NP-MRD: Showing NP-Card for methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate (NP0144443)

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Record Information

Version

2.0

Created at

2022-09-01 23:25:01 UTC

Updated at

2022-09-01 23:25:01 UTC

NP-MRD ID

NP0144443

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate

Description

11Beta-Acetoxy-3,7-dioxo-6-hydroxy-12alpha-(2-methylpropanoyloxy)meliaca-1,5,14-trien-25-oic acid methyl ester belongs to the class of organic compounds known as 17-furanylsteroids and derivatives. These are steroidal compounds having a furanyl group linked to the steroid backbone at the C17 position. methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate is found in Trichilia hirta. Based on a literature review very few articles have been published on 11beta-Acetoxy-3,7-dioxo-6-hydroxy-12alpha-(2-methylpropanoyloxy)meliaca-1,5,14-trien-25-oic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022201252D          

 43 47  0  0  1  0            999 V2000
    1.1526    1.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8661    1.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8641    0.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486   -0.0456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8616    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6412    1.2123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655    0.9219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5458    0.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4373   -2.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2618   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5421   -2.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8908   -3.2859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2080   -2.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4662   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8548   -2.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1743   -3.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940   -3.1493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6033   -4.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4154   -4.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0715   -4.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2306   -2.5221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109   -3.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230   -3.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9791   -3.9287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  2  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
  5  3  1  6  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  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  6  0  0  0
 11 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
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 25 26  2  0  0  0  0
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 24 28  2  0  0  0  0
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 20 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
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 35 37  1  0  0  0  0
 31 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 43 38  1  6  0  0  0
 11 43  1  0  0  0  0
 18 43  1  0  0  0  0
M  END

     RDKit          3D

 81 85  0  0  0  0  0  0  0  0999 V2000
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    5.7704   -0.0796   -0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6759    0.4862   -1.1012 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5883   -0.6793   -0.9997 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6942   -0.5228   -2.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4014   -2.1208   -0.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2752   -2.8796   -0.2268 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0953   -2.6701   -1.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0146   -1.9827   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1511   -0.6675   -0.0195 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.9953    2.0522    0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0722    1.8012   -0.6746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8795    1.9115   -1.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5615    1.4136   -0.6575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6048    0.8867   -2.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5677    0.2763    0.3001 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6990   -0.5178   -0.0337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6979   -0.8845    0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6339   -0.4991    2.0131 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3629    1.4119    2.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320    2.9876    1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1358    1.8354    1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    4.2414   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2221    2.9743   -2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    4.4715   -1.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
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  5  3  1  1
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 15 55  1  0
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M  END


  Mrv1652309022201252D          

 43 47  0  0  1  0            999 V2000
    1.1526    1.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8661    1.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8641    0.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486   -0.0456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8616    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6412    1.2123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655    0.9219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5458    0.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4373   -2.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2618   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5421   -2.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8908   -3.2859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2080   -2.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4662   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8548   -2.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1743   -3.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940   -3.1493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6033   -4.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4154   -4.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0715   -4.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2306   -2.5221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109   -3.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230   -3.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9791   -3.9287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  2  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
  5  3  1  6  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  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  6  0  0  0
 11 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
 23 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 31 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 43 38  1  6  0  0  0
 11 43  1  0  0  0  0
 18 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0144443

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(C)C(=O)C=C[C@]2(C)[C@H]3[C@@H](OC(C)=O)[C@H](OC(=O)C(C)C)[C@@]4(C)[C@@H](CC=C4[C@]3(C)C(=O)C(O)=C12)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H38O10/c1-16(2)28(38)43-27-23(42-17(3)34)25-30(4)13-11-21(35)33(7,29(39)40-8)24(30)22(36)26(37)32(25,6)20-10-9-19(31(20,27)5)18-12-14-41-15-18/h10-16,19,23,25,27,36H,9H2,1-8H3/t19-,23+,25+,27-,30-,31-,32-,33-/m0/s1

> <INCHI_KEY>
WGOAIFKCEHANND-BYVQRJCNSA-N

> <FORMULA>
C33H38O10

> <MOLECULAR_WEIGHT>
594.657

> <EXACT_MASS>
594.246497424

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
61.60665692914121

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2R,6R,10R,14R,15S,16R,17R)-17-(acetyloxy)-14-(furan-3-yl)-8-hydroxy-2,6,10,15-tetramethyl-16-[(2-methylpropanoyl)oxy]-5,9-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7,11-triene-6-carboxylate

