Natural Product: NPC213622

Natural Product ID:  NPC213622
Common Name:   Amyrisin C
IUPAC Name:   5,7-dihydroxy-6-methoxy-2-[3-methoxy-4-(3-methylbut-2-enoxy)phenyl]chromen-4-one
Synonyms:   Amyrisin C
Molecular Formula:   C22H22O7
Standard InCHIKey:  ABZZDWBIZJSCNU-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C22H22O7/c1-12(2)7-8-28-16-6-5-13(9-18(16)26-3)17-10-14(23)20-19(29-17)11-15(24)22(27-4)21(20)25/h5-7,9-11,24-25H,8H2,1-4H3
Canonical SMILES:  COc1cc(ccc1OCC=C(C)C)c1cc(=O)c2c(o1)cc(c(c2O)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
NPO1170 Amyris madrensis Species Rutaceae Eukaryota PMID[22260294]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT90 Cell Line DU-145 Homo sapiens IC50 = 23000 nM 22182501
NPT306 Cell Line PC-3 Homo sapiens IC50 = 23000 nM 226705

  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 NPC213622 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
0.9932 High Similarity NPC255350
0.9932 High Similarity NPC176775
0.9932 High Similarity NPC69394
0.9932 High Similarity NPC274327
0.9932 High Similarity NPC183878
0.9932 High Similarity NPC231018
0.9932 High Similarity NPC160951
0.9932 High Similarity NPC145379
0.9932 High Similarity NPC47781
0.9932 High Similarity NPC22519
0.9866 High Similarity NPC470402
0.9865 High Similarity NPC256612
0.9865 High Similarity NPC146165
0.9865 High Similarity NPC92659
0.9865 High Similarity NPC163780
0.9865 High Similarity NPC201136
0.9865 High Similarity NPC167815
0.9865 High Similarity NPC128863
0.9865 High Similarity NPC227325
0.9865 High Similarity NPC2476
0.9865 High Similarity NPC280339
0.9865 High Similarity NPC4455
0.9865 High Similarity NPC138360
0.9865 High Similarity NPC50715
0.9865 High Similarity NPC20830
0.9865 High Similarity NPC183597
0.9865 High Similarity NPC196439
0.9864 High Similarity NPC25270
0.9864 High Similarity NPC100887
0.9864 High Similarity NPC275836
0.9864 High Similarity NPC198826
0.9864 High Similarity NPC212678
0.9864 High Similarity NPC187498
0.9864 High Similarity NPC57030
0.9864 High Similarity NPC120163
0.9864 High Similarity NPC131624
0.9864 High Similarity NPC156222
0.9864 High Similarity NPC241498
0.9864 High Similarity NPC83508
0.9864 High Similarity NPC71334
0.9864 High Similarity NPC188203
0.9864 High Similarity NPC222830
0.9864 High Similarity NPC301323
0.9864 High Similarity NPC239128
0.9864 High Similarity NPC162313
0.9864 High Similarity NPC293183
0.9864 High Similarity NPC256283
0.9864 High Similarity NPC275722
0.9799 High Similarity NPC472916
0.9799 High Similarity NPC49824
0.9797 High Similarity NPC250822
0.9797 High Similarity NPC75279
0.9797 High Similarity NPC276409
0.9796 High Similarity NPC226973
0.9796 High Similarity NPC208043
0.9733 High Similarity NPC101830
0.9733 High Similarity NPC472910
0.9733 High Similarity NPC48208
0.9733 High Similarity NPC472913
0.9733 High Similarity NPC93376
0.9733 High Similarity NPC474836
0.9733 High Similarity NPC472914
0.9733 High Similarity NPC75215
0.9733 High Similarity NPC156057
0.9733 High Similarity NPC474208
0.9733 High Similarity NPC227192
0.9733 High Similarity NPC189179
0.9733 High Similarity NPC203891
0.9733 High Similarity NPC224137
0.9733 High Similarity NPC222814
0.9733 High Similarity NPC96167
0.9733 High Similarity NPC110070
0.9733 High Similarity NPC472911
0.9733 High Similarity NPC475267
0.9733 High Similarity NPC162869
0.9733 High Similarity NPC245758
0.9732 High Similarity NPC208197
0.9732 High Similarity NPC201451
0.9732 High Similarity NPC26227
0.9732 High Similarity NPC2928
0.9732 High Similarity NPC44079
0.973 High Similarity NPC39732
0.973 High Similarity NPC142540
0.973 High Similarity NPC60972
0.9728 High Similarity NPC306821
0.9728 High Similarity NPC184136
