NP-MRD: Showing NP-Card for avicennone B (NP0032995)

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Record Information

Version

2.0

Created at

2021-06-19 23:39:39 UTC

Updated at

2021-06-30 00:02:31 UTC

NP-MRD ID

NP0032995

Secondary Accession Numbers

None

Natural Product Identification

Common Name

avicennone B

Provided By

JEOL Database JEOL Logo

Description

Avicennone B belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. avicennone B is found in Avicennia marina. avicennone B was first documented in 2007 (PMID: 17500572). Based on a literature review a small amount of articles have been published on Avicennone B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101393D          

 44 45  0  0  0  0            999 V2000
   -4.5576   -4.0858    2.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0039   -4.4235    1.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -3.5538    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966   -2.5492    1.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756   -3.9936   -0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5105   -5.3731   -1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0849   -5.8329   -2.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7197   -4.9230   -3.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7739   -3.5531   -2.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931   -3.0675   -1.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2148   -1.5988   -1.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578   -0.9240   -2.3248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4828   -1.1310   -1.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020   -0.9011   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2221   -1.4669   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2502   -2.5864   -0.1057 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1791   -0.5084    0.8398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6121    0.6913    0.6916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6192    0.8459    1.8679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1088    2.2986    1.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    0.4525    3.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7930    0.0510    1.6701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2657    0.5692   -0.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4221    1.1368   -1.6863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636   -3.1164    2.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7775   -4.0790    3.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2951   -4.8494    2.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4768   -2.8568   -3.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1033    1.5229    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6165    2.5938    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7475   -0.6134    3.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7122    0.6125    4.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954    1.0320    3.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543   -0.9022    1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2387    1.0642   -0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8460    0.9436   -2.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 23  1  0  0  0  0
 23 14  1  0  0  0  0
 10  5  2  0  0  0  0
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  8  7  1  0  0  0  0
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  8 30  1  0  0  0  0
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  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 24 44  1  0  0  0  0
M  END

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -4.5576   -4.0858    2.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0039   -4.4235    1.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -3.5538    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966   -2.5492    1.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756   -3.9936   -0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5105   -5.3731   -1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0849   -5.8329   -2.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7197   -4.9230   -3.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7739   -3.5531   -2.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931   -3.0675   -1.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2148   -1.5988   -1.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578   -0.9240   -2.3248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4828   -1.1310   -1.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020   -0.9011   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2221   -1.4669   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2502   -2.5864   -0.1057 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1791   -0.5084    0.8398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6121    0.6913    0.6916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6192    0.8459    1.8679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1088    2.2986    1.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    0.4525    3.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7930    0.0510    1.6701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2657    0.5692   -0.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4221    1.1368   -1.6863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636   -3.1164    2.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7775   -4.0790    3.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2951   -4.8494    2.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7827   -6.1025   -0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0336   -6.9008   -2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3834   -5.2767   -4.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4768   -2.8568   -3.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -2.1567   -2.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5489   -0.8933   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1506   -0.4548   -2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    1.5229    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824    2.9944    2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8437    2.4234    2.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7122    0.6125    4.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8460    0.9436   -2.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 23  1  0
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  5  3  1  0
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  2  1  1  0
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 24 44  1  0
M  END


  Mrv1652306202101393D          

 44 45  0  0  0  0            999 V2000
   -4.5576   -4.0858    2.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0039   -4.4235    1.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -3.5538    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966   -2.5492    1.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756   -3.9936   -0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5105   -5.3731   -1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0849   -5.8329   -2.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7197   -4.9230   -3.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1791   -0.5084    0.8398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6121    0.6913    0.6916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6192    0.8459    1.8679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1088    2.2986    1.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    0.4525    3.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7930    0.0510    1.6701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2657    0.5692   -0.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4221    1.1368   -1.6863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636   -3.1164    2.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2951   -4.8494    2.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7827   -6.1025   -0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5543   -0.9022    1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2387    1.0642   -0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8460    0.9436   -2.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
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 23 14  1  0  0  0  0
 10  5  2  0  0  0  0
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  7 29  1  0  0  0  0
  6 28  1  0  0  0  0
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  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 24 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])\C(=C(/OC([H])([H])[H])C2=C(C([H])=C([H])C([H])=C2[H])C(=O)OC([H])([H])[H])C(=O)O[C@]1([H])C(O[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O7/c1-17(2,21)14-12(18)11(16(20)24-14)13(22-3)9-7-5-6-8-10(9)15(19)23-4/h5-8,12,14,18,21H,1-4H3/b13-11+/t12-,14-/m0/s1

> <INCHI_KEY>
NSSLCNKUPNAQRW-HLXCCUCLSA-N

> <FORMULA>
C17H20O7

> <MOLECULAR_WEIGHT>
336.34

> <EXACT_MASS>
336.120902984

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.491640658001224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-{[(3E,4S,5S)-4-hydroxy-5-(2-hydroxypropan-2-yl)-2-oxooxolan-3-ylidene](methoxy)methyl}benzoate

