Structure

Physi-Chem Properties

Molecular Weight:  742.23
Volume:  682.464
LogP:  -0.312
LogD:  -0.334
LogS:  -2.257
# Rotatable Bonds:  14
TPSA:  304.21
# H-Bond Aceptor:  19
# H-Bond Donor:  11
# Rings:  5
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.056
Synthetic Accessibility Score:  5.331
Fsp3:  0.545
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:  -6.761
MDCK Permeability:  1.6212921764235944e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.998
20% Bioavailability (F20%):  0.995
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.16
Plasma Protein Binding (PPB):  88.80741882324219%
Volume Distribution (VD):  0.228
Pgp-substrate:  15.158685684204102%

ADMET: Metabolism

CYP1A2-inhibitor:  0.019
CYP1A2-substrate:  0.01
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.043
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.053
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.136
CYP3A4-inhibitor:  0.039
CYP3A4-substrate:  0.017

ADMET: Excretion

Clearance (CL):  0.535
Half-life (T1/2):  0.826

ADMET: Toxicity

hERG Blockers:  0.248
Human Hepatotoxicity (H-HT):  0.154
Drug-inuced Liver Injury (DILI):  0.25
AMES Toxicity:  0.171
Rat Oral Acute Toxicity:  0.046
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.971
Carcinogencity:  0.042
Eye Corrosion:  0.003
Eye Irritation:  0.018
Respiratory Toxicity:  0.012

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

  Natural Product: NPC105005

Natural Product ID:  NPC105005
Common Name*:   Fucatoside B
IUPAC Name:   [(2R,3R,4S,5R,6R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-2-(hydroxymethyl)-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:   fucatoside B
Standard InCHIKey:  PPMUODHYYRGJOK-LXOFMWEESA-N
Standard InCHI:  InChI=1S/C33H42O19/c34-11-22-26(50-23(41)6-3-15-1-4-17(36)19(38)9-15)27(51-32-29(44)33(45,13-35)14-48-32)28(52-30-25(43)24(42)21(40)12-47-30)31(49-22)46-8-7-16-2-5-18(37)20(39)10-16/h1-6,9-10,21-22,24-32,34-40,42-45H,7-8,11-14H2/b6-3+/t21-,22-,24+,25-,26-,27+,28-,29+,30+,31-,32+,33-/m1/s1
SMILES:  c1cc(c(cc1/C=C/C(=O)O[C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O[C@H]1[C@@H]([C@@](CO)(CO1)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)OCCc1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1077834
PubChem CID:   44254789
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
NPO4462 Tripterygium doianum Species Celastraceae Eukaryota n.a. branch n.a. PMID[12165306]
NPO14775 Eupenicillium javanicum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17711347]
NPO14775 Eupenicillium javanicum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[18771240]
NPO8662 Lantana fucata Species Verbenaceae Eukaryota n.a. n.a. n.a. PMID[19634889]
NPO4462 Tripterygium doianum Species Celastraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO7362 Thalictrum omeiense Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4462 Tripterygium doianum Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[Phytochemistry, 2004, 65, 2071]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7362 Thalictrum omeiense Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4462 Tripterygium doianum Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8662 Lantana fucata Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4462 Tripterygium doianum Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14775 Eupenicillium javanicum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7362 Thalictrum omeiense Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11291 Styrax benzoin Species Styracaceae 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
NPT1182 Cell Line J774.A1 Mus musculus Inhibition = 81.4 % PMID[475128]
NPT1182 Cell Line J774.A1 Mus musculus Inhibition = 16.41 % PMID[475128]
NPT1182 Cell Line J774.A1 Mus musculus Inhibition = 13.7 % PMID[475128]
NPT1182 Cell Line J774.A1 Mus musculus Inhibition = 94.4 % PMID[475128]
NPT1182 Cell Line J774.A1 Mus musculus Inhibition = 96.1 % PMID[475128]
NPT1182 Cell Line J774.A1 Mus musculus Inhibition = 97.5 % PMID[475128]

