Structure

Physi-Chem Properties

Molecular Weight:  616.11
Volume:  559.068
LogP:  1.429
LogD:  0.347
LogS:  -4.592
# Rotatable Bonds:  7
TPSA:  277.27
# H-Bond Aceptor:  16
# H-Bond Donor:  10
# Rings:  5
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.104
Synthetic Accessibility Score:  4.372
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:  -6.552
MDCK Permeability:  6.1009309320070315e-06
Pgp-inhibitor:  0.096
Pgp-substrate:  0.031
Human Intestinal Absorption (HIA):  0.822
20% Bioavailability (F20%):  0.39
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.008
Plasma Protein Binding (PPB):  87.85358428955078%
Volume Distribution (VD):  0.672
Pgp-substrate:  16.764110565185547%

ADMET: Metabolism

CYP1A2-inhibitor:  0.567
CYP1A2-substrate:  0.022
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.031
CYP2C9-inhibitor:  0.43
CYP2C9-substrate:  0.08
CYP2D6-inhibitor:  0.029
CYP2D6-substrate:  0.132
CYP3A4-inhibitor:  0.088
CYP3A4-substrate:  0.005

ADMET: Excretion

Clearance (CL):  6.982
Half-life (T1/2):  0.95

ADMET: Toxicity

hERG Blockers:  0.199
Human Hepatotoxicity (H-HT):  0.19
Drug-inuced Liver Injury (DILI):  0.988
AMES Toxicity:  0.528
Rat Oral Acute Toxicity:  0.011
Maximum Recommended Daily Dose:  0.011
Skin Sensitization:  0.945
Carcinogencity:  0.026
Eye Corrosion:  0.003
Eye Irritation:  0.903
Respiratory Toxicity:  0.009

Download Data

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

  Natural Product: NPC253521

Natural Product ID:  NPC253521
Common Name*:   Quercetin -3-O-(2''-O-Galloyl)-Beta-D-Galactopyranoside
IUPAC Name:   [(2S,3R,4S,5R,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 3,4,5-trihydroxybenzoate
Synonyms:  
Standard InCHIKey:  PXGWEUQZDRUMRE-UNZYZCBSSA-N
Standard InCHI:  InChI=1S/C28H24O16/c29-8-18-21(37)23(39)26(43-27(40)10-4-15(34)20(36)16(35)5-10)28(42-18)44-25-22(38)19-14(33)6-11(30)7-17(19)41-24(25)9-1-2-12(31)13(32)3-9/h1-7,18,21,23,26,28-37,39H,8H2/t18-,21+,23+,26-,28+/m1/s1
SMILES:  c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)OC(=O)c1cc(c(c(c1)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL505880
PubChem CID:   6453359
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
NPO15704 Euphorbia lunulata Species Euphorbiaceae Eukaryota n.a. whole plant n.a. PMID[15744103]
NPO12148.2 Acer pictum subsp. okamotoanum Subspecies Sapindaceae Eukaryota n.a. n.a. n.a. PMID[9461665]
NPO15704 Euphorbia lunulata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13524 Pyrola japonica Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19095 Strophanthus preussii Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19095 Strophanthus preussii Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15704 Euphorbia lunulata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13524 Pyrola japonica Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15704 Euphorbia lunulata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13524 Pyrola japonica Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13524 Pyrola japonica Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2977 Colletotrichum lagenaria Species Glomerellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13524 Pyrola japonica Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2359 Cynoglossum germanicum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12148.2 Acer pictum subsp. okamotoanum Subspecies Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13823 Hypericum mysorense Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18537 Leontopodium nanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17247 Actinoplanes friuliensis Species Micromonosporaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5214 Machaerium nictitans Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19521 Inella verrucosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3367 Cassytha racemosa Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18680 Larix decidua Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19095 Strophanthus preussii Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18775 Cratena peregrina Species Facelinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15704 Euphorbia lunulata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21211 Penicillium stipitatum Species Aspergillaceae 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
NPT12 Individual Protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 IC50 = 27.9 ug.mL-1 PMID[533995]