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
4.198252277

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.016723780407629

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8767432245757405

> <JCHEM_POLAR_SURFACE_AREA>
146.41

> <JCHEM_REFRACTIVITY>
155.01650000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2R,6R,10R,14R,15S,16R,17R)-17-(acetyloxy)-14-(furan-3-yl)-8-hydroxy-2,6,10,15-tetramethyl-16-[(2-methylpropanoyl)oxy]-5,9-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7,11-triene-6-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       2.152   2.995   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.483   2.222   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.480   0.682   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.144  -0.085   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.342   1.354   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.303  -0.998   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.797   2.263   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.829   1.721   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.352   0.273   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.883  -3.790   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.422  -3.740   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.945  -5.188   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.730  -6.134   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.455  -5.269   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.929  -5.250   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.659  -7.019   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.829  -5.879   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.460  -7.876   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.975  -8.147   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.467  -9.053   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       7.897  -4.708   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       8.420  -6.156   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.936  -6.427   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       7.428  -7.334   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       8.367  -2.082   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   13                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   43                                             
CONECT   12   11                                                            
CONECT   13   11    5   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   43                                             
CONECT   19   18                                                            
CONECT   20   18   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29   23   20   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32   38                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   31   39   43                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   38   11   18                                                  
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
11b-Acetoxy-3,7-dioxo-6-hydroxy-12a-(2-methylpropanoyloxy)meliaca-1,5,14-trien-25-Oate methyl ester	Generator
11b-Acetoxy-3,7-dioxo-6-hydroxy-12a-(2-methylpropanoyloxy)meliaca-1,5,14-trien-25-Oic acid methyl ester	Generator
11beta-Acetoxy-3,7-dioxo-6-hydroxy-12alpha-(2-methylpropanoyloxy)meliaca-1,5,14-trien-25-Oate methyl ester	Generator
11Β-acetoxy-3,7-dioxo-6-hydroxy-12α-(2-methylpropanoyloxy)meliaca-1,5,14-trien-25-Oate methyl ester	Generator
11Β-acetoxy-3,7-dioxo-6-hydroxy-12α-(2-methylpropanoyloxy)meliaca-1,5,14-trien-25-Oic acid methyl ester	Generator

Chemical Formula

C₃₃H₃₈O₁₀

Average Mass

594.6570 Da

Monoisotopic Mass

594.24650 Da

IUPAC Name

methyl (1R,2R,6R,10R,14R,15S,16R,17R)-17-(acetyloxy)-14-(furan-3-yl)-8-hydroxy-2,6,10,15-tetramethyl-16-[(2-methylpropanoyl)oxy]-5,9-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7,11-triene-6-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(C)C(=O)C=C[C@]2(C)[C@H]3[C@@H](OC(C)=O)[C@H](OC(=O)C(C)C)[C@@]4(C)[C@@H](CC=C4[C@]3(C)C(=O)C(O)=C12)C1=COC=C1

InChI Identifier

InChI=1S/C33H38O10/c1-16(2)28(38)43-27-23(42-17(3)34)25-30(4)13-11-21(35)33(7,29(39)40-8)24(30)22(36)26(37)32(25,6)20-10-9-19(31(20,27)5)18-12-14-41-15-18/h10-16,19,23,25,27,36H,9H2,1-8H3/t19-,23+,25+,27-,30-,31-,32-,33-/m0/s1

InChI Key

WGOAIFKCEHANND-BYVQRJCNSA-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
Trichilia hirta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 17-furanylsteroids and derivatives. These are steroidal compounds having a furanyl group linked to the steroid backbone at the C17 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

17-furanylsteroids and derivatives

Direct Parent

17-furanylsteroids and derivatives

Alternative Parents

Substituents

17-furanylsteroid skeleton
Steroid ester
7-oxosteroid
7-hydroxysteroid
Oxosteroid
Hydroxysteroid
6-hydroxysteroid
3-oxosteroid
3-oxo-delta-1-steroid
Delta-1-steroid
Tricarboxylic acid or derivatives
Cyclohexenone
Heteroaromatic compound
Methyl ester
Furan
Cyclic ketone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Enol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.37	ALOGPS
logP	4.2	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.02	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	146.41 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	155.02 m³·mol⁻¹	ChemAxon
Polarizability	61.61 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

28944415

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15139229

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate (NP0144443)

MOL for NP0144443 (methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate)

3D MOL for NP0144443 (methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate)

3D SDF for NP0144443 (methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate)

3D-SDF for NP0144443 (methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate)

PDB for NP0144443 (methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate)

3D PDB for NP0144443 (methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate)

SMILES for NP0144443 (methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate)

INCHI for NP0144443 (methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate)

Structure for NP0144443 (methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate)

3D Structure for NP0144443 (methyl (1s,3br,6r,9ar,9br,10r,11r,11as)-10-(acetyloxy)-1-(furan-3-yl)-5-hydroxy-3b,6,9a,11a-tetramethyl-11-[(2-methylpropanoyl)oxy]-4,7-dioxo-1h,2h,9bh,10h,11h-cyclopenta[a]phenanthrene-6-carboxylate)