NP-MRD: Showing NP-Card for (1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0257431)

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Record Information

Version

2.0

Created at

2022-09-07 22:33:15 UTC

Updated at

2022-09-07 22:33:15 UTC

NP-MRD ID

NP0257431

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

Description

(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2S,5S)-5-Ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. (1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol is found in Acca sellowiana, Ajuga taiwanensis, Allanblackia floribunda, Annona purpurea, Aphanamixis polystachya, Aristolochia kaempferi, Aristolochia manshuriensis, Artabotrys hexapetalus, Artemisia sieversiana, Artemisia vulgaris, Aureoumbra lagunensis, Barringtonia racemosa, Bauhinia forficata, Begonia nantoensis, Brosimum acutifolium, Butea monosperma, Caesalpinia minax, Campylospermum sulcatum, Celtis laevigata, Centrosema pubescens, Chamaecyparis formosensis, Cichorium intybus, Cinnamomum subavenium, Cinnamosma madagascariensis, Couepia polyandra, Cussonia bancoensis, Dioscorea communis, Diospyros buxifolia, Drypetes inaequalis, Duhaldea cappa, Dynamena pumila, Eleutherococcus senticosus, Embelia schimperi, Erythrina variegata, Euphorbia indica, Euphorbia sessiliflora, Eysenhardtia polystachya, Ferula diversivittata, Ficus hirta, Frullania brasiliensis, Frullania monocera, Garcinia multiflora, Gentiana lutea, Gleditsia sinensis, Gloriosa superba, Gonospermum gomerae, Heliotropium indicum, Heracleum wallichii, Herpetospermum pedunculosum, Hertia cheirifolia, Hibiscus taiwanensis, Hypericum beanii, Inula anatolica, Iris sofarana, Justicia heterocarpa, Launaea arborescens, Laurencia obtusa, Leucas aspera, Luzula pilosa, Lygodium flexuosum, Melicope latifolia, Melicope semecarpifolia, Monascus pilosus, Nicotiana benthamiana, Ongokea gore, Pachysandra terminalis, Paederia foetida, Phaseolus vulgaris, Piper kadsura, Piper methysticum, Piper nigrum, Planchonia careya, Pluchea indica, Prosopis spicigera, Prunus laurocerasus, Pseudelephantopus spicatus, Pterocarpus santalinus, Pulicaria canariensis, Pycnandra acuminata, Robinsonecio gerberifolius, Rohdea chinensis, Rubia wallichiana, Rubia yunnanensis, Salvia aegyptiaca, Salvia officinalis, Sambucus chinensis, Saussurea muliensis, Schistochila glaucescens, Schleichera oleosa, Scleropyrum pentandrum, Sideritis discolor, Spiraea formosana, Stemodia foliosa, Strychnos potatorum, Taiwanofungus camphoratus, Taraxacum mongolicum, Terminalia hylodendron, Terminalia superba, Ternstroemia gymnanthera, Theobroma cacao, Tovomita brasiliensis, Trichosanthes kirilowii, Trigonostemon reidioides, Tritomaria quinquedentata, Ulmus minor, Ventilago leiocarpa, Vernicia fordii, Virola surinamensis, Viscum coloratum, Vismia laurentii, Withania somnifera, Xanthium strumarium, Xylopia aromatica and Zea mays. Based on a literature review very few articles have been published on (3S,8S,9S,10R,13R,14S,17R)-17-[(E,2S,5S)-5-Ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082200332D          

