Natural Product: NPC64153

Natural Product ID:  NPC64153
Common Name:   Vernoflexin
IUPAC Name:   [(3aS,6aS,8S,9aR,9bS)-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl] 3-methylbut-2-enoate
Synonyms:   Vernoflexin
Molecular Formula:   C20H24O4
Standard InCHIKey:  CEKDWOBPPFOCDL-MGGVOPSTSA-N
Standard InCHI:  InChI=1S/C20H24O4/c1-10(2)8-17(21)23-16-9-15-11(3)6-7-14-12(4)20(22)24-19(14)18(15)13(16)5/h8,14-16,18-19H,3-7,9H2,1-2H3/t14-,15+,16-,18-,19-/m0/s1
Canonical SMILES:  CC(=CC(=O)O[C@H]1C[C@H]2[C@H](C1=C)[C@H]1OC(=O)C(=C)[C@@H]1CCC2=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
NPO33469 Asteraceae Family Asteraceae Eukaryota PMID[18329753]
NPO4027 Baccharoides anthelmintica Species Asteraceae Eukaryota TCMID*
NPO27182 Chrysolaena flexuosa Species Asteraceae Eukaryota TCMID*
NPO12623 Vernonia chinense Species Asteraceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT91 Cell Line KB Homo sapiens ED50 = 4.3 umol/ml 18329753

