Structure

Physi-Chem Properties

Molecular Weight:  256.11
Volume:  276.095
LogP:  3.831
LogD:  3.798
LogS:  -4.012
# Rotatable Bonds:  4
TPSA:  38.69
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.85
Synthetic Accessibility Score:  1.887
Fsp3:  0.125
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:  -4.929
MDCK Permeability:  1.558466647111345e-05
Pgp-inhibitor:  0.947
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.012
30% Bioavailability (F30%):  0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.247
Plasma Protein Binding (PPB):  99.19316864013672%
Volume Distribution (VD):  1.051
Pgp-substrate:  1.086905837059021%

ADMET: Metabolism

CYP1A2-inhibitor:  0.973
CYP1A2-substrate:  0.944
CYP2C19-inhibitor:  0.808
CYP2C19-substrate:  0.608
CYP2C9-inhibitor:  0.264
CYP2C9-substrate:  0.954
CYP2D6-inhibitor:  0.606
CYP2D6-substrate:  0.949
CYP3A4-inhibitor:  0.865
CYP3A4-substrate:  0.484

ADMET: Excretion

Clearance (CL):  11.281
Half-life (T1/2):  0.864

ADMET: Toxicity

hERG Blockers:  0.443
Human Hepatotoxicity (H-HT):  0.667
Drug-inuced Liver Injury (DILI):  0.304
AMES Toxicity:  0.608
Rat Oral Acute Toxicity:  0.028
Maximum Recommended Daily Dose:  0.34
Skin Sensitization:  0.96
Carcinogencity:  0.185
Eye Corrosion:  0.02
Eye Irritation:  0.961
Respiratory Toxicity:  0.624

