Natural Product: NPC470243

Natural Product ID:  NPC470243
Common Name:   Dihydroergolide
IUPAC Name:   [(1R,3aS,5R,5aS,8aR,9S,9aR)-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,6,7,9,9a-octahydro-1H-azuleno[6,5-b]furan-9-yl] acetate
Synonyms:   Dihydroergolide
Molecular Formula:   C17H24O5
Standard InCHIKey:  SLDGZDXXRTZQAQ-WUYYVTOLSA-N
Standard InCHI:  InChI=1S/C17H24O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h8-9,11-12,14-15H,5-7H2,1-4H3/t8-,9-,11+,12+,14-,15+,17+/m1/s1
Canonical SMILES:  CC(=O)O[C@H]1[C@H]2[C@@H](OC(=O)[C@@H]2C)C[C@H]([C@H]2[C@@]1(C)C(=O)CC2)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
NPO22238 Inula falconeri Species Asteraceae Eukaryota Aerial parts Tibet, China PMID[21924800]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 8340 nM 20825224

  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 NPC470243 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
0.9286 High Similarity NPC179922
0.9091 High Similarity NPC157518
0.825 Intermediate Similarity NPC238593
0.8108 Intermediate Similarity NPC215030
0.7875 Intermediate Similarity NPC54468
0.7867 Intermediate Similarity NPC477867
0.7805 Intermediate Similarity NPC70422
0.7805 Intermediate Similarity NPC70555
0.7805 Intermediate Similarity NPC104961
0.7765 Intermediate Similarity NPC191339
0.7765 Intermediate Similarity NPC286341
0.7746 Intermediate Similarity NPC215987
0.7746 Intermediate Similarity NPC306805
0.7738 Intermediate Similarity NPC168679
0.7738 Intermediate Similarity NPC12872
0.7733 Intermediate Similarity NPC474755
0.7722 Intermediate Similarity NPC51507
0.7722 Intermediate Similarity NPC1882
0.7671 Intermediate Similarity NPC119838
0.75 Intermediate Similarity NPC73052
0.75 Intermediate Similarity NPC290508
0.75 Intermediate Similarity NPC6823
0.75 Intermediate Similarity NPC293418
0.75 Intermediate Similarity NPC476330
0.7442 Intermediate Similarity NPC253144
0.7439 Intermediate Similarity NPC157328
0.7416 Intermediate Similarity NPC126156
0.7416 Intermediate Similarity NPC91771
0.7416 Intermediate Similarity NPC142529
0.7412 Intermediate Similarity NPC53158
0.7375 Intermediate Similarity NPC474754
0.7361 Intermediate Similarity NPC314103
0.7356 Intermediate Similarity NPC284185
0.7356 Intermediate Similarity NPC70595
0.7356 Intermediate Similarity NPC74103
0.7356 Intermediate Similarity NPC123177
0.7356 Intermediate Similarity NPC150978
0.7342 Intermediate Similarity NPC471151
0.7333 Intermediate Similarity NPC5714
0.7326 Intermediate Similarity NPC117405
0.7326 Intermediate Similarity NPC200580
0.7326 Intermediate Similarity NPC52198
0.7317 Intermediate Similarity NPC212340
0.7317 Intermediate Similarity NPC13494
0.7294 Intermediate Similarity NPC201658
0.7273 Intermediate Similarity NPC473273
0.7273 Intermediate Similarity NPC308656