0.9669 High Similarity NPC143828
0.9669 High Similarity NPC300943
0.9669 High Similarity NPC191459
0.9669 High Similarity NPC4481
0.9669 High Similarity NPC204854
0.9669 High Similarity NPC22472
0.9669 High Similarity NPC152166
0.9669 High Similarity NPC19687
0.9669 High Similarity NPC18772
0.9669 High Similarity NPC7846
0.9669 High Similarity NPC288669
0.9669 High Similarity NPC105242
0.9669 High Similarity NPC176300
0.9669 High Similarity NPC253634
0.9669 High Similarity NPC115798
0.9669 High Similarity NPC25495
0.9669 High Similarity NPC9609
0.9669 High Similarity NPC18607
0.9669 High Similarity NPC261004
0.9669 High Similarity NPC130894
0.9667 High Similarity NPC247017
0.9667 High Similarity NPC245546
0.9667 High Similarity NPC255106
0.9667 High Similarity NPC474520
0.9667 High Similarity NPC98661
0.9667 High Similarity NPC43243
0.9667 High Similarity NPC235165
0.9667 High Similarity NPC266960
0.9667 High Similarity NPC292107
0.9664 High Similarity NPC472915
0.9664 High Similarity NPC280937
0.9664 High Similarity NPC86485
0.9664 High Similarity NPC124714
0.9662 High Similarity NPC308451
0.966 High Similarity NPC223579
0.966 High Similarity NPC259713
0.966 High Similarity NPC48479
0.966 High Similarity NPC183950
0.966 High Similarity NPC287101
0.966 High Similarity NPC296197
0.966 High Similarity NPC52005
0.966 High Similarity NPC216318
0.966 High Similarity NPC328119
0.966 High Similarity NPC177298
0.966 High Similarity NPC137062
0.966 High Similarity NPC17286
0.9605 High Similarity NPC476980
0.9603 High Similarity NPC210084
0.9603 High Similarity NPC29841
0.9603 High Similarity NPC469584
0.9603 High Similarity NPC176665
0.9603 High Similarity NPC163524
0.9603 High Similarity NPC472438
0.9603 High Similarity NPC78302
0.9603 High Similarity NPC305663
0.9603 High Similarity NPC99597
0.9603 High Similarity NPC287979
0.9603 High Similarity NPC235215
0.9603 High Similarity NPC78225
0.9603 High Similarity NPC7973
0.96 High Similarity NPC189960
0.96 High Similarity NPC37392
0.96 High Similarity NPC472909
0.96 High Similarity NPC32557
0.9597 High Similarity NPC209487
0.9597 High Similarity NPC199100
0.9597 High Similarity NPC269451
0.9597 High Similarity NPC181209
0.9597 High Similarity NPC477231
0.9597 High Similarity NPC120537
0.9597 High Similarity NPC216769
0.9597 High Similarity NPC131266
0.9597 High Similarity NPC35763
0.9597 High Similarity NPC100971
0.9597 High Similarity NPC301123
0.9597 High Similarity NPC245382
0.9597 High Similarity NPC257648
0.9597 High Similarity NPC180234
0.9597 High Similarity NPC121522
0.9597 High Similarity NPC100263
0.9597 High Similarity NPC291802
0.9595 High Similarity NPC45873
0.9592 High Similarity NPC120464
0.9592 High Similarity NPC195202
0.9542 High Similarity NPC266314
0.9542 High Similarity NPC258331
0.9539 High Similarity NPC95936
0.9539 High Similarity NPC193842
0.9539 High Similarity NPC152904
0.9539 High Similarity NPC250214
0.9536 High Similarity NPC100916
0.9536 High Similarity NPC55619
0.9536 High Similarity NPC191146
0.9536 High Similarity NPC200388
0.9536 High Similarity NPC268161
0.9536 High Similarity NPC265511
0.9536 High Similarity NPC317383
0.9536 High Similarity NPC178854
0.9536 High Similarity NPC68093
0.9533 High Similarity NPC236223
0.9533 High Similarity NPC88645
0.9533 High Similarity NPC206238
0.9533 High Similarity NPC292214
0.9533 High Similarity NPC250557
0.9533 High Similarity NPC270620
0.9533 High Similarity NPC78326
0.9533 High Similarity NPC167091
0.9533 High Similarity NPC179126
0.9533 High Similarity NPC271779
0.9533 High Similarity NPC18727
0.953 High Similarity NPC225731
0.953 High Similarity NPC125062
0.953 High Similarity NPC45291
0.953 High Similarity NPC19980

