Structure

Physi-Chem Properties

Molecular Weight:  752.12
Volume:  687.408
LogP:  2.417
LogD:  0.889
LogS:  -4.603
# Rotatable Bonds:  10
TPSA:  323.8
# H-Bond Aceptor:  19
# H-Bond Donor:  11
# Rings:  6
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.079
Synthetic Accessibility Score:  4.65
Fsp3:  0.171
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:  -6.7
MDCK Permeability:  6.543832114402903e-06
Pgp-inhibitor:  0.381
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.884
20% Bioavailability (F20%):  0.555
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.005
Plasma Protein Binding (PPB):  88.06574249267578%
Volume Distribution (VD):  0.575
Pgp-substrate:  19.001514434814453%

ADMET: Metabolism

CYP1A2-inhibitor:  0.72
CYP1A2-substrate:  0.012
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.023
CYP2C9-inhibitor:  0.529
CYP2C9-substrate:  0.071
CYP2D6-inhibitor:  0.042
CYP2D6-substrate:  0.104
CYP3A4-inhibitor:  0.075
CYP3A4-substrate:  0.004

ADMET: Excretion

Clearance (CL):  7.065
Half-life (T1/2):  0.967

ADMET: Toxicity

hERG Blockers:  0.155
Human Hepatotoxicity (H-HT):  0.242
Drug-inuced Liver Injury (DILI):  0.992
AMES Toxicity:  0.229
Rat Oral Acute Toxicity:  0.006
Maximum Recommended Daily Dose:  0.007
Skin Sensitization:  0.95
Carcinogencity:  0.02
Eye Corrosion:  0.003
Eye Irritation:  0.907
Respiratory Toxicity:  0.005

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

  Natural Product: NPC297503

Natural Product ID:  NPC297503
Common Name*:   Astragalin 2'',3''-O-Digallate
IUPAC Name:   [(2S,3R,4S,5R,6R)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyl)oxyoxan-4-yl] 3,4,5-trihydroxybenzoate
Synonyms:  
Standard InCHIKey:  XIJNRDKMQMEBGV-FGQFUJKUSA-N
Standard InCHI:  InChI=1S/C35H28O19/c36-11-23-27(46)30(52-33(48)13-5-18(40)25(44)19(41)6-13)32(53-34(49)14-7-20(42)26(45)21(43)8-14)35(51-23)54-31-28(47)24-17(39)9-16(38)10-22(24)50-29(31)12-1-3-15(37)4-2-12/h1-10,23,27,30,32,35-46H,11H2/t23-,27-,30+,32-,35+/m1/s1
SMILES:  c1cc(ccc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)OC(=O)c1cc(c(c(c1)O)O)O)OC(=O)c1cc(c(c(c1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3236510
PubChem CID:   90654760
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
NPO5731 Euphorbia humifusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5731 Euphorbia humifusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5731 Euphorbia humifusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5731 Euphorbia humifusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2922 Botryosphaeria berengeriana Species Botryosphaeriaceae 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
NPT862 Individual Protein Epoxide hydratase Homo sapiens Inhibition > 40.0 % PMID[507962]
NPT862 Individual Protein Epoxide hydratase Homo sapiens IC50 = 23810.0 nM PMID[507962]

