Structure

Physi-Chem Properties

Molecular Weight:  252.1
Volume:  255.617
LogP:  1.854
LogD:  2.363
LogS:  -2.964
# Rotatable Bonds:  6
TPSA:  53.99
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.591
Synthetic Accessibility Score:  1.913
Fsp3:  0.308
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.528
MDCK Permeability:  1.9477218302199617e-05
Pgp-inhibitor:  0.876
Pgp-substrate:  0.847
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.31

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.959
Plasma Protein Binding (PPB):  57.01764678955078%
Volume Distribution (VD):  0.531
Pgp-substrate:  15.051349639892578%

ADMET: Metabolism

CYP1A2-inhibitor:  0.948
CYP1A2-substrate:  0.953
CYP2C19-inhibitor:  0.379
CYP2C19-substrate:  0.892
CYP2C9-inhibitor:  0.078
CYP2C9-substrate:  0.866
CYP2D6-inhibitor:  0.05
CYP2D6-substrate:  0.779
CYP3A4-inhibitor:  0.261
CYP3A4-substrate:  0.537

ADMET: Excretion

Clearance (CL):  8.842
Half-life (T1/2):  0.881

ADMET: Toxicity

hERG Blockers:  0.035
Human Hepatotoxicity (H-HT):  0.208
Drug-inuced Liver Injury (DILI):  0.483
AMES Toxicity:  0.105
Rat Oral Acute Toxicity:  0.032
Maximum Recommended Daily Dose:  0.027
Skin Sensitization:  0.846
Carcinogencity:  0.034
Eye Corrosion:  0.185
Eye Irritation:  0.758
Respiratory Toxicity:  0.158

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

  Natural Product: NPC222175

Natural Product ID:  NPC222175
Common Name*:   Methyl (E)-3-(3,4,5-Trimethoxyphenyl)Prop-2-Enoate
IUPAC Name:   methyl (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  KLXHCGFNNUQTEY-AATRIKPKSA-N
Standard InCHI:  InChI=1S/C13H16O5/c1-15-10-7-9(5-6-12(14)17-3)8-11(16-2)13(10)18-4/h5-8H,1-4H3/b6-5+
SMILES:  COC(=O)/C=C/c1cc(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1991500
PubChem CID:   735846
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO5928 Streptomyces nashvillensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[1490884]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[16872768]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. rhizome n.a. PMID[18787781]
NPO26237 Piper longum Species Piperaceae Eukaryota fruits n.a. n.a. PMID[20839888]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[21302967]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[23434420]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[27228227]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[9544564]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11088 Ganoderma capense Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11088 Ganoderma capense Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11088 Ganoderma capense Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO868 Cephalaria gigantea Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5928 Streptomyces nashvillensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2400 Streptomyces mediolani Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11010 Melampyrum elatius Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9030 Couroupita guianensis Species Lecythidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11715 Polygonum aubertii Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3584 Oyedaea buphthalmoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12667 Goniodoma pseudogoniaulax Species Coleophoridae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 69342.58 nM PMID[571456]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 93756.2 nM PMID[571456]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 46451.53 nM PMID[571456]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 41591.06 nM PMID[571456]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 78342.96 nM PMID[571456]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 82413.81 nM PMID[571456]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 46131.76 nM PMID[571456]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 100000.0 nM PMID[571456]