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
0.9479093139999996

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.339532499863243

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.066738606018681

> <JCHEM_PKA_STRONGEST_BASIC>
-3.145855944922678

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
85.35030000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-{[(3E,4S,5S)-4-hydroxy-5-(2-hydroxypropan-2-yl)-2-oxooxolan-3-ylidene](methoxy)methyl}benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -4.5576   -4.0858    2.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0039   -4.4235    1.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -3.5538    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966   -2.5492    1.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756   -3.9936   -0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5105   -5.3731   -1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0849   -5.8329   -2.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7197   -4.9230   -3.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7739   -3.5531   -2.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931   -3.0675   -1.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2148   -1.5988   -1.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578   -0.9240   -2.3248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4828   -1.1310   -1.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020   -0.9011   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2221   -1.4669   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2502   -2.5864   -0.1057 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1791   -0.5084    0.8398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6121    0.6913    0.6916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6192    0.8459    1.8679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1088    2.2986    1.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    0.4525    3.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7930    0.0510    1.6701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2657    0.5692   -0.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4221    1.1368   -1.6863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636   -3.1164    2.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7775   -4.0790    3.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2951   -4.8494    2.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7827   -6.1025   -0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0336   -6.9008   -2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3834   -5.2767   -4.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4768   -2.8568   -3.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -2.1567   -2.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5489   -0.8933   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1506   -0.4548   -2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    1.5229    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824    2.9944    2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8437    2.4234    2.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6165    2.5938    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7475   -0.6134    3.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7122    0.6125    4.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954    1.0320    3.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543   -0.9022    1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2387    1.0642   -0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8460    0.9436   -2.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 23  1  0
 23 14  1  0
 10  5  2  0
 18 19  1  0
  6  5  1  0
 11 12  1  0
 14 11  2  0
 12 13  1  0
 11 10  1  0
 19 22  1  6
 14 15  1  0
 19 20  1  0
  8  7  1  0
 19 21  1  0
 10  9  1  0
  5  3  1  0
  9  8  2  0
 15 16  2  0
  3  2  1  0
  7  6  2  0
  3  4  2  0
 15 17  1  0
  2  1  1  0
 17 18  1  0
 23 24  1  0
  8 30  1  0
  7 29  1  0
  6 28  1  0
  9 31  1  0
 18 35  1  6
 23 43  1  1
 13 32  1  0
 13 33  1  0
 13 34  1  0
 22 42  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 24 44  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.558  -4.086   2.325  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.004  -4.423   1.052  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.057  -3.554   0.609  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.697  -2.549   1.201  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.576  -3.994  -0.732  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.510  -5.373  -1.007  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.085  -5.833  -2.253  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.720  -4.923  -3.239  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.774  -3.553  -2.977  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.193  -3.067  -1.724  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.215  -1.599  -1.561  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.158  -0.924  -2.325  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.483  -1.131  -1.831  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.302  -0.901  -0.868  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.222  -1.467  -0.037  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.250  -2.586  -0.106  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.179  -0.508   0.840  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.612   0.691   0.692  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.619   0.846   1.868  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.109   2.299   1.939  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.000   0.453   3.213  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.793   0.051   1.670  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.266   0.569  -0.682  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.422   1.137  -1.686  0.00  0.00           O+0
HETATM   25  H   UNK     0      -5.064  -3.116   2.276  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.777  -4.079   3.092  0.00  0.00           H+0
HETATM   27  H   UNK     0      -5.295  -4.849   2.587  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.783  -6.103  -0.247  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.034  -6.901  -2.451  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.383  -5.277  -4.211  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.477  -2.857  -3.760  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.816  -2.157  -2.018  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.549  -0.893  -0.764  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.151  -0.455  -2.373  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.103   1.523   0.713  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.282   2.994   2.118  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.844   2.423   2.743  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.616   2.594   1.014  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.748  -0.613   3.238  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.712   0.613   4.031  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.095   1.032   3.423  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.554  -0.902   1.728  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.239   1.064  -0.740  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.846   0.944  -2.543  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5   10    6    3                                                  
CONECT    6    5    7   28                                                  
CONECT    7    8    6   29                                                  
CONECT    8    7    9   30                                                  
CONECT    9   10    8   31                                                  
CONECT   10    5   11    9                                                  
CONECT   11   12   14   10                                                  
CONECT   12   11   13                                                       
CONECT   13   12   32   33   34                                             
CONECT   14   23   11   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   23   19   17   35                                             
CONECT   19   18   22   20   21                                             
CONECT   20   19   36   37   38                                             
CONECT   21   19   39   40   41                                             
CONECT   22   19   42                                                       
CONECT   23   18   14   24   43                                             
CONECT   24   23   44                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32   13                                                            
CONECT   33   13                                                            
CONECT   34   13                                                            
CONECT   35   18                                                            
CONECT   36   20                                                            
CONECT   37   20                                                            
CONECT   38   20                                                            
CONECT   39   21                                                            
CONECT   40   21                                                            
CONECT   41   21                                                            
CONECT   42   22                                                            
CONECT   43   23                                                            
CONECT   44   24                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

