Natural Product: NPC299584

Natural Product ID:  NPC299584
Common Name:   Phoyunbene A
IUPAC Name:   3-[(E)-2-(3-hydroxy-5-methoxyphenyl)ethenyl]-2,6-dimethoxyphenol
Synonyms:   Phoyunbene A
Molecular Formula:   C17H18O5
Standard InCHIKey:  DYWOJJOORBDHBP-SNAWJCMRSA-N
Standard InCHI:  InChI=1S/C17H18O5/c1-20-14-9-11(8-13(18)10-14)4-5-12-6-7-15(21-2)16(19)17(12)22-3/h4-10,18-19H,1-3H3/b5-4+
Canonical SMILES:  COc1cc(/C=C/c2ccc(c(c2OC)O)OC)cc(c1)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
NPO21656 Pholidota yunnanensis Species Orchidaceae Eukaryota Whole Plants PMID[16394543]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell Line HepG2 Homo sapiens IC50 > 100000 nM 22326393
NPT2 Others Unspecified IC50 > 100000 nM 22326393

  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 NPC299584 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 NPC265483
1.0 High Similarity NPC82483
0.9916 High Similarity NPC44748
0.9916 High Similarity NPC28730
0.9916 High Similarity NPC78974
0.9916 High Similarity NPC214406
0.9916 High Similarity NPC223136
0.9916 High Similarity NPC18924
0.9916 High Similarity NPC103823
0.9833 High Similarity NPC169474
0.9833 High Similarity NPC159968
0.9833 High Similarity NPC74817
0.9833 High Similarity NPC124452
0.9833 High Similarity NPC236791
0.9833 High Similarity NPC293054
0.9833 High Similarity NPC282000
0.9833 High Similarity NPC82679
0.9833 High Similarity NPC246620
0.9833 High Similarity NPC324112
0.9832 High Similarity NPC234400
0.9832 High Similarity NPC60885
0.9831 High Similarity NPC95168
0.9746 High Similarity NPC71579
0.9746 High Similarity NPC262253
0.9746 High Similarity NPC473411
0.9672 High Similarity NPC58164
0.9672 High Similarity NPC10225
0.9667 High Similarity NPC221077
0.9667 High Similarity NPC251855
0.9667 High Similarity NPC57490
0.9667 High Similarity NPC208950
0.9667 High Similarity NPC233410
0.9667 High Similarity NPC116907
0.9667 High Similarity NPC117214
0.9667 High Similarity NPC203133
0.9667 High Similarity NPC193544
0.9667 High Similarity NPC475169
0.9667 High Similarity NPC298757
0.9667 High Similarity NPC472093
0.9667 High Similarity NPC105925
0.9667 High Similarity NPC17943
0.9661 High Similarity NPC75713
0.9593 High Similarity NPC234488
0.9593 High Similarity NPC299221
0.9593 High Similarity NPC311680
0.9593 High Similarity NPC126836
0.9593 High Similarity NPC51840
0.959 High Similarity NPC154866
0.959 High Similarity NPC28765
0.9576 High Similarity NPC166759
0.9512 High Similarity NPC212015
0.9508 High Similarity NPC252131
0.9508 High Similarity NPC266555
0.9508 High Similarity NPC210355
0.9508 High Similarity NPC236760
0.9508 High Similarity NPC127587
0.95 High Similarity NPC282496
0.95 High Similarity NPC197757
0.95 High Similarity NPC136319
0.95 High Similarity NPC121115
0.95 High Similarity NPC228922
0.95 High Similarity NPC233526
0.9492 High Similarity NPC247364
0.9492 High Similarity NPC474565
0.9492 High Similarity NPC232084
0.9492 High Similarity NPC61516
0.9492 High Similarity NPC10932
0.944 High Similarity NPC6451
0.9435 High Similarity NPC214860
0.9431 High Similarity NPC98631
0.9431 High Similarity NPC206615
0.9431 High Similarity NPC186843
0.9431 High Similarity NPC266691
0.9431 High Similarity NPC470213
0.9426 High Similarity NPC223953
0.9426 High Similarity NPC76451
0.9421 High Similarity NPC183446
0.9417 High Similarity NPC41562
0.9407 High Similarity NPC226629
0.9365 High Similarity NPC471391
0.9365 High Similarity NPC475840
0.9365 High Similarity NPC471390
0.9365 High Similarity NPC229442
0.9365 High Similarity NPC168059
0.9365 High Similarity NPC32778
0.9365 High Similarity NPC36661
0.936 High Similarity NPC12275
