NP-MRD: Showing NP-Card for methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate (NP0227508)

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Record Information

Version

2.0

Created at

2022-09-06 06:50:56 UTC

Updated at

2022-09-06 06:50:57 UTC

NP-MRD ID

NP0227508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate

Description

Methyl 10-(acetyloxy)-5,9-dihydroxy-1,4a-dimethyl-2-oxo-7-(propan-2-yl)-1,2,4a,9,10,10a-hexahydrophenanthrene-1-carboxylate belongs to the class of organic compounds known as 1-hydroxysteroids. These are steroids carrying a hydroxyl group at the 1-position of the steroid backbone. methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate is found in Chaiturus marrubiastrum. Methyl 10-(acetyloxy)-5,9-dihydroxy-1,4a-dimethyl-2-oxo-7-(propan-2-yl)-1,2,4a,9,10,10a-hexahydrophenanthrene-1-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161519272D          

 30 32  0  0  0  0            999 V2000
    0.7516    1.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269    0.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6701    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0382   -0.3587    0.0000 O   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
    2.5886    0.7019    0.0000 C   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
    3.2704    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    1.3184    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
    2.0329    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  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  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   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   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    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
    4.0954   -1.5395    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
    2.4454   -1.5395    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
    1.2079   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -1.5395    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  2  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    4.8534    0.1063    2.9890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605   -0.4619    1.7813 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0837   -0.1999    1.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786    0.5659    1.9971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190   -0.7656    0.0590 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4447   -0.4975   -1.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5153   -2.2538    0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0977   -2.8033    1.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8231   -3.0599   -0.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8036   -2.5186   -1.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085   -1.1639   -1.1197 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2460   -0.5226   -2.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0795   -1.0379   -0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9379   -2.0836   -0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260   -3.3583   -0.9957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2469   -1.8977   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6390   -0.6490    0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0320   -0.4712    0.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7583    0.6093    0.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0512   -0.0141    2.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371    0.3887    0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4484    0.2153   -0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5807    1.3984   -0.2041 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1095    2.3973   -0.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814    1.0855   -0.5423 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6976    2.0516    0.0308 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3958    2.9909   -0.7134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2656    4.0179   -0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707    2.9501   -1.9643 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1300   -0.3287   -0.1564 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4149   -0.6524    3.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5871    0.9093    2.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0513    0.5672    3.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1769    0.3724   -1.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -1.4258   -1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4489   -0.3020   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1123   -4.0644   -0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3152   -3.1363   -2.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5392    0.2527   -2.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1554   -1.3574   -3.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2078   -0.2738   -2.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2834   -4.1066   -0.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9409   -2.7291   -0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5869   -1.4260    0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4718    1.6185    0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4400    0.5091   -1.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8550    0.4632    0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2846   -0.5356    2.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0710   -0.2512    2.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9677    1.0792    2.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    1.3721    0.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545    1.7700    0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4244    3.0434   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9300    1.2401   -1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6627    3.6454    0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0692    4.2406   -0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6505    4.9395    0.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6240   -0.4518    0.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  1
  5  6  1  0
  5 30  1  0
 30 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 25 23  1  0
 23 24  1  0
 23 22  1  0
 22 21  2  0
 21 17  1  0
 17 16  2  0
 16 14  1  0
 14 15  1  0
 14 13  2  0
 13 11  1  0
 11 12  1  6
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  7  5  1  0
 11 30  1  0
 13 22  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  6 35  1  0
  6 36  1  0
 30 58  1  1
 25 54  1  6
 28 55  1  0
 28 56  1  0
 28 57  1  0
 23 52  1  1
 24 53  1  0
 21 51  1  0
 16 43  1  0
 15 42  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 10 38  1  0
  9 37  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
M  END


