Parents

Substituents

11(15->1)-abeotaxane diterpenoid
Pentacarboxylic acid or derivatives
Cinnamic acid ester
Cinnamic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Styrene
Benzoyl
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.24	ChemAxon
pKa (Strongest Acidic)	14.29	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	171.96 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	195.35 m³·mol⁻¹	ChemAxon
Polarizability	78.92 Å³	ChemAxon
Number of Rings	5	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

4479352

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321679

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,4s,4ar,6s,8s,8as,9r,10r)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2e)-3-phenylprop-2-enoyl]oxy}-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-10-yl benzoate (NP0273476)

MOL for NP0273476 ((3as,4s,4ar,6s,8s,8as,9r,10r)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2e)-3-phenylprop-2-enoyl]oxy}-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-10-yl benzoate)

3D MOL for NP0273476 ((3as,4s,4ar,6s,8s,8as,9r,10r)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2e)-3-phenylprop-2-enoyl]oxy}-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-10-yl benzoate)

3D SDF for NP0273476 ((3as,4s,4ar,6s,8s,8as,9r,10r)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2e)-3-phenylprop-2-enoyl]oxy}-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-10-yl benzoate)

3D-SDF for NP0273476 ((3as,4s,4ar,6s,8s,8as,9r,10r)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2e)-3-phenylprop-2-enoyl]oxy}-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-10-yl benzoate)

PDB for NP0273476 ((3as,4s,4ar,6s,8s,8as,9r,10r)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2e)-3-phenylprop-2-enoyl]oxy}-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-10-yl benzoate)

3D PDB for NP0273476 ((3as,4s,4ar,6s,8s,8as,9r,10r)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2e)-3-phenylprop-2-enoyl]oxy}-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-10-yl benzoate)

SMILES for NP0273476 ((3as,4s,4ar,6s,8s,8as,9r,10r)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2e)-3-phenylprop-2-enoyl]oxy}-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-10-yl benzoate)

INCHI for NP0273476 ((3as,4s,4ar,6s,8s,8as,9r,10r)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2e)-3-phenylprop-2-enoyl]oxy}-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-10-yl benzoate)

Structure for NP0273476 ((3as,4s,4ar,6s,8s,8as,9r,10r)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2e)-3-phenylprop-2-enoyl]oxy}-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-10-yl benzoate)

3D Structure for NP0273476 ((3as,4s,4ar,6s,8s,8as,9r,10r)-4,8,9-tris(acetyloxy)-6-hydroxy-3a-(2-hydroxypropan-2-yl)-1,8a-dimethyl-5-methylidene-2-{[(2e)-3-phenylprop-2-enoyl]oxy}-2h,3h,4h,4ah,6h,7h,8h,9h,10h-cyclohexa[f]azulen-10-yl benzoate)