0.936 High Similarity NPC232275
0.936 High Similarity NPC474356
0.936 High Similarity NPC45715
0.9355 High Similarity NPC476968
0.9355 High Similarity NPC45824
0.9355 High Similarity NPC170844
0.9291 High Similarity NPC317380
0.9286 High Similarity NPC86655
0.9286 High Similarity NPC202762
0.9286 High Similarity NPC127624
0.928 High Similarity NPC91291
0.928 High Similarity NPC192687
0.928 High Similarity NPC224157
0.928 High Similarity NPC472338
0.9262 High Similarity NPC228972
0.9262 High Similarity NPC122792
0.9262 High Similarity NPC5796
0.9262 High Similarity NPC206487
0.9244 High Similarity NPC20674
0.9237 High Similarity NPC259638
0.9219 High Similarity NPC108198
0.9219 High Similarity NPC474206
0.9219 High Similarity NPC158142
0.9219 High Similarity NPC472337
0.9219 High Similarity NPC94750
0.9219 High Similarity NPC69029
0.9219 High Similarity NPC200557
0.9219 High Similarity NPC121812
0.9219 High Similarity NPC313081
0.9219 High Similarity NPC112246
0.9219 High Similarity NPC10314
0.9219 High Similarity NPC256262
0.9219 High Similarity NPC294884
0.9219 High Similarity NPC112939
0.9219 High Similarity NPC470356
0.9206 High Similarity NPC472597
0.9206 High Similarity NPC474017
0.9206 High Similarity NPC470096
0.9206 High Similarity NPC15543
0.9206 High Similarity NPC470095
0.92 High Similarity NPC470633
0.92 High Similarity NPC469963
0.92 High Similarity NPC228769
0.92 High Similarity NPC190144
0.92 High Similarity NPC469951
0.9194 High Similarity NPC216836
0.9194 High Similarity NPC242032
0.9194 High Similarity NPC470699
0.918 High Similarity NPC84086
0.9174 High Similarity NPC145780
0.9174 High Similarity NPC49341
0.9167 High Similarity NPC229401
0.9153 High Similarity NPC203113
0.9153 High Similarity NPC123948
0.9153 High Similarity NPC193067
0.9147 High Similarity NPC143139
0.9147 High Similarity NPC202846
0.9147 High Similarity NPC16435
0.9147 High Similarity NPC248727
0.9147 High Similarity NPC265433
0.9147 High Similarity NPC270456
0.9147 High Similarity NPC227503
0.9147 High Similarity NPC230734
0.9147 High Similarity NPC474639
0.9147 High Similarity NPC306441
0.9147 High Similarity NPC472334
0.9147 High Similarity NPC162659
0.9147 High Similarity NPC472336
0.9141 High Similarity NPC289258
0.9141 High Similarity NPC276026
0.9141 High Similarity NPC206737
0.9141 High Similarity NPC56764
0.9141 High Similarity NPC209199
0.9141 High Similarity NPC125649
0.9141 High Similarity NPC469659
0.9141 High Similarity NPC555
0.9141 High Similarity NPC7515
0.9141 High Similarity NPC188378
0.9134 High Similarity NPC160991
0.9134 High Similarity NPC16208
0.9134 High Similarity NPC184447
0.9134 High Similarity NPC7903
0.9134 High Similarity NPC201587
0.9134 High Similarity NPC35932
0.9134 High Similarity NPC253105
0.9127 High Similarity NPC474481
0.9113 High Similarity NPC181361
0.9113 High Similarity NPC112596
0.9083 High Similarity NPC475961
0.9083 High Similarity NPC254625
0.9077 High Similarity NPC6262
0.9077 High Similarity NPC107551
0.9077 High Similarity NPC276490
0.9077 High Similarity NPC211549
0.9077 High Similarity NPC474282
0.9077 High Similarity NPC326797
0.9077 High Similarity NPC102904
0.9077 High Similarity NPC90615
0.9077 High Similarity NPC176051
0.9077 High Similarity NPC73535
0.9077 High Similarity NPC103976
0.9077 High Similarity NPC272157
0.9077 High Similarity NPC56329
0.9077 High Similarity NPC242715
0.9077 High Similarity NPC201145
0.9077 High Similarity NPC25111
0.907 High Similarity NPC180602
0.907 High Similarity NPC241241
0.907 High Similarity NPC214853
0.907 High Similarity NPC234333
0.907 High Similarity NPC61946
0.907 High Similarity NPC55239
0.907 High Similarity NPC47398