  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 NPC64153 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
0.95 High Similarity NPC246076
0.9186 High Similarity NPC475925
0.9048 High Similarity NPC304558
0.8989 High Similarity NPC24956
0.8989 High Similarity NPC18019
0.8941 High Similarity NPC24728
0.8837 High Similarity NPC207114
0.8837 High Similarity NPC471149
0.8837 High Similarity NPC217983
0.8764 High Similarity NPC477131
0.8736 High Similarity NPC283409
0.8736 High Similarity NPC472872
0.8706 High Similarity NPC235792
0.8667 High Similarity NPC67584
0.8636 High Similarity NPC19087
0.8636 High Similarity NPC297474
0.8636 High Similarity NPC54065
0.8621 High Similarity NPC79549
0.8605 High Similarity NPC107787
0.8605 High Similarity NPC187661
0.8602 High Similarity NPC171759
0.8588 High Similarity NPC224386
0.8588 High Similarity NPC194859
0.8571 High Similarity NPC213078
0.8556 High Similarity NPC470013
0.8556 High Similarity NPC127019
0.8556 High Similarity NPC198853
0.8556 High Similarity NPC262133
0.8556 High Similarity NPC323008
0.8556 High Similarity NPC470010
0.8539 High Similarity NPC57304
0.8539 High Similarity NPC133888
0.8539 High Similarity NPC191339
0.8539 High Similarity NPC184063
0.8539 High Similarity NPC293001
0.8539 High Similarity NPC133698
0.8539 High Similarity NPC286341
0.8539 High Similarity NPC171360
0.8539 High Similarity NPC63193
0.8539 High Similarity NPC29821
0.8539 High Similarity NPC35959
0.8523 High Similarity NPC155935
0.8523 High Similarity NPC4986
0.8523 High Similarity NPC38392
0.8523 High Similarity NPC215556
0.8506 High Similarity NPC118601
0.8506 High Similarity NPC270270
0.85 High Similarity NPC320537
0.85 High Similarity NPC143979
0.8488 Intermediate Similarity NPC300082
0.8488 Intermediate Similarity NPC284534
0.8488 Intermediate Similarity NPC78089
0.8488 Intermediate Similarity NPC204105
0.8478 Intermediate Similarity NPC213947
0.8478 Intermediate Similarity NPC170143
0.8478 Intermediate Similarity NPC108475
0.8478 Intermediate Similarity NPC161493
0.8471 Intermediate Similarity NPC54468
0.8462 Intermediate Similarity NPC213698
0.8462 Intermediate Similarity NPC304886
0.8462 Intermediate Similarity NPC52044
0.8444 Intermediate Similarity NPC135776
0.8434 Intermediate Similarity NPC182550
0.8427 Intermediate Similarity NPC301969
0.8427 Intermediate Similarity NPC216284
0.8427 Intermediate Similarity NPC62815
0.8427 Intermediate Similarity NPC37607
0.8427 Intermediate Similarity NPC35809
0.8409 Intermediate Similarity NPC224652
0.8409 Intermediate Similarity NPC91248
0.8409 Intermediate Similarity NPC178875
0.8404 Intermediate Similarity NPC150923
0.8391 Intermediate Similarity NPC284902
0.8391 Intermediate Similarity NPC56593
0.8372 Intermediate Similarity NPC115786
0.8333 Intermediate Similarity NPC131209
0.8333 Intermediate Similarity NPC276356
0.8333 Intermediate Similarity NPC221282
0.8333 Intermediate Similarity NPC69271
0.8333 Intermediate Similarity NPC155215
0.8333 Intermediate Similarity NPC74673
0.8295 Intermediate Similarity NPC475703
0.8276 Intermediate Similarity NPC215364
0.8261 Intermediate Similarity NPC472873
0.8261 Intermediate Similarity NPC170120
0.8261 Intermediate Similarity NPC167893
0.8261 Intermediate Similarity NPC476053
0.8261 Intermediate Similarity NPC163228
0.8261 Intermediate Similarity NPC224689
0.8256 Intermediate Similarity NPC318468
0.8256 Intermediate Similarity NPC128246
0.8247 Intermediate Similarity NPC54737
0.8242 Intermediate Similarity NPC258216
0.8242 Intermediate Similarity NPC472874
0.8235 Intermediate Similarity NPC25684
0.8235 Intermediate Similarity NPC126248
0.8235 Intermediate Similarity NPC301477
0.8235 Intermediate Similarity NPC47635
0.8235 Intermediate Similarity NPC281949
0.8193 Intermediate Similarity NPC476794
0.8193 Intermediate Similarity NPC470240
0.8193 Intermediate Similarity NPC208223
0.8191 Intermediate Similarity NPC221615