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC213622 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
0.9932 High Similarity NPD2801 Approved
0.9467 High Similarity NPD1934 Approved
0.932 High Similarity NPD1511 Approved
0.9281 High Similarity NPD3882 Suspended
0.9276 High Similarity NPD2393 Clinical (unspecified phase)
0.9195 High Similarity NPD1512 Approved
0.9091 High Similarity NPD3817 Phase 2
0.9 High Similarity NPD3818 Discontinued
0.8994 High Similarity NPD6168 Clinical (unspecified phase)
0.8994 High Similarity NPD6167 Clinical (unspecified phase)
0.8994 High Similarity NPD6166 Phase 2
0.8957 High Similarity NPD4338 Clinical (unspecified phase)
0.8944 High Similarity NPD7054 Approved
0.8889 High Similarity NPD7472 Approved
0.8773 High Similarity NPD7074 Phase 3
0.875 High Similarity NPD4378 Clinical (unspecified phase)
0.8742 High Similarity NPD5494 Approved
0.872 High Similarity NPD6797 Phase 2
0.8671 High Similarity NPD4868 Clinical (unspecified phase)
0.8667 High Similarity NPD7251 Discontinued
0.8614 High Similarity NPD7808 Phase 3
0.859 High Similarity NPD4380 Phase 2
0.8533 High Similarity NPD1552 Clinical (unspecified phase)
0.8533 High Similarity NPD1550 Clinical (unspecified phase)
0.8523 High Similarity NPD1510 Phase 2
0.85 High Similarity NPD4381 Clinical (unspecified phase)
0.8491 Intermediate Similarity NPD5402 Approved
0.8477 Intermediate Similarity NPD1549 Phase 2
0.8467 Intermediate Similarity NPD2796 Approved
0.8442 Intermediate Similarity NPD6799 Approved
0.8405 Intermediate Similarity NPD6232 Discontinued
0.8385 Intermediate Similarity NPD7075 Discontinued
0.8364 Intermediate Similarity NPD7473 Discontinued
0.8344 Intermediate Similarity NPD1247 Approved
0.8313 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8269 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD5844 Phase 1
0.8255 Intermediate Similarity NPD943 Approved
0.8255 Intermediate Similarity NPD1240 Approved
0.825 Intermediate Similarity NPD6801 Discontinued
0.8199 Intermediate Similarity NPD7819 Suspended
0.8199 Intermediate Similarity NPD1465 Phase 2
0.8166 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8146 Intermediate Similarity NPD1607 Approved
0.8125 Intermediate Similarity NPD6599 Discontinued
0.8117 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD230 Phase 1
0.8075 Intermediate Similarity NPD7411 Suspended
0.805 Intermediate Similarity NPD5403 Approved
0.8024 Intermediate Similarity NPD3926 Phase 2
0.8013 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD1613 Approved
0.8012 Intermediate Similarity NPD6959 Discontinued
0.8 Intermediate Similarity NPD919 Approved
0.7987 Intermediate Similarity NPD2935 Discontinued
0.7987 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD447 Suspended
0.7933 Intermediate Similarity NPD3027 Phase 3
0.7925 Intermediate Similarity NPD5401 Approved
0.7919 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD6559 Discontinued
0.7898 Intermediate Similarity NPD3750 Approved
0.7888 Intermediate Similarity NPD1653 Approved
0.7881 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD1551 Phase 2
0.7834 Intermediate Similarity NPD2800 Approved
0.7826 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD2533 Approved
0.7812 Intermediate Similarity NPD2532 Approved
0.7812 Intermediate Similarity NPD2534 Approved
0.7806 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.78 Intermediate Similarity NPD9494 Approved
0.7797 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD7768 Phase 2
0.7765 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD6190 Approved
0.7725 Intermediate Similarity NPD3749 Approved
0.7722 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD920 Approved
0.7692 Intermediate Similarity NPD7199 Phase 2
0.7679 Intermediate Similarity NPD6234 Discontinued
0.7674 Intermediate Similarity NPD3751 Discontinued
0.7673 Intermediate Similarity NPD4628 Phase 3
0.7651 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD3787 Discontinued
0.764 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD1933 Approved
0.7609 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD2344 Approved
0.7593 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD3748 Approved
0.7557 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD5953 Discontinued
0.7532 Intermediate Similarity NPD6100 Approved
0.7532 Intermediate Similarity NPD6099 Approved
0.7532 Intermediate Similarity NPD2313 Discontinued
0.7529 Intermediate Similarity NPD7286 Phase 2
0.7528 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD3226 Approved
0.7514 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7685 Pre-registration
