Structure

Physi-Chem Properties

Molecular Weight:  600.11
Volume:  550.278
LogP:  2.272
LogD:  0.828
LogS:  -5.003
# Rotatable Bonds:  6
TPSA:  257.04
# H-Bond Aceptor:  15
# H-Bond Donor:  9
# Rings:  5
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.116
Synthetic Accessibility Score:  4.363
Fsp3:  0.214
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.478
MDCK Permeability:  8.161058758560102e-06
Pgp-inhibitor:  0.193
Pgp-substrate:  0.086
Human Intestinal Absorption (HIA):  0.757
20% Bioavailability (F20%):  0.023
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.008
Plasma Protein Binding (PPB):  88.97150421142578%
Volume Distribution (VD):  0.642
Pgp-substrate:  15.42004680633545%

ADMET: Metabolism

CYP1A2-inhibitor:  0.616
CYP1A2-substrate:  0.045
CYP2C19-inhibitor:  0.028
CYP2C19-substrate:  0.033
CYP2C9-inhibitor:  0.54
CYP2C9-substrate:  0.165
CYP2D6-inhibitor:  0.071
CYP2D6-substrate:  0.136
CYP3A4-inhibitor:  0.101
CYP3A4-substrate:  0.007

ADMET: Excretion

Clearance (CL):  7.727
Half-life (T1/2):  0.943

ADMET: Toxicity

hERG Blockers:  0.035
Human Hepatotoxicity (H-HT):  0.226
Drug-inuced Liver Injury (DILI):  0.988
AMES Toxicity:  0.576
Rat Oral Acute Toxicity:  0.023
Maximum Recommended Daily Dose:  0.074
Skin Sensitization:  0.947
Carcinogencity:  0.028
Eye Corrosion:  0.003
Eye Irritation:  0.908
Respiratory Toxicity:  0.018

Download Data

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

  Natural Product: NPC35167

Natural Product ID:  NPC35167
Common Name*:   Quercitrin 2''-O-Gallate
IUPAC Name:   [(2S,3R,4R,5R,6S)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-methyloxan-3-yl] 3,4,5-trihydroxybenzoate
Synonyms:  
Standard InCHIKey:  KTTNFIOZYNBKEY-YIOJSCHVSA-N
Standard InCHI:  InChI=1S/C28H24O15/c1-9-20(35)23(38)26(42-27(39)11-5-16(33)21(36)17(34)6-11)28(40-9)43-25-22(37)19-15(32)7-12(29)8-18(19)41-24(25)10-2-3-13(30)14(31)4-10/h2-9,20,23,26,28-36,38H,1H3/t9-,20-,23+,26+,28-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)O)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3236511
PubChem CID:   10031482
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
NPO138 Daphniphyllum paxianum Species Daphniphyllaceae Eukaryota n.a. n.a. n.a. PMID[17887722]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota roots n.a. n.a. PMID[21911291]
NPO1346 Nerine bowdenii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[22312717]
NPO11877 Penicillium herquei Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26848504]
NPO8752 Xylaria cubensis Species Xylariaceae Eukaryota n.a. n.a. n.a. PMID[28802670]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[31675225]
NPO1831 Pseudodistoma arborescens Species Pseudodistomidae Eukaryota n.a. n.a. n.a. PMID[8450325]
NPO11877 Penicillium herquei Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[8609085]
NPO4969 Sesbania bispinosa Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9153 Sorbaria sorbifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5731 Euphorbia humifusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8127 Veronica arvensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11771 Strophanthus kombe Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8127 Veronica arvensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5731 Euphorbia humifusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11771 Strophanthus kombe Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9153 Sorbaria sorbifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6622 Artemisia klotzchiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9153 Sorbaria sorbifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11771 Strophanthus kombe Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5731 Euphorbia humifusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11657 Angelica lucida Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1697 Bitis gabonica Species Viperidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3995 Limonium sinense Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1346 Nerine bowdenii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2922 Botryosphaeria berengeriana Species Botryosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11771 Strophanthus kombe Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9153 Sorbaria sorbifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13472 Cotula cinerea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11934 Castanea vesca Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5069 Ekebergia senegalensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9252 Adina sessilifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11877 Penicillium herquei Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8127 Veronica arvensis Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO138 Daphniphyllum paxianum Species Daphniphyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5735 Solidago serotina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4969 Sesbania bispinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10149 Lespedeza bicolor Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14564 Oophaga pumilio Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6622 Artemisia klotzchiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5731 Euphorbia humifusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6845 Mimusops caffra Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1831 Pseudodistoma arborescens Species Pseudodistomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11823 Marine actinobacterium n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO8752 Xylaria cubensis Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21255 Hymenoxys insignis 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
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 26100.0 nM PMID[530774]
NPT862 Individual Protein Epoxide hydratase Homo sapiens Inhibition > 40.0 % PMID[530774]
NPT862 Individual Protein Epoxide hydratase Homo sapiens IC50 = 18640.0 nM PMID[530774]
NPT21995 SINGLE PROTEIN Synaptojanin-2 Homo sapiens IC50 = 2940.0 nM PMID[530775]
NPT21994 SINGLE PROTEIN Synaptojanin-1 Homo sapiens IC50 <= 15900.0 nM PMID[530775]
NPT21995 SINGLE PROTEIN Synaptojanin-2 Homo sapiens IC50 = 2940.0 nM PMID[530776]
NPT21994 SINGLE PROTEIN Synaptojanin-1 Homo sapiens IC50 <= 15900.0 nM PMID[530776]
NPT21995 SINGLE PROTEIN Synaptojanin-2 Homo sapiens IC50 = 2940.0 nM PMID[530777]