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Similar NPs/Drugs  

  Natural Product: NPC228287

Natural Product ID:  NPC228287
Common Name*:   (Z)-4-(3,5-Dimethoxystyryl)Phenol
IUPAC Name:   4-[(Z)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
Synonyms:  
Standard InCHIKey:  VLEUZFDZJKSGMX-ARJAWSKDSA-N
Standard InCHI:  InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3-
SMILES:  COc1cc(/C=Cc2ccc(cc2)O)cc(c1)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL87712
PubChem CID:   5320791
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
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. Nigeria(latitude 80°N and longitude 4°E) 2005; 2006 DOI[10.1002/ejlt.201000080]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11306-010-0259-y]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11306-014-0638-x]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11746-997-0093-1]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytol.2008.07.007]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seeds Plovdiv, Plovdiv region in South Bulgaria DOI[10.1051/CTV/20163101031]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[11170689]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. fruit n.a. PMID[11312782]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. leaf n.a. PMID[11312782]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[11408943]
NPO12714 Dracaena cochinchinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. PMID[12016928]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. fruit n.a. PMID[12105962]
NPO12714 Dracaena cochinchinensis Species Asparagaceae Eukaryota stems Ningming County, Guangxi autonomous region, China 2006-Jan PMID[17883259]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete 2007 PMID[19256538]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[20826702]
NPO1087 Pterocarpus santalinus Species Fabaceae Eukaryota n.a. heartwood n.a. PMID[21488654]
NPO1087 Pterocarpus santalinus Species Fabaceae Eukaryota Heartwood India n.a. PMID[21488654]
NPO12714 Dracaena cochinchinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. PMID[21661731]
NPO1087 Pterocarpus santalinus Species Fabaceae Eukaryota heartwood n.a. n.a. PMID[21784631]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[22537213]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[23759170]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Stalks n.a. n.a. PMID[24521157]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25333853]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota rhizomes Liaoning province, China 2011-SEP PMID[25927664]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seeds Benedictine Pannonhalma Archabbey, Hungary PMID[29803478]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. PMID[31433178]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Fruits n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO1087 Pterocarpus santalinus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13087.1 Pteridium aquilinum var. latiusculum Varieties Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13426 Lemmaphyllum microphyllum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7255 Pterocarpus indicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12714 Dracaena cochinchinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO7255 Pterocarpus indicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13087.1 Pteridium aquilinum var. latiusculum Varieties Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1087 Pterocarpus santalinus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13426 Lemmaphyllum microphyllum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12714 Dracaena cochinchinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1087 Pterocarpus santalinus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12714 Dracaena cochinchinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12714 Dracaena cochinchinensis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17024 Vitis vinifera Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7255 Pterocarpus indicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13426 Lemmaphyllum microphyllum Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1087 Pterocarpus santalinus Species Fabaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 2000.0 nM PMID[481209]
NPT116 Cell Line HL-60 Homo sapiens AC50 = 5000.0 nM PMID[481209]
NPT168 Cell Line P388 Mus musculus ED50 = 2.95 ug ml-1 PMID[481210]
NPT1081 Cell Line BXPC-3 Homo sapiens GI50 = 12.6 ug.mL-1 PMID[481210]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 3.0 ug.mL-1 PMID[481210]
NPT395 Cell Line SF-268 Homo sapiens GI50 = 2.2 ug.mL-1 PMID[481210]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 = 11.9 ug.mL-1 PMID[481210]
NPT90 Cell Line DU-145 Homo sapiens GI50 = 2.3 ug.mL-1 PMID[481210]
NPT2 Others Unspecified GI50 = 2.8 ug.mL-1 PMID[481210]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 16.0 ug.mL-1 PMID[481210]
NPT20 Organism Candida albicans Candida albicans MIC = 64.0 ug.mL-1 PMID[481210]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 32.0 ug.mL-1 PMID[481210]
NPT1118 Organism Streptococcus pneumoniae Streptococcus pneumoniae MIC = 16.0 ug.mL-1 PMID[481210]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC = 32.0 ug.mL-1 PMID[481210]
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 8.0 ug.mL-1 PMID[481210]
NPT19 Organism Escherichia coli Escherichia coli MIC = 0.0 ug.mL-1 PMID[481210]
NPT1033 Organism Enterobacter cloacae Enterobacter cloacae MIC = 0.0 ug.mL-1 PMID[481210]
NPT1521 Organism Stenotrophomonas maltophilia Stenotrophomonas maltophilia MIC = 0.0 ug.mL-1 PMID[481210]
NPT1522 Organism Neisseria gonorrhoeae Neisseria gonorrhoeae MIC = 8.0 ug.mL-1 PMID[481210]
NPT782 Protein Family Tubulin Bos taurus IC50 = 29000.0 nM PMID[481210]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. INH = 6.3 10'4L/mol/s PMID[481211]