RDKit          3D

44 45  0  0  0  0  0  0  0  0999 V2000
   -4.5576   -4.0858    2.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0039   -4.4235    1.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571   -3.5538    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966   -2.5492    1.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756   -3.9936   -0.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5105   -5.3731   -1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0849   -5.8329   -2.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7197   -4.9230   -3.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7739   -3.5531   -2.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931   -3.0675   -1.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2148   -1.5988   -1.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578   -0.9240   -2.3248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4828   -1.1310   -1.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020   -0.9011   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2221   -1.4669   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2502   -2.5864   -0.1057 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1791   -0.5084    0.8398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6121    0.6913    0.6916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6192    0.8459    1.8679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1088    2.2986    1.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    0.4525    3.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7930    0.0510    1.6701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2657    0.5692   -0.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4221    1.1368   -1.6863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636   -3.1164    2.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7775   -4.0790    3.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2951   -4.8494    2.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7827   -6.1025   -0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0336   -6.9008   -2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3834   -5.2767   -4.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4768   -2.8568   -3.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -2.1567   -2.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5489   -0.8933   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1506   -0.4548   -2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    1.5229    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824    2.9944    2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8437    2.4234    2.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6165    2.5938    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7475   -0.6134    3.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7122    0.6125    4.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954    1.0320    3.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543   -0.9022    1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2387    1.0642   -0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8460    0.9436   -2.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 23  1  0
 23 14  1  0
 10  5  2  0
 18 19  1  0
  6  5  1  0
 11 12  1  0
 14 11  2  0
 12 13  1  0
 11 10  1  0
 19 22  1  6
 14 15  1  0
 19 20  1  0
  8  7  1  0
 19 21  1  0
 10  9  1  0
  5  3  1  0
  9  8  2  0
 15 16  2  0
  3  2  1  0
  7  6  2  0
  3  4  2  0
 15 17  1  0
  2  1  1  0
 17 18  1  0
 23 24  1  0
  8 30  1  0
  7 29  1  0
  6 28  1  0
  9 31  1  0
 18 35  1  6
 23 43  1  1
 13 32  1  0
 13 33  1  0
 13 34  1  0
 22 42  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 24 44  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₀O₇

Average Mass

336.3400 Da

Monoisotopic Mass

336.12090 Da

IUPAC Name

methyl 2-{[(3E,4S,5S)-4-hydroxy-5-(2-hydroxypropan-2-yl)-2-oxooxolan-3-ylidene](methoxy)methyl}benzoate

Traditional Name

methyl 2-{[(3E,4S,5S)-4-hydroxy-5-(2-hydroxypropan-2-yl)-2-oxooxolan-3-ylidene](methoxy)methyl}benzoate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])\C(=C(/OC([H])([H])[H])C2=C(C([H])=C([H])C([H])=C2[H])C(=O)OC([H])([H])[H])C(=O)O[C@]1([H])C(O[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C17H20O7/c1-17(2,21)14-12(18)11(16(20)24-14)13(22-3)9-7-5-6-8-10(9)15(19)23-4/h5-8,12,14,18,21H,1-4H3/b13-11+/t12-,14-/m0/s1

InChI Key

NSSLCNKUPNAQRW-HLXCCUCLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Avicennia marina	JEOL database	Han, L., et al, J. Nat. Prod. 70, 923 (2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tertiary alcohol
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.41	ALOGPS
logP	0.95	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	13.07	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.35 m³·mol⁻¹	ChemAxon
Polarizability	33.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

20568520

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16737079

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Han L, Huang X, Dahse HM, Moellmann U, Fu H, Grabley S, Sattler I, Lin W: Unusual naphthoquinone derivatives from the twigs of Avicennia marina. J Nat Prod. 2007 Jun;70(6):923-7. doi: 10.1021/np060587g. Epub 2007 May 15. [PubMed:17500572 ]
Han, L., et al. (2007). Han, L., et al, J. Nat. Prod. 70, 923 (2007). J. Nat. Prod..

Showing NP-Card for avicennone B (NP0032995)

MOL for NP0032995 (avicennone B)

3D MOL for NP0032995 (avicennone B)

3D SDF for NP0032995 (avicennone B)

3D-SDF for NP0032995 (avicennone B)

PDB for NP0032995 (avicennone B)

3D PDB for NP0032995 (avicennone B)

SMILES for NP0032995 (avicennone B)

INCHI for NP0032995 (avicennone B)

Structure for NP0032995 (avicennone B)

3D Structure for NP0032995 (avicennone B)