0.8182 Intermediate Similarity NPC67493
0.8182 Intermediate Similarity NPC50637
0.8182 Intermediate Similarity NPC238593
0.8172 Intermediate Similarity NPC142529
0.8172 Intermediate Similarity NPC91771
0.8172 Intermediate Similarity NPC126156
0.8152 Intermediate Similarity NPC473331
0.8132 Intermediate Similarity NPC290651
0.8125 Intermediate Similarity NPC86077
0.8118 Intermediate Similarity NPC290508
0.8118 Intermediate Similarity NPC6823
0.8118 Intermediate Similarity NPC302426
0.8118 Intermediate Similarity NPC293418
0.8118 Intermediate Similarity NPC73052
0.8111 Intermediate Similarity NPC166919
0.8111 Intermediate Similarity NPC288699
0.8111 Intermediate Similarity NPC295312
0.8111 Intermediate Similarity NPC32922
0.809 Intermediate Similarity NPC160138
0.809 Intermediate Similarity NPC231889
0.8085 Intermediate Similarity NPC474313
0.8085 Intermediate Similarity NPC471150
0.8072 Intermediate Similarity NPC123360
0.8049 Intermediate Similarity NPC476355
0.8046 Intermediate Similarity NPC245665
0.8046 Intermediate Similarity NPC39588
0.8046 Intermediate Similarity NPC272814
0.8046 Intermediate Similarity NPC111409
0.8043 Intermediate Similarity NPC473234
0.8043 Intermediate Similarity NPC60386
0.8043 Intermediate Similarity NPC200237
0.8043 Intermediate Similarity NPC308656
0.8043 Intermediate Similarity NPC473273
0.8043 Intermediate Similarity NPC473263
0.8043 Intermediate Similarity NPC475657
0.8043 Intermediate Similarity NPC153590
0.8023 Intermediate Similarity NPC255580
0.8023 Intermediate Similarity NPC141810
0.8023 Intermediate Similarity NPC39411
0.8022 Intermediate Similarity NPC312042
0.8 Intermediate Similarity NPC5714
0.8 Intermediate Similarity NPC59489
0.8 Intermediate Similarity NPC139838
0.798 Intermediate Similarity NPC26617
0.7978 Intermediate Similarity NPC309757
0.7978 Intermediate Similarity NPC261253
0.7978 Intermediate Similarity NPC470242
0.7978 Intermediate Similarity NPC236692
0.7978 Intermediate Similarity NPC474045
0.7976 Intermediate Similarity NPC65603
0.7957 Intermediate Similarity NPC140543
0.7957 Intermediate Similarity NPC474338
0.7957 Intermediate Similarity NPC476267
0.7957 Intermediate Similarity NPC473316
0.7957 Intermediate Similarity NPC473330
0.7935 Intermediate Similarity NPC74103
0.7935 Intermediate Similarity NPC150978
0.7935 Intermediate Similarity NPC70595
0.7935 Intermediate Similarity NPC284185
0.7935 Intermediate Similarity NPC123177
0.7931 Intermediate Similarity NPC173609
0.7917 Intermediate Similarity NPC186861
0.7912 Intermediate Similarity NPC268298
0.7907 Intermediate Similarity NPC258965
0.7907 Intermediate Similarity NPC156658
0.7895 Intermediate Similarity NPC477949
0.7895 Intermediate Similarity NPC311904
0.7882 Intermediate Similarity NPC128276
0.7879 Intermediate Similarity NPC223450
0.7879 Intermediate Similarity NPC243998
0.7879 Intermediate Similarity NPC166115
0.7865 Intermediate Similarity NPC161957
0.7865 Intermediate Similarity NPC33570
0.7865 Intermediate Similarity NPC21471
0.7865 Intermediate Similarity NPC474547
0.7857 Intermediate Similarity NPC235906
0.7849 Intermediate Similarity NPC475838
0.7849 Intermediate Similarity NPC179746
0.7849 Intermediate Similarity NPC228451
0.7849 Intermediate Similarity NPC81419
0.7849 Intermediate Similarity NPC125674
0.7841 Intermediate Similarity NPC128429
0.7841 Intermediate Similarity NPC250315
0.7841 Intermediate Similarity NPC170286
0.7841 Intermediate Similarity NPC215294
0.7831 Intermediate Similarity NPC140287
0.7826 Intermediate Similarity NPC179394
0.7826 Intermediate Similarity NPC253144
0.7826 Intermediate Similarity NPC475855
0.7826 Intermediate Similarity NPC129419
0.7826 Intermediate Similarity NPC475748
0.7826 Intermediate Similarity NPC144133
0.7826 Intermediate Similarity NPC51004
0.7816 Intermediate Similarity NPC35089
0.7816 Intermediate Similarity NPC471325
0.7816 Intermediate Similarity NPC10276
0.7812 Intermediate Similarity NPC45125

