Natural Product: NPC470569

Natural Product ID:  NPC470569
Common Name:   (-)-6-O-Methylaverantin
IUPAC Name:   1,3,8-trihydroxy-2-[(1S)-1-hydroxyhexyl]-6-methoxyanthracene-9,10-dione
Synonyms:  
Molecular Formula:   C21H22O7
Standard InCHIKey:  ZWFWVRGWGWHKBK-ZDUSSCGKSA-N
Standard InCHI:  InChI=1S/C21H22O7/c1-3-4-5-6-13(22)18-15(24)9-12-17(21(18)27)20(26)16-11(19(12)25)7-10(28-2)8-14(16)23/h7-9,13,22-24,27H,3-6H2,1-2H3/t13-/m0/s1
Canonical SMILES:  CCCCC[C@@H](c1c(O)cc2c(c1O)C(=O)c1c(C2=O)cc(cc1O)OC)O
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
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota PMID[22703109]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT397 Cell Line NCI-H460 Homo sapiens IC50 > 50000 nM 26636180
NPT83 Cell Line MCF7 Homo sapiens IC50 > 50000 nM 18547115
NPT395 Cell Line SF-268 Homo sapiens IC50 > 50000 nM 12762821

  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 NPC470569 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
0.9931 High Similarity NPC470568
0.9793 High Similarity NPC147735
0.9793 High Similarity NPC290954
0.9793 High Similarity NPC255641
0.9722 High Similarity NPC245584
0.9722 High Similarity NPC190648
0.9722 High Similarity NPC118027
0.9722 High Similarity NPC289042
0.9722 High Similarity NPC56433
0.9722 High Similarity NPC312929
0.9722 High Similarity NPC126767
0.966 High Similarity NPC154683
0.966 High Similarity NPC40356
0.9583 High Similarity NPC34482
0.9524 High Similarity NPC294646
0.9517 High Similarity NPC470570
0.9514 High Similarity NPC48762
0.9514 High Similarity NPC19896
0.947 High Similarity NPC324736
0.9463 High Similarity NPC208806
0.9452 High Similarity NPC34802
0.9448 High Similarity NPC49282
0.9444 High Similarity NPC167663
0.94 High Similarity NPC226656
0.94 High Similarity NPC66508
0.9379 High Similarity NPC21599
0.9379 High Similarity NPC193703
0.9375 High Similarity NPC135524
0.9333 High Similarity NPC107109
0.9329 High Similarity NPC132990
0.9329 High Similarity NPC474417
0.9329 High Similarity NPC478148
0.9329 High Similarity NPC149526
0.9329 High Similarity NPC72958
0.9329 High Similarity NPC46882
0.9329 High Similarity NPC232645
0.9324 High Similarity NPC329933
0.9315 High Similarity NPC478019
0.931 High Similarity NPC84266
0.9306 High Similarity NPC204045
0.9306 High Similarity NPC305845
0.9276 High Similarity NPC37543
0.9276 High Similarity NPC199463
0.9267 High Similarity NPC268992
0.9267 High Similarity NPC87708
0.9267 High Similarity NPC113608
0.9267 High Similarity NPC470337
0.9267 High Similarity NPC51824
0.9267 High Similarity NPC180944
0.9267 High Similarity NPC470338
0.9267 High Similarity NPC470340
0.9262 High Similarity NPC202595
0.9257 High Similarity NPC2569
0.9257 High Similarity NPC172329
0.9241 High Similarity NPC94076
0.9241 High Similarity NPC182255
0.9241 High Similarity NPC49108
0.9211 High Similarity NPC14561
0.9211 High Similarity NPC77807
0.9211 High Similarity NPC5379
0.9205 High Similarity NPC155686
0.9205 High Similarity NPC93552
0.9205 High Similarity NPC214632
0.9195 High Similarity NPC97028
0.9195 High Similarity NPC288036
0.9195 High Similarity NPC158338
0.9195 High Similarity NPC65589
0.9195 High Similarity NPC97029
0.9195 High Similarity NPC100985
0.9178 High Similarity NPC3732
0.9172 High Similarity NPC470341
0.9172 High Similarity NPC472058
0.9172 High Similarity NPC234497
0.9172 High Similarity NPC253822
0.9172 High Similarity NPC324522
0.9172 High Similarity NPC105414
0.9156 High Similarity NPC472052
0.9156 High Similarity NPC472060
0.9156 High Similarity NPC470342
0.9156 High Similarity NPC470810
0.9156 High Similarity NPC284495
0.915 High Similarity NPC263483
0.915 High Similarity NPC178976
0.9145 High Similarity NPC68727
0.9133 High Similarity NPC225854