☑ 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 NPC222175 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
0.9739 High Similarity NPC288238
0.9652 High Similarity NPC310373
0.9492 High Similarity NPC27352
0.9412 High Similarity NPC127604
0.9333 High Similarity NPC194841
0.9328 High Similarity NPC300326
0.9328 High Similarity NPC58279
0.9256 High Similarity NPC109275
0.9196 High Similarity NPC203924
0.918 High Similarity NPC48315
0.916 High Similarity NPC108545
0.9106 High Similarity NPC19242
0.9035 High Similarity NPC204120
0.9018 High Similarity NPC165386
0.9 High Similarity NPC238810
0.8966 High Similarity NPC123948
0.896 High Similarity NPC137669
0.896 High Similarity NPC5423
0.896 High Similarity NPC245120
0.8957 High Similarity NPC294941
0.8952 High Similarity NPC240722
0.8952 High Similarity NPC244799
0.8889 High Similarity NPC241341
0.8889 High Similarity NPC36437
0.8889 High Similarity NPC233018
0.8871 High Similarity NPC27239
0.8871 High Similarity NPC123127
0.8852 High Similarity NPC271985
0.8852 High Similarity NPC173608
0.8819 High Similarity NPC111635
0.8814 High Similarity NPC277460
0.88 High Similarity NPC299010
0.879 High Similarity NPC474623
0.879 High Similarity NPC474651
0.879 High Similarity NPC210674
0.874 High Similarity NPC288743
0.8739 High Similarity NPC475961
0.8739 High Similarity NPC37858
0.8739 High Similarity NPC254625
0.8739 High Similarity NPC308217
0.8739 High Similarity NPC69670
0.8729 High Similarity NPC212643
0.8729 High Similarity NPC199209
0.8729 High Similarity NPC304208
0.8729 High Similarity NPC52464
0.8729 High Similarity NPC33271
0.8672 High Similarity NPC309953
0.8672 High Similarity NPC92830
0.8661 High Similarity NPC319969
0.8661 High Similarity NPC123954
0.8655 High Similarity NPC124916
0.8655 High Similarity NPC63083
0.8655 High Similarity NPC107588
0.8655 High Similarity NPC70744
0.8655 High Similarity NPC272471
0.8655 High Similarity NPC137537
0.8655 High Similarity NPC164706
0.8651 High Similarity NPC79184
0.8651 High Similarity NPC307042
0.8651 High Similarity NPC476399
0.8609 High Similarity NPC179309
0.8595 High Similarity NPC267064
0.8595 High Similarity NPC472596
0.8595 High Similarity NPC199023
0.8595 High Similarity NPC166759
0.8595 High Similarity NPC204466
0.8595 High Similarity NPC471877
0.8583 High Similarity NPC119949
0.8583 High Similarity NPC15805
0.8571 High Similarity NPC259638
0.8571 High Similarity NPC153547
0.856 High Similarity NPC474670
0.855 High Similarity NPC270256
0.855 High Similarity NPC43500
0.855 High Similarity NPC164148
0.8538 High Similarity NPC167517
0.8538 High Similarity NPC286843
0.8534 High Similarity NPC245552
0.8527 High Similarity NPC155098
0.8525 High Similarity NPC477886
0.8525 High Similarity NPC70752
0.8525 High Similarity NPC114845
0.8512 High Similarity NPC202474
0.8512 High Similarity NPC229401
0.8512 High Similarity NPC474565
0.8492 Intermediate Similarity NPC304747
0.8487 Intermediate Similarity NPC268317
0.8487 Intermediate Similarity NPC193067
0.848 Intermediate Similarity NPC154275
0.8473 Intermediate Similarity NPC139548
0.8473 Intermediate Similarity NPC76336
0.8473 Intermediate Similarity NPC95162
0.8473 Intermediate Similarity NPC20511
0.8473 Intermediate Similarity NPC52086
0.8473 Intermediate Similarity NPC20796
0.8473 Intermediate Similarity NPC148835
0.8462 Intermediate Similarity NPC234865
0.8462 Intermediate Similarity NPC240915
0.8455 Intermediate Similarity NPC270326
0.8455 Intermediate Similarity NPC71579
0.8455 Intermediate Similarity NPC473411
0.8455 Intermediate Similarity NPC261661
0.8455 Intermediate Similarity NPC262253
0.845 Intermediate Similarity NPC472522
0.8443 Intermediate Similarity NPC163200
0.8438 Intermediate Similarity NPC73738
0.843 Intermediate Similarity NPC298796