☑ 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 NPC228287 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 NPC180508
0.9811 High Similarity NPC280606
0.9725 High Similarity NPC474933
0.9717 High Similarity NPC296920
0.9717 High Similarity NPC90520
0.9633 High Similarity NPC141090
0.9623 High Similarity NPC94045
0.9541 High Similarity NPC53906
0.9528 High Similarity NPC82016
0.9455 High Similarity NPC203113
0.945 High Similarity NPC22610
0.945 High Similarity NPC276737
0.9381 High Similarity NPC102639
0.9381 High Similarity NPC166759
0.9369 High Similarity NPC219070
0.9369 High Similarity NPC15860
0.9369 High Similarity NPC127894
0.9369 High Similarity NPC195466
0.9369 High Similarity NPC33270
0.9369 High Similarity NPC69261
0.9369 High Similarity NPC470759
0.9364 High Similarity NPC464
0.9364 High Similarity NPC185541
0.934 High Similarity NPC35543
0.9298 High Similarity NPC476633
0.9292 High Similarity NPC474565
0.9279 High Similarity NPC85292
0.9279 High Similarity NPC150624
0.9279 High Similarity NPC114064
0.9279 High Similarity NPC54507
0.9279 High Similarity NPC229147
0.9252 High Similarity NPC245115
0.9245 High Similarity NPC164576
0.9217 High Similarity NPC262253
0.9217 High Similarity NPC473411
0.9217 High Similarity NPC71579
0.9204 High Similarity NPC184302
0.9204 High Similarity NPC226629
0.9189 High Similarity NPC808
0.9189 High Similarity NPC167934
0.9174 High Similarity NPC255068
0.9138 High Similarity NPC282496
0.9138 High Similarity NPC233526
0.9138 High Similarity NPC136319
0.9115 High Similarity NPC131118
0.9115 High Similarity NPC190514
0.9083 High Similarity NPC168657
0.9083 High Similarity NPC2682
0.906 High Similarity NPC270030
0.9057 High Similarity NPC474603
0.9057 High Similarity NPC12987
0.9027 High Similarity NPC50521
0.9027 High Similarity NPC221549
0.9027 High Similarity NPC244816
0.8983 High Similarity NPC233410
0.8983 High Similarity NPC116907
0.8983 High Similarity NPC234400
0.8983 High Similarity NPC57490
0.8983 High Similarity NPC298757
0.8983 High Similarity NPC203133
0.8983 High Similarity NPC251855
0.8983 High Similarity NPC472093
0.8983 High Similarity NPC117214
0.8983 High Similarity NPC221077
0.8983 High Similarity NPC193544
0.8983 High Similarity NPC265483
0.8983 High Similarity NPC105031
0.8983 High Similarity NPC475169
0.8983 High Similarity NPC82483
0.8983 High Similarity NPC17943
0.8983 High Similarity NPC208950
0.8983 High Similarity NPC113495
0.8983 High Similarity NPC105925
0.8983 High Similarity NPC60885
0.8983 High Similarity NPC299584
0.8966 High Similarity NPC75713
0.8957 High Similarity NPC247364
0.8957 High Similarity NPC10932
0.8957 High Similarity NPC232084
0.8957 High Similarity NPC61516
0.8938 High Similarity NPC123948
0.8908 High Similarity NPC28730
0.8908 High Similarity NPC78974
0.8908 High Similarity NPC170485
0.8908 High Similarity NPC214406
0.8908 High Similarity NPC223136
0.8908 High Similarity NPC18924
0.8908 High Similarity NPC103823
0.8908 High Similarity NPC44748
0.8899 High Similarity NPC75440
0.8889 High Similarity NPC18128
0.8889 High Similarity NPC41562
0.8889 High Similarity NPC77789
0.886 High Similarity NPC259638
0.8833 High Similarity NPC236791
0.8833 High Similarity NPC127587
0.8833 High Similarity NPC210355
0.8833 High Similarity NPC159968
0.8833 High Similarity NPC82679
