Structure

Physi-Chem Properties

Molecular Weight:  460.1
Volume:  427.807
LogP:  1.758
LogD:  0.935
LogS:  -4.145
# Rotatable Bonds:  5
TPSA:  176.12
# H-Bond Aceptor:  11
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.357
Synthetic Accessibility Score:  3.897
Fsp3:  0.273
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.246
MDCK Permeability:  3.1467956432607025e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.116
Human Intestinal Absorption (HIA):  0.195
20% Bioavailability (F20%):  0.012
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.053
Plasma Protein Binding (PPB):  81.2128677368164%
Volume Distribution (VD):  0.64
Pgp-substrate:  12.257124900817871%

ADMET: Metabolism

CYP1A2-inhibitor:  0.046
CYP1A2-substrate:  0.1
CYP2C19-inhibitor:  0.028
CYP2C19-substrate:  0.062
CYP2C9-inhibitor:  0.016
CYP2C9-substrate:  0.349
CYP2D6-inhibitor:  0.014
CYP2D6-substrate:  0.136
CYP3A4-inhibitor:  0.009
CYP3A4-substrate:  0.008

ADMET: Excretion

Clearance (CL):  0.99
Half-life (T1/2):  0.796

ADMET: Toxicity

hERG Blockers:  0.045
Human Hepatotoxicity (H-HT):  0.16
Drug-inuced Liver Injury (DILI):  0.985
AMES Toxicity:  0.124
Rat Oral Acute Toxicity:  0.042
Maximum Recommended Daily Dose:  0.004
Skin Sensitization:  0.07
Carcinogencity:  0.115
Eye Corrosion:  0.003
Eye Irritation:  0.018
Respiratory Toxicity:  0.04

Download Data

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  Natural Product: NPC264735

Natural Product ID:  NPC264735
Common Name*:   Wogonin 7-O-Glucuronide
IUPAC Name:   (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(5-hydroxy-8-methoxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid
Synonyms:   Wogonin 7-O-Glucuronide
Standard InCHIKey:  LNOHXHDWGCMVCO-NTKSAMNMSA-N
Standard InCHI:  InChI=1S/C22H20O11/c1-30-18-13(32-22-17(27)15(25)16(26)20(33-22)21(28)29)8-11(24)14-10(23)7-12(31-19(14)18)9-5-3-2-4-6-9/h2-8,15-17,20,22,24-27H,1H3,(H,28,29)/p-1/t15-,16-,17+,20-,22+/m0/s1
SMILES:  COc1c(cc(c2c(=O)cc(c3ccccc3)oc12)[O-])O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464732
PubChem CID:   3084961
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0002934] Flavonoid O-glucuronides
              • [CHEMONTID:0003534] Flavonoid-7-O-glucuronides

*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
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. leaf n.a. PMID[15894448]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. root n.a. PMID[15894448]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota aerial parts purchased in Juhuacun herbal market, Kunming, Yunnan Province, China 2002-Oct PMID[16562826]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[18357994]
NPO11748 Eunicea knighti Species Plexauridae Eukaryota n.a. Santa Marta Bay, Colombian Caribbean 2007-MAY PMID[19778088]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19829679]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. root n.a. PMID[21087019]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. leaf n.a. PMID[21598983]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. leaf n.a. PMID[22026410]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[22314230]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23521110]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota roots n.a. n.a. PMID[26259802]
NPO17543 Stizophyllum riparium Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[3598599]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. kernel n.a. PMID[7092570]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[8377022]
NPO29667 Scutellariae radix n.a. n.a. n.a. n.a. n.a. n.a. PMID[9214730]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[9834167]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO14992 Prunus persica Species Rosaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3107 Bupleurum falcatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3107 Bupleurum falcatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3107 Bupleurum falcatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3107 Bupleurum falcatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25238 Rheum coreanum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11748 Eunicea knighti Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15658 Utricularia vulgaris Species Lentibulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16610 Chromodoris hamiltoni Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17543 Stizophyllum riparium Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3107 Bupleurum falcatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14691.1 Crambe hispanica subsp. abyssinica Subspecies Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16730 Helichrysum lindleyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25238 Rheum coreanum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3578 Andrographis paniculata Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28877 Scutellaria baicalensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14992 Prunus persica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26084 Vincetoxicum amplexicaule Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17023 Cusparia macrocarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3962 Parinari campestris Species Chrysobalanaceae 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
NPT1644 Protein Family Trypsin Homo sapiens IC50 > 1000000.0 nM PMID[568410]
NPT21762 SINGLE PROTEIN Lysine-specific histone demethylase 1 Homo sapiens IC50 = 2980.0 nM PMID[568411]

