Natural Product: NPC476772

Natural Product ID:  NPC476772
Common Name:   3-[(2S,3R,4R,5S)-4-acetyl-3,4-dihydroxy-5-(1-hydroxy-2-oxopropyl)oxolan-2-yl]oxy-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
IUPAC Name:   3-[(2S,3R,4R,5S)-4-acetyl-3,4-dihydroxy-5-(1-hydroxy-2-oxopropyl)oxolan-2-yl]oxy-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
Synonyms:  
Molecular Formula:   C24H22O14
Standard InCHIKey:  KQYXUZWQTVRPNK-DESGVGLMSA-N
Standard InCHI:  InChI=1S/C24H22O14/c1-7(25)16(31)22-24(35,8(2)26)21(34)23(38-22)37-20-18(33)15-11(28)5-10(27)6-14(15)36-19(20)9-3-12(29)17(32)13(30)4-9/h3-6,16,21-23,27-32,34-35H,1-2H3/t16?,21-,22-,23+,24+/m0/s1
Canonical SMILES:  Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1O[C@H]([C@@]([C@H]1O)(O)C(=O)C)C(C(=O)C)O)c1cc(O)c(c(c1)O)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
NPO33517 Calycolpus warszewiczianus Species Myrtaceae Eukaryota young leaves Barro Colorado Nature Monument in Gatún Lake, Republic of Panama 2004-FEB PMID[16724851]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 50000 nM 16724851
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 456000 nM 16724851