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC299584 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
0.9355 High Similarity NPD3027 Phase 3
0.8968 High Similarity NPD1529 Clinical (unspecified phase)
0.8889 High Similarity NPD1530 Clinical (unspecified phase)
0.8889 High Similarity NPD3018 Phase 2
0.8837 High Similarity NPD1613 Approved
0.8837 High Similarity NPD1612 Clinical (unspecified phase)
0.872 High Similarity NPD2983 Phase 2
0.872 High Similarity NPD2982 Phase 2
0.864 High Similarity NPD2981 Phase 2
0.8571 High Similarity NPD228 Approved
0.8425 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.8279 Intermediate Similarity NPD5283 Phase 1
0.8244 Intermediate Similarity NPD4908 Phase 1
0.824 Intermediate Similarity NPD1548 Phase 1
0.8175 Intermediate Similarity NPD3540 Phase 1
0.8125 Intermediate Similarity NPD1610 Phase 2
0.812 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8102 Intermediate Similarity NPD3539 Phase 1
0.8082 Intermediate Similarity NPD2801 Approved
0.8014 Intermediate Similarity NPD1934 Approved
0.7973 Intermediate Similarity NPD3882 Suspended
0.7951 Intermediate Similarity NPD3021 Approved
0.7951 Intermediate Similarity NPD3022 Approved
0.791 Intermediate Similarity NPD4625 Phase 3
0.7881 Intermediate Similarity NPD1242 Phase 1
0.7874 Intermediate Similarity NPD5536 Phase 2
0.7868 Intermediate Similarity NPD1558 Phase 1
0.7863 Intermediate Similarity NPD4749 Approved
0.7862 Intermediate Similarity NPD1653 Approved
0.7838 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7832 Intermediate Similarity NPD4357 Discontinued
0.7832 Intermediate Similarity NPD1511 Approved
0.7727 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD1512 Approved
0.7721 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.771 Intermediate Similarity NPD422 Phase 1
0.7687 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD846 Approved
0.7667 Intermediate Similarity NPD940 Approved
0.7635 Intermediate Similarity NPD4678 Approved
0.7635 Intermediate Similarity NPD4675 Approved
0.7632 Intermediate Similarity NPD6234 Discontinued
0.763 Intermediate Similarity NPD2861 Phase 2
0.7616 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7615 Intermediate Similarity NPD1357 Approved
0.7613 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD6166 Phase 2
0.7613 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD3620 Phase 2
0.7609 Intermediate Similarity NPD4060 Phase 1
0.7609 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7591 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD3705 Approved
0.7576 Intermediate Similarity NPD1091 Approved
0.7569 Intermediate Similarity NPD2219 Phase 1
0.7569 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7552 Intermediate Similarity NPD3060 Approved
0.755 Intermediate Similarity NPD3817 Phase 2
0.7537 Intermediate Similarity NPD2922 Phase 1
0.7536 Intermediate Similarity NPD2674 Phase 3
0.7533 Intermediate Similarity NPD37 Approved
0.752 Intermediate Similarity NPD4750 Phase 3
0.7517 Intermediate Similarity NPD7124 Phase 2
0.75 Intermediate Similarity NPD290 Approved
0.7484 Intermediate Similarity NPD6232 Discontinued
0.7482 Intermediate Similarity NPD1240 Approved
0.7468 Intermediate Similarity NPD7054 Approved
0.7464 Intermediate Similarity NPD3144 Approved
0.7464 Intermediate Similarity NPD3145 Approved
0.7458 Intermediate Similarity NPD9296 Approved
0.7451 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD4005 Discontinued
0.7442 Intermediate Similarity NPD6671 Approved
0.744 Intermediate Similarity NPD2684 Approved
0.7429 Intermediate Similarity NPD230 Phase 1
0.7421 Intermediate Similarity NPD7074 Phase 3
0.7421 Intermediate Similarity NPD7472 Approved
0.7419 Intermediate Similarity NPD7199 Phase 2
0.7413 Intermediate Similarity NPD7266 Discontinued
0.7405 Intermediate Similarity NPD3818 Discontinued
0.7394 Intermediate Similarity NPD1510 Phase 2
0.7386 Intermediate Similarity NPD4966 Approved
0.7386 Intermediate Similarity NPD4965 Approved
0.7386 Intermediate Similarity NPD4967 Phase 2
0.7376 Intermediate Similarity NPD1607 Approved
0.7372 Intermediate Similarity NPD9494 Approved
0.7365 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD943 Approved
0.7347 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7344 Intermediate Similarity NPD7843 Approved
0.7342 Intermediate Similarity NPD7473 Discontinued
0.7338 Intermediate Similarity NPD4055 Discovery
0.7325 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD6111 Discontinued
0.7315 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD2934 Approved
0.7311 Intermediate Similarity NPD2933 Approved
0.731 Intermediate Similarity NPD4236 Phase 3
