NP-MRD: Showing NP-Card for tenuifolin C (NP0043239)

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Record Information

Version

1.0

Created at

2021-06-21 00:42:19 UTC

Updated at

2021-06-30 00:18:49 UTC

NP-MRD ID

NP0043239

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tenuifolin C

Provided By

JEOL Database JEOL Logo

Description

Tenuifolin C belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. tenuifolin C is found in Isodon tenuifolius. It was first documented in 2009 (PMID: 19754130). Based on a literature review a significant number of articles have been published on tenuifolin C (PMID: 29017076) (PMID: 27888133) (PMID: 24702811) (PMID: 21042868) (PMID: 31836776) (PMID: 27912882).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102423D          

 70 73  0  0  0  0            999 V2000
    1.4655    3.0507    3.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1110    2.4294    2.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0979    2.9543    1.5384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3186    2.4809    1.8524 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4792    0.9494    1.9332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2740    0.5353    3.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3423    0.6009    4.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9476    0.1261    5.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4628    0.9856    3.8434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045    0.0792    1.0614 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.5449    2.2871    0.2526 C   0  0  2  0  0  0  0  0  0  0  0  0
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 33 68  1  0  0  0  0
 33 69  1  0  0  0  0
 33 70  1  0  0  0  0
M  END

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
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    1.1110    2.4294    2.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 68  1  0
 33 69  1  0
 33 70  1  0
M  END


  Mrv1652306212102423D          

 70 73  0  0  0  0            999 V2000
    1.4655    3.0507    3.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1110    2.4294    2.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0979    2.9543    1.5384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3186    2.4809    1.8524 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4792    0.9494    1.9332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2740    0.5353    3.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3423    0.6009    4.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9476    0.1261    5.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4628    0.9856    3.8434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045    0.0792    1.0614 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8270    0.8461    0.7225 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5449    2.2871    0.2526 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7082    0.2246   -0.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677    0.6154   -0.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1032   -0.7175   -1.3607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0080   -1.5943   -0.7772 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4267   -2.7681   -1.7429 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7923   -3.6986   -2.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018   -2.2899   -3.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -3.6212   -1.0698 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9928   -4.2961    0.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7088   -2.7838   -0.6077 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2921   -1.6982    0.3940 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5018   -0.9722    0.7108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2716   -1.4744    1.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5101   -0.6475    1.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0203   -2.4807    2.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752   -0.7184   -0.1561 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8172    0.2724   -1.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    1.1228    2.0032 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5830    0.1595    3.0602 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750   -1.0442    2.