Structure

Physi-Chem Properties

Molecular Weight:  406.13
Volume:  389.464
LogP:  1.323
LogD:  1.126
LogS:  -2.528
# Rotatable Bonds:  7
TPSA:  145.91
# H-Bond Aceptor:  9
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.416
Synthetic Accessibility Score:  3.477
Fsp3:  0.35
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.256
MDCK Permeability:  1.3620451682072598e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.491
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.309
Plasma Protein Binding (PPB):  89.92428588867188%
Volume Distribution (VD):  0.764
Pgp-substrate:  6.1788225173950195%

ADMET: Metabolism

CYP1A2-inhibitor:  0.238
CYP1A2-substrate:  0.036
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.083
CYP2C9-inhibitor:  0.035
CYP2C9-substrate:  0.172
CYP2D6-inhibitor:  0.687
CYP2D6-substrate:  0.179
CYP3A4-inhibitor:  0.018
CYP3A4-substrate:  0.106

ADMET: Excretion

Clearance (CL):  5.202
Half-life (T1/2):  0.888

ADMET: Toxicity

hERG Blockers:  0.17
Human Hepatotoxicity (H-HT):  0.02
Drug-inuced Liver Injury (DILI):  0.856
AMES Toxicity:  0.227
Rat Oral Acute Toxicity:  0.006
Maximum Recommended Daily Dose:  0.001
Skin Sensitization:  0.399
Carcinogencity:  0.326
Eye Corrosion:  0.003
Eye Irritation:  0.582
Respiratory Toxicity:  0.012

Download Data

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

  Natural Product: NPC302989

Natural Product ID:  NPC302989
Common Name*:   Benzyl 2-O-Beta-D-Glucopyranosyl-2,6-Dihydroxybenzoate
IUPAC Name:   benzyl 2-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
Synonyms:  
Standard InCHIKey:  GTFARABJCNHOHO-UVNCQSPWSA-N
Standard InCHI:  InChI=1S/C20H22O9/c21-9-14-16(23)17(24)18(25)20(29-14)28-13-8-4-7-12(22)15(13)19(26)27-10-11-5-2-1-3-6-11/h1-8,14,16-18,20-25H,9-10H2/t14-,16-,17+,18-,20-/m1/s1
SMILES:  c1ccc(cc1)COC(=O)c1c(cccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3092661
PubChem CID:   636610
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0004165] Phenolic 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
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1002/elan.200403102]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2012.02.124]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[11077184]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[11141124]
NPO3699 Acacia aulacocarpa Species Fabaceae Eukaryota n.a. leaf n.a. PMID[11735581]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[15844965]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[17602526]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7569 Guatteria boliviana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8418 Anemone flaccida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19948 Neolentinus lepideus Species Gloeophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4823 Psiadia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4823 Psiadia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19948 Neolentinus lepideus Species Gloeophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8418 Anemone flaccida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5155 Peritassa compta Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5196 Eupatorium argentinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7569 Guatteria boliviana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3699 Acacia aulacocarpa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO471 Ardisia neriifolia Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3597 Rheedia acuminata Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6729 Juniperus brevifolia Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6237 Cryptocarya aschersoniana Species Lauraceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition < 30.0 % PMID[534827]