  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 NPC476772 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
0.9875 High Similarity NPC476771
0.9688 High Similarity NPC34531
0.9632 High Similarity NPC245452
0.9627 High Similarity NPC255615
0.9627 High Similarity NPC67037
0.9506 High Similarity NPC135599
0.9506 High Similarity NPC254306
0.9506 High Similarity NPC328940
0.9506 High Similarity NPC113968
0.9506 High Similarity NPC277174
0.9506 High Similarity NPC73855
0.9451 High Similarity NPC72249
0.9448 High Similarity NPC149244
0.9448 High Similarity NPC84362
0.9448 High Similarity NPC317489
0.9448 High Similarity NPC325555
0.9448 High Similarity NPC52550
0.9448 High Similarity NPC223424
0.9448 High Similarity NPC265530
0.9448 High Similarity NPC226304
0.9448 High Similarity NPC48640
0.9448 High Similarity NPC127546
0.9448 High Similarity NPC173637
0.9444 High Similarity NPC19388
0.9444 High Similarity NPC55786
0.9444 High Similarity NPC240431
0.9394 High Similarity NPC175107
0.9394 High Similarity NPC190003
0.939 High Similarity NPC225434
0.939 High Similarity NPC219904
0.939 High Similarity NPC120099
0.939 High Similarity NPC138927
0.939 High Similarity NPC203050
0.939 High Similarity NPC223747
0.9387 High Similarity NPC274618
0.9387 High Similarity NPC56077
0.9387 High Similarity NPC118284
0.9387 High Similarity NPC308404
0.9387 High Similarity NPC88789
0.9387 High Similarity NPC145038
0.9387 High Similarity NPC281131
0.9387 High Similarity NPC253662
0.9387 High Similarity NPC179950
0.9387 High Similarity NPC276222
0.9341 High Similarity NPC296018
0.9341 High Similarity NPC154741
0.9337 High Similarity NPC4390
0.9337 High Similarity NPC45522
0.9337 High Similarity NPC24043
0.9337 High Similarity NPC101026
0.9337 High Similarity NPC21666
0.9337 High Similarity NPC169977
0.9337 High Similarity NPC42773
0.9333 High Similarity NPC116864
0.9333 High Similarity NPC95866
0.9333 High Similarity NPC235260
0.9333 High Similarity NPC206123
0.9333 High Similarity NPC20505
0.9333 High Similarity NPC212748
0.9333 High Similarity NPC155763
0.9333 High Similarity NPC244776
0.9329 High Similarity NPC76482
0.9325 High Similarity NPC277205
0.9321 High Similarity NPC473043
0.929 High Similarity NPC473073
0.929 High Similarity NPC473071
0.9286 High Similarity NPC476773
0.9277 High Similarity NPC471748
0.9277 High Similarity NPC153755
0.9277 High Similarity NPC134532
0.9277 High Similarity NPC117260
0.9277 High Similarity NPC471725
0.9277 High Similarity NPC235575
0.9277 High Similarity NPC155877
0.9277 High Similarity NPC33054
0.9277 High Similarity NPC176740
0.9277 High Similarity NPC476405
0.9277 High Similarity NPC203259
0.9273 High Similarity NPC52382
0.9273 High Similarity NPC227508
0.9273 High Similarity NPC270578
0.9268 High Similarity NPC21100
0.9268 High Similarity NPC197285
0.9264 High Similarity NPC284960
0.9264 High Similarity NPC222936
0.9264 High Similarity NPC19709
0.9235 High Similarity NPC473072
0.9226 High Similarity NPC472385
0.9226 High Similarity NPC198324
0.9226 High Similarity NPC470949
0.9226 High Similarity NPC65563
0.9217 High Similarity NPC282987
0.9217 High Similarity NPC254855
0.9217 High Similarity NPC156869
0.9217 High Similarity NPC245014
0.9217 High Similarity NPC136042
0.9217 High Similarity NPC67105
0.9217 High Similarity NPC255157
0.9217 High Similarity NPC29958
0.9217 High Similarity NPC67326
0.9217 High Similarity NPC84265
0.9217 High Similarity NPC259896
0.9212 High Similarity NPC160156
0.9212 High Similarity NPC92565
0.9212 High Similarity NPC275454
0.9207 High Similarity NPC22832
0.9207 High Similarity NPC311830
0.9202 High Similarity NPC127782
0.9202 High Similarity NPC189142
0.9202 High Similarity NPC300537
0.9202 High Similarity NPC150164
0.9202 High Similarity NPC77660
0.9193 High Similarity NPC288084
0.9172 High Similarity NPC293626
0.9172 High Similarity NPC217387
0.9172 High Similarity NPC196127
0.9172 High Similarity NPC258044
0.9172 High Similarity NPC35167
0.9172 High Similarity NPC267680
0.9172 High Similarity NPC168584
0.9167 High Similarity NPC264735
0.9167 High Similarity NPC16194
0.9167 High Similarity NPC220173
0.9167 High Similarity NPC19108
0.9167 High Similarity NPC477848
0.9167 High Similarity NPC237435
0.9167 High Similarity NPC115760
0.9167 High Similarity NPC476472
0.9167 High Similarity NPC473327
0.9167 High Similarity NPC135277
0.9167 High Similarity NPC43211
0.9167 High Similarity NPC294815
0.9167 High Similarity NPC294629
0.9167 High Similarity NPC101191
0.9167 High Similarity NPC49344
0.9167 High Similarity NPC210094
0.9167 High Similarity NPC253685
0.9162 High Similarity NPC60735
0.9162 High Similarity NPC261254
0.9162 High Similarity NPC26230
0.9157 High Similarity NPC469931
0.9157 High Similarity NPC45638
0.9157 High Similarity NPC186807
0.9157 High Similarity NPC475942
0.9157 High Similarity NPC201292
0.9157 High Similarity NPC105025
0.9157 High Similarity NPC93337
0.9157 High Similarity NPC58053
0.9157 High Similarity NPC226294
0.9152 High Similarity NPC115674
0.9152 High Similarity NPC210073
0.9146 High Similarity NPC243930
0.9146 High Similarity NPC309025
0.9146 High Similarity NPC94777
0.9146 High Similarity NPC191306
0.9146 High Similarity NPC88043
0.9146 High Similarity NPC168822
0.9146 High Similarity NPC88023
0.9146 High Similarity NPC270335
0.9118 High Similarity NPC241423
0.9118 High Similarity NPC110941
0.9118 High Similarity NPC473571
0.9118 High Similarity NPC126784
0.9118 High Similarity NPC473682
0.9118 High Similarity NPC470444
0.9118 High Similarity NPC470443
0.9112 High Similarity NPC122467
0.9112 High Similarity NPC14187
0.9112 High Similarity NPC61904
0.9112 High Similarity NPC169733
0.9112 High Similarity NPC211532
0.9112 High Similarity NPC89127
0.9112 High Similarity NPC257714
0.9112 High Similarity NPC471669
0.9112 High Similarity NPC233994
0.9112 High Similarity NPC292019
0.9112 High Similarity NPC8573
0.9112 High Similarity NPC144097
0.9112 High Similarity NPC202908
0.9102 High Similarity NPC224462
0.9102 High Similarity NPC285197
0.9096 High Similarity NPC42892
0.9096 High Similarity NPC116745
0.9096 High Similarity NPC229729
0.9096 High Similarity NPC58716
0.9096 High Similarity NPC146792
0.9096 High Similarity NPC45618
0.9091 High Similarity NPC72016
0.9091 High Similarity NPC165720
0.908 High Similarity NPC269906
0.908 High Similarity NPC110349
0.9059 High Similarity NPC113836
0.9059 High Similarity NPC37668
0.9059 High Similarity NPC251417
0.9059 High Similarity NPC217520
0.9059 High Similarity NPC89052
0.9059 High Similarity NPC173837
0.9059 High Similarity NPC253521
0.9059 High Similarity NPC139571
0.9053 High Similarity NPC108202