0.843 Intermediate Similarity NPC20674
0.843 Intermediate Similarity NPC57501
0.8421 Intermediate Similarity NPC300611
0.8417 Intermediate Similarity NPC280001
0.8417 Intermediate Similarity NPC185738
0.8413 Intermediate Similarity NPC474821
0.8409 Intermediate Similarity NPC13067
0.8397 Intermediate Similarity NPC126682
0.8397 Intermediate Similarity NPC82271
0.8393 Intermediate Similarity NPC12714
0.8393 Intermediate Similarity NPC310905
0.839 Intermediate Similarity NPC303522
0.8387 Intermediate Similarity NPC21238
0.8387 Intermediate Similarity NPC279379
0.8387 Intermediate Similarity NPC233526
0.8387 Intermediate Similarity NPC282496
0.8385 Intermediate Similarity NPC309744
0.8385 Intermediate Similarity NPC474600
0.8385 Intermediate Similarity NPC145769
0.8385 Intermediate Similarity NPC7163
0.8374 Intermediate Similarity NPC49341
0.8374 Intermediate Similarity NPC193484
0.8362 Intermediate Similarity NPC82016
0.8361 Intermediate Similarity NPC247364
0.8361 Intermediate Similarity NPC61516
0.8361 Intermediate Similarity NPC10932
0.8361 Intermediate Similarity NPC232084
0.8361 Intermediate Similarity NPC2058
0.8358 Intermediate Similarity NPC46180
0.8347 Intermediate Similarity NPC265547
0.8347 Intermediate Similarity NPC159916
0.8347 Intermediate Similarity NPC152306
0.8347 Intermediate Similarity NPC474612
0.8346 Intermediate Similarity NPC474616
0.8333 Intermediate Similarity NPC125417
0.8333 Intermediate Similarity NPC25305
0.8333 Intermediate Similarity NPC110899
0.8333 Intermediate Similarity NPC95679
0.8333 Intermediate Similarity NPC474632
0.8333 Intermediate Similarity NPC112068
0.8321 Intermediate Similarity NPC224941
0.8321 Intermediate Similarity NPC311430
0.8321 Intermediate Similarity NPC211386
0.8321 Intermediate Similarity NPC73071
0.832 Intermediate Similarity NPC92869
0.832 Intermediate Similarity NPC60517
0.832 Intermediate Similarity NPC146886
0.832 Intermediate Similarity NPC20443
0.832 Intermediate Similarity NPC246704
0.832 Intermediate Similarity NPC283170
0.832 Intermediate Similarity NPC191768
0.832 Intermediate Similarity NPC183446
0.8308 Intermediate Similarity NPC36490
0.8306 Intermediate Similarity NPC211231
0.8306 Intermediate Similarity NPC194626
0.8296 Intermediate Similarity NPC138212
0.8293 Intermediate Similarity NPC235190
0.8293 Intermediate Similarity NPC180006
0.8279 Intermediate Similarity NPC281356
0.8279 Intermediate Similarity NPC226629
0.8276 Intermediate Similarity NPC245115
0.8264 Intermediate Similarity NPC471503
0.8264 Intermediate Similarity NPC471498
0.8258 Intermediate Similarity NPC143895
0.8258 Intermediate Similarity NPC214036
0.8258 Intermediate Similarity NPC113236
0.8258 Intermediate Similarity NPC471719
0.8254 Intermediate Similarity NPC117214
0.8254 Intermediate Similarity NPC17943
0.8254 Intermediate Similarity NPC203133
0.8254 Intermediate Similarity NPC64391
0.8254 Intermediate Similarity NPC475169
0.8254 Intermediate Similarity NPC298757
0.8254 Intermediate Similarity NPC265483
0.8254 Intermediate Similarity NPC116907
0.8254 Intermediate Similarity NPC472093
0.8254 Intermediate Similarity NPC105925
0.8254 Intermediate Similarity NPC233410
0.8254 Intermediate Similarity NPC208950
0.8254 Intermediate Similarity NPC82483
0.8254 Intermediate Similarity NPC251855
0.8254 Intermediate Similarity NPC299584
0.8254 Intermediate Similarity NPC57490
0.8254 Intermediate Similarity NPC193544
0.8254 Intermediate Similarity NPC289459
0.8254 Intermediate Similarity NPC221077
0.8254 Intermediate Similarity NPC85830
0.8246 Intermediate Similarity NPC292792
0.8244 Intermediate Similarity NPC135127
0.8244 Intermediate Similarity NPC147030
0.824 Intermediate Similarity NPC109675
0.824 Intermediate Similarity NPC165375
0.824 Intermediate Similarity NPC228922

