Structure

Physi-Chem Properties

Molecular Weight:  680.23
Volume:  644.718
LogP:  1.098
LogD:  0.212
LogS:  -2.495
# Rotatable Bonds:  14
TPSA:  251.36
# H-Bond Aceptor:  16
# H-Bond Donor:  8
# Rings:  4
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.081
Synthetic Accessibility Score:  4.868
Fsp3:  0.5
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.559
MDCK Permeability:  3.676700725918636e-05
Pgp-inhibitor:  0.011
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.988
20% Bioavailability (F20%):  0.698
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.069
Plasma Protein Binding (PPB):  92.17647552490234%
Volume Distribution (VD):  0.337
Pgp-substrate:  10.463752746582031%

ADMET: Metabolism

CYP1A2-inhibitor:  0.055
CYP1A2-substrate:  0.021
CYP2C19-inhibitor:  0.104
CYP2C19-substrate:  0.053
CYP2C9-inhibitor:  0.189
CYP2C9-substrate:  0.171
CYP2D6-inhibitor:  0.076
CYP2D6-substrate:  0.142
CYP3A4-inhibitor:  0.13
CYP3A4-substrate:  0.026

ADMET: Excretion

Clearance (CL):  1.716
Half-life (T1/2):  0.894

ADMET: Toxicity

hERG Blockers:  0.205
Human Hepatotoxicity (H-HT):  0.179
Drug-inuced Liver Injury (DILI):  0.394
AMES Toxicity:  0.577
Rat Oral Acute Toxicity:  0.086
Maximum Recommended Daily Dose:  0.022
Skin Sensitization:  0.969
Carcinogencity:  0.104
Eye Corrosion:  0.003
Eye Irritation:  0.127
Respiratory Toxicity:  0.042

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

  Natural Product: NPC47471

Natural Product ID:  NPC47471
Common Name*:   Tubuloside B
IUPAC Name:   [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3-hydroxy-4-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methoxy]oxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  OSOFNYSIWGSNBA-BORBUMKPSA-N
Standard InCHI:  InChI=1S/C32H40O16/c1-15-26(39)29(42)27(40)23(46-15)14-45-30-28(41)24(13-44-25(38)8-5-17-3-6-19(34)21(36)11-17)48-32(31(30)47-16(2)33)43-10-9-18-4-7-20(35)22(37)12-18/h3-8,11-12,15,23-24,26-32,34-37,39-42H,9-10,13-14H2,1-2H3/b8-5+/t15-,23-,24+,26-,27-,28+,29+,30-,31+,32+/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@H](CO[C@H]2[C@@H]([C@@H](COC(=O)/C=C/c3ccc(c(c3)O)O)O[C@H]([C@@H]2OC(=O)C)OCCc2ccc(c(c2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL590315
PubChem CID:   46228758
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO6964 Cistanche tubulosa Species Orobanchaceae Eukaryota fresh stems n.a. n.a. PMID[20159656]
NPO10680 Cistanche deserticola Species Orobanchaceae Eukaryota n.a. n.a. n.a. PMID[25900014]
NPO6964 Cistanche tubulosa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10680 Cistanche deserticola Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6964 Cistanche tubulosa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10680 Cistanche deserticola Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10680 Cistanche deserticola Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10680 Cistanche deserticola Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6964 Cistanche tubulosa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10680 Cistanche deserticola Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6964 Cistanche tubulosa Species Orobanchaceae 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
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 8.6 % PMID[506319]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 33.6 % PMID[506319]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 75.4 % PMID[506319]
NPT993 Cell Line Hepatocyte Mus musculus IC50 = 14600.0 nM PMID[506319]
NPT1460 Cell Line L929 Mus musculus Inhibition = 10.7 % PMID[506319]
NPT1460 Cell Line L929 Mus musculus Inhibition = 13.4 % PMID[506319]
NPT1460 Cell Line L929 Mus musculus Inhibition = 36.4 % PMID[506319]
NPT1460 Cell Line L929 Mus musculus Inhibition = 39.2 % PMID[506319]

