Natural Product: NPC44004

Natural Product ID:  NPC44004
Common Name:   Repin
IUPAC Name:   [(3aR,4S,6aR,8S,9R,9aS,9bS)-8-hydroxy-3,6-dimethylidene-2-oxospiro[3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-9,2'-oxirane]-4-yl] (2S)-2-methyloxirane-2-carboxylate
Synonyms:   Repin
Molecular Formula:   C19H22O7
Standard InCHIKey:  HQZJODBJOBTCPI-BQPPTCRNSA-N
Standard InCHI:  InChI=1S/C19H22O7/c1-8-4-11(25-17(22)18(3)6-23-18)13-9(2)16(21)26-15(13)14-10(8)5-12(20)19(14)7-24-19/h10-15,20H,1-2,4-7H2,3H3/t10-,11-,12-,13+,14-,15-,18-,19+/m0/s1
Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1[C@H](CC(=C)[C@H]1[C@@H]2[C@]2(OC2)[C@H](C1)O)OC(=O)[C@@]1(C)OC1
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
NPO30807 Acroptilon repens Species Asteraceae Eukaryota PMID[2348202]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 = 2500 nM 19928902
NPT81 Cell Line A549 Homo sapiens IC50 = 2500 nM 19928902
NPT2 Others Unspecified IC50 = 9240 nM 23290052
NPT309 Cell Line 1A9 Homo sapiens IC50 = 300 nM PubChem BioAssay data set
NPT2 Others Unspecified IC50 = 800 nM 21155593
NPT180 Cell Line HCT-8 Homo sapiens IC50 = 800 nM 21155593
NPT2 Others Unspecified Inhibition = 50 % 23398362
NPT91 Cell Line KB Homo sapiens IC50 = 1400 nM 23806109
NPT83 Cell Line MCF7 Homo sapiens IC50 = 1100 nM 23806109

