NP-MRD: Showing NP-Card for methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate (NP0161704)

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Record Information

Version

2.0

Created at

2022-09-02 19:56:50 UTC

Updated at

2022-09-02 19:56:50 UTC

NP-MRD ID

NP0161704

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate

Description

Methyl (1R,4aR,5S,6S,8S,8aS)-6-chloro-1-formyl-8-hydroxy-5-[(3R)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate is found in Negombata magnifica. Based on a literature review very few articles have been published on methyl (1R,4aR,5S,6S,8S,8aS)-6-chloro-1-formyl-8-hydroxy-5-[(3R)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022221562D          

 27 28  0  0  1  0            999 V2000
    2.8697   -0.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842   -0.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842   -1.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2986   -0.0670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2986    0.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0131   -0.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7276   -0.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4421   -0.4795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9118   -1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7242    0.2957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1939    0.9277    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.5367    0.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0670   -0.1930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8795   -0.0498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7848   -0.9683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5973   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3151   -1.6002    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1276   -1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6579   -2.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0330   -2.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5633   -3.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3757   -2.8642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2811   -3.7827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8114   -4.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2205   -2.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6902   -1.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9724   -1.1115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  1  0  0  0
  8 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  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  2  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  2  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
  8 27  1  0  0  0  0
 15 27  1  0  0  0  0
M  END

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
    4.0868    1.2232    1.6500 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5436    1.3619    0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3744    2.5841    0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453    0.4032   -0.6628 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1582    1.0251   -1.8776 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3642   -0.7108   -0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9951   -0.1592   -0.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736   -1.1298   -0.1358 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0953   -1.7201    1.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7751   -2.1511   -1.2304 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9857   -3.4602   -1.0301 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368   -2.7620   -1.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6158   -2.4809   -0.4816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8315   -2.7420   -1.1201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6488   -1.0834    0.0469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9185   -1.0684    1.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7702   -0.2719   -0.5978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0798   -0.9540   -0.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5355   -1.4814    0.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860    1.0390    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0748    1.7187    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1193    1.1948   -0.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1830    2.9530    0.8618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4542    3.5605    0.9711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6853    1.5834    0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333    0.9921    0.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3922   -0.3053   -0.2484 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5146    0.3549    1.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2831    1.9855    2.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042    3.3983    0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925    2.9656   -0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4420    2.3685    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3981   -0.0768   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    1.8428   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5824   -1.4905   -1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6513   -1.1511    0.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8290    0.3295   -1.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9198    0.6620    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3308   -2.4077    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981   -0.8744    1.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0660   -2.2797    1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328   -1.6079   -2.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8915   -2.4580   -2.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4467   -3.8664   -1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5800   -3.1892    0.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556   -3.6799   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8667   -0.5619    1.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1158   -0.5802    2.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0168   -2.1025    1.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652   -0.0988   -1.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6850   -0.9872   -1.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4473    4.4358    0.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5578    3.9034    2.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2434    2.8317    0.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636    2.5550    1.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2669    1.7609   -0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417    0.9135    1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4630   -0.0541   -1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 21  1  0
 21 22  2  0
 21 20  1  0
 20 25  2  0
 25 26  1  0
 26 27  1  0
 27  8  1  0
  8  9  1  1
  8  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  2  0
 17 20  1  0
 15 27  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  6
  9 39  1  0
  9 40  1  0
  9 41  1  0
  7 37  1  0
  7 38  1  0
  6 35  1  0
  6 36  1  0
  4 33  1  6
  5 34  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  1 28  1  0
  1 29  1  0
 10 42  1  6
 12 43  1  0
 12 44  1  0
 13 45  1  1
 14 46  1  0
 16 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  6
 18 51  1  0
M  END


  Mrv1652309022221562D          

 27 28  0  0  1  0            999 V2000
    2.8697   -0.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842   -0.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842   -1.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2986   -0.0670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2986    0.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0131   -0.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7276   -0.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4421   -0.4795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9118   -1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7242    0.2957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1939    0.9277    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.5367    0.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0670   -0.1930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8795   -0.0498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7848   -0.9683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5973   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3151   -1.6002    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1276   -1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6579   -2.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0330   -2.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5633   -3.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3757   -2.8642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2811   -3.7827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8114   -4.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2205   -2.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6902   -1.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9724   -1.1115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  1  0  0  0
  8 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  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  2  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  2  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
  8 27  1  0  0  0  0
 15 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0161704

