Structure

Physi-Chem Properties

Molecular Weight:  242.09
Volume:  258.799
LogP:  3.402
LogD:  3.621
LogS:  -3.007
# Rotatable Bonds:  3
TPSA:  49.69
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.812
Synthetic Accessibility Score:  2.009
Fsp3:  0.067
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.919
MDCK Permeability:  1.5398740288219415e-05
Pgp-inhibitor:  0.528
Pgp-substrate:  0.217
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.062
Plasma Protein Binding (PPB):  98.30323028564453%
Volume Distribution (VD):  1.06
Pgp-substrate:  1.2182462215423584%

ADMET: Metabolism

CYP1A2-inhibitor:  0.981
CYP1A2-substrate:  0.815
CYP2C19-inhibitor:  0.64
CYP2C19-substrate:  0.096
CYP2C9-inhibitor:  0.333
CYP2C9-substrate:  0.961
CYP2D6-inhibitor:  0.66
CYP2D6-substrate:  0.932
CYP3A4-inhibitor:  0.928
CYP3A4-substrate:  0.25

ADMET: Excretion

Clearance (CL):  12.851
Half-life (T1/2):  0.915

ADMET: Toxicity

hERG Blockers:  0.171
Human Hepatotoxicity (H-HT):  0.391
Drug-inuced Liver Injury (DILI):  0.066
AMES Toxicity:  0.158
Rat Oral Acute Toxicity:  0.072
Maximum Recommended Daily Dose:  0.641
Skin Sensitization:  0.96
Carcinogencity:  0.232
Eye Corrosion:  0.03
Eye Irritation:  0.968
Respiratory Toxicity:  0.767

Download Data

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

  Natural Product: NPC280606

Natural Product ID:  NPC280606
Common Name*:   3-[(E)-2-(4-Hydroxyphenyl)Ethenyl]-5-Methoxyphenol
IUPAC Name:   3-[(E)-2-(4-hydroxyphenyl)ethenyl]-5-methoxyphenol
Synonyms:  
Standard InCHIKey:  KUWZXOMQXYWKBS-NSCUHMNNSA-N
Standard InCHI:  InChI=1S/C15H14O3/c1-18-15-9-12(8-14(17)10-15)3-2-11-4-6-13(16)7-5-11/h2-10,16-17H,1H3/b3-2+
SMILES:  COc1cc(/C=C/c2ccc(cc2)O)cc(c1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL498917
PubChem CID:   5473050
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000253] Stilbenes

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[11520233]
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[12932145]
NPO14482 Rumex bucephalophorus Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[14510615]
NPO20812 Soymida febrifuga Species Meliaceae Eukaryota n.a. Myanmar n.a. PMID[19689125]
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20812 Soymida febrifuga Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12523 Dendrobium moniliforme Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14482 Rumex bucephalophorus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT453 Cell Line HT-1080 Homo sapiens IC50 = 89100.0 nM PMID[508014]
NPT461 Cell Line PANC-1 Homo sapiens PC50 = 71.4 uM PMID[508014]
NPT81 Cell Line A549 Homo sapiens IC50 = 91800.0 nM PMID[508014]
NPT165 Cell Line HeLa Homo sapiens IC50 = 48400.0 nM PMID[508014]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 33500.0 nM PMID[508015]
NPT492 Cell Line Caco-2 Homo sapiens IC50 = 19210.0 nM PMID[508015]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 27478.94 nM PMID[508016]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 6309.57 nM PMID[508016]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 26730.06 nM PMID[508016]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 39084.09 nM PMID[508016]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 21627.19 nM PMID[508016]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 27164.39 nM PMID[508016]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 35563.13 nM PMID[508016]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 38994.2 nM PMID[508016]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 30690.22 nM PMID[508016]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 32583.67 nM PMID[508016]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 33113.11 nM PMID[508016]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 28183.83 nM PMID[508016]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 41304.75 nM PMID[508016]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 35974.93 nM PMID[508016]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 28840.32 nM PMID[508016]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 22387.21 nM PMID[508016]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 38904.51 nM PMID[508016]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 23823.19 nM PMID[508016]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[508016]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 36643.76 nM PMID[508016]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 15958.79 nM PMID[508016]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 29376.5 nM PMID[508016]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 41975.9 nM PMID[508016]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 48752.85 nM PMID[508016]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 30060.76 nM PMID[508016]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 25351.29 nM PMID[508016]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 24322.04 nM PMID[508016]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 30974.19 nM PMID[508016]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 4073.8 nM PMID[508016]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 44565.62 nM PMID[508016]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 13551.89 nM PMID[508016]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 52722.99 nM PMID[508016]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 27669.42 nM PMID[508016]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 90364.95 nM PMID[508016]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 31988.95 nM PMID[508016]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 10115.79 nM PMID[508016]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 49090.79 nM PMID[508016]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 28444.61 nM PMID[508016]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 49203.95 nM PMID[508016]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 17988.71 nM PMID[508016]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 44668.36 nM PMID[508016]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[508016]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 44668.36 nM PMID[508016]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 20653.8 nM PMID[508016]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 31260.79 nM PMID[508016]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 33728.73 nM PMID[508016]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 25703.96 nM PMID[508016]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 53333.49 nM PMID[508016]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 44668.36 nM PMID[508016]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 40831.94 nM PMID[508016]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 29648.31 nM PMID[508016]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 24660.39 nM PMID[508016]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 40364.54 nM PMID[508016]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[508016]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[508016]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 72777.98 nM PMID[508016]
NPT1604 Individual Protein Cytochrome P450 1B1 Homo sapiens IC50 = 2100.0 nM PMID[508017]
NPT1604 Individual Protein Cytochrome P450 1B1 Homo sapiens Ki = 900.0 nM PMID[508018]
NPT1603 Individual Protein Cytochrome P450 1A1 Homo sapiens Ki = 120.0 nM PMID[508018]
NPT1603 Individual Protein Cytochrome P450 1A1 Homo sapiens Ki = 130.0 nM PMID[508020]
NPT1604 Individual Protein Cytochrome P450 1B1 Homo sapiens Ki = 900.0 nM PMID[508020]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 35800.0 nM PMID[508014]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 100000.0 nM PMID[508014]
NPT1173 Organism Candida albicans SC5314 Candida albicans SC5314 MIC95 = 300.0 ug ml-1 PMID[508019]
NPT2580 Organism Candida dubliniensis Candida dubliniensis MIC95 = 150.0 ug ml-1 PMID[508019]
NPT3676 Organism Candida famata Candida famata MIC95 = 18.0 ug ml-1 PMID[508019]
NPT554 Organism Candida glabrata Candida glabrata MIC95 = 300.0 ug ml-1 PMID[508019]
NPT2578 Organism Pichia guilliermondii Meyerozyma guilliermondii MIC95 = 150.0 ug ml-1 PMID[508019]
NPT3678 Organism Candida inconspicua Candida inconspicua MIC95 = 300.0 ug ml-1 PMID[508019]
NPT3153 Organism Kluyveromyces marxianus Kluyveromyces marxianus MIC95 = 150.0 ug ml-1 PMID[508019]
NPT187 Organism Issatchenkia orientalis Pichia kudriavzevii MIC95 = 300.0 ug ml-1 PMID[508019]
NPT820 Organism Clavispora lusitaniae Clavispora lusitaniae MIC95 = 300.0 ug ml-1 PMID[508019]
NPT3677 Organism Pichia norvegensis Pichia norvegensis MIC95 = 300.0 ug ml-1 PMID[508019]
NPT188 Organism Candida parapsilosis Candida parapsilosis MIC95 = 300.0 ug ml-1 PMID[508019]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC280606 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
0.9904 High Similarity NPC296920
0.9904 High Similarity NPC90520
0.9811 High Similarity NPC228287
0.9811 High Similarity NPC180508
0.9808 High Similarity NPC94045
0.963 High Similarity NPC203113
0.963 High Similarity NPC141090
0.9541 High Similarity NPC195466
0.9541 High Similarity NPC474933
0.9444 High Similarity NPC22610
0.9444 High Similarity NPC276737
0.9423 High Similarity NPC164576
0.9369 High Similarity NPC226629
0.9358 High Similarity NPC167934
0.9358 High Similarity NPC53906
0.9346 High Similarity NPC255068
0.934 High Similarity NPC82016
0.9273 High Similarity NPC150624
0.9231 High Similarity NPC474603
0.9231 High Similarity NPC12987
0.9204 High Similarity NPC166759
0.9204 High Similarity NPC102639
0.9189 High Similarity NPC221549
0.9189 High Similarity NPC15860
0.9189 High Similarity NPC470759
0.9189 High Similarity NPC69261
0.9189 High Similarity NPC33270
0.9189 High Similarity NPC244816
0.9189 High Similarity NPC219070
0.9189 High Similarity NPC127894
0.9189 High Similarity NPC50521
0.9182 High Similarity NPC464
0.9182 High Similarity NPC185541
0.9182 High Similarity NPC808
0.9151 High Similarity NPC35543
0.9123 High Similarity NPC476633
0.9115 High Similarity NPC232084
0.9115 High Similarity NPC61516
0.9115 High Similarity NPC474565
0.9115 High Similarity NPC247364
0.9115 High Similarity NPC10932
0.9099 High Similarity NPC54507
0.9099 High Similarity NPC114064
0.9099 High Similarity NPC85292
0.9099 High Similarity NPC229147
0.9074 High Similarity NPC168657
0.9065 High Similarity NPC245115
0.9043 High Similarity NPC71579
0.9043 High Similarity NPC473411
0.9043 High Similarity NPC262253
0.9027 High Similarity NPC184302
0.9018 High Similarity NPC259638
0.8966 High Similarity NPC282496
0.8966 High Similarity NPC136319
0.8966 High Similarity NPC84086
0.8966 High Similarity NPC233526
0.8942 High Similarity NPC248573
0.8942 High Similarity NPC161571
0.8942 High Similarity NPC275053
0.8938 High Similarity NPC131118
0.8938 High Similarity NPC190514
0.8929 High Similarity NPC193067
0.8899 High Similarity NPC303521
0.8899 High Similarity NPC2682
0.8889 High Similarity NPC75440
0.8889 High Similarity NPC270030
0.8889 High Similarity NPC206487
0.8889 High Similarity NPC5796
0.8889 High Similarity NPC138248
0.8889 High Similarity NPC228503
0.8879 High Similarity NPC41562
0.886 High Similarity NPC20674
0.8814 High Similarity NPC299584
0.8814 High Similarity NPC278955
0.8814 High Similarity NPC203133
0.8814 High Similarity NPC82483
0.8814 High Similarity NPC251855
0.8814 High Similarity NPC60885
0.8814 High Similarity NPC17943
0.8814 High Similarity NPC265483
0.8814 High Similarity NPC105031
0.8814 High Similarity NPC208950
0.8814 High Similarity NPC233410
0.8814 High Similarity NPC57490
0.8814 High Similarity NPC475169
0.8814 High Similarity NPC116907
0.8814 High Similarity NPC105925
0.8814 High Similarity NPC472093
0.8814 High Similarity NPC298757
0.8814 High Similarity NPC234400
0.8814 High Similarity NPC221077
0.8814 High Similarity NPC117214
0.8814 High Similarity NPC105718
0.8814 High Similarity NPC193544
0.8814 High Similarity NPC113495
0.8803 High Similarity NPC197757
0.8803 High Similarity NPC228922
0.8793 High Similarity NPC75713
0.8793 High Similarity NPC145780
0.8783 High Similarity NPC229401
0.8772 High Similarity NPC74821
0.8761 High Similarity NPC123948
0.875 High Similarity NPC291789
0.8739 High Similarity NPC18924
0.8739 High Similarity NPC44748
0.8739 High Similarity NPC223953
0.8739 High Similarity NPC170485
0.8739 High Similarity NPC214406
0.8739 High Similarity NPC78974
0.8739 High Similarity NPC223136
0.8739 High Similarity NPC28730
0.8739 High Similarity NPC103823
0.8718 High Similarity NPC18128
0.8718 High Similarity NPC77789
0.8696 High Similarity NPC295259
0.8692 High Similarity NPC30506
0.8667 High Similarity NPC53781
0.8667 High Similarity NPC127587
0.8667 High Similarity NPC124452
0.8667 High Similarity NPC246620
0.8667 High Similarity NPC266555
0.8667 High Similarity NPC293054
0.8667 High Similarity NPC324112
0.8667 High Similarity NPC169474
0.8667 High Similarity NPC473221
0.8667 High Similarity NPC236791
0.8667 High Similarity NPC82679
0.8667 High Similarity NPC74817
0.8667 High Similarity NPC159968
0.8667 High Similarity NPC282000
0.8667 High Similarity NPC210355
0.8649 High Similarity NPC203924
0.8644 High Similarity NPC474160
0.8644 High Similarity NPC95168
0.8636 High Similarity NPC165386
0.8632 High Similarity NPC285289
0.8632 High Similarity NPC193364
0.8621 High Similarity NPC8283
0.8621 High Similarity NPC258979
0.8621 High Similarity NPC93398
0.8611 High Similarity NPC292452
0.8598 High Similarity NPC305205
0.8595 High Similarity NPC215300
0.8595 High Similarity NPC98631
0.8595 High Similarity NPC186843
0.8595 High Similarity NPC206615
0.8595 High Similarity NPC154866
0.8595 High Similarity NPC470213
0.8595 High Similarity NPC38017
0.8583 High Similarity NPC76451
0.8583 High Similarity NPC82299
0.8571 High Similarity NPC228972
0.8571 High Similarity NPC122792
0.8559 High Similarity NPC36016
0.8559 High Similarity NPC74137
0.8559 High Similarity NPC100099
0.8545 High Similarity NPC201959
0.8534 High Similarity NPC137294
0.8534 High Similarity NPC475961
0.8534 High Similarity NPC254625
0.8534 High Similarity NPC15805
0.8534 High Similarity NPC85895
0.8532 High Similarity NPC113457
0.8525 High Similarity NPC228769
0.8525 High Similarity NPC58164
0.8525 High Similarity NPC471518
0.8525 High Similarity NPC476968
0.8525 High Similarity NPC471519
0.8525 High Similarity NPC190144
0.8525 High Similarity NPC470633
0.8525 High Similarity NPC10225
0.8525 High Similarity NPC170844
0.8512 High Similarity NPC46978
0.8505 High Similarity NPC143659
0.8505 High Similarity NPC100340
0.8496 Intermediate Similarity NPC204120
0.8487 Intermediate Similarity NPC38761
0.8487 Intermediate Similarity NPC238810
0.8487 Intermediate Similarity NPC76465
0.8487 Intermediate Similarity NPC121115
0.8475 Intermediate Similarity NPC54972
0.8475 Intermediate Similarity NPC212965
0.8475 Intermediate Similarity NPC49341
0.8462 Intermediate Similarity NPC16649
0.8455 Intermediate Similarity NPC254000
0.8455 Intermediate Similarity NPC192687
0.8455 Intermediate Similarity NPC126836
0.8455 Intermediate Similarity NPC311680
0.8455 Intermediate Similarity NPC176527
0.8455 Intermediate Similarity NPC51840
0.8455 Intermediate Similarity NPC472338
0.8455 Intermediate Similarity NPC299221
0.8455 Intermediate Similarity NPC224157
0.8455 Intermediate Similarity NPC234488
0.8455 Intermediate Similarity NPC63574
0.8448 Intermediate Similarity NPC63083
0.8443 Intermediate Similarity NPC28765
0.843 Intermediate Similarity NPC26879
0.843 Intermediate Similarity NPC50315
0.843 Intermediate Similarity NPC283049

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC280606 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
0.8942 High Similarity NPD1242 Phase 1
0.8772 High Similarity NPD1548 Phase 1
0.8632 High Similarity NPD1610 Phase 2
0.8525 High Similarity NPD3027 Phase 3
0.8333 Intermediate Similarity NPD2983 Phase 2
0.8333 Intermediate Similarity NPD2982 Phase 2
0.8293 Intermediate Similarity NPD4908 Phase 1
0.8293 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.825 Intermediate Similarity NPD2981 Phase 2
0.8211 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8175 Intermediate Similarity NPD1613 Approved
0.8175 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8167 Intermediate Similarity NPD422 Phase 1
0.816 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8158 Intermediate Similarity NPD228 Approved
0.808 Intermediate Similarity NPD4625 Phase 3
0.8065 Intermediate Similarity NPD3018 Phase 2
0.8036 Intermediate Similarity NPD968 Approved
0.8033 Intermediate Similarity NPD4749 Approved
0.8 Intermediate Similarity NPD940 Approved
0.8 Intermediate Similarity NPD846 Approved
0.7891 Intermediate Similarity NPD1240 Approved
0.784 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD2861 Phase 2
0.7778 Intermediate Similarity NPD2934 Approved
0.7778 Intermediate Similarity NPD2933 Approved
0.7769 Intermediate Similarity NPD1607 Approved
0.7742 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7734 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7734 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD5283 Phase 1
0.7706 Intermediate Similarity NPD2860 Approved
0.7706 Intermediate Similarity NPD2859 Approved
0.7672 Intermediate Similarity NPD4750 Phase 3
0.7658 Intermediate Similarity NPD3020 Approved
0.7652 Intermediate Similarity NPD1510 Phase 2
0.7596 Intermediate Similarity NPD111 Approved
0.7583 Intermediate Similarity NPD6671 Approved
0.7559 Intermediate Similarity NPD6584 Phase 3
0.7521 Intermediate Similarity NPD5451 Approved
0.752 Intermediate Similarity NPD1608 Approved
0.75 Intermediate Similarity NPD290 Approved
0.7481 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD1558 Phase 1
0.748 Intermediate Similarity NPD1357 Approved
0.7477 Intermediate Similarity NPD9295 Approved
0.7464 Intermediate Similarity NPD4357 Discontinued
0.7459 Intermediate Similarity NPD5536 Phase 2
0.7438 Intermediate Similarity NPD709 Approved
0.7436 Intermediate Similarity NPD2684 Approved
0.7407 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD3540 Phase 1
0.7407 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD1283 Approved
0.7398 Intermediate Similarity NPD1182 Approved
0.7373 Intermediate Similarity NPD3021 Approved
0.7373 Intermediate Similarity NPD3022 Approved
0.7353 Intermediate Similarity NPD1549 Phase 2
0.7348 Intermediate Similarity NPD2238 Phase 2
0.7339 Intermediate Similarity NPD1651 Approved
0.7338 Intermediate Similarity NPD1511 Approved
0.7333 Intermediate Similarity NPD821 Approved
0.7333 Intermediate Similarity NPD6100 Approved
0.7333 Intermediate Similarity NPD3539 Phase 1
0.7333 Intermediate Similarity NPD1551 Phase 2
0.7333 Intermediate Similarity NPD6099 Approved
0.7323 Intermediate Similarity NPD6583 Phase 3
0.7323 Intermediate Similarity NPD6582 Phase 2
0.7323 Intermediate Similarity NPD1669 Approved
0.7308 Intermediate Similarity NPD9089 Approved
0.7302 Intermediate Similarity NPD1091 Approved
0.7297 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD7447 Phase 1
0.728 Intermediate Similarity NPD4626 Approved
0.728 Intermediate Similarity NPD17 Approved
0.728 Intermediate Similarity NPD2667 Approved
0.728 Intermediate Similarity NPD1778 Approved
0.728 Intermediate Similarity NPD2668 Approved
0.7265 Intermediate Similarity NPD3134 Approved
0.7246 Intermediate Similarity NPD3750 Approved
0.7244 Intermediate Similarity NPD2232 Approved
0.7244 Intermediate Similarity NPD2230 Approved
0.7244 Intermediate Similarity NPD2233 Approved
0.7234 Intermediate Similarity NPD1512 Approved
0.7232 Intermediate Similarity NPD844 Approved
0.7222 Intermediate Similarity NPD3847 Discontinued
0.7218 Intermediate Similarity NPD4060 Phase 1
0.7214 Intermediate Similarity NPD7212 Phase 2
0.7214 Intermediate Similarity NPD7213 Phase 3
0.7212 Intermediate Similarity NPD9093 Approved
0.7206 Intermediate Similarity NPD2935 Discontinued
0.7203 Intermediate Similarity NPD1358 Approved
0.719 Intermediate Similarity NPD7843 Approved
0.719 Intermediate Similarity NPD5535 Approved
0.7172 Intermediate Similarity NPD1934 Approved
0.7168 Intermediate Similarity NPD288 Approved
0.7165 Intermediate Similarity NPD1535 Discovery
0.7165 Intermediate Similarity NPD1281 Approved
0.7164 Intermediate Similarity NPD230 Phase 1
0.7154 Intermediate Similarity NPD4624 Approved
0.7154 Intermediate Similarity NPD7157 Approved
0.7153 Intermediate Similarity NPD4678 Approved
0.7153 Intermediate Similarity NPD4675 Approved
0.7143 Intermediate Similarity NPD9296 Approved
0.7132 Intermediate Similarity NPD3225 Approved
0.713 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD2801 Approved
0.7123 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD3892 Phase 2
0.712 Intermediate Similarity NPD9545 Approved
0.712 Intermediate Similarity NPD1894 Discontinued
0.7111 Intermediate Similarity NPD4097 Suspended
0.7109 Intermediate Similarity NPD2235 Phase 2
0.7109 Intermediate Similarity NPD1840 Phase 2
0.7109 Intermediate Similarity NPD1481 Phase 2
0.7109 Intermediate Similarity NPD2231 Phase 2
0.7099 Intermediate Similarity NPD9494 Approved
0.708 Intermediate Similarity NPD2796 Approved
0.7071 Intermediate Similarity NPD2219 Phase 1
0.7071 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD5585 Approved
0.705 Intermediate Similarity NPD3060 Approved
0.705 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD5124 Phase 1
0.7037 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD3705 Approved
0.7027 Intermediate Similarity NPD3882 Suspended
0.7021 Intermediate Similarity NPD7124 Phase 2
0.7014 Intermediate Similarity NPD1653 Approved
0.7008 Intermediate Similarity NPD2423 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD5846 Approved
0.7008 Intermediate Similarity NPD6516 Phase 2
0.7 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6696 Suspended
0.7 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.6992 Remote Similarity NPD1241 Discontinued
0.6992 Remote Similarity NPD7095 Approved
0.6985 Remote Similarity NPD3052 Approved
0.6985 Remote Similarity NPD2568 Approved
0.6985 Remote Similarity NPD1772 Clinical (unspecified phase)
0.6985 Remote Similarity NPD3054 Approved
0.6966 Remote Similarity NPD4005 Discontinued
0.6963 Remote Similarity NPD3620 Phase 2
0.6963 Remote Similarity NPD3619 Clinical (unspecified phase)
0.696 Remote Similarity NPD3596 Phase 2
0.6953 Remote Similarity NPD3496 Discontinued
0.6947 Remote Similarity NPD1203 Approved
0.6947 Remote Similarity NPD2797 Approved
0.694 Remote Similarity NPD3145 Approved
0.694 Remote Similarity NPD3144 Approved
0.6939 Remote Similarity NPD37 Approved
0.6934 Remote Similarity NPD6111 Discontinued
0.6934 Remote Similarity NPD4536 Approved
0.6934 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6934 Remote Similarity NPD4538 Approved
0.6929 Remote Similarity NPD5691 Approved
0.6929 Remote Similarity NPD1652 Phase 2
0.6923 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5327 Phase 3
0.6918 Remote Similarity NPD4380 Phase 2
0.6917 Remote Similarity NPD600 Approved
0.6917 Remote Similarity NPD596 Approved
0.6912 Remote Similarity NPD5735 Approved
0.6909 Remote Similarity NPD9094 Approved
0.6892 Remote Similarity NPD7819 Suspended
0.6889 Remote Similarity NPD2674 Phase 3
0.6884 Remote Similarity NPD3748 Approved
0.6879 Remote Similarity NPD7466 Approved
0.6875 Remote Similarity NPD9365 Approved
0.687 Remote Similarity NPD8651 Approved
0.6853 Remote Similarity NPD6799 Approved
0.6853 Remote Similarity NPD6143 Clinical (unspecified phase)
0.685 Remote Similarity NPD6580 Approved
0.685 Remote Similarity NPD3091 Approved
0.685 Remote Similarity NPD6581 Approved
0.6846 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6842 Remote Similarity NPD4993 Discontinued
0.6838 Remote Similarity NPD3028 Approved
0.6838 Remote Similarity NPD943 Approved
0.6838 Remote Similarity NPD4140 Approved
0.6828 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6825 Remote Similarity NPD9493 Approved
0.6821 Remote Similarity NPD6234 Discontinued
0.6815 Remote Similarity NPD1296 Phase 2
0.6809 Remote Similarity NPD4237 Approved
0.6809 Remote Similarity NPD4236 Phase 3
0.6806 Remote Similarity NPD4123 Phase 3
0.6803 Remote Similarity NPD9380 Clinical (unspecified phase)
0.6803 Remote Similarity NPD1792 Phase 2
0.68 Remote Similarity NPD4868 Clinical (unspecified phase)
0.68 Remote Similarity NPD4965 Approved
0.68 Remote Similarity NPD7768 Phase 2
0.68 Remote Similarity NPD4967 Phase 2
0.68 Remote Similarity NPD4966 Approved
0.6797 Remote Similarity NPD6830 Clinical (unspecified phase)
0.6797 Remote Similarity NPD6232 Discontinued
0.6794 Remote Similarity NPD3676 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data