Natural Product: NPC475184

Natural Product ID:  NPC475184
Common Name:   Ent-Naringeninyl-(I-3Alpha,Ii-8)-4'-O-Methylnaringenin
IUPAC Name:   (2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-8-[(2R,3R)-4,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl]-2,3-dihydrochromen-4-one
Synonyms:  
Molecular Formula:   C31H26O10
Standard InCHIKey:  XNZXBSSGLCCBPV-FEVFIROASA-N
Standard InCHI:  InChI=1S/C31H26O10/c1-39-18-8-4-14(5-9-18)23-13-22(37)25-20(35)12-21(36)27(31(25)40-23)28-29(38)26-19(34)10-17(33)11-24(26)41-30(28)15-2-6-16(32)7-3-15/h2-12,23,28-30,32-36,38H,13H2,1H3/t23-,28+,29?,30-/m0/s1
Canonical SMILES:  COc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)c(c(cc2O)O)[C@H]1[C@@H](Oc2c(C1O)c(O)cc(c2)O)c1ccc(cc1)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
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota Root barks PMID[16562837]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT171 Cell Line MRC5 Homo sapiens IC50 = 38000 nM 20185316
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 34700 nM 22037378
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 6000 nM 22545792
NPT1021 Organism Leishmania infantum Leishmania infantum IC50 > 64000 nM 17256988
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 = 28300 nM 20681570