0.731 Intermediate Similarity NPD5177 Phase 3
0.731 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD4237 Approved
0.7308 Intermediate Similarity NPD7157 Approved
0.7297 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD4123 Phase 3
0.7297 Intermediate Similarity NPD7447 Phase 1
0.7296 Intermediate Similarity NPD7228 Approved
0.7292 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD4380 Phase 2
0.728 Intermediate Similarity NPD968 Approved
0.7279 Intermediate Similarity NPD8651 Approved
0.7267 Intermediate Similarity NPD6797 Phase 2
0.7255 Intermediate Similarity NPD1465 Phase 2
0.725 Intermediate Similarity NPD2859 Approved
0.725 Intermediate Similarity NPD2860 Approved
0.7241 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD7213 Phase 3
0.723 Intermediate Similarity NPD7212 Phase 2
0.723 Intermediate Similarity NPD6799 Approved
0.7222 Intermediate Similarity NPD2935 Discontinued
0.7222 Intermediate Similarity NPD6100 Approved
0.7222 Intermediate Similarity NPD7251 Discontinued
0.7222 Intermediate Similarity NPD6099 Approved
0.7214 Intermediate Similarity NPD5109 Approved
0.7214 Intermediate Similarity NPD5110 Phase 2
0.7214 Intermediate Similarity NPD5111 Phase 2
0.7213 Intermediate Similarity NPD3020 Approved
0.7211 Intermediate Similarity NPD6190 Approved
0.7195 Intermediate Similarity NPD8053 Approved
0.7195 Intermediate Similarity NPD8054 Approved
0.7194 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD1652 Phase 2
0.7192 Intermediate Similarity NPD6674 Discontinued
0.7181 Intermediate Similarity NPD1424 Approved
0.7178 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD7808 Phase 3
0.7174 Intermediate Similarity NPD6584 Phase 3
0.7172 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD4626 Approved
0.7143 Intermediate Similarity NPD2978 Approved
0.7143 Intermediate Similarity NPD3892 Phase 2
0.7143 Intermediate Similarity NPD2977 Approved
0.7143 Intermediate Similarity NPD7095 Approved
0.7143 Intermediate Similarity NPD3750 Approved
0.7143 Intermediate Similarity NPD5844 Phase 1
0.7124 Intermediate Similarity NPD5090 Approved
0.7124 Intermediate Similarity NPD5089 Approved
0.7123 Intermediate Similarity NPD1549 Phase 2
0.7115 Intermediate Similarity NPD7075 Discontinued
0.7114 Intermediate Similarity NPD5297 Approved
0.7113 Intermediate Similarity NPD2238 Phase 2
0.7109 Intermediate Similarity NPD5451 Approved
0.7105 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD1551 Phase 2
0.7097 Intermediate Similarity NPD291 Approved
0.7097 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD2677 Approved
0.7092 Intermediate Similarity NPD6798 Discontinued
0.7092 Intermediate Similarity NPD5718 Phase 2
0.7083 Intermediate Similarity NPD4536 Approved
0.7083 Intermediate Similarity NPD4538 Approved
0.7083 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD4162 Approved
0.7063 Intermediate Similarity NPD6355 Discontinued
0.7063 Intermediate Similarity NPD5124 Phase 1
0.7063 Intermediate Similarity NPD447 Suspended
0.7063 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD6788 Approved
0.7045 Intermediate Similarity NPD709 Approved
0.7037 Intermediate Similarity NPD6516 Phase 2
0.7037 Intermediate Similarity NPD5846 Approved
0.7037 Intermediate Similarity NPD1778 Approved
0.7034 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD3225 Approved
0.7027 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD5494 Approved
0.702 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD4097 Suspended
0.7007 Intermediate Similarity NPD2233 Approved
0.7007 Intermediate Similarity NPD2230 Approved
0.7007 Intermediate Similarity NPD2232 Approved
0.7006 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.6993 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6986 Remote Similarity NPD2796 Approved
0.6985 Remote Similarity NPD3496 Discontinued
0.6985 Remote Similarity NPD3847 Discontinued
0.698 Remote Similarity NPD5241 Discontinued
0.697 Remote Similarity NPD7549 Discontinued
0.6967 Remote Similarity NPD844 Approved
0.6966 Remote Similarity NPD6896 Approved
0.6966 Remote Similarity NPD6895 Approved
0.6957 Remote Similarity NPD6583 Phase 3
0.6957 Remote Similarity NPD6582 Phase 2
0.6954 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6953 Remote Similarity NPD1358 Approved
0.6949 Remote Similarity NPD9094 Approved

Structure

External Identifiers

PubChem CID   11522311
ChEMBL   CHEMBL2012416
ZINC  

Physicochemical Properties

Molecular Weight:  302.12
ALogP:  -0.6082
MLogP:  2.78
XLogP:  2.645
# Rotatable Bonds:  10
Polar Surface Area:  68.15
# H-Bond Aceptor:  0
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  22

Download Data

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