☑ 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 NPC35167 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 NPC61904
0.9939 High Similarity NPC144097
0.9879 High Similarity NPC267680
0.9879 High Similarity NPC217387
0.9879 High Similarity NPC293626
0.9879 High Similarity NPC217520
0.9879 High Similarity NPC113836
0.9879 High Similarity NPC258044
0.9879 High Similarity NPC37668
0.9879 High Similarity NPC139571
0.9879 High Similarity NPC196127
0.9879 High Similarity NPC253521
0.9878 High Similarity NPC214621
0.9878 High Similarity NPC34267
0.9878 High Similarity NPC223426
0.9878 High Similarity NPC81042
0.982 High Similarity NPC36138
0.9762 High Similarity NPC470416
0.9759 High Similarity NPC477895
0.9756 High Similarity NPC190003
0.9756 High Similarity NPC175107
0.9702 High Similarity NPC162394
0.9702 High Similarity NPC297503
0.9702 High Similarity NPC135831
0.9702 High Similarity NPC241781
0.9702 High Similarity NPC97119
0.9702 High Similarity NPC156785
0.9699 High Similarity NPC296018
0.9699 High Similarity NPC154741
0.9697 High Similarity NPC472993
0.9697 High Similarity NPC4390
0.9695 High Similarity NPC20505
0.9695 High Similarity NPC244776
0.9695 High Similarity NPC116864
0.9695 High Similarity NPC235260
0.9695 High Similarity NPC155763
0.9645 High Similarity NPC470717
0.9645 High Similarity NPC21359
0.9645 High Similarity NPC460984
0.9645 High Similarity NPC275977
0.9645 High Similarity NPC249560
0.9645 High Similarity NPC25946
0.9645 High Similarity NPC470720
0.9645 High Similarity NPC470713
0.9645 High Similarity NPC223860
0.9641 High Similarity NPC476773
0.9639 High Similarity NPC253685
0.9636 High Similarity NPC153755
0.9634 High Similarity NPC138927
0.9588 High Similarity NPC33083
0.9588 High Similarity NPC474093
0.9588 High Similarity NPC104910
0.9588 High Similarity NPC295625
0.9588 High Similarity NPC470719
0.9588 High Similarity NPC473554
0.9586 High Similarity NPC470718
0.9581 High Similarity NPC472385
0.9581 High Similarity NPC198324
0.9581 High Similarity NPC89127
0.9581 High Similarity NPC471669
0.9581 High Similarity NPC472992
0.9581 High Similarity NPC472991
0.9578 High Similarity NPC172033
0.9578 High Similarity NPC175230
0.9578 High Similarity NPC88560
0.9576 High Similarity NPC95866
0.9576 High Similarity NPC149011
0.9576 High Similarity NPC206123
0.9576 High Similarity NPC204937
0.9573 High Similarity NPC127546
0.9573 High Similarity NPC317489
0.9573 High Similarity NPC173637
0.9573 High Similarity NPC223424
0.9573 High Similarity NPC84362
0.9573 High Similarity NPC52550
0.9532 High Similarity NPC30011
0.9532 High Similarity NPC72554
0.9532 High Similarity NPC97817
0.9532 High Similarity NPC475179
0.9524 High Similarity NPC173837
0.9521 High Similarity NPC49344
0.9521 High Similarity NPC135277
0.9521 High Similarity NPC210094
0.9521 High Similarity NPC101191
0.9521 High Similarity NPC264735
0.9521 High Similarity NPC477848
0.9521 High Similarity NPC115760
0.9521 High Similarity NPC237435
0.9521 High Similarity NPC43211
0.9518 High Similarity NPC47140
0.9518 High Similarity NPC155877
0.9518 High Similarity NPC134532
0.9518 High Similarity NPC33054
0.9518 High Similarity NPC203259
0.9518 High Similarity NPC471748
0.9518 High Similarity NPC67134
0.9518 High Similarity NPC176740
0.9518 High Similarity NPC471725
0.9515 High Similarity NPC120099
