Natural Product: NPC95168

Natural Product ID:  NPC95168
Common Name:   Phoyunbene C
IUPAC Name:   3-[(E)-2-(3-hydroxy-5-methoxyphenyl)ethenyl]-2-methoxyphenol
Synonyms:   Phoyunbene C
Molecular Formula:   C16H16O4
Standard InCHIKey:  NYSXLCHSDQNVBS-VOTSOKGWSA-N
Standard InCHI:  InChI=1S/C16H16O4/c1-19-14-9-11(8-13(17)10-14)6-7-12-4-3-5-15(18)16(12)20-2/h3-10,17-18H,1-2H3/b7-6+
Canonical SMILES:  COc1cc(/C=C/c2cccc(c2OC)O)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]
NPO21656 Pholidota yunnanensis Species Orchidaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell Line HepG2 Homo sapiens IC50 = 90800 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 NPC95168 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
0.9831 High Similarity NPC265483
0.9831 High Similarity NPC82483
0.9831 High Similarity NPC299584
0.9828 High Similarity NPC75713
0.9748 High Similarity NPC223136
0.9748 High Similarity NPC214406
0.9748 High Similarity NPC44748
0.9748 High Similarity NPC28730
0.9748 High Similarity NPC103823
0.9748 High Similarity NPC18924
0.9748 High Similarity NPC78974
0.9667 High Similarity NPC293054
0.9667 High Similarity NPC324112
0.9667 High Similarity NPC124452
0.9667 High Similarity NPC82679
0.9667 High Similarity NPC159968
0.9667 High Similarity NPC236791
0.9667 High Similarity NPC246620
0.9667 High Similarity NPC169474
0.9667 High Similarity NPC282000
0.9667 High Similarity NPC74817
0.9667 High Similarity NPC236760
0.9664 High Similarity NPC234400
0.9664 High Similarity NPC60885
0.9661 High Similarity NPC121115
0.9587 High Similarity NPC266691
0.9576 High Similarity NPC473411
0.9576 High Similarity NPC262253
0.9576 High Similarity NPC71579
0.9508 High Similarity NPC58164
0.9508 High Similarity NPC10225
0.95 High Similarity NPC17943
0.95 High Similarity NPC57490
0.95 High Similarity NPC203133
0.95 High Similarity NPC298757
0.95 High Similarity NPC105925
0.95 High Similarity NPC475169
0.95 High Similarity NPC193544
0.95 High Similarity NPC233410
0.95 High Similarity NPC221077
0.95 High Similarity NPC251855
0.95 High Similarity NPC117214
0.95 High Similarity NPC208950
0.95 High Similarity NPC116907
0.95 High Similarity NPC472093
0.9431 High Similarity NPC299221
0.9431 High Similarity NPC126836
0.9431 High Similarity NPC234488
0.9431 High Similarity NPC51840
0.9431 High Similarity NPC311680
0.9426 High Similarity NPC28765
0.9426 High Similarity NPC154866
0.9407 High Similarity NPC166759
0.935 High Similarity NPC212015
0.9344 High Similarity NPC210355
0.9344 High Similarity NPC266555
0.9344 High Similarity NPC252131
0.9344 High Similarity NPC127587
0.9344 High Similarity NPC216836
0.9333 High Similarity NPC233526
0.9333 High Similarity NPC136319
0.9333 High Similarity NPC282496
0.9333 High Similarity NPC197757
0.9333 High Similarity NPC228922
0.9322 High Similarity NPC474565
0.9322 High Similarity NPC61516
0.9322 High Similarity NPC10932
0.9322 High Similarity NPC247364
0.9322 High Similarity NPC232084
0.928 High Similarity NPC6451
0.9274 High Similarity NPC214860
0.9268 High Similarity NPC470213
0.9268 High Similarity NPC186843
0.9268 High Similarity NPC98631
0.9268 High Similarity NPC206615
0.9262 High Similarity NPC112596
0.9262 High Similarity NPC223953
0.9262 High Similarity NPC76451
0.9256 High Similarity NPC183446
0.925 High Similarity NPC41562
0.9237 High Similarity NPC226629
0.9206 High Similarity NPC471391
0.9206 High Similarity NPC32778
0.9206 High Similarity NPC37196
0.9206 High Similarity NPC36661
0.9206 High Similarity NPC475840
0.9206 High Similarity NPC229442
0.9206 High Similarity NPC94236
0.9206 High Similarity NPC168059
0.9206 High Similarity NPC471390
0.92 High Similarity NPC12275
0.92 High Similarity NPC45715
0.92 High Similarity NPC232275
0.92 High Similarity NPC474356
0.9194 High Similarity NPC170844
0.9194 High Similarity NPC476968
0.9194 High Similarity NPC45824
0.9134 High Similarity NPC317380
0.9127 High Similarity NPC86655
0.9127 High Similarity NPC161203
0.9127 High Similarity NPC202762
0.9127 High Similarity NPC127624
0.912 High Similarity NPC224157
0.912 High Similarity NPC472338
0.912 High Similarity NPC91291