☑ 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 NPC297503 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 NPC135831
1.0 High Similarity NPC97119
0.982 High Similarity NPC253521
0.982 High Similarity NPC113836
0.982 High Similarity NPC37668
0.9765 High Similarity NPC474093
0.9765 High Similarity NPC104910
0.976 High Similarity NPC61904
0.976 High Similarity NPC144097
0.9708 High Similarity NPC475179
0.9708 High Similarity NPC72554
0.9708 High Similarity NPC97817
0.9708 High Similarity NPC30011
0.9702 High Similarity NPC293626
0.9702 High Similarity NPC196127
0.9702 High Similarity NPC35167
0.9702 High Similarity NPC217387
0.9702 High Similarity NPC258044
0.9702 High Similarity NPC267680
0.9701 High Similarity NPC223426
0.9701 High Similarity NPC81042
0.9701 High Similarity NPC214621
0.9701 High Similarity NPC34267
0.9647 High Similarity NPC156785
0.9647 High Similarity NPC162394
0.9647 High Similarity NPC241781
0.9647 High Similarity NPC470718
0.9591 High Similarity NPC275977
0.9591 High Similarity NPC21359
0.9591 High Similarity NPC223860
0.9591 High Similarity NPC470416
0.9591 High Similarity NPC470713
0.9591 High Similarity NPC470717
0.9591 High Similarity NPC460984
0.9591 High Similarity NPC249560
0.9591 High Similarity NPC25946
0.9591 High Similarity NPC470720
0.9586 High Similarity NPC477895
0.9586 High Similarity NPC139571
0.9586 High Similarity NPC217520
0.9583 High Similarity NPC253685
0.9535 High Similarity NPC295625
0.9535 High Similarity NPC33083
0.9535 High Similarity NPC473554
0.9535 High Similarity NPC470719
0.9532 High Similarity NPC36138
0.9529 High Similarity NPC471030
0.9527 High Similarity NPC296018
0.9527 High Similarity NPC154741
0.9521 High Similarity NPC235260
0.9521 High Similarity NPC155763
0.9521 High Similarity NPC20505
0.9477 High Similarity NPC231254
0.9471 High Similarity NPC476773
0.9464 High Similarity NPC190003
0.9464 High Similarity NPC175107
0.9461 High Similarity NPC138927
0.9412 High Similarity NPC472991
0.9412 High Similarity NPC473862
0.9412 High Similarity NPC471669
0.9412 High Similarity NPC472992
0.9412 High Similarity NPC89127
0.9408 High Similarity NPC175230
0.9408 High Similarity NPC88560
0.9408 High Similarity NPC172033
0.9408 High Similarity NPC4390
0.9408 High Similarity NPC472993
0.9405 High Similarity NPC67326
0.9405 High Similarity NPC255157
0.9405 High Similarity NPC280642
0.9405 High Similarity NPC96605
0.9405 High Similarity NPC156869
0.9405 High Similarity NPC244776
0.9405 High Similarity NPC204937
0.9405 High Similarity NPC116864
0.9405 High Similarity NPC254855
0.9405 High Similarity NPC136042
0.9405 High Similarity NPC29958
0.9405 High Similarity NPC218161
0.9405 High Similarity NPC149011
0.9405 High Similarity NPC259896
0.9368 High Similarity NPC65489
0.9368 High Similarity NPC64755
0.9364 High Similarity NPC470451
0.9364 High Similarity NPC470455
0.9357 High Similarity NPC173837
0.9353 High Similarity NPC115760
0.9353 High Similarity NPC43211
0.9353 High Similarity NPC101191
0.9353 High Similarity NPC135277
0.9353 High Similarity NPC49344
0.9353 High Similarity NPC237435
0.9353 High Similarity NPC210094
0.9349 High Similarity NPC471725
0.9349 High Similarity NPC203259
0.9349 High Similarity NPC26230
0.9349 High Similarity NPC471748
0.9349 High Similarity NPC11847