0.9128 High Similarity NPC472056
0.9128 High Similarity NPC27221
0.9128 High Similarity NPC256672
0.9128 High Similarity NPC7025
0.9122 High Similarity NPC300540
0.9122 High Similarity NPC163846
0.9122 High Similarity NPC225173
0.9116 High Similarity NPC471906
0.9116 High Similarity NPC475705
0.9116 High Similarity NPC476178
0.9116 High Similarity NPC51887
0.9116 High Similarity NPC244691
0.9116 High Similarity NPC475201
0.9116 High Similarity NPC117836
0.911 High Similarity NPC55832
0.911 High Similarity NPC470087
0.911 High Similarity NPC268204
0.911 High Similarity NPC52789
0.911 High Similarity NPC321980
0.911 High Similarity NPC474961
0.911 High Similarity NPC26051
0.9108 High Similarity NPC477835
0.9103 High Similarity NPC100849
0.9103 High Similarity NPC472366
0.9103 High Similarity NPC470211
0.9079 High Similarity NPC329844
0.9079 High Similarity NPC169990
0.9079 High Similarity NPC210942
0.9079 High Similarity NPC135522
0.9073 High Similarity NPC230848
0.9067 High Similarity NPC65775
0.9067 High Similarity NPC80370
0.9067 High Similarity NPC10027
0.906 High Similarity NPC7943
0.906 High Similarity NPC123202
0.906 High Similarity NPC125801
0.906 High Similarity NPC22005
0.9054 High Similarity NPC476055
0.9054 High Similarity NPC28632
0.9048 High Similarity NPC277369
0.9048 High Similarity NPC215451
0.9045 High Similarity NPC472051
0.9045 High Similarity NPC472057
0.9041 High Similarity NPC259166
0.9041 High Similarity NPC204985
0.9041 High Similarity NPC172250
0.9041 High Similarity NPC48624
0.9041 High Similarity NPC213659
0.9041 High Similarity NPC326109
0.9041 High Similarity NPC215311
0.9041 High Similarity NPC144118
0.9041 High Similarity NPC80962
0.9041 High Similarity NPC101366
0.9041 High Similarity NPC219917
0.9034 High Similarity NPC190457
0.9034 High Similarity NPC242994
0.9034 High Similarity NPC1268
0.9034 High Similarity NPC138099
0.9032 High Similarity NPC84571
0.9028 High Similarity NPC471905
0.9026 High Similarity NPC474637
0.9026 High Similarity NPC201127
0.9013 High Similarity NPC273483
0.9013 High Similarity NPC474843
0.9007 High Similarity NPC474660
0.9007 High Similarity NPC280295
0.9 High Similarity NPC111536
0.9 High Similarity NPC271385
0.9 High Similarity NPC76128
0.9 High Similarity NPC30432
0.9 High Similarity NPC5029
0.8994 High Similarity NPC470567
0.8993 High Similarity NPC24136
0.8993 High Similarity NPC469758
0.8993 High Similarity NPC290133
0.8993 High Similarity NPC187282
0.8986 High Similarity NPC245482
0.8986 High Similarity NPC301751
0.898 High Similarity NPC126534
0.898 High Similarity NPC469404
0.898 High Similarity NPC40118
0.898 High Similarity NPC470089
0.898 High Similarity NPC232021
0.8974 High Similarity NPC311740
0.8973 High Similarity NPC109232
0.8973 High Similarity NPC477956
0.8973 High Similarity NPC295384
0.8973 High Similarity NPC283429
0.8973 High Similarity NPC181560
0.8973 High Similarity NPC169452
0.8968 High Similarity NPC470339
0.8968 High Similarity NPC85121
0.8968 High Similarity NPC186113
0.8966 High Similarity NPC472419
0.8961 High Similarity NPC472050
0.8961 High Similarity NPC146211
0.8961 High Similarity NPC180924
0.8958 High Similarity NPC254847
0.8954 High Similarity NPC193200
0.8947 High Similarity NPC476553
0.8947 High Similarity NPC258249
0.8947 High Similarity NPC476551
0.8947 High Similarity NPC476552
0.8944 High Similarity NPC98776
0.8944 High Similarity NPC472054
0.894 High Similarity NPC291049
0.894 High Similarity NPC233267
0.8933 High Similarity NPC51070
0.8933 High Similarity NPC71055
0.8933 High Similarity NPC222298
0.8931 High Similarity NPC470566
0.8926 High Similarity NPC470890
0.8926 High Similarity NPC469764
0.8926 High Similarity NPC224714
0.8924 High Similarity NPC316262