0.912 High Similarity NPC192687
0.9098 High Similarity NPC228972
0.9098 High Similarity NPC122792
0.9098 High Similarity NPC206487
0.9098 High Similarity NPC5796
0.9091 High Similarity NPC135414
0.9091 High Similarity NPC474864
0.9091 High Similarity NPC246967
0.9076 High Similarity NPC20674
0.9068 High Similarity NPC69261
0.9068 High Similarity NPC33270
0.9068 High Similarity NPC259638
0.9062 High Similarity NPC470356
0.9062 High Similarity NPC94750
0.9062 High Similarity NPC474206
0.9062 High Similarity NPC281521
0.9062 High Similarity NPC294884
0.9062 High Similarity NPC200557
0.9062 High Similarity NPC112246
0.9062 High Similarity NPC201357
0.9062 High Similarity NPC283009
0.9062 High Similarity NPC255147
0.9062 High Similarity NPC108198
0.9062 High Similarity NPC121812
0.9062 High Similarity NPC134968
0.9062 High Similarity NPC261873
0.9062 High Similarity NPC158142
0.9062 High Similarity NPC69029
0.9062 High Similarity NPC472337
0.9062 High Similarity NPC256262
0.9062 High Similarity NPC313081
0.9062 High Similarity NPC112939
0.9062 High Similarity NPC10314
0.9048 High Similarity NPC15543
0.9048 High Similarity NPC474017
0.9048 High Similarity NPC470096
0.9048 High Similarity NPC470095
0.9048 High Similarity NPC472597
0.904 High Similarity NPC469963
0.904 High Similarity NPC470633
0.904 High Similarity NPC469951
0.904 High Similarity NPC228769
0.904 High Similarity NPC190144
0.9032 High Similarity NPC242032
0.9032 High Similarity NPC470699
0.9016 High Similarity NPC84086
0.9008 High Similarity NPC145780
0.9008 High Similarity NPC49341
0.9 High Similarity NPC229401
0.8992 High Similarity NPC472334
0.8992 High Similarity NPC248727
0.8992 High Similarity NPC227503
0.8992 High Similarity NPC202846
0.8992 High Similarity NPC16435
0.8992 High Similarity NPC162659
0.8992 High Similarity NPC306441
0.8992 High Similarity NPC474639
0.8992 High Similarity NPC230734
0.8992 High Similarity NPC143139
0.8992 High Similarity NPC270456
0.8992 High Similarity NPC265433
0.8992 High Similarity NPC472336
0.8984 High Similarity NPC555
0.8984 High Similarity NPC209199
0.8984 High Similarity NPC103967
0.8984 High Similarity NPC56764
0.8984 High Similarity NPC469659
0.8984 High Similarity NPC125649
0.8984 High Similarity NPC276026
0.8984 High Similarity NPC289258
0.8984 High Similarity NPC188378
0.8984 High Similarity NPC206737
0.8984 High Similarity NPC7515
0.8983 High Similarity NPC193067
0.8983 High Similarity NPC150624
0.8983 High Similarity NPC123948
0.8983 High Similarity NPC203113
0.8976 High Similarity NPC16208
0.8976 High Similarity NPC201587
0.8976 High Similarity NPC253105
0.8976 High Similarity NPC7903
0.8976 High Similarity NPC184447
0.8976 High Similarity NPC35932
0.8976 High Similarity NPC160991
0.8968 High Similarity NPC229231
0.8968 High Similarity NPC220935
0.8968 High Similarity NPC474481
0.8952 High Similarity NPC181361
0.8923 High Similarity NPC242715
0.8923 High Similarity NPC276490
0.8923 High Similarity NPC25111
0.8923 High Similarity NPC73535
0.8923 High Similarity NPC272157
0.8923 High Similarity NPC90615
0.8923 High Similarity NPC474282

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC95168 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
0.9194 High Similarity NPD3027 Phase 3
0.881 High Similarity NPD1529 Clinical (unspecified phase)
0.873 High Similarity NPD3018 Phase 2
0.873 High Similarity NPD1530 Clinical (unspecified phase)
0.8682 High Similarity NPD1613 Approved
0.8682 High Similarity NPD1612 Clinical (unspecified phase)
0.856 High Similarity NPD2982 Phase 2
0.856 High Similarity NPD2983 Phase 2
0.848 Intermediate Similarity NPD2981 Phase 2
0.8403 Intermediate Similarity NPD228 Approved
0.8268 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.8115 Intermediate Similarity NPD5283 Phase 1
0.8092 Intermediate Similarity NPD4908 Phase 1
0.808 Intermediate Similarity NPD1548 Phase 1
0.803 Intermediate Similarity NPD4625 Phase 3
0.8029 Intermediate Similarity NPD3540 Phase 1
0.7984 Intermediate Similarity NPD4749 Approved
0.797 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7969 Intermediate Similarity NPD1610 Phase 2
