Structure

Physi-Chem Properties

Molecular Weight:  339.15
Volume:  353.873
LogP:  3.688
LogD:  3.513
LogS:  -4.584
# Rotatable Bonds:  5
TPSA:  71.55
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.707
Synthetic Accessibility Score:  2.732
Fsp3:  0.25
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:  -4.889
MDCK Permeability:  1.5155012079048902e-05
Pgp-inhibitor:  0.911
Pgp-substrate:  0.439
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.864
Plasma Protein Binding (PPB):  86.18091583251953%
Volume Distribution (VD):  0.792
Pgp-substrate:  9.936007499694824%

ADMET: Metabolism

CYP1A2-inhibitor:  0.974
CYP1A2-substrate:  0.949
CYP2C19-inhibitor:  0.955
CYP2C19-substrate:  0.495
CYP2C9-inhibitor:  0.867
CYP2C9-substrate:  0.956
CYP2D6-inhibitor:  0.836
CYP2D6-substrate:  0.873
CYP3A4-inhibitor:  0.858
CYP3A4-substrate:  0.419

ADMET: Excretion

Clearance (CL):  6.833
Half-life (T1/2):  0.514

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.439
Drug-inuced Liver Injury (DILI):  0.914
AMES Toxicity:  0.497
Rat Oral Acute Toxicity:  0.095
Maximum Recommended Daily Dose:  0.7
Skin Sensitization:  0.838
Carcinogencity:  0.33
Eye Corrosion:  0.008
Eye Irritation:  0.89
Respiratory Toxicity:  0.914

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

  Natural Product: NPC274618

Natural Product ID:  NPC274618
Common Name*:   Quercetine-3-O-Beta-L-Arabinoside
IUPAC Name:   2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one
Synonyms:  
Standard InCHIKey:  PZZRDJXEMZMZFD-VHICIVCISA-N
Standard InCHI:  InChI=1S/C20H18O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17,20-26,28H,6H2/t12-,15-,17+,20+/m1/s1
SMILES:  Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1OC[C@H]([C@H]([C@@H]1O)O)O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL520637
PubChem CID:   21722017
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003531] Flavonoid-3-O-glycosides

*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
NPO19369 Bacillus thuringiensis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[11087590]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[11421757]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[11975480]
NPO11713 Hypericum scabrum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[15568778]
NPO11713 Hypericum scabrum Species Hypericaceae Eukaryota n.a. Uzbekistan n.a. PMID[15568778]
NPO10729 Lechevalieria aerocolonigenes Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. PMID[15620255]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[15974621]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota leaves Krachong waterfall area, Trang Province, Thailand 2001-APR PMID[15974621]
NPO3453 Elaeocarpus fuscoides Species Elaeocarpaceae Eukaryota leaves n.a. n.a. PMID[17451272]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota leaves n.a. n.a. PMID[18844422]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[18844422]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota epidermis of the sclerotia n.a. n.a. PMID[19746919]
NPO11713 Hypericum scabrum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[27280968]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[27808511]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[28972755]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[8984162]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8543 Meconopsis horridula Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1209 Swartzia madagascariensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12330 Pseudophryne coriacea Species Myobatrachidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5711 Streptomyces libani Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11713 Hypericum scabrum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3280 Penicillium crustaceum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10729 Lechevalieria aerocolonigenes Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19369 Bacillus thuringiensis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO840 Anacyclus tomentosus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO477 Lepraria xanthina Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO305 Vitex pinnata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7087 Oxera splendida Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8543 Meconopsis horridula Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9168 Sidastrum paniculatum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6558 Licania pittieri Species Chrysobalanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1722 Hippospongia communis Species Spongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1209 Swartzia madagascariensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11564 Ruditapes philippinarum Species Veneridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3453 Elaeocarpus fuscoides Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5508 Stevia purpurea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15164 Jacobaea adonidifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14791 Briareum violacea Species Briareidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO896 Streptomyces kanamyceticus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6271 Solanum giganteum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5344 Calodendrum capense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9472 Ixeris tamagawaensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6330 Croton caudatus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5864 Ungnadia speciosa Species Sapindaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 > 20000.0 ug.mL-1 PMID[506839]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 20000.0 ug.mL-1 PMID[506839]
NPT81 Cell Line A549 Homo sapiens Inhibition = 11.0 % PMID[506839]
NPT83 Cell Line MCF7 Homo sapiens Inhibition = 17.0 % PMID[506839]