0.9515 High Similarity NPC225434
0.9515 High Similarity NPC219904
0.9515 High Similarity NPC203050
0.9515 High Similarity NPC223747
0.9512 High Similarity NPC328940
0.9512 High Similarity NPC56077
0.9512 High Similarity NPC113968
0.9512 High Similarity NPC274618
0.9512 High Similarity NPC277174
0.9512 High Similarity NPC145038
0.9512 High Similarity NPC73855
0.9512 High Similarity NPC135599
0.9512 High Similarity NPC118284
0.9512 High Similarity NPC179950
0.9512 High Similarity NPC281131
0.9512 High Similarity NPC88789
0.9512 High Similarity NPC276222
0.9512 High Similarity NPC308404
0.9512 High Similarity NPC253662
0.9471 High Similarity NPC470445
0.9471 High Similarity NPC470446
0.9471 High Similarity NPC470447
0.9471 High Similarity NPC470449
0.9467 High Similarity NPC471030
0.9464 High Similarity NPC65563
0.9464 High Similarity NPC470949
0.9464 High Similarity NPC473862
0.9464 High Similarity NPC233994
0.9464 High Similarity NPC211532
0.9461 High Similarity NPC24043
0.9461 High Similarity NPC45522
0.9461 High Similarity NPC169977
0.9461 High Similarity NPC101026
0.9461 High Similarity NPC21666
0.9461 High Similarity NPC42773
0.9458 High Similarity NPC259896
0.9458 High Similarity NPC254855
0.9458 High Similarity NPC29958
0.9458 High Similarity NPC136042
0.9458 High Similarity NPC156869
0.9458 High Similarity NPC67326
0.9458 High Similarity NPC255157
0.9458 High Similarity NPC67105
0.9455 High Similarity NPC325555
0.9455 High Similarity NPC116745
0.9455 High Similarity NPC265530
0.9455 High Similarity NPC226304
0.9451 High Similarity NPC240431
0.9451 High Similarity NPC55786
0.9451 High Similarity NPC19240
0.9451 High Similarity NPC129264
0.9451 High Similarity NPC85751
0.9451 High Similarity NPC277205
0.9451 High Similarity NPC139060
0.9451 High Similarity NPC19388
0.9451 High Similarity NPC205824
0.9415 High Similarity NPC470455
0.9415 High Similarity NPC470451
0.9408 High Similarity NPC476619
0.9408 High Similarity NPC476622
0.9408 High Similarity NPC476621
0.9408 High Similarity NPC476623
0.9408 High Similarity NPC476618
0.9408 High Similarity NPC476620
0.9408 High Similarity NPC472387
0.9405 High Similarity NPC476472
0.9405 High Similarity NPC16194
0.9405 High Similarity NPC294629
0.9405 High Similarity NPC473327
0.9405 High Similarity NPC19108
0.9405 High Similarity NPC220173
0.9405 High Similarity NPC294815
0.9401 High Similarity NPC476405
0.9401 High Similarity NPC254540
0.9401 High Similarity NPC60735
0.9401 High Similarity NPC117260
0.9401 High Similarity NPC211594
0.9401 High Similarity NPC26230
0.9401 High Similarity NPC172807
0.9401 High Similarity NPC245452
0.9398 High Similarity NPC52382
0.9398 High Similarity NPC270578
0.9398 High Similarity NPC227508
0.9394 High Similarity NPC210073
0.9394 High Similarity NPC21100
0.9394 High Similarity NPC197285
0.9394 High Similarity NPC115674
0.939 High Similarity NPC19709
0.939 High Similarity NPC80068
0.939 High Similarity NPC168822
0.9357 High Similarity NPC35924
0.9357 High Similarity NPC199172
0.9353 High Similarity NPC241423
0.9353 High Similarity NPC110941
0.9353 High Similarity NPC470444
0.9353 High Similarity NPC473571
0.9353 High Similarity NPC473682
0.9353 High Similarity NPC470443
0.9353 High Similarity NPC126784
0.9349 High Similarity NPC472382
0.9349 High Similarity NPC14187

