Structure

Physi-Chem Properties

Molecular Weight:  360.08
Volume:  343.445
LogP:  2.52
LogD:  2.218
LogS:  -3.877
# Rotatable Bonds:  4
TPSA:  118.59
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.608
Synthetic Accessibility Score:  2.506
Fsp3:  0.167
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.983
MDCK Permeability:  1.4874191947455984e-05
Pgp-inhibitor:  0.995
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.042
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.004
Plasma Protein Binding (PPB):  89.77647399902344%
Volume Distribution (VD):  0.81
Pgp-substrate:  18.611026763916016%

ADMET: Metabolism

CYP1A2-inhibitor:  0.736
CYP1A2-substrate:  0.97
CYP2C19-inhibitor:  0.119
CYP2C19-substrate:  0.08
CYP2C9-inhibitor:  0.723
CYP2C9-substrate:  0.727
CYP2D6-inhibitor:  0.184
CYP2D6-substrate:  0.473
CYP3A4-inhibitor:  0.336
CYP3A4-substrate:  0.222

ADMET: Excretion

Clearance (CL):  5.609
Half-life (T1/2):  0.882

ADMET: Toxicity

hERG Blockers:  0.052
Human Hepatotoxicity (H-HT):  0.094
Drug-inuced Liver Injury (DILI):  0.974
AMES Toxicity:  0.502
Rat Oral Acute Toxicity:  0.166
Maximum Recommended Daily Dose:  0.15
Skin Sensitization:  0.607
Carcinogencity:  0.035
Eye Corrosion:  0.003
Eye Irritation:  0.881
Respiratory Toxicity:  0.152

Download Data

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Similar NPs/Drugs  

  Natural Product: NPC300943

Natural Product ID:  NPC300943
Common Name*:   5,6,3'-Trihydroxy-3,7,4'-Trimethoxyflavone
IUPAC Name:   5,6-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxychromen-4-one
Synonyms:  
Standard InCHIKey:  UQBUUCDVKDSHCE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H16O8/c1-23-10-5-4-8(6-9(10)19)17-18(25-3)16(22)13-11(26-17)7-12(24-2)14(20)15(13)21/h4-7,19-21H,1-3H3
SMILES:  COc1ccc(cc1O)c1oc2cc(OC)c(c(c2c(=O)c1OC)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1085428
PubChem CID:   442621
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002585] O-methylated flavonoids
          • [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO22842 Lissoclinum bistratum Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[12608858]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota stems n.a. n.a. PMID[12932126]
NPO23263 Crinum yemense Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[15270564]
NPO23510 Vicia faba Species Fabaceae Eukaryota flowers n.a. n.a. PMID[16180811]
NPO14937 Gelonium aequoreum Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[17714747]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota aerial parts n.a. n.a. PMID[19299148]
NPO25696 Hyptis brevipes Species Lamiaceae Eukaryota Whole Plant Tawangmangu village, Karanganyar, Central Java, Indonesia 2003-FEB PMID[19422206]
NPO25696 Hyptis brevipes Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[19422206]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[20681570]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. leaf n.a. PMID[22014228]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. branch n.a. PMID[22014228]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22014228]
NPO16026 Gnetum montanum Species Gnetaceae Eukaryota n.a. leaf n.a. PMID[22040053]
NPO16026 Gnetum montanum Species Gnetaceae Eukaryota leaves Guangxi Province, China 2000-JAN PMID[22040053]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. stem n.a. PMID[22210168]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. leaf n.a. PMID[22210168]
NPO25696 Hyptis brevipes Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23282042]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[2691636]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[2691636]
NPO25696 Hyptis brevipes Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[28099005]
NPO22842 Lissoclinum bistratum Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[7807120]