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0177   -1.8962    4.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7238   -1.4068    1.8340 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2165    2.6265    4.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0139    3.9925    3.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1312    4.0453    1.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9782    2.8517    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6595    2.9520    2.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5137    0.7429    1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8105    0.1874    6.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1523    0.7617    5.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189   -0.9150    5.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2004   -0.7475    1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502    2.7762   -0.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046    2.3583   -0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7608   -0.1246   -2.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9305   -1.3408   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4501   -2.1044    0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3030   -3.9706   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5304   -3.2324   -2.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4766   -4.6282   -2.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1212   -3.1481   -3.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1350   -1.6976   -3.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119   -1.6935   -3.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8827   -4.3949   -1.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6878   -4.8747    0.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2403   -2.3428   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4450   -3.4396   -0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9012   -2.1763    1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9166   -0.8018    2.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2500   -0.9449    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2742    0.4147    1.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5095   -0.2188   -1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4088    1.0354   -0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854    0.7996   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544    1.2908    1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4343   -1.3806    4.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638   -2.8336    3.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9604   -2.1233    4.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 29  1  6  0  0  0
 15 13  1  0  0  0  0
 17 19  1  6  0  0  0
 11 13  1  6  0  0  0
  5  6  1  0  0  0  0
 17 16  1  0  0  0  0
 20 21  1  0  0  0  0
 28 23  1  0  0  0  0
 10 44  1  1  0  0  0
 10 11  1  0  0  0  0
 11 30  1  0  0  0  0
 28 16  1  0  0  0  0
  3  2  1  0  0  0  0
 30  2  1  0  0  0  0
 11 12  1  0  0  0  0
  2  1  2  3  0  0  0
 23 24  1  0  0  0  0
 12  3  1  0  0  0  0
 24 25  1  0  0  0  0
 22 20  1  0  0  0  0
 25 27  2  0  0  0  0
  3  4  1  0  0  0  0
 25 26  1  0  0  0  0
 22 23  1  0  0  0  0
  6  7  1  0  0  0  0
  4  5  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
 20 17  1  0  0  0  0
 13 14  2  0  0  0  0
 16 49  1  1  0  0  0
 30 31  1  0  0  0  0
 28 10  1  0  0  0  0
 31 32  1  0  0  0  0
 17 18  1  0  0  0  0
 32 34  2  0  0  0  0
 16 15  1  0  0  0  0
 32 33  1  0  0  0  0
 22 58  1  0  0  0  0
 22 59  1  0  0  0  0
 20 56  1  6  0  0  0
 23 60  1  1  0  0  0
 15 47  1  0  0  0  0
 15 48  1  0  0  0  0
 12 45  1  0  0  0  0
 12 46  1  0  0  0  0
  3 37  1  6  0  0  0
  4 38  1  0  0  0  0
  4 39  1  0  0  0  0
  5 40  1  6  0  0  0
 18 50  1  0  0  0  0
 18 51  1  0  0  0  0
 18 52  1  0  0  0  0
 29 64  1  0  0  0  0
 29 65  1  0  0  0  0
 29 66  1  0  0  0  0
 19 53  1  0  0  0  0
 19 54  1  0  0  0  0
 19 55  1  0  0  0  0
 21 57  1  0  0  0  0
 30 67  1  6  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
 26 61  1  0  0  0  0
 26 62  1  0  0  0  0
 26 63  1  0  0  0  0
  8 41  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
 33 68  1  0  0  0  0
 33 69  1  0  0  0  0
 33 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043239