  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 NPC35167 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
0.9521 High Similarity NPD4338 Clinical (unspecified phase)
0.9518 High Similarity NPD6797 Phase 2
0.9461 High Similarity NPD7251 Discontinued
0.929 High Similarity NPD7808 Phase 3
0.9281 High Similarity NPD7054 Approved
0.9226 High Similarity NPD7472 Approved
0.9112 High Similarity NPD7074 Phase 3
0.9107 High Similarity NPD3818 Discontinued
0.9102 High Similarity NPD6167 Clinical (unspecified phase)
0.9102 High Similarity NPD6166 Phase 2
0.9102 High Similarity NPD6168 Clinical (unspecified phase)
0.897 High Similarity NPD4381 Clinical (unspecified phase)
0.8941 High Similarity NPD7804 Clinical (unspecified phase)
0.8909 High Similarity NPD4868 Clinical (unspecified phase)
0.8848 High Similarity NPD3817 Phase 2
0.8837 High Similarity NPD7993 Clinical (unspecified phase)
0.8683 High Similarity NPD3882 Suspended
0.8631 High Similarity NPD7075 Discontinued
0.8623 High Similarity NPD5402 Approved
0.8614 High Similarity NPD1934 Approved
0.8563 High Similarity NPD2393 Clinical (unspecified phase)
0.8563 High Similarity NPD2801 Approved
0.8503 High Similarity NPD6801 Discontinued
0.8476 Intermediate Similarity NPD1512 Approved
0.8466 Intermediate Similarity NPD6559 Discontinued
0.8453 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8424 Intermediate Similarity NPD5403 Approved
0.8383 Intermediate Similarity NPD4380 Phase 2
0.8354 Intermediate Similarity NPD6799 Approved
0.8354 Intermediate Similarity NPD1511 Approved
0.8303 Intermediate Similarity NPD5401 Approved
0.8239 Intermediate Similarity NPD3751 Discontinued
0.8225 Intermediate Similarity NPD7411 Suspended
0.8192 Intermediate Similarity NPD5844 Phase 1
0.8167 Intermediate Similarity NPD8313 Approved
0.8167 Intermediate Similarity NPD8312 Approved
0.8155 Intermediate Similarity NPD1653 Approved
0.8114 Intermediate Similarity NPD6232 Discontinued
0.8114 Intermediate Similarity NPD3787 Discontinued
0.8095 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8084 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD7473 Discontinued
0.8068 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8059 Intermediate Similarity NPD6599 Discontinued
0.8056 Intermediate Similarity NPD7685 Pre-registration
0.8043 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8034 Intermediate Similarity NPD7228 Approved
0.8023 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD7819 Suspended
0.8023 Intermediate Similarity NPD1465 Phase 2
0.8012 Intermediate Similarity NPD6190 Approved
0.801 Intermediate Similarity NPD7435 Discontinued
0.8 Intermediate Similarity NPD5494 Approved
0.7978 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7977 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7955 Intermediate Similarity NPD7199 Phase 2
0.7955 Intermediate Similarity NPD6959 Discontinued
0.7939 Intermediate Similarity NPD1549 Phase 2
0.7897 Intermediate Similarity NPD8151 Discontinued
0.7879 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD6776 Approved
0.7853 Intermediate Similarity NPD6780 Approved
0.7853 Intermediate Similarity NPD6777 Approved
0.7853 Intermediate Similarity NPD6778 Approved
0.7853 Intermediate Similarity NPD6782 Approved
0.7853 Intermediate Similarity NPD6781 Approved
0.7853 Intermediate Similarity NPD6779 Approved
0.7844 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7841 Intermediate Similarity NPD919 Approved
0.7841 Intermediate Similarity NPD6234 Discontinued
0.7818 Intermediate Similarity NPD2796 Approved
0.7789 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD3749 Approved
0.7771 Intermediate Similarity NPD7266 Discontinued
0.7766 Intermediate Similarity NPD7874 Approved
0.7766 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7759 Intermediate Similarity NPD37 Approved
0.7758 Intermediate Similarity NPD1510 Phase 2
0.7727 Intermediate Similarity NPD4966 Approved
0.7727 Intermediate Similarity NPD4967 Phase 2
0.7727 Intermediate Similarity NPD7768 Phase 2
0.7727 Intermediate Similarity NPD4965 Approved
0.7714 Intermediate Similarity NPD8455 Phase 2
0.7706 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD7871 Phase 2
0.7692 Intermediate Similarity NPD7870 Phase 2
0.7683 Intermediate Similarity NPD230 Phase 1
0.7667 Intermediate Similarity NPD3926 Phase 2
0.7654 Intermediate Similarity NPD1247 Approved
0.7641 Intermediate Similarity NPD7696 Phase 3
0.7641 Intermediate Similarity NPD7698 Approved