☑ 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 NPC105005 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
0.9926 High Similarity NPC300894
0.9926 High Similarity NPC141455
0.9926 High Similarity NPC196063
0.9926 High Similarity NPC296954
0.9783 High Similarity NPC229505
0.9708 High Similarity NPC40305
0.9706 High Similarity NPC476377
0.9706 High Similarity NPC47471
0.9704 High Similarity NPC321638
0.9704 High Similarity NPC205195
0.9704 High Similarity NPC171134
0.9704 High Similarity NPC328273
0.9704 High Similarity NPC321184
0.9632 High Similarity NPC475530
0.9632 High Similarity NPC473799
0.963 High Similarity NPC260425
0.9565 High Similarity NPC476384
0.9565 High Similarity NPC205864
0.9565 High Similarity NPC476380
0.9565 High Similarity NPC247032
0.9565 High Similarity NPC175214
0.9565 High Similarity NPC476378
0.9565 High Similarity NPC476375
0.9565 High Similarity NPC269141
0.9565 High Similarity NPC476397
0.9565 High Similarity NPC264632
0.9565 High Similarity NPC476381
0.9565 High Similarity NPC76406
0.9565 High Similarity NPC96795
0.9565 High Similarity NPC112
0.9565 High Similarity NPC298257
0.9565 High Similarity NPC119537
0.9562 High Similarity NPC134405
0.9562 High Similarity NPC476385
0.9559 High Similarity NPC476383
0.9559 High Similarity NPC197316
0.9559 High Similarity NPC81515
0.9559 High Similarity NPC89105
0.9559 High Similarity NPC472350
0.9559 High Similarity NPC68092
0.9559 High Similarity NPC64141
0.9507 High Similarity NPC188393
0.9507 High Similarity NPC470934
0.9496 High Similarity NPC64195
0.9485 High Similarity NPC78363
0.9407 High Similarity NPC287597
0.9407 High Similarity NPC34293
0.9407 High Similarity NPC886
0.9353 High Similarity NPC222433
0.9353 High Similarity NPC265648
0.9343 High Similarity NPC476376
0.9265 High Similarity NPC471883
0.9259 High Similarity NPC473924
0.9197 High Similarity NPC476870
0.9191 High Similarity NPC254398
0.9185 High Similarity NPC219677
0.9185 High Similarity NPC478255
0.9167 High Similarity NPC471062
0.9167 High Similarity NPC470933
0.9167 High Similarity NPC306890
0.9167 High Similarity NPC259347
0.9167 High Similarity NPC473427
0.9167 High Similarity NPC476398
0.9167 High Similarity NPC476386
0.9167 High Similarity NPC94871
0.9155 High Similarity NPC262182
0.9155 High Similarity NPC83743
0.9155 High Similarity NPC476382
0.9155 High Similarity NPC216819
0.9155 High Similarity NPC34927
0.9155 High Similarity NPC287615
0.9155 High Similarity NPC100998
0.9155 High Similarity NPC34587
0.9155 High Similarity NPC252292
0.9118 High Similarity NPC473285
0.911 High Similarity NPC106818
0.9103 High Similarity NPC470927
0.9103 High Similarity NPC257970
0.9097 High Similarity NPC300262
0.9097 High Similarity NPC201148
0.9097 High Similarity NPC210611
0.9097 High Similarity NPC192763
0.9097 High Similarity NPC215095
0.9097 High Similarity NPC199311
0.9097 High Similarity NPC261122
0.9097 High Similarity NPC3460
0.9097 High Similarity NPC28651
0.9097 High Similarity NPC80732
0.9085 High Similarity NPC476867
0.9085 High Similarity NPC110063
0.9058 High Similarity NPC263829
0.9051 High Similarity NPC28637
0.9048 High Similarity NPC87403
0.9044 High Similarity NPC46137
0.9044 High Similarity NPC235294
0.9037 High Similarity NPC229784
0.9037 High Similarity NPC477293
0.9037 High Similarity NPC477294
0.9028 High Similarity NPC232992