NPO13635 Rhodiola quadrifida Species Crassulaceae Eukaryota n.a. root n.a. PMID[8945774]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota Twigs and leaves Taichung, Taiwan 1993-Aug PMID[9322359]
NPO23510 Vicia faba Species Fabaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22186 Baileya pauciradiata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28036 Distemonanthus benthamianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13635 Rhodiola quadrifida Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13635 Rhodiola quadrifida Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23107 Adiantum monochlamys Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22186 Baileya pauciradiata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5195.1 Odontites vernus subsp. serotinus Subspecies Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28036 Distemonanthus benthamianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28036 Distemonanthus benthamianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22186 Baileya pauciradiata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14140 Vernonia arbor Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28036 Distemonanthus benthamianus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11989 Erythrostemon gilliesii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20857 Commiphora erythraea Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9482 Durio kutejensis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24279 Streptomyces inusitatus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22842 Lissoclinum bistratum Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15464 Argylia radiata Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23107 Adiantum monochlamys Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO845 Cyrtanthus obliquus Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22186 Baileya pauciradiata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3903 Hemizonia congesta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23562 Pachyphragma macrophyllum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16558 Mallotus stenanthus Species Salangidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13635 Rhodiola quadrifida Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16231 Helichrysum acutatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5195.1 Odontites vernus subsp. serotinus Subspecies Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23648 Spilanthes mauritiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5874 Fumago vagans n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23427 Becium grandiflorum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO14937 Gelonium aequoreum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10679 Scutellaria nepetoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13731 Centaurea webbiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14473 Stellaria delavayi Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25696 Hyptis brevipes Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2865 Abrus precatorius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23263 Crinum yemense Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18884 Apuleia leiocarpa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13988 Westiella intricata Species Hapalosiphonaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16026 Gnetum montanum Species Gnetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16719 Alluaudia dumosa Species Didiereaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6943 Vernonanthura chamaedrys Species Asteraceae 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
NPT139 Cell Line HT-29 Homo sapiens ED50 = 3.6 uM PMID[464581]
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens ED50 > 50.0 uM PMID[464581]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 310.0 nM PMID[464581]
NPT2 Others Unspecified ED50 = 17.0 uM PMID[464581]