☑ 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 NPC253521 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 NPC37668
1.0 High Similarity NPC113836
0.9939 High Similarity NPC61904
0.9939 High Similarity NPC144097
0.9879 High Similarity NPC267680
0.9879 High Similarity NPC293626
0.9879 High Similarity NPC35167
0.9879 High Similarity NPC258044
0.9879 High Similarity NPC196127
0.9879 High Similarity NPC217387
0.9878 High Similarity NPC223426
0.9878 High Similarity NPC214621
0.9878 High Similarity NPC34267
0.9878 High Similarity NPC81042
0.982 High Similarity NPC297503
0.982 High Similarity NPC97119
0.982 High Similarity NPC135831
0.9759 High Similarity NPC217520
0.9759 High Similarity NPC139571
0.9758 High Similarity NPC253685
0.9702 High Similarity NPC162394
0.9702 High Similarity NPC470718
0.9702 High Similarity NPC241781
0.9702 High Similarity NPC36138
0.9702 High Similarity NPC156785
0.9699 High Similarity NPC296018
0.9699 High Similarity NPC154741
0.9695 High Similarity NPC20505
0.9695 High Similarity NPC235260
0.9695 High Similarity NPC155763
0.9645 High Similarity NPC21359
0.9645 High Similarity NPC275977
0.9645 High Similarity NPC460984
0.9645 High Similarity NPC249560
0.9645 High Similarity NPC470416
0.9645 High Similarity NPC25946
0.9645 High Similarity NPC470720
0.9645 High Similarity NPC470717
0.9645 High Similarity NPC470713
0.9645 High Similarity NPC223860
0.9641 High Similarity NPC476773
0.9641 High Similarity NPC477895
0.9636 High Similarity NPC175107
0.9636 High Similarity NPC190003
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
0.9581 High Similarity NPC89127
0.9581 High Similarity NPC471669
0.9581 High Similarity NPC472992
0.9581 High Similarity NPC472991
0.9578 High Similarity NPC4390
0.9578 High Similarity NPC472993
0.9576 High Similarity NPC29958
0.9576 High Similarity NPC244776
0.9576 High Similarity NPC259896
0.9576 High Similarity NPC116864
0.9576 High Similarity NPC136042
0.9576 High Similarity NPC67326
0.9576 High Similarity NPC149011
0.9576 High Similarity NPC255157
0.9576 High Similarity NPC204937
0.9576 High Similarity NPC254855
0.9576 High Similarity NPC156869
0.9532 High Similarity NPC30011
0.9532 High Similarity NPC72554
0.9532 High Similarity NPC475179
0.9532 High Similarity NPC97817
0.9524 High Similarity NPC173837
0.9521 High Similarity NPC49344
0.9521 High Similarity NPC210094
0.9521 High Similarity NPC101191
0.9521 High Similarity NPC237435
0.9521 High Similarity NPC115760
0.9521 High Similarity NPC43211
0.9521 High Similarity NPC135277
0.9518 High Similarity NPC47140
0.9518 High Similarity NPC67134
0.9518 High Similarity NPC155877
0.9518 High Similarity NPC60735
0.9518 High Similarity NPC134532
0.9518 High Similarity NPC33054
0.9518 High Similarity NPC203259
0.9518 High Similarity NPC471748
0.9518 High Similarity NPC176740
0.9518 High Similarity NPC26230
0.9518 High Similarity NPC153755
0.9518 High Similarity NPC471725
0.9512 High Similarity NPC274618
0.9512 High Similarity NPC145038
0.9512 High Similarity NPC281131
0.9512 High Similarity NPC118284
0.9512 High Similarity NPC179950
0.9512 High Similarity NPC88789
0.9512 High Similarity NPC253662