0.8833 High Similarity NPC324112
0.8833 High Similarity NPC246620
0.8833 High Similarity NPC74817
0.8833 High Similarity NPC124452
0.8833 High Similarity NPC473221
0.8833 High Similarity NPC282000
0.8833 High Similarity NPC293054
0.8833 High Similarity NPC169474
0.8814 High Similarity NPC197757
0.8814 High Similarity NPC228922
0.8814 High Similarity NPC95168
0.8814 High Similarity NPC84086
0.8814 High Similarity NPC474160
0.8774 High Similarity NPC275053
0.8774 High Similarity NPC248573
0.8774 High Similarity NPC161571
0.8772 High Similarity NPC193067
0.876 High Similarity NPC470213
0.876 High Similarity NPC98631
0.876 High Similarity NPC206615
0.876 High Similarity NPC186843
0.875 High Similarity NPC223953
0.875 High Similarity NPC76451
0.875 High Similarity NPC82299
0.8739 High Similarity NPC138248
0.8739 High Similarity NPC5796
0.8739 High Similarity NPC206487
0.8739 High Similarity NPC122792
0.8739 High Similarity NPC303521
0.8739 High Similarity NPC228972
0.8739 High Similarity NPC228503
0.8729 High Similarity NPC100099
0.8729 High Similarity NPC74137
0.8729 High Similarity NPC36016
0.8727 High Similarity NPC201959
0.8716 High Similarity NPC113457
0.8707 High Similarity NPC137294
0.8707 High Similarity NPC295259
0.8707 High Similarity NPC85895
0.8707 High Similarity NPC475961
0.8707 High Similarity NPC20674
0.8707 High Similarity NPC254625
0.8689 High Similarity NPC58164
0.8689 High Similarity NPC10225
0.8689 High Similarity NPC228769
0.8689 High Similarity NPC471519
0.8689 High Similarity NPC170844
0.8689 High Similarity NPC476968
0.8689 High Similarity NPC470633
0.8689 High Similarity NPC471518
0.8689 High Similarity NPC190144
0.8678 High Similarity NPC46978
0.8667 High Similarity NPC278955
0.8667 High Similarity NPC105718
0.8661 High Similarity NPC203924
0.8655 High Similarity NPC76465
0.8655 High Similarity NPC38761
0.8644 High Similarity NPC212965
0.8644 High Similarity NPC145780
0.8644 High Similarity NPC54972
0.8632 High Similarity NPC229401
0.8621 High Similarity NPC74821
0.8618 High Similarity NPC51840
0.8618 High Similarity NPC224157
0.8618 High Similarity NPC472338
0.8618 High Similarity NPC63574
0.8618 High Similarity NPC234488
0.8618 High Similarity NPC254000
0.8618 High Similarity NPC299221
0.8618 High Similarity NPC126836
0.8618 High Similarity NPC192687
0.8618 High Similarity NPC311680
0.8607 High Similarity NPC28765
0.8607 High Similarity NPC154866
0.8607 High Similarity NPC215300
0.8595 High Similarity NPC283049
0.8595 High Similarity NPC50315
0.8595 High Similarity NPC230479
0.8595 High Similarity NPC26879
0.8585 High Similarity NPC291789
0.8583 High Similarity NPC197351
0.8583 High Similarity NPC106914
0.8583 High Similarity NPC86502
0.8583 High Similarity NPC140521
0.8583 High Similarity NPC134195
0.8583 High Similarity NPC246648
0.8571 High Similarity NPC120638
0.8559 High Similarity NPC199023
0.8559 High Similarity NPC218753
0.8559 High Similarity NPC472596
0.8548 High Similarity NPC470096
0.8548 High Similarity NPC45715
0.8548 High Similarity NPC472597
0.8548 High Similarity NPC471517
0.8548 High Similarity NPC282508
0.8548 High Similarity NPC474017
0.8548 High Similarity NPC473309
0.8548 High Similarity NPC12275
0.8548 High Similarity NPC474356
0.8548 High Similarity NPC470095
0.8548 High Similarity NPC15543

