Natural Product: NPC242994

Natural Product ID:  NPC242994
Common Name:   Lupinacidin B
IUPAC Name:   4-butyl-1,3,5-trihydroxy-2-methylanthracene-9,10-dione
Synonyms:   Lupinacidins B
Molecular Formula:   C19H18O5
Standard InCHIKey:  IVQKRDHUECCAJE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H18O5/c1-3-4-6-11-14-15(17(22)9(2)16(11)21)18(23)10-7-5-8-12(20)13(10)19(14)24/h5,7-8,20-22H,3-4,6H2,1-2H3
Canonical SMILES:  CCCCc1c2c(C(=O)c3c(C2=O)c(O)ccc3)c(c(c1O)C)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
NPO24286 Micromonospora lupini Species Micromonosporaceae Bacteria PMID[17475486]
NPO24286 Micromonospora lupini Species Micromonosporaceae Bacteria PMID[21226490]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 = 920 nM DrugMatrix in vitro pharmacology data
NPT2 Others Unspecified IC50 = 920 nM 18183025

  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 NPC242994 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
1.0 High Similarity NPC138099
0.9925 High Similarity NPC181560
0.9925 High Similarity NPC169452
0.9848 High Similarity NPC471905
0.9848 High Similarity NPC53206
0.9848 High Similarity NPC53414
0.9778 High Similarity NPC193555
0.9773 High Similarity NPC254847
0.9632 High Similarity NPC135524
0.9624 High Similarity NPC191976
0.9621 High Similarity NPC166480
0.9621 High Similarity NPC44437
0.9621 High Similarity NPC282780
0.9559 High Similarity NPC246638
0.9559 High Similarity NPC204045
0.9559 High Similarity NPC305845
0.9556 High Similarity NPC143438
0.9545 High Similarity NPC267205
0.9493 High Similarity NPC21599
0.9493 High Similarity NPC193703
0.9424 High Similarity NPC34482
0.9412 High Similarity NPC190457
0.9357 High Similarity NPC470570
0.9353 High Similarity NPC471906
0.9353 High Similarity NPC48762
0.9353 High Similarity NPC244691
0.9348 High Similarity NPC73061
0.9348 High Similarity NPC474961
0.9333 High Similarity NPC118919
0.9291 High Similarity NPC37709
0.9281 High Similarity NPC313047
0.9281 High Similarity NPC451542
0.9281 High Similarity NPC295712
0.9281 High Similarity NPC474203
0.9275 High Similarity NPC290550
0.9259 High Similarity NPC283088
0.9242 High Similarity NPC92624
0.9242 High Similarity NPC99731
0.9203 High Similarity NPC203063
0.9197 High Similarity NPC4214
0.9197 High Similarity NPC13715
0.9179 High Similarity NPC175738
0.9173 High Similarity NPC259942
0.9167 High Similarity NPC282923
0.9155 High Similarity NPC118027
0.9155 High Similarity NPC190648
0.9155 High Similarity NPC126767
0.9155 High Similarity NPC245584
0.9155 High Similarity NPC56433
0.9155 High Similarity NPC312929
0.9155 High Similarity NPC289042
0.9143 High Similarity NPC174905
0.9143 High Similarity NPC293545
0.9137 High Similarity NPC187843
0.9124 High Similarity NPC53001
0.9118 High Similarity NPC161632
0.9111 High Similarity NPC115458
0.9098 High Similarity NPC474998
0.9098 High Similarity NPC109123
0.9097 High Similarity NPC470568
0.9097 High Similarity NPC255641
0.9097 High Similarity NPC290954
0.9091 High Similarity NPC105157
0.9091 High Similarity NPC162612
0.9091 High Similarity NPC30501
0.9091 High Similarity NPC103356
0.9091 High Similarity NPC72158
0.9091 High Similarity NPC266689
0.9091 High Similarity NPC169250
0.9091 High Similarity NPC100067
0.9091 High Similarity NPC190043
0.9091 High Similarity NPC98254
0.9091 High Similarity NPC23126
0.9085 High Similarity NPC271944
0.9085 High Similarity NPC110882
0.9085 High Similarity NPC85393
0.9078 High Similarity NPC10764
0.9078 High Similarity NPC227841
0.9071 High Similarity NPC19631
0.9071 High Similarity NPC239136
0.9058 High Similarity NPC61398
0.9058 High Similarity NPC87723
0.9058 High Similarity NPC416
0.9044 High Similarity NPC12070
0.9044 High Similarity NPC50924