  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 NPC44004 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
0.9184 High Similarity NPC45125
0.9082 High Similarity NPC474313
0.89 High Similarity NPC471381
0.89 High Similarity NPC186861
0.8878 High Similarity NPC472873
0.8762 High Similarity NPC139838
0.8762 High Similarity NPC59489
0.87 High Similarity NPC471150
0.87 High Similarity NPC311904
0.8673 High Similarity NPC475788
0.8654 High Similarity NPC54737
0.8571 High Similarity NPC155215
0.8571 High Similarity NPC184063
0.8557 High Similarity NPC215556
0.85 High Similarity NPC163228
0.8491 Intermediate Similarity NPC68248
0.8485 Intermediate Similarity NPC258216
0.8469 Intermediate Similarity NPC19087
0.8469 Intermediate Similarity NPC216284
0.8454 Intermediate Similarity NPC79549
0.8416 Intermediate Similarity NPC476009
0.8367 Intermediate Similarity NPC472872
0.8367 Intermediate Similarity NPC38392
0.8365 Intermediate Similarity NPC471148
0.8333 Intermediate Similarity NPC181151
0.8318 Intermediate Similarity NPC117604
0.8317 Intermediate Similarity NPC476053
0.8317 Intermediate Similarity NPC475900
0.8283 Intermediate Similarity NPC54065
0.8283 Intermediate Similarity NPC297474
0.8265 Intermediate Similarity NPC207114
0.8265 Intermediate Similarity NPC217983
0.8235 Intermediate Similarity NPC142529
0.8235 Intermediate Similarity NPC91771
0.8224 Intermediate Similarity NPC26617
0.8218 Intermediate Similarity NPC473331
0.82 Intermediate Similarity NPC171360
0.82 Intermediate Similarity NPC293001
0.82 Intermediate Similarity NPC35959
0.82 Intermediate Similarity NPC63193
0.82 Intermediate Similarity NPC133888
0.82 Intermediate Similarity NPC57304
0.82 Intermediate Similarity NPC29821
0.8182 Intermediate Similarity NPC155935
0.8144 Intermediate Similarity NPC284534
0.8144 Intermediate Similarity NPC204105
0.8144 Intermediate Similarity NPC300082
0.8142 Intermediate Similarity NPC475401
0.8131 Intermediate Similarity NPC243998
0.8119 Intermediate Similarity NPC473263
0.8119 Intermediate Similarity NPC473234
0.8119 Intermediate Similarity NPC308656
0.8119 Intermediate Similarity NPC472874
0.8119 Intermediate Similarity NPC60386
0.8119 Intermediate Similarity NPC473273
0.8113 Intermediate Similarity NPC473148
0.81 Intermediate Similarity NPC35809
0.8095 Intermediate Similarity NPC150923
0.807 Intermediate Similarity NPC477092
0.8061 Intermediate Similarity NPC304558
0.8061 Intermediate Similarity NPC187661
0.8056 Intermediate Similarity NPC477513
0.8053 Intermediate Similarity NPC475305
0.8037 Intermediate Similarity NPC474741
0.8036 Intermediate Similarity NPC121816
0.802 Intermediate Similarity NPC475881
0.802 Intermediate Similarity NPC70251
0.8019 Intermediate Similarity NPC474747
0.8 Intermediate Similarity NPC70865
0.7981 Intermediate Similarity NPC161493
0.798 Intermediate Similarity NPC270270
0.7965 Intermediate Similarity NPC255450
0.7965 Intermediate Similarity NPC170692
0.7963 Intermediate Similarity NPC223450
0.7963 Intermediate Similarity NPC474101
0.7961 Intermediate Similarity NPC67584
0.7961 Intermediate Similarity NPC52044
0.7961 Intermediate Similarity NPC213698
0.7946 Intermediate Similarity NPC273242
0.7944 Intermediate Similarity NPC475945
0.7944 Intermediate Similarity NPC475871
0.7941 Intermediate Similarity NPC153590
0.7941 Intermediate Similarity NPC200237
0.7938 Intermediate Similarity NPC245665
0.7938 Intermediate Similarity NPC111409
0.7925 Intermediate Similarity NPC474339
0.7925 Intermediate Similarity NPC164598
0.7925 Intermediate Similarity NPC201718
0.7925 Intermediate Similarity NPC471767
0.7925 Intermediate Similarity NPC171759
0.7921 Intermediate Similarity NPC246173
0.7909 Intermediate Similarity NPC115352
0.7905 Intermediate Similarity NPC49833
0.7905 Intermediate Similarity NPC249171
0.7905 Intermediate Similarity NPC221615
0.79 Intermediate Similarity NPC178875
0.7885 Intermediate Similarity NPC76862
0.7885 Intermediate Similarity NPC39859
0.7885 Intermediate Similarity NPC470883
0.7885 Intermediate Similarity NPC24956