 30 33  0  0  1  0            999 V2000
   -0.5116   -1.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -1.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.1509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7071   -2.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  1  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 78 81  0  0  0  0  0  0  0  0999 V2000
    4.4588   -2.8693   -1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9270   -1.6465   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8194   -1.0275    0.3505 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1521    0.1873    0.9794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9933    0.6299    0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2637    1.8006    1.1351 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1951    2.3548    2.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9363    1.4818    1.7050 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2949    2.7380    2.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9762    2.9040    1.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3839    1.4722    1.2942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5108    1.1422    0.4606 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8549    1.6431    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8688    1.3356    0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7886    0.2862   -0.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8622    0.0861   -1.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4345   -1.2911   -1.5235 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2452   -2.0897   -2.6440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8362   -1.9329   -0.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3288   -2.0416   -0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6845   -0.7062   -0.7008 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9925   -0.8698   -2.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899   -0.3504    0.4065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4401   -1.1433    0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2609   -0.5989    1.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0911    0.8891    0.7726 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1598    1.0906   -0.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1214   -0.4901   -0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0216   -1.4661   -0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9160    0.6978   -1.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5518   -3.3586   -1.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1501   -2.7105   -2.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8271   -3.6488   -0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9838   -1.9287   -0.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6401   -0.9421   -1.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0349   -1.7519    1.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6677    0.7049    1.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    0.0885   -0.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1871    2.6095    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1831    2.6254    1.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3824    1.6085    3.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8130    3.3164    2.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290    0.7869    2.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9412    3.6351    2.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0090    2.6570    3.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093    3.3957    0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7144    3.4306    2.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5846    1.1229    2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5622    1.6311   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9950    0.9833    1.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7853    2.7019    1.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7123    2.0005   -0.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6823    0.8288   -1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5279    0.1642   -2.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5394   -1.2265   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8782   -2.8625   -2.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1529   -1.3124    0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2197   -2.9647   -0.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1204   -2.8134   -1.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9864   -2.3805    0.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7842   -0.8728   -2.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3185   -0.0432   -2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223   -1.8791   -2.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1841   -0.6461    1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6287   -2.1664    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1213   -1.3065   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6402   -1.1452    0.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3983   -0.7370    2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7736    1.4199   -1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3265    0.0786   -1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0006    1.7747   -0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6487   -0.0695    0.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086   -2.5141   -0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0878   -1.2094   -0.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0281   -1.2779   -1.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2320    1.4033   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8421    1.2579   -1.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3687    0.4395   -2.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
  3 28  1  0
 28 29  1  0
 28 30  1  0
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  1
  4 37  1  0
  5 38  1  0
  6 39  1  6
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  1
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  1
 12 49  1  6
 13 50  1  0
 13 51  1  0
 14 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  1
 18 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 22 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  1
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 24 66  1  0
 25 67  1  0
 25 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 30 78  1  0
M  END


  Mrv1652309082200332D          

 30 33  0  0  1  0            999 V2000
   -0.5116   -1.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -1.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.1509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7071   -2.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  1  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257431

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](\C=C\[C@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21+,23-,24-,25+,26-,27-,28-,29+/m0/s1

> <INCHI_KEY>
HCXVJBMSMIARIN-BGDBIVFESA-N

> <FORMULA>
C29H48O

> <MOLECULAR_WEIGHT>
412.702

> <EXACT_MASS>
412.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
52.420869687995065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2S,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <JCHEM_LOGP>
7.482555135333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972437702926293

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
130.88269999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2S,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.955  -2.378   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.571  -2.589   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.320  -5.020   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   26                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   12   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   11    8   27                                             
CONECT   27   26                                                            
CONECT   28    3   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₈O

Average Mass

412.7020 Da

Monoisotopic Mass

412.37052 Da

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2S,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2S,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

CAS Registry Number

Not Available

SMILES

CC[C@H](\C=C\[C@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

InChI Identifier

InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21+,23-,24-,25+,26-,27-,28-,29+/m0/s1