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC476772 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
0.9329 High Similarity NPD3818 Discontinued
0.9277 High Similarity NPD6797 Phase 2
0.9222 High Similarity NPD7251 Discontinued
0.9167 High Similarity NPD4338 Clinical (unspecified phase)
0.9053 High Similarity NPD7808 Phase 3
0.9042 High Similarity NPD7054 Approved
0.8988 High Similarity NPD7472 Approved
0.8896 High Similarity NPD3882 Suspended
0.8876 High Similarity NPD7074 Phase 3
0.8727 High Similarity NPD4381 Clinical (unspecified phase)
0.872 High Similarity NPD3817 Phase 2
0.8706 High Similarity NPD7804 Clinical (unspecified phase)
0.8659 High Similarity NPD2801 Approved
0.8639 High Similarity NPD6167 Clinical (unspecified phase)
0.8639 High Similarity NPD6166 Phase 2
0.8639 High Similarity NPD6168 Clinical (unspecified phase)
0.8598 High Similarity NPD1934 Approved
0.8571 High Similarity NPD1512 Approved
0.8545 High Similarity NPD2393 Clinical (unspecified phase)
0.8447 Intermediate Similarity NPD1511 Approved
0.8343 Intermediate Similarity NPD6559 Discontinued
0.8333 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD7075 Discontinued
0.8274 Intermediate Similarity NPD5402 Approved
0.8263 Intermediate Similarity NPD6801 Discontinued
0.8182 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8144 Intermediate Similarity NPD4380 Phase 2
0.811 Intermediate Similarity NPD6799 Approved
0.8107 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8072 Intermediate Similarity NPD5403 Approved
0.8035 Intermediate Similarity NPD1247 Approved
0.7977 Intermediate Similarity NPD5494 Approved
0.7952 Intermediate Similarity NPD5401 Approved
0.7943 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD6234 Discontinued
0.791 Intermediate Similarity NPD3751 Discontinued
0.7886 Intermediate Similarity NPD3787 Discontinued
0.7857 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD37 Approved
0.7833 Intermediate Similarity NPD7685 Pre-registration
0.7829 Intermediate Similarity NPD7199 Phase 2
0.7824 Intermediate Similarity NPD6599 Discontinued
0.7816 Intermediate Similarity NPD919 Approved
0.7811 Intermediate Similarity NPD1653 Approved
0.7809 Intermediate Similarity NPD7228 Approved
0.7805 Intermediate Similarity NPD1549 Phase 2
0.7803 Intermediate Similarity NPD4965 Approved
0.7803 Intermediate Similarity NPD4967 Phase 2
0.7803 Intermediate Similarity NPD4966 Approved
0.7791 Intermediate Similarity NPD2796 Approved
0.7784 Intermediate Similarity NPD6232 Discontinued
0.7778 Intermediate Similarity NPD7411 Suspended
0.7771 Intermediate Similarity NPD6190 Approved
0.776 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7753 Intermediate Similarity NPD7473 Discontinued
0.774 Intermediate Similarity NPD3926 Phase 2
0.7738 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD1510 Phase 2
0.7688 Intermediate Similarity NPD1465 Phase 2
0.7688 Intermediate Similarity NPD7819 Suspended
0.7627 Intermediate Similarity NPD6959 Discontinued
0.7605 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD5844 Phase 1
0.7552 Intermediate Similarity NPD6781 Approved
0.7552 Intermediate Similarity NPD6777 Approved
0.7552 Intermediate Similarity NPD6776 Approved
0.7552 Intermediate Similarity NPD6780 Approved
0.7552 Intermediate Similarity NPD6778 Approved
0.7552 Intermediate Similarity NPD6779 Approved
0.7552 Intermediate Similarity NPD6782 Approved
0.7546 Intermediate Similarity NPD230 Phase 1
0.7529 Intermediate Similarity NPD2533 Approved
0.7529 Intermediate Similarity NPD2534 Approved
0.7529 Intermediate Similarity NPD2532 Approved
0.7527 Intermediate Similarity NPD8434 Phase 2
0.7526 Intermediate Similarity NPD7435 Discontinued
0.75 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD943 Approved
0.7485 Intermediate Similarity NPD1240 Approved
0.7485 Intermediate Similarity NPD1613 Approved
0.7485 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD8313 Approved
0.7459 Intermediate Similarity NPD8312 Approved
0.7458 Intermediate Similarity NPD3749 Approved
0.7447 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD2800 Approved
0.7411 Intermediate Similarity NPD7584 Approved
0.7403 Intermediate Similarity NPD2403 Approved
0.7394 Intermediate Similarity NPD1607 Approved
0.7351 Intermediate Similarity NPD7240 Approved
0.7347 Intermediate Similarity NPD7697 Approved
0.7347 Intermediate Similarity NPD7698 Approved
0.7347 Intermediate Similarity NPD7696 Phase 3
0.7341 Intermediate Similarity NPD920 Approved
0.7337 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD8151 Discontinued