0.7885 Intermediate Similarity NPC213078
0.7885 Intermediate Similarity NPC158416
0.7885 Intermediate Similarity NPC18019
0.7879 Intermediate Similarity NPC56593
0.7879 Intermediate Similarity NPC470242
0.7864 Intermediate Similarity NPC127019
0.7864 Intermediate Similarity NPC198853
0.7864 Intermediate Similarity NPC190294
0.7857 Intermediate Similarity NPC194859
0.7857 Intermediate Similarity NPC224386
0.7857 Intermediate Similarity NPC475924
0.7857 Intermediate Similarity NPC475851
0.785 Intermediate Similarity NPC250594
0.785 Intermediate Similarity NPC86077
0.7843 Intermediate Similarity NPC286341
0.7843 Intermediate Similarity NPC133698
0.7843 Intermediate Similarity NPC469627
0.7843 Intermediate Similarity NPC131209
0.7843 Intermediate Similarity NPC475925
0.7843 Intermediate Similarity NPC191339
0.7835 Intermediate Similarity NPC246076
0.7822 Intermediate Similarity NPC173926
0.781 Intermediate Similarity NPC471140
0.781 Intermediate Similarity NPC236580
0.781 Intermediate Similarity NPC304445
0.781 Intermediate Similarity NPC108475
0.781 Intermediate Similarity NPC170143
0.781 Intermediate Similarity NPC213947
0.78 Intermediate Similarity NPC24728
0.78 Intermediate Similarity NPC190753
0.78 Intermediate Similarity NPC186148
0.78 Intermediate Similarity NPC201658
0.78 Intermediate Similarity NPC118601
0.7788 Intermediate Similarity NPC170120
0.7778 Intermediate Similarity NPC124881
0.7768 Intermediate Similarity NPC475495
0.7767 Intermediate Similarity NPC212486
0.7757 Intermediate Similarity NPC474742
0.7757 Intermediate Similarity NPC476270
0.7755 Intermediate Similarity NPC128246
0.7745 Intermediate Similarity NPC65359
0.7745 Intermediate Similarity NPC206614
0.7745 Intermediate Similarity NPC474323
0.7736 Intermediate Similarity NPC474213
0.7723 Intermediate Similarity NPC58219
0.7723 Intermediate Similarity NPC53158
0.7723 Intermediate Similarity NPC471149
0.7723 Intermediate Similarity NPC224652
0.7723 Intermediate Similarity NPC177629
0.7706 Intermediate Similarity NPC100487
0.77 Intermediate Similarity NPC309757
0.77 Intermediate Similarity NPC236692
0.7699 Intermediate Similarity NPC477093
0.7699 Intermediate Similarity NPC475277
0.7699 Intermediate Similarity NPC473522
0.7692 Intermediate Similarity NPC262133
0.7692 Intermediate Similarity NPC470010
0.7692 Intermediate Similarity NPC323008
0.7692 Intermediate Similarity NPC470013
0.7692 Intermediate Similarity NPC477131
0.7685 Intermediate Similarity NPC80144
0.7679 Intermediate Similarity NPC193741
0.7679 Intermediate Similarity NPC257240
0.7664 Intermediate Similarity NPC475949
0.7658 Intermediate Similarity NPC110701
0.7647 Intermediate Similarity NPC12872
0.7647 Intermediate Similarity NPC168679
0.7647 Intermediate Similarity NPC474951
0.7647 Intermediate Similarity NPC92974
0.7647 Intermediate Similarity NPC4986
0.7647 Intermediate Similarity NPC283409
0.7642 Intermediate Similarity NPC261372
0.7642 Intermediate Similarity NPC328562
0.7642 Intermediate Similarity NPC323421
0.7642 Intermediate Similarity NPC58267
0.7642 Intermediate Similarity NPC263674
0.7629 Intermediate Similarity NPC156658
0.7629 Intermediate Similarity NPC258965
0.7623 Intermediate Similarity NPC13071
0.7619 Intermediate Similarity NPC270013
0.7619 Intermediate Similarity NPC14961
0.7619 Intermediate Similarity NPC224689
0.7615 Intermediate Similarity NPC475873
0.76 Intermediate Similarity NPC47958
0.76 Intermediate Similarity NPC149725
0.76 Intermediate Similarity NPC304509
0.7593 Intermediate Similarity NPC477511
0.7593 Intermediate Similarity NPC67296
0.7593 Intermediate Similarity NPC264477
0.7589 Intermediate Similarity NPC477102
0.7586 Intermediate Similarity NPC471146
0.7573 Intermediate Similarity NPC301969
0.7573 Intermediate Similarity NPC37607
0.7568 Intermediate Similarity NPC474421
0.7568 Intermediate Similarity NPC324327
0.7568 Intermediate Similarity NPC72813
0.7568 Intermediate Similarity NPC326994
0.7568 Intermediate Similarity NPC194620
0.7551 Intermediate Similarity NPC126248
0.7549 Intermediate Similarity NPC91248