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC64153 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
0.8523 High Similarity NPD1695 Approved
0.798 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD5785 Approved
0.7238 Intermediate Similarity NPD6371 Approved
0.7204 Intermediate Similarity NPD4249 Approved
0.7143 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4250 Approved
0.7128 Intermediate Similarity NPD4251 Approved
0.7103 Intermediate Similarity NPD6053 Discontinued
0.7097 Intermediate Similarity NPD5363 Approved
0.7097 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1694 Approved
0.7083 Intermediate Similarity NPD6698 Approved
0.7083 Intermediate Similarity NPD46 Approved
0.7065 Intermediate Similarity NPD5362 Discontinued
0.7019 Intermediate Similarity NPD6008 Approved
0.6931 Remote Similarity NPD7638 Approved
0.6863 Remote Similarity NPD7639 Approved
0.6863 Remote Similarity NPD7640 Approved
0.6774 Remote Similarity NPD4270 Approved
0.6774 Remote Similarity NPD4269 Approved
0.6739 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6735 Remote Similarity NPD7838 Discovery
0.6702 Remote Similarity NPD7154 Phase 3
0.6701 Remote Similarity NPD6903 Approved
0.67 Remote Similarity NPD5282 Discontinued
0.6667 Remote Similarity NPD7146 Approved
0.6667 Remote Similarity NPD5330 Approved
0.6667 Remote Similarity NPD5786 Approved
0.6667 Remote Similarity NPD5369 Approved
0.6667 Remote Similarity NPD7521 Approved
0.6667 Remote Similarity NPD7334 Approved
0.6667 Remote Similarity NPD6409 Approved
0.6667 Remote Similarity NPD6684 Approved
0.6596 Remote Similarity NPD6435 Approved
0.6596 Remote Similarity NPD5209 Approved
0.6574 Remote Similarity NPD6686 Approved
0.6559 Remote Similarity NPD4820 Approved
0.6559 Remote Similarity NPD4821 Approved
0.6559 Remote Similarity NPD4252 Approved
0.6559 Remote Similarity NPD4822 Approved
0.6559 Remote Similarity NPD4819 Approved
0.6531 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6526 Remote Similarity NPD5332 Approved
0.6526 Remote Similarity NPD5331 Approved
0.6522 Remote Similarity NPD4271 Approved
0.6522 Remote Similarity NPD4268 Approved
0.65 Remote Similarity NPD5693 Phase 1
0.6489 Remote Similarity NPD4790 Discontinued
0.6471 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6471 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6442 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6442 Remote Similarity NPD4225 Approved
0.6436 Remote Similarity NPD6399 Phase 3
0.64 Remote Similarity NPD5207 Approved
0.6383 Remote Similarity NPD5368 Approved
0.6364 Remote Similarity NPD6672 Approved
0.6364 Remote Similarity NPD5737 Approved
0.6344 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6337 Remote Similarity NPD7983 Approved
0.6275 Remote Similarity NPD5778 Approved
0.6275 Remote Similarity NPD5779 Approved
0.6262 Remote Similarity NPD7632 Discontinued
0.625 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6226 Remote Similarity NPD6648 Approved
0.6214 Remote Similarity NPD6001 Approved
0.6196 Remote Similarity NPD8039 Approved
0.6182 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6168 Remote Similarity NPD5344 Discontinued
0.6154 Remote Similarity NPD5695 Phase 3
0.6139 Remote Similarity NPD6904 Approved
0.6139 Remote Similarity NPD6051 Approved
0.6139 Remote Similarity NPD6673 Approved
0.6139 Remote Similarity NPD6080 Approved
0.6132 Remote Similarity NPD5696 Approved
0.6121 Remote Similarity NPD7115 Discovery
0.6116 Remote Similarity NPD7507 Approved
0.6078 Remote Similarity NPD5692 Phase 3
0.6058 Remote Similarity NPD7900 Approved
0.6058 Remote Similarity NPD7901 Clinical (unspecified phase)
0.604 Remote Similarity NPD5208 Approved
0.6038 Remote Similarity NPD6084 Phase 2
0.6038 Remote Similarity NPD6083 Phase 2
0.6036 Remote Similarity NPD6412 Phase 2
0.6036 Remote Similarity NPD5697 Approved
0.6019 Remote Similarity NPD6050 Approved
0.6019 Remote Similarity NPD5284 Approved
0.6019 Remote Similarity NPD8034 Phase 2
0.6019 Remote Similarity NPD7637 Suspended
0.6019 Remote Similarity NPD8035 Phase 2
0.6019 Remote Similarity NPD5694 Approved
0.6019 Remote Similarity NPD5281 Approved
0.6018 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6 Remote Similarity NPD7260 Phase 2
0.6 Remote Similarity NPD4632 Approved
0.5982 Remote Similarity NPD6011 Approved
0.5982 Remote Similarity NPD6881 Approved
0.5982 Remote Similarity NPD6899 Approved
0.5982 Remote Similarity NPD7320 Approved
0.5968 Remote Similarity NPD7319 Approved
0.5965 Remote Similarity NPD6650 Approved