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC470569 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
0.8958 High Similarity NPD1509 Clinical (unspecified phase)
0.8854 High Similarity NPD6959 Discontinued
0.8797 High Similarity NPD6232 Discontinued
0.875 High Similarity NPD7473 Discontinued
0.871 High Similarity NPD7819 Suspended
0.8699 High Similarity NPD1510 Phase 2
0.869 High Similarity NPD1607 Approved
0.8675 High Similarity NPD2534 Approved
0.8675 High Similarity NPD2533 Approved
0.8675 High Similarity NPD2532 Approved
0.8636 High Similarity NPD4380 Phase 2
0.859 High Similarity NPD2393 Clinical (unspecified phase)
0.8553 High Similarity NPD4378 Clinical (unspecified phase)
0.8552 High Similarity NPD1240 Approved
0.8535 High Similarity NPD8443 Clinical (unspecified phase)
0.8523 High Similarity NPD1549 Phase 2
0.8456 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8456 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8431 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.84 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8389 Intermediate Similarity NPD2796 Approved
0.8366 Intermediate Similarity NPD7390 Discontinued
0.8344 Intermediate Similarity NPD7411 Suspended
0.8333 Intermediate Similarity NPD3226 Approved
0.8313 Intermediate Similarity NPD7075 Discontinued
0.8303 Intermediate Similarity NPD5844 Phase 1
0.8291 Intermediate Similarity NPD1934 Approved
0.8239 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD6801 Discontinued
0.815 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8146 Intermediate Similarity NPD2935 Discontinued
0.8137 Intermediate Similarity NPD7768 Phase 2
0.8137 Intermediate Similarity NPD3882 Suspended
0.8125 Intermediate Similarity NPD2801 Approved
0.8121 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD6166 Phase 2
0.8098 Intermediate Similarity NPD5494 Approved
0.8086 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8086 Intermediate Similarity NPD3749 Approved
0.8069 Intermediate Similarity NPD1470 Approved
0.8052 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8052 Intermediate Similarity NPD3750 Approved
0.805 Intermediate Similarity NPD6599 Discontinued
0.8047 Intermediate Similarity NPD6559 Discontinued
0.8025 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8024 Intermediate Similarity NPD3818 Discontinued
0.8013 Intermediate Similarity NPD1511 Approved
0.8 Intermediate Similarity NPD5710 Approved
0.8 Intermediate Similarity NPD5711 Approved
0.7987 Intermediate Similarity NPD2800 Approved
0.7987 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7974 Intermediate Similarity NPD2346 Discontinued
0.7947 Intermediate Similarity NPD6651 Approved
0.7911 Intermediate Similarity NPD1512 Approved
0.7908 Intermediate Similarity NPD6099 Approved
0.7908 Intermediate Similarity NPD5404 Approved
0.7908 Intermediate Similarity NPD5406 Approved
0.7908 Intermediate Similarity NPD1551 Phase 2
0.7908 Intermediate Similarity NPD6100 Approved
0.7908 Intermediate Similarity NPD5408 Approved
0.7908 Intermediate Similarity NPD5405 Approved
0.7898 Intermediate Similarity NPD6799 Approved
0.7875 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.784 Intermediate Similarity NPD37 Approved
0.7833 Intermediate Similarity NPD6781 Approved
0.7833 Intermediate Similarity NPD6778 Approved
0.7833 Intermediate Similarity NPD6782 Approved
0.7833 Intermediate Similarity NPD6776 Approved
0.7833 Intermediate Similarity NPD6777 Approved
0.7833 Intermediate Similarity NPD6780 Approved
0.7833 Intermediate Similarity NPD6779 Approved
0.7824 Intermediate Similarity NPD7074 Phase 3
0.7821 Intermediate Similarity NPD4628 Phase 3
0.7815 Intermediate Similarity NPD943 Approved
0.7793 Intermediate Similarity NPD1201 Approved
0.7784 Intermediate Similarity NPD8151 Discontinued
0.7778 Intermediate Similarity NPD5953 Discontinued
0.7765 Intermediate Similarity NPD7054 Approved
0.7746 Intermediate Similarity NPD8312 Approved
0.7746 Intermediate Similarity NPD8313 Approved
0.7744 Intermediate Similarity NPD5402 Approved
0.7744 Intermediate Similarity NPD3817 Phase 2
0.7742 Intermediate Similarity NPD2344 Approved
0.7727 Intermediate Similarity NPD2799 Discontinued
0.7727 Intermediate Similarity NPD3748 Approved
0.7727 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD7472 Approved
0.7707 Intermediate Similarity NPD7003 Approved
0.7707 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7705 Intermediate Similarity NPD7698 Approved
0.7705 Intermediate Similarity NPD7696 Phase 3
0.7705 Intermediate Similarity NPD7435 Discontinued
0.7705 Intermediate Similarity NPD7697 Approved
0.7697 Intermediate Similarity NPD4967 Phase 2
