NP-MRD: Showing NP-Card for [(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate (NP0321354)

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Record Information

Version

2.0

Created at

2022-09-11 23:30:58 UTC

Updated at

2022-09-11 23:30:58 UTC

NP-MRD ID

NP0321354

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate

Description

[(1S,4aS,10R,10aR)-5,8,10-trihydroxy-7-[(2S)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-1,2,3,4,4a,6,10,10a-octahydrophenanthren-1-yl]methyl formate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. [(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate is found in Plectranthus lanuginosus. Based on a literature review very few articles have been published on [(1S,4aS,10R,10aR)-5,8,10-trihydroxy-7-[(2S)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-1,2,3,4,4a,6,10,10a-octahydrophenanthren-1-yl]methyl formate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122201302D          

 29 31  0  0  1  0            999 V2000
   -0.4421   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9204    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6021    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5206    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6639    0.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4391    1.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5824    2.0787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 11  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
  9 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
    5.0657   -1.0654    1.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3572   -0.6332    0.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2094    0.7353    0.3718 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5978    1.3263    0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3321    1.1107   -0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9482    0.5737   -0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8997    1.3872   -0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1919    2.7445   -0.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5142    0.9426   -0.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4669    1.8346   -0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8921    1.4399   -0.2956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4577    1.5598   -1.5224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8808    0.0481    0.3031 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1401   -0.3966    0.9320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8812   -1.0416    2.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1319    0.7225    1.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5441    1.4035    0.0584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4466    2.4417    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8567    2.7259    1.3428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9004   -1.4321    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0605   -2.4346   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5473   -2.2723   -0.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2032   -0.8759   -0.6430 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6144   -0.6615   -2.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2450   -0.5112   -0.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2363   -1.3346   -0.7891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795   -2.6941   -0.9032 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6121   -0.8358   -0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5010   -1.6982   -0.9744 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7418   -0.5966    2.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2547   -2.1569    1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0020   -0.8844    1.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8818    1.1666    1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3674    0.5303    0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8673    2.0995    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6244    1.8498   -0.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7800    0.7853   -1.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2416    2.2243   -0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8550    3.2588    0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2026    2.8634   -0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3892    2.1564    0.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0004    2.2828   -2.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1447    0.1570    1.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5337   -0.6610    3.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9898   -2.1335    2.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8307   -0.7825    2.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7877    1.3926    2.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0463    0.2075    1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8096    3.0159   -0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6330   -0.9148   -0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5706   -1.9632    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2641   -3.4948   -0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2495   -2.4669   -1.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2825   -2.6405    0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1497   -2.9509   -1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0081    0.1204   -2.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2834   -1.6127   -2.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6831   -0.6172   -2.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5762   -3.3439   -0.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 14 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 28  6  1  0
 25  9  1  0
 23 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  1
  4 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  8 39  1  0
 10 40  1  0
 11 41  1  1
 12 42  1  0
 13 43  1  1
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 18 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  0
 22 55  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 27 59  1  0
M  END


  Mrv1652309122201302D          

 29 31  0  0  1  0            999 V2000
   -0.4421   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -1.5395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9204    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6021    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5206    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6639    0.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4391    1.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5824    2.0787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 11  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
  9 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0321354

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H](C)CC1=C(O)C2=C[C@@H](O)[C@H]3[C@@](C)(COC=O)CCC[C@]3(C)C2=C(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O7/c1-12(28-4)8-14-17(25)13-9-15(24)20-21(2,10-29-11-23)6-5-7-22(20,3)16(13)19(27)18(14)26/h9,11-12,15,20,24-25,27H,5-8,10H2,1-4H3/t12-,15+,20-,21+,22+/m0/s1

> <INCHI_KEY>
LIJILMVGVVXBFG-KAWGCRPPSA-N

> <FORMULA>
C22H30O7

> <MOLECULAR_WEIGHT>
406.475

> <EXACT_MASS>
406.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.15920362425629

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,4aS,10R,10aR)-5,8,10-trihydroxy-7-[(2S)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-1,2,3,4,4a,6,10,10a-octahydrophenanthren-1-yl]methyl formate

> <JCHEM_LOGP>
1.1530522086666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.549493024919787

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.5203581741061205

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0318520397514055

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
109.30089999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,4aS,10R,10aR)-5,8,10-trihydroxy-7-[(2S)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2H-phenanthren-1-yl]methyl formate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.825  -4.207   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.055  -2.874   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.485  -2.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.255  -4.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.255  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.795   1.127   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.185   2.461   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.457   1.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.172   0.320   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.439   1.837   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.886   2.364   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.154   3.880   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.645  -2.874   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.875  -4.207   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.795  -4.207   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   25                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   23                                                  
CONECT   14   13   15   16   20                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   14   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   13   24   25                                             
CONECT   24   23                                                            
CONECT   25   23    9   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    6   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
[(1S,4AS,10R,10ar)-5,8,10-trihydroxy-7-[(2S)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-1,2,3,4,4a,6,10,10a-octahydrophenanthren-1-yl]methyl formic acid	Generator

Chemical Formula

C₂₂H₃₀O₇

Average Mass

406.4750 Da

Monoisotopic Mass

406.19915 Da

IUPAC Name

[(1S,4aS,10R,10aR)-5,8,10-trihydroxy-7-[(2S)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-1,2,3,4,4a,6,10,10a-octahydrophenanthren-1-yl]methyl formate

Traditional Name

[(1S,4aS,10R,10aR)-5,8,10-trihydroxy-7-[(2S)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2H-phenanthren-1-yl]methyl formate

CAS Registry Number

Not Available

SMILES

CO[C@@H](C)CC1=C(O)C2=C[C@@H](O)[C@H]3[C@@](C)(COC=O)CCC[C@]3(C)C2=C(O)C1=O

InChI Identifier

InChI=1S/C22H30O7/c1-12(28-4)8-14-17(25)13-9-15(24)20-21(2,10-29-11-23)6-5-7-22(20,3)16(13)19(27)18(14)26/h9,11-12,15,20,24-25,27H,5-8,10H2,1-4H3/t12-,15+,20-,21+,22+/m0/s1

InChI Key

LIJILMVGVVXBFG-KAWGCRPPSA-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
Plectranthus lanuginosus	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

Abeoabietane diterpenoid
Diterpenoid
Hydrophenanthrene
Phenanthrene
Vinylogous acid
Carboxylic acid ester
Ketone
Cyclic ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Enol
Dialkyl ether
Polyol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
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	1.15	ChemAxon
pKa (Strongest Acidic)	5.52	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	109.3 m³·mol⁻¹	ChemAxon
Polarizability	43.16 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	Yes	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

163027766

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate (NP0321354)

MOL for NP0321354 ([(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate)

3D MOL for NP0321354 ([(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate)

3D SDF for NP0321354 ([(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate)

3D-SDF for NP0321354 ([(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate)

PDB for NP0321354 ([(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate)

3D PDB for NP0321354 ([(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate)

SMILES for NP0321354 ([(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate)

INCHI for NP0321354 ([(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate)

Structure for NP0321354 ([(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate)

3D Structure for NP0321354 ([(1s,4as,10r,10ar)-5,8,10-trihydroxy-7-[(2s)-2-methoxypropyl]-1,4a-dimethyl-6-oxo-3,4,10,10a-tetrahydro-2h-phenanthren-1-yl]methyl formate)