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2(C([H])([H])[H])[C@]([H])(C([H])([H])C(=O)[C@]34C([H])([H])[C@]([H])(C(=C([H])[H])[C@@]3([H])OC(=O)C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]24[H])C1(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O8/c1-12-16-8-17(32-13(2)27)22-25(7)18(24(5,6)19(30)10-21(25)33-14(3)28)9-20(31)26(22,11-16)23(12)34-15(4)29/h16-19,21-23,30H,1,8-11H2,2-7H3/t16-,17+,18-,19+,21+,22+,23-,25+,26+/m1/s1

> <INCHI_KEY>
VTAYJHOHGSJXDY-BSLCUUFRSA-N

> <FORMULA>
C26H36O8

> <MOLECULAR_WEIGHT>
476.566

> <EXACT_MASS>
476.241018119

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.26604373483649

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,6S,8S,9R,10S,11S,13S,15R)-8,11-bis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidene-2-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-yl acetate

> <ALOGPS_LOGP>
1.99

> <JCHEM_LOGP>
1.3541464910000003

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.47529662348817

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.62359922935413

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9633752950397065

> <JCHEM_POLAR_SURFACE_AREA>
116.20000000000002

> <JCHEM_REFRACTIVITY>
119.73550000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,6S,8S,9R,10S,11S,13S,15R)-8,11-bis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidene-2-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
    1.4655    3.0507    3.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1110    2.4294    2.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0979    2.9543    1.5384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3186    2.4809    1.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    0.9494    1.9332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2740    0.5353    3.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3423    0.6009    4.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9476    0.1261    5.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4628    0.9856    3.8434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045    0.0792    1.0614 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8270    0.8461    0.7225 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5449    2.2871    0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7082    0.2246   -0.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677    0.6154   -0.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1032   -0.7175   -1.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080   -1.5943   -0.7772 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4267   -2.7681   -1.7429 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7923   -3.6986   -2.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018   -2.2899   -3.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -3.6212   -1.0698 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9928   -4.2961    0.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7088   -2.7838   -0.6077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2921   -1.6982    0.3940 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5018   -0.9722    0.7108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2716   -1.4744    1.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5101   -0.6475    1.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0203   -2.4807    2.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752   -0.7184   -0.1561 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8172    0.2724   -1.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    1.1228    2.0032 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5830    0.1595    3.0602 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750   -1.0442    2.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0177   -1.8962    4.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7238   -1.4068    1.8340 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2165    2.6265    4.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0139    3.9925    3.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1312    4.0453    1.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9782    2.8517    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6595    2.9520    2.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5137    0.7429    1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8105    0.1874    6.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1523    0.7617    5.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189   -0.9150    5.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2004   -0.7475    1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502    2.7762   -0.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046    2.3583   -0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7608   -0.1246   -2.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9305   -1.3408   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4501   -2.1044    0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3030   -3.9706   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5304   -3.2324   -2.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4766   -4.6282   -2.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1212   -3.1481   -3.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1350   -1.6976   -3.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119   -1.6935   -3.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8827   -4.3949   -1.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6878   -4.8747    0.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2403   -2.3428   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4450   -3.4396   -0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9012   -2.1763    1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9166   -0.8018    2.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2500   -0.9449    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2742    0.4147    1.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5095   -0.2188   -1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4088    1.0354   -0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854    0.7996   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544    1.2908    1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4343   -1.3806    4.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638   -2.8336    3.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9604   -2.1233    4.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 29  1  6
 15 13  1  0
 17 19  1  6
 11 13  1  6
  5  6  1  0
 17 16  1  0
 20 21  1  0
 28 23  1  0
 10 44  1  1
 10 11  1  0
 11 30  1  0
 28 16  1  0
  3  2  1  0
 30  2  1  0
 11 12  1  0
  2  1  2  3
 23 24  1  0
 12  3  1  0
 24 25  1  0
 22 20  1  0
 25 27  2  0
  3  4  1  0
 25 26  1  0
 22 23  1  0
  6  7  1  0
  4  5  1  0
  7  9  2  0
  5 10  1  0
  7  8  1  0
 20 17  1  0
 13 14  2  0
 16 49  1  1
 30 31  1  0
 28 10  1  0
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 17 18  1  0
 32 34  2  0
 16 15  1  0
 32 33  1  0
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 12 45  1  0
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  3 37  1  6
  4 38  1  0
  4 39  1  0
  5 40  1  6
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 30 67  1  6
  1 35  1  0
  1 36  1  0
 26 61  1  0
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 26 63  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
 33 68  1  0
 33 69  1  0