  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 NPC222175 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
0.8509 High Similarity NPD1358 Approved
0.8455 Intermediate Similarity NPD2981 Phase 2
0.8417 Intermediate Similarity NPD5536 Phase 2
0.8387 Intermediate Similarity NPD2983 Phase 2
0.8387 Intermediate Similarity NPD2982 Phase 2
0.8125 Intermediate Similarity NPD3018 Phase 2
0.8103 Intermediate Similarity NPD3134 Approved
0.8 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD3027 Phase 3
0.7953 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7934 Intermediate Similarity NPD5283 Phase 1
0.7817 Intermediate Similarity NPD1653 Approved
0.7795 Intermediate Similarity NPD3705 Approved
0.7795 Intermediate Similarity NPD422 Phase 1
0.7786 Intermediate Similarity NPD4357 Discontinued
0.7786 Intermediate Similarity NPD5297 Approved
0.7769 Intermediate Similarity NPD228 Approved
0.7761 Intermediate Similarity NPD230 Phase 1
0.7559 Intermediate Similarity NPD5691 Approved
0.7559 Intermediate Similarity NPD1357 Approved
0.7536 Intermediate Similarity NPD3539 Phase 1
0.7519 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4626 Approved
0.75 Intermediate Similarity NPD447 Suspended
0.75 Intermediate Similarity NPD5353 Approved
0.75 Intermediate Similarity NPD3817 Phase 2
0.7482 Intermediate Similarity NPD3540 Phase 1
0.7444 Intermediate Similarity NPD9494 Approved
0.7444 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD1613 Approved
0.7426 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD2219 Phase 1
0.7391 Intermediate Similarity NPD6111 Discontinued
0.7376 Intermediate Similarity NPD1652 Phase 2
0.7351 Intermediate Similarity NPD919 Approved
0.7308 Intermediate Similarity NPD3496 Discontinued
0.7305 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD5089 Approved
0.7297 Intermediate Similarity NPD5090 Approved
0.7292 Intermediate Similarity NPD6799 Approved
0.7287 Intermediate Similarity NPD9268 Approved
0.728 Intermediate Similarity NPD5535 Approved
0.7279 Intermediate Similarity NPD1296 Phase 2
0.7273 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD9697 Approved
0.7273 Intermediate Similarity NPD5242 Approved
0.7248 Intermediate Similarity NPD37 Approved
0.7246 Intermediate Similarity NPD1933 Approved
0.7234 Intermediate Similarity NPD7266 Discontinued
0.7231 Intermediate Similarity NPD1778 Approved
0.7222 Intermediate Similarity NPD7124 Phase 2
0.7219 Intermediate Similarity NPD3882 Suspended
0.7219 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7214 Intermediate Similarity NPD3748 Approved
0.7208 Intermediate Similarity NPD6232 Discontinued
0.72 Intermediate Similarity NPD2801 Approved
0.72 Intermediate Similarity NPD4585 Approved
0.7197 Intermediate Similarity NPD9269 Phase 2
0.7194 Intermediate Similarity NPD2492 Phase 1
0.7194 Intermediate Similarity NPD2653 Approved
0.7192 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD6385 Approved
0.7181 Intermediate Similarity NPD6386 Approved
0.7133 Intermediate Similarity NPD1934 Approved
0.7123 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD3146 Approved
0.7122 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD5124 Phase 1
0.7105 Intermediate Similarity NPD4966 Approved
0.7105 Intermediate Similarity NPD4965 Approved
0.7105 Intermediate Similarity NPD4967 Phase 2
0.7099 Intermediate Similarity NPD17 Approved
0.7097 Intermediate Similarity NPD2684 Approved
0.7089 Intermediate Similarity NPD5844 Phase 1
0.7087 Intermediate Similarity NPD1241 Discontinued
0.7083 Intermediate Similarity NPD1242 Phase 1
0.7083 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD5494 Approved
0.7078 Intermediate Similarity NPD5677 Discontinued
0.7077 Intermediate Similarity NPD9545 Approved
0.7077 Intermediate Similarity NPD1548 Phase 1
0.707 Intermediate Similarity NPD7473 Discontinued
0.7055 Intermediate Similarity NPD1511 Approved
0.705 Intermediate Similarity NPD1240 Approved
0.7042 Intermediate Similarity NPD1551 Phase 2
0.7042 Intermediate Similarity NPD2935 Discontinued
0.7042 Intermediate Similarity NPD2796 Approved
0.7034 Intermediate Similarity NPD6190 Approved
0.7032 Intermediate Similarity NPD7199 Phase 2
0.7023 Intermediate Similarity NPD5585 Approved
0.7013 Intermediate Similarity NPD6234 Discontinued
0.7008 Intermediate Similarity NPD7843 Approved
0.7007 Intermediate Similarity NPD1424 Approved
0.7007 Intermediate Similarity NPD4908 Phase 1
0.7 Intermediate Similarity NPD1408 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6599 Discontinued
