NP-MRD: Showing NP-Card for (1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione (NP0185026)

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Record Information

Version

2.0

Created at

2022-09-04 00:18:57 UTC

Updated at

2022-09-04 00:18:57 UTC

NP-MRD ID

NP0185026

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione

Description

Verrillin belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. (1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione is found in Antillogorgia bipinnata. (1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione was first documented in 2013 (PMID: 23626379). Based on a literature review a small amount of articles have been published on Verrillin (PMID: 33945689) (PMID: 23627293).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202182D          

 28 33  0  0  1  0            999 V2000
    4.2031    0.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2485    1.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5435    1.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4800    1.2281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7482    0.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8868   -0.2333    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7649   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4332    0.2984    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1936   -0.0217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3816   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7330    0.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5551    0.5331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3060    1.3084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5027    1.1205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8810    1.7444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9101    2.5689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1567    2.0235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0206   -0.4450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4767   -1.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7057   -1.9013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819   -0.8438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6626    0.0006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2891    0.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    1.3597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2194    1.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3010    2.0640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    1.0021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4559    0.1846    0.0000 C   0  0  1  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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
  4 17  1  6  0  0  0
  6 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  1  0  0  0
 27 24  1  1  0  0  0
  4 27  1  0  0  0  0
 28 27  1  1  0  0  0
 22 28  1  0  0  0  0
 18 28  1  0  0  0  0
M  END

     RDKit          3D

 52 57  0  0  0  0  0  0  0  0999 V2000
   -1.4071    3.6283   -0.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6583    2.4242    0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6096    2.1101    0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6616    0.6436    0.3062 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1396    0.1364   -0.8601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0834   -1.2635   -0.8227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2909   -1.4756    0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2482   -0.3476   -0.2969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6848   -0.7983   -0.4650 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0160   -1.2333   -1.8468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4057    0.4970   -0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6507    0.6836   -0.3182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4746    1.4523    0.2712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4051    0.6587    0.7782 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2226    1.3715    1.2329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4981    1.9077    2.5149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    0.4519    1.4146 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1801   -1.8445   -0.4933 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4500   -3.2512   -0.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7094   -4.1916   -0.8034 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275   -3.3425    0.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0798   -2.0936    0.7285 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8255   -1.1716   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258    0.1871   -0.1352 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1056    1.1653    0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8957    0.7019   -1.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9556    0.0674    0.7412 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7450   -1.4143    0.8720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2620    3.8424    0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7434    4.5101   -0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8227    3.4332   -1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287    2.7608   -0.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3515   -1.5245   -1.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8009   -2.4083   -0.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1320   -1.6583    1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762    0.1671   -1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9347   -1.5567    0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3303   -0.8925   -2.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1017   -2.3583   -1.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0650   -0.8899   -2.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8575    0.1275    1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9249    2.8009    2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9386   -1.4120   -1.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5665   -2.3268    1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9670   -1.5399   -1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8748   -1.0996    0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1003    1.1017    0.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6799    2.1779    0.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1732    0.8012    1.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125    1.5718   -1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1582    0.4494    1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1394   -1.7364    1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 17  1  0
 17 15  1  0
 15 16  1  1
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 15  2  1  0
  2  1  1  0
  2  3  2  0
  4 27  1  0
 27 28  1  0
 28 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  6
 22 21  1  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 11  9  1  0
 24 27  1  0
 14  8  1  0
 18 28  1  0
 18  6  1  0
  4  3  1  6
 10 38  1  0
 10 39  1  0
 10 40  1  0
  9 37  1  1
  8 36  1  6
  7 34  1  0
  7 35  1  0
  6 33  1  6
 16 42  1  0
 14 41  1  1
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
 27 51  1  1
 28 52  1  1
 22 44  1  1
 23 45  1  0
 23 46  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 18 43  1  6
M  END


  Mrv1652309042202182D          

 28 33  0  0  1  0            999 V2000
    4.2031    0.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2485    1.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5435    1.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4800    1.2281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7482    0.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8868   -0.2333    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7649   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4332    0.2984    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1936   -0.0217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3816   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7330    0.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5551    0.5331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3060    1.3084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5027    1.1205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8810    1.7444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9101    2.5689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1567    2.0235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0206   -0.4450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4767   -1.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7057   -1.9013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819   -0.8438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6626    0.0006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2891    0.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    1.3597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2194    1.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3010    2.0640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    1.0021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4559    0.1846    0.0000 C   0  0  1  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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
  4 17  1  6  0  0  0
  6 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  1  0  0  0
 27 24  1  1  0  0  0
  4 27  1  0  0  0  0
 28 27  1  1  0  0  0
 22 28  1  0  0  0  0
 18 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185026

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H]2C[C@H]3O[C@@]4(O[C@](O)([C@H]2OC1=O)C(C)=C4)[C@H]1[C@@H]2[C@H](C[C@@]1(C)O)OC(=O)[C@@H]32

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O8/c1-7-5-19-14-12-11(6-18(14,3)23)25-17(22)13(12)10(27-19)4-9-8(2)16(21)26-15(9)20(7,24)28-19/h5,8-15,23-24H,4,6H2,1-3H3/t8-,9-,10+,11-,12+,13-,14-,15-,18+,19-,20-/m0/s1