0.7697 Intermediate Similarity NPD4965 Approved
0.7697 Intermediate Similarity NPD4966 Approved
0.7688 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD6797 Phase 2
0.7674 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7663 Intermediate Similarity NPD7871 Phase 2
0.7663 Intermediate Similarity NPD7870 Phase 2
0.7654 Intermediate Similarity NPD7458 Discontinued
0.7643 Intermediate Similarity NPD1243 Approved
0.764 Intermediate Similarity NPD5403 Approved
0.764 Intermediate Similarity NPD920 Approved
0.763 Intermediate Similarity NPD7251 Discontinued
0.7625 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD4625 Phase 3
0.7614 Intermediate Similarity NPD8150 Discontinued
0.7605 Intermediate Similarity NPD6234 Discontinued
0.7602 Intermediate Similarity NPD3751 Discontinued
0.7586 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD7808 Phase 3
0.7576 Intermediate Similarity NPD1465 Phase 2
0.7566 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7566 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD7286 Phase 2
0.7556 Intermediate Similarity NPD6534 Approved
0.7556 Intermediate Similarity NPD6535 Approved
0.7547 Intermediate Similarity NPD2309 Approved
0.754 Intermediate Similarity NPD7701 Phase 2
0.7533 Intermediate Similarity NPD2798 Approved
0.7531 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD3926 Phase 2
0.7516 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD5401 Approved
0.75 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3972 Approved
0.75 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD7229 Phase 3
0.7469 Intermediate Similarity NPD6273 Approved
0.7466 Intermediate Similarity NPD1651 Approved
0.746 Intermediate Similarity NPD7874 Approved
0.746 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD6823 Phase 2
0.7451 Intermediate Similarity NPD3764 Approved
0.7451 Intermediate Similarity NPD2313 Discontinued
0.7446 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD4908 Phase 1
0.7432 Intermediate Similarity NPD7700 Phase 2
0.7432 Intermediate Similarity NPD7699 Phase 2
0.7421 Intermediate Similarity NPD7801 Approved
0.7419 Intermediate Similarity NPD230 Phase 1
0.7417 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD1247 Approved
0.7405 Intermediate Similarity NPD1471 Phase 3
0.74 Intermediate Similarity NPD1283 Approved
0.7399 Intermediate Similarity NPD7177 Discontinued
0.7399 Intermediate Similarity NPD7228 Approved
0.7396 Intermediate Similarity NPD919 Approved
0.7368 Intermediate Similarity NPD3787 Discontinued
0.7365 Intermediate Similarity NPD5761 Phase 2
0.7365 Intermediate Similarity NPD5760 Phase 2
0.7363 Intermediate Similarity NPD4363 Phase 3
0.7363 Intermediate Similarity NPD4360 Phase 2
0.7338 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD8434 Phase 2
0.7315 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD2654 Approved
0.731 Intermediate Similarity NPD7199 Phase 2
0.7308 Intermediate Similarity NPD6212 Phase 3
0.7308 Intermediate Similarity NPD6213 Phase 3
0.7308 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD4626 Approved
0.7287 Intermediate Similarity NPD8320 Phase 1
0.7287 Intermediate Similarity NPD8319 Approved
0.7285 Intermediate Similarity NPD1876 Approved
0.7283 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD7033 Discontinued
0.7273 Intermediate Similarity NPD3027 Phase 3
0.7263 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD7783 Phase 2
0.7237 Intermediate Similarity NPD1203 Approved
0.7228 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD4361 Phase 2
0.7219 Intermediate Similarity NPD4749 Approved
0.7208 Intermediate Similarity NPD6832 Phase 2
0.7205 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD1281 Approved
0.72 Intermediate Similarity NPD1610 Phase 2
0.717 Intermediate Similarity NPD4308 Phase 3
0.7143 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4287 Approved
0.7135 Intermediate Similarity NPD3658 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD1613 Approved
0.7134 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD2979 Phase 3
0.7126 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD2438 Suspended
0.7124 Intermediate Similarity NPD1164 Approved
0.7118 Intermediate Similarity NPD4288 Approved
0.7117 Intermediate Similarity NPD6190 Approved

Structure

External Identifiers

PubChem CID   70684688
ChEMBL   CHEMBL2071290
ZINC  

Physicochemical Properties

Molecular Weight:  386.14
ALogP:  -3.5717
MLogP:  3
XLogP:  2.26
# Rotatable Bonds:  12
Polar Surface Area:  124.29
# H-Bond Aceptor:  3
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  28

Download Data

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