0.7 Intermediate Similarity NPD4340 Discontinued
0.6993 Remote Similarity NPD1375 Discontinued
0.6992 Remote Similarity NPD1610 Phase 2
0.6992 Remote Similarity NPD1281 Approved
0.698 Remote Similarity NPD3686 Approved
0.698 Remote Similarity NPD3687 Approved
0.6978 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6977 Remote Similarity NPD7157 Approved
0.6974 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6974 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6974 Remote Similarity NPD7819 Suspended
0.6974 Remote Similarity NPD1465 Phase 2
0.6972 Remote Similarity NPD1510 Phase 2
0.6966 Remote Similarity NPD4110 Phase 3
0.6966 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6966 Remote Similarity NPD4628 Phase 3
0.6966 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6966 Remote Similarity NPD3750 Approved
0.6963 Remote Similarity NPD2922 Phase 1
0.6959 Remote Similarity NPD1512 Approved
0.6957 Remote Similarity NPD7095 Approved
0.695 Remote Similarity NPD1607 Approved
0.6947 Remote Similarity NPD7534 Approved
0.6947 Remote Similarity NPD7533 Approved
0.6943 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6943 Remote Similarity NPD3926 Phase 2
0.694 Remote Similarity NPD9717 Approved
0.694 Remote Similarity NPD1608 Approved
0.6929 Remote Similarity NPD4060 Phase 1
0.6923 Remote Similarity NPD1247 Approved
0.6917 Remote Similarity NPD3847 Discontinued
0.6914 Remote Similarity NPD7549 Discontinued
0.6906 Remote Similarity NPD5109 Approved
0.6906 Remote Similarity NPD5111 Phase 2
0.6906 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6906 Remote Similarity NPD5110 Phase 2
0.6897 Remote Similarity NPD1243 Approved
0.6894 Remote Similarity NPD1651 Approved
0.6889 Remote Similarity NPD4749 Approved
0.6887 Remote Similarity NPD4678 Approved
0.6887 Remote Similarity NPD4675 Approved
0.6885 Remote Similarity NPD291 Approved
0.6885 Remote Similarity NPD940 Approved
0.6885 Remote Similarity NPD846 Approved
0.6884 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6884 Remote Similarity NPD6832 Phase 2
0.688 Remote Similarity NPD290 Approved
0.6879 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6866 Remote Similarity NPD1091 Approved
0.6861 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6861 Remote Similarity NPD1019 Discontinued
0.6846 Remote Similarity NPD1351 Approved
0.6846 Remote Similarity NPD1349 Approved
0.6846 Remote Similarity NPD1350 Approved
0.6842 Remote Similarity NPD6873 Phase 2
0.6839 Remote Similarity NPD6971 Discontinued
0.6839 Remote Similarity NPD7075 Discontinued
0.6838 Remote Similarity NPD1283 Approved
0.6838 Remote Similarity NPD3225 Approved
0.6821 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6821 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6821 Remote Similarity NPD4005 Discontinued
0.6818 Remote Similarity NPD5402 Approved
0.6813 Remote Similarity NPD3818 Discontinued
0.6809 Remote Similarity NPD1558 Phase 1
0.6807 Remote Similarity NPD9296 Approved
0.6806 Remote Similarity NPD2438 Suspended
0.68 Remote Similarity NPD920 Approved
0.68 Remote Similarity NPD5403 Approved
0.6797 Remote Similarity NPD6801 Discontinued
0.6794 Remote Similarity NPD9493 Approved
0.6792 Remote Similarity NPD6166 Phase 2
0.6792 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6792 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6786 Remote Similarity NPD3144 Approved
0.6786 Remote Similarity NPD411 Approved
0.6786 Remote Similarity NPD5718 Phase 2
0.6786 Remote Similarity NPD3145 Approved
0.6781 Remote Similarity NPD4237 Approved
0.6781 Remote Similarity NPD4236 Phase 3
0.6779 Remote Similarity NPD2532 Approved
0.6779 Remote Similarity NPD2534 Approved
0.6779 Remote Similarity NPD2533 Approved
0.6779 Remote Similarity NPD5401 Approved
0.6772 Remote Similarity NPD5451 Approved
0.677 Remote Similarity NPD7054 Approved
0.6765 Remote Similarity NPD4359 Approved
0.6757 Remote Similarity NPD643 Clinical (unspecified phase)
0.6755 Remote Similarity NPD4210 Discontinued
0.6741 Remote Similarity NPD1611 Approved
0.6738 Remote Similarity NPD6233 Phase 2
0.6738 Remote Similarity NPD2674 Phase 3
0.6738 Remote Similarity NPD554 Clinical (unspecified phase)
0.6732 Remote Similarity NPD7411 Suspended
0.6731 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6728 Remote Similarity NPD7074 Phase 3
0.6728 Remote Similarity NPD7472 Approved
0.6714 Remote Similarity NPD2669 Clinical (unspecified phase)
0.6714 Remote Similarity NPD4625 Phase 3
0.6713 Remote Similarity NPD1772 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