> <INCHI_KEY>
YJMXTIIUVZBPPQ-CRVPYZTRSA-N

> <FORMULA>
C20H24O8

> <MOLECULAR_WEIGHT>
392.404

> <EXACT_MASS>
392.147117733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.00093302339227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5S,8S,9S,11R,12R,15S,17R,18S,20S)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1^{1,4}.1^{12,15}.0^{5,9}.0^{18,20}]henicos-2-ene-7,13-dione

> <JCHEM_LOGP>
0.8242323919999992

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.508747633292494

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.47521037862791

> <JCHEM_PKA_STRONGEST_BASIC>
-3.013783542581322

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000001

> <JCHEM_REFRACTIVITY>
91.77000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5S,8S,9S,11R,12R,15S,17R,18S,20S)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1^{1,4}.1^{12,15}.0^{5,9}.0^{18,20}]henicos-2-ene-7,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       7.846   0.690   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.931   2.227   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.615   3.658   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.496   2.293   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.997   0.898   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.255  -0.436   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.894  -0.445   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.142   0.557   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.561  -0.041   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.912  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.568   1.125   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.103   0.995   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      11.771   2.442   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.272   2.092   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.111   3.256   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.165   4.795   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.759   3.777   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.638  -0.831   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.623  -2.070   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.051  -3.549   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.139  -1.575   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.103   0.001   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.406   1.421   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.493   2.538   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.276   3.482   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.295   3.853   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.926   1.871   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.584   0.345   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17   27                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14    2   16   17                                             
CONECT   16   15                                                            
CONECT   17   15    4                                                       
CONECT   18    6   19   28                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24    4   28                                                  
CONECT   28   27   22   18                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₈

Average Mass

392.4040 Da

Monoisotopic Mass

392.14712 Da

IUPAC Name

(1S,4S,5S,8S,9S,11R,12R,15S,17R,18S,20S)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1^{1,4}.1^{12,15}.0^{5,9}.0^{18,20}]henicos-2-ene-7,13-dione

Traditional Name

(1S,4S,5S,8S,9S,11R,12R,15S,17R,18S,20S)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1^{1,4}.1^{12,15}.0^{5,9}.0^{18,20}]henicos-2-ene-7,13-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H]2C[C@H]3O[C@@]4(O[C@](O)([C@H]2OC1=O)C(C)=C4)[C@H]1[C@@H]2[C@H](C[C@@]1(C)O)OC(=O)[C@@H]32

InChI Identifier

InChI=1S/C20H24O8/c1-7-5-19-14-12-11(6-18(14,3)23)25-17(22)13(12)10(27-19)4-9-8(2)16(21)26-15(9)20(7,24)28-19/h5,8-15,23-24H,4,6H2,1-3H3/t8-,9-,10+,11-,12+,13-,14-,15-,18+,19-,20-/m0/s1

InChI Key

YJMXTIIUVZBPPQ-CRVPYZTRSA-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

Species Name	Source	Reference
Antillogorgia bipinnata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Furopyran
Ketal
Pyran
Oxane
Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Tertiary alcohol
Furan
Dihydrofuran
Cyclic alcohol
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.82	ChemAxon
pKa (Strongest Acidic)	10.48	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.77 m³·mol⁻¹	ChemAxon
Polarizability	39 Å³	ChemAxon
Number of Rings	6	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

8985811

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10810506

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Saitman A, Sullivan SD, Theodorakis EA: A strategy toward the synthesis of C13-oxidized cembrenolides. Tetrahedron Lett. 2013 Mar 20;54(12):1612-1615. doi: 10.1016/j.tetlet.2013.01.085. [PubMed:23626379 ]
Scesa PD, West LM, Roche SP: Role of Macrocyclic Conformational Steering in a Kinetic Route toward Bielschowskysin. J Am Chem Soc. 2021 May 19;143(19):7566-7577. doi: 10.1021/jacs.1c03336. Epub 2021 May 4. [PubMed:33945689 ]
Saitman A, Theodorakis EA: Synthesis of a highly functionalized core of verrillin. Org Lett. 2013 May 17;15(10):2410-3. doi: 10.1021/ol400872h. Epub 2013 Apr 30. [PubMed:23627293 ]
LOTUS database [Link]

Showing NP-Card for (1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione (NP0185026)

MOL for NP0185026 ((1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione)

3D MOL for NP0185026 ((1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione)

3D SDF for NP0185026 ((1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione)

3D-SDF for NP0185026 ((1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione)

PDB for NP0185026 ((1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione)

3D PDB for NP0185026 ((1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione)

SMILES for NP0185026 ((1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione)

INCHI for NP0185026 ((1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione)

Structure for NP0185026 ((1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione)

3D Structure for NP0185026 ((1s,4s,5s,8s,9s,11r,12r,15s,17r,18s,20s)-4,17-dihydroxy-3,8,17-trimethyl-6,14,19,21-tetraoxahexacyclo[9.7.1.1¹,⁴.1¹²,¹⁵.0⁵,⁹.0¹⁸,²⁰]henicos-2-ene-7,13-dione)