☑ 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 NPC264735 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
0.9939 High Similarity NPC198324
0.9939 High Similarity NPC472385
0.9877 High Similarity NPC101191
0.9877 High Similarity NPC49344
0.9877 High Similarity NPC135277
0.9877 High Similarity NPC477848
0.9877 High Similarity NPC43211
0.9877 High Similarity NPC115760
0.9877 High Similarity NPC210094
0.9877 High Similarity NPC237435
0.9817 High Similarity NPC211532
0.9817 High Similarity NPC472380
0.9817 High Similarity NPC472384
0.9817 High Similarity NPC233994
0.9817 High Similarity NPC472382
0.9816 High Similarity NPC4390
0.9816 High Similarity NPC101026
0.9816 High Similarity NPC24043
0.9816 High Similarity NPC169977
0.9816 High Similarity NPC42773
0.9816 High Similarity NPC45522
0.9816 High Similarity NPC21666
0.9755 High Similarity NPC172807
0.9755 High Similarity NPC254540
0.9755 High Similarity NPC211594
0.9755 High Similarity NPC476405
0.9755 High Similarity NPC117260
0.9755 High Similarity NPC175107
0.9755 High Similarity NPC190003
0.9755 High Similarity NPC153755
0.9701 High Similarity NPC36138
0.9701 High Similarity NPC470446
0.9701 High Similarity NPC470445
0.9701 High Similarity NPC470447
0.9701 High Similarity NPC470449
0.9697 High Similarity NPC268533
0.9693 High Similarity NPC20505
0.9693 High Similarity NPC245014
0.9693 High Similarity NPC282987
0.9693 High Similarity NPC84265
0.9693 High Similarity NPC244776
0.9693 High Similarity NPC116864
0.9693 High Similarity NPC235260
0.9693 High Similarity NPC155763
0.9643 High Similarity NPC470451
0.9643 High Similarity NPC470455
0.9643 High Similarity NPC470416
0.9641 High Similarity NPC222674
0.9639 High Similarity NPC168584
0.9634 High Similarity NPC472386
0.9632 High Similarity NPC138927
0.9632 High Similarity NPC201292
0.9632 High Similarity NPC475942
0.9632 High Similarity NPC105025
0.9632 High Similarity NPC93337
0.9632 High Similarity NPC186807
0.9632 High Similarity NPC225434
0.9632 High Similarity NPC469931
0.9632 High Similarity NPC45638
0.9632 High Similarity NPC219904
0.9632 High Similarity NPC223747
0.9632 High Similarity NPC226294
0.9632 High Similarity NPC120099
0.9632 High Similarity NPC203050
0.9632 High Similarity NPC58053
0.9583 High Similarity NPC107987
0.9581 High Similarity NPC241423
0.9581 High Similarity NPC473682
0.9581 High Similarity NPC473571
0.9581 High Similarity NPC470443
0.9581 High Similarity NPC126784
0.9581 High Similarity NPC470444
0.9581 High Similarity NPC110941
0.9578 High Similarity NPC169733
0.9578 High Similarity NPC65563
0.9578 High Similarity NPC8573
0.9578 High Similarity NPC470949
0.9573 High Similarity NPC105511
0.9573 High Similarity NPC206123
0.9571 High Similarity NPC127546
0.9571 High Similarity NPC265530
0.9571 High Similarity NPC173637
0.9571 High Similarity NPC146792
0.9571 High Similarity NPC45618
0.9571 High Similarity NPC317489
0.9571 High Similarity NPC325555
0.9571 High Similarity NPC223424
0.9571 High Similarity NPC84362
0.9571 High Similarity NPC52550
0.9571 High Similarity NPC226304
0.9571 High Similarity NPC58716
0.9524 High Similarity NPC473071
0.9524 High Similarity NPC473073
0.9521 High Similarity NPC35167
0.9521 High Similarity NPC173837
0.9521 High Similarity NPC477895
0.9521 High Similarity NPC217520
0.9521 High Similarity NPC139571
