Natural Product: NPC470973

Natural Product ID:  NPC470973
Common Name:   Songaricalarin C
IUPAC Name:   [(1E,3S,3aS,4S,5R,6R,7S,7aR)-4-(chloromethyl)-1-ethylidene-4-hydroxy-3,6-bis(2-methylbutanoyloxy)-7-[(2S)-2-methyloxiran-2-yl]-2-oxo-3,3a,5,6,7,7a-hexahydroinden-5-yl] (E)-3-methylpent-2-enoate
Synonyms:   Songaricalarin C
Molecular Formula:   C31H45ClO9
Standard InCHIKey:  IUPCAKPGHKSLTM-IDZHRBHZSA-N
Standard InCHI:  InChI=1S/C31H45ClO9/c1-9-16(5)13-20(33)39-27-26(41-29(36)18(7)11-3)22(30(8)15-38-30)21-19(12-4)24(34)25(23(21)31(27,37)14-32)40-28(35)17(6)10-2/h12-13,17-18,21-23,25-27,37H,9-11,14-15H2,1-8H3/b16-13+,19-12+/t17?,18?,21-,22-,23-,25-,26+,27+,30+,31-/m0/s1
Canonical SMILES:  CC/C(=C/C(=O)O[C@@H]1[C@H](OC(=O)C(CC)C)[C@H]([C@H]2[C@H]([C@@]1(O)CCl)[C@H](OC(=O)C(CC)C)C(=O)/C/2=C/C)[C@]1(C)OC1)/C
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO5813 Ligularia songarica Species Asteraceae Eukaryota PMID[23043462]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens EC50 = 12.1 ug/ml 19943620
NPT81 Cell Line A549 Homo sapiens EC50 = 10.6 ug/ml 19943620
NPT2 Others Unspecified EC50 = 3.7 ug/ml 19928832
NPT91 Cell Line KB Homo sapiens EC50 = 4.7 ug/ml 19928832