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC44004 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
0.8224 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD6371 Approved
0.7647 Intermediate Similarity NPD1695 Approved
0.6972 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6916 Remote Similarity NPD6698 Approved
0.6916 Remote Similarity NPD46 Approved
0.6829 Remote Similarity NPD6319 Approved
0.6762 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6746 Remote Similarity NPD7492 Approved
0.6694 Remote Similarity NPD6054 Approved
0.6693 Remote Similarity NPD6616 Approved
0.6667 Remote Similarity NPD6053 Discontinued
0.6641 Remote Similarity NPD7078 Approved
0.664 Remote Similarity NPD6015 Approved
0.664 Remote Similarity NPD6016 Approved
0.6638 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6638 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6606 Remote Similarity NPD5785 Approved
0.6606 Remote Similarity NPD7838 Discovery
0.6589 Remote Similarity NPD7736 Approved
0.6587 Remote Similarity NPD6370 Approved
0.6587 Remote Similarity NPD5988 Approved
0.6585 Remote Similarity NPD7115 Discovery
0.6577 Remote Similarity NPD5282 Discontinued
0.656 Remote Similarity NPD6059 Approved
0.6542 Remote Similarity NPD4249 Approved
0.6538 Remote Similarity NPD5369 Approved
0.6522 Remote Similarity NPD5344 Discontinued
0.6522 Remote Similarity NPD1700 Approved
0.6512 Remote Similarity NPD8293 Discontinued
0.6481 Remote Similarity NPD4250 Approved
0.6481 Remote Similarity NPD4251 Approved
0.6449 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6449 Remote Similarity NPD5363 Approved
0.6446 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6417 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6415 Remote Similarity NPD5362 Discontinued
0.6396 Remote Similarity NPD7983 Approved
0.6348 Remote Similarity NPD4225 Approved
0.6341 Remote Similarity NPD4632 Approved
0.6333 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6321 Remote Similarity NPD4270 Approved
0.6321 Remote Similarity NPD4269 Approved
0.6303 Remote Similarity NPD6008 Approved
0.6288 Remote Similarity NPD7319 Approved
0.6261 Remote Similarity NPD6083 Phase 2
0.6261 Remote Similarity NPD6084 Phase 2
0.626 Remote Similarity NPD8297 Approved
0.625 Remote Similarity NPD5697 Approved
0.6241 Remote Similarity NPD5956 Approved
0.6239 Remote Similarity NPD5786 Approved
0.623 Remote Similarity NPD5955 Clinical (unspecified phase)
0.623 Remote Similarity NPD4634 Approved
0.6228 Remote Similarity NPD5695 Phase 3
0.621 Remote Similarity NPD8133 Approved
0.6207 Remote Similarity NPD5696 Approved
0.6198 Remote Similarity NPD6881 Approved
0.6198 Remote Similarity NPD7320 Approved
0.6198 Remote Similarity NPD6686 Approved
0.6198 Remote Similarity NPD6899 Approved
0.619 Remote Similarity NPD6009 Approved
0.6183 Remote Similarity NPD7507 Approved
0.6179 Remote Similarity NPD6650 Approved
0.6179 Remote Similarity NPD6649 Approved
0.6168 Remote Similarity NPD6435 Approved
0.6167 Remote Similarity NPD7128 Approved
0.6167 Remote Similarity NPD6675 Approved
0.6167 Remote Similarity NPD5739 Approved
0.6167 Remote Similarity NPD6402 Approved
0.6154 Remote Similarity NPD7604 Phase 2
0.6154 Remote Similarity NPD6648 Approved
0.6148 Remote Similarity NPD6373 Approved
0.6148 Remote Similarity NPD6012 Approved
0.6148 Remote Similarity NPD6372 Approved
0.6148 Remote Similarity NPD6013 Approved
0.6148 Remote Similarity NPD6014 Approved
0.6132 Remote Similarity NPD4822 Approved
0.6132 Remote Similarity NPD4820 Approved
0.6132 Remote Similarity NPD4252 Approved
0.6132 Remote Similarity NPD4819 Approved
0.6132 Remote Similarity NPD4821 Approved
0.6132 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6124 Remote Similarity NPD5983 Phase 2
0.6116 Remote Similarity NPD5701 Approved
0.6098 Remote Similarity NPD7290 Approved
0.6098 Remote Similarity NPD7102 Approved
0.6098 Remote Similarity NPD6883 Approved
0.609 Remote Similarity NPD6033 Approved
0.6066 Remote Similarity NPD6011 Approved
0.6048 Remote Similarity NPD6847 Approved
0.6048 Remote Similarity NPD6617 Approved
0.6048 Remote Similarity NPD6869 Approved
0.6048 Remote Similarity NPD8130 Phase 1
0.6 Remote Similarity NPD8516 Approved
0.6 Remote Similarity NPD8515 Approved
0.6 Remote Similarity NPD6882 Approved
0.6 Remote Similarity NPD8517 Approved