0.9518 High Similarity NPC253685
0.9515 High Similarity NPC205076
0.9515 High Similarity NPC48773
0.9515 High Similarity NPC307518
0.9512 High Similarity NPC472381
0.9512 High Similarity NPC472383
0.9509 High Similarity NPC179950
0.9509 High Similarity NPC135599
0.9509 High Similarity NPC88789
0.9509 High Similarity NPC56077
0.9509 High Similarity NPC281131
0.9509 High Similarity NPC276222
0.9509 High Similarity NPC253662
0.9509 High Similarity NPC21100
0.9509 High Similarity NPC308404
0.9509 High Similarity NPC328940
0.9509 High Similarity NPC118284
0.9509 High Similarity NPC113968
0.9509 High Similarity NPC274618
0.9509 High Similarity NPC197285
0.9509 High Similarity NPC277174
0.9509 High Similarity NPC145038
0.9509 High Similarity NPC73855
0.9506 High Similarity NPC88023
0.9506 High Similarity NPC309025
0.9506 High Similarity NPC243930
0.9467 High Similarity NPC473072
0.9461 High Similarity NPC61904
0.9461 High Similarity NPC89127
0.9461 High Similarity NPC471669
0.9461 High Similarity NPC472991
0.9461 High Similarity NPC144097
0.9461 High Similarity NPC472992
0.9458 High Similarity NPC204693
0.9455 High Similarity NPC224462
0.9455 High Similarity NPC183357
0.9455 High Similarity NPC21190
0.9455 High Similarity NPC95866
0.9455 High Similarity NPC22195
0.9455 High Similarity NPC44558
0.9451 High Similarity NPC93099
0.9451 High Similarity NPC116745
0.9451 High Similarity NPC135345
0.9448 High Similarity NPC277205
0.9448 High Similarity NPC311830
0.9448 High Similarity NPC22832
0.9448 High Similarity NPC19388
0.9448 High Similarity NPC55786
0.9448 High Similarity NPC240431
0.9444 High Similarity NPC27942
0.9412 High Similarity NPC148710
0.9405 High Similarity NPC293626
0.9405 High Similarity NPC267680
0.9405 High Similarity NPC37668
0.9405 High Similarity NPC253521
0.9405 High Similarity NPC217387
0.9405 High Similarity NPC196127
0.9405 High Similarity NPC113836
0.9405 High Similarity NPC258044
0.9405 High Similarity NPC472387
0.9401 High Similarity NPC476472
0.9401 High Similarity NPC34267
0.9401 High Similarity NPC214621
0.9401 High Similarity NPC223426
0.9401 High Similarity NPC81042
0.9401 High Similarity NPC16194
0.9401 High Similarity NPC294815
0.9401 High Similarity NPC473327
0.9401 High Similarity NPC220173
0.9401 High Similarity NPC19108
0.9398 High Similarity NPC26230
0.9398 High Similarity NPC60735
0.9398 High Similarity NPC176740
0.9398 High Similarity NPC134532
0.9398 High Similarity NPC33054
0.9398 High Similarity NPC155877
0.9398 High Similarity NPC3583
0.9398 High Similarity NPC203259
0.9398 High Similarity NPC471725
0.9398 High Similarity NPC267254
0.9398 High Similarity NPC471748
0.9398 High Similarity NPC259152
0.9398 High Similarity NPC245452
0.9394 High Similarity NPC210042
0.9394 High Similarity NPC471457
0.9394 High Similarity NPC52382
0.9394 High Similarity NPC170675
0.9394 High Similarity NPC112755
0.9394 High Similarity NPC95855
0.9394 High Similarity NPC270578
0.939 High Similarity NPC99957
0.939 High Similarity NPC181616
0.9387 High Similarity NPC94777
0.9387 High Similarity NPC270335
0.9387 High Similarity NPC284960
0.9387 High Similarity NPC191306
0.9387 High Similarity NPC19709
0.9387 High Similarity NPC222936
0.9383 High Similarity NPC216496
0.9383 High Similarity NPC159579
0.9383 High Similarity NPC224530
0.9383 High Similarity NPC182045