InChI Key

HCXVJBMSMIARIN-BGDBIVFESA-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
Acca sellowiana	LOTUS Database	35616633
Ajuga taiwanensis	LOTUS Database	35616633
Allanblackia floribunda	LOTUS Database	35616633
Annona purpurea	LOTUS Database	35616633
Aphanamixis polystachya	LOTUS Database	35616633
Aristolochia kaempferi	LOTUS Database	35616633
Aristolochia manshuriensis	LOTUS Database	35616633
Artabotrys hexapetalus	LOTUS Database	35616633
Artemisia sieversiana	LOTUS Database	35616633
Artemisia vulgaris	LOTUS Database	35616633
Aureoumbra lagunensis	LOTUS Database	35616633
Barringtonia racemosa	LOTUS Database	35616633
Bauhinia forficata	LOTUS Database	35616633
Begonia nantoensis	LOTUS Database	35616633
Brosimum acutifolium	LOTUS Database	35616633
Butea monosperma	LOTUS Database	35616633
Caesalpinia minax	LOTUS Database	35616633
Campylospermum sulcatum	LOTUS Database	35616633
Celtis laevigata	LOTUS Database	35616633
Centrosema pubescens	LOTUS Database	35616633
Chamaecyparis formosensis	LOTUS Database	35616633
Cichorium intybus	LOTUS Database	35616633
Cinnamomum subavenium	LOTUS Database	35616633
Cinnamosma madagascariensis	LOTUS Database	35616633
Couepia polyandra	LOTUS Database	35616633
Cussonia bancoensis	LOTUS Database	35616633
Dioscorea communis	LOTUS Database	35616633
Diospyros buxifolia	LOTUS Database	35616633
Drypetes inaequalis	LOTUS Database	35616633
Duhaldea cappa	LOTUS Database	35616633
Dynamena pumila	LOTUS Database	35616633
Eleutherococcus senticosus	LOTUS Database	35616633
Embelia schimperi	LOTUS Database	35616633
Erythrina variegata	LOTUS Database	35616633
Euphorbia indica	LOTUS Database	35616633
Euphorbia sessiliflora	LOTUS Database	35616633
Eysenhardtia polystachya	LOTUS Database	35616633
Ferula diversivittata	LOTUS Database	35616633
Ficus hirta	LOTUS Database	35616633
Frullania brasiliensis	LOTUS Database	35616633
Frullania monocera	LOTUS Database	35616633
Garcinia multiflora	LOTUS Database	35616633
Gentiana lutea	LOTUS Database	35616633
Gleditsia sinensis	LOTUS Database	35616633
Gloriosa superba	LOTUS Database	35616633
Gonospermum gomerae	LOTUS Database	35616633
Heliotropium indicum	LOTUS Database	35616633
Heracleum wallichii	LOTUS Database	35616633
Herpetospermum pedunculosum	LOTUS Database	35616633
Hertia cheirifolia	LOTUS Database	35616633
Hibiscus taiwanensis	LOTUS Database	35616633
Hypericum beanii	LOTUS Database	35616633
Inula anatolica	LOTUS Database	35616633
Iris sofarana	LOTUS Database	35616633
Justicia heterocarpa	LOTUS Database	35616633
Launaea arborescens	LOTUS Database	35616633
Laurencia obtusa	LOTUS Database	35616633
Leucas aspera	LOTUS Database	35616633
Luzula pilosa	LOTUS Database	35616633
Lygodium flexuosum	LOTUS Database	35616633
Melicope latifolia	LOTUS Database	35616633
Melicope semecarpifolia	LOTUS Database	35616633
Monascus pilosus	LOTUS Database	35616633
Nicotiana benthamiana	LOTUS Database	35616633
Ongokea gore	LOTUS Database	35616633
Pachysandra terminalis	LOTUS Database	35616633
Paederia foetida	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633
Piper kadsura	LOTUS Database	35616633
Piper methysticum	LOTUS Database	35616633
Piper nigrum	LOTUS Database	35616633
Planchonia careya	LOTUS Database	35616633
Pluchea indica	LOTUS Database	35616633
Prosopis spicigera	LOTUS Database	35616633
Prunus laurocerasus	LOTUS Database	35616633
Pseudelephantopus spicatus	LOTUS Database	35616633
Pterocarpus santalinus	LOTUS Database	35616633
Pulicaria canariensis	LOTUS Database	35616633
Pycnandra acuminata	LOTUS Database	35616633
Robinsonecio gerberifolius	LOTUS Database	35616633
Rohdea chinensis	LOTUS Database	35616633
Rubia wallichiana	LOTUS Database	35616633
Rubia yunnanensis	LOTUS Database	35616633
Salvia aegyptiaca	LOTUS Database	35616633
Salvia officinalis	LOTUS Database	35616633
Sambucus chinensis	LOTUS Database	35616633
Saussurea muliensis	LOTUS Database	35616633
Schistochila glaucescens	LOTUS Database	35616633
Schleichera oleosa	LOTUS Database	35616633
Scleropyrum pentandrum	LOTUS Database	35616633
Sideritis discolor	LOTUS Database	35616633
Spiraea formosana	LOTUS Database	35616633
Stemodia foliosa	LOTUS Database	35616633
Strychnos potatorum	LOTUS Database	35616633
Taiwanofungus camphoratus	LOTUS Database	35616633
Taraxacum mongolicum	LOTUS Database	35616633
Terminalia hylodendron	LOTUS Database	35616633
Terminalia superba	LOTUS Database	35616633
Ternstroemia gymnanthera	LOTUS Database	35616633
Theobroma cacao	LOTUS Database	35616633
Tovomita brasiliensis	LOTUS Database	35616633
Trichosanthes kirilowii	LOTUS Database	35616633
Trigonostemon reidioides	LOTUS Database	35616633
Trilophozia quinquedentata	LOTUS Database	35616633
Ulmus minor	LOTUS Database	35616633
Ventilago leiocarpa	LOTUS Database	35616633
Vernicia fordii	LOTUS Database	35616633
Virola surinamensis	LOTUS Database	35616633
Viscum coloratum	LOTUS Database	35616633
Vismia laurentii	LOTUS Database	35616633
Withania somnifera	LOTUS Database	35616633
Xanthium strumarium	LOTUS Database	35616633
Xylopia aromatica	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Stigmastane-skeleton
Triterpenoid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
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	7.48	ChemAxon
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	130.88 m³·mol⁻¹	ChemAxon
Polarizability	52.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

24589995

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12314479

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0257431)

MOL for NP0257431 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D MOL for NP0257431 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D SDF for NP0257431 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D-SDF for NP0257431 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

PDB for NP0257431 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D PDB for NP0257431 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

SMILES for NP0257431 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

INCHI for NP0257431 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

Structure for NP0257431 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D Structure for NP0257431 ((1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2s,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)