 33 70  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       1.466   3.051   3.655  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.111   2.429   2.521  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.098   2.954   1.538  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.319   2.481   1.852  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.479   0.949   1.933  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.274   0.535   3.309  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.342   0.601   4.147  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.948   0.126   5.511  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.463   0.986   3.843  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.504   0.079   1.061  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.827   0.846   0.723  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.545   2.287   0.253  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.708   0.225  -0.355  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.868   0.615  -0.531  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.103  -0.718  -1.361  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.008  -1.594  -0.777  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.427  -2.768  -1.743  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.792  -3.699  -2.003  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.902  -2.290  -3.130  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.532  -3.621  -1.070  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.993  -4.296   0.069  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.709  -2.784  -0.608  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.292  -1.698   0.394  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.502  -0.972   0.711  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.272  -1.474   1.719  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.510  -0.648   1.884  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.020  -2.481   2.368  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.175  -0.718  -0.156  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.817   0.272  -1.152  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.694   1.123   2.003  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.583   0.160   3.060  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.175  -1.044   2.862  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.018  -1.896   4.084  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.724  -1.407   1.834  0.00  0.00           O+0
HETATM   35  H   UNK     0       2.216   2.627   4.314  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.014   3.993   3.950  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.131   4.045   1.450  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.978   2.852   1.057  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.660   2.952   2.783  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.514   0.743   1.678  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.811   0.187   6.180  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.152   0.762   5.908  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.619  -0.915   5.460  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.200  -0.748   1.718  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.450   2.776  -0.135  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.205   2.358  -0.538  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.761  -0.125  -2.213  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.931  -1.341  -1.714  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.450  -2.104   0.086  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.303  -3.971  -1.073  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.530  -3.232  -2.664  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.477  -4.628  -2.492  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.121  -3.148  -3.778  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.135  -1.698  -3.640  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.812  -1.694  -3.094  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.883  -4.395  -1.764  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.688  -4.875   0.432  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.240  -2.343  -1.458  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.445  -3.440  -0.125  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.901  -2.176   1.302  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.917  -0.802   2.887  0.00  0.00           H+0
HETATM   62  H   UNK     0      -6.250  -0.945   1.137  0.00  0.00           H+0
HETATM   63  H   UNK     0      -5.274   0.415   1.776  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.510  -0.219  -1.838  0.00  0.00           H+0
HETATM   65  H   UNK     0      -2.409   1.035  -0.636  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.085   0.800  -1.765  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.754   1.291   1.778  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.434  -1.381   4.953  0.00  0.00           H+0
HETATM   69  H   UNK     0       2.564  -2.834   3.945  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.960  -2.123   4.241  0.00  0.00           H+0
CONECT    1    2   35   36                                                  
CONECT    2    3   30    1                                                  
CONECT    3    2   12    4   37                                             
CONECT    4    3    5   38   39                                             
CONECT    5    6    4   10   40                                             
CONECT    6    5    7                                                       
CONECT    7    6    9    8                                                  
CONECT    8    7   41   42   43                                             
CONECT    9    7                                                            
CONECT   10   44   11    5   28                                             
CONECT   11   13   10   30   12                                             
CONECT   12   11    3   45   46                                             
CONECT   13   15   11   14                                                  
CONECT   14   13                                                            
CONECT   15   13   16   47   48                                             
CONECT   16   17   28   49   15                                             
CONECT   17   19   16   20   18                                             
CONECT   18   17   50   51   52                                             
CONECT   19   17   53   54   55                                             
CONECT   20   21   22   17   56                                             
CONECT   21   20   57                                                       
CONECT   22   20   23   58   59                                             
CONECT   23   28   24   22   60                                             
CONECT   24   23   25                                                       
CONECT   25   24   27   26                                                  
CONECT   26   25   61   62   63                                             
CONECT   27   25                                                            
CONECT   28   29   23   16   10                                             
CONECT   29   28   64   65   66                                             
CONECT   30   11    2   31   67                                             
CONECT   31   30   32                                                       
CONECT   32   31   34   33                                                  
CONECT   33   32   68   69   70                                             
CONECT   34   32                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44   10                                                            
CONECT   45   12                                                            
CONECT   46   12                                                            
CONECT   47   15                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   19                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   22                                                            
CONECT   60   23                                                            
CONECT   61   26                                                            
CONECT   62   26                                                            
CONECT   63   26                                                            
CONECT   64   29                                                            
CONECT   65   29                                                            
CONECT   66   29                                                            
CONECT   67   30                                                            
CONECT   68   33                                                            
CONECT   69   33                                                            
CONECT   70   33                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  146    0
END