  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 NPC475184 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
0.9801 High Similarity NPC51247
0.98 High Similarity NPC69531
0.9735 High Similarity NPC257166
0.9735 High Similarity NPC1796
0.9733 High Similarity NPC300668
0.9733 High Similarity NPC134171
0.9671 High Similarity NPC15815
0.9671 High Similarity NPC51760
0.9669 High Similarity NPC61112
0.9669 High Similarity NPC198489
0.9669 High Similarity NPC32867
0.9608 High Similarity NPC98023
0.9608 High Similarity NPC226462
0.9608 High Similarity NPC42965
0.9605 High Similarity NPC271741
0.9605 High Similarity NPC287789
0.9603 High Similarity NPC258474
0.9603 High Similarity NPC201227
0.9603 High Similarity NPC182555
0.9603 High Similarity NPC66441
0.9548 High Similarity NPC63438
0.9545 High Similarity NPC301256
0.9545 High Similarity NPC312273
0.9542 High Similarity NPC295090
0.9542 High Similarity NPC105584
0.9539 High Similarity NPC309648
0.9536 High Similarity NPC121568
0.953 High Similarity NPC3642
0.9487 High Similarity NPC473010
0.9484 High Similarity NPC473012
0.9481 High Similarity NPC195136
0.9477 High Similarity NPC208258
0.9474 High Similarity NPC79375
0.9474 High Similarity NPC37253
0.947 High Similarity NPC174086
0.9463 High Similarity NPC122894
0.9423 High Similarity NPC473009
0.9416 High Similarity NPC123544
0.9408 High Similarity NPC71061
0.9408 High Similarity NPC290830
0.9408 High Similarity NPC194593
0.9408 High Similarity NPC72425
0.9408 High Similarity NPC303485
0.9404 High Similarity NPC178484
0.94 High Similarity NPC473016
0.9359 High Similarity NPC473011
0.9359 High Similarity NPC15374
0.9355 High Similarity NPC121647
0.9351 High Similarity NPC323627
0.9351 High Similarity NPC318527
0.9351 High Similarity NPC324358
0.9351 High Similarity NPC322459
0.9346 High Similarity NPC158027
0.9346 High Similarity NPC215203
0.9346 High Similarity NPC186227
0.9346 High Similarity NPC52611
0.9346 High Similarity NPC265624
0.9346 High Similarity NPC14606
0.9346 High Similarity NPC159707
0.9346 High Similarity NPC100049
0.9346 High Similarity NPC121649
0.9346 High Similarity NPC248739
0.9346 High Similarity NPC150908
0.9346 High Similarity NPC205026
0.9342 High Similarity NPC78324
0.9342 High Similarity NPC208011
0.9342 High Similarity NPC43345
0.9342 High Similarity NPC39154
0.9342 High Similarity NPC115601
0.9329 High Similarity NPC470132
0.9329 High Similarity NPC472629
0.9329 High Similarity NPC228779
0.9329 High Similarity NPC470131
0.9329 High Similarity NPC470134
0.9329 High Similarity NPC473078
0.9329 High Similarity NPC470133
0.9329 High Similarity NPC109183
0.9304 High Similarity NPC224851
0.9304 High Similarity NPC251336
0.9295 High Similarity NPC18380
0.9281 High Similarity NPC112701
0.9281 High Similarity NPC109594
0.9281 High Similarity NPC326592
0.9276 High Similarity NPC476552
0.9276 High Similarity NPC67322
0.9276 High Similarity NPC148945
0.9276 High Similarity NPC316960
0.9276 High Similarity NPC204561
0.9276 High Similarity NPC78835
0.9276 High Similarity NPC476553
0.9276 High Similarity NPC222713
0.9276 High Similarity NPC317715
0.9276 High Similarity NPC111112
0.9276 High Similarity NPC309512
0.9276 High Similarity NPC138299
0.9276 High Similarity NPC476551
0.9267 High Similarity NPC308200
0.9262 High Similarity NPC470890