  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 NPC228287 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
0.8774 High Similarity NPD1242 Phase 1
0.8689 High Similarity NPD3027 Phase 3
0.8621 High Similarity NPD1548 Phase 1
0.85 High Similarity NPD2982 Phase 2
0.85 High Similarity NPD2983 Phase 2
0.8487 Intermediate Similarity NPD1610 Phase 2
0.8455 Intermediate Similarity NPD4908 Phase 1
0.8417 Intermediate Similarity NPD2981 Phase 2
0.832 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.824 Intermediate Similarity NPD4625 Phase 3
0.8226 Intermediate Similarity NPD3018 Phase 2
0.8197 Intermediate Similarity NPD4749 Approved
0.816 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.808 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD1613 Approved
0.8047 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8033 Intermediate Similarity NPD422 Phase 1
0.8018 Intermediate Similarity NPD940 Approved
0.8018 Intermediate Similarity NPD846 Approved
0.8017 Intermediate Similarity NPD228 Approved
0.8 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7963 Intermediate Similarity NPD2933 Approved
0.7963 Intermediate Similarity NPD2934 Approved
0.7937 Intermediate Similarity NPD2861 Phase 2
0.7903 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7903 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD968 Approved
0.7891 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7891 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.789 Intermediate Similarity NPD2859 Approved
0.789 Intermediate Similarity NPD2860 Approved
0.7881 Intermediate Similarity NPD5283 Phase 1
0.7845 Intermediate Similarity NPD4750 Phase 3
0.7838 Intermediate Similarity NPD3020 Approved
0.7769 Intermediate Similarity NPD1240 Approved
0.775 Intermediate Similarity NPD6671 Approved
0.7717 Intermediate Similarity NPD6584 Phase 3
0.7692 Intermediate Similarity NPD5451 Approved
0.7652 Intermediate Similarity NPD1607 Approved
0.7623 Intermediate Similarity NPD5536 Phase 2
0.7609 Intermediate Similarity NPD4357 Discontinued
0.7607 Intermediate Similarity NPD2684 Approved
0.7556 Intermediate Similarity NPD3540 Phase 1
0.7542 Intermediate Similarity NPD3022 Approved
0.7542 Intermediate Similarity NPD3021 Approved
0.7537 Intermediate Similarity NPD1510 Phase 2
0.75 Intermediate Similarity NPD2238 Phase 2
0.75 Intermediate Similarity NPD1357 Approved
0.7481 Intermediate Similarity NPD3539 Phase 1
0.7481 Intermediate Similarity NPD6100 Approved
0.7481 Intermediate Similarity NPD6099 Approved
0.748 Intermediate Similarity NPD6582 Phase 2
0.748 Intermediate Similarity NPD6583 Phase 3
0.7453 Intermediate Similarity NPD111 Approved
0.744 Intermediate Similarity NPD2667 Approved
0.744 Intermediate Similarity NPD2668 Approved
0.744 Intermediate Similarity NPD4626 Approved
0.7436 Intermediate Similarity NPD3134 Approved
0.7429 Intermediate Similarity NPD7447 Phase 1
0.7429 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD2230 Approved
0.7402 Intermediate Similarity NPD2232 Approved
0.7402 Intermediate Similarity NPD2233 Approved
0.7402 Intermediate Similarity NPD1608 Approved
0.7381 Intermediate Similarity NPD3847 Discontinued
0.7373 Intermediate Similarity NPD290 Approved
0.7372 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD4060 Phase 1
0.7368 Intermediate Similarity NPD1558 Phase 1
0.736 Intermediate Similarity NPD1651 Approved
0.7357 Intermediate Similarity NPD7212 Phase 2
0.7357 Intermediate Similarity NPD7213 Phase 3
0.7355 Intermediate Similarity NPD821 Approved
0.7355 Intermediate Similarity NPD7843 Approved
0.7355 Intermediate Similarity NPD5535 Approved
0.7353 Intermediate Similarity NPD2935 Discontinued
0.7344 Intermediate Similarity NPD1669 Approved
0.7339 Intermediate Similarity NPD9295 Approved
0.7323 Intermediate Similarity NPD1091 Approved
0.7321 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD7157 Approved
0.7317 Intermediate Similarity NPD709 Approved
0.7308 Intermediate Similarity NPD4624 Approved
0.7302 Intermediate Similarity NPD1778 Approved
0.7299 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD4675 Approved
0.7292 Intermediate Similarity NPD4678 Approved
0.7287 Intermediate Similarity NPD1283 Approved
0.728 Intermediate Similarity NPD1182 Approved
0.7266 Intermediate Similarity NPD3892 Phase 2
0.7266 Intermediate Similarity NPD3750 Approved
0.7266 Intermediate Similarity NPD2235 Phase 2
0.7266 Intermediate Similarity NPD2231 Phase 2
0.726 Intermediate Similarity NPD2801 Approved
0.726 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD4097 Suspended
0.7257 Intermediate Similarity NPD844 Approved
0.7246 Intermediate Similarity NPD1549 Phase 2
0.7234 Intermediate Similarity NPD1511 Approved
