NP-MRD: Showing NP-Card for (3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol (NP0184842)

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Record Information

Version

1.0

Created at

2022-09-04 00:04:29 UTC

Updated at

2022-09-04 00:04:29 UTC

NP-MRD ID

NP0184842

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol

Description

(3R,3aS,4S,5R,8aS)-5-[(2S,5R)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3,3a,4,5,6,7,8,8a-octahydroazulen-4-ol belongs to the class of organic compounds known as pachydictyane and cneorubin diterpenoids. These are diterpenoids with a structure that is based either on the pachydictyane or the cneorubin skeleton. Pachydictyane is a bicyclic compound consisting of a guaiane skeleton that carries a prenyl group attached to the C12 carbon atom. Cneorubin is a tricyclic compound consisting of a cycloprop[e]azulene where the cyclopropane carries a methyl group and a 4-methylpentyl group. (3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol is found in Dictyota dichotoma. Based on a literature review very few articles have been published on (3R,3aS,4S,5R,8aS)-5-[(2S,5R)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3,3a,4,5,6,7,8,8a-octahydroazulen-4-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202042D          

 25 26  0  0  1  0            999 V2000
    3.1690    1.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6713   -1.5938    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3699   -2.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871   -1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0015   -2.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8172   -1.9929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1187   -1.2249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3316   -2.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8460   -3.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9766   -2.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6866   -3.1523    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1690   -1.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3157   -1.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860   -1.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4672   -2.2272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  6  0  0  0
  6  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
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
  2 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  6  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
   -4.5672   -1.5143   -1.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2834   -1.2515   -1.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028   -2.3231   -1.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601   -2.6067   -0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321   -1.3932   -0.3390 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8375   -1.8708    0.0089 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4510   -2.5853   -1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8143   -0.7590    0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0161    0.1939   -0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9294    1.2927   -0.4114 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4405    2.0387    0.6896 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    1.0394   -0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9755    2.4325    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7679    0.1700    0.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2019    0.5262   -1.6986 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1658   -0.5616    0.7365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1660   -1.1987    1.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5411   -0.0876    0.4621 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8650    0.0993   -1.0115 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0076    1.0400   -0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9501    1.7366    0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7477    1.3182    0.9735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6297    2.2567    0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9675    1.3434    2.3490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2814    2.5404    2.7329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8394   -2.5014   -1.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3371   -0.8017   -1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8904   -3.2508   -2.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990   -2.0478   -2.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6735   -3.3998   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8762   -3.0401    0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4526   -0.7927   -1.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8423   -2.5724    0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3485   -3.6913   -1.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5517   -2.3966   -1.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0259   -2.2135   -2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7891   -1.3285    0.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6376   -0.2875    1.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9888    0.6172   -0.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2899   -0.3403   -1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8841    2.0699   -1.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955    1.9034    1.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0568    2.4253   -0.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4075    3.2313   -0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8979    2.6134    1.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0433   -0.8730    0.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0328    0.1723    1.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6909    0.6388    1.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5155    0.3537    0.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2419   -0.5975    2.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3408   -0.7085    0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0305    0.4755   -1.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7798    1.1310   -1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6712    2.5042    0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9249    2.3505    1.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1405    1.9921   -0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361    3.3009    0.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4607    3.1878    2.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  1
 24 25  1  0
 22 18  1  0
 18 16  1  0
 16 17  1  0
 16  5  1  0
 18 19  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  6 33  1  1
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  6
 11 42  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
  5 32  1  6
  4 30  1  0
  4 31  1  0
  3 28  1  0
  3 29  1  0
  1 26  1  0
  1 27  1  0
 19 52  1  6
 20 53  1  0
 21 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 25 58  1  0
 18 51  1  1
 16 49  1  1
 17 50  1  0
M  END


  Mrv1652309042202042D          

 25 26  0  0  1  0            999 V2000
    3.1690    1.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6713   -1.5938    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3699   -2.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871   -1.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0015   -2.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8172   -1.9929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1187   -1.2249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3316   -2.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8460   -3.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9766   -2.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6866   -3.1523    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1690   -1.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3157   -1.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860   -1.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4672   -2.2272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  6  0  0  0
  6  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
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
  2 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  6  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184842