0.9262 High Similarity NPC271288
0.9262 High Similarity NPC470136
0.9262 High Similarity NPC470135
0.9262 High Similarity NPC124780
0.9262 High Similarity NPC87486
0.9262 High Similarity NPC39045
0.9231 High Similarity NPC292863
0.9231 High Similarity NPC184326
0.9216 High Similarity NPC475790
0.9216 High Similarity NPC10807
0.9216 High Similarity NPC150123
0.9216 High Similarity NPC244583
0.9216 High Similarity NPC161881
0.9216 High Similarity NPC56232
0.9211 High Similarity NPC29777
0.9211 High Similarity NPC471115
0.9205 High Similarity NPC145467
0.9205 High Similarity NPC39195
0.9195 High Similarity NPC81697
0.9195 High Similarity NPC223812
0.9195 High Similarity NPC85162
0.9195 High Similarity NPC125894
0.9195 High Similarity NPC107177
0.9195 High Similarity NPC77794
0.9195 High Similarity NPC278249
0.9193 High Similarity NPC186847
0.9193 High Similarity NPC472454
0.9193 High Similarity NPC257667
0.9182 High Similarity NPC171985
0.9182 High Similarity NPC320741
0.9177 High Similarity NPC290160
0.9177 High Similarity NPC38591
0.9172 High Similarity NPC97812
0.9172 High Similarity NPC137232
0.9167 High Similarity NPC195167
0.9161 High Similarity NPC56049
0.9161 High Similarity NPC54830
0.9161 High Similarity NPC208152
0.9161 High Similarity NPC78492
0.9156 High Similarity NPC324447
0.9156 High Similarity NPC244250
0.9156 High Similarity NPC20907
0.915 High Similarity NPC209142
0.915 High Similarity NPC312549
0.915 High Similarity NPC474023
0.915 High Similarity NPC209846
0.915 High Similarity NPC328740
0.915 High Similarity NPC289774
0.915 High Similarity NPC477897
0.915 High Similarity NPC474021
0.9145 High Similarity NPC5173
0.9145 High Similarity NPC471114
0.9145 High Similarity NPC132345
0.9145 High Similarity NPC291746
0.9145 High Similarity NPC288840
0.9139 High Similarity NPC300988
0.9139 High Similarity NPC261271
0.9139 High Similarity NPC296998
0.9139 High Similarity NPC475348
0.9139 High Similarity NPC10990
0.9139 High Similarity NPC473077
0.9136 High Similarity NPC168789
0.9133 High Similarity NPC224714
0.9133 High Similarity NPC235217
0.9133 High Similarity NPC131579
0.9133 High Similarity NPC473013
0.9133 High Similarity NPC473015
0.9133 High Similarity NPC311144
0.9133 High Similarity NPC473014
0.9133 High Similarity NPC131568
0.9128 High Similarity NPC1089
0.9128 High Similarity NPC328164
0.9128 High Similarity NPC220998
0.9128 High Similarity NPC296917
0.9128 High Similarity NPC32739
0.9128 High Similarity NPC265040
0.9128 High Similarity NPC166482
0.9128 High Similarity NPC227579
0.9128 High Similarity NPC64915
0.9128 High Similarity NPC324436
0.9128 High Similarity NPC324134
0.9128 High Similarity NPC223500
0.9128 High Similarity NPC107572
0.9128 High Similarity NPC66515
0.9128 High Similarity NPC10937
0.9128 High Similarity NPC37496
0.9128 High Similarity NPC182852
0.9128 High Similarity NPC161506
0.9128 High Similarity NPC78
0.9128 High Similarity NPC167624
0.9128 High Similarity NPC76338
0.9128 High Similarity NPC228504
0.9128 High Similarity NPC40833
0.9128 High Similarity NPC177354
0.9128 High Similarity NPC76372
0.9128 High Similarity NPC166934
0.9128 High Similarity NPC125855
0.9128 High Similarity NPC306829
0.9128 High Similarity NPC194432
0.9128 High Similarity NPC148757
0.9119 High Similarity NPC469664
0.9097 High Similarity NPC111341