☑ 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 NPC274618 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 NPC253662
1.0 High Similarity NPC179950
1.0 High Similarity NPC88789
1.0 High Similarity NPC145038
1.0 High Similarity NPC281131
1.0 High Similarity NPC118284
1.0 High Similarity NPC308404
1.0 High Similarity NPC276222
1.0 High Similarity NPC56077
0.9936 High Similarity NPC127546
0.9936 High Similarity NPC52550
0.9936 High Similarity NPC19388
0.9936 High Similarity NPC223424
0.9936 High Similarity NPC84362
0.9936 High Similarity NPC173637
0.9936 High Similarity NPC277205
0.9936 High Similarity NPC240431
0.9936 High Similarity NPC317489
0.9936 High Similarity NPC55786
0.9873 High Similarity NPC328940
0.9873 High Similarity NPC73855
0.9873 High Similarity NPC219904
0.9873 High Similarity NPC120099
0.9873 High Similarity NPC203050
0.9873 High Similarity NPC21100
0.9873 High Similarity NPC223747
0.9873 High Similarity NPC135599
0.9873 High Similarity NPC113968
0.9873 High Similarity NPC277174
0.9873 High Similarity NPC197285
0.9873 High Similarity NPC225434
0.9811 High Similarity NPC136042
0.9811 High Similarity NPC155763
0.9811 High Similarity NPC20505
0.9811 High Similarity NPC95866
0.9811 High Similarity NPC254855
0.9811 High Similarity NPC259896
0.9811 High Similarity NPC156869
0.9811 High Similarity NPC235260
0.9811 High Similarity NPC244776
0.9811 High Similarity NPC29958
0.9811 High Similarity NPC255157
0.9811 High Similarity NPC67326
0.9811 High Similarity NPC206123
0.9811 High Similarity NPC116864
0.981 High Similarity NPC226304
0.981 High Similarity NPC325555
0.981 High Similarity NPC160156
0.981 High Similarity NPC92565
0.981 High Similarity NPC265530
0.9808 High Similarity NPC77660
0.9808 High Similarity NPC189142
0.975 High Similarity NPC176740
0.975 High Similarity NPC203259
0.975 High Similarity NPC471748
0.975 High Similarity NPC190003
0.975 High Similarity NPC33054
0.975 High Similarity NPC471725
0.975 High Similarity NPC153755
0.975 High Similarity NPC245452
0.975 High Similarity NPC26230
0.975 High Similarity NPC134532
0.975 High Similarity NPC60735
0.975 High Similarity NPC155877
0.975 High Similarity NPC175107
0.9748 High Similarity NPC52382
0.9748 High Similarity NPC138927
0.9748 High Similarity NPC270578
0.9747 High Similarity NPC67037
0.9747 High Similarity NPC255615
0.9745 High Similarity NPC168822
0.9745 High Similarity NPC270335
0.9745 High Similarity NPC191306
0.9745 High Similarity NPC19709
0.9689 High Similarity NPC101026
0.9689 High Similarity NPC24043
0.9689 High Similarity NPC4390
0.9689 High Similarity NPC45522
0.9689 High Similarity NPC21666
0.9689 High Similarity NPC42773
0.9689 High Similarity NPC169977
0.9688 High Similarity NPC285197
0.9688 High Similarity NPC67105
0.9688 High Similarity NPC245014
0.9688 High Similarity NPC282987
0.9688 High Similarity NPC84265
0.9686 High Similarity NPC149244
0.9686 High Similarity NPC275454
0.9686 High Similarity NPC48640
0.9684 High Similarity NPC311830
0.9684 High Similarity NPC34531
0.9684 High Similarity NPC22832
0.9682 High Similarity NPC473043
0.963 High Similarity NPC214621
0.963 High Similarity NPC294815
0.963 High Similarity NPC237435
0.963 High Similarity NPC473327
0.963 High Similarity NPC115760
0.963 High Similarity NPC220173