0.7273 Intermediate Similarity NPC153590
0.7273 Intermediate Similarity NPC473263
0.7273 Intermediate Similarity NPC473234
0.7273 Intermediate Similarity NPC60386
0.7273 Intermediate Similarity NPC248567
0.7262 Intermediate Similarity NPC473350
0.726 Intermediate Similarity NPC295256
0.726 Intermediate Similarity NPC469926
0.7215 Intermediate Similarity NPC471046
0.72 Intermediate Similarity NPC319007
0.7191 Intermediate Similarity NPC289004
0.7183 Intermediate Similarity NPC472021
0.7176 Intermediate Similarity NPC236692
0.7176 Intermediate Similarity NPC304558
0.7176 Intermediate Similarity NPC309757
0.7162 Intermediate Similarity NPC315525
0.7162 Intermediate Similarity NPC135043
0.7143 Intermediate Similarity NPC25802
0.7143 Intermediate Similarity NPC51135
0.7143 Intermediate Similarity NPC82492
0.7143 Intermediate Similarity NPC101138
0.7125 Intermediate Similarity NPC477918
0.7125 Intermediate Similarity NPC169389
0.7125 Intermediate Similarity NPC208223
0.7097 Intermediate Similarity NPC171759
0.7093 Intermediate Similarity NPC24728
0.7089 Intermediate Similarity NPC471491
0.7083 Intermediate Similarity NPC469922
0.7079 Intermediate Similarity NPC472238
0.7079 Intermediate Similarity NPC472237
0.7079 Intermediate Similarity NPC200237
0.7073 Intermediate Similarity NPC134227
0.7067 Intermediate Similarity NPC469925
0.7059 Intermediate Similarity NPC319589
0.7051 Intermediate Similarity NPC109510
0.7042 Intermediate Similarity NPC472019
0.7042 Intermediate Similarity NPC226602
0.7042 Intermediate Similarity NPC472020
0.7033 Intermediate Similarity NPC185553
0.7033 Intermediate Similarity NPC193785
0.7024 Intermediate Similarity NPC476721
0.7024 Intermediate Similarity NPC472847
0.7011 Intermediate Similarity NPC470009
0.7011 Intermediate Similarity NPC471149
0.7 Intermediate Similarity NPC470424
0.7 Intermediate Similarity NPC473331
0.6988 Remote Similarity NPC39411
0.6988 Remote Similarity NPC255580
0.6977 Remote Similarity NPC476717
0.6977 Remote Similarity NPC477441
0.697 Remote Similarity NPC305182
0.6962 Remote Similarity NPC469641
0.6962 Remote Similarity NPC469643
0.6957 Remote Similarity NPC108475
0.6957 Remote Similarity NPC213947
0.6957 Remote Similarity NPC170143
0.6957 Remote Similarity NPC169205
0.6947 Remote Similarity NPC469350
0.6941 Remote Similarity NPC65133
0.6941 Remote Similarity NPC477434
0.6932 Remote Similarity NPC283409
0.6923 Remote Similarity NPC90121
0.6923 Remote Similarity NPC197701
0.6923 Remote Similarity NPC193645
0.6923 Remote Similarity NPC275960
0.6923 Remote Similarity NPC48803
0.6915 Remote Similarity NPC162024
0.6915 Remote Similarity NPC477950
0.6914 Remote Similarity NPC143250
0.6905 Remote Similarity NPC246076
0.6897 Remote Similarity NPC118601
0.6889 Remote Similarity NPC228700