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC[C@H]2[C@](C)(CC[C@@H](O)C(C)=C)[C@@H](Cl)C[C@H](O)[C@]2(C)[C@H]1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H31ClO5/c1-12(2)15(24)8-9-20(3)16-7-6-13(19(26)27-5)14(11-23)21(16,4)18(25)10-17(20)22/h6,11,14-18,24-25H,1,7-10H2,2-5H3/t14-,15+,16-,17-,18-,20-,21+/m0/s1

> <INCHI_KEY>
PMPHZBAWDOYBGN-OZFZSNIHSA-N

> <FORMULA>
C21H31ClO5

> <MOLECULAR_WEIGHT>
398.92

> <EXACT_MASS>
398.1860018

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.7091821045747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,4aR,5S,6S,8S,8aS)-6-chloro-1-formyl-8-hydroxy-5-[(3R)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
2.3774754049999993

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.077415673797173

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.087234733151387

> <JCHEM_PKA_STRONGEST_BASIC>
-1.502826276340071

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
105.08519999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,4aR,5S,6S,8S,8aS)-6-chloro-1-formyl-8-hydroxy-5-[(3R)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       5.357  -0.125   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.690  -0.895   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.690  -2.435   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.024  -0.125   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.024   1.415   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.358  -0.895   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.691  -0.125   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.025  -0.895   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.035  -2.075   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.552   0.552   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0      11.562   1.732   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0      14.068   0.819   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.058  -0.360   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.575  -0.093   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.532  -1.807   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.048  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.522  -2.987   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.038  -2.720   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.028  -3.899   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      14.995  -4.434   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.985  -5.614   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      17.501  -5.347   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      15.458  -7.061   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      16.448  -8.241   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.478  -4.702   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.488  -3.522   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.015  -2.075   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   27                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   27                                             
CONECT   16   15                                                            
CONECT   17   15   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   25                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    8   15                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,4ar,5S,6S,8S,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3R)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid	Generator

Chemical Formula

C₂₁H₃₁ClO₅

Average Mass

398.9200 Da

Monoisotopic Mass

398.18600 Da

IUPAC Name

methyl (1R,4aR,5S,6S,8S,8aS)-6-chloro-1-formyl-8-hydroxy-5-[(3R)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate

Traditional Name

methyl (1R,4aR,5S,6S,8S,8aS)-6-chloro-1-formyl-8-hydroxy-5-[(3R)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC[C@H]2[C@](C)(CC[C@@H](O)C(C)=C)[C@@H](Cl)C[C@H](O)[C@]2(C)[C@H]1C=O

InChI Identifier

InChI=1S/C21H31ClO5/c1-12(2)15(24)8-9-20(3)16-7-6-13(19(26)27-5)14(11-23)21(16,4)18(25)10-17(20)22/h6,11,14-18,24-25H,1,7-10H2,2-5H3/t14-,15+,16-,17-,18-,20-,21+/m0/s1

InChI Key

PMPHZBAWDOYBGN-OZFZSNIHSA-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
Negombata magnifica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organohalogen compound
Aldehyde
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Alkyl halide
Alkyl chloride
Organochloride
Organooxygen compound
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	2.69	ALOGPS
logP	2.38	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	105.09 m³·mol⁻¹	ChemAxon
Polarizability	42.71 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

162892446

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate (NP0161704)

MOL for NP0161704 (methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate)

3D MOL for NP0161704 (methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate)

3D SDF for NP0161704 (methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate)

3D-SDF for NP0161704 (methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate)

PDB for NP0161704 (methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate)

3D PDB for NP0161704 (methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate)

SMILES for NP0161704 (methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate)

INCHI for NP0161704 (methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate)

Structure for NP0161704 (methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate)

3D Structure for NP0161704 (methyl (1r,4ar,5s,6s,8s,8as)-6-chloro-1-formyl-8-hydroxy-5-[(3r)-3-hydroxy-4-methylpent-4-en-1-yl]-5,8a-dimethyl-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylate)