Natural Product: NPC469558

Natural Product ID:  NPC469558
Common Name:   Altaicalarin D
IUPAC Name:   [(1S,2S,3R,4S,6S)-4-acetyloxy-3-[4-(3,3-dimethyloxiran-2-yl)-3-[(Z)-2-methylbut-2-enoyl]oxybut-1-en-2-yl]-6-methyl-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl] (Z)-2-methylbut-2-enoate
Synonyms:   altaicalarin D
Molecular Formula:   C27H36O9
Standard InCHIKey:  VMZMBTIZKOPION-LAFIFDADSA-N
Standard InCHI:  InChI=1S/C27H36O9/c1-10-13(3)24(30)33-17(12-18-26(7,8)35-18)15(5)19-20(32-16(6)28)22(29)27(9)23(36-27)21(19)34-25(31)14(4)11-2/h10-11,17-21,23H,5,12H2,1-4,6-9H3/b13-10-,14-11-/t17?,18?,19-,20-,21-,23-,27+/m0/s1
Canonical SMILES:  C/C=C(C(=O)O[C@H]1[C@@H](C(=C)C(CC2OC2(C)C)OC(=O)/C(=CC)/C)[C@H](OC(=O)C)C(=O)[C@@]2([C@H]1O2)C)/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
NPO12711 Ligularia altaica Species Asteraceae Eukaryota PMID[20073490]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified EC50 = 18.9 ug/ml 24582402
NPT81 Cell Line A549 Homo sapiens EC50 > 20 ug/ml 22545792
NPT83 Cell Line MCF7 Homo sapiens EC50 > 20 ug/ml 22545792
NPT91 Cell Line KB Homo sapiens EC50 > 20 ug/ml 22545792