0.6889 Remote Similarity NPC476189
0.6882 Remote Similarity NPC141191
0.6882 Remote Similarity NPC54843
0.6882 Remote Similarity NPC274695
0.6875 Remote Similarity NPC132064
0.6875 Remote Similarity NPC477934
0.6867 Remote Similarity NPC125366
0.6866 Remote Similarity NPC314084
0.6854 Remote Similarity NPC54065
0.6854 Remote Similarity NPC297474
0.6854 Remote Similarity NPC19087
0.6849 Remote Similarity NPC306750
0.6849 Remote Similarity NPC253204
0.6835 Remote Similarity NPC475232
0.6835 Remote Similarity NPC473775
0.6835 Remote Similarity NPC475260
0.6835 Remote Similarity NPC473699
0.6835 Remote Similarity NPC474100
0.6835 Remote Similarity NPC51249
0.6824 Remote Similarity NPC128246
0.6824 Remote Similarity NPC111409
0.6824 Remote Similarity NPC215294
0.6818 Remote Similarity NPC178875
0.6813 Remote Similarity NPC206878
0.6804 Remote Similarity NPC228311
0.6804 Remote Similarity NPC291643
0.6804 Remote Similarity NPC168890
0.6804 Remote Similarity NPC469441
0.6804 Remote Similarity NPC41674
0.679 Remote Similarity NPC477933
0.679 Remote Similarity NPC477932
0.6786 Remote Similarity NPC475951
0.6782 Remote Similarity NPC243746
0.6782 Remote Similarity NPC92139
0.6782 Remote Similarity NPC475491
0.6782 Remote Similarity NPC469626
0.6778 Remote Similarity NPC133888
0.6778 Remote Similarity NPC57304
0.6778 Remote Similarity NPC35959
0.6778 Remote Similarity NPC29821
0.6778 Remote Similarity NPC216137
0.6778 Remote Similarity NPC184063
0.6778 Remote Similarity NPC293001
0.6778 Remote Similarity NPC171360
0.6778 Remote Similarity NPC63193
0.6774 Remote Similarity NPC311904
0.6757 Remote Similarity NPC474552
0.675 Remote Similarity NPC320537
0.675 Remote Similarity NPC143979
0.675 Remote Similarity NPC125164
0.675 Remote Similarity NPC55508
0.6747 Remote Similarity NPC469620
0.6744 Remote Similarity NPC319909
0.6742 Remote Similarity NPC477443
0.6742 Remote Similarity NPC61688
0.6742 Remote Similarity NPC67653
0.6742 Remote Similarity NPC471459
0.6742 Remote Similarity NPC155935
0.6742 Remote Similarity NPC38392
0.6742 Remote Similarity NPC477440
0.6739 Remote Similarity NPC470191
0.6739 Remote Similarity NPC287354
0.6739 Remote Similarity NPC62407
0.6739 Remote Similarity NPC163228
0.6737 Remote Similarity NPC304624
0.6737 Remote Similarity NPC474053
0.6735 Remote Similarity NPC290247
0.6735 Remote Similarity NPC469788
0.6735 Remote Similarity NPC176756
0.6735 Remote Similarity NPC469787
0.6712 Remote Similarity NPC478126
0.6712 Remote Similarity NPC469921
0.6712 Remote Similarity NPC66145
0.6709 Remote Similarity NPC96322
0.6707 Remote Similarity NPC307865
0.6707 Remote Similarity NPC474003
0.6707 Remote Similarity NPC214030
0.6707 Remote Similarity NPC83108
0.6706 Remote Similarity NPC148740
0.6706 Remote Similarity NPC102156
0.6705 Remote Similarity NPC475773