0.963 High Similarity NPC253685
0.963 High Similarity NPC81042
0.963 High Similarity NPC19108
0.963 High Similarity NPC101191
0.963 High Similarity NPC476472
0.963 High Similarity NPC135277
0.963 High Similarity NPC294629
0.963 High Similarity NPC223426
0.963 High Similarity NPC16194
0.963 High Similarity NPC49344
0.963 High Similarity NPC34267
0.963 High Similarity NPC210094
0.963 High Similarity NPC43211
0.9627 High Similarity NPC117260
0.9627 High Similarity NPC476405
0.9625 High Similarity NPC227508
0.9623 High Similarity NPC210073
0.9623 High Similarity NPC8856
0.9623 High Similarity NPC115674
0.9623 High Similarity NPC254306
0.962 High Similarity NPC284960
0.962 High Similarity NPC243930
0.962 High Similarity NPC222936
0.962 High Similarity NPC309025
0.962 High Similarity NPC29830
0.962 High Similarity NPC88023
0.9571 High Similarity NPC198324
0.9571 High Similarity NPC202908
0.9571 High Similarity NPC122467
0.9571 High Similarity NPC89127
0.9571 High Similarity NPC292019
0.9571 High Similarity NPC65563
0.9571 High Similarity NPC144097
0.9571 High Similarity NPC8573
0.9571 High Similarity NPC61904
0.9571 High Similarity NPC219043
0.9571 High Similarity NPC470949
0.9571 High Similarity NPC472385
0.9571 High Similarity NPC14187
0.9571 High Similarity NPC471669
0.9565 High Similarity NPC72249
0.9563 High Similarity NPC229729
0.9563 High Similarity NPC58716
0.9563 High Similarity NPC146792
0.9563 High Similarity NPC45618
0.9557 High Similarity NPC300537
0.9557 High Similarity NPC127782
0.9551 High Similarity NPC133671
0.9551 High Similarity NPC135391
0.9551 High Similarity NPC197304
0.9551 High Similarity NPC77672
0.9551 High Similarity NPC54802
0.9551 High Similarity NPC78263
0.9512 High Similarity NPC217520
0.9512 High Similarity NPC251417
0.9512 High Similarity NPC113836
0.9512 High Similarity NPC139571
0.9512 High Similarity NPC35167
0.9512 High Similarity NPC89052
0.9512 High Similarity NPC253521
0.9512 High Similarity NPC168584
0.9512 High Similarity NPC173837
0.9512 High Similarity NPC37668
0.9509 High Similarity NPC264735
0.9509 High Similarity NPC477848
0.9503 High Similarity NPC86008
0.9503 High Similarity NPC45638
0.9503 High Similarity NPC201292
0.9503 High Similarity NPC58053
0.9503 High Similarity NPC105025
0.9503 High Similarity NPC209296
0.9503 High Similarity NPC475942
0.9503 High Similarity NPC476771
0.9503 High Similarity NPC186807
0.9503 High Similarity NPC93337
0.9503 High Similarity NPC195257
0.9503 High Similarity NPC226294
0.9503 High Similarity NPC469931
0.95 High Similarity NPC5778
0.95 High Similarity NPC236934
0.9497 High Similarity NPC88043
0.9494 High Similarity NPC182045
0.949 High Similarity NPC41121
0.949 High Similarity NPC472459
0.949 High Similarity NPC111929
0.949 High Similarity NPC320283
0.9487 High Similarity NPC261866
0.9487 High Similarity NPC307938
0.9487 High Similarity NPC323593
0.9487 High Similarity NPC203500
0.9455 High Similarity NPC470443
0.9455 High Similarity NPC470444
0.9455 High Similarity NPC110941
0.9455 High Similarity NPC241423
0.9455 High Similarity NPC473571
0.9455 High Similarity NPC192539
0.9455 High Similarity NPC473682
0.9455 High Similarity NPC126784
0.9451 High Similarity NPC473862
0.9451 High Similarity NPC154741
0.9451 High Similarity NPC233994