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC470973 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.8696 High Similarity NPC471934
0.8361 Intermediate Similarity NPC472667
0.8359 Intermediate Similarity NPC470185
0.8319 Intermediate Similarity NPC471933
0.824 Intermediate Similarity NPC473802
0.8226 Intermediate Similarity NPC310511
0.8175 Intermediate Similarity NPC473709
0.8175 Intermediate Similarity NPC473919
0.8145 Intermediate Similarity NPC143755
0.811 Intermediate Similarity NPC471939
0.8051 Intermediate Similarity NPC474716
0.8047 Intermediate Similarity NPC471940
0.8016 Intermediate Similarity NPC310035
0.8016 Intermediate Similarity NPC282003
0.8016 Intermediate Similarity NPC188222
0.8016 Intermediate Similarity NPC257017
0.8016 Intermediate Similarity NPC162009
0.8 Intermediate Similarity NPC145182
0.8 Intermediate Similarity NPC471126
0.8 Intermediate Similarity NPC157252
0.8 Intermediate Similarity NPC471128
0.797 Intermediate Similarity NPC130447
0.7969 Intermediate Similarity NPC473635
0.7967 Intermediate Similarity NPC255450
0.7967 Intermediate Similarity NPC170692
0.7966 Intermediate Similarity NPC470975
0.7966 Intermediate Similarity NPC470980
0.7966 Intermediate Similarity NPC470979
0.7966 Intermediate Similarity NPC103088
0.7953 Intermediate Similarity NPC472399
0.7953 Intermediate Similarity NPC303006
0.7951 Intermediate Similarity NPC477126
0.7937 Intermediate Similarity NPC52839
0.7891 Intermediate Similarity NPC172154
0.7891 Intermediate Similarity NPC81736
0.7886 Intermediate Similarity NPC178289
0.7874 Intermediate Similarity NPC222688
0.7874 Intermediate Similarity NPC170538
0.7869 Intermediate Similarity NPC95290
0.7869 Intermediate Similarity NPC189338
0.7868 Intermediate Similarity NPC473396
0.7863 Intermediate Similarity NPC470972
0.7863 Intermediate Similarity NPC473838
0.7863 Intermediate Similarity NPC475389
0.7857 Intermediate Similarity NPC4548
0.7857 Intermediate Similarity NPC472004
0.784 Intermediate Similarity NPC311554
0.784 Intermediate Similarity NPC472397
0.784 Intermediate Similarity NPC171905
0.784 Intermediate Similarity NPC471125
0.784 Intermediate Similarity NPC472758
0.784 Intermediate Similarity NPC257457
0.7829 Intermediate Similarity NPC293112
0.7823 Intermediate Similarity NPC470793
0.7812 Intermediate Similarity NPC11895
0.7812 Intermediate Similarity NPC120724
0.7805 Intermediate Similarity NPC89018
0.7803 Intermediate Similarity NPC475139
0.7803 Intermediate Similarity NPC180902
0.7803 Intermediate Similarity NPC471855
0.7795 Intermediate Similarity NPC472401
0.7786 Intermediate Similarity NPC231529
0.7778 Intermediate Similarity NPC5292
0.7778 Intermediate Similarity NPC5989
0.7778 Intermediate Similarity NPC471108
0.7778 Intermediate Similarity NPC255081
0.7778 Intermediate Similarity NPC275696
0.7778 Intermediate Similarity NPC5991
0.7778 Intermediate Similarity NPC22628
0.7778 Intermediate Similarity NPC475041
0.776 Intermediate Similarity NPC156252
0.776 Intermediate Similarity NPC476713
0.776 Intermediate Similarity NPC473590
0.776 Intermediate Similarity NPC476712
0.7752 Intermediate Similarity NPC145238
0.7752 Intermediate Similarity NPC24651
0.7752 Intermediate Similarity NPC469790
0.775 Intermediate Similarity NPC469558
0.7742 Intermediate Similarity NPC88867
0.7742 Intermediate Similarity NPC121816
0.7742 Intermediate Similarity NPC226608
0.7734 Intermediate Similarity NPC269642
0.7734 Intermediate Similarity NPC19464
0.7724 Intermediate Similarity NPC258711
0.7724 Intermediate Similarity NPC35069
0.7724 Intermediate Similarity NPC317687
0.7724 Intermediate Similarity NPC473877
0.7724 Intermediate Similarity NPC475391
0.7721 Intermediate Similarity NPC473233
0.7717 Intermediate Similarity NPC107338
0.7717 Intermediate Similarity NPC109607
0.7717 Intermediate Similarity NPC251226
0.771 Intermediate Similarity NPC476091
0.771 Intermediate Similarity NPC236999
0.771 Intermediate Similarity NPC270109
0.771 Intermediate Similarity NPC476078
0.7705 Intermediate Similarity NPC253906
0.7704 Intermediate Similarity NPC245017
0.7698 Intermediate Similarity NPC124676