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC470243 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
0.7671 Intermediate Similarity NPD229 Approved
0.726 Intermediate Similarity NPD9496 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5777 Approved
0.6923 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6829 Remote Similarity NPD4238 Approved
0.6829 Remote Similarity NPD4802 Phase 2
0.6575 Remote Similarity NPD3198 Approved
0.6512 Remote Similarity NPD6435 Approved
0.6463 Remote Similarity NPD3702 Approved
0.6392 Remote Similarity NPD1700 Approved
0.6364 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6338 Remote Similarity NPD3729 Clinical (unspecified phase)
0.631 Remote Similarity NPD6116 Phase 1
0.6279 Remote Similarity NPD5368 Approved
0.6222 Remote Similarity NPD5786 Approved
0.6207 Remote Similarity NPD5369 Approved
0.619 Remote Similarity NPD6117 Approved
0.6154 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6145 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6098 Remote Similarity NPD6081 Approved
0.6076 Remote Similarity NPD4224 Phase 2
0.6071 Remote Similarity NPD3703 Phase 2
0.6049 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6049 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6049 Remote Similarity NPD3698 Phase 2
0.6047 Remote Similarity NPD6114 Approved
0.6047 Remote Similarity NPD6115 Approved
0.6047 Remote Similarity NPD6697 Approved
0.6047 Remote Similarity NPD6118 Approved
0.6026 Remote Similarity NPD7909 Approved
0.6022 Remote Similarity NPD1695 Approved
0.6 Remote Similarity NPD6399 Phase 3
0.598 Remote Similarity NPD6008 Approved
0.5976 Remote Similarity NPD4245 Approved
0.5976 Remote Similarity NPD4244 Approved
0.597 Remote Similarity NPD2699 Approved
0.5957 Remote Similarity NPD5785 Approved
0.5955 Remote Similarity NPD4269 Approved
0.5955 Remote Similarity NPD4270 Approved
0.5942 Remote Similarity NPD2266 Phase 2
0.5942 Remote Similarity NPD6125 Clinical (unspecified phase)
0.5938 Remote Similarity NPD5282 Discontinued
0.5914 Remote Similarity NPD6903 Approved
0.5909 Remote Similarity NPD387 Clinical (unspecified phase)
0.5904 Remote Similarity NPD4809 Clinical (unspecified phase)
0.5904 Remote Similarity NPD4808 Clinical (unspecified phase)
0.5895 Remote Similarity NPD6411 Approved
0.5895 Remote Similarity NPD8034 Phase 2
0.5895 Remote Similarity NPD8035 Phase 2
0.589 Remote Similarity NPD615 Clinical (unspecified phase)
0.587 Remote Similarity NPD7334 Approved
0.587 Remote Similarity NPD6684 Approved
0.587 Remote Similarity NPD5330 Approved
0.587 Remote Similarity NPD7146 Approved
0.587 Remote Similarity NPD6409 Approved
0.587 Remote Similarity NPD7521 Approved
0.5862 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5797 Remote Similarity NPD344 Approved
0.5797 Remote Similarity NPD343 Approved
0.5797 Remote Similarity NPD345 Approved
0.5783 Remote Similarity NPD4789 Approved
0.5778 Remote Similarity NPD7345 Approved
0.5769 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5761 Remote Similarity NPD1694 Approved
0.5761 Remote Similarity NPD5363 Approved
0.5745 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5745 Remote Similarity NPD6672 Approved
0.5745 Remote Similarity NPD5737 Approved
0.573 Remote Similarity NPD4252 Approved
0.5728 Remote Similarity NPD8170 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7320 Approved
0.5714 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5694 Remote Similarity NPD9638 Phase 2
0.5684 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5684 Remote Similarity NPD6101 Approved
0.5676 Remote Similarity NPD3728 Approved
0.5676 Remote Similarity NPD3730 Approved
0.5673 Remote Similarity NPD7128 Approved
0.5673 Remote Similarity NPD6402 Approved
0.5673 Remote Similarity NPD6675 Approved
0.5673 Remote Similarity NPD5739 Approved
0.5667 Remote Similarity NPD1780 Approved
0.5667 Remote Similarity NPD1779 Approved
0.5663 Remote Similarity NPD3726 Approved
0.5663 Remote Similarity NPD3725 Approved
0.566 Remote Similarity NPD6372 Approved
0.566 Remote Similarity NPD6373 Approved
0.5652 Remote Similarity NPD634 Phase 3
0.5625 Remote Similarity NPD5207 Approved
0.5619 Remote Similarity NPD5697 Approved
0.5619 Remote Similarity NPD5701 Approved
0.5607 Remote Similarity NPD6371 Approved

Structure

External Identifiers

PubChem CID   57403344
ChEMBL   CHEMBL1912045
ZINC  

Physicochemical Properties

Molecular Weight:  308.16
ALogP:  0.3691
MLogP:  2.78
XLogP:  1.591
# Rotatable Bonds:  6
Polar Surface Area:  69.67
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  22

Download Data

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Similar NPs/Drugs