☑ 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 NPC300943 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 NPC253634
1.0 High Similarity NPC19687
1.0 High Similarity NPC288669
1.0 High Similarity NPC152166
1.0 High Similarity NPC143828
1.0 High Similarity NPC191459
1.0 High Similarity NPC18607
1.0 High Similarity NPC115798
1.0 High Similarity NPC9609
1.0 High Similarity NPC18772
1.0 High Similarity NPC130894
1.0 High Similarity NPC4481
1.0 High Similarity NPC105242
1.0 High Similarity NPC176300
1.0 High Similarity NPC22472
1.0 High Similarity NPC261004
1.0 High Similarity NPC204854
1.0 High Similarity NPC7846
1.0 High Similarity NPC25495
0.9933 High Similarity NPC101830
0.9933 High Similarity NPC176665
0.9933 High Similarity NPC189179
0.9933 High Similarity NPC7973
0.9933 High Similarity NPC227192
0.9933 High Similarity NPC78302
0.9933 High Similarity NPC163524
0.9933 High Similarity NPC93376
0.9933 High Similarity NPC203891
0.9933 High Similarity NPC29841
0.9933 High Similarity NPC235215
0.9933 High Similarity NPC472438
0.9933 High Similarity NPC110070
0.9933 High Similarity NPC224137
0.9933 High Similarity NPC287979
0.9933 High Similarity NPC305663
0.9933 High Similarity NPC75215
0.9868 High Similarity NPC193842
0.9867 High Similarity NPC43243
0.9867 High Similarity NPC55619
0.9867 High Similarity NPC200388
0.9867 High Similarity NPC100916
0.9867 High Similarity NPC474520
0.9867 High Similarity NPC247017
0.9867 High Similarity NPC268161
0.9867 High Similarity NPC178854
0.9867 High Similarity NPC266960
0.9867 High Similarity NPC49824
0.9867 High Similarity NPC245546
0.9867 High Similarity NPC292107
0.9867 High Similarity NPC98661
0.98 High Similarity NPC214138
0.98 High Similarity NPC196439
0.98 High Similarity NPC50715
0.98 High Similarity NPC32557
0.98 High Similarity NPC189960
0.98 High Similarity NPC167815
0.98 High Similarity NPC92659
0.98 High Similarity NPC4455
0.98 High Similarity NPC2476
0.98 High Similarity NPC44079
0.98 High Similarity NPC280339
0.98 High Similarity NPC201136
0.98 High Similarity NPC138360
0.98 High Similarity NPC163780
0.98 High Similarity NPC26227
0.98 High Similarity NPC128863
0.98 High Similarity NPC201451
0.98 High Similarity NPC183597
0.98 High Similarity NPC146165
0.98 High Similarity NPC227325
0.9735 High Similarity NPC265511
0.9733 High Similarity NPC276409
0.9733 High Similarity NPC86485
0.9733 High Similarity NPC250822
0.9733 High Similarity NPC69394
0.9733 High Similarity NPC162351
0.9733 High Similarity NPC270620
0.9733 High Similarity NPC78326
0.9733 High Similarity NPC75279
0.9733 High Similarity NPC183878
0.9733 High Similarity NPC160951
0.9733 High Similarity NPC22519
0.9733 High Similarity NPC246204
0.9733 High Similarity NPC231018
0.9733 High Similarity NPC179126
0.9733 High Similarity NPC274327
0.9733 High Similarity NPC145379
0.9733 High Similarity NPC236223
0.9733 High Similarity NPC58382
0.9733 High Similarity NPC176775
0.9733 High Similarity NPC255350
0.9733 High Similarity NPC47781
0.9673 High Similarity NPC246478
0.9669 High Similarity NPC256612
0.9669 High Similarity NPC20830
0.9669 High Similarity NPC208197
0.9669 High Similarity NPC213622
0.9667 High Similarity NPC57030
0.9667 High Similarity NPC301123
0.9667 High Similarity NPC83508