RDKit          3D

70 73  0  0  0  0  0  0  0  0999 V2000
    1.4655    3.0507    3.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1110    2.4294    2.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0979    2.9543    1.5384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3186    2.4809    1.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    0.9494    1.9332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2740    0.5353    3.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3423    0.6009    4.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9476    0.1261    5.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4628    0.9856    3.8434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045    0.0792    1.0614 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8270    0.8461    0.7225 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5449    2.2871    0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7082    0.2246   -0.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677    0.6154   -0.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1032   -0.7175   -1.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0080   -1.5943   -0.7772 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4267   -2.7681   -1.7429 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7923   -3.6986   -2.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018   -2.2899   -3.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -3.6212   -1.0698 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9928   -4.2961    0.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7088   -2.7838   -0.6077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2921   -1.6982    0.3940 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5018   -0.9722    0.7108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2716   -1.4744    1.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5101   -0.6475    1.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0203   -2.4807    2.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752   -0.7184   -0.1561 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8172    0.2724   -1.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    1.1228    2.0032 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5830    0.1595    3.0602 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750   -1.0442    2.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0177   -1.8962    4.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7238   -1.4068    1.8340 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2165    2.6265    4.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0139    3.9925    3.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1312    4.0453    1.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9782    2.8517    1.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6595    2.9520    2.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5137    0.7429    1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8105    0.1874    6.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1523    0.7617    5.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189   -0.9150    5.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2004   -0.7475    1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502    2.7762   -0.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046    2.3583   -0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7608   -0.1246   -2.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9305   -1.3408   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4501   -2.1044    0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3030   -3.9706   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5304   -3.2324   -2.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4766   -4.6282   -2.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1212   -3.1481   -3.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1350   -1.6976   -3.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119   -1.6935   -3.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8827   -4.3949   -1.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6878   -4.8747    0.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2403   -2.3428   -1.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4450   -3.4396   -0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9012   -2.1763    1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9166   -0.8018    2.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2500   -0.9449    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2742    0.4147    1.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5095   -0.2188   -1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4088    1.0354   -0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854    0.7996   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544    1.2908    1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4343   -1.3806    4.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638   -2.8336    3.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9604   -2.1233    4.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 29  1  6
 15 13  1  0
 17 19  1  6
 11 13  1  6
  5  6  1  0
 17 16  1  0
 20 21  1  0
 28 23  1  0
 10 44  1  1
 10 11  1  0
 11 30  1  0
 28 16  1  0
  3  2  1  0
 30  2  1  0
 11 12  1  0
  2  1  2  3
 23 24  1  0
 12  3  1  0
 24 25  1  0
 22 20  1  0
 25 27  2  0
  3  4  1  0
 25 26  1  0
 22 23  1  0
  6  7  1  0
  4  5  1  0
  7  9  2  0
  5 10  1  0
  7  8  1  0
 20 17  1  0
 13 14  2  0
 16 49  1  1
 30 31  1  0
 28 10  1  0
 31 32  1  0
 17 18  1  0
 32 34  2  0
 16 15  1  0
 32 33  1  0
 22 58  1  0
 22 59  1  0
 20 56  1  6
 23 60  1  1
 15 47  1  0
 15 48  1  0
 12 45  1  0
 12 46  1  0
  3 37  1  6
  4 38  1  0
  4 39  1  0
  5 40  1  6
 18 50  1  0
 18 51  1  0
 18 52  1  0
 29 64  1  0
 29 65  1  0
 29 66  1  0
 19 53  1  0
 19 54  1  0
 19 55  1  0
 21 57  1  0
 30 67  1  6
  1 35  1  0
  1 36  1  0
 26 61  1  0
 26 62  1  0
 26 63  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
 33 68  1  0
 33 69  1  0
 33 70  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆O₈

Average Mass

476.5660 Da

Monoisotopic Mass

476.24102 Da

IUPAC Name

(1S,4R,6S,8S,9R,10S,11S,13S,15R)-8,11-bis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidene-2-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-yl acetate

Traditional Name

(1S,4R,6S,8S,9R,10S,11S,13S,15R)-8,11-bis(acetyloxy)-6-hydroxy-5,5,9-trimethyl-14-methylidene-2-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2(C([H])([H])[H])[C@]([H])(C([H])([H])C(=O)[C@]34C([H])([H])[C@]([H])(C(=C([H])[H])[C@@]3([H])OC(=O)C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]24[H])C1(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C26H36O8/c1-12-16-8-17(32-13(2)27)22-25(7)18(24(5,6)19(30)10-21(25)33-14(3)28)9-20(31)26(22,11-16)23(12)34-15(4)29/h16-19,21-23,30H,1,8-11H2,2-7H3/t16-,17+,18-,19+,21+,22+,23-,25+,26+/m1/s1