0.9021 High Similarity NPC476868
0.9021 High Similarity NPC476864
0.9021 High Similarity NPC476866
0.9021 High Similarity NPC476869
0.898 High Similarity NPC478268
0.8978 High Similarity NPC254275
0.8963 High Similarity NPC232880
0.8963 High Similarity NPC225307
0.8958 High Similarity NPC476865
0.8944 High Similarity NPC140502
0.8919 High Similarity NPC471874
0.8912 High Similarity NPC125823
0.8912 High Similarity NPC7145
0.8912 High Similarity NPC143480
0.8912 High Similarity NPC85192
0.8905 High Similarity NPC246869
0.8905 High Similarity NPC138777
0.8905 High Similarity NPC225384
0.8904 High Similarity NPC90896
0.8904 High Similarity NPC283839
0.8897 High Similarity NPC184092
0.8889 High Similarity NPC288416
0.8889 High Similarity NPC476873
0.8873 High Similarity NPC186406
0.8857 High Similarity NPC470572
0.8851 High Similarity NPC289967
0.8851 High Similarity NPC472611
0.8851 High Similarity NPC472612
0.8844 High Similarity NPC476871
0.8836 High Similarity NPC473138
0.8836 High Similarity NPC28776
0.8836 High Similarity NPC23677
0.875 High Similarity NPC106677
0.875 High Similarity NPC45224
0.875 High Similarity NPC478239
0.875 High Similarity NPC108659
0.875 High Similarity NPC231607
0.875 High Similarity NPC264900
0.875 High Similarity NPC35288
0.875 High Similarity NPC173150
0.875 High Similarity NPC156692
0.875 High Similarity NPC103533
0.875 High Similarity NPC79715
0.875 High Similarity NPC471882
0.875 High Similarity NPC471881
0.8742 High Similarity NPC11411
0.8741 High Similarity NPC90318
0.8741 High Similarity NPC83218
0.8741 High Similarity NPC126991
0.8732 High Similarity NPC220942
0.8732 High Similarity NPC226005
0.8716 High Similarity NPC69367
0.869 High Similarity NPC292443
0.869 High Similarity NPC232228
0.8681 High Similarity NPC157816
0.8681 High Similarity NPC296643
0.8676 High Similarity NPC94179
0.8676 High Similarity NPC61181
0.8676 High Similarity NPC471157
0.8671 High Similarity NPC202700
0.8652 High Similarity NPC123988
0.8649 High Similarity NPC106138
0.8649 High Similarity NPC478242
0.8636 High Similarity NPC149873
0.8636 High Similarity NPC7191
0.8627 High Similarity NPC478269
0.8621 High Similarity NPC113680
0.8621 High Similarity NPC278961
0.8592 High Similarity NPC154485
0.8592 High Similarity NPC157554
0.8592 High Similarity NPC471872
0.8591 High Similarity NPC475224
0.8581 High Similarity NPC246024
0.8571 High Similarity NPC199928
0.8571 High Similarity NPC473867
0.8571 High Similarity NPC478265
0.8562 High Similarity NPC226759
0.8562 High Similarity NPC297342
0.8562 High Similarity NPC187205
0.8552 High Similarity NPC473792
0.8552 High Similarity NPC473873
0.8551 High Similarity NPC148982
0.8542 High Similarity NPC106944
0.854 High Similarity NPC252114
0.8531 High Similarity NPC84789
0.8531 High Similarity NPC302583
0.8531 High Similarity NPC100558
0.8531 High Similarity NPC310252
0.8519 High Similarity NPC52097
0.8516 High Similarity NPC478267
0.8514 High Similarity NPC18789
0.8497 Intermediate Similarity NPC478266
0.8493 Intermediate Similarity NPC478250
0.8493 Intermediate Similarity NPC46092
0.8483 Intermediate Similarity NPC472711
0.8478 Intermediate Similarity NPC469687
0.8472 Intermediate Similarity NPC100389
0.8462 Intermediate Similarity NPC177035
0.8462 Intermediate Similarity NPC471664
0.8462 Intermediate Similarity NPC199459
0.8462 Intermediate Similarity NPC471665