0.5965 Remote Similarity NPD6649 Approved
0.596 Remote Similarity NPD3665 Phase 1
0.596 Remote Similarity NPD3133 Approved
0.596 Remote Similarity NPD3666 Approved
0.5952 Remote Similarity NPD6845 Suspended
0.5946 Remote Similarity NPD6675 Approved
0.5946 Remote Similarity NPD5739 Approved
0.5946 Remote Similarity NPD7128 Approved
0.5946 Remote Similarity NPD6402 Approved
0.5929 Remote Similarity NPD6013 Approved
0.5929 Remote Similarity NPD6372 Approved
0.5929 Remote Similarity NPD6012 Approved
0.5929 Remote Similarity NPD6373 Approved
0.5929 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5929 Remote Similarity NPD6014 Approved
0.5909 Remote Similarity NPD6052 Approved
0.5902 Remote Similarity NPD7492 Approved
0.5893 Remote Similarity NPD5701 Approved
0.5888 Remote Similarity NPD7902 Approved
0.5877 Remote Similarity NPD6883 Approved
0.5877 Remote Similarity NPD7290 Approved
0.5877 Remote Similarity NPD7102 Approved
0.5854 Remote Similarity NPD6616 Approved
0.5847 Remote Similarity NPD6009 Approved
0.5842 Remote Similarity NPD3618 Phase 1
0.5842 Remote Similarity NPD6098 Approved
0.5833 Remote Similarity NPD4802 Phase 2
0.5833 Remote Similarity NPD6319 Approved
0.5833 Remote Similarity NPD4238 Approved
0.5833 Remote Similarity NPD6054 Approved
0.5826 Remote Similarity NPD8130 Phase 1
0.5826 Remote Similarity NPD6617 Approved
0.5826 Remote Similarity NPD6847 Approved
0.5826 Remote Similarity NPD2181 Clinical (unspecified phase)
0.5826 Remote Similarity NPD6869 Approved
0.5825 Remote Similarity NPD6101 Approved
0.5825 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5806 Remote Similarity NPD7078 Approved
0.58 Remote Similarity NPD3668 Phase 3
0.5798 Remote Similarity NPD7328 Approved
0.5798 Remote Similarity NPD7327 Approved
0.5794 Remote Similarity NPD7839 Suspended
0.5794 Remote Similarity NPD6007 Clinical (unspecified phase)
0.5785 Remote Similarity NPD5983 Phase 2
0.5785 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5785 Remote Similarity NPD6016 Approved
0.5785 Remote Similarity NPD8517 Approved
0.5785 Remote Similarity NPD8516 Approved
0.5785 Remote Similarity NPD8515 Approved
0.5785 Remote Similarity NPD8513 Phase 3
0.5785 Remote Similarity NPD8033 Approved
0.5785 Remote Similarity NPD6015 Approved
0.5776 Remote Similarity NPD8297 Approved
0.5776 Remote Similarity NPD6882 Approved
0.576 Remote Similarity NPD7736 Approved
0.5758 Remote Similarity NPD3667 Approved
0.5755 Remote Similarity NPD7748 Approved
0.575 Remote Similarity NPD7516 Approved
0.5739 Remote Similarity NPD2067 Discontinued
0.5738 Remote Similarity NPD6370 Approved
0.5738 Remote Similarity NPD5988 Approved
0.5729 Remote Similarity NPD4756 Discovery
0.5726 Remote Similarity NPD8133 Approved
0.5714 Remote Similarity NPD6411 Approved
0.5702 Remote Similarity NPD6059 Approved
0.5702 Remote Similarity NPD8294 Approved
0.5702 Remote Similarity NPD8377 Approved
0.5701 Remote Similarity NPD4629 Approved
0.5701 Remote Similarity NPD5210 Approved
0.5701 Remote Similarity NPD5654 Approved
0.5698 Remote Similarity NPD3198 Approved
0.5691 Remote Similarity NPD7604 Phase 2
0.569 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5686 Remote Similarity NPD5279 Phase 3
0.568 Remote Similarity NPD8293 Discontinued
0.5676 Remote Similarity NPD5211 Phase 2
0.5673 Remote Similarity NPD4753 Phase 2
0.5673 Remote Similarity NPD5370 Suspended
0.566 Remote Similarity NPD4202 Approved
0.5656 Remote Similarity NPD8378 Approved
0.5656 Remote Similarity NPD8380 Approved
0.5656 Remote Similarity NPD8296 Approved
0.5656 Remote Similarity NPD8379 Approved
0.5656 Remote Similarity NPD7503 Approved
0.5656 Remote Similarity NPD8335 Approved
0.5644 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5644 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5644 Remote Similarity NPD4786 Approved
0.5636 Remote Similarity NPD4696 Approved
0.5636 Remote Similarity NPD5285 Approved
0.5636 Remote Similarity NPD5286 Approved
0.5635 Remote Similarity NPD8337 Approved
0.5635 Remote Similarity NPD8336 Approved
0.5631 Remote Similarity NPD3573 Approved
0.563 Remote Similarity NPD6274 Approved
0.5614 Remote Similarity NPD6685 Approved
0.5614 Remote Similarity NPD6614 Approved

Structure

External Identifiers

PubChem CID   44579992
ChEMBL   CHEMBL484679
ZINC  

Physicochemical Properties

Molecular Weight:  328.17
ALogP:  2.9011
MLogP:  3.22
XLogP:  2.672
# Rotatable Bonds:  5
Polar Surface Area:  52.6
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  24

Download Data

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