NP-MRD: Showing NP-Card for (2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde (NP0246125)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 07:28:27 UTC

Updated at

2022-09-07 07:28:27 UTC

NP-MRD ID

NP0246125

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde

Description

(2S,5aalpha,9balpha,alphaR)-alpha-(3-Furyl)-2alpha-formyl-2,3abeta,6,6,9abeta-pentamethyldodecahydro-1H-cyclopenta[a]naphthalene-3beta-ethanol belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. (2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde is found in Hyrtios erectus. Based on a literature review very few articles have been published on (2S,5aalpha,9balpha,alphaR)-alpha-(3-Furyl)-2alpha-formyl-2,3abeta,6,6,9abeta-pentamethyldodecahydro-1H-cyclopenta[a]naphthalene-3beta-ethanol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072209282D          

 28 31  0  0  1  0            999 V2000
    5.5018   -0.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5672   -1.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1312    1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7565   -0.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8307   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9770   -1.3851    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7532   -1.6644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3469   -1.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4075   -2.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -3.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8889   -2.4223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4543   -1.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5883    0.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1699    1.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7408    2.1700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 22  2  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  1  0  0  0
 25 26  2  0  0  0  0
 23 27  1  0  0  0  0
 28 27  1  6  0  0  0
  7 28  1  0  0  0  0
 12 28  1  0  0  0  0
M  END

     RDKit          3D

 66 69  0  0  0  0  0  0  0  0999 V2000
   -4.2500   -1.4890    1.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8066   -1.1371    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0133   -2.4192   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7171   -0.1074   -0.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8977    0.7207   -1.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8839    1.5252   -0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0560    0.6836    0.2732 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4243    1.1054    1.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3894   -0.7640   -0.0228 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4861   -1.7063    0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0863   -1.5042    0.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3344   -0.1143    0.5264 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5930    0.0701    1.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467    0.3312   -0.2942 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7854   -0.3874   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8950    0.0040   -1.0088 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2604    1.3330   -0.9536 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1088   -0.8579   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5023   -1.9784   -1.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6752   -2.4204   -0.9144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9543   -1.6030    0.0624 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0658   -0.6616    0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4838    1.8018   -0.1651 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3077    2.4027    0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8233    2.4745   -1.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426    3.6582   -1.5049 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0067    2.1512    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6366    0.8477   -0.1021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5894   -0.5951    2.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1837   -2.1190    1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5341   -2.1171    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8026   -3.2949   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0335   -2.4766   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2407   -2.4661   -1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5437   -0.5725   -1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1968    0.5586    0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5997    1.4335   -1.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4734    0.1089   -2.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4167    2.3499   -0.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438    2.0350   -1.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4882    1.4881    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265    2.0104    1.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3993    0.3271    2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913   -0.9228   -1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8597   -2.7356    0.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6231   -1.4553    1.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1733   -1.5996   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5862   -2.2831    0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3524    1.0595    2.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548   -0.1229    2.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0298   -0.6518    2.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135    0.0995   -1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4867   -0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1878   -0.3745    0.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6149   -0.1906   -2.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6272    1.6296   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9714   -2.4128   -2.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -3.2883   -1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0169    0.1642    0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9273    3.2137    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583    2.9453    1.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    1.6877    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8047    1.9460   -2.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3396    2.9483   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548    2.5718    1.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5790    0.6292   -1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 27  1  0
 27 28  1  0
 28 12  1  0
 12 13  1  1
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  2  1  0
  2  1  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 22  2  0
 22 21  1  0
 21 20  1  0
 20 19  2  0
 23 25  1  6
 25 26  2  0
 14 23  1  0
 19 18  1  0
  7 28  1  0
  7  9  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  6
 13 49  1  0
 13 50  1  0
 13 51  1  0
 11 47  1  0
 11 48  1  0
 10 45  1  0
 10 46  1  0
  9 44  1  6
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
 14 52  1  6
 15 53  1  0
 15 54  1  0
 16 55  1  6
 17 56  1  0
 22 59  1  0
 20 58  1  0
 19 57  1  0
 25 63  1  0
M  END


  Mrv1652309072209282D          

 28 31  0  0  1  0            999 V2000
    5.5018   -0.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5672   -1.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1312    1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7565   -0.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8307   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9770   -1.3851    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7532   -1.6644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3469   -1.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4075   -2.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -3.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8889   -2.4223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4543   -1.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5883    0.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1699    1.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7408    2.1700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 22  2  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  1  0  0  0
 25 26  2  0  0  0  0
 23 27  1  0  0  0  0
 28 27  1  6  0  0  0
  7 28  1  0  0  0  0
 12 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246125