0.9667 High Similarity NPC275722
0.9667 High Similarity NPC120163
0.9667 High Similarity NPC301323
0.9667 High Similarity NPC82325
0.9667 High Similarity NPC25270
0.9667 High Similarity NPC279989
0.9667 High Similarity NPC156222
0.9667 High Similarity NPC198826
0.9667 High Similarity NPC123886
0.9667 High Similarity NPC27208
0.9667 High Similarity NPC100887
0.9667 High Similarity NPC256283
0.9667 High Similarity NPC222830
0.9667 High Similarity NPC293183
0.9667 High Similarity NPC239128
0.9667 High Similarity NPC187498
0.9667 High Similarity NPC188203
0.9667 High Similarity NPC142540
0.9667 High Similarity NPC241498
0.9667 High Similarity NPC162313
0.9667 High Similarity NPC134677
0.9667 High Similarity NPC275836
0.9667 High Similarity NPC131624
0.9667 High Similarity NPC212678
0.9667 High Similarity NPC71334
0.9613 High Similarity NPC470459
0.9608 High Similarity NPC195832
0.96 High Similarity NPC76376
0.96 High Similarity NPC208043
0.96 High Similarity NPC252933
0.96 High Similarity NPC226973
0.96 High Similarity NPC133953
0.96 High Similarity NPC225731
0.96 High Similarity NPC50403
0.96 High Similarity NPC125062
0.96 High Similarity NPC236769
0.96 High Similarity NPC28274
0.96 High Similarity NPC200740
0.96 High Similarity NPC54394
0.9554 High Similarity NPC76482
0.9551 High Similarity NPC470457
0.9542 High Similarity NPC470402
0.9536 High Similarity NPC55205
0.9536 High Similarity NPC39732
0.9536 High Similarity NPC60972
0.9533 High Similarity NPC201547
0.9533 High Similarity NPC77858
0.9533 High Similarity NPC219330
0.9533 High Similarity NPC188871
0.9533 High Similarity NPC50728
0.9533 High Similarity NPC166753
0.9533 High Similarity NPC286342
0.9533 High Similarity NPC259058
0.9533 High Similarity NPC306821
0.9533 High Similarity NPC184136
0.9533 High Similarity NPC149127
0.9494 High Similarity NPC280493
0.949 High Similarity NPC470462
0.9481 High Similarity NPC152904
0.9477 High Similarity NPC472916
0.947 High Similarity NPC260895
0.947 High Similarity NPC308451
0.9467 High Similarity NPC328119
0.9467 High Similarity NPC52005
0.9467 High Similarity NPC48479
0.9467 High Similarity NPC181250
0.9467 High Similarity NPC177298
0.9467 High Similarity NPC216318
0.9467 High Similarity NPC259713
0.9467 High Similarity NPC69752
0.9467 High Similarity NPC183950
0.9467 High Similarity NPC195351
0.9467 High Similarity NPC87125
0.9467 High Similarity NPC17286
0.9467 High Similarity NPC270465
0.9467 High Similarity NPC137062
0.9467 High Similarity NPC159103
0.9467 High Similarity NPC223579
0.9467 High Similarity NPC296197
0.9467 High Similarity NPC287101
0.943 High Similarity NPC295082
0.943 High Similarity NPC158761
0.943 High Similarity NPC470456
0.9419 High Similarity NPC263449
0.9419 High Similarity NPC476980
0.9416 High Similarity NPC471479
0.9416 High Similarity NPC78225
0.9416 High Similarity NPC474836
0.9416 High Similarity NPC472910
0.9416 High Similarity NPC471515
0.9416 High Similarity NPC222814
0.9416 High Similarity NPC174908
0.9416 High Similarity NPC472913
0.9416 High Similarity NPC48208
0.9416 High Similarity NPC472914
0.9416 High Similarity NPC96167
0.9416 High Similarity NPC156057
0.9416 High Similarity NPC162869
0.9416 High Similarity NPC472911
0.9416 High Similarity NPC245758