  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 NPC469558 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
0.96 High Similarity NPC474716
0.9 High Similarity NPC469551
0.8365 Intermediate Similarity NPC264477
0.8365 Intermediate Similarity NPC477511
0.8349 Intermediate Similarity NPC194619
0.8333 Intermediate Similarity NPC471934
0.8273 Intermediate Similarity NPC471933
0.8265 Intermediate Similarity NPC475087
0.8257 Intermediate Similarity NPC473975
0.8257 Intermediate Similarity NPC473594
0.8257 Intermediate Similarity NPC474586
0.8257 Intermediate Similarity NPC473843
0.8224 Intermediate Similarity NPC470975
0.8224 Intermediate Similarity NPC470979
0.8224 Intermediate Similarity NPC103088
0.8214 Intermediate Similarity NPC477509
0.8198 Intermediate Similarity NPC33360
0.8198 Intermediate Similarity NPC477126
0.819 Intermediate Similarity NPC473802
0.8131 Intermediate Similarity NPC471143
0.8131 Intermediate Similarity NPC477127
0.8131 Intermediate Similarity NPC477510
0.812 Intermediate Similarity NPC473709
0.812 Intermediate Similarity NPC473919
0.8095 Intermediate Similarity NPC477512
0.8077 Intermediate Similarity NPC471140
0.8058 Intermediate Similarity NPC469583
0.8051 Intermediate Similarity NPC471939
0.8034 Intermediate Similarity NPC472399
0.8019 Intermediate Similarity NPC201718
0.7983 Intermediate Similarity NPC471940
0.7982 Intermediate Similarity NPC477513
0.7982 Intermediate Similarity NPC475587
0.7982 Intermediate Similarity NPC296822
0.7982 Intermediate Similarity NPC475510
0.7981 Intermediate Similarity NPC472997
0.7981 Intermediate Similarity NPC472996
0.7981 Intermediate Similarity NPC17585
0.7946 Intermediate Similarity NPC317687
0.7941 Intermediate Similarity NPC20713
0.7928 Intermediate Similarity NPC253906
0.7913 Intermediate Similarity NPC240509
0.7909 Intermediate Similarity NPC473595
0.7909 Intermediate Similarity NPC473939
0.7905 Intermediate Similarity NPC472998
0.7895 Intermediate Similarity NPC474333
0.7863 Intermediate Similarity NPC472401
0.7857 Intermediate Similarity NPC317107
0.7857 Intermediate Similarity NPC475495
0.7843 Intermediate Similarity NPC475748
0.783 Intermediate Similarity NPC264378
0.7797 Intermediate Similarity NPC19464
0.7788 Intermediate Similarity NPC477093
0.7788 Intermediate Similarity NPC473522
0.7788 Intermediate Similarity NPC475277
0.7788 Intermediate Similarity NPC471147
0.7778 Intermediate Similarity NPC471126
0.7778 Intermediate Similarity NPC157252
0.7778 Intermediate Similarity NPC471128
0.7778 Intermediate Similarity NPC145182
0.7778 Intermediate Similarity NPC39996
0.7769 Intermediate Similarity NPC236999
0.7768 Intermediate Similarity NPC281624
0.776 Intermediate Similarity NPC68282
0.775 Intermediate Similarity NPC470973
0.775 Intermediate Similarity NPC225049
0.7748 Intermediate Similarity NPC322903
0.7739 Intermediate Similarity NPC476710
0.7739 Intermediate Similarity NPC270478
0.7739 Intermediate Similarity NPC476711
0.7736 Intermediate Similarity NPC236176
0.7724 Intermediate Similarity NPC476193
0.7724 Intermediate Similarity NPC180902
0.7724 Intermediate Similarity NPC475139
0.7719 Intermediate Similarity NPC159333
0.7719 Intermediate Similarity NPC470120
0.7712 Intermediate Similarity NPC52839
0.7692 Intermediate Similarity NPC472667
0.7692 Intermediate Similarity NPC470186
0.7685 Intermediate Similarity NPC474339
0.7685 Intermediate Similarity NPC15993
0.7685 Intermediate Similarity NPC164598
0.7679 Intermediate Similarity NPC469370
0.7672 Intermediate Similarity NPC476713
0.7672 Intermediate Similarity NPC58662
0.7672 Intermediate Similarity NPC476712
0.7667 Intermediate Similarity NPC24651
0.7664 Intermediate Similarity NPC471932
0.7664 Intermediate Similarity NPC208233
0.7658 Intermediate Similarity NPC266514
0.7658 Intermediate Similarity NPC180744
0.7647 Intermediate Similarity NPC475902
0.7647 Intermediate Similarity NPC162009
0.7647 Intermediate Similarity NPC257017
0.7642 Intermediate Similarity NPC472995
0.7642 Intermediate Similarity NPC35498
0.7642 Intermediate Similarity NPC476275
0.7636 Intermediate Similarity NPC474741