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CC[C@@H](O)C(C)(C)Cl)[C@H]1CCC(=C)[C@H]2C=C[C@@](C)(OO)[C@@H]2[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H33ClO4/c1-12-6-8-15(13(2)7-9-16(22)19(3,4)21)18(23)17-14(12)10-11-20(17,5)25-24/h10-11,13-18,22-24H,1,6-9H2,2-5H3/t13-,14+,15+,16+,17-,18-,20+/m0/s1

> <INCHI_KEY>
JFPULJNUBFSIFL-VBTWNPCZSA-N

> <FORMULA>
C20H33ClO4

> <MOLECULAR_WEIGHT>
372.93

> <EXACT_MASS>
372.2067372

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.04375170181191

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,4S,5R,8aS)-5-[(2S,5R)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3,3a,4,5,6,7,8,8a-octahydroazulen-4-ol

> <JCHEM_LOGP>
3.4466340553333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.866438033732223

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.694177489716102

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9954004824033653

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
101.36569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,4S,5R,8aS)-5-[(2S,5R)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol

> <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       5.916   2.848   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.720  -2.975   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.157  -4.409   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.243  -2.746   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.203  -3.950   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.726  -3.720   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.288  -2.287   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      13.686  -4.924   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.646  -6.128   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.890  -3.964   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      12.482  -5.884   0.000  0.00  0.00          Cl+0
HETATM   16  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.916  -3.615   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.456  -2.672   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.894  -3.139   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.739  -4.158   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16    5   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   22                                                  
CONECT   19   18    2   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₃ClO₄

Average Mass

372.9300 Da

Monoisotopic Mass

372.20674 Da

IUPAC Name

(3R,3aS,4S,5R,8aS)-5-[(2S,5R)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3,3a,4,5,6,7,8,8a-octahydroazulen-4-ol

Traditional Name

(3R,3aS,4S,5R,8aS)-5-[(2S,5R)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol

CAS Registry Number

Not Available

SMILES

C[C@@H](CC[C@@H](O)C(C)(C)Cl)[C@H]1CCC(=C)[C@H]2C=C[C@@](C)(OO)[C@@H]2[C@H]1O

InChI Identifier

InChI=1S/C20H33ClO4/c1-12-6-8-15(13(2)7-9-16(22)19(3,4)21)18(23)17-14(12)10-11-20(17,5)25-24/h10-11,13-18,22-24H,1,6-9H2,2-5H3/t13-,14+,15+,16+,17-,18-,20+/m0/s1

InChI Key

JFPULJNUBFSIFL-VBTWNPCZSA-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
Dictyota dichotoma	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pachydictyane and cneorubin diterpenoids. These are diterpenoids with a structure that is based either on the pachydictyane or the cneorubin skeleton. Pachydictyane is a bicyclic compound consisting of a guaiane skeleton that carries a prenyl group attached to the C12 carbon atom. Cneorubin is a tricyclic compound consisting of a cycloprop[e]azulene where the cyclopropane carries a methyl group and a 4-methylpentyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Pachydictyane and cneorubin diterpenoids

Alternative Parents

Substituents

Pachydictyane or cneorubin diterpenoid
Cyclic alcohol
Chlorohydrin
Halohydrin
Hydroperoxide
Secondary alcohol
Peroxol
Alkyl hydroperoxide
Organooxygen compound
Organochloride
Alkyl chloride
Organohalogen compound
Organic oxygen compound
Alcohol
Alkyl halide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.45	ChemAxon
pKa (Strongest Acidic)	11.69	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	101.37 m³·mol⁻¹	ChemAxon
Polarizability	41.04 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162931647

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol (NP0184842)

MOL for NP0184842 ((3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol)

3D MOL for NP0184842 ((3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol)

3D SDF for NP0184842 ((3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol)

3D-SDF for NP0184842 ((3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol)

PDB for NP0184842 ((3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol)

3D PDB for NP0184842 ((3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol)

SMILES for NP0184842 ((3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol)

INCHI for NP0184842 ((3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol)

Structure for NP0184842 ((3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol)

3D Structure for NP0184842 ((3r,3as,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-hydroperoxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydroazulen-4-ol)