☑ 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 NPC47471 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 NPC476377
0.9925 High Similarity NPC475530
0.9925 High Similarity NPC473799
0.9852 High Similarity NPC476378
0.9852 High Similarity NPC247032
0.9852 High Similarity NPC269141
0.9852 High Similarity NPC205864
0.9852 High Similarity NPC476380
0.9852 High Similarity NPC476397
0.9852 High Similarity NPC476384
0.9852 High Similarity NPC476375
0.9852 High Similarity NPC476381
0.9852 High Similarity NPC175214
0.9852 High Similarity NPC119537
0.9852 High Similarity NPC264632
0.9852 High Similarity NPC96795
0.9852 High Similarity NPC76406
0.9852 High Similarity NPC112
0.9852 High Similarity NPC298257
0.9851 High Similarity NPC134405
0.9851 High Similarity NPC476385
0.985 High Similarity NPC68092
0.985 High Similarity NPC89105
0.985 High Similarity NPC197316
0.985 High Similarity NPC64141
0.985 High Similarity NPC205195
0.985 High Similarity NPC476383
0.985 High Similarity NPC81515
0.985 High Similarity NPC472350
0.9779 High Similarity NPC296954
0.9779 High Similarity NPC64195
0.9779 High Similarity NPC300894
0.9779 High Similarity NPC141455
0.9779 High Similarity NPC196063
0.9774 High Similarity NPC260425
0.9706 High Similarity NPC105005
0.9638 High Similarity NPC229505
0.9632 High Similarity NPC265648
0.9632 High Similarity NPC222433
0.9627 High Similarity NPC78363
0.9627 High Similarity NPC476376
0.9549 High Similarity NPC34293
0.9549 High Similarity NPC287597
0.9549 High Similarity NPC886
0.9433 High Similarity NPC259347
0.9433 High Similarity NPC476398
0.9433 High Similarity NPC94871
0.9433 High Similarity NPC470933
0.9433 High Similarity NPC476386
0.9433 High Similarity NPC473427
0.9433 High Similarity NPC306890
0.9433 High Similarity NPC471062
0.9424 High Similarity NPC252292
0.9424 High Similarity NPC34587
0.9424 High Similarity NPC100998
0.9424 High Similarity NPC34927
0.9424 High Similarity NPC476382
0.942 High Similarity NPC40305
0.9412 High Similarity NPC321184
0.9412 High Similarity NPC321638
0.9412 High Similarity NPC328273
0.9412 High Similarity NPC171134
0.9398 High Similarity NPC473285
0.9366 High Similarity NPC470934
0.9366 High Similarity NPC257970
0.9366 High Similarity NPC470927
0.9366 High Similarity NPC188393
0.9333 High Similarity NPC476870
0.9333 High Similarity NPC263829
0.9323 High Similarity NPC46137
0.9323 High Similarity NPC235294
0.9291 High Similarity NPC232992
0.9259 High Similarity NPC471883
0.9236 High Similarity NPC106818
0.922 High Similarity NPC476865
0.9214 High Similarity NPC476867
0.9209 High Similarity NPC140502
0.9179 High Similarity NPC225384
0.9179 High Similarity NPC138777
0.9179 High Similarity NPC246869
0.9173 High Similarity NPC477294
0.9173 High Similarity NPC229784
0.9173 High Similarity NPC477293
0.9172 High Similarity NPC87403
0.9149 High Similarity NPC287615
0.9149 High Similarity NPC476864
0.9149 High Similarity NPC476866
0.9149 High Similarity NPC476869
0.9149 High Similarity NPC476868
0.9149 High Similarity NPC83743
0.9149 High Similarity NPC262182
0.9149 High Similarity NPC216819
0.9111 High Similarity NPC254275
0.9098 High Similarity NPC232880
0.9091 High Similarity NPC300262
0.9091 High Similarity NPC201148
0.9091 High Similarity NPC23677
0.9091 High Similarity NPC210611
0.9091 High Similarity NPC215095
0.9091 High Similarity NPC199311
0.9091 High Similarity NPC261122
0.9091 High Similarity NPC3460
0.9091 High Similarity NPC28651
0.9091 High Similarity NPC80732
0.9091 High Similarity NPC192763
0.9044 High Similarity NPC254398
0.9041 High Similarity NPC471874
0.9037 High Similarity NPC219677
0.903 High Similarity NPC184092
0.9023 High Similarity NPC476873
0.9023 High Similarity NPC288416
0.9007 High Similarity NPC478239
0.9 High Similarity NPC186406
0.8973 High Similarity NPC478268
0.8971 High Similarity NPC473924
0.8966 High Similarity NPC476871
0.8958 High Similarity NPC28776
0.8958 High Similarity NPC473138
0.8947 High Similarity NPC471157
0.8944 High Similarity NPC110063
0.8936 High Similarity NPC296643
0.8936 High Similarity NPC157816
0.8905 High Similarity NPC28637
0.8904 High Similarity NPC7145
0.8904 High Similarity NPC125823
0.8904 High Similarity NPC85192
0.8904 High Similarity NPC143480
0.8897 High Similarity NPC106138
0.8897 High Similarity NPC283839
0.8897 High Similarity NPC478255
0.8897 High Similarity NPC90896
0.8881 High Similarity NPC108659
0.8881 High Similarity NPC264900
0.8881 High Similarity NPC106677
0.8881 High Similarity NPC79715
0.8881 High Similarity NPC231607
0.8873 High Similarity NPC278961
0.8873 High Similarity NPC113680
0.8872 High Similarity NPC126991
0.8872 High Similarity NPC83218
0.8849 High Similarity NPC157554
0.8844 High Similarity NPC472612
0.8844 High Similarity NPC289967
0.8844 High Similarity NPC472611
0.8836 High Similarity NPC69367
0.8819 High Similarity NPC199928
0.8815 High Similarity NPC225307
0.8811 High Similarity NPC232228
0.8811 High Similarity NPC292443
0.8806 High Similarity NPC94179
0.8803 High Similarity NPC473873
0.8803 High Similarity NPC473792
0.8794 High Similarity NPC202700
0.8777 High Similarity NPC123988
0.8767 High Similarity NPC478242
0.8741 High Similarity NPC471882
0.8741 High Similarity NPC103533
0.8741 High Similarity NPC173150
0.8741 High Similarity NPC45224
0.8741 High Similarity NPC471881
0.8741 High Similarity NPC35288
0.8741 High Similarity NPC156692
0.8733 High Similarity NPC11411
0.8723 High Similarity NPC100389
0.8723 High Similarity NPC220942
0.8723 High Similarity NPC226005
0.8714 High Similarity NPC199459
0.8714 High Similarity NPC177035
0.8714 High Similarity NPC470572
0.8714 High Similarity NPC52277
0.8705 High Similarity NPC135127
0.8705 High Similarity NPC35731
0.8676 High Similarity NPC148982
0.8667 High Similarity NPC61181
0.8667 High Similarity NPC131532
0.8662 High Similarity NPC106944
0.8652 High Similarity NPC84789
0.8652 High Similarity NPC138738
0.8652 High Similarity NPC65262
0.8652 High Similarity NPC126206
0.8652 High Similarity NPC310252
0.8652 High Similarity NPC302583
0.8652 High Similarity NPC470413
0.8652 High Similarity NPC100558
0.8652 High Similarity NPC101686
0.8652 High Similarity NPC469364
0.8647 High Similarity NPC52097
0.8627 High Similarity NPC7191
0.8627 High Similarity NPC149873
0.8621 High Similarity NPC143120
0.8621 High Similarity NPC274960
0.8621 High Similarity NPC473909
0.8618 High Similarity NPC478269
0.8611 High Similarity NPC204644
0.8591 High Similarity NPC176186
0.8591 High Similarity NPC53587
0.8591 High Similarity NPC169404
0.8582 High Similarity NPC471664
0.8582 High Similarity NPC37468
0.8582 High Similarity NPC154485

