NP-MRD: Showing NP-Card for angustific acid (NP0320061)

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Record Information

Version

2.0

Created at

2022-09-11 21:26:57 UTC

Updated at

2022-09-11 21:26:58 UTC

NP-MRD ID

NP0320061

Secondary Accession Numbers

None

Natural Product Identification

Common Name

angustific acid

Description

Angustific Acid A, also known as angustifate a, belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. angustific acid is found in Kadsura angustifolia. angustific acid was first documented in 2011 (PMID: 21232955). Based on a literature review very few articles have been published on Angustific Acid A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112223262D          

 34 38  0  0  1  0            999 V2000
    6.9346    2.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4350    1.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1267    1.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8781    1.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488    1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3002    1.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9708    1.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3810    2.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1324    2.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7104    2.9650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5664    1.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5590    0.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2366    1.5696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9589    0.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3716    1.7373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1729    0.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4688    1.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0715    1.9131    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0145    1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5446    1.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2838    2.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292    2.7146    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3568    2.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1367    1.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904    0.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372   -0.1699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4299    0.3581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790    3.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0037    2.5711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7240    2.9800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6059    2.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8592    2.1109    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4537    2.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 17 28  1  0  0  0  0
 23 29  1  1  0  0  0
 30 29  1  1  0  0  0
 16 30  1  6  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 11 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END

     RDKit          3D

 74 78  0  0  0  0  0  0  0  0999 V2000
    3.3686   -1.5613    1.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1529   -0.4603    0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3680    0.4283    0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8764    0.3225   -1.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0275    1.2193   -1.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2359    0.8959   -1.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2870    2.0076   -1.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6566   -0.4202   -1.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8737   -0.6554   -2.2080 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8315   -1.5169   -1.9060 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8975   -0.0074    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890    1.1809   -0.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3681    1.3540   -1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2709    0.6672    0.1011 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2367    1.4793    1.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7266    0.4890    0.0146 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3776    1.1807    1.1956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8684    1.4481    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3332    0.4584    0.0251 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7369    0.4306   -0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3261   -0.6825   -0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6085    1.6582   -0.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7240   -0.8876    0.1765 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2969   -1.7401    1.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2477   -1.2136    2.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0390   -0.5184    3.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5918   -0.7338    4.2161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515    0.3754    2.3749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1741   -1.4448   -1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2256   -0.9016   -0.0258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3607   -1.9225    0.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0516   -1.5032    0.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5767   -0.6080   -0.0462 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4751   -1.1597   -1.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4194   -1.7263    1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441   -2.3062    1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1462    0.0841    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844    1.4710    0.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0654    0.6128   -1.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0761   -0.7315   -1.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8388    2.2968   -0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2838    1.5899   -1.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9822    2.7519   -2.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3053    2.4540   -0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9078   -2.2835   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5483    1.9194   -0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0781    2.4171   -1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    0.8868   -2.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507    1.4454    1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1141    1.1864    2.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0388    2.5619    1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0893    1.0349   -0.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9162    2.1794    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3267    1.3870    2.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9996    2.5134    0.6513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8826    0.9432   -0.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8770   -1.6606   -0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4131   -0.6335   -0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3669    1.5905   -1.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1628    1.5971    0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0428    2.5757   -0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6847   -2.6979    1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3299   -2.1127    1.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3216   -2.1266    3.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1811   -0.6447    2.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1685   -0.8393   -2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1769   -2.5103   -1.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7483   -2.4760    1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0508   -1.0539    1.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6097   -2.4708    1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3422   -0.8282   -2.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4780   -1.0363   -1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6257   -2.2728   -1.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 20  1  0
 20 21  2  3
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 28  1  0
 28 26  1  0
 26 27  2  0
 26 25  1  0
 25 24  1  0
 23 24  1  1
 23 29  1  0
 30 29  1  6
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  6
 33 11  1  0
 11 12  2  0
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 13 14  1  0
 14 15  1  1
 14 16  1  0
 11  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
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  6  7  1  0
  6  8  1  0
  8 10  1  0
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 23 19  1  0
 30 23  1  0
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 19 56  1  6
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 25 64  1  0
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 31 68  1  0
 31 69  1  0
 32 70  1  0
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 34 72  1  0
 34 73  1  0
 34 74  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 15 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  6
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
 10 45  1  0
M  END


  Mrv1652309112223262D          

 34 38  0  0  1  0            999 V2000
    6.9346    2.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4350    1.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1267    1.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8781    1.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488    1.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3002    1.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9708    1.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3810    2.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1324    2.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7104    2.9650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5664    1.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5590    0.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3716    1.7373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1729    0.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4688    1.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8592    2.1109    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4537    2.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
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 18 19  1  0  0  0  0
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 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
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 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 17 28  1  0  0  0  0
 23 29  1  1  0  0  0
 30 29  1  1  0  0  0
 16 30  1  6  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 11 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0320061

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H]1C[C@H]2OC(=O)CC[C@@]11C[C@]11CC[C@]3(C)C(=CC[C@@]3(C)[C@H]21)C(=C)CC\C=C(\C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O4/c1-18(2)22-16-23-25-28(6)12-10-21(19(3)8-7-9-20(4)26(32)33)27(28,5)14-15-30(25)17-29(22,30)13-11-24(31)34-23/h9-10,22-23,25H,1,3,7-8,11-17H2,2,4-6H3,(H,32,33)/b20-9-/t22-,23-,25+,27-,28+,29-,30+/m1/s1