0.7641 Intermediate Similarity NPD7697 Approved
0.7638 Intermediate Similarity NPD7783 Phase 2
0.7638 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD3750 Approved
0.7619 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD8320 Phase 1
0.7602 Intermediate Similarity NPD8319 Approved
0.7592 Intermediate Similarity NPD6534 Approved
0.7592 Intermediate Similarity NPD6535 Approved
0.7576 Intermediate Similarity NPD7701 Phase 2
0.7576 Intermediate Similarity NPD1933 Approved
0.7574 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD7240 Approved
0.7553 Intermediate Similarity NPD8150 Discontinued
0.7529 Intermediate Similarity NPD4628 Phase 3
0.7525 Intermediate Similarity NPD7584 Approved
0.7515 Intermediate Similarity NPD1240 Approved
0.7515 Intermediate Similarity NPD1613 Approved
0.7515 Intermediate Similarity NPD943 Approved
0.7515 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1551 Phase 2
0.7476 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD7700 Phase 2
0.7474 Intermediate Similarity NPD7699 Phase 2
0.747 Intermediate Similarity NPD447 Suspended
0.7463 Intermediate Similarity NPD7801 Approved
0.7425 Intermediate Similarity NPD1607 Approved
0.7411 Intermediate Similarity NPD6823 Phase 2
0.7396 Intermediate Similarity NPD2935 Discontinued
0.7394 Intermediate Similarity NPD6798 Discontinued
0.7394 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7458 Discontinued
0.7386 Intermediate Similarity NPD3226 Approved
0.7371 Intermediate Similarity NPD920 Approved
0.7368 Intermediate Similarity NPD8434 Phase 2
0.7356 Intermediate Similarity NPD2533 Approved
0.7356 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD2534 Approved
0.7356 Intermediate Similarity NPD2532 Approved
0.7349 Intermediate Similarity NPD6233 Phase 2
0.7337 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD3748 Approved
0.7326 Intermediate Similarity NPD5953 Discontinued
0.7313 Intermediate Similarity NPD7585 Approved
0.7286 Intermediate Similarity NPD7680 Approved
0.7273 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7264 Intermediate Similarity NPD7583 Approved
0.7259 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD3027 Phase 3
0.7219 Intermediate Similarity NPD7286 Phase 2
0.7212 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD2313 Discontinued
0.7179 Intermediate Similarity NPD6212 Phase 3
0.7179 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD6213 Phase 3
0.7169 Intermediate Similarity NPD6832 Phase 2
0.7168 Intermediate Similarity NPD1243 Approved
0.7151 Intermediate Similarity NPD2346 Discontinued
0.7143 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD2799 Discontinued
0.7135 Intermediate Similarity NPD7033 Discontinued
0.7102 Intermediate Similarity NPD7390 Discontinued
0.7091 Intermediate Similarity NPD1203 Approved
0.7088 Intermediate Similarity NPD5353 Approved
0.7072 Intermediate Similarity NPD6844 Discontinued
0.7069 Intermediate Similarity NPD2800 Approved
0.7069 Intermediate Similarity NPD1652 Phase 2
0.7068 Intermediate Similarity NPD7549 Discontinued
0.7066 Intermediate Similarity NPD4908 Phase 1
0.7059 Intermediate Similarity NPD6355 Discontinued
0.7059 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD2344 Approved
0.7044 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD7039 Approved
0.7016 Intermediate Similarity NPD7038 Approved
0.7012 Intermediate Similarity NPD9269 Phase 2
0.7006 Intermediate Similarity NPD9494 Approved
0.7005 Intermediate Similarity NPD5242 Approved
0.6989 Remote Similarity NPD8127 Discontinued
0.6982 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6979 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6977 Remote Similarity NPD7097 Phase 1
0.6971 Remote Similarity NPD6674 Discontinued
0.697 Remote Similarity NPD4363 Phase 3
0.697 Remote Similarity NPD4360 Phase 2
0.6966 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5124 Phase 1
0.6959 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6952 Remote Similarity NPD7229 Phase 3
0.6952 Remote Similarity NPD5710 Approved
0.6952 Remote Similarity NPD5711 Approved
0.6951 Remote Similarity NPD1091 Approved
0.6946 Remote Similarity NPD2798 Approved
0.6939 Remote Similarity NPD4287 Approved
0.6936 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6386 Approved
0.6923 Remote Similarity NPD6385 Approved
0.6923 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6909 Remote Similarity NPD9717 Approved
0.6907 Remote Similarity NPD7090 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data