0.7632 Intermediate Similarity NPC473877
0.7627 Intermediate Similarity NPC4548
0.7623 Intermediate Similarity NPC476859
0.7619 Intermediate Similarity NPC66581
0.7615 Intermediate Similarity NPC149371
0.7615 Intermediate Similarity NPC320019
0.7615 Intermediate Similarity NPC324017
0.7615 Intermediate Similarity NPC471148
0.7607 Intermediate Similarity NPC251310
0.7607 Intermediate Similarity NPC472397
0.7607 Intermediate Similarity NPC171905
0.7607 Intermediate Similarity NPC472758
0.7607 Intermediate Similarity NPC471125
0.7603 Intermediate Similarity NPC217901
0.7603 Intermediate Similarity NPC473635
0.76 Intermediate Similarity NPC100017
0.76 Intermediate Similarity NPC475154
0.76 Intermediate Similarity NPC475500
0.76 Intermediate Similarity NPC182266
0.76 Intermediate Similarity NPC471137
0.76 Intermediate Similarity NPC471136
0.76 Intermediate Similarity NPC223356
0.76 Intermediate Similarity NPC473548
0.7586 Intermediate Similarity NPC190185
0.7586 Intermediate Similarity NPC154363
0.7586 Intermediate Similarity NPC213084
0.7586 Intermediate Similarity NPC471127
0.7586 Intermediate Similarity NPC470793
0.7586 Intermediate Similarity NPC234858
0.7583 Intermediate Similarity NPC67251
0.7583 Intermediate Similarity NPC18945
0.7583 Intermediate Similarity NPC265557
0.7583 Intermediate Similarity NPC91693
0.7583 Intermediate Similarity NPC105926
0.757 Intermediate Similarity NPC474921
0.7565 Intermediate Similarity NPC94509
0.7563 Intermediate Similarity NPC310511
0.7563 Intermediate Similarity NPC470779
0.7561 Intermediate Similarity NPC162495
0.7549 Intermediate Similarity NPC231889
0.7545 Intermediate Similarity NPC472755
0.7545 Intermediate Similarity NPC474166
0.7545 Intermediate Similarity NPC19239
0.7542 Intermediate Similarity NPC22628
0.7542 Intermediate Similarity NPC255081
0.7542 Intermediate Similarity NPC5991
0.7542 Intermediate Similarity NPC475520
0.7542 Intermediate Similarity NPC476107
0.7542 Intermediate Similarity NPC275696
0.7542 Intermediate Similarity NPC5989
0.7542 Intermediate Similarity NPC471108
0.7541 Intermediate Similarity NPC168849
0.7541 Intermediate Similarity NPC475273
0.7525 Intermediate Similarity NPC474547
0.7523 Intermediate Similarity NPC47880
0.7523 Intermediate Similarity NPC476478
0.7523 Intermediate Similarity NPC476270
0.7521 Intermediate Similarity NPC469684
0.7521 Intermediate Similarity NPC10721
0.7521 Intermediate Similarity NPC475305
0.7521 Intermediate Similarity NPC145238
0.7521 Intermediate Similarity NPC470922
0.7521 Intermediate Similarity NPC476729
0.7521 Intermediate Similarity NPC471146
0.7521 Intermediate Similarity NPC470778
0.7521 Intermediate Similarity NPC146432
0.75 Intermediate Similarity NPC312833
0.75 Intermediate Similarity NPC170538
0.75 Intermediate Similarity NPC80650
0.75 Intermediate Similarity NPC475606
0.75 Intermediate Similarity NPC299849
0.75 Intermediate Similarity NPC476852
0.75 Intermediate Similarity NPC251564
0.75 Intermediate Similarity NPC474213
0.75 Intermediate Similarity NPC476855
0.75 Intermediate Similarity NPC475314
0.75 Intermediate Similarity NPC477189
0.75 Intermediate Similarity NPC469718
0.75 Intermediate Similarity NPC329857
0.748 Intermediate Similarity NPC477713
0.748 Intermediate Similarity NPC477712
0.7479 Intermediate Similarity NPC143755
0.7479 Intermediate Similarity NPC317635
0.7479 Intermediate Similarity NPC329008
0.7478 Intermediate Similarity NPC475391
0.7477 Intermediate Similarity NPC76862
0.7477 Intermediate Similarity NPC158416
0.7477 Intermediate Similarity NPC118159
0.7477 Intermediate Similarity NPC39859
0.7477 Intermediate Similarity NPC470883
0.7477 Intermediate Similarity NPC279722
0.7477 Intermediate Similarity NPC476315
0.7459 Intermediate Similarity NPC293112
0.7458 Intermediate Similarity NPC124676
0.7458 Intermediate Similarity NPC146280
0.7458 Intermediate Similarity NPC475401
0.7458 Intermediate Similarity NPC470420
0.7458 Intermediate Similarity NPC473720
0.7456 Intermediate Similarity NPC89408
0.7456 Intermediate Similarity NPC100908
0.7455 Intermediate Similarity NPC472754
0.7453 Intermediate Similarity NPC473316