0.9512 High Similarity NPC56077
0.9512 High Similarity NPC276222
0.9512 High Similarity NPC308404
0.9471 High Similarity NPC470445
0.9471 High Similarity NPC470446
0.9471 High Similarity NPC470449
0.9471 High Similarity NPC470447
0.9464 High Similarity NPC65563
0.9464 High Similarity NPC473862
0.9464 High Similarity NPC472385
0.9464 High Similarity NPC198324
0.9464 High Similarity NPC470949
0.9464 High Similarity NPC8573
0.9461 High Similarity NPC88560
0.9461 High Similarity NPC172033
0.9461 High Similarity NPC175230
0.9458 High Similarity NPC95866
0.9458 High Similarity NPC285197
0.9458 High Similarity NPC206123
0.9458 High Similarity NPC67105
0.9455 High Similarity NPC127546
0.9455 High Similarity NPC275454
0.9455 High Similarity NPC173637
0.9455 High Similarity NPC84362
0.9455 High Similarity NPC317489
0.9455 High Similarity NPC52550
0.9455 High Similarity NPC223424
0.9451 High Similarity NPC55786
0.9451 High Similarity NPC19240
0.9451 High Similarity NPC129264
0.9451 High Similarity NPC240431
0.9451 High Similarity NPC85751
0.9451 High Similarity NPC277205
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 NPC476618
0.9408 High Similarity NPC476620
0.9408 High Similarity NPC476621
0.9408 High Similarity NPC476623
0.9405 High Similarity NPC476472
0.9405 High Similarity NPC16194
0.9405 High Similarity NPC477848
0.9405 High Similarity NPC294815
0.9405 High Similarity NPC473327
0.9405 High Similarity NPC264735
0.9405 High Similarity NPC19108
0.9405 High Similarity NPC220173
0.9398 High Similarity NPC225434
0.9398 High Similarity NPC227508
0.9398 High Similarity NPC120099
0.9398 High Similarity NPC219904
0.9398 High Similarity NPC223747
0.9398 High Similarity NPC203050
0.9394 High Similarity NPC197285
0.9394 High Similarity NPC21100
0.9394 High Similarity NPC8856
0.9394 High Similarity NPC113968
0.9394 High Similarity NPC135599
0.9394 High Similarity NPC277174
0.9394 High Similarity NPC73855
0.9394 High Similarity NPC328940
0.939 High Similarity NPC80068
0.939 High Similarity NPC168822
0.9357 High Similarity NPC199172
0.9357 High Similarity NPC35924
0.9357 High Similarity NPC107987
0.9353 High Similarity NPC241423
0.9353 High Similarity NPC470444
0.9353 High Similarity NPC110941
0.9353 High Similarity NPC473571
0.9353 High Similarity NPC473682
0.9353 High Similarity NPC470443
0.9353 High Similarity NPC126784
0.9353 High Similarity NPC471030
0.9349 High Similarity NPC219043
0.9349 High Similarity NPC268533
0.9349 High Similarity NPC202908
0.9349 High Similarity NPC122467
0.9349 High Similarity NPC169733
0.9349 High Similarity NPC233994
0.9349 High Similarity NPC292019
0.9349 High Similarity NPC14187
0.9349 High Similarity NPC211532
0.9345 High Similarity NPC21666
0.9345 High Similarity NPC169977
0.9345 High Similarity NPC42773
0.9345 High Similarity NPC45522
0.9345 High Similarity NPC24043
0.9345 High Similarity NPC101026
0.9341 High Similarity NPC245014
0.9341 High Similarity NPC282987
0.9341 High Similarity NPC164704
0.9341 High Similarity NPC84265
0.9341 High Similarity NPC470712
0.9341 High Similarity NPC72249
0.9337 High Similarity NPC265530
0.9337 High Similarity NPC226304

  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 NPC253521 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
0.9226 High Similarity NPD7472 Approved
0.9167 High Similarity NPD7054 Approved
0.9107 High Similarity NPD3818 Discontinued
0.9 High Similarity NPD7074 Phase 3
0.8988 High Similarity NPD6166 Phase 2
0.8988 High Similarity NPD6168 Clinical (unspecified phase)
0.8988 High Similarity NPD6167 Clinical (unspecified phase)
0.897 High Similarity NPD4381 Clinical (unspecified phase)
0.8947 High Similarity NPD7993 Clinical (unspecified phase)
0.8909 High Similarity NPD4868 Clinical (unspecified phase)
0.883 High Similarity NPD7804 Clinical (unspecified phase)
0.8735 High Similarity NPD3817 Phase 2
0.8623 High Similarity NPD5402 Approved
0.8571 High Similarity NPD3882 Suspended
0.8521 High Similarity NPD7075 Discontinued
0.8503 High Similarity NPD1934 Approved
0.8476 Intermediate Similarity NPD1512 Approved
0.8452 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD2801 Approved
0.8424 Intermediate Similarity NPD5403 Approved
0.8393 Intermediate Similarity NPD6801 Discontinued
0.8383 Intermediate Similarity NPD4380 Phase 2
0.8362 Intermediate Similarity NPD6559 Discontinued
0.8354 Intermediate Similarity NPD1511 Approved
0.8352 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8343 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8303 Intermediate Similarity NPD5401 Approved
0.8268 Intermediate Similarity NPD8313 Approved
0.8268 Intermediate Similarity NPD8312 Approved
0.8242 Intermediate Similarity NPD6799 Approved
0.8239 Intermediate Similarity NPD3751 Discontinued
0.8155 Intermediate Similarity NPD1653 Approved
0.8118 Intermediate Similarity NPD7411 Suspended
0.8114 Intermediate Similarity NPD3787 Discontinued
0.809 Intermediate Similarity NPD5844 Phase 1
0.8023 Intermediate Similarity NPD1465 Phase 2
0.8012 Intermediate Similarity NPD6190 Approved
0.8011 Intermediate Similarity NPD6232 Discontinued
0.7988 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7978 Intermediate Similarity NPD7473 Discontinued
0.7976 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7966 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7956 Intermediate Similarity NPD7685 Pre-registration
0.7953 Intermediate Similarity NPD6599 Discontinued
0.7946 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD1549 Phase 2
0.7933 Intermediate Similarity NPD7228 Approved
0.7921 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD7819 Suspended
0.7917 Intermediate Similarity NPD7435 Discontinued
0.7898 Intermediate Similarity NPD5494 Approved
0.7897 Intermediate Similarity NPD8151 Discontinued
0.788 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7874 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD6959 Discontinued
0.7853 Intermediate Similarity NPD7199 Phase 2
0.7816 Intermediate Similarity NPD8455 Phase 2
0.7784 Intermediate Similarity NPD3749 Approved
0.776 Intermediate Similarity NPD6780 Approved
0.776 Intermediate Similarity NPD6779 Approved
0.776 Intermediate Similarity NPD6776 Approved
0.776 Intermediate Similarity NPD6781 Approved
0.776 Intermediate Similarity NPD6778 Approved
0.776 Intermediate Similarity NPD6782 Approved
0.776 Intermediate Similarity NPD6777 Approved
0.7758 Intermediate Similarity NPD1510 Phase 2
0.774 Intermediate Similarity NPD6234 Discontinued
0.774 Intermediate Similarity NPD919 Approved
0.7738 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD2796 Approved
0.7696 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD7874 Approved
0.7677 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD7266 Discontinued
0.7657 Intermediate Similarity NPD37 Approved
0.7633 Intermediate Similarity NPD3750 Approved
0.7627 Intermediate Similarity NPD4966 Approved
0.7627 Intermediate Similarity NPD4967 Phase 2
0.7627 Intermediate Similarity NPD7768 Phase 2
0.7627 Intermediate Similarity NPD4965 Approved
0.7602 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD7870 Phase 2
0.7602 Intermediate Similarity NPD7871 Phase 2
0.7576 Intermediate Similarity NPD230 Phase 1
0.7569 Intermediate Similarity NPD3926 Phase 2
0.7568 Intermediate Similarity NPD7240 Approved
0.7556 Intermediate Similarity NPD1247 Approved
0.7551 Intermediate Similarity NPD7698 Approved
0.7551 Intermediate Similarity NPD7696 Phase 3
0.7551 Intermediate Similarity NPD7697 Approved
0.755 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD7783 Phase 2
0.7515 Intermediate Similarity NPD1613 Approved
0.7515 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD943 Approved
0.7515 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD8320 Phase 1
0.7513 Intermediate Similarity NPD8319 Approved
0.75 Intermediate Similarity NPD1551 Phase 2
0.75 Intermediate Similarity NPD6535 Approved
0.75 Intermediate Similarity NPD6534 Approved
0.7487 Intermediate Similarity NPD7701 Phase 2
0.7471 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD1933 Approved
0.746 Intermediate Similarity NPD8150 Discontinued
0.7437 Intermediate Similarity NPD7584 Approved
0.7427 Intermediate Similarity NPD4628 Phase 3
0.741 Intermediate Similarity NPD1240 Approved
0.7391 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD7699 Phase 2
0.7385 Intermediate Similarity NPD7700 Phase 2
0.7376 Intermediate Similarity NPD7801 Approved
0.7368 Intermediate Similarity NPD8434 Phase 2
0.7365 Intermediate Similarity NPD447 Suspended
0.7356 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD3748 Approved
0.7323 Intermediate Similarity NPD6823 Phase 2
0.7321 Intermediate Similarity NPD1607 Approved
0.7294 Intermediate Similarity NPD2935 Discontinued
0.7289 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD6798 Discontinued
0.7288 Intermediate Similarity NPD3226 Approved
0.7288 Intermediate Similarity NPD7458 Discontinued
0.7273 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD920 Approved
0.7257 Intermediate Similarity NPD2533 Approved
0.7257 Intermediate Similarity NPD2532 Approved
0.7257 Intermediate Similarity NPD2534 Approved
0.7257 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD6233 Phase 2
0.7243 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD5953 Discontinued
0.7228 Intermediate Similarity NPD7585 Approved
0.7212 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7680 Approved
0.7191 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD2313 Discontinued
0.7178 Intermediate Similarity NPD7583 Approved
0.7172 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD7286 Phase 2
0.7126 Intermediate Similarity NPD3027 Phase 3
0.7092 Intermediate Similarity NPD6212 Phase 3
0.7092 Intermediate Similarity NPD6213 Phase 3
0.7092 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD1203 Approved
0.7069 Intermediate Similarity NPD1243 Approved
0.7066 Intermediate Similarity NPD6832 Phase 2
0.7052 Intermediate Similarity NPD2346 Discontinued
0.705 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD2799 Discontinued
0.7035 Intermediate Similarity NPD7033 Discontinued
0.7012 Intermediate Similarity NPD9269 Phase 2
0.7006 Intermediate Similarity NPD7390 Discontinued
0.6995 Remote Similarity NPD5353 Approved
0.6979 Remote Similarity NPD7549 Discontinued
0.6978 Remote Similarity NPD6844 Discontinued
0.6971 Remote Similarity NPD2800 Approved
0.6971 Remote Similarity NPD1652 Phase 2
0.6964 Remote Similarity NPD4908 Phase 1
0.6961 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6959 Remote Similarity NPD6355 Discontinued
0.6959 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6954 Remote Similarity NPD2344 Approved
0.6951 Remote Similarity NPD1091 Approved
0.6939 Remote Similarity NPD4287 Approved
0.6932 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6927 Remote Similarity NPD7039 Approved
0.6927 Remote Similarity NPD7038 Approved
0.6915 Remote Similarity NPD5242 Approved
0.6905 Remote Similarity NPD9494 Approved
0.6898 Remote Similarity NPD8127 Discontinued
0.6891 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6884 Remote Similarity NPD4360 Phase 2
0.6884 Remote Similarity NPD4363 Phase 3
0.6882 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6879 Remote Similarity NPD7097 Phase 1
0.6875 Remote Similarity NPD6674 Discontinued
0.6872 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6862 Remote Similarity NPD5711 Approved
0.6862 Remote Similarity NPD7229 Phase 3
0.6862 Remote Similarity NPD5710 Approved
0.686 Remote Similarity NPD5124 Phase 1
0.686 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6848 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6845 Remote Similarity NPD2798 Approved
0.6839 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6831 Remote Similarity NPD6385 Approved
0.6831 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6831 Remote Similarity NPD6386 Approved
0.6826 Remote Similarity NPD3225 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