NP-MRD: Showing NP-Card for Massarinolin B (NP0001593)

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Record Information

Version

1.0

Created at

2020-09-23 01:57:49 UTC

Updated at

2021-08-10 02:55:31 UTC

NP-MRD ID

NP0001593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Massarinolin B

Provided By

NPAtlas

Description

(2E,4S)-4-hydroxy-2-methyl-5-[(1R,3S,6R,9S)-6-methyl-7-oxatricyclo[4.3.0.0³,⁹]Nonan-9-yl]pent-2-enoic acid belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Massarinolin B is found in Massarina. It was first documented in 1999 (PMID: 10096869). Based on a literature review very few articles have been published on (2E,4S)-4-hydroxy-2-methyl-5-[(1R,3S,6R,9S)-6-methyl-7-oxatricyclo[4.3.0.0³,⁹]Nonan-9-yl]pent-2-enoic acid (PMID: 26389497) (PMID: 26389486) (PMID: 26389480) (PMID: 26389479).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117433D          

 41 43  0  0  0  0            999 V2000
    3.2347    1.4653    0.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7770    0.4610    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -0.5198   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6366   -0.7045    0.0102 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4450   -0.9006    1.3594 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692    0.3259   -0.5271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6838   -0.0140   -0.0285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8815   -0.0295    1.4430 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1327    0.5493    1.7052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806    0.4883    0.5543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9606    1.5144    0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4122   -0.9031    0.3994 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3323   -1.8935    0.0087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3085   -1.1673   -0.7915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0071   -0.1069   -1.6559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8336    0.8286   -0.5062 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1904    0.5762   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8994    1.5104   -0.0324 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7037   -0.3622   -1.3210 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9706    2.4017    0.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645    1.1188    1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0766    1.8322    1.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -1.2135   -1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3054   -1.6942   -0.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0145   -1.6519    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9129    1.3484   -0.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6963    0.3379   -1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843   -1.0163    1.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    0.6652    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5318    2.5056    0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8291    1.2736    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2812    1.6017   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008   -1.2335    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2614   -0.9711   -0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602   -2.3836    0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -2.6875   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.7493   -1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354   -0.3758   -1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    0.2210   -2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625    1.8733   -0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8525   -1.3209   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 14  7  1  0  0  0  0
 16  7  1  0  0  0  0
 16 10  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 23  1  0  0  0  0
  4 24  1  6  0  0  0
  5 25  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 14 37  1  6  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 16 40  1  6  0  0  0
 19 41  1  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    3.2347    1.4653    0.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7770    0.4610    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -0.5198   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6366   -0.7045    0.0102 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4450   -0.9006    1.3594 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692    0.3259   -0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6838   -0.0140   -0.0285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8815   -0.0295    1.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327    0.5493    1.7052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806    0.4883    0.5543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9606    1.5144    0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4122   -0.9031    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3323   -1.8935    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3085   -1.1673   -0.7915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0071   -0.1069   -1.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8336    0.8286   -0.5062 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1904    0.5762   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8994    1.5104   -0.0324 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7037   -0.3622   -1.3210 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9706    2.4017    0.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645    1.1188    1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0766    1.8322    1.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -1.2135   -1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3054   -1.6942   -0.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0145   -1.6519    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9129    1.3484   -0.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6963    0.3379   -1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843   -1.0163    1.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    0.6652    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5318    2.5056    0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8291    1.2736    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2812    1.6017   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008   -1.2335    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2614   -0.9711   -0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602   -2.3836    0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -2.6875   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.7493   -1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354   -0.3758   -1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    0.2210   -2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625    1.8733   -0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8525   -1.3209   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  7  6  1  1
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
 14  7  1  0
 16  7  1  0
 16 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  6
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  6
 15 38  1  0
 15 39  1  0
 16 40  1  6
 19 41  1  0
M  END