  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 NPC300943 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
0.9733 High Similarity NPD2801 Approved
0.9351 High Similarity NPD3882 Suspended
0.9286 High Similarity NPD3817 Phase 2
0.9267 High Similarity NPD1512 Approved
0.9156 High Similarity NPD1934 Approved
0.9141 High Similarity NPD4338 Clinical (unspecified phase)
0.9133 High Similarity NPD1511 Approved
0.9062 High Similarity NPD6166 Phase 2
0.9062 High Similarity NPD6168 Clinical (unspecified phase)
0.9062 High Similarity NPD6167 Clinical (unspecified phase)
0.8974 High Similarity NPD2393 Clinical (unspecified phase)
0.8902 High Similarity NPD6797 Phase 2
0.8848 High Similarity NPD7251 Discontinued
0.8834 High Similarity NPD3818 Discontinued
0.8824 High Similarity NPD4378 Clinical (unspecified phase)
0.8795 High Similarity NPD7808 Phase 3
0.878 High Similarity NPD7054 Approved
0.8727 High Similarity NPD7472 Approved
0.8679 High Similarity NPD5402 Approved
0.8614 High Similarity NPD7074 Phase 3
0.8571 High Similarity NPD7075 Discontinued
0.8516 High Similarity NPD6799 Approved
0.8509 High Similarity NPD4868 Clinical (unspecified phase)
0.8466 Intermediate Similarity NPD5494 Approved
0.8438 Intermediate Similarity NPD6801 Discontinued
0.8428 Intermediate Similarity NPD4380 Phase 2
0.8415 Intermediate Similarity NPD1247 Approved
0.8385 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8364 Intermediate Similarity NPD6232 Discontinued
0.8344 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD7473 Discontinued
0.8247 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8247 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD5403 Approved
0.8235 Intermediate Similarity NPD1510 Phase 2
0.8235 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8228 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8204 Intermediate Similarity NPD3926 Phase 2
0.8199 Intermediate Similarity NPD6599 Discontinued
0.8194 Intermediate Similarity NPD1549 Phase 2
0.8182 Intermediate Similarity NPD2796 Approved
0.816 Intermediate Similarity NPD1465 Phase 2
0.8113 Intermediate Similarity NPD5401 Approved
0.8092 Intermediate Similarity NPD943 Approved
0.8092 Intermediate Similarity NPD1240 Approved
0.8072 Intermediate Similarity NPD919 Approved
0.8049 Intermediate Similarity NPD7819 Suspended
0.8012 Intermediate Similarity NPD5844 Phase 1
0.8 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD1607 Approved
0.7962 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7927 Intermediate Similarity NPD7411 Suspended
0.7925 Intermediate Similarity NPD6190 Approved
0.7885 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD6959 Discontinued
0.7834 Intermediate Similarity NPD2935 Discontinued
0.7829 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7806 Intermediate Similarity NPD230 Phase 1
0.7806 Intermediate Similarity NPD447 Suspended
0.7791 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD6559 Discontinued
0.7763 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD3750 Approved
0.7746 Intermediate Similarity NPD3751 Discontinued
0.7744 Intermediate Similarity NPD1653 Approved
0.7742 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD1613 Approved
0.7719 Intermediate Similarity NPD3787 Discontinued
0.7688 Intermediate Similarity NPD2800 Approved
0.768 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD3027 Phase 3
0.763 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD1551 Phase 2
0.7598 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD3749 Approved
0.7561 Intermediate Similarity NPD2534 Approved
0.7561 Intermediate Similarity NPD2532 Approved
0.7561 Intermediate Similarity NPD2533 Approved
0.7558 Intermediate Similarity NPD7199 Phase 2
0.7544 Intermediate Similarity NPD6234 Discontinued
0.7532 Intermediate Similarity NPD9494 Approved
0.7531 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD7768 Phase 2
0.75 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD3226 Approved
0.747 Intermediate Similarity NPD920 Approved
0.7469 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD1933 Approved
0.7453 Intermediate Similarity NPD2344 Approved
0.7452 Intermediate Similarity NPD6233 Phase 2
0.7438 Intermediate Similarity NPD3748 Approved
0.7423 Intermediate Similarity NPD4628 Phase 3
0.7421 Intermediate Similarity NPD6651 Approved
0.7419 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD5953 Discontinued
0.7391 Intermediate Similarity NPD6100 Approved