0.9349 High Similarity NPC47140
0.9349 High Similarity NPC67134
0.9349 High Similarity NPC221288
0.9349 High Similarity NPC176740
0.9349 High Similarity NPC134532
0.9349 High Similarity NPC101399
0.9349 High Similarity NPC217822
0.9349 High Similarity NPC155877
0.9349 High Similarity NPC33054
0.9349 High Similarity NPC60735
0.9349 High Similarity NPC153755
0.9341 High Similarity NPC281131
0.9341 High Similarity NPC118284
0.9341 High Similarity NPC274618
0.9341 High Similarity NPC56077
0.9341 High Similarity NPC253662
0.9341 High Similarity NPC276222
0.9341 High Similarity NPC308404
0.9341 High Similarity NPC88789
0.9341 High Similarity NPC145038
0.9341 High Similarity NPC179950
0.9306 High Similarity NPC35924
0.9306 High Similarity NPC132111
0.9306 High Similarity NPC470449
0.9306 High Similarity NPC470447
0.9306 High Similarity NPC199172
0.9306 High Similarity NPC470446
0.9306 High Similarity NPC470445
0.9298 High Similarity NPC202908
0.9298 High Similarity NPC8573
0.9298 High Similarity NPC65563
0.9298 High Similarity NPC292019
0.9298 High Similarity NPC231787
0.9298 High Similarity NPC472385
0.9298 High Similarity NPC198324
0.9298 High Similarity NPC470949
0.9298 High Similarity NPC219043
0.9298 High Similarity NPC122467
0.9298 High Similarity NPC14187
0.9294 High Similarity NPC476374
0.929 High Similarity NPC469344
0.929 High Similarity NPC285197
0.929 High Similarity NPC188815
0.929 High Similarity NPC92815
0.929 High Similarity NPC67105
0.929 High Similarity NPC206123
0.929 High Similarity NPC470712
0.929 High Similarity NPC95866
0.929 High Similarity NPC164704
0.9286 High Similarity NPC52550
0.9286 High Similarity NPC84362
0.9286 High Similarity NPC275454
0.9286 High Similarity NPC173637
0.9286 High Similarity NPC223424
0.9286 High Similarity NPC317489
0.9286 High Similarity NPC127546
0.9281 High Similarity NPC19388
0.9281 High Similarity NPC205824
0.9281 High Similarity NPC240431
0.9281 High Similarity NPC277205
0.9281 High Similarity NPC129264
0.9281 High Similarity NPC19240
0.9281 High Similarity NPC55786
0.9281 High Similarity NPC85751
0.9261 High Similarity NPC201814
0.9249 High Similarity NPC469371
0.9244 High Similarity NPC476618
0.9244 High Similarity NPC476619
0.9244 High Similarity NPC476623
0.9244 High Similarity NPC89052
0.9244 High Similarity NPC476622
0.9244 High Similarity NPC476620
0.9244 High Similarity NPC476621
0.9244 High Similarity NPC251417
0.924 High Similarity NPC477848
0.924 High Similarity NPC264735
0.924 High Similarity NPC220173
0.924 High Similarity NPC473327
0.924 High Similarity NPC19108
0.924 High Similarity NPC476472
0.924 High Similarity NPC16194
0.924 High Similarity NPC294815
0.9235 High Similarity NPC470716
0.9235 High Similarity NPC470714
0.9235 High Similarity NPC476370
0.9235 High Similarity NPC470715
0.9235 High Similarity NPC474522
0.9231 High Similarity NPC227508
0.9231 High Similarity NPC203050
0.9231 High Similarity NPC95421
0.9231 High Similarity NPC219904
0.9231 High Similarity NPC225434
0.9231 High Similarity NPC120099
0.9231 High Similarity NPC223747
0.9231 High Similarity NPC198125
0.9226 High Similarity NPC135599
0.9226 High Similarity NPC473278
0.9226 High Similarity NPC328940
0.9226 High Similarity NPC89809
0.9226 High Similarity NPC21100
0.9226 High Similarity NPC8856
0.9226 High Similarity NPC260504

  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 NPC297503 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
0.9353 High Similarity NPD4338 Clinical (unspecified phase)
0.9349 High Similarity NPD6797 Phase 2
0.9294 High Similarity NPD7251 Discontinued
0.924 High Similarity NPD7808 Phase 3
0.9123 High Similarity NPD7993 Clinical (unspecified phase)
0.9064 High Similarity NPD7472 Approved
0.9006 High Similarity NPD7054 Approved
0.8947 High Similarity NPD3818 Discontinued
0.8844 High Similarity NPD7074 Phase 3
0.883 High Similarity NPD6168 Clinical (unspecified phase)
0.883 High Similarity NPD6167 Clinical (unspecified phase)
0.883 High Similarity NPD6166 Phase 2
0.881 High Similarity NPD4381 Clinical (unspecified phase)
0.8786 High Similarity NPD7804 Clinical (unspecified phase)
0.875 High Similarity NPD4868 Clinical (unspecified phase)
0.858 High Similarity NPD3817 Phase 2
0.8471 Intermediate Similarity NPD5402 Approved
0.8436 Intermediate Similarity NPD8312 Approved
0.8436 Intermediate Similarity NPD8313 Approved
0.8421 Intermediate Similarity NPD3882 Suspended
0.8415 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8372 Intermediate Similarity NPD7075 Discontinued
0.8353 Intermediate Similarity NPD1934 Approved
0.8323 Intermediate Similarity NPD1512 Approved
0.8304 Intermediate Similarity NPD2801 Approved
0.8304 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8274 Intermediate Similarity NPD5403 Approved
0.8246 Intermediate Similarity NPD6801 Discontinued
0.8235 Intermediate Similarity NPD4380 Phase 2
0.8222 Intermediate Similarity NPD6559 Discontinued
0.8204 Intermediate Similarity NPD1511 Approved
0.8198 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD5401 Approved
0.8108 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8101 Intermediate Similarity NPD3751 Discontinued
0.8095 Intermediate Similarity NPD6799 Approved
0.809 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD3787 Discontinued
0.8012 Intermediate Similarity NPD1653 Approved
0.7989 Intermediate Similarity NPD8455 Phase 2
0.7977 Intermediate Similarity NPD7411 Suspended
0.7959 Intermediate Similarity NPD8151 Discontinued
0.7956 Intermediate Similarity NPD5844 Phase 1
0.7923 Intermediate Similarity NPD7685 Pre-registration
0.7921 Intermediate Similarity NPD6959 Discontinued
0.7887 Intermediate Similarity NPD7435 Discontinued
0.7886 Intermediate Similarity NPD7819 Suspended
0.7886 Intermediate Similarity NPD1465 Phase 2
0.7877 Intermediate Similarity NPD6232 Discontinued
0.787 Intermediate Similarity NPD6190 Approved
0.7849 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7845 Intermediate Similarity NPD7473 Discontinued
0.7841 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7833 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD6599 Discontinued
0.7802 Intermediate Similarity NPD7228 Approved
0.7798 Intermediate Similarity NPD1549 Phase 2
0.7797 Intermediate Similarity NPD7768 Phase 2
0.7765 Intermediate Similarity NPD5494 Approved
0.7753 Intermediate Similarity NPD3749 Approved
0.7739 Intermediate Similarity NPD7874 Approved
0.7739 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7732 Intermediate Similarity NPD6777 Approved
0.7732 Intermediate Similarity NPD6776 Approved
0.7732 Intermediate Similarity NPD6778 Approved
0.7732 Intermediate Similarity NPD6779 Approved
0.7732 Intermediate Similarity NPD6780 Approved
0.7732 Intermediate Similarity NPD6782 Approved
0.7732 Intermediate Similarity NPD6781 Approved
0.7722 Intermediate Similarity NPD7199 Phase 2
0.7668 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD7871 Phase 2
0.7665 Intermediate Similarity NPD7870 Phase 2
0.7619 Intermediate Similarity NPD1510 Phase 2
0.7614 Intermediate Similarity NPD7698 Approved
0.7614 Intermediate Similarity NPD7697 Approved
0.7614 Intermediate Similarity NPD7696 Phase 3
0.7611 Intermediate Similarity NPD919 Approved
0.7611 Intermediate Similarity NPD6234 Discontinued
0.7602 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD8319 Approved
0.7576 Intermediate Similarity NPD8320 Phase 1
0.7574 Intermediate Similarity NPD2796 Approved
0.755 Intermediate Similarity NPD7701 Phase 2
0.7529 Intermediate Similarity NPD7266 Discontinued
0.7528 Intermediate Similarity NPD37 Approved
0.7525 Intermediate Similarity NPD7783 Phase 2
0.7525 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3750 Approved
0.75 Intermediate Similarity NPD4965 Approved
0.75 Intermediate Similarity NPD4967 Phase 2
0.75 Intermediate Similarity NPD4966 Approved
0.7474 Intermediate Similarity NPD6535 Approved
0.7474 Intermediate Similarity NPD6534 Approved
0.7471 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7449 Intermediate Similarity NPD7699 Phase 2
0.7449 Intermediate Similarity NPD7700 Phase 2
0.7447 Intermediate Similarity NPD7240 Approved
0.7446 Intermediate Similarity NPD3926 Phase 2
0.744 Intermediate Similarity NPD230 Phase 1
0.7438 Intermediate Similarity NPD7801 Approved
0.7435 Intermediate Similarity NPD8150 Discontinued
0.7432 Intermediate Similarity NPD1247 Approved
0.7384 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD943 Approved
0.7381 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD1613 Approved
0.7368 Intermediate Similarity NPD1551 Phase 2
0.7344 Intermediate Similarity NPD8434 Phase 2
0.7341 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD1933 Approved
0.7327 Intermediate Similarity NPD7584 Approved
0.73 Intermediate Similarity NPD6823 Phase 2
0.7299 Intermediate Similarity NPD4628 Phase 3
0.7278 Intermediate Similarity NPD1240 Approved
0.7263 Intermediate Similarity NPD7458 Discontinued
0.7235 Intermediate Similarity NPD447 Suspended
0.7232 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD3748 Approved
0.7209 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD1607 Approved
0.7178 Intermediate Similarity NPD7680 Approved
0.7168 Intermediate Similarity NPD2935 Discontinued
0.7167 Intermediate Similarity NPD3226 Approved
0.716 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6798 Discontinued
0.7151 Intermediate Similarity NPD920 Approved
0.7143 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD2533 Approved
0.7135 Intermediate Similarity NPD2534 Approved
0.7135 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD2532 Approved
0.7122 Intermediate Similarity NPD7585 Approved
0.712 Intermediate Similarity NPD5953 Discontinued
0.7118 Intermediate Similarity NPD6233 Phase 2
0.7083 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD7390 Discontinued
0.7073 Intermediate Similarity NPD7583 Approved
0.7072 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD6212 Phase 3
0.7071 Intermediate Similarity NPD6213 Phase 3
0.7065 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD2313 Discontinued
0.7056 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD7286 Phase 2
0.7 Intermediate Similarity NPD3027 Phase 3
0.6968 Remote Similarity NPD8127 Discontinued
0.6964 Remote Similarity NPD1203 Approved
0.6949 Remote Similarity NPD1243 Approved
0.6946 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6944 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6942 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6941 Remote Similarity NPD6832 Phase 2
0.6932 Remote Similarity NPD2346 Discontinued
0.6919 Remote Similarity NPD4287 Approved
0.6914 Remote Similarity NPD7033 Discontinued
0.6914 Remote Similarity NPD2799 Discontinued
0.6886 Remote Similarity NPD9269 Phase 2
0.6882 Remote Similarity NPD5353 Approved
0.6875 Remote Similarity NPD5404 Approved
0.6875 Remote Similarity NPD5406 Approved
0.6875 Remote Similarity NPD5408 Approved
0.6875 Remote Similarity NPD5405 Approved
0.6872 Remote Similarity NPD7549 Discontinued
0.6865 Remote Similarity NPD6844 Discontinued
0.6857 Remote Similarity NPD7097 Phase 1
0.6854 Remote Similarity NPD1652 Phase 2
0.6854 Remote Similarity NPD2800 Approved
0.6842 Remote Similarity NPD4908 Phase 1
0.6839 Remote Similarity NPD6355 Discontinued
0.6839 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6836 Remote Similarity NPD2344 Approved
0.6826 Remote Similarity NPD1091 Approved
0.6821 Remote Similarity NPD7038 Approved
0.6821 Remote Similarity NPD7039 Approved
0.6816 Remote Similarity NPD8166 Discontinued
0.6816 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6806 Remote Similarity NPD5242 Approved
0.6804 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6804 Remote Similarity NPD8059 Phase 3
0.6786 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6784 Remote Similarity NPD9494 Approved
0.6782 Remote Similarity NPD4363 Phase 3
0.6782 Remote Similarity NPD4360 Phase 2
0.6763 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6761 Remote Similarity NPD7930 Approved
0.676 Remote Similarity NPD6674 Discontinued
0.6754 Remote Similarity NPD5711 Approved
0.6754 Remote Similarity NPD7229 Phase 3
0.6754 Remote Similarity NPD5710 Approved
0.6743 Remote Similarity NPD5123 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