  Mrv1652306242117433D          

 41 43  0  0  0  0            999 V2000
    3.2347    1.4653    0.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7770    0.4610    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -0.5198   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6366   -0.7045    0.0102 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4450   -0.9006    1.3594 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692    0.3259   -0.5271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6838   -0.0140   -0.0285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8815   -0.0295    1.4430 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1327    0.5493    1.7052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806    0.4883    0.5543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9606    1.5144    0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4122   -0.9031    0.3994 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3323   -1.8935    0.0087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3085   -1.1673   -0.7915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0071   -0.1069   -1.6559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8336    0.8286   -0.5062 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1904    0.5762   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8994    1.5104   -0.0324 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7037   -0.3622   -1.3210 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9706    2.4017    0.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645    1.1188    1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0766    1.8322    1.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -1.2135   -1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3054   -1.6942   -0.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0145   -1.6519    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9129    1.3484   -0.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6963    0.3379   -1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843   -1.0163    1.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    0.6652    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5318    2.5056    0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8291    1.2736    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2812    1.6017   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008   -1.2335    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2614   -0.9711   -0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602   -2.3836    0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -2.6875   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.7493   -1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354   -0.3758   -1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    0.2210   -2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625    1.8733   -0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8525   -1.3209   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 14  7  1  0  0  0  0
 16  7  1  0  0  0  0
 16 10  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 23  1  0  0  0  0
  4 24  1  6  0  0  0
  5 25  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 14 37  1  6  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 16 40  1  6  0  0  0
 19 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(=C(/[H])[C@@]([H])(O[H])C([H])([H])[C@]12C([H])([H])O[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])C([H])([H])[C@]23[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-9(13(17)18)5-11(16)7-15-8-19-14(2)4-3-10(15)6-12(14)15/h5,10-12,16H,3-4,6-8H2,1-2H3,(H,17,18)/b9-5+/t10-,11+,12-,14+,15-/m0/s1

> <INCHI_KEY>
GWNSZLIEAQMRLS-SUAOZZTGSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.754195654229406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4S)-4-hydroxy-2-methyl-5-[(1R,3S,6R,9S)-6-methyl-7-oxatricyclo[4.3.0.0^{3,9}]nonan-9-yl]pent-2-enoic acid

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.3935619253333331

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.867918553301482

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.63245356541895

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8865414257946904

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
70.8543

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4S)-4-hydroxy-2-methyl-5-[(1R,3S,6R,9S)-6-methyl-7-oxatricyclo[4.3.0.0^{3,9}]nonan-9-yl]pent-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    3.2347    1.4653    0.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7770    0.4610    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -0.5198   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6366   -0.7045    0.0102 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4450   -0.9006    1.3594 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692    0.3259   -0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6838   -0.0140   -0.0285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8815   -0.0295    1.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327    0.5493    1.7052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806    0.4883    0.5543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9606    1.5144    0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4122   -0.9031    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3323   -1.8935    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3085   -1.1673   -0.7915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0071   -0.1069   -1.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8336    0.8286   -0.5062 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1904    0.5762   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8994    1.5104   -0.0324 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7037   -0.3622   -1.3210 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9706    2.4017    0.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645    1.1188    1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0766    1.8322    1.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -1.2135   -1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3054   -1.6942   -0.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0145   -1.6519    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9129    1.3484   -0.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6963    0.3379   -1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843   -1.0163    1.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    0.6652    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5318    2.5056    0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8291    1.2736    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2812    1.6017   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008   -1.2335    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2614   -0.9711   -0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602   -2.3836    0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -2.6875   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.7493   -1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354   -0.3758   -1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    0.2210   -2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625    1.8733   -0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8525   -1.3209   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  7  6  1  1
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
 14  7  1  0
 16  7  1  0
 16 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  6
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  6
 15 38  1  0
 15 39  1  0
 16 40  1  6
 19 41  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.235   1.465   0.970  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.777   0.461   0.027  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.018  -0.520  -0.393  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.637  -0.705   0.010  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.445  -0.901   1.359  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.669   0.326  -0.527  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.684  -0.014  -0.029  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.882  -0.030   1.443  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.133   0.549   1.705  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.881   0.488   0.554  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.961   1.514   0.473  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.412  -0.903   0.399  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.332  -1.894   0.009  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.309  -1.167  -0.792  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.007  -0.107  -1.656  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.834   0.829  -0.506  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.190   0.576  -0.438  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.899   1.510  -0.032  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.704  -0.362  -1.321  0.00  0.00           O+0
HETATM   20  H   UNK     0       2.971   2.402   0.396  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.465   1.119   1.647  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.077   1.832   1.640  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.522  -1.214  -1.095  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.305  -1.694  -0.460  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.014  -1.652   1.667  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.913   1.348  -0.148  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.696   0.338  -1.640  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.784  -1.016   1.934  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.151   0.665   1.913  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.532   2.506   0.741  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.829   1.274   1.099  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.281   1.602  -0.586  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.801  -1.234   1.388  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.261  -0.971  -0.304  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.860  -2.384   0.870  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.767  -2.688  -0.628  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.638  -1.749  -1.417  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.035  -0.376  -1.940  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.355   0.221  -2.516  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.663   1.873  -0.695  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.853  -1.321  -0.992  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1    3   17                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5    6   24                                             
CONECT    5    4   25                                                       
CONECT    6    4    7   26   27                                             
CONECT    7    6    8   14   16                                             
CONECT    8    7    9   28   29                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   12   16                                             
CONECT   11   10   30   31   32                                             
CONECT   12   10   13   33   34                                             
CONECT   13   12   14   35   36                                             
CONECT   14   13   15    7   37                                             
CONECT   15   14   16   38   39                                             
CONECT   16   15    7   10   40                                             
CONECT   17    2   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   41                                                       
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    6                                                            
CONECT   28    8                                                            
CONECT   29    8                                                            
CONECT   30   11                                                            
CONECT   31   11                                                            
CONECT   32   11                                                            
CONECT   33   12                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   19                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
    3.2347    1.4653    0.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7770    0.4610    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -0.5198   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6366   -0.7045    0.0102 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4450   -0.9006    1.3594 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692    0.3259   -0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6838   -0.0140   -0.0285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8815   -0.0295    1.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327    0.5493    1.7052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806    0.4883    0.5543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9606    1.5144    0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4122   -0.9031    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3323   -1.8935    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3085   -1.1673   -0.7915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0071   -0.1069   -1.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8336    0.8286   -0.5062 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1904    0.5762   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8994    1.5104   -0.0324 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7037   -0.3622   -1.3210 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9706    2.4017    0.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645    1.1188    1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0766    1.8322    1.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -1.2135   -1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3054   -1.6942   -0.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0145   -1.6519    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9129    1.3484   -0.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6963    0.3379   -1.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7843   -1.0163    1.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    0.6652    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5318    2.5056    0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8291    1.2736    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2812    1.6017   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008   -1.2335    1.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2614   -0.9711   -0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602   -2.3836    0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7667   -2.6875   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.7493   -1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354   -0.3758   -1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    0.2210   -2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6625    1.8733   -0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8525   -1.3209   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  7  6  1  1
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
 14  7  1  0
 16  7  1  0
 16 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  6
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  6
 15 38  1  0
 15 39  1  0
 16 40  1  6
 19 41  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2E,4S)-4-Hydroxy-2-methyl-5-[(1R,3S,6R,9S)-6-methyl-7-oxatricyclo[4.3.0.0,]nonan-9-yl]pent-2-enoate	Generator