0.7227 Intermediate Similarity NPD1358 Approved
0.7226 Intermediate Similarity NPD2796 Approved
0.7226 Intermediate Similarity NPD1551 Phase 2
0.7222 Intermediate Similarity NPD5585 Approved
0.7214 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7214 Intermediate Similarity NPD2219 Phase 1
0.7194 Intermediate Similarity NPD3060 Approved
0.7194 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD1934 Approved
0.7188 Intermediate Similarity NPD3705 Approved
0.7185 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7185 Intermediate Similarity NPD5124 Phase 1
0.717 Intermediate Similarity NPD9089 Approved
0.7165 Intermediate Similarity NPD5846 Approved
0.7165 Intermediate Similarity NPD2423 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD17 Approved
0.7165 Intermediate Similarity NPD6516 Phase 2
0.7163 Intermediate Similarity NPD7124 Phase 2
0.7162 Intermediate Similarity NPD3882 Suspended
0.7154 Intermediate Similarity NPD3225 Approved
0.7154 Intermediate Similarity NPD6696 Suspended
0.7143 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7095 Approved
0.7143 Intermediate Similarity NPD1894 Discontinued
0.7133 Intermediate Similarity NPD1512 Approved
0.7132 Intermediate Similarity NPD2568 Approved
0.7132 Intermediate Similarity NPD3052 Approved
0.7132 Intermediate Similarity NPD3054 Approved
0.712 Intermediate Similarity NPD3596 Phase 2
0.7111 Intermediate Similarity NPD3620 Phase 2
0.7111 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD3496 Discontinued
0.7103 Intermediate Similarity NPD4005 Discontinued
0.7099 Intermediate Similarity NPD2797 Approved
0.709 Intermediate Similarity NPD3145 Approved
0.709 Intermediate Similarity NPD3144 Approved
0.7087 Intermediate Similarity NPD5691 Approved
0.708 Intermediate Similarity NPD6111 Discontinued
0.708 Intermediate Similarity NPD4538 Approved
0.708 Intermediate Similarity NPD4536 Approved
0.708 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD5327 Phase 3
0.7075 Intermediate Similarity NPD9093 Approved
0.7075 Intermediate Similarity NPD37 Approved
0.7063 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD5735 Approved
0.7059 Intermediate Similarity NPD230 Phase 1
0.7055 Intermediate Similarity NPD4380 Phase 2
0.7054 Intermediate Similarity NPD1281 Approved
0.7054 Intermediate Similarity NPD1535 Discovery
0.7043 Intermediate Similarity NPD288 Approved
0.7037 Intermediate Similarity NPD2674 Phase 3
0.7034 Intermediate Similarity NPD1653 Approved
0.7027 Intermediate Similarity NPD7819 Suspended
0.7023 Intermediate Similarity NPD8651 Approved
0.7021 Intermediate Similarity NPD7466 Approved
0.7021 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD9296 Approved
0.7009 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD3028 Approved
0.7008 Intermediate Similarity NPD6580 Approved
0.7008 Intermediate Similarity NPD6581 Approved
0.7008 Intermediate Similarity NPD3091 Approved
0.7008 Intermediate Similarity NPD9545 Approved
0.7007 Intermediate Similarity NPD1772 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1840 Phase 2
0.7 Intermediate Similarity NPD1481 Phase 2
0.6993 Remote Similarity NPD6799 Approved
0.6993 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6992 Remote Similarity NPD4993 Discontinued
0.6992 Remote Similarity NPD9494 Approved
0.6985 Remote Similarity NPD4140 Approved
0.698 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6966 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6954 Remote Similarity NPD6234 Discontinued
0.6953 Remote Similarity NPD6830 Clinical (unspecified phase)
0.695 Remote Similarity NPD4236 Phase 3
0.695 Remote Similarity NPD4237 Approved
0.695 Remote Similarity NPD1652 Phase 2
0.6947 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6947 Remote Similarity NPD4359 Approved
0.6944 Remote Similarity NPD4123 Phase 3
0.694 Remote Similarity NPD600 Approved
0.694 Remote Similarity NPD1008 Clinical (unspecified phase)
0.694 Remote Similarity NPD596 Approved
0.694 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6935 Remote Similarity NPD7635 Approved
0.6934 Remote Similarity NPD4340 Discontinued
0.6933 Remote Similarity NPD4965 Approved
0.6933 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6933 Remote Similarity NPD4967 Phase 2
0.6933 Remote Similarity NPD4966 Approved
0.6933 Remote Similarity NPD7768 Phase 2
0.6929 Remote Similarity NPD7266 Discontinued
0.6928 Remote Similarity NPD6232 Discontinued
0.6923 Remote Similarity NPD3092 Approved
0.6917 Remote Similarity NPD3690 Phase 2
0.6917 Remote Similarity NPD3691 Phase 2
0.6912 Remote Similarity NPD6233 Phase 2
0.6906 Remote Similarity NPD5960 Phase 3

  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