  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 NPC105005 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
0.9559 High Similarity NPD7266 Discontinued
0.8121 Intermediate Similarity NPD6190 Approved
0.8039 Intermediate Similarity NPD1653 Approved
0.7939 Intermediate Similarity NPD7685 Pre-registration
0.7805 Intermediate Similarity NPD7228 Approved
0.7711 Intermediate Similarity NPD7472 Approved
0.7651 Intermediate Similarity NPD7054 Approved
0.7647 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD7251 Discontinued
0.7605 Intermediate Similarity NPD7074 Phase 3
0.759 Intermediate Similarity NPD3818 Discontinued
0.7574 Intermediate Similarity NPD7808 Phase 3
0.7562 Intermediate Similarity NPD8455 Phase 2
0.756 Intermediate Similarity NPD6797 Phase 2
0.7548 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD6234 Discontinued
0.7483 Intermediate Similarity NPD3027 Phase 3
0.7471 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD1613 Approved
0.7412 Intermediate Similarity NPD7240 Approved
0.7391 Intermediate Similarity NPD37 Approved
0.7362 Intermediate Similarity NPD4966 Approved
0.7362 Intermediate Similarity NPD4967 Phase 2
0.7362 Intermediate Similarity NPD4965 Approved
0.7355 Intermediate Similarity NPD8166 Discontinued
0.7353 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD8312 Approved
0.7326 Intermediate Similarity NPD8313 Approved
0.7317 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD6559 Discontinued
0.7192 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD6674 Discontinued
0.7172 Intermediate Similarity NPD3705 Approved
0.7172 Intermediate Similarity NPD1091 Approved
0.7171 Intermediate Similarity NPD230 Phase 1
0.7135 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD3764 Approved
0.7083 Intermediate Similarity NPD7199 Phase 2
0.7083 Intermediate Similarity NPD1357 Approved
0.7078 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6166 Phase 2
0.7059 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD5058 Phase 3
0.7039 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD5125 Phase 3
0.7034 Intermediate Similarity NPD5126 Approved
0.7027 Intermediate Similarity NPD7680 Approved
0.7022 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD969 Suspended
0.6995 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6982 Remote Similarity NPD8127 Discontinued
0.6978 Remote Similarity NPD3021 Approved
0.6978 Remote Similarity NPD3022 Approved
0.697 Remote Similarity NPD1934 Approved
0.6968 Remote Similarity NPD7097 Phase 1
0.6951 Remote Similarity NPD4380 Phase 2
0.6943 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6928 Remote Similarity NPD2978 Approved
0.6928 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6928 Remote Similarity NPD2977 Approved
0.6928 Remote Similarity NPD1465 Phase 2
0.6918 Remote Similarity NPD4628 Phase 3
0.6901 Remote Similarity NPD7184 Clinical (unspecified phase)
0.689 Remote Similarity NPD3455 Phase 2
0.6887 Remote Similarity NPD2861 Phase 2
0.6883 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6845 Remote Similarity NPD3882 Suspended
0.6839 Remote Similarity NPD4340 Discontinued
0.6839 Remote Similarity NPD5844 Phase 1
0.6805 Remote Similarity NPD7075 Discontinued
0.6797 Remote Similarity NPD7095 Approved
0.6786 Remote Similarity NPD3817 Phase 2
0.6786 Remote Similarity NPD5402 Approved
0.6782 Remote Similarity NPD3751 Discontinued
0.6774 Remote Similarity NPD4060 Phase 1
0.6761 Remote Similarity NPD228 Approved
0.675 Remote Similarity NPD1652 Phase 2
0.6731 Remote Similarity NPD5124 Phase 1
0.6731 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6726 Remote Similarity NPD2801 Approved
0.6722 Remote Similarity NPD8150 Discontinued
0.672 Remote Similarity NPD8319 Approved
0.672 Remote Similarity NPD8320 Phase 1
0.6712 Remote Similarity NPD5536 Phase 2
0.671 Remote Similarity NPD6233 Phase 2
0.6709 Remote Similarity NPD5588 Approved
0.6704 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6688 Remote Similarity NPD6653 Approved
0.6688 Remote Similarity NPD5314 Approved
0.6687 Remote Similarity NPD1511 Approved
0.6667 Remote Similarity NPD3062 Approved
0.6667 Remote Similarity NPD3059 Approved
0.6667 Remote Similarity NPD5403 Approved
0.6667 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7699 Phase 2
0.6667 Remote Similarity NPD5736 Approved
0.6667 Remote Similarity NPD3061 Approved