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469558 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
0.7593 Intermediate Similarity NPD6648 Approved
0.7523 Intermediate Similarity NPD5344 Discontinued
0.75 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD46 Approved
0.717 Intermediate Similarity NPD6698 Approved
0.7069 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.6855 Remote Similarity NPD6921 Approved
0.6803 Remote Similarity NPD7115 Discovery
0.6774 Remote Similarity NPD6319 Approved
0.6723 Remote Similarity NPD6371 Approved
0.6697 Remote Similarity NPD7838 Discovery
0.6667 Remote Similarity NPD6008 Approved
0.6636 Remote Similarity NPD7983 Approved
0.6614 Remote Similarity NPD8328 Phase 3
0.6612 Remote Similarity NPD8297 Approved
0.6562 Remote Similarity NPD7492 Approved
0.6529 Remote Similarity NPD6649 Approved
0.6529 Remote Similarity NPD6650 Approved
0.6512 Remote Similarity NPD6616 Approved
0.6508 Remote Similarity NPD6054 Approved
0.65 Remote Similarity NPD6373 Approved
0.65 Remote Similarity NPD6372 Approved
0.6489 Remote Similarity NPD7319 Approved
0.6462 Remote Similarity NPD7078 Approved
0.6457 Remote Similarity NPD8513 Phase 3
0.6457 Remote Similarity NPD8515 Approved
0.6457 Remote Similarity NPD8516 Approved
0.6457 Remote Similarity NPD8517 Approved
0.6455 Remote Similarity NPD1695 Approved
0.6435 Remote Similarity NPD4225 Approved
0.6417 Remote Similarity NPD6899 Approved
0.6417 Remote Similarity NPD6881 Approved
0.6412 Remote Similarity NPD7736 Approved
0.6406 Remote Similarity NPD6370 Approved
0.6389 Remote Similarity NPD1694 Approved
0.6387 Remote Similarity NPD6402 Approved
0.6387 Remote Similarity NPD5739 Approved
0.6387 Remote Similarity NPD6675 Approved
0.6387 Remote Similarity NPD7128 Approved
0.6378 Remote Similarity NPD6059 Approved
0.6357 Remote Similarity NPD7604 Phase 2
0.6357 Remote Similarity NPD7642 Approved
0.6341 Remote Similarity NPD6882 Approved
0.6336 Remote Similarity NPD8293 Discontinued
0.6333 Remote Similarity NPD5697 Approved
0.6328 Remote Similarity NPD6016 Approved
0.6328 Remote Similarity NPD6015 Approved
0.6325 Remote Similarity NPD1700 Approved
0.6316 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6311 Remote Similarity NPD7102 Approved
0.6311 Remote Similarity NPD7290 Approved
0.6311 Remote Similarity NPD6883 Approved
0.6293 Remote Similarity NPD8029 Clinical (unspecified phase)
0.629 Remote Similarity NPD4632 Approved
0.6283 Remote Similarity NPD5778 Approved
0.6283 Remote Similarity NPD5779 Approved
0.6281 Remote Similarity NPD7320 Approved
0.6281 Remote Similarity NPD6686 Approved
0.6279 Remote Similarity NPD5988 Approved
0.627 Remote Similarity NPD8295 Clinical (unspecified phase)
0.627 Remote Similarity NPD6009 Approved
0.626 Remote Similarity NPD8130 Phase 1
0.626 Remote Similarity NPD7507 Approved
0.626 Remote Similarity NPD6617 Approved
0.626 Remote Similarity NPD6847 Approved
0.626 Remote Similarity NPD8413 Clinical (unspecified phase)
0.626 Remote Similarity NPD6869 Approved
0.625 Remote Similarity NPD3168 Discontinued
0.623 Remote Similarity NPD6012 Approved
0.623 Remote Similarity NPD6013 Approved
0.623 Remote Similarity NPD6014 Approved
0.6228 Remote Similarity NPD5282 Discontinued
0.6212 Remote Similarity NPD8074 Phase 3
0.6202 Remote Similarity NPD5983 Phase 2
0.6198 Remote Similarity NPD5701 Approved
0.6159 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6154 Remote Similarity NPD7638 Approved
0.6148 Remote Similarity NPD7260 Phase 2
0.6148 Remote Similarity NPD6011 Approved
0.6136 Remote Similarity NPD6336 Discontinued
0.6107 Remote Similarity NPD7830 Approved
0.6107 Remote Similarity NPD7829 Approved
0.6102 Remote Similarity NPD7639 Approved
0.6102 Remote Similarity NPD7640 Approved
0.6087 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6087 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6087 Remote Similarity NPD7900 Approved
0.608 Remote Similarity NPD6053 Discontinued
0.6048 Remote Similarity NPD4634 Approved
0.6047 Remote Similarity NPD7516 Approved
0.6014 Remote Similarity NPD8415 Approved
0.6 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6 Remote Similarity NPD3653 Clinical (unspecified phase)
0.5985 Remote Similarity NPD8338 Approved
0.5983 Remote Similarity NPD7839 Suspended
0.5982 Remote Similarity NPD3573 Approved
0.5969 Remote Similarity NPD7328 Approved