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC475184 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
0.9346 High Similarity NPD8443 Clinical (unspecified phase)
0.9295 High Similarity NPD6959 Discontinued
0.9 High Similarity NPD7852 Clinical (unspecified phase)
0.8961 High Similarity NPD4380 Phase 2
0.8903 High Similarity NPD7411 Suspended
0.8882 High Similarity NPD6167 Clinical (unspecified phase)
0.8882 High Similarity NPD4378 Clinical (unspecified phase)
0.8882 High Similarity NPD6166 Phase 2
0.8882 High Similarity NPD6168 Clinical (unspecified phase)
0.8882 High Similarity NPD7410 Clinical (unspecified phase)
0.8792 High Similarity NPD1550 Clinical (unspecified phase)
0.8792 High Similarity NPD1552 Clinical (unspecified phase)
0.879 High Similarity NPD2393 Clinical (unspecified phase)
0.8733 High Similarity NPD1549 Phase 2
0.872 High Similarity NPD7804 Clinical (unspecified phase)
0.8679 High Similarity NPD7768 Phase 2
0.8625 High Similarity NPD4381 Clinical (unspecified phase)
0.8625 High Similarity NPD7075 Discontinued
0.8553 High Similarity NPD7819 Suspended
0.8491 Intermediate Similarity NPD1934 Approved
0.8477 Intermediate Similarity NPD2796 Approved
0.8443 Intermediate Similarity NPD7074 Phase 3
0.8438 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8411 Intermediate Similarity NPD1510 Phase 2
0.8405 Intermediate Similarity NPD5494 Approved
0.8383 Intermediate Similarity NPD7054 Approved
0.8375 Intermediate Similarity NPD6801 Discontinued
0.8333 Intermediate Similarity NPD7472 Approved
0.8284 Intermediate Similarity NPD6797 Phase 2
0.8284 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8282 Intermediate Similarity NPD3749 Approved
0.8267 Intermediate Similarity NPD1240 Approved
0.8255 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD7251 Discontinued
0.8221 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8217 Intermediate Similarity NPD7390 Discontinued
0.8194 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8187 Intermediate Similarity NPD7808 Phase 3
0.8166 Intermediate Similarity NPD5844 Phase 1
0.8158 Intermediate Similarity NPD1607 Approved
0.8155 Intermediate Similarity NPD7473 Discontinued
0.814 Intermediate Similarity NPD8312 Approved
0.814 Intermediate Similarity NPD8313 Approved
0.8129 Intermediate Similarity NPD6559 Discontinued
0.8121 Intermediate Similarity NPD4908 Phase 1
0.8101 Intermediate Similarity NPD1511 Approved
0.8098 Intermediate Similarity NPD2801 Approved
0.8084 Intermediate Similarity NPD6232 Discontinued
0.8077 Intermediate Similarity NPD2800 Approved
0.8025 Intermediate Similarity NPD3750 Approved
0.8 Intermediate Similarity NPD3818 Discontinued
0.8 Intermediate Similarity NPD1512 Approved
0.7988 Intermediate Similarity NPD8455 Phase 2
0.7987 Intermediate Similarity NPD6799 Approved
0.7977 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD5403 Approved
0.7939 Intermediate Similarity NPD3817 Phase 2
0.7933 Intermediate Similarity NPD4363 Phase 3
0.7933 Intermediate Similarity NPD4360 Phase 2
0.7922 Intermediate Similarity NPD6651 Approved
0.7914 Intermediate Similarity NPD6599 Discontinued
0.7898 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7892 Intermediate Similarity NPD3882 Suspended
0.7874 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7831 Intermediate Similarity NPD5402 Approved
0.7826 Intermediate Similarity NPD2533 Approved
0.7826 Intermediate Similarity NPD2532 Approved
0.7826 Intermediate Similarity NPD2534 Approved
0.7826 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD5401 Approved
0.7821 Intermediate Similarity NPD2799 Discontinued
0.7821 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD2935 Discontinued
0.7771 Intermediate Similarity NPD1551 Phase 2
0.7759 Intermediate Similarity NPD5953 Discontinued
0.7744 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD3226 Approved
0.773 Intermediate Similarity NPD920 Approved
0.7722 Intermediate Similarity NPD2344 Approved
0.7707 Intermediate Similarity NPD3748 Approved
0.7688 Intermediate Similarity NPD4628 Phase 3
0.7658 Intermediate Similarity NPD6100 Approved
0.7658 Intermediate Similarity NPD6099 Approved
0.7651 Intermediate Similarity NPD1610 Phase 2
0.765 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD7286 Phase 2
0.7636 Intermediate Similarity NPD7458 Discontinued
0.7628 Intermediate Similarity NPD5124 Phase 1
0.7628 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD1243 Approved
0.7611 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7579 Intermediate Similarity NPD8151 Discontinued
0.7578 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD7003 Approved
0.756 Intermediate Similarity NPD1465 Phase 2
0.7558 Intermediate Similarity NPD3787 Discontinued
0.7548 Intermediate Similarity NPD2313 Discontinued