0.7321 Intermediate Similarity NPD7266 Discontinued
0.731 Intermediate Similarity NPD7871 Phase 2
0.731 Intermediate Similarity NPD7870 Phase 2
0.7306 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD3027 Phase 3
0.73 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD7874 Approved
0.7294 Intermediate Similarity NPD4628 Phase 3
0.7294 Intermediate Similarity NPD3750 Approved
0.7292 Intermediate Similarity NPD6535 Approved
0.7292 Intermediate Similarity NPD6534 Approved
0.7286 Intermediate Similarity NPD7701 Phase 2
0.7284 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD1551 Phase 2
0.7257 Intermediate Similarity NPD3226 Approved
0.7256 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD1243 Approved
0.7229 Intermediate Similarity NPD1933 Approved
0.7229 Intermediate Similarity NPD447 Suspended
0.7225 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD7768 Phase 2
0.7202 Intermediate Similarity NPD7033 Discontinued
0.7194 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7699 Phase 2
0.7179 Intermediate Similarity NPD7700 Phase 2
0.7178 Intermediate Similarity NPD7783 Phase 2
0.7178 Intermediate Similarity NPD7801 Approved
0.7178 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD2935 Discontinued
0.7136 Intermediate Similarity NPD8319 Approved
0.7136 Intermediate Similarity NPD8320 Phase 1
0.7135 Intermediate Similarity NPD2163 Approved
0.7121 Intermediate Similarity NPD6823 Phase 2
0.7118 Intermediate Similarity NPD2344 Approved
0.7112 Intermediate Similarity NPD5953 Discontinued
0.711 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD8455 Phase 2
0.7068 Intermediate Similarity NPD8150 Discontinued
0.7059 Intermediate Similarity NPD6100 Approved
0.7059 Intermediate Similarity NPD6099 Approved
0.7056 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD6798 Discontinued
0.703 Intermediate Similarity NPD7585 Approved
0.7027 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD6355 Discontinued
0.7011 Intermediate Similarity NPD5710 Approved
0.7011 Intermediate Similarity NPD5711 Approved
0.7006 Intermediate Similarity NPD6233 Phase 2
0.7005 Intermediate Similarity NPD7286 Phase 2
0.7 Intermediate Similarity NPD3748 Approved
0.6982 Remote Similarity NPD6651 Approved
0.698 Remote Similarity NPD7583 Approved
0.697 Remote Similarity NPD9494 Approved
0.6967 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6963 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6954 Remote Similarity NPD2309 Approved
0.6952 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6946 Remote Similarity NPD2313 Discontinued
0.6946 Remote Similarity NPD3268 Approved
0.694 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6932 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6928 Remote Similarity NPD6832 Phase 2
0.6919 Remote Similarity NPD1471 Phase 3
0.6915 Remote Similarity NPD7680 Approved
0.6914 Remote Similarity NPD1091 Approved
0.6909 Remote Similarity NPD2798 Approved
0.6908 Remote Similarity NPD7930 Approved
0.6901 Remote Similarity NPD2799 Discontinued
0.6901 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7390 Discontinued
0.6872 Remote Similarity NPD7458 Discontinued
0.6871 Remote Similarity NPD9269 Phase 2
0.6868 Remote Similarity NPD5353 Approved
0.6866 Remote Similarity NPD5006 Approved
0.6866 Remote Similarity NPD5005 Approved
0.6853 Remote Similarity NPD4360 Phase 2
0.6853 Remote Similarity NPD4363 Phase 3
0.6851 Remote Similarity NPD6844 Discontinued
0.6848 Remote Similarity NPD1203 Approved
0.6839 Remote Similarity NPD2654 Approved
0.6839 Remote Similarity NPD6674 Discontinued
0.6839 Remote Similarity NPD1652 Phase 2
0.6836 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6829 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6828 Remote Similarity NPD7229 Phase 3
0.6824 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6821 Remote Similarity NPD2346 Discontinued
0.6818 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6818 Remote Similarity NPD4361 Phase 2
0.6816 Remote Similarity NPD2493 Approved
0.6816 Remote Similarity NPD2494 Approved
0.6802 Remote Similarity NPD6212 Phase 3
0.6802 Remote Similarity NPD6213 Phase 3

Structure

External Identifiers

PubChem CID   44583838
ChEMBL   CHEMBL525002
ZINC  

Physicochemical Properties

Molecular Weight:  534.10
ALogP:  -5.7527
MLogP:  2.56
XLogP:  -1.066
# Rotatable Bonds:  16
Polar Surface Area:  240.74
# H-Bond Aceptor:  8
# H-Bond Donor:  8
# Rings:  4
# Heavy Atoms:  38

Download Data

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