  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 NPC274618 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
0.975 High Similarity NPD6797 Phase 2
0.9689 High Similarity NPD7251 Discontinued
0.963 High Similarity NPD4338 Clinical (unspecified phase)
0.9509 High Similarity NPD7808 Phase 3
0.9503 High Similarity NPD7054 Approved
0.9444 High Similarity NPD7472 Approved
0.9325 High Similarity NPD7074 Phase 3
0.9321 High Similarity NPD3818 Discontinued
0.9304 High Similarity NPD4381 Clinical (unspecified phase)
0.9146 High Similarity NPD7804 Clinical (unspecified phase)
0.908 High Similarity NPD6167 Clinical (unspecified phase)
0.908 High Similarity NPD6166 Phase 2
0.908 High Similarity NPD6168 Clinical (unspecified phase)
0.8938 High Similarity NPD3817 Phase 2
0.8931 High Similarity NPD1934 Approved
0.891 High Similarity NPD1512 Approved
0.8875 High Similarity NPD2393 Clinical (unspecified phase)
0.8782 High Similarity NPD1511 Approved
0.8765 High Similarity NPD3882 Suspended
0.8758 High Similarity NPD2801 Approved
0.8688 High Similarity NPD4380 Phase 2
0.865 High Similarity NPD4868 Clinical (unspecified phase)
0.8598 High Similarity NPD7075 Discontinued
0.8589 High Similarity NPD5402 Approved
0.85 High Similarity NPD5403 Approved
0.848 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8466 Intermediate Similarity NPD6801 Discontinued
0.843 Intermediate Similarity NPD6559 Discontinued
0.8415 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8375 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8375 Intermediate Similarity NPD5401 Approved
0.8313 Intermediate Similarity NPD6799 Approved
0.828 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8228 Intermediate Similarity NPD1549 Phase 2
0.8221 Intermediate Similarity NPD1653 Approved
0.8198 Intermediate Similarity NPD3751 Discontinued
0.8176 Intermediate Similarity NPD3787 Discontinued
0.8111 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8059 Intermediate Similarity NPD5494 Approved
0.8038 Intermediate Similarity NPD1510 Phase 2
0.8036 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD6599 Discontinued
0.7987 Intermediate Similarity NPD2796 Approved
0.7976 Intermediate Similarity NPD7819 Suspended
0.7976 Intermediate Similarity NPD1465 Phase 2
0.7964 Intermediate Similarity NPD7411 Suspended
0.7943 Intermediate Similarity NPD5844 Phase 1
0.7927 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD7685 Pre-registration
0.7907 Intermediate Similarity NPD6959 Discontinued
0.7898 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD1613 Approved
0.7861 Intermediate Similarity NPD6232 Discontinued
0.7853 Intermediate Similarity NPD6190 Approved
0.7831 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD7473 Discontinued
0.7821 Intermediate Similarity NPD8313 Approved
0.7821 Intermediate Similarity NPD8312 Approved
0.7803 Intermediate Similarity NPD7199 Phase 2
0.7791 Intermediate Similarity NPD919 Approved
0.7784 Intermediate Similarity NPD7228 Approved
0.7735 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD7266 Discontinued
0.7713 Intermediate Similarity NPD6776 Approved
0.7713 Intermediate Similarity NPD6779 Approved
0.7713 Intermediate Similarity NPD6780 Approved
0.7713 Intermediate Similarity NPD6781 Approved
0.7713 Intermediate Similarity NPD6782 Approved
0.7713 Intermediate Similarity NPD6777 Approved
0.7713 Intermediate Similarity NPD6778 Approved
0.7701 Intermediate Similarity NPD1247 Approved
0.7688 Intermediate Similarity NPD6234 Discontinued
0.7684 Intermediate Similarity NPD7435 Discontinued
0.7683 Intermediate Similarity NPD3750 Approved
0.7683 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD943 Approved
0.7673 Intermediate Similarity NPD1240 Approved
0.767 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7656 Intermediate Similarity NPD7584 Approved
0.7643 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD3926 Phase 2
0.7609 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD37 Approved
0.758 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD1607 Approved
0.7572 Intermediate Similarity NPD4966 Approved
0.7572 Intermediate Similarity NPD4965 Approved
0.7572 Intermediate Similarity NPD4967 Phase 2
0.7558 Intermediate Similarity NPD8455 Phase 2
0.7553 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD1551 Phase 2
0.7545 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD3749 Approved
0.7516 Intermediate Similarity NPD1933 Approved
0.7516 Intermediate Similarity NPD230 Phase 1