0.9034 High Similarity NPC470569
0.9023 High Similarity NPC221777
0.9023 High Similarity NPC48248
0.9023 High Similarity NPC473017
0.9023 High Similarity NPC21305
0.9015 High Similarity NPC8745
0.9015 High Similarity NPC62952
0.9015 High Similarity NPC267846
0.9014 High Similarity NPC12402
0.9007 High Similarity NPC471682
0.9007 High Similarity NPC238629
0.9007 High Similarity NPC296752
0.8993 High Similarity NPC162939
0.8986 High Similarity NPC290030
0.898 High Similarity NPC226656
0.898 High Similarity NPC66508
0.8978 High Similarity NPC290803
0.8978 High Similarity NPC80035
0.8978 High Similarity NPC249272
0.8973 High Similarity NPC154683
0.8973 High Similarity NPC40356
0.8971 High Similarity NPC225051
0.8971 High Similarity NPC114183
0.8971 High Similarity NPC52407
0.8971 High Similarity NPC37299
0.8971 High Similarity NPC180261
0.8966 High Similarity NPC147735
0.8966 High Similarity NPC294646
0.8966 High Similarity NPC205766
0.8963 High Similarity NPC205992
0.8963 High Similarity NPC93015
0.8947 High Similarity NPC116513
0.8944 High Similarity NPC19896
0.8939 High Similarity NPC103540
0.8939 High Similarity NPC477454
0.8939 High Similarity NPC10926
0.8936 High Similarity NPC257644
0.8936 High Similarity NPC137649
0.8929 High Similarity NPC315578
0.8919 High Similarity NPC470564
0.8913 High Similarity NPC194764
0.8913 High Similarity NPC272268
0.8913 High Similarity NPC264112
0.8913 High Similarity NPC65005
0.8912 High Similarity NPC208806
0.8905 High Similarity NPC270899
0.8904 High Similarity NPC35
0.8897 High Similarity NPC70622
0.8897 High Similarity NPC329933
0.8897 High Similarity NPC58685
0.8889 High Similarity NPC34802
0.8889 High Similarity NPC31799
0.8889 High Similarity NPC290194
0.8881 High Similarity NPC49282
0.8881 High Similarity NPC471683
0.8873 High Similarity NPC66593
0.8873 High Similarity NPC167663
0.8872 High Similarity NPC473691
0.8872 High Similarity NPC160499
0.8865 High Similarity NPC110810
0.8864 High Similarity NPC142956
0.8864 High Similarity NPC13238
0.8864 High Similarity NPC173978
0.8857 High Similarity NPC26924
0.8857 High Similarity NPC472903
0.8849 High Similarity NPC245923
0.8849 High Similarity NPC474110
0.8849 High Similarity NPC44960
0.8841 High Similarity NPC258502
0.8836 High Similarity NPC280295
0.8832 High Similarity NPC139074
0.8832 High Similarity NPC48036
0.8832 High Similarity NPC40524
0.8832 High Similarity NPC53896
0.8832 High Similarity NPC213485
0.8828 High Similarity NPC471907
0.8824 High Similarity NPC474517
0.8824 High Similarity NPC475042
0.8824 High Similarity NPC72669
0.8824 High Similarity NPC244699
0.8815 High Similarity NPC146647
0.8815 High Similarity NPC34414
0.8803 High Similarity NPC49108
0.88 High Similarity NPC324736
0.8794 High Similarity NPC183345
0.8788 High Similarity NPC375356
0.8784 High Similarity NPC214632
0.8784 High Similarity NPC107109
0.8777 High Similarity NPC474813
0.8777 High Similarity NPC155211
0.8768 High Similarity NPC475088
0.8768 High Similarity NPC288089
0.8768 High Similarity NPC474519
0.8767 High Similarity NPC477221
0.8767 High Similarity NPC10027
0.8767 High Similarity NPC65775
0.875 High Similarity NPC199253
0.875 High Similarity NPC247477
0.875 High Similarity NPC478019
0.875 High Similarity NPC136588
0.875 High Similarity NPC62219
0.875 High Similarity NPC17840
0.8741 High Similarity NPC179898
0.8741 High Similarity NPC84266
0.8741 High Similarity NPC96024
0.8733 High Similarity NPC199463
0.8733 High Similarity NPC178976
0.8733 High Similarity NPC37543
0.8732 High Similarity NPC472904
0.8731 High Similarity NPC3224
0.8725 High Similarity NPC66029
0.8714 High Similarity NPC62272
0.8712 High Similarity NPC300274
0.8712 High Similarity NPC309765
0.8712 High Similarity NPC133909