0.7698 Intermediate Similarity NPC153440
0.7698 Intermediate Similarity NPC475401
0.7698 Intermediate Similarity NPC146280
0.7698 Intermediate Similarity NPC476714
0.7692 Intermediate Similarity NPC217901
0.7687 Intermediate Similarity NPC475500
0.7687 Intermediate Similarity NPC100017
0.7687 Intermediate Similarity NPC182266
0.7687 Intermediate Similarity NPC223356
0.7687 Intermediate Similarity NPC471136
0.7687 Intermediate Similarity NPC471137
0.7687 Intermediate Similarity NPC473548
0.7687 Intermediate Similarity NPC296617
0.7687 Intermediate Similarity NPC471234
0.7687 Intermediate Similarity NPC475154
0.768 Intermediate Similarity NPC96312
0.768 Intermediate Similarity NPC476711
0.768 Intermediate Similarity NPC328374
0.768 Intermediate Similarity NPC470466
0.768 Intermediate Similarity NPC234858
0.768 Intermediate Similarity NPC190286
0.768 Intermediate Similarity NPC476710
0.768 Intermediate Similarity NPC40632
0.768 Intermediate Similarity NPC154363
0.768 Intermediate Similarity NPC270478
0.768 Intermediate Similarity NPC251236
0.768 Intermediate Similarity NPC471127
0.7674 Intermediate Similarity NPC469789
0.7674 Intermediate Similarity NPC105926
0.7674 Intermediate Similarity NPC91693
0.7674 Intermediate Similarity NPC265557
0.7674 Intermediate Similarity NPC18945
0.7674 Intermediate Similarity NPC67251
0.7674 Intermediate Similarity NPC473979
0.7661 Intermediate Similarity NPC962
0.7661 Intermediate Similarity NPC250109
0.7661 Intermediate Similarity NPC471204
0.7661 Intermediate Similarity NPC474937
0.7661 Intermediate Similarity NPC273242
0.7661 Intermediate Similarity NPC317210
0.7656 Intermediate Similarity NPC470779
0.7656 Intermediate Similarity NPC159456
0.7656 Intermediate Similarity NPC4021
0.7652 Intermediate Similarity NPC475371
0.7652 Intermediate Similarity NPC104382
0.7652 Intermediate Similarity NPC162495
0.7652 Intermediate Similarity NPC175186
0.7652 Intermediate Similarity NPC471407
0.7652 Intermediate Similarity NPC470974
0.7652 Intermediate Similarity NPC470978
0.7652 Intermediate Similarity NPC470851
0.7652 Intermediate Similarity NPC470880
0.7642 Intermediate Similarity NPC174471
0.7642 Intermediate Similarity NPC474871
0.7642 Intermediate Similarity NPC474846
0.7642 Intermediate Similarity NPC469655
0.7642 Intermediate Similarity NPC96739
0.7642 Intermediate Similarity NPC469656
0.7642 Intermediate Similarity NPC260786
0.7642 Intermediate Similarity NPC317107
0.7638 Intermediate Similarity NPC477092
0.7638 Intermediate Similarity NPC470186
0.7638 Intermediate Similarity NPC475775
0.7638 Intermediate Similarity NPC19028
0.7638 Intermediate Similarity NPC476529
0.7638 Intermediate Similarity NPC9674
0.7634 Intermediate Similarity NPC470882
0.7634 Intermediate Similarity NPC168849
0.7634 Intermediate Similarity NPC473253
0.7634 Intermediate Similarity NPC287423
0.7634 Intermediate Similarity NPC475273
0.7623 Intermediate Similarity NPC273433
0.7619 Intermediate Similarity NPC471854
0.7619 Intermediate Similarity NPC10721
0.7619 Intermediate Similarity NPC475305
0.7619 Intermediate Similarity NPC296822
0.7615 Intermediate Similarity NPC476729
0.7615 Intermediate Similarity NPC470922
0.7612 Intermediate Similarity NPC58029
0.7607 Intermediate Similarity NPC152480
0.7603 Intermediate Similarity NPC319438
0.7603 Intermediate Similarity NPC216636
0.76 Intermediate Similarity NPC472400
0.76 Intermediate Similarity NPC473798
0.76 Intermediate Similarity NPC474872
0.7597 Intermediate Similarity NPC23786
0.7597 Intermediate Similarity NPC470265
0.7597 Intermediate Similarity NPC312833
0.7594 Intermediate Similarity NPC475314
0.7594 Intermediate Similarity NPC251564
0.7594 Intermediate Similarity NPC475606
0.7594 Intermediate Similarity NPC477189
0.7594 Intermediate Similarity NPC471170
0.7583 Intermediate Similarity NPC477127
0.7581 Intermediate Similarity NPC89227
0.7581 Intermediate Similarity NPC215643
0.7581 Intermediate Similarity NPC170212
0.7581 Intermediate Similarity NPC265499
0.7581 Intermediate Similarity NPC17138
0.7581 Intermediate Similarity NPC221511
0.7581 Intermediate Similarity NPC101825