0.75 Intermediate Similarity NPD7696 Phase 3
0.75 Intermediate Similarity NPD7697 Approved
0.75 Intermediate Similarity NPD7698 Approved
0.7487 Intermediate Similarity NPD8151 Discontinued
0.7485 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3027 Phase 3
0.7471 Intermediate Similarity NPD7768 Phase 2
0.747 Intermediate Similarity NPD4628 Phase 3
0.7461 Intermediate Similarity NPD7870 Phase 2
0.7461 Intermediate Similarity NPD7871 Phase 2
0.7449 Intermediate Similarity NPD7874 Approved
0.7449 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD6534 Approved
0.7447 Intermediate Similarity NPD6535 Approved
0.7438 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7701 Phase 2
0.7378 Intermediate Similarity NPD3748 Approved
0.7333 Intermediate Similarity NPD2935 Discontinued
0.733 Intermediate Similarity NPD7699 Phase 2
0.733 Intermediate Similarity NPD7700 Phase 2
0.7323 Intermediate Similarity NPD7783 Phase 2
0.7323 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7323 Intermediate Similarity NPD7801 Approved
0.7322 Intermediate Similarity NPD7240 Approved
0.7308 Intermediate Similarity NPD1091 Approved
0.7305 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD447 Suspended
0.7294 Intermediate Similarity NPD2533 Approved
0.7294 Intermediate Similarity NPD2534 Approved
0.7294 Intermediate Similarity NPD2532 Approved
0.7294 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD8319 Approved
0.7282 Intermediate Similarity NPD8320 Phase 1
0.7278 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD6823 Phase 2
0.7259 Intermediate Similarity NPD7585 Approved
0.7222 Intermediate Similarity NPD6798 Discontinued
0.7219 Intermediate Similarity NPD8434 Phase 2
0.7219 Intermediate Similarity NPD8150 Discontinued
0.7209 Intermediate Similarity NPD920 Approved
0.7208 Intermediate Similarity NPD7583 Approved
0.7202 Intermediate Similarity NPD2800 Approved
0.7193 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD6233 Phase 2
0.7176 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD5953 Discontinued
0.7173 Intermediate Similarity NPD4363 Phase 3
0.7173 Intermediate Similarity NPD4360 Phase 2
0.7169 Intermediate Similarity NPD7033 Discontinued
0.7165 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD6099 Approved
0.7126 Intermediate Similarity NPD3226 Approved
0.7126 Intermediate Similarity NPD7458 Discontinued
0.7126 Intermediate Similarity NPD6100 Approved
0.7125 Intermediate Similarity NPD1203 Approved
0.7117 Intermediate Similarity NPD2313 Discontinued
0.7102 Intermediate Similarity NPD6844 Discontinued
0.7101 Intermediate Similarity NPD6674 Discontinued
0.7101 Intermediate Similarity NPD1652 Phase 2
0.7101 Intermediate Similarity NPD1243 Approved
0.7099 Intermediate Similarity NPD4908 Phase 1
0.7099 Intermediate Similarity NPD6832 Phase 2
0.7091 Intermediate Similarity NPD6355 Discontinued
0.7089 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD2798 Approved
0.7065 Intermediate Similarity NPD7286 Phase 2
0.7051 Intermediate Similarity NPD1548 Phase 1
0.7048 Intermediate Similarity NPD6651 Approved
0.7037 Intermediate Similarity NPD9494 Approved
0.7035 Intermediate Similarity NPD7390 Discontinued
0.7031 Intermediate Similarity NPD6213 Phase 3
0.7031 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD6212 Phase 3
0.7029 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7026 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.6988 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6988 Remote Similarity NPD5124 Phase 1
0.6988 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6982 Remote Similarity NPD2346 Discontinued
0.6982 Remote Similarity NPD2344 Approved
0.6981 Remote Similarity NPD1610 Phase 2
0.697 Remote Similarity NPD7680 Approved
0.6964 Remote Similarity NPD2799 Discontinued
0.6959 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6957 Remote Similarity NPD3225 Approved
0.6937 Remote Similarity NPD9269 Phase 2
0.6928 Remote Similarity NPD4060 Phase 1
0.6927 Remote Similarity NPD5353 Approved
0.6919 Remote Similarity NPD2163 Approved
0.6909 Remote Similarity NPD3268 Approved
0.6902 Remote Similarity NPD2403 Approved
0.69 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6897 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6886 Remote Similarity NPD4340 Discontinued
0.6885 Remote Similarity NPD5710 Approved
0.6885 Remote Similarity NPD5711 Approved
0.6878 Remote Similarity NPD7930 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