0.6 Remote Similarity NPD8513 Phase 3
0.5984 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5984 Remote Similarity NPD6412 Phase 2
0.5981 Remote Similarity NPD5368 Approved
0.5971 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5965 Remote Similarity NPD5693 Phase 1
0.5963 Remote Similarity NPD7154 Phase 3
0.5963 Remote Similarity NPD5331 Approved
0.5963 Remote Similarity NPD5332 Approved
0.5943 Remote Similarity NPD4268 Approved
0.5943 Remote Similarity NPD4271 Approved
0.594 Remote Similarity NPD6336 Discontinued
0.594 Remote Similarity NPD8273 Phase 1
0.5932 Remote Similarity NPD7638 Approved
0.5932 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5926 Remote Similarity NPD4790 Discontinued
0.5913 Remote Similarity NPD5778 Approved
0.5913 Remote Similarity NPD5779 Approved
0.5891 Remote Similarity NPD7328 Approved
0.5891 Remote Similarity NPD7327 Approved
0.5882 Remote Similarity NPD7640 Approved
0.5882 Remote Similarity NPD7639 Approved
0.5878 Remote Similarity NPD8033 Approved
0.5859 Remote Similarity NPD6274 Approved
0.5846 Remote Similarity NPD4522 Approved
0.5846 Remote Similarity NPD7516 Approved
0.5826 Remote Similarity NPD7637 Suspended
0.5812 Remote Similarity NPD5210 Approved
0.5812 Remote Similarity NPD4629 Approved
0.5802 Remote Similarity NPD8377 Approved
0.5802 Remote Similarity NPD8294 Approved
0.5794 Remote Similarity NPD2204 Approved
0.5794 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5794 Remote Similarity NPD4802 Phase 2
0.5794 Remote Similarity NPD4238 Approved
0.5789 Remote Similarity NPD4753 Phase 2
0.5789 Remote Similarity NPD7642 Approved
0.5785 Remote Similarity NPD5211 Phase 2
0.5778 Remote Similarity NPD8074 Phase 3
0.5776 Remote Similarity NPD6399 Phase 3
0.5763 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5758 Remote Similarity NPD8267 Approved
0.5758 Remote Similarity NPD8378 Approved
0.5758 Remote Similarity NPD8266 Approved
0.5758 Remote Similarity NPD8380 Approved
0.5758 Remote Similarity NPD8296 Approved
0.5758 Remote Similarity NPD8379 Approved
0.5758 Remote Similarity NPD7503 Approved
0.5758 Remote Similarity NPD8335 Approved
0.5758 Remote Similarity NPD6921 Approved
0.5758 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5758 Remote Similarity NPD8268 Approved
0.5758 Remote Similarity NPD8269 Approved
0.575 Remote Similarity NPD5285 Approved
0.575 Remote Similarity NPD4696 Approved
0.575 Remote Similarity NPD5286 Approved
0.5727 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5725 Remote Similarity NPD7101 Approved
0.5725 Remote Similarity NPD7100 Approved
0.5714 Remote Similarity NPD4755 Approved
0.5692 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5692 Remote Similarity NPD6317 Approved
0.5691 Remote Similarity NPD5141 Approved
0.569 Remote Similarity NPD8034 Phase 2
0.569 Remote Similarity NPD8035 Phase 2
0.5683 Remote Similarity NPD6845 Suspended
0.5678 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5676 Remote Similarity NPD4788 Approved
0.5672 Remote Similarity NPD8328 Phase 3
0.5672 Remote Similarity NPD7829 Approved
0.5672 Remote Similarity NPD7830 Approved
0.5656 Remote Similarity NPD4633 Approved
0.5656 Remote Similarity NPD5226 Approved
0.5656 Remote Similarity NPD5224 Approved
0.5656 Remote Similarity NPD5225 Approved
0.5652 Remote Similarity NPD6673 Approved
0.5652 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5652 Remote Similarity NPD6080 Approved
0.5652 Remote Similarity NPD6101 Approved
0.5652 Remote Similarity NPD6904 Approved
0.5649 Remote Similarity NPD6314 Approved
0.5649 Remote Similarity NPD6335 Approved
0.5649 Remote Similarity NPD6313 Approved
0.5648 Remote Similarity NPD5784 Clinical (unspecified phase)
0.562 Remote Similarity NPD4700 Approved
0.5614 Remote Similarity NPD7524 Approved
0.5612 Remote Similarity NPD7260 Phase 2
0.561 Remote Similarity NPD5175 Approved
0.561 Remote Similarity NPD5174 Approved
0.5603 Remote Similarity NPD5692 Phase 3

Structure

External Identifiers

PubChem CID   14466529
ChEMBL   CHEMBL485807
ZINC  

Physicochemical Properties

Molecular Weight:  362.14
ALogP:  -0.5137
MLogP:  2.78
XLogP:  -0.542
# Rotatable Bonds:  5
Polar Surface Area:  97.89
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  26

Download Data

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