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC242994 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
0.9773 High Similarity NPD1509 Clinical (unspecified phase)
0.9078 High Similarity NPD7390 Discontinued
0.8939 High Similarity NPD1470 Approved
0.8714 High Similarity NPD5406 Approved
0.8714 High Similarity NPD5408 Approved
0.8714 High Similarity NPD5405 Approved
0.8714 High Similarity NPD5404 Approved
0.8636 High Similarity NPD1201 Approved
0.8623 High Similarity NPD943 Approved
0.8387 Intermediate Similarity NPD6232 Discontinued
0.8344 Intermediate Similarity NPD7473 Discontinued
0.8252 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD1607 Approved
0.817 Intermediate Similarity NPD7819 Suspended
0.8125 Intermediate Similarity NPD1510 Phase 2
0.8121 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8099 Intermediate Similarity NPD1240 Approved
0.8089 Intermediate Similarity NPD6959 Discontinued
0.8045 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.8026 Intermediate Similarity NPD3226 Approved
0.8 Intermediate Similarity NPD2533 Approved
0.8 Intermediate Similarity NPD2534 Approved
0.8 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD2532 Approved
0.7935 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD4380 Phase 2
0.7857 Intermediate Similarity NPD1164 Approved
0.7838 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD1549 Phase 2
0.7823 Intermediate Similarity NPD2935 Discontinued
0.7806 Intermediate Similarity NPD7411 Suspended
0.7785 Intermediate Similarity NPD3749 Approved
0.777 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD2346 Discontinued
0.7733 Intermediate Similarity NPD3750 Approved
0.7707 Intermediate Similarity NPD2801 Approved
0.7703 Intermediate Similarity NPD2796 Approved
0.7697 Intermediate Similarity NPD1511 Approved
0.7681 Intermediate Similarity NPD3019 Approved
0.7673 Intermediate Similarity NPD7075 Discontinued
0.7643 Intermediate Similarity NPD1934 Approved
0.761 Intermediate Similarity NPD7768 Phase 2
0.761 Intermediate Similarity NPD3882 Suspended
0.7609 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD1512 Approved
0.7595 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD3764 Approved
0.7576 Intermediate Similarity NPD5844 Phase 1
0.7576 Intermediate Similarity NPD6020 Phase 2
0.7554 Intermediate Similarity NPD2932 Approved
0.755 Intermediate Similarity NPD2800 Approved
0.7533 Intermediate Similarity NPD2344 Approved
0.7517 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD2799 Discontinued
0.7516 Intermediate Similarity NPD3300 Phase 2
0.7516 Intermediate Similarity NPD6599 Discontinued
0.7469 Intermediate Similarity NPD5494 Approved
0.7467 Intermediate Similarity NPD6099 Approved
0.7467 Intermediate Similarity NPD6100 Approved
0.7457 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD6801 Discontinued
0.74 Intermediate Similarity NPD3748 Approved
0.7394 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD6166 Phase 2
0.7394 Intermediate Similarity NPD9269 Phase 2
0.7388 Intermediate Similarity NPD4750 Phase 3
0.7386 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7003 Approved
0.7383 Intermediate Similarity NPD6651 Approved
0.7378 Intermediate Similarity NPD5710 Approved
0.7378 Intermediate Similarity NPD5711 Approved
0.7372 Intermediate Similarity NPD5951 Approved
0.7357 Intermediate Similarity NPD9268 Approved
0.7355 Intermediate Similarity NPD6799 Approved
0.7351 Intermediate Similarity NPD1551 Phase 2
0.7346 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD2309 Approved
0.7337 Intermediate Similarity NPD6559 Discontinued
0.7326 Intermediate Similarity NPD8150 Discontinued
0.731 Intermediate Similarity NPD2798 Approved
0.7305 Intermediate Similarity NPD3818 Discontinued
0.7284 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD4625 Phase 3
0.7278 Intermediate Similarity NPD5953 Discontinued
0.7273 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6534 Approved
0.7273 Intermediate Similarity NPD6535 Approved
0.7254 Intermediate Similarity NPD3026 Approved
0.7254 Intermediate Similarity NPD3023 Approved
0.7239 Intermediate Similarity NPD2342 Discontinued
0.7234 Intermediate Similarity NPD3024 Approved
0.7234 Intermediate Similarity NPD3025 Approved
0.7233 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD7458 Discontinued
0.723 Intermediate Similarity NPD2313 Discontinued
0.7222 Intermediate Similarity NPD3817 Phase 2
0.7208 Intermediate Similarity NPD1243 Approved
0.72 Intermediate Similarity NPD230 Phase 1
0.719 Intermediate Similarity NPD1471 Phase 3