  Mrv1533004161519272D          

 30 32  0  0  0  0            999 V2000
    0.7516    1.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269    0.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6701    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0382   -0.3587    0.0000 O   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
    2.5886    0.7019    0.0000 C   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
    3.2704    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    1.3184    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
    2.0329    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  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  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   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   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    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
    4.0954   -1.5395    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
    2.4454   -1.5395    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
    1.2079   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -1.5395    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  2  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(C)C2C(OC(C)=O)C(O)C3=CC(=CC(O)=C3C2(C)C=CC1=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O7/c1-11(2)13-9-14-17(15(25)10-13)22(4)8-7-16(26)23(5,21(28)29-6)20(22)19(18(14)27)30-12(3)24/h7-11,18-20,25,27H,1-6H3

> <INCHI_KEY>
ROWKODQLOIEBHL-UHFFFAOYSA-N

> <FORMULA>
C23H28O7

> <MOLECULAR_WEIGHT>
416.47

> <EXACT_MASS>
416.183503242

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.41541482501339

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 10-(acetyloxy)-5,9-dihydroxy-1,4a-dimethyl-2-oxo-7-(propan-2-yl)-1,2,4a,9,10,10a-hexahydrophenanthrene-1-carboxylate

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
3.134998057

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.526302679627488

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.166073482114527

> <JCHEM_PKA_STRONGEST_BASIC>
-3.513814770264557

> <JCHEM_POLAR_SURFACE_AREA>
110.13

> <JCHEM_REFRACTIVITY>
109.93199999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9H-phenanthrene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.403   2.364   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.850   1.837   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.118   0.320   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.938  -0.670   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.832   1.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.105   2.461   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.565   2.461   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.795   1.127   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.795   3.795   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.185   2.461   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.415  -4.207   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.645  -2.874   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.255  -1.540   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.035  -1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.805  -0.206   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.805  -2.874   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   26                                             
CONECT    6    5                                                            
CONECT    7    5    8   22                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   15   22                                                  
CONECT   22   21    7   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    5   27                                                  
CONECT   27   26                                                            
CONECT   28   17   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
Methyl 10-(acetyloxy)-5,9-dihydroxy-1,4a-dimethyl-2-oxo-7-(propan-2-yl)-1,2,4a,9,10,10a-hexahydrophenanthrene-1-carboxylic acid	Generator

Chemical Formula

C₂₃H₂₈O₇

Average Mass

416.4700 Da

Monoisotopic Mass

416.18350 Da

IUPAC Name

methyl 10-(acetyloxy)-5,9-dihydroxy-1,4a-dimethyl-2-oxo-7-(propan-2-yl)-1,2,4a,9,10,10a-hexahydrophenanthrene-1-carboxylate

Traditional Name

methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9H-phenanthrene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(C)C2C(OC(C)=O)C(O)C3=CC(=CC(O)=C3C2(C)C=CC1=O)C(C)C

InChI Identifier

InChI=1S/C23H28O7/c1-11(2)13-9-14-17(15(25)10-13)22(4)8-7-16(26)23(5,21(28)29-6)20(22)19(18(14)27)30-12(3)24/h7-11,18-20,25,27H,1-6H3

InChI Key

ROWKODQLOIEBHL-UHFFFAOYSA-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
Leonurus marrubiastrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxysteroids. These are steroids carrying a hydroxyl group at the 1-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

1-hydroxysteroids

Alternative Parents

Substituents

Abietane diterpenoid
Diterpenoid
6-hydroxysteroid
1-hydroxysteroid
Hydrophenanthrene
Phenanthrene
Tetralin
Cyclohexenone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Dicarboxylic acid or derivatives
Methyl ester
Carboxylic acid ester
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid derivative
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	2.91	ALOGPS
logP	3.13	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.93 m³·mol⁻¹	ChemAxon
Polarizability	43.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

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

76551307

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate (NP0227508)

MOL for NP0227508 (methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

3D MOL for NP0227508 (methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

3D SDF for NP0227508 (methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

3D-SDF for NP0227508 (methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

PDB for NP0227508 (methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

3D PDB for NP0227508 (methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

SMILES for NP0227508 (methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

INCHI for NP0227508 (methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

Structure for NP0227508 (methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

3D Structure for NP0227508 (methyl 10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)