> <INCHI_KEY>
OEBCOPKBNAGZEV-PNVFSJBDSA-N

> <FORMULA>
C30H40O4

> <MOLECULAR_WEIGHT>
464.646

> <EXACT_MASS>
464.292659768

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.71187004418508

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-6-[(1R,3S,6S,10S,11S,12R,17R)-6,10-dimethyl-14-oxo-17-(prop-1-en-2-yl)-13-oxapentacyclo[10.4.2.0^{1,3}.0^{3,11}.0^{6,10}]octadec-7-en-7-yl]-2-methylhepta-2,6-dienoic acid

> <JCHEM_LOGP>
5.513006952333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.695677320380876

> <JCHEM_PKA_STRONGEST_BASIC>
-7.042464337973576

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
134.33369999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-6-[(1R,3S,6S,10S,11S,12R,17R)-6,10-dimethyl-14-oxo-17-(prop-1-en-2-yl)-13-oxapentacyclo[10.4.2.0^{1,3}.0^{3,11}.0^{6,10}]octadec-7-en-7-yl]-2-methylhepta-2,6-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      12.945   4.962   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.012   3.656   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.303   2.731   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.706   3.366   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.958   2.469   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.360   3.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.612   2.208   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.511   4.638   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      18.914   5.273   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      16.259   5.535   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.391   3.147   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.044   1.647   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.510   1.512   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.908   2.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.390   1.321   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.294   3.243   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.923   1.563   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.608   2.221   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.867   3.571   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.894   3.469   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.017   1.904   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.530   4.551   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.975   5.067   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.533   4.214   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.122   2.568   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.969   1.210   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.310  -0.317   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.536   0.668   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.001   6.247   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.607   4.799   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.951   5.563   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.598   5.440   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.071   3.940   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.180   5.120   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   33                                             
CONECT   15   14                                                            
CONECT   16   14   17   30                                                  
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19   24   29   30                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   17                                                       
CONECT   29   23   30                                                       
CONECT   30   29   16   23   31                                             
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   11   14   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Angustifate a	Generator

Chemical Formula

C₃₀H₄₀O₄

Average Mass

464.6460 Da

Monoisotopic Mass

464.29266 Da

IUPAC Name

(2Z)-6-[(1R,3S,6S,10S,11S,12R,17R)-6,10-dimethyl-14-oxo-17-(prop-1-en-2-yl)-13-oxapentacyclo[10.4.2.0^{1,3}.0^{3,11}.0^{6,10}]octadec-7-en-7-yl]-2-methylhepta-2,6-dienoic acid

Traditional Name

(2Z)-6-[(1R,3S,6S,10S,11S,12R,17R)-6,10-dimethyl-14-oxo-17-(prop-1-en-2-yl)-13-oxapentacyclo[10.4.2.0^{1,3}.0^{3,11}.0^{6,10}]octadec-7-en-7-yl]-2-methylhepta-2,6-dienoic acid

CAS Registry Number

Not Available

SMILES

CC(=C)[C@H]1C[C@H]2OC(=O)CC[C@@]11C[C@]11CC[C@]3(C)C(=CC[C@@]3(C)[C@H]21)C(=C)CC\C=C(\C)C(O)=O

InChI Identifier

InChI=1S/C30H40O4/c1-18(2)22-16-23-25-28(6)12-10-21(19(3)8-7-9-20(4)26(32)33)27(28,5)14-15-30(25)17-29(22,30)13-11-24(31)34-23/h9-10,22-23,25H,1,3,7-8,11-17H2,2,4-6H3,(H,32,33)/b20-9-/t22-,23-,25+,27-,28+,29-,30+/m1/s1

InChI Key

OEBCOPKBNAGZEV-PNVFSJBDSA-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
Kadsura angustifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Methyl-branched fatty acid
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Fatty acyl
Fatty acid
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	5.51	ChemAxon
pKa (Strongest Acidic)	4.7	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	134.33 m³·mol⁻¹	ChemAxon
Polarizability	53.71 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

26389056

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53325465

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sun R, Song HC, Wang CR, Shen KZ, Xu YB, Gao YX, Chen YG, Dong JY: Compounds from Kadsura angustifolia with anti-HIV activity. Bioorg Med Chem Lett. 2011 Feb 1;21(3):961-5. doi: 10.1016/j.bmcl.2010.12.055. Epub 2010 Dec 21. [PubMed:21232955 ]
LOTUS database [Link]

Showing NP-Card for angustific acid (NP0320061)

MOL for NP0320061 (angustific acid)

3D MOL for NP0320061 (angustific acid)

3D SDF for NP0320061 (angustific acid)

3D-SDF for NP0320061 (angustific acid)

PDB for NP0320061 (angustific acid)

3D PDB for NP0320061 (angustific acid)

SMILES for NP0320061 (angustific acid)

INCHI for NP0320061 (angustific acid)

Structure for NP0320061 (angustific acid)

3D Structure for NP0320061 (angustific acid)