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3370 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

(2E,4S)-4-hydroxy-2-methyl-5-[(1R,3S,6R,9S)-6-methyl-7-oxatricyclo[4.3.0.0^{3,9}]nonan-9-yl]pent-2-enoic acid

Traditional Name

(2E,4S)-4-hydroxy-2-methyl-5-[(1R,3S,6R,9S)-6-methyl-7-oxatricyclo[4.3.0.0^{3,9}]nonan-9-yl]pent-2-enoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(=C(/[H])[C@@]([H])(O[H])C([H])([H])[C@]12C([H])([H])O[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])C([H])([H])[C@]23[H])\C([H])([H])[H]

InChI Identifier

InChI=1S/C15H22O4/c1-9(13(17)18)5-11(16)7-15-8-19-14(2)4-3-10(15)6-12(14)15/h5,10-12,16H,3-4,6-8H2,1-2H3,(H,17,18)/b9-5+/t10-,11+,12-,14+,15-/m0/s1

InChI Key

GWNSZLIEAQMRLS-SUAOZZTGSA-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
Massarina	NPAtlas	10096869

Species Where Detected

Species Name	Source	Reference
Massarina tunicata	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Pinane monoterpenoid
Medium-chain hydroxy acid
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Oxepane
Fatty acyl
Fatty acid
Unsaturated fatty acid
Oxolane
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.42	ALOGPS
logP	1.39	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.63	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.85 m³·mol⁻¹	ChemAxon
Polarizability	28.75 Å³	ChemAxon
Number of Rings	3	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

NPAtlas ID

NPA018448

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8715087

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10539696

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Oh H, Gloer JB, Shearer CA: Massarinolins A-C: new bioactive sesquiterpenoids from the aquatic fungus massarina tunicata J Nat Prod. 1999 Mar;62(3):497-501. doi: 10.1021/np980447+. [PubMed:10096869 ]
Authors unspecified: Lung Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389497 ]
Authors unspecified: Endometrial Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:26389486 ]
Authors unspecified: Ewing Sarcoma and Undifferentiated Small Round Cell Sarcomas of Bone and Soft Tissue Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389480 ]
Authors unspecified: Bladder Cancer Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389479 ]

Showing NP-Card for Massarinolin B (NP0001593)

MOL for NP0001593 (Massarinolin B)

3D MOL for NP0001593 (Massarinolin B)

3D SDF for NP0001593 (Massarinolin B)

3D-SDF for NP0001593 (Massarinolin B)

PDB for NP0001593 (Massarinolin B)

3D PDB for NP0001593 (Massarinolin B)

SMILES for NP0001593 (Massarinolin B)

INCHI for NP0001593 (Massarinolin B)

Structure for NP0001593 (Massarinolin B)

3D Structure for NP0001593 (Massarinolin B)