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC470973 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.7795 Intermediate Similarity NPD5983 Phase 2
0.7692 Intermediate Similarity NPD6336 Discontinued
0.7661 Intermediate Similarity NPD4632 Approved
0.7638 Intermediate Similarity NPD7100 Approved
0.7559 Intermediate Similarity NPD6335 Approved
0.75 Intermediate Similarity NPD7101 Approved
0.748 Intermediate Similarity NPD6009 Approved
0.7442 Intermediate Similarity NPD6319 Approved
0.744 Intermediate Similarity NPD8297 Approved
0.7422 Intermediate Similarity NPD6313 Approved
0.7422 Intermediate Similarity NPD6314 Approved
0.736 Intermediate Similarity NPD6649 Approved
0.736 Intermediate Similarity NPD6650 Approved
0.7339 Intermediate Similarity NPD6373 Approved
0.7339 Intermediate Similarity NPD6372 Approved
0.7317 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD6033 Approved
0.7258 Intermediate Similarity NPD6881 Approved
0.7258 Intermediate Similarity NPD6899 Approved
0.7236 Intermediate Similarity NPD5739 Approved
0.7236 Intermediate Similarity NPD6402 Approved
0.7236 Intermediate Similarity NPD6675 Approved
0.7236 Intermediate Similarity NPD7128 Approved
0.7209 Intermediate Similarity NPD7115 Discovery
0.719 Intermediate Similarity NPD5344 Discontinued
0.7177 Intermediate Similarity NPD5697 Approved
0.7165 Intermediate Similarity NPD6882 Approved
0.7164 Intermediate Similarity NPD7507 Approved
0.7143 Intermediate Similarity NPD7604 Phase 2
0.7143 Intermediate Similarity NPD7102 Approved
0.7143 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7290 Approved
0.7143 Intermediate Similarity NPD6883 Approved
0.7132 Intermediate Similarity NPD7319 Approved
0.712 Intermediate Similarity NPD7320 Approved
0.7097 Intermediate Similarity NPD6008 Approved
0.709 Intermediate Similarity NPD7492 Approved
0.7087 Intermediate Similarity NPD8130 Phase 1
0.7087 Intermediate Similarity NPD5215 Approved
0.7087 Intermediate Similarity NPD6617 Approved
0.7087 Intermediate Similarity NPD6847 Approved
0.7087 Intermediate Similarity NPD6869 Approved
0.7063 Intermediate Similarity NPD6012 Approved
0.7063 Intermediate Similarity NPD6014 Approved
0.7063 Intermediate Similarity NPD6013 Approved
0.7063 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD6054 Approved
0.704 Intermediate Similarity NPD5701 Approved
0.7037 Intermediate Similarity NPD6616 Approved
0.7009 Intermediate Similarity NPD46 Approved
0.7009 Intermediate Similarity NPD6698 Approved
0.7008 Intermediate Similarity NPD5169 Approved
0.7 Intermediate Similarity NPD6868 Approved
0.6985 Remote Similarity NPD7078 Approved
0.6984 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6984 Remote Similarity NPD6011 Approved
0.6967 Remote Similarity NPD6648 Approved
0.6953 Remote Similarity NPD5216 Approved
0.6953 Remote Similarity NPD5127 Approved
0.6953 Remote Similarity NPD5217 Approved
0.694 Remote Similarity NPD6370 Approved
0.6934 Remote Similarity NPD7736 Approved
0.6923 Remote Similarity NPD5167 Approved
0.6917 Remote Similarity NPD6059 Approved
0.6905 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6053 Discontinued
0.6885 Remote Similarity NPD7638 Approved
0.6875 Remote Similarity NPD6371 Approved
0.6866 Remote Similarity NPD6016 Approved
0.6866 Remote Similarity NPD6015 Approved
0.6861 Remote Similarity NPD8293 Discontinued
0.686 Remote Similarity NPD4792 Clinical (unspecified phase)
0.685 Remote Similarity NPD5128 Approved
0.6842 Remote Similarity NPD7516 Approved
0.6829 Remote Similarity NPD7640 Approved
0.6829 Remote Similarity NPD7639 Approved
0.6822 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6815 Remote Similarity NPD5988 Approved
0.6767 Remote Similarity NPD7328 Approved
0.6767 Remote Similarity NPD7327 Approved
0.6744 Remote Similarity NPD4634 Approved
0.6742 Remote Similarity NPD6274 Approved
0.672 Remote Similarity NPD5211 Phase 2
0.6719 Remote Similarity NPD6686 Approved
0.6714 Remote Similarity NPD5956 Approved
0.6694 Remote Similarity NPD5285 Approved
0.6694 Remote Similarity NPD5286 Approved
0.6694 Remote Similarity NPD4696 Approved
0.6667 Remote Similarity NPD6083 Phase 2
0.6667 Remote Similarity NPD4755 Approved
0.6667 Remote Similarity NPD7260 Phase 2
0.6667 Remote Similarity NPD6084 Phase 2
0.6642 Remote Similarity NPD8328 Phase 3
0.6641 Remote Similarity NPD6614 Approved
0.6639 Remote Similarity NPD5695 Phase 3
0.6618 Remote Similarity NPD8033 Approved
0.6618 Remote Similarity NPD8380 Approved
0.6618 Remote Similarity NPD8378 Approved
0.6618 Remote Similarity NPD8296 Approved
0.6618 Remote Similarity NPD8335 Approved
0.6618 Remote Similarity NPD8379 Approved
0.6614 Remote Similarity NPD5141 Approved