  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 NPC264735 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
0.9877 High Similarity NPD4338 Clinical (unspecified phase)
0.9401 High Similarity NPD7808 Phase 3
0.9398 High Similarity NPD6797 Phase 2
0.9341 High Similarity NPD7251 Discontinued
0.9277 High Similarity NPD7054 Approved
0.9222 High Similarity NPD7472 Approved
0.9107 High Similarity NPD7074 Phase 3
0.9102 High Similarity NPD3818 Discontinued
0.9074 High Similarity NPD3817 Phase 2
0.8963 High Similarity NPD4381 Clinical (unspecified phase)
0.8935 High Similarity NPD7804 Clinical (unspecified phase)
0.8896 High Similarity NPD2801 Approved
0.8869 High Similarity NPD6168 Clinical (unspecified phase)
0.8869 High Similarity NPD6167 Clinical (unspecified phase)
0.8869 High Similarity NPD6166 Phase 2
0.8841 High Similarity NPD5402 Approved
0.872 High Similarity NPD1934 Approved
0.8675 High Similarity NPD3882 Suspended
0.8623 High Similarity NPD7075 Discontinued
0.8563 High Similarity NPD4868 Clinical (unspecified phase)
0.8554 High Similarity NPD2393 Clinical (unspecified phase)
0.8494 Intermediate Similarity NPD6801 Discontinued
0.8466 Intermediate Similarity NPD1512 Approved
0.8444 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8443 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8415 Intermediate Similarity NPD5403 Approved
0.84 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8373 Intermediate Similarity NPD4380 Phase 2
0.8364 Intermediate Similarity NPD1653 Approved
0.8352 Intermediate Similarity NPD6559 Discontinued
0.8344 Intermediate Similarity NPD6799 Approved
0.8344 Intermediate Similarity NPD1511 Approved
0.8304 Intermediate Similarity NPD5494 Approved
0.8293 Intermediate Similarity NPD5401 Approved
0.8286 Intermediate Similarity NPD5844 Phase 1
0.8182 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD3751 Discontinued
0.8103 Intermediate Similarity NPD3787 Discontinued
0.8103 Intermediate Similarity NPD6232 Discontinued
0.8068 Intermediate Similarity NPD7473 Discontinued
0.8057 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD6599 Discontinued
0.8045 Intermediate Similarity NPD7685 Pre-registration
0.8012 Intermediate Similarity NPD1465 Phase 2
0.8012 Intermediate Similarity NPD7819 Suspended
0.8 Intermediate Similarity NPD7435 Discontinued
0.8 Intermediate Similarity NPD7411 Suspended
0.7976 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7967 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7943 Intermediate Similarity NPD7199 Phase 2
0.7943 Intermediate Similarity NPD1247 Approved
0.7935 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD919 Approved
0.7927 Intermediate Similarity NPD1549 Phase 2
0.7921 Intermediate Similarity NPD7228 Approved
0.7892 Intermediate Similarity NPD6190 Approved
0.7861 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD8312 Approved
0.7857 Intermediate Similarity NPD8313 Approved
0.7849 Intermediate Similarity NPD37 Approved
0.7842 Intermediate Similarity NPD6781 Approved
0.7842 Intermediate Similarity NPD6778 Approved
0.7842 Intermediate Similarity NPD6782 Approved
0.7842 Intermediate Similarity NPD6777 Approved
0.7842 Intermediate Similarity NPD6779 Approved
0.7842 Intermediate Similarity NPD6776 Approved
0.7842 Intermediate Similarity NPD6780 Approved
0.7831 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD6234 Discontinued
0.7816 Intermediate Similarity NPD4966 Approved
0.7816 Intermediate Similarity NPD4965 Approved
0.7816 Intermediate Similarity NPD4967 Phase 2
0.7805 Intermediate Similarity NPD2796 Approved
0.7755 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7755 Intermediate Similarity NPD7874 Approved
0.7751 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD1510 Phase 2
0.774 Intermediate Similarity NPD6959 Discontinued
0.7711 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7709 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD1933 Approved
0.7654 Intermediate Similarity NPD3926 Phase 2
0.7651 Intermediate Similarity NPD7266 Discontinued
0.7629 Intermediate Similarity NPD7697 Approved
0.7629 Intermediate Similarity NPD7696 Phase 3
0.7629 Intermediate Similarity NPD7698 Approved
0.7626 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7626 Intermediate Similarity NPD7783 Phase 2
0.7619 Intermediate Similarity NPD3750 Approved
0.7614 Intermediate Similarity NPD8151 Discontinued
0.7592 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD7870 Phase 2
0.759 Intermediate Similarity NPD2935 Discontinued