0.6667 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9269 Phase 2
0.6667 Remote Similarity NPD8151 Discontinued
0.6667 Remote Similarity NPD3620 Phase 2
0.6667 Remote Similarity NPD9545 Approved
0.6667 Remote Similarity NPD7700 Phase 2
0.6647 Remote Similarity NPD7028 Phase 2
0.6647 Remote Similarity NPD3787 Discontinued
0.6646 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6646 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6645 Remote Similarity NPD3094 Phase 2
0.663 Remote Similarity NPD8434 Phase 2
0.6628 Remote Similarity NPD5494 Approved
0.6627 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6627 Remote Similarity NPD7819 Suspended
0.6625 Remote Similarity NPD5763 Approved
0.6625 Remote Similarity NPD5762 Approved
0.6624 Remote Similarity NPD6355 Discontinued
0.6623 Remote Similarity NPD4908 Phase 1
0.6608 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6606 Remote Similarity NPD1512 Approved
0.6606 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6604 Remote Similarity NPD7033 Discontinued
0.6597 Remote Similarity NPD7843 Approved
0.6596 Remote Similarity NPD1358 Approved
0.6592 Remote Similarity NPD7549 Discontinued
0.6587 Remote Similarity NPD7458 Discontinued
0.6579 Remote Similarity NPD7435 Discontinued
0.6577 Remote Similarity NPD9384 Approved
0.6577 Remote Similarity NPD9381 Approved
0.6562 Remote Similarity NPD2935 Discontinued
0.6562 Remote Similarity NPD9570 Approved
0.6561 Remote Similarity NPD943 Approved
0.6554 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6552 Remote Similarity NPD5283 Phase 1
0.6552 Remote Similarity NPD6232 Discontinued
0.6545 Remote Similarity NPD5401 Approved
0.6543 Remote Similarity NPD4236 Phase 3
0.6543 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6543 Remote Similarity NPD4237 Approved
0.6541 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6541 Remote Similarity NPD4536 Approved
0.6541 Remote Similarity NPD4538 Approved
0.6538 Remote Similarity NPD6798 Discontinued
0.6538 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6538 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6534 Remote Similarity NPD7473 Discontinued
0.6533 Remote Similarity NPD3496 Discontinued
0.6529 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6527 Remote Similarity NPD3686 Approved
0.6527 Remote Similarity NPD3687 Approved
0.6524 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6519 Remote Similarity NPD1933 Approved
0.6513 Remote Similarity NPD2983 Phase 2
0.6513 Remote Similarity NPD2982 Phase 2
0.6513 Remote Similarity NPD7783 Phase 2
0.6513 Remote Similarity NPD7782 Clinical (unspecified phase)
0.651 Remote Similarity NPD7999 Approved
0.6509 Remote Similarity NPD6386 Approved
0.6509 Remote Similarity NPD6385 Approved
0.6505 Remote Similarity NPD6534 Approved
0.6505 Remote Similarity NPD6535 Approved
0.6503 Remote Similarity NPD4110 Phase 3
0.6503 Remote Similarity NPD6841 Approved
0.6503 Remote Similarity NPD6842 Approved
0.6503 Remote Similarity NPD6843 Phase 3
0.6503 Remote Similarity NPD3750 Approved
0.6503 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6503 Remote Similarity NPD4109 Clinical (unspecified phase)
0.65 Remote Similarity NPD5960 Phase 3
0.6497 Remote Similarity NPD6663 Approved
0.6497 Remote Similarity NPD7799 Discontinued
0.6492 Remote Similarity NPD7696 Phase 3
0.6492 Remote Similarity NPD7698 Approved
0.6492 Remote Similarity NPD7697 Approved
0.649 Remote Similarity NPD1610 Phase 2
0.649 Remote Similarity NPD3092 Approved
0.649 Remote Similarity NPD422 Phase 1
0.6485 Remote Similarity NPD4357 Discontinued
0.6481 Remote Similarity NPD2424 Discontinued
0.6478 Remote Similarity NPD2492 Phase 1
0.6474 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6801 Discontinued
0.6471 Remote Similarity NPD3225 Approved
0.6463 Remote Similarity NPD7157 Approved
0.6462 Remote Similarity NPD7874 Approved
0.6462 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6456 Remote Similarity NPD825 Approved
0.6456 Remote Similarity NPD1558 Phase 1
0.6456 Remote Similarity NPD826 Approved
0.6456 Remote Similarity NPD4140 Approved
0.6453 Remote Similarity NPD7768 Phase 2
0.6452 Remote Similarity NPD9494 Approved
0.6452 Remote Similarity NPD3018 Phase 2
0.6447 Remote Similarity NPD2981 Phase 2
0.6446 Remote Similarity NPD7422 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