☑ 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 NPC302989 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
0.9589 High Similarity NPC260604
0.9589 High Similarity NPC299435
0.9459 High Similarity NPC127406
0.9433 High Similarity NPC31081
0.9433 High Similarity NPC245219
0.9396 High Similarity NPC43638
0.9388 High Similarity NPC88484
0.9388 High Similarity NPC259182
0.9388 High Similarity NPC259767
0.9388 High Similarity NPC121001
0.9324 High Similarity NPC143851
0.9324 High Similarity NPC39360
0.9324 High Similarity NPC29763
0.9324 High Similarity NPC210003
0.9324 High Similarity NPC83283
0.9324 High Similarity NPC106625
0.9262 High Similarity NPC27408
0.9262 High Similarity NPC26195
0.9262 High Similarity NPC99233
0.9262 High Similarity NPC95090
0.9262 High Similarity NPC97052
0.9262 High Similarity NPC169248
0.9262 High Similarity NPC72649
0.9262 High Similarity NPC39351
0.9247 High Similarity NPC22137
0.9211 High Similarity NPC129217
0.9211 High Similarity NPC282169
0.9211 High Similarity NPC224530
0.9211 High Similarity NPC159579
0.9211 High Similarity NPC270675
0.9211 High Similarity NPC85707
0.9211 High Similarity NPC101636
0.9211 High Similarity NPC259957
0.9211 High Similarity NPC216496
0.9211 High Similarity NPC217950
0.9211 High Similarity NPC195685
0.9211 High Similarity NPC477628
0.9211 High Similarity NPC472994
0.9211 High Similarity NPC210961
0.9211 High Similarity NPC48093
0.9211 High Similarity NPC477629
0.92 High Similarity NPC170475
0.92 High Similarity NPC307938
0.92 High Similarity NPC323593
0.92 High Similarity NPC265480
0.92 High Similarity NPC203500
0.92 High Similarity NPC149368
0.92 High Similarity NPC206378
0.9195 High Similarity NPC92153
0.9195 High Similarity NPC230439
0.9195 High Similarity NPC299761
0.9195 High Similarity NPC279281
0.9195 High Similarity NPC185103
0.9184 High Similarity NPC100818
0.9178 High Similarity NPC140722
0.9178 High Similarity NPC4958
0.9178 High Similarity NPC92054
0.9161 High Similarity NPC65833
0.915 High Similarity NPC472876
0.915 High Similarity NPC298171
0.915 High Similarity NPC27942
0.9139 High Similarity NPC135391
0.9139 High Similarity NPC78263
0.9139 High Similarity NPC156457
0.9139 High Similarity NPC44931
0.9139 High Similarity NPC258035
0.9139 High Similarity NPC197896
0.9139 High Similarity NPC122809
0.9139 High Similarity NPC6985
0.9139 High Similarity NPC129827
0.9139 High Similarity NPC473512
0.9139 High Similarity NPC182634
0.9139 High Similarity NPC197304
0.9139 High Similarity NPC161749
0.9139 High Similarity NPC133671
0.9139 High Similarity NPC65003
0.9139 High Similarity NPC23817
0.9139 High Similarity NPC313163
0.9139 High Similarity NPC77672
0.9139 High Similarity NPC108831
0.9139 High Similarity NPC60966
0.9139 High Similarity NPC54802
0.9128 High Similarity NPC215811
0.9122 High Similarity NPC191154
0.9122 High Similarity NPC131874
0.9116 High Similarity NPC199335
0.9091 High Similarity NPC121703
0.9091 High Similarity NPC80068
0.9079 High Similarity NPC473634
0.9079 High Similarity NPC22062
0.9079 High Similarity NPC41121
0.9079 High Similarity NPC320283
0.9079 High Similarity NPC43761
0.9079 High Similarity NPC111929
0.9079 High Similarity NPC104677
0.9079 High Similarity NPC472459
0.9079 High Similarity NPC73511
0.9079 High Similarity NPC138811
0.9079 High Similarity NPC308265
0.9073 High Similarity NPC261866
0.906 High Similarity NPC134819
0.9048 High Similarity NPC83975
0.9048 High Similarity NPC23084
0.9032 High Similarity NPC72016
0.9032 High Similarity NPC205824
0.9032 High Similarity NPC139060
0.9032 High Similarity NPC19240
0.9032 High Similarity NPC85751
0.9032 High Similarity NPC129264
0.902 High Similarity NPC271479
0.902 High Similarity NPC470405
0.902 High Similarity NPC271270
0.902 High Similarity NPC142860
0.902 High Similarity NPC200708
0.902 High Similarity NPC97285
0.902 High Similarity NPC187379
0.902 High Similarity NPC471079
0.902 High Similarity NPC472320
0.902 High Similarity NPC473623
0.902 High Similarity NPC246469
0.902 High Similarity NPC136761
0.902 High Similarity NPC304741
0.902 High Similarity NPC153342
0.9013 High Similarity NPC288084
0.8993 High Similarity NPC213723
0.8993 High Similarity NPC477240
0.8993 High Similarity NPC106025
0.8993 High Similarity NPC93619
0.8993 High Similarity NPC214454
0.8974 High Similarity NPC262222
0.8974 High Similarity NPC260504
0.8974 High Similarity NPC64425
0.8974 High Similarity NPC89809
0.8974 High Similarity NPC473278
0.8974 High Similarity NPC298666
0.8974 High Similarity NPC68592
0.8961 High Similarity NPC64305
0.8961 High Similarity NPC303913
0.8961 High Similarity NPC476215
0.8961 High Similarity NPC135846
0.8961 High Similarity NPC297987
0.8961 High Similarity NPC181465
0.8961 High Similarity NPC253788
0.8961 High Similarity NPC173582
0.8961 High Similarity NPC246943
0.8961 High Similarity NPC116458
0.8961 High Similarity NPC139320
0.8961 High Similarity NPC163242
0.8961 High Similarity NPC265885
0.8961 High Similarity NPC47923
0.8961 High Similarity NPC276377
0.8961 High Similarity NPC473438
0.8961 High Similarity NPC170052
0.8961 High Similarity NPC215710
0.8961 High Similarity NPC470125
0.8961 High Similarity NPC249281
0.8947 High Similarity NPC45165
0.8947 High Similarity NPC473657
0.8947 High Similarity NPC295613
0.894 High Similarity NPC211158
0.894 High Similarity NPC78021
0.894 High Similarity NPC268950
0.894 High Similarity NPC87304
0.894 High Similarity NPC108706
0.8933 High Similarity NPC190217
0.8919 High Similarity NPC218685
0.8917 High Similarity NPC116745
0.891 High Similarity NPC7752
0.8903 High Similarity NPC300537
0.8903 High Similarity NPC259834
0.8903 High Similarity NPC127782
0.8903 High Similarity NPC150164
0.8903 High Similarity NPC190450
0.8903 High Similarity NPC189142
0.8903 High Similarity NPC475382
0.8903 High Similarity NPC131745
0.8903 High Similarity NPC77660
0.8903 High Similarity NPC240306
0.8903 High Similarity NPC44947
0.8896 High Similarity NPC328093
0.8889 High Similarity NPC474398
0.8889 High Similarity NPC474441
0.8889 High Similarity NPC474401
0.8889 High Similarity NPC476026
0.8882 High Similarity NPC470603
0.8882 High Similarity NPC470604
0.8882 High Similarity NPC470605
0.8874 High Similarity NPC183536
0.8874 High Similarity NPC34965
0.8859 High Similarity NPC287294
0.8846 High Similarity NPC179198
0.8846 High Similarity NPC191306
0.8846 High Similarity NPC19709
0.8846 High Similarity NPC257566
0.8846 High Similarity NPC311850
0.8846 High Similarity NPC88043
0.8846 High Similarity NPC88023
0.8846 High Similarity NPC168822
0.8846 High Similarity NPC473644
0.8846 High Similarity NPC127415

  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 NPC302989 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
0.9139 High Similarity NPD4381 Clinical (unspecified phase)
0.8792 High Similarity NPD5403 Approved
0.8658 High Similarity NPD5401 Approved
0.8642 High Similarity NPD4338 Clinical (unspecified phase)
0.8625 High Similarity NPD7804 Clinical (unspecified phase)
0.8625 High Similarity NPD7054 Approved
0.858 High Similarity NPD6559 Discontinued
0.8571 High Similarity NPD7074 Phase 3
0.8571 High Similarity NPD7472 Approved
0.8562 High Similarity NPD3818 Discontinued
0.8526 High Similarity NPD7075 Discontinued
0.8519 High Similarity NPD6797 Phase 2
0.8516 High Similarity NPD5402 Approved
0.8497 Intermediate Similarity NPD4380 Phase 2
0.8493 Intermediate Similarity NPD1551 Phase 2
0.8466 Intermediate Similarity NPD7251 Discontinued
0.8435 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8435 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8415 Intermediate Similarity NPD7808 Phase 3
0.8387 Intermediate Similarity NPD6801 Discontinued
0.8378 Intermediate Similarity NPD1549 Phase 2
0.8344 Intermediate Similarity NPD6799 Approved
0.8333 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8269 Intermediate Similarity NPD1934 Approved
0.8267 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8228 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8219 Intermediate Similarity NPD1933 Approved
0.8217 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8205 Intermediate Similarity NPD7411 Suspended
0.8169 Intermediate Similarity NPD1203 Approved
0.8165 Intermediate Similarity NPD3817 Phase 2
0.8144 Intermediate Similarity NPD8313 Approved
0.8144 Intermediate Similarity NPD8312 Approved
0.8143 Intermediate Similarity NPD1091 Approved
0.8129 Intermediate Similarity NPD1653 Approved
0.8098 Intermediate Similarity NPD6166 Phase 2
0.8098 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8098 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8052 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD6599 Discontinued
0.8 Intermediate Similarity NPD6832 Phase 2
0.7987 Intermediate Similarity NPD1511 Approved
0.7987 Intermediate Similarity NPD2801 Approved
0.7987 Intermediate Similarity NPD7819 Suspended
0.7987 Intermediate Similarity NPD8455 Phase 2
0.7937 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7933 Intermediate Similarity NPD1510 Phase 2
0.7908 Intermediate Similarity NPD3750 Approved
0.7891 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD7768 Phase 2
0.7885 Intermediate Similarity NPD1512 Approved
0.7881 Intermediate Similarity NPD2796 Approved
0.7832 Intermediate Similarity NPD9717 Approved
0.7821 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7792 Intermediate Similarity NPD4628 Phase 3
0.7785 Intermediate Similarity NPD1240 Approved
0.7778 Intermediate Similarity NPD3882 Suspended
0.7771 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD7033 Discontinued
0.7682 Intermediate Similarity NPD1607 Approved
0.7662 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD6232 Discontinued
0.7651 Intermediate Similarity NPD2313 Discontinued
0.7647 Intermediate Similarity NPD2935 Discontinued
0.7639 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD5844 Phase 1
0.7622 Intermediate Similarity NPD3749 Approved
0.7616 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD447 Suspended
0.7613 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD1652 Phase 2
0.7603 Intermediate Similarity NPD3225 Approved
0.7593 Intermediate Similarity NPD37 Approved
0.759 Intermediate Similarity NPD7199 Phase 2
0.759 Intermediate Similarity NPD6959 Discontinued
0.7582 Intermediate Similarity NPD3748 Approved
0.7576 Intermediate Similarity NPD6234 Discontinued
0.7574 Intermediate Similarity NPD3751 Discontinued
0.7574 Intermediate Similarity NPD7228 Approved
0.7561 Intermediate Similarity NPD4967 Phase 2
0.7561 Intermediate Similarity NPD4966 Approved
0.7561 Intermediate Similarity NPD4965 Approved
0.7551 Intermediate Similarity NPD2797 Approved
0.755 Intermediate Similarity NPD1613 Approved
0.755 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD1465 Phase 2
0.7545 Intermediate Similarity NPD3787 Discontinued
0.7533 Intermediate Similarity NPD6798 Discontinued
0.7515 Intermediate Similarity NPD7473 Discontinued
0.75 Intermediate Similarity NPD7685 Pre-registration
0.75 Intermediate Similarity NPD1019 Discontinued
0.75 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD7266 Discontinued
0.7484 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD6233 Phase 2
0.7465 Intermediate Similarity NPD9493 Approved
0.7459 Intermediate Similarity NPD7584 Approved
0.7456 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD5494 Approved
0.7423 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD3268 Approved
0.7407 Intermediate Similarity NPD3226 Approved
0.7407 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD422 Phase 1
0.7396 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD7435 Discontinued
0.7386 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD5124 Phase 1
0.7383 Intermediate Similarity NPD2798 Approved
0.7375 Intermediate Similarity NPD2534 Approved
0.7375 Intermediate Similarity NPD2532 Approved
0.7375 Intermediate Similarity NPD2533 Approved
0.7372 Intermediate Similarity NPD2346 Discontinued
0.7361 Intermediate Similarity NPD1548 Phase 1
0.7355 Intermediate Similarity NPD4308 Phase 3
0.7355 Intermediate Similarity NPD2799 Discontinued
0.7348 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD5953 Discontinued
0.7326 Intermediate Similarity NPD7585 Approved
0.7326 Intermediate Similarity NPD7286 Phase 2
0.7322 Intermediate Similarity NPD6779 Approved
0.7322 Intermediate Similarity NPD6780 Approved
0.7322 Intermediate Similarity NPD6777 Approved
0.7322 Intermediate Similarity NPD6781 Approved
0.7322 Intermediate Similarity NPD6778 Approved
0.7322 Intermediate Similarity NPD6782 Approved
0.7322 Intermediate Similarity NPD6776 Approved
0.7312 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD411 Approved
0.7302 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD7783 Phase 2
0.7296 Intermediate Similarity NPD6190 Approved
0.7287 Intermediate Similarity NPD8151 Discontinued
0.7285 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD4908 Phase 1
0.7284 Intermediate Similarity NPD920 Approved
0.7279 Intermediate Similarity NPD1610 Phase 2
0.7273 Intermediate Similarity NPD6355 Discontinued
0.7273 Intermediate Similarity NPD7583 Approved
0.7273 Intermediate Similarity NPD230 Phase 1
0.7267 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD6823 Phase 2
0.7219 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7240 Approved
0.7195 Intermediate Similarity NPD7458 Discontinued
0.719 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7097 Phase 1
0.717 Intermediate Similarity NPD1243 Approved
0.717 Intermediate Similarity NPD2800 Approved
0.716 Intermediate Similarity NPD4662 Approved
0.716 Intermediate Similarity NPD4661 Approved
0.7158 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD7874 Approved
0.7152 Intermediate Similarity NPD5647 Approved
0.7143 Intermediate Similarity NPD4062 Phase 3
0.7124 Intermediate Similarity NPD3027 Phase 3
0.7123 Intermediate Similarity NPD9545 Approved
0.7115 Intermediate Similarity NPD6651 Approved
0.7114 Intermediate Similarity NPD1481 Phase 2
0.7112 Intermediate Similarity NPD7698 Approved
0.7112 Intermediate Similarity NPD7696 Phase 3
0.7112 Intermediate Similarity NPD7697 Approved
0.7097 Intermediate Similarity NPD4307 Phase 2
0.7095 Intermediate Similarity NPD8434 Phase 2
0.7089 Intermediate Similarity NPD6100 Approved
0.7089 Intermediate Similarity NPD6099 Approved
0.7086 Intermediate Similarity NPD3266 Approved
0.7086 Intermediate Similarity NPD3267 Approved
0.7083 Intermediate Similarity NPD4288 Approved
0.7078 Intermediate Similarity NPD1296 Phase 2
0.7074 Intermediate Similarity NPD7870 Phase 2
0.7074 Intermediate Similarity NPD7871 Phase 2
0.7066 Intermediate Similarity NPD6844 Discontinued
0.7062 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD919 Approved
0.7053 Intermediate Similarity NPD7701 Phase 2
0.7051 Intermediate Similarity NPD4340 Discontinued
0.7049 Intermediate Similarity NPD6534 Approved
0.7049 Intermediate Similarity NPD6535 Approved
0.7047 Intermediate Similarity NPD1535 Discovery
0.7044 Intermediate Similarity NPD6002 Phase 3
0.7044 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD6004 Phase 3
0.7044 Intermediate Similarity NPD6005 Phase 3
0.7044 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7440 Discontinued
0.7021 Intermediate Similarity NPD74 Approved
0.7021 Intermediate Similarity NPD9266 Approved
0.7007 Intermediate Similarity NPD1894 Discontinued
0.7 Intermediate Similarity NPD1608 Approved
0.7 Intermediate Similarity NPD8150 Discontinued
0.6987 Remote Similarity NPD943 Approved
0.6984 Remote Similarity NPD8320 Phase 1

  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