0.7545 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7533 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD2309 Approved
0.7527 Intermediate Similarity NPD6778 Approved
0.7527 Intermediate Similarity NPD6782 Approved
0.7527 Intermediate Similarity NPD6777 Approved
0.7527 Intermediate Similarity NPD6779 Approved
0.7527 Intermediate Similarity NPD6781 Approved
0.7527 Intermediate Similarity NPD6776 Approved
0.7527 Intermediate Similarity NPD6780 Approved
0.75 Intermediate Similarity NPD7698 Approved
0.75 Intermediate Similarity NPD4361 Phase 2
0.75 Intermediate Similarity NPD7697 Approved
0.75 Intermediate Similarity NPD2346 Discontinued
0.75 Intermediate Similarity NPD7696 Phase 3
0.75 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD3751 Discontinued
0.7484 Intermediate Similarity NPD7033 Discontinued
0.7469 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.746 Intermediate Similarity NPD7871 Phase 2
0.746 Intermediate Similarity NPD7870 Phase 2
0.7457 Intermediate Similarity NPD7229 Phase 3
0.7438 Intermediate Similarity NPD5406 Approved
0.7438 Intermediate Similarity NPD5405 Approved
0.7438 Intermediate Similarity NPD5408 Approved
0.7438 Intermediate Similarity NPD5404 Approved
0.7436 Intermediate Similarity NPD3268 Approved
0.7419 Intermediate Similarity NPD6832 Phase 2
0.7414 Intermediate Similarity NPD3926 Phase 2
0.7409 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7409 Intermediate Similarity NPD7783 Phase 2
0.7407 Intermediate Similarity NPD7435 Discontinued
0.7403 Intermediate Similarity NPD8150 Discontinued
0.7403 Intermediate Similarity NPD2798 Approved
0.7399 Intermediate Similarity NPD7199 Phase 2
0.7394 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7228 Approved
0.7382 Intermediate Similarity NPD7584 Approved
0.7356 Intermediate Similarity NPD5711 Approved
0.7356 Intermediate Similarity NPD5710 Approved
0.7349 Intermediate Similarity NPD6273 Approved
0.7344 Intermediate Similarity NPD7701 Phase 2
0.7342 Intermediate Similarity NPD1613 Approved
0.7342 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD1203 Approved
0.7338 Intermediate Similarity NPD2797 Approved
0.7322 Intermediate Similarity NPD4287 Approved
0.7305 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD1247 Approved
0.7294 Intermediate Similarity NPD37 Approved
0.7288 Intermediate Similarity NPD7177 Discontinued
0.7284 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD919 Approved
0.7267 Intermediate Similarity NPD1548 Phase 1
0.7267 Intermediate Similarity NPD4967 Phase 2
0.7267 Intermediate Similarity NPD4966 Approved
0.7267 Intermediate Similarity NPD4965 Approved
0.7263 Intermediate Similarity NPD6823 Phase 2
0.7261 Intermediate Similarity NPD4625 Phase 3
0.7258 Intermediate Similarity NPD6535 Approved
0.7258 Intermediate Similarity NPD6534 Approved
0.7251 Intermediate Similarity NPD5761 Phase 2
0.7251 Intermediate Similarity NPD5760 Phase 2
0.7249 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD2861 Phase 2
0.7234 Intermediate Similarity NPD7700 Phase 2
0.7234 Intermediate Similarity NPD7699 Phase 2
0.7233 Intermediate Similarity NPD943 Approved
0.7231 Intermediate Similarity NPD7801 Approved
0.7229 Intermediate Similarity NPD7212 Phase 2
0.7229 Intermediate Similarity NPD7213 Phase 3
0.7216 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD6798 Discontinued
0.7215 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD8434 Phase 2
0.7205 Intermediate Similarity NPD7097 Phase 1
0.7193 Intermediate Similarity NPD7577 Discontinued
0.7193 Intermediate Similarity NPD6844 Discontinued
0.7188 Intermediate Similarity NPD8319 Approved
0.7188 Intermediate Similarity NPD8320 Phase 1
0.7186 Intermediate Similarity NPD7447 Phase 1
0.7184 Intermediate Similarity NPD6234 Discontinued
0.7179 Intermediate Similarity NPD7874 Approved
0.7179 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD6004 Phase 3
0.7178 Intermediate Similarity NPD6005 Phase 3
0.7178 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD6002 Phase 3
0.7158 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1608 Approved
0.7143 Intermediate Similarity NPD9717 Approved
0.7134 Intermediate Similarity NPD2424 Discontinued
0.7115 Intermediate Similarity NPD3267 Approved
0.7115 Intermediate Similarity NPD3266 Approved
0.7111 Intermediate Similarity NPD1729 Discontinued
0.711 Intermediate Similarity NPD4288 Approved
0.7107 Intermediate Similarity NPD3764 Approved
0.7097 Intermediate Similarity NPD4749 Approved

Structure

External Identifiers

PubChem CID   44575248
ChEMBL   CHEMBL500482
ZINC  

Physicochemical Properties

Molecular Weight:  558.15
ALogP:  -3.8081
MLogP:  3.77
XLogP:  1.709
# Rotatable Bonds:  11
Polar Surface Area:  166.14
# H-Bond Aceptor:  2
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  41

Download Data

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