0.759 Intermediate Similarity NPD7871 Phase 2
0.7579 Intermediate Similarity NPD6535 Approved
0.7579 Intermediate Similarity NPD6534 Approved
0.7571 Intermediate Similarity NPD3749 Approved
0.7563 Intermediate Similarity NPD7701 Phase 2
0.7561 Intermediate Similarity NPD447 Suspended
0.7561 Intermediate Similarity NPD230 Phase 1
0.7554 Intermediate Similarity NPD7240 Approved
0.7515 Intermediate Similarity NPD4628 Phase 3
0.7514 Intermediate Similarity NPD7768 Phase 2
0.7513 Intermediate Similarity NPD7584 Approved
0.75 Intermediate Similarity NPD1240 Approved
0.75 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD8455 Phase 2
0.75 Intermediate Similarity NPD1613 Approved
0.7485 Intermediate Similarity NPD1551 Phase 2
0.7485 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7461 Intermediate Similarity NPD7700 Phase 2
0.7461 Intermediate Similarity NPD7699 Phase 2
0.745 Intermediate Similarity NPD7801 Approved
0.7447 Intermediate Similarity NPD8434 Phase 2
0.7447 Intermediate Similarity NPD8150 Discontinued
0.7442 Intermediate Similarity NPD2534 Approved
0.7442 Intermediate Similarity NPD2533 Approved
0.7442 Intermediate Similarity NPD2532 Approved
0.7439 Intermediate Similarity NPD6233 Phase 2
0.7411 Intermediate Similarity NPD8320 Phase 1
0.7411 Intermediate Similarity NPD8319 Approved
0.741 Intermediate Similarity NPD1607 Approved
0.7398 Intermediate Similarity NPD6823 Phase 2
0.7394 Intermediate Similarity NPD943 Approved
0.7379 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD920 Approved
0.7353 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7322 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD3748 Approved
0.7317 Intermediate Similarity NPD3027 Phase 3
0.7312 Intermediate Similarity NPD5953 Discontinued
0.73 Intermediate Similarity NPD7585 Approved
0.7273 Intermediate Similarity NPD3226 Approved
0.7273 Intermediate Similarity NPD6798 Discontinued
0.7256 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD7583 Approved
0.7247 Intermediate Similarity NPD6844 Discontinued
0.7241 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7033 Discontinued
0.7219 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD7286 Phase 2
0.7195 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD7458 Discontinued
0.7169 Intermediate Similarity NPD2313 Discontinued
0.7167 Intermediate Similarity NPD5353 Approved
0.7165 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD6213 Phase 3
0.7165 Intermediate Similarity NPD6212 Phase 3
0.7157 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6832 Phase 2
0.7151 Intermediate Similarity NPD1652 Phase 2
0.7151 Intermediate Similarity NPD2800 Approved
0.7151 Intermediate Similarity NPD1243 Approved
0.7143 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6355 Discontinued
0.7135 Intermediate Similarity NPD2346 Discontinued
0.7126 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD2799 Discontinued
0.71 Intermediate Similarity NPD7680 Approved
0.7081 Intermediate Similarity NPD5242 Approved
0.7073 Intermediate Similarity NPD1203 Approved
0.7053 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD7549 Discontinued
0.7052 Intermediate Similarity NPD6674 Discontinued
0.705 Intermediate Similarity NPD5006 Approved
0.705 Intermediate Similarity NPD5005 Approved
0.7041 Intermediate Similarity NPD4360 Phase 2
0.7041 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD5124 Phase 1
0.7041 Intermediate Similarity NPD4363 Phase 3
0.7041 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD1091 Approved
0.703 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD5710 Approved
0.7027 Intermediate Similarity NPD5711 Approved
0.7011 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6385 Approved
0.7 Intermediate Similarity NPD6386 Approved
0.6988 Remote Similarity NPD9494 Approved
0.6983 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6982 Remote Similarity NPD4060 Phase 1
0.6977 Remote Similarity NPD6100 Approved
0.6977 Remote Similarity NPD6099 Approved
0.6973 Remote Similarity NPD8127 Discontinued
0.6964 Remote Similarity NPD3268 Approved
0.6946 Remote Similarity NPD4908 Phase 1
0.6936 Remote Similarity NPD2344 Approved
0.6935 Remote Similarity NPD4420 Approved
0.6933 Remote Similarity NPD422 Phase 1
0.6928 Remote Similarity NPD2798 Approved
0.6923 Remote Similarity NPD7930 Approved
0.6923 Remote Similarity NPD4062 Phase 3
0.6911 Remote Similarity NPD7038 Approved
0.6911 Remote Similarity NPD7039 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