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(C[C@H]2[C@@](C)(CC[C@H]3C(C)(C)CCC[C@]23C)[C@@H]1C[C@@H](O)C1=COC=C1)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O3/c1-22(2)9-6-10-24(4)19(22)7-11-25(5)20(23(3,16-26)14-21(24)25)13-18(27)17-8-12-28-15-17/h8,12,15-16,18-21,27H,6-7,9-11,13-14H2,1-5H3/t18-,19+,20-,21-,23-,24+,25+/m1/s1

> <INCHI_KEY>
PUTJFIQGLGDLIT-YVWILONDSA-N

> <FORMULA>
C25H38O3

> <MOLECULAR_WEIGHT>
386.576

> <EXACT_MASS>
386.282095084

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
45.69983941688123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,3aR,5aS,9aS,9bR)-3-[(2R)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-dodecahydro-1H-cyclopenta[a]naphthalene-2-carbaldehyde

> <JCHEM_LOGP>
5.248440436666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.013663094957675

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8882835651597647

> <JCHEM_POLAR_SURFACE_AREA>
50.440000000000005

> <JCHEM_REFRACTIVITY>
111.6629

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,3aR,5aS,9aS,9bR)-3-[(2R)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1H-cyclopenta[a]naphthalene-2-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      10.270  -1.159   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.525  -2.095   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.384   2.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.845   2.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.279  -1.660   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.727  -0.076   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.551  -1.070   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.824  -2.586   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.273  -3.107   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.648  -3.580   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.761  -5.116   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.665  -5.698   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.659  -4.522   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.848  -3.213   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.614   1.460   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.098   1.187   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.184   2.939   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.249   4.051   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.039   2.042   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   28                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   28                                             
CONECT   13   12                                                            
CONECT   14   12   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18                                                       
CONECT   23   14   24   25   27                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   23   28                                                       
CONECT   28   27    7   12                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
(2S,5Aalpha,9balpha,alphar)-a-(3-furyl)-2a-formyl-2,3abeta,6,6,9abeta-pentamethyldodecahydro-1H-cyclopenta[a]naphthalene-3b-ethanol	Generator
(2S,5Aalpha,9balpha,alphar)-α-(3-furyl)-2α-formyl-2,3abeta,6,6,9abeta-pentamethyldodecahydro-1H-cyclopenta[a]naphthalene-3β-ethanol	Generator

Chemical Formula

C₂₅H₃₈O₃

Average Mass

386.5760 Da

Monoisotopic Mass

386.28210 Da

IUPAC Name

(2S,3S,3aR,5aS,9aS,9bR)-3-[(2R)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-dodecahydro-1H-cyclopenta[a]naphthalene-2-carbaldehyde

Traditional Name

(2S,3S,3aR,5aS,9aS,9bR)-3-[(2R)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1H-cyclopenta[a]naphthalene-2-carbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@@]1(C[C@H]2[C@@](C)(CC[C@H]3C(C)(C)CCC[C@]23C)[C@@H]1C[C@@H](O)C1=COC=C1)C=O

InChI Identifier

InChI=1S/C25H38O3/c1-22(2)9-6-10-24(4)19(22)7-11-25(5)20(23(3,16-26)14-21(24)25)13-18(27)17-8-12-28-15-17/h8,12,15-16,18-21,27H,6-7,9-11,13-14H2,1-5H3/t18-,19+,20-,21-,23-,24+,25+/m1/s1

InChI Key

PUTJFIQGLGDLIT-YVWILONDSA-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
Hyrtios erectus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Aromatic monoterpenoid
11-noriridane monoterpenoid
Furan
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Aromatic alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aldehyde
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	5.25	ChemAxon
pKa (Strongest Acidic)	14.01	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111.66 m³·mol⁻¹	ChemAxon
Polarizability	45.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9501593

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11326641

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde (NP0246125)

MOL for NP0246125 ((2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde)

3D MOL for NP0246125 ((2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde)

3D SDF for NP0246125 ((2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde)

3D-SDF for NP0246125 ((2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde)

PDB for NP0246125 ((2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde)

3D PDB for NP0246125 ((2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde)

SMILES for NP0246125 ((2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde)

INCHI for NP0246125 ((2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde)

Structure for NP0246125 ((2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde)

3D Structure for NP0246125 ((2s,3s,3ar,5as,9as,9br)-3-[(2r)-2-(furan-3-yl)-2-hydroxyethyl]-2,3a,6,6,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalene-2-carbaldehyde)