0.75 Intermediate Similarity NPD1243 Approved
0.7485 Intermediate Similarity NPD37 Approved
0.7485 Intermediate Similarity NPD6844 Discontinued
0.7483 Intermediate Similarity NPD1548 Phase 1
0.7469 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD2799 Discontinued
0.7456 Intermediate Similarity NPD4967 Phase 2
0.7456 Intermediate Similarity NPD4966 Approved
0.7456 Intermediate Similarity NPD4965 Approved
0.7452 Intermediate Similarity NPD6651 Approved
0.7434 Intermediate Similarity NPD1203 Approved
0.7407 Intermediate Similarity NPD2309 Approved
0.7403 Intermediate Similarity NPD6832 Phase 2
0.7403 Intermediate Similarity NPD4908 Phase 1
0.7399 Intermediate Similarity NPD5242 Approved
0.7389 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD2346 Discontinued
0.7372 Intermediate Similarity NPD6233 Phase 2
0.7371 Intermediate Similarity NPD7228 Approved
0.7358 Intermediate Similarity NPD7033 Discontinued
0.7351 Intermediate Similarity NPD9269 Phase 2
0.7321 Intermediate Similarity NPD6386 Approved
0.7321 Intermediate Similarity NPD6385 Approved
0.7317 Intermediate Similarity NPD7390 Discontinued
0.7308 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD3268 Approved
0.7294 Intermediate Similarity NPD5353 Approved
0.7293 Intermediate Similarity NPD8434 Phase 2
0.7285 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD1610 Phase 2
0.7285 Intermediate Similarity NPD422 Phase 1
0.7273 Intermediate Similarity NPD2798 Approved
0.7273 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD4363 Phase 3
0.7243 Intermediate Similarity NPD4360 Phase 2
0.7241 Intermediate Similarity NPD5711 Approved
0.7241 Intermediate Similarity NPD5710 Approved
0.7239 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD9717 Approved
0.7234 Intermediate Similarity NPD6782 Approved
0.7234 Intermediate Similarity NPD6780 Approved
0.7234 Intermediate Similarity NPD6777 Approved
0.7234 Intermediate Similarity NPD6781 Approved
0.7234 Intermediate Similarity NPD6776 Approved
0.7234 Intermediate Similarity NPD6778 Approved
0.7234 Intermediate Similarity NPD6779 Approved
0.7226 Intermediate Similarity NPD3018 Phase 2
0.7226 Intermediate Similarity NPD2861 Phase 2
0.7222 Intermediate Similarity NPD8312 Approved
0.7222 Intermediate Similarity NPD8313 Approved
0.7212 Intermediate Similarity NPD4357 Discontinued
0.7208 Intermediate Similarity NPD2797 Approved
0.7197 Intermediate Similarity NPD6798 Discontinued
0.7181 Intermediate Similarity NPD5536 Phase 2
0.7178 Intermediate Similarity NPD1652 Phase 2
0.7178 Intermediate Similarity NPD2654 Approved
0.7169 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD7549 Discontinued
0.7159 Intermediate Similarity NPD2403 Approved
0.7143 Intermediate Similarity NPD3225 Approved
0.7143 Intermediate Similarity NPD7229 Phase 3
0.7143 Intermediate Similarity NPD4308 Phase 3
0.7124 Intermediate Similarity NPD1608 Approved
0.712 Intermediate Similarity NPD7435 Discontinued
0.7118 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7112 Intermediate Similarity NPD4361 Phase 2
0.7112 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD8150 Discontinued
0.7098 Intermediate Similarity NPD7584 Approved
0.7089 Intermediate Similarity NPD411 Approved
0.7086 Intermediate Similarity NPD9268 Approved
0.7078 Intermediate Similarity NPD2982 Phase 2
0.7078 Intermediate Similarity NPD2983 Phase 2
0.7063 Intermediate Similarity NPD6355 Discontinued
0.7062 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD7266 Discontinued
0.705 Intermediate Similarity NPD2899 Discontinued
0.7041 Intermediate Similarity NPD7783 Phase 2
0.7041 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD7696 Phase 3
0.7031 Intermediate Similarity NPD7698 Approved
0.7031 Intermediate Similarity NPD7697 Approved
0.7026 Intermediate Similarity NPD8151 Discontinued
0.7025 Intermediate Similarity NPD4625 Phase 3
0.7024 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD9545 Approved
0.7017 Intermediate Similarity NPD7038 Approved
0.7017 Intermediate Similarity NPD7039 Approved
0.7013 Intermediate Similarity NPD1481 Phase 2
0.7013 Intermediate Similarity NPD2981 Phase 2
0.7012 Intermediate Similarity NPD2424 Discontinued
0.7007 Intermediate Similarity NPD228 Approved
0.7 Intermediate Similarity NPD7458 Discontinued

Structure

External Identifiers

PubChem CID   57381728
ChEMBL   CHEMBL2023533
ZINC  

Physicochemical Properties

Molecular Weight:  398.14
ALogP:  -0.1141
MLogP:  3.11
XLogP:  2.399
# Rotatable Bonds:  12
Polar Surface Area:  94.45
# H-Bond Aceptor:  1
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  29

Download Data

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