0.7956 Intermediate Similarity NPD3539 Phase 1
0.7945 Intermediate Similarity NPD2801 Approved
0.7877 Intermediate Similarity NPD1934 Approved
0.7838 Intermediate Similarity NPD3882 Suspended
0.7803 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7787 Intermediate Similarity NPD3022 Approved
0.7787 Intermediate Similarity NPD3021 Approved
0.7724 Intermediate Similarity NPD1653 Approved
0.7721 Intermediate Similarity NPD1558 Phase 1
0.7717 Intermediate Similarity NPD5536 Phase 2
0.7712 Intermediate Similarity NPD1242 Phase 1
0.7704 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7703 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD1511 Approved
0.7692 Intermediate Similarity NPD4357 Discontinued
0.7692 Intermediate Similarity NPD1091 Approved
0.7652 Intermediate Similarity NPD2922 Phase 1
0.7642 Intermediate Similarity NPD4750 Phase 3
0.7623 Intermediate Similarity NPD290 Approved
0.7586 Intermediate Similarity NPD1512 Approved
0.7586 Intermediate Similarity NPD9296 Approved
0.7576 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7559 Intermediate Similarity NPD6671 Approved
0.7557 Intermediate Similarity NPD422 Phase 1
0.75 Intermediate Similarity NPD4675 Approved
0.75 Intermediate Similarity NPD6234 Discontinued
0.75 Intermediate Similarity NPD4678 Approved
0.75 Intermediate Similarity NPD940 Approved
0.75 Intermediate Similarity NPD846 Approved
0.7484 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD6166 Phase 2
0.7483 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD2861 Phase 2
0.7464 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD4060 Phase 1
0.7464 Intermediate Similarity NPD3620 Phase 2
0.7462 Intermediate Similarity NPD1357 Approved
0.7431 Intermediate Similarity NPD2219 Phase 1
0.7431 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD3705 Approved
0.7417 Intermediate Similarity NPD3817 Phase 2
0.7413 Intermediate Similarity NPD5177 Phase 3
0.7413 Intermediate Similarity NPD3060 Approved
0.74 Intermediate Similarity NPD37 Approved
0.7398 Intermediate Similarity NPD968 Approved
0.7391 Intermediate Similarity NPD2674 Phase 3
0.7379 Intermediate Similarity NPD7124 Phase 2
0.7355 Intermediate Similarity NPD6232 Discontinued
0.7342 Intermediate Similarity NPD7054 Approved
0.7338 Intermediate Similarity NPD1240 Approved
0.7324 Intermediate Similarity NPD6099 Approved
0.7324 Intermediate Similarity NPD6100 Approved
0.732 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD3144 Approved
0.7319 Intermediate Similarity NPD3145 Approved
0.7315 Intermediate Similarity NPD4005 Discontinued
0.7296 Intermediate Similarity NPD7472 Approved
0.7296 Intermediate Similarity NPD7074 Phase 3
0.729 Intermediate Similarity NPD7199 Phase 2
0.7286 Intermediate Similarity NPD230 Phase 1
0.728 Intermediate Similarity NPD2684 Approved
0.7278 Intermediate Similarity NPD3818 Discontinued
0.7273 Intermediate Similarity NPD7266 Discontinued
0.7255 Intermediate Similarity NPD4966 Approved
0.7255 Intermediate Similarity NPD4965 Approved
0.7255 Intermediate Similarity NPD4967 Phase 2
0.7254 Intermediate Similarity NPD1510 Phase 2
0.7241 Intermediate Similarity NPD3892 Phase 2
0.7234 Intermediate Similarity NPD1607 Approved
0.723 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD9494 Approved
0.7215 Intermediate Similarity NPD7473 Discontinued
0.7214 Intermediate Similarity NPD943 Approved
0.7213 Intermediate Similarity NPD291 Approved
0.7211 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD4055 Discovery
0.7203 Intermediate Similarity NPD1551 Phase 2
0.7197 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD7843 Approved
0.7183 Intermediate Similarity NPD6111 Discontinued
0.7181 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD4237 Approved
0.7172 Intermediate Similarity NPD4236 Phase 3
0.7172 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD7228 Approved
0.7163 Intermediate Similarity NPD447 Suspended
0.7162 Intermediate Similarity NPD4123 Phase 3
0.7162 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD7447 Phase 1
0.7154 Intermediate Similarity NPD7157 Approved
0.7154 Intermediate Similarity NPD709 Approved
0.7153 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD4380 Phase 2
0.7143 Intermediate Similarity NPD6797 Phase 2
0.7143 Intermediate Similarity NPD1778 Approved
0.7143 Intermediate Similarity NPD2934 Approved
0.7143 Intermediate Similarity NPD2933 Approved
0.7132 Intermediate Similarity NPD8651 Approved
0.7132 Intermediate Similarity NPD3225 Approved
0.7124 Intermediate Similarity NPD1465 Phase 2
0.7123 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD2232 Approved
0.7111 Intermediate Similarity NPD2233 Approved
0.7111 Intermediate Similarity NPD2230 Approved
0.7103 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD7251 Discontinued
0.7095 Intermediate Similarity NPD6799 Approved
0.7095 Intermediate Similarity NPD7212 Phase 2
0.7095 Intermediate Similarity NPD7213 Phase 3
0.7092 Intermediate Similarity NPD2238 Phase 2
0.709 Intermediate Similarity NPD3496 Discontinued
0.7083 Intermediate Similarity NPD2860 Approved
0.7083 Intermediate Similarity NPD844 Approved
0.7083 Intermediate Similarity NPD2935 Discontinued
0.7083 Intermediate Similarity NPD2859 Approved
0.7075 Intermediate Similarity NPD6190 Approved
0.7075 Intermediate Similarity NPD2677 Approved
0.7073 Intermediate Similarity NPD8053 Approved
0.7073 Intermediate Similarity NPD8054 Approved
0.7071 Intermediate Similarity NPD5111 Phase 2
0.7071 Intermediate Similarity NPD5109 Approved
0.7071 Intermediate Similarity NPD5110 Phase 2
0.7069 Intermediate Similarity NPD9094 Approved
0.7055 Intermediate Similarity NPD1652 Phase 2
0.7055 Intermediate Similarity NPD7808 Phase 3
0.7055 Intermediate Similarity NPD6674 Discontinued
0.7055 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD3020 Approved
0.7047 Intermediate Similarity NPD1424 Approved
0.7034 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD5763 Approved
0.7034 Intermediate Similarity NPD5762 Approved
0.7034 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD6584 Phase 3
0.7019 Intermediate Similarity NPD5844 Phase 1
0.7015 Intermediate Similarity NPD4626 Approved
0.7013 Intermediate Similarity NPD2978 Approved
0.7013 Intermediate Similarity NPD2977 Approved
0.7007 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD3750 Approved
0.7007 Intermediate Similarity NPD6696 Suspended
0.7 Intermediate Similarity NPD7095 Approved
0.6993 Remote Similarity NPD5089 Approved
0.6993 Remote Similarity NPD5090 Approved
0.6987 Remote Similarity NPD7075 Discontinued
0.6986 Remote Similarity NPD1549 Phase 2
0.6985 Remote Similarity NPD1608 Approved
0.698 Remote Similarity NPD5297 Approved
0.698 Remote Similarity NPD1774 Approved
0.6974 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6968 Remote Similarity NPD5402 Approved
0.6957 Remote Similarity NPD2797 Approved
0.6954 Remote Similarity NPD5403 Approved
0.6953 Remote Similarity NPD5451 Approved
0.695 Remote Similarity NPD5718 Phase 2
0.695 Remote Similarity NPD6798 Discontinued
0.6944 Remote Similarity NPD4536 Approved
0.6944 Remote Similarity NPD4538 Approved
0.6944 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6939 Remote Similarity NPD4162 Approved
0.6933 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6933 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5124 Phase 1
0.6923 Remote Similarity NPD6788 Approved
0.6923 Remote Similarity NPD1933 Approved
0.6923 Remote Similarity NPD6355 Discontinued
0.6917 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6899 Remote Similarity NPD5494 Approved
0.6899 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6897 Remote Similarity NPD7033 Discontinued
0.6897 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6889 Remote Similarity NPD5846 Approved
0.6889 Remote Similarity NPD6516 Phase 2
0.6887 Remote Similarity NPD5261 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   11507326
ChEMBL   CHEMBL2012418
ZINC  

Physicochemical Properties

Molecular Weight:  272.10
ALogP:  -0.5564
MLogP:  2.78
XLogP:  3.089
# Rotatable Bonds:  8
Polar Surface Area:  58.92
# H-Bond Aceptor:  0
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  20

Download Data

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