0.7185 Intermediate Similarity NPD9266 Approved
0.7185 Intermediate Similarity NPD74 Approved
0.7167 Intermediate Similarity NPD6777 Approved
0.7167 Intermediate Similarity NPD6776 Approved
0.7167 Intermediate Similarity NPD6780 Approved
0.7167 Intermediate Similarity NPD6782 Approved
0.7167 Intermediate Similarity NPD6779 Approved
0.7167 Intermediate Similarity NPD6778 Approved
0.7167 Intermediate Similarity NPD6781 Approved
0.716 Intermediate Similarity NPD1465 Phase 2
0.716 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD3972 Approved
0.7151 Intermediate Similarity NPD7699 Phase 2
0.7151 Intermediate Similarity NPD7700 Phase 2
0.7143 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD9493 Approved
0.7126 Intermediate Similarity NPD3926 Phase 2
0.7121 Intermediate Similarity NPD940 Approved
0.7121 Intermediate Similarity NPD846 Approved
0.7118 Intermediate Similarity NPD7074 Phase 3
0.7113 Intermediate Similarity NPD1651 Approved
0.7111 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD9267 Approved
0.7111 Intermediate Similarity NPD9263 Approved
0.7111 Intermediate Similarity NPD9264 Approved
0.7107 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD920 Approved
0.7101 Intermediate Similarity NPD7635 Approved
0.7093 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7286 Phase 2
0.7059 Intermediate Similarity NPD7054 Approved
0.7055 Intermediate Similarity NPD1283 Approved
0.7052 Intermediate Similarity NPD8313 Approved
0.7052 Intermediate Similarity NPD8312 Approved
0.7051 Intermediate Similarity NPD4628 Phase 3
0.7049 Intermediate Similarity NPD7696 Phase 3
0.7049 Intermediate Similarity NPD7698 Approved
0.7049 Intermediate Similarity NPD7697 Approved
0.7049 Intermediate Similarity NPD7435 Discontinued
0.7045 Intermediate Similarity NPD1242 Phase 1
0.7043 Intermediate Similarity NPD8151 Discontinued
0.7022 Intermediate Similarity NPD6212 Phase 3
0.7022 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD6213 Phase 3
0.7018 Intermediate Similarity NPD7472 Approved
0.7012 Intermediate Similarity NPD5402 Approved
0.7012 Intermediate Similarity NPD8438 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD7870 Phase 2
0.7011 Intermediate Similarity NPD7871 Phase 2
0.7011 Intermediate Similarity NPD8320 Phase 1
0.7011 Intermediate Similarity NPD8319 Approved
0.7007 Intermediate Similarity NPD1203 Approved
0.7 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.6994 Remote Similarity NPD37 Approved
0.6981 Remote Similarity NPD642 Clinical (unspecified phase)
0.6977 Remote Similarity NPD6797 Phase 2
0.6964 Remote Similarity NPD7229 Phase 3
0.6962 Remote Similarity NPD643 Clinical (unspecified phase)
0.6954 Remote Similarity NPD6663 Approved
0.6948 Remote Similarity NPD4308 Phase 3
0.6944 Remote Similarity NPD4626 Approved
0.6943 Remote Similarity NPD8166 Discontinued
0.6939 Remote Similarity NPD1876 Approved
0.6936 Remote Similarity NPD7251 Discontinued
0.6935 Remote Similarity NPD6973 Clinical (unspecified phase)
0.6923 Remote Similarity NPD9545 Approved
0.6918 Remote Similarity NPD4878 Approved
0.6913 Remote Similarity NPD5736 Approved
0.6905 Remote Similarity NPD1247 Approved
0.6901 Remote Similarity NPD3751 Discontinued
0.6901 Remote Similarity NPD7177 Discontinued
0.6899 Remote Similarity NPD6190 Approved
0.6898 Remote Similarity NPD7701 Phase 2
0.6897 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6897 Remote Similarity NPD7808 Phase 3
0.6894 Remote Similarity NPD5403 Approved
0.6887 Remote Similarity NPD411 Approved
0.6887 Remote Similarity NPD3268 Approved
0.6886 Remote Similarity NPD919 Approved
0.6886 Remote Similarity NPD6234 Discontinued
0.6882 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6879 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6879 Remote Similarity NPD9281 Approved
0.6875 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6867 Remote Similarity NPD4966 Approved
0.6867 Remote Similarity NPD4965 Approved
0.6867 Remote Similarity NPD4908 Phase 1
0.6867 Remote Similarity NPD4967 Phase 2
0.6854 Remote Similarity NPD4287 Approved
0.6849 Remote Similarity NPD1281 Approved
0.6842 Remote Similarity NPD3020 Approved
0.6832 Remote Similarity NPD6273 Approved

Structure

External Identifiers

PubChem CID   23628281
ChEMBL   CHEMBL231553
ZINC  

Physicochemical Properties

Molecular Weight:  326.12
ALogP:  -1.7288
MLogP:  3
XLogP:  2.272
# Rotatable Bonds:  8
Polar Surface Area:  94.83
# H-Bond Aceptor:  2
# H-Bond Donor:  3
# 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