0.6613 Remote Similarity NPD4225 Approved
0.6613 Remote Similarity NPD5696 Approved
0.6593 Remote Similarity NPD4522 Approved
0.6587 Remote Similarity NPD5224 Approved
0.6587 Remote Similarity NPD5226 Approved
0.6587 Remote Similarity NPD4633 Approved
0.6587 Remote Similarity NPD5225 Approved
0.6583 Remote Similarity NPD7838 Discovery
0.6567 Remote Similarity NPD6317 Approved
0.656 Remote Similarity NPD4700 Approved
0.6544 Remote Similarity NPD8294 Approved
0.6544 Remote Similarity NPD8377 Approved
0.6535 Remote Similarity NPD5174 Approved
0.6535 Remote Similarity NPD5175 Approved
0.6512 Remote Similarity NPD6412 Phase 2
0.6508 Remote Similarity NPD1700 Approved
0.6508 Remote Similarity NPD5223 Approved
0.6496 Remote Similarity NPD7503 Approved
0.6496 Remote Similarity NPD6909 Approved
0.6496 Remote Similarity NPD6908 Approved
0.6496 Remote Similarity NPD6921 Approved
0.6462 Remote Similarity NPD4729 Approved
0.6462 Remote Similarity NPD4730 Approved
0.6462 Remote Similarity NPD5168 Approved
0.6441 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6434 Remote Similarity NPD4767 Approved
0.6434 Remote Similarity NPD4768 Approved
0.64 Remote Similarity NPD5959 Approved
0.6393 Remote Similarity NPD5693 Phase 1
0.6389 Remote Similarity NPD6845 Suspended
0.6377 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6377 Remote Similarity NPD8513 Phase 3
0.6377 Remote Similarity NPD8517 Approved
0.6377 Remote Similarity NPD8516 Approved
0.6377 Remote Similarity NPD8515 Approved
0.6371 Remote Similarity NPD5654 Approved
0.6364 Remote Similarity NPD5249 Phase 3
0.6364 Remote Similarity NPD1695 Approved
0.6364 Remote Similarity NPD5251 Approved
0.6364 Remote Similarity NPD5248 Approved
0.6364 Remote Similarity NPD5250 Approved
0.6364 Remote Similarity NPD5247 Approved
0.6341 Remote Similarity NPD6399 Phase 3
0.6328 Remote Similarity NPD5091 Approved
0.6328 Remote Similarity NPD7632 Discontinued
0.6328 Remote Similarity NPD3653 Clinical (unspecified phase)
0.6324 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6316 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6311 Remote Similarity NPD5785 Approved
0.6279 Remote Similarity NPD4754 Approved
0.626 Remote Similarity NPD7983 Approved
0.624 Remote Similarity NPD6356 Clinical (unspecified phase)
0.623 Remote Similarity NPD6673 Approved
0.623 Remote Similarity NPD6904 Approved
0.623 Remote Similarity NPD6080 Approved
0.6222 Remote Similarity NPD8133 Approved
0.619 Remote Similarity NPD5220 Clinical (unspecified phase)
0.619 Remote Similarity NPD4697 Phase 3
0.619 Remote Similarity NPD5221 Approved
0.619 Remote Similarity NPD5222 Approved
0.6186 Remote Similarity NPD6435 Approved
0.6167 Remote Similarity NPD5363 Approved
0.6165 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6154 Remote Similarity NPD8074 Phase 3
0.6148 Remote Similarity NPD5737 Approved
0.6148 Remote Similarity NPD6672 Approved
0.6142 Remote Similarity NPD7902 Approved
0.6142 Remote Similarity NPD5173 Approved
0.6129 Remote Similarity NPD6079 Approved
0.6129 Remote Similarity NPD6050 Approved
0.6119 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6119 Remote Similarity NPD5135 Approved
0.6116 Remote Similarity NPD6409 Approved
0.6116 Remote Similarity NPD7521 Approved
0.6116 Remote Similarity NPD7146 Approved
0.6116 Remote Similarity NPD7334 Approved
0.6116 Remote Similarity NPD5330 Approved
0.6116 Remote Similarity NPD5786 Approved
0.6116 Remote Similarity NPD6684 Approved
0.6111 Remote Similarity NPD5210 Approved
0.6111 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6111 Remote Similarity NPD4629 Approved
0.6107 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6098 Remote Similarity NPD5328 Approved
0.6098 Remote Similarity NPD4753 Phase 2
0.6094 Remote Similarity NPD8029 Clinical (unspecified phase)
0.609 Remote Similarity NPD7236 Approved
0.608 Remote Similarity NPD4202 Approved
0.608 Remote Similarity NPD5778 Approved
0.608 Remote Similarity NPD5133 Approved
0.608 Remote Similarity NPD5779 Approved
0.6056 Remote Similarity NPD7642 Approved
0.6053 Remote Similarity NPD8384 Approved
0.6048 Remote Similarity NPD5692 Phase 3
0.6033 Remote Similarity NPD1694 Approved
0.6032 Remote Similarity NPD5282 Discontinued
0.6032 Remote Similarity NPD7748 Approved
0.6017 Remote Similarity NPD5368 Approved

Structure

External Identifiers

PubChem CID   71658514
ChEMBL   CHEMBL2334363
ZINC  

Physicochemical Properties

Molecular Weight:  596.28
ALogP:  0.427
MLogP:  3.77
XLogP:  4.578
# Rotatable Bonds:  24
Polar Surface Area:  128.73
# H-Bond Aceptor:  9
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  41

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs