Structure

Physi-Chem Properties

Molecular Weight:  798.29
Volume:  751.648
LogP:  1.154
LogD:  -0.116
LogS:  -2.86
# Rotatable Bonds:  15
TPSA:  282.21
# H-Bond Aceptor:  19
# H-Bond Donor:  9
# Rings:  5
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.077
Synthetic Accessibility Score:  5.327
Fsp3:  0.595
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.529
MDCK Permeability:  9.79136602836661e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.946
20% Bioavailability (F20%):  0.335
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.038
Plasma Protein Binding (PPB):  92.12435150146484%
Volume Distribution (VD):  0.102
Pgp-substrate:  6.731788635253906%

ADMET: Metabolism

CYP1A2-inhibitor:  0.032
CYP1A2-substrate:  0.107
CYP2C19-inhibitor:  0.052
CYP2C19-substrate:  0.167
CYP2C9-inhibitor:  0.027
CYP2C9-substrate:  0.076
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.149
CYP3A4-inhibitor:  0.05
CYP3A4-substrate:  0.02

ADMET: Excretion

Clearance (CL):  0.846
Half-life (T1/2):  0.613

ADMET: Toxicity

hERG Blockers:  0.715
Human Hepatotoxicity (H-HT):  0.688
Drug-inuced Liver Injury (DILI):  0.89
AMES Toxicity:  0.449
Rat Oral Acute Toxicity:  0.042
Maximum Recommended Daily Dose:  0.01
Skin Sensitization:  0.957
Carcinogencity:  0.022
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.521

Download Data

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

  Natural Product: NPC259347

Natural Product ID:  NPC259347
Common Name*:   2-(3-Hydroxy-4-Methoxy-Phenyl)-Ethyl-O-(Alpha-L-Rhamnosyl)-(1->3)-O-(Alpha-L-Rhamnosyl)-(1->6)-4-O-E-Feruloyl-Beta-D-Glucopyranoside
IUPAC Name:   [(2R,3R,4R,5R,6R)-5-hydroxy-6-[2-(3-hydroxy-4-methoxyphenyl)ethoxy]-4-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  FAWZJJGBNPBDHC-YTODNAJMSA-N
Standard InCHI:  InChI=1S/C37H50O19/c1-16-26(41)28(43)30(45)35(52-16)51-15-24-33(55-25(40)10-7-18-5-8-20(38)23(14-18)49-4)34(56-37-31(46)29(44)27(42)17(2)53-37)32(47)36(54-24)50-12-11-19-6-9-22(48-3)21(39)13-19/h5-10,13-14,16-17,24,26-39,41-47H,11-12,15H2,1-4H3/b10-7+/t16-,17-,24+,26-,27-,28+,29+,30+,31+,32+,33+,34+,35+,36+,37-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](OCCc3ccc(c(c3)O)OC)O2)O)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)OC(=O)/C=C/c2ccc(c(c2)OC)O)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL506920
PubChem CID:   10581173
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0000198] Oligosaccharides

*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
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[9834166]
NPO16764 Penstemon linarioides Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[9834166]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4443 Digitalis purpurea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16764 Penstemon linarioides Species Plantaginaceae 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
NPT182 Individual Protein Protein kinase C alpha Homo sapiens IC50 = 125000.0 nM PMID[473276]

☑ 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 NPC259347 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 NPC476398
1.0 High Similarity NPC473427
1.0 High Similarity NPC471062
1.0 High Similarity NPC470933
1.0 High Similarity NPC476386
1.0 High Similarity NPC94871
1.0 High Similarity NPC306890
0.993 High Similarity NPC257970
0.993 High Similarity NPC470927
0.9858 High Similarity NPC232992
0.9716 High Similarity NPC34927
0.9716 High Similarity NPC476382
0.9716 High Similarity NPC100998
0.9716 High Similarity NPC252292
0.9716 High Similarity NPC34587
0.9653 High Similarity NPC188393
0.9653 High Similarity NPC470934
0.9574 High Similarity NPC476397
0.9574 High Similarity NPC264632
0.9574 High Similarity NPC175214
0.9574 High Similarity NPC476381
0.9574 High Similarity NPC96795
0.9574 High Similarity NPC269141
0.9574 High Similarity NPC112
0.9574 High Similarity NPC76406
0.9574 High Similarity NPC298257
0.9574 High Similarity NPC119537
0.9574 High Similarity NPC476375
0.9574 High Similarity NPC476384
0.9574 High Similarity NPC476378
0.9574 High Similarity NPC476380
0.9574 High Similarity NPC205864
0.9574 High Similarity NPC247032
0.951 High Similarity NPC476865
0.9507 High Similarity NPC64195
0.9504 High Similarity NPC265648
0.9504 High Similarity NPC222433
0.9504 High Similarity NPC140502
0.9441 High Similarity NPC476869
0.9441 High Similarity NPC476868
0.9441 High Similarity NPC476864
0.9441 High Similarity NPC83743
0.9441 High Similarity NPC262182
0.9441 High Similarity NPC287615
0.9441 High Similarity NPC216819
0.9441 High Similarity NPC476866
0.9433 High Similarity NPC476385
0.9433 High Similarity NPC476377
0.9433 High Similarity NPC47471
0.9433 High Similarity NPC134405
0.9384 High Similarity NPC476871
0.9379 High Similarity NPC215095
0.9379 High Similarity NPC261122
0.9379 High Similarity NPC3460
0.9379 High Similarity NPC199311
0.9379 High Similarity NPC80732
0.9379 High Similarity NPC300262
0.9379 High Similarity NPC28651
0.9379 High Similarity NPC201148
0.9379 High Similarity NPC192763
0.9379 High Similarity NPC210611
0.9375 High Similarity NPC229505
0.9371 High Similarity NPC476867
0.9362 High Similarity NPC473799
0.9362 High Similarity NPC475530
0.932 High Similarity NPC7145
0.932 High Similarity NPC143480
0.932 High Similarity NPC85192
0.932 High Similarity NPC125823
0.9301 High Similarity NPC478239
0.9291 High Similarity NPC68092
0.9291 High Similarity NPC197316
0.9291 High Similarity NPC472350
0.9291 High Similarity NPC81515
0.9291 High Similarity NPC64141
0.9291 High Similarity NPC89105
0.9291 High Similarity NPC476383
0.9291 High Similarity NPC205195
0.9257 High Similarity NPC478268
0.9236 High Similarity NPC110063
0.9236 High Similarity NPC296954
0.9236 High Similarity NPC196063
0.9236 High Similarity NPC300894
0.9236 High Similarity NPC141455
0.9231 High Similarity NPC157816
0.922 High Similarity NPC78363
0.922 High Similarity NPC260425
0.922 High Similarity NPC476376
0.9184 High Similarity NPC106138
0.9184 High Similarity NPC283839
0.9184 High Similarity NPC90896
0.9167 High Similarity NPC113680
0.9167 High Similarity NPC105005
0.9167 High Similarity NPC278961
0.9161 High Similarity NPC186406
0.9149 High Similarity NPC157554
0.9128 High Similarity NPC289967
0.9128 High Similarity NPC472612
0.9128 High Similarity NPC472611
0.911 High Similarity NPC199928
0.9103 High Similarity NPC232228
0.9097 High Similarity NPC473873
0.9097 High Similarity NPC473792
0.9091 High Similarity NPC246024
0.9091 High Similarity NPC202700
0.9078 High Similarity NPC263829
0.9054 High Similarity NPC478242
0.9026 High Similarity NPC149873
0.9026 High Similarity NPC7191
0.9021 High Similarity NPC226005
0.9021 High Similarity NPC100389
0.9014 High Similarity NPC177035
0.9014 High Similarity NPC52277
0.9014 High Similarity NPC199459
0.9013 High Similarity NPC11411
0.9007 High Similarity NPC287597
0.9007 High Similarity NPC886
0.9007 High Similarity NPC35731
0.9007 High Similarity NPC135127
0.9007 High Similarity NPC34293
0.8973 High Similarity NPC292443
0.8958 High Similarity NPC106944
0.8954 High Similarity NPC471878
0.8951 High Similarity NPC126206
0.8951 High Similarity NPC470413
0.8951 High Similarity NPC138738
0.8947 High Similarity NPC131532
0.8944 High Similarity NPC476870
0.8912 High Similarity NPC274960
0.8912 High Similarity NPC143120
0.8912 High Similarity NPC473909
0.8904 High Similarity NPC40305
0.8896 High Similarity NPC478269
0.8889 High Similarity NPC321638
0.8889 High Similarity NPC328273
0.8889 High Similarity NPC321184
0.8889 High Similarity NPC171134
0.8881 High Similarity NPC37468
0.8881 High Similarity NPC471665
0.8881 High Similarity NPC186418
0.8881 High Similarity NPC471664
0.8874 High Similarity NPC476352
0.8874 High Similarity NPC106818
0.8874 High Similarity NPC215060
0.8865 High Similarity NPC473285
0.8859 High Similarity NPC23677
0.8859 High Similarity NPC478237
0.8844 High Similarity NPC297342
0.8839 High Similarity NPC478265
0.8819 High Similarity NPC304152
0.8816 High Similarity NPC87403
0.8816 High Similarity NPC150442
0.8808 High Similarity NPC473621
0.8797 High Similarity NPC59516
0.8794 High Similarity NPC235294
0.8794 High Similarity NPC65942
0.8794 High Similarity NPC138777
0.8794 High Similarity NPC246869
0.8794 High Similarity NPC46137
0.8794 High Similarity NPC225384
0.8794 High Similarity NPC248307
0.8782 High Similarity NPC478267
0.8767 High Similarity NPC472711
0.8766 High Similarity NPC478266
0.875 High Similarity NPC169404
0.875 High Similarity NPC53587
0.875 High Similarity NPC176186
0.8742 High Similarity NPC475224
0.8741 High Similarity NPC187194
0.8741 High Similarity NPC471883
0.8733 High Similarity NPC280945
0.8733 High Similarity NPC93924
0.8733 High Similarity NPC116229
0.8732 High Similarity NPC254275
0.8716 High Similarity NPC471063
0.871 High Similarity NPC226759
0.8707 High Similarity NPC469559
0.8696 High Similarity NPC469775
0.8696 High Similarity NPC32723
0.8696 High Similarity NPC295941
0.8696 High Similarity NPC135334
0.8696 High Similarity NPC469776
0.8696 High Similarity NPC469774
0.8696 High Similarity NPC469777
0.8696 High Similarity NPC469773
0.8696 High Similarity NPC469778
0.8696 High Similarity NPC469772
0.8696 High Similarity NPC100925
0.8693 High Similarity NPC471874
0.8688 High Similarity NPC658
0.8688 High Similarity NPC197708
0.8684 High Similarity NPC478249
0.8684 High Similarity NPC269914
0.8675 High Similarity NPC111785
0.8675 High Similarity NPC475250
0.8671 High Similarity NPC227297
0.8667 High Similarity NPC473480
0.8667 High Similarity NPC97240
0.8667 High Similarity NPC15538
0.8667 High Similarity NPC175275

  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 NPC259347 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
0.9291 High Similarity NPD7266 Discontinued
0.8431 Intermediate Similarity NPD1653 Approved
0.8293 Intermediate Similarity NPD7472 Approved
0.8293 Intermediate Similarity NPD7074 Phase 3
0.8232 Intermediate Similarity NPD7054 Approved
0.8193 Intermediate Similarity NPD7685 Pre-registration
0.8171 Intermediate Similarity NPD7228 Approved
0.8144 Intermediate Similarity NPD7808 Phase 3
0.8084 Intermediate Similarity NPD7251 Discontinued
0.8024 Intermediate Similarity NPD6797 Phase 2
0.8014 Intermediate Similarity NPD3027 Phase 3
0.7937 Intermediate Similarity NPD8455 Phase 2
0.7824 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD7240 Approved
0.7744 Intermediate Similarity NPD6234 Discontinued
0.7738 Intermediate Similarity NPD3818 Discontinued
0.7733 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD1613 Approved
0.773 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6190 Approved
0.7677 Intermediate Similarity NPD6674 Discontinued
0.7674 Intermediate Similarity NPD8312 Approved
0.7674 Intermediate Similarity NPD8313 Approved
0.7654 Intermediate Similarity NPD37 Approved
0.7622 Intermediate Similarity NPD4967 Phase 2
0.7622 Intermediate Similarity NPD4966 Approved
0.7622 Intermediate Similarity NPD4965 Approved
0.7619 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD6166 Phase 2
0.7619 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7467 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD3705 Approved
0.7466 Intermediate Similarity NPD1091 Approved
0.7453 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD1934 Approved
0.74 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD1357 Approved
0.7374 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD6559 Discontinued
0.7355 Intermediate Similarity NPD7097 Phase 1
0.7351 Intermediate Similarity NPD7680 Approved
0.7337 Intermediate Similarity NPD7199 Phase 2
0.7337 Intermediate Similarity NPD8127 Discontinued
0.7322 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD228 Approved
0.7296 Intermediate Similarity NPD4628 Phase 3
0.7296 Intermediate Similarity NPD8166 Discontinued
0.7289 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD1465 Phase 2
0.7283 Intermediate Similarity NPD5844 Phase 1
0.7246 Intermediate Similarity NPD3817 Phase 2
0.7241 Intermediate Similarity NPD5536 Phase 2
0.7212 Intermediate Similarity NPD4380 Phase 2
0.7186 Intermediate Similarity NPD2977 Approved
0.7186 Intermediate Similarity NPD2801 Approved
0.7186 Intermediate Similarity NPD2978 Approved
0.7161 Intermediate Similarity NPD4060 Phase 1
0.716 Intermediate Similarity NPD7075 Discontinued
0.7151 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD1652 Phase 2
0.7115 Intermediate Similarity NPD230 Phase 1
0.7115 Intermediate Similarity NPD4340 Discontinued
0.7101 Intermediate Similarity NPD3882 Suspended
0.7099 Intermediate Similarity NPD5058 Phase 3
0.7097 Intermediate Similarity NPD6233 Phase 2
0.7083 Intermediate Similarity NPD5283 Phase 1
0.7078 Intermediate Similarity NPD7095 Approved
0.7068 Intermediate Similarity NPD8151 Discontinued
0.7059 Intermediate Similarity NPD2861 Phase 2
0.7051 Intermediate Similarity NPD3620 Phase 2
0.7051 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD7458 Discontinued
0.7041 Intermediate Similarity NPD5402 Approved
0.7029 Intermediate Similarity NPD3751 Discontinued
0.7022 Intermediate Similarity NPD7549 Discontinued
0.7021 Intermediate Similarity NPD1358 Approved
0.702 Intermediate Similarity NPD2982 Phase 2
0.702 Intermediate Similarity NPD2983 Phase 2
0.7014 Intermediate Similarity NPD7843 Approved
0.7013 Intermediate Similarity NPD4908 Phase 1
0.7006 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD5124 Phase 1
0.7006 Intermediate Similarity NPD1933 Approved
0.6994 Remote Similarity NPD6232 Discontinued
0.6988 Remote Similarity NPD3687 Approved
0.6988 Remote Similarity NPD3686 Approved
0.6982 Remote Similarity NPD7819 Suspended
0.6982 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6971 Remote Similarity NPD7473 Discontinued
0.6964 Remote Similarity NPD6386 Approved
0.6964 Remote Similarity NPD6385 Approved
0.6962 Remote Similarity NPD6653 Approved
0.6959 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6954 Remote Similarity NPD2981 Phase 2
0.6951 Remote Similarity NPD1511 Approved
0.6948 Remote Similarity NPD3018 Phase 2
0.6948 Remote Similarity NPD9494 Approved
0.6944 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6943 Remote Similarity NPD1558 Phase 1
0.6937 Remote Similarity NPD2935 Discontinued
0.6933 Remote Similarity NPD3496 Discontinued
0.6928 Remote Similarity NPD5403 Approved
0.6923 Remote Similarity NPD6798 Discontinued
0.6923 Remote Similarity NPD6841 Approved
0.6923 Remote Similarity NPD6843 Phase 3
0.6923 Remote Similarity NPD6842 Approved
0.6923 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6918 Remote Similarity NPD4536 Approved
0.6918 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6918 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6918 Remote Similarity NPD4538 Approved
0.6914 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6914 Remote Similarity NPD3060 Approved
0.6907 Remote Similarity NPD7783 Phase 2
0.6907 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6355 Discontinued
0.6897 Remote Similarity NPD3787 Discontinued
0.6895 Remote Similarity NPD7435 Discontinued
0.6894 Remote Similarity NPD5763 Approved
0.6894 Remote Similarity NPD5762 Approved
0.6887 Remote Similarity NPD422 Phase 1
0.6879 Remote Similarity NPD5494 Approved
0.6872 Remote Similarity NPD7038 Approved
0.6872 Remote Similarity NPD7039 Approved
0.6871 Remote Similarity NPD7157 Approved
0.6871 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6871 Remote Similarity NPD4110 Phase 3
0.6867 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6867 Remote Similarity NPD1512 Approved
0.6848 Remote Similarity NPD4357 Discontinued
0.6845 Remote Similarity NPD3455 Phase 2
0.6831 Remote Similarity NPD3134 Approved
0.6824 Remote Similarity NPD6801 Discontinued
0.681 Remote Similarity NPD4237 Approved
0.681 Remote Similarity NPD7421 Clinical (unspecified phase)
0.681 Remote Similarity NPD4236 Phase 3
0.6807 Remote Similarity NPD5401 Approved
0.6807 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6806 Remote Similarity NPD7697 Approved
0.6806 Remote Similarity NPD7698 Approved
0.6806 Remote Similarity NPD3021 Approved
0.6806 Remote Similarity NPD7696 Phase 3
0.6806 Remote Similarity NPD3022 Approved
0.6805 Remote Similarity NPD7028 Phase 2
0.6802 Remote Similarity NPD7768 Phase 2
0.6792 Remote Similarity NPD447 Suspended
0.679 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6784 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6784 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6781 Remote Similarity NPD5535 Approved
0.6776 Remote Similarity NPD1610 Phase 2
0.6772 Remote Similarity NPD4062 Phase 3
0.6771 Remote Similarity NPD8320 Phase 1
0.6771 Remote Similarity NPD8319 Approved
0.677 Remote Similarity NPD5588 Approved
0.677 Remote Similarity NPD5960 Phase 3
0.677 Remote Similarity NPD4108 Discontinued
0.677 Remote Similarity NPD7033 Discontinued
0.6769 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6769 Remote Similarity NPD7874 Approved
0.6768 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6768 Remote Similarity NPD3750 Approved
0.6768 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6765 Remote Similarity NPD7411 Suspended
0.6755 Remote Similarity NPD4626 Approved
0.6755 Remote Similarity NPD5126 Approved
0.6755 Remote Similarity NPD5125 Phase 3
0.6754 Remote Similarity NPD6823 Phase 2
0.6753 Remote Similarity NPD3225 Approved
0.6753 Remote Similarity NPD7701 Phase 2
0.6753 Remote Similarity NPD8651 Approved
0.6747 Remote Similarity NPD6799 Approved
0.6744 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6744 Remote Similarity NPD5353 Approved
0.6737 Remote Similarity NPD6776 Approved
0.6737 Remote Similarity NPD6777 Approved
0.6737 Remote Similarity NPD6778 Approved
0.6737 Remote Similarity NPD6779 Approved
0.6737 Remote Similarity NPD6782 Approved
0.6737 Remote Similarity NPD6780 Approved
0.6737 Remote Similarity NPD6781 Approved
0.6736 Remote Similarity NPD2684 Approved
0.6733 Remote Similarity NPD1548 Phase 1
0.673 Remote Similarity NPD4140 Approved
0.6723 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6707 Remote Similarity NPD5177 Phase 3
0.6707 Remote Similarity NPD3536 Discontinued
0.6689 Remote Similarity NPD5691 Approved
0.6687 Remote Similarity NPD1375 Discontinued
0.6687 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6685 Remote Similarity NPD8150 Discontinued

  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