InChI Key

VTAYJHOHGSJXDY-BSLCUUFRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isodon tenuifolius	JEOL database	Yang, J. -H., et al, J. Nat. Prod. 76, 256 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Tricarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.99	ALOGPS
logP	1.35	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	14.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	116.2 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	119.74 m³·mol⁻¹	ChemAxon
Polarizability	49.27 Å³	ChemAxon
Number of Rings	4	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

29415098

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71579050

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang C, Yin X, Dong X, Zhang X, You L, Wang W, Wang J, Chen Q, Ni J: Determination of the phytochemical composition of Jingning fang and the in vivo pharmacokinetics of its metabolites in rat plasma by UPLC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Nov 1;1067:71-88. doi: 10.1016/j.jchromb.2017.09.019. Epub 2017 Sep 21. [PubMed:29017076 ]
Fang J, Wang L, Wu T, Yang C, Gao L, Cai H, Liu J, Fang S, Chen Y, Tan W, Wang Q: Network pharmacology-based study on the mechanism of action for herbal medicines in Alzheimer treatment. J Ethnopharmacol. 2017 Jan 20;196:281-292. doi: 10.1016/j.jep.2016.11.034. Epub 2016 Nov 23. [PubMed:27888133 ]
Zhou YH, Zhang SY, Guo Q, Chai XY, Jiang Y, Tu PF: Chemical investigation of the roots of Polygala sibirica L. Chin J Nat Med. 2014 Mar;12(3):225-8. doi: 10.1016/S1875-5364(14)60038-8. [PubMed:24702811 ]
Arai M, Hayashi A, Sobou M, Ishida S, Kawachi T, Kotoku N, Kobayashi M: Anti-angiogenic effect of triterpenoidal saponins from Polygala senega. J Nat Med. 2011 Jan;65(1):149-56. doi: 10.1007/s11418-010-0477-7. Epub 2010 Nov 2. [PubMed:21042868 ]
Lin RJ, Cheng MJ, Huang JC, Lo WL, Yeh YT, Yen CM, Lu CM, Chen CY: Cytotoxic compounds from the stems of Cinnamomum tenuifolium. J Nat Prod. 2009 Oct;72(10):1816-24. doi: 10.1021/np900225p. [PubMed:19754130 ]
Yan H, Zheng ZD, Wu HF, Liu XC, Zhou A: A microemulsion high-performance liquid chromatography (MELC) method for the separation and determination of hydrolyzed tenuifolin in Radix Polygalae. Sci Rep. 2019 Dec 13;9(1):19108. doi: 10.1038/s41598-019-55416-z. [PubMed:31836776 ]
Cao Q, Jiang Y, Cui SY, Tu PF, Chen YM, Ma XL, Cui XY, Huang YL, Ding H, Song JZ, Yu B, Sheng ZF, Wang ZJ, Xu YP, Yang G, Ye H, Hu X, Zhang YH: Tenuifolin, a saponin derived from Radix Polygalae, exhibits sleep-enhancing effects in mice. Phytomedicine. 2016 Dec 15;23(14):1797-1805. doi: 10.1016/j.phymed.2016.10.015. Epub 2016 Nov 5. [PubMed:27912882 ]
Yang, J. -H., et al. (2013). Yang, J. -H., et al, J. Nat. Prod. 76, 256 (2013). J. Nat. Prod..

Showing NP-Card for tenuifolin C (NP0043239)

MOL for NP0043239 (tenuifolin C)

3D MOL for NP0043239 (tenuifolin C)

3D SDF for NP0043239 (tenuifolin C)

3D-SDF for NP0043239 (tenuifolin C)

PDB for NP0043239 (tenuifolin C)

3D PDB for NP0043239 (tenuifolin C)

SMILES for NP0043239 (tenuifolin C)

INCHI for NP0043239 (tenuifolin C)

Structure for NP0043239 (tenuifolin C)

3D Structure for NP0043239 (tenuifolin C)