0.5969 Remote Similarity NPD7327 Approved
0.5965 Remote Similarity NPD5785 Approved
0.5963 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5938 Remote Similarity NPD6274 Approved
0.5932 Remote Similarity NPD7902 Approved
0.5929 Remote Similarity NPD5737 Approved
0.5929 Remote Similarity NPD6672 Approved
0.5926 Remote Similarity NPD6033 Approved
0.5923 Remote Similarity NPD7101 Approved
0.5923 Remote Similarity NPD7100 Approved
0.5913 Remote Similarity NPD5693 Phase 1
0.5909 Remote Similarity NPD6110 Phase 1
0.5877 Remote Similarity NPD6101 Approved
0.5877 Remote Similarity NPD5764 Clinical (unspecified phase)
0.587 Remote Similarity NPD6845 Suspended
0.5868 Remote Similarity NPD5211 Phase 2
0.5846 Remote Similarity NPD6335 Approved
0.584 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5833 Remote Similarity NPD5285 Approved
0.5833 Remote Similarity NPD5286 Approved
0.5833 Remote Similarity NPD4696 Approved
0.5818 Remote Similarity NPD5209 Approved
0.5812 Remote Similarity NPD7748 Approved
0.5804 Remote Similarity NPD5363 Approved
0.58 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5798 Remote Similarity NPD6084 Phase 2
0.5798 Remote Similarity NPD6083 Phase 2
0.5798 Remote Similarity NPD4755 Approved
0.5789 Remote Similarity NPD8080 Discontinued
0.5781 Remote Similarity NPD8133 Approved
0.5778 Remote Similarity NPD8273 Phase 1
0.5778 Remote Similarity NPD8451 Approved
0.5776 Remote Similarity NPD6411 Approved
0.5772 Remote Similarity NPD5141 Approved
0.5769 Remote Similarity NPD6317 Approved
0.5763 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5763 Remote Similarity NPD5695 Phase 3
0.5752 Remote Similarity NPD5786 Approved
0.575 Remote Similarity NPD5696 Approved
0.5739 Remote Similarity NPD6904 Approved
0.5739 Remote Similarity NPD6080 Approved
0.5739 Remote Similarity NPD6673 Approved
0.5738 Remote Similarity NPD5226 Approved
0.5738 Remote Similarity NPD5225 Approved
0.5738 Remote Similarity NPD5224 Approved
0.5738 Remote Similarity NPD4633 Approved
0.5735 Remote Similarity NPD8448 Approved
0.5726 Remote Similarity NPD6399 Phase 3
0.5726 Remote Similarity NPD5357 Phase 1
0.5725 Remote Similarity NPD7641 Discontinued
0.5725 Remote Similarity NPD6313 Approved
0.5725 Remote Similarity NPD6314 Approved
0.5714 Remote Similarity NPD8444 Approved
0.5714 Remote Similarity NPD6908 Approved
0.5714 Remote Similarity NPD6909 Approved
0.5714 Remote Similarity NPD8378 Approved
0.5714 Remote Similarity NPD8380 Approved
0.5714 Remote Similarity NPD8296 Approved
0.5714 Remote Similarity NPD8379 Approved
0.5714 Remote Similarity NPD8033 Approved
0.5714 Remote Similarity NPD8335 Approved
0.5702 Remote Similarity NPD4700 Approved
0.5697 Remote Similarity NPD8368 Discontinued
0.5692 Remote Similarity NPD6868 Approved
0.5691 Remote Similarity NPD5174 Approved
0.5691 Remote Similarity NPD5175 Approved
0.5669 Remote Similarity NPD2067 Discontinued
0.5656 Remote Similarity NPD5223 Approved
0.5649 Remote Similarity NPD7500 Approved
0.5641 Remote Similarity NPD6050 Approved
0.5641 Remote Similarity NPD7515 Phase 2
0.5639 Remote Similarity NPD8377 Approved
0.5639 Remote Similarity NPD8294 Approved
0.5638 Remote Similarity NPD6190 Approved
0.5635 Remote Similarity NPD4729 Approved
0.5635 Remote Similarity NPD4730 Approved
0.5614 Remote Similarity NPD5330 Approved
0.5614 Remote Similarity NPD7521 Approved
0.5614 Remote Similarity NPD7334 Approved
0.5614 Remote Similarity NPD7146 Approved
0.5614 Remote Similarity NPD6684 Approved
0.5614 Remote Similarity NPD6409 Approved
0.5612 Remote Similarity NPD8391 Approved
0.5612 Remote Similarity NPD8390 Approved
0.5612 Remote Similarity NPD8392 Approved
0.561 Remote Similarity NPD8300 Approved
0.561 Remote Similarity NPD7632 Discontinued
0.561 Remote Similarity NPD8301 Approved
0.56 Remote Similarity NPD4768 Approved
0.56 Remote Similarity NPD4767 Approved

Structure

External Identifiers

PubChem CID   46186621
ChEMBL   CHEMBL1087160
ZINC  

Physicochemical Properties

Molecular Weight:  504.24
ALogP:  2.1798
MLogP:  3.44
XLogP:  2.537
# Rotatable Bonds:  20
Polar Surface Area:  121.03
# H-Bond Aceptor:  9
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  36

Download Data

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Structure MOL file  
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Biological Activities  
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