0.7391 Intermediate Similarity NPD6099 Approved
0.7389 Intermediate Similarity NPD2313 Discontinued
0.7374 Intermediate Similarity NPD7685 Pre-registration
0.7363 Intermediate Similarity NPD8434 Phase 2
0.7362 Intermediate Similarity NPD1243 Approved
0.7353 Intermediate Similarity NPD37 Approved
0.7349 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD2403 Approved
0.7329 Intermediate Similarity NPD2799 Discontinued
0.7329 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD4966 Approved
0.7326 Intermediate Similarity NPD4965 Approved
0.7326 Intermediate Similarity NPD4967 Phase 2
0.7303 Intermediate Similarity NPD7286 Phase 2
0.7302 Intermediate Similarity NPD6779 Approved
0.7302 Intermediate Similarity NPD6782 Approved
0.7302 Intermediate Similarity NPD6777 Approved
0.7302 Intermediate Similarity NPD6776 Approved
0.7302 Intermediate Similarity NPD6780 Approved
0.7302 Intermediate Similarity NPD6778 Approved
0.7302 Intermediate Similarity NPD6781 Approved
0.729 Intermediate Similarity NPD1203 Approved
0.7289 Intermediate Similarity NPD7390 Discontinued
0.7278 Intermediate Similarity NPD6798 Discontinued
0.7277 Intermediate Similarity NPD7435 Discontinued
0.7273 Intermediate Similarity NPD2309 Approved
0.7261 Intermediate Similarity NPD6832 Phase 2
0.7251 Intermediate Similarity NPD6844 Discontinued
0.7247 Intermediate Similarity NPD7228 Approved
0.7239 Intermediate Similarity NPD2346 Discontinued
0.7232 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD1548 Phase 1
0.7208 Intermediate Similarity NPD9269 Phase 2
0.7197 Intermediate Similarity NPD3018 Phase 2
0.7175 Intermediate Similarity NPD5242 Approved
0.7174 Intermediate Similarity NPD8150 Discontinued
0.717 Intermediate Similarity NPD3268 Approved
0.7152 Intermediate Similarity NPD4908 Phase 1
0.7143 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6355 Discontinued
0.7143 Intermediate Similarity NPD422 Phase 1
0.7134 Intermediate Similarity NPD2798 Approved
0.7117 Intermediate Similarity NPD7033 Discontinued
0.7108 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD8313 Approved
0.7104 Intermediate Similarity NPD8312 Approved
0.7098 Intermediate Similarity NPD7697 Approved
0.7098 Intermediate Similarity NPD7698 Approved
0.7098 Intermediate Similarity NPD7696 Phase 3
0.7097 Intermediate Similarity NPD9717 Approved
0.7093 Intermediate Similarity NPD6385 Approved
0.7093 Intermediate Similarity NPD6386 Approved
0.7083 Intermediate Similarity NPD4357 Discontinued
0.7081 Intermediate Similarity NPD4060 Phase 1
0.707 Intermediate Similarity NPD2797 Approved
0.7069 Intermediate Similarity NPD5353 Approved
0.7066 Intermediate Similarity NPD2354 Approved
0.7063 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD7871 Phase 2
0.7062 Intermediate Similarity NPD7870 Phase 2
0.7056 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD2163 Approved
0.7056 Intermediate Similarity NPD7874 Approved
0.7051 Intermediate Similarity NPD2982 Phase 2
0.7051 Intermediate Similarity NPD2983 Phase 2
0.7048 Intermediate Similarity NPD2654 Approved
0.7041 Intermediate Similarity NPD7701 Phase 2
0.7039 Intermediate Similarity NPD5536 Phase 2
0.7037 Intermediate Similarity NPD4363 Phase 3
0.7037 Intermediate Similarity NPD4360 Phase 2
0.7037 Intermediate Similarity NPD6534 Approved
0.7037 Intermediate Similarity NPD6535 Approved
0.7032 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD1610 Phase 2
0.703 Intermediate Similarity NPD1471 Phase 3
0.7022 Intermediate Similarity NPD5710 Approved
0.7022 Intermediate Similarity NPD5711 Approved
0.7012 Intermediate Similarity NPD4308 Phase 3
0.7006 Intermediate Similarity NPD3225 Approved
0.7 Intermediate Similarity NPD7095 Approved
0.699 Remote Similarity NPD7584 Approved
0.6987 Remote Similarity NPD1608 Approved
0.6987 Remote Similarity NPD2981 Phase 2
0.6981 Remote Similarity NPD2861 Phase 2
0.6961 Remote Similarity NPD7907 Approved
0.6957 Remote Similarity NPD411 Approved
0.6957 Remote Similarity NPD7549 Discontinued
0.6948 Remote Similarity NPD9268 Approved
0.6946 Remote Similarity NPD2899 Discontinued
0.6946 Remote Similarity NPD1652 Phase 2
0.6941 Remote Similarity NPD3146 Approved
0.6941 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6941 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6935 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6935 Remote Similarity NPD7801 Approved

  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