  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 NPC47471 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
0.985 High Similarity NPD7266 Discontinued
0.8146 Intermediate Similarity NPD1653 Approved
0.8108 Intermediate Similarity NPD6190 Approved
0.7927 Intermediate Similarity NPD7685 Pre-registration
0.7914 Intermediate Similarity NPD7472 Approved
0.7853 Intermediate Similarity NPD7054 Approved
0.7818 Intermediate Similarity NPD7251 Discontinued
0.7805 Intermediate Similarity NPD7074 Phase 3
0.7791 Intermediate Similarity NPD7228 Approved
0.7771 Intermediate Similarity NPD7808 Phase 3
0.7758 Intermediate Similarity NPD6797 Phase 2
0.7708 Intermediate Similarity NPD3027 Phase 3
0.7658 Intermediate Similarity NPD8455 Phase 2
0.7566 Intermediate Similarity NPD8166 Discontinued
0.7562 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD1613 Approved
0.7551 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD3818 Discontinued
0.7469 Intermediate Similarity NPD6234 Discontinued
0.744 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD8313 Approved
0.7412 Intermediate Similarity NPD8312 Approved
0.7407 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD7240 Approved
0.7386 Intermediate Similarity NPD6674 Discontinued
0.7383 Intermediate Similarity NPD230 Phase 1
0.7375 Intermediate Similarity NPD37 Approved
0.7346 Intermediate Similarity NPD4967 Phase 2
0.7346 Intermediate Similarity NPD4966 Approved
0.7346 Intermediate Similarity NPD4965 Approved
0.7321 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1091 Approved
0.7246 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD6166 Phase 2
0.7246 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD3022 Approved
0.7206 Intermediate Similarity NPD3021 Approved
0.72 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD6559 Discontinued
0.7171 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD1934 Approved
0.7153 Intermediate Similarity NPD3705 Approved
0.7119 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD4628 Phase 3
0.7081 Intermediate Similarity NPD3455 Phase 2
0.7066 Intermediate Similarity NPD8127 Discontinued
0.7066 Intermediate Similarity NPD7199 Phase 2
0.7063 Intermediate Similarity NPD1357 Approved
0.7059 Intermediate Similarity NPD7097 Phase 1
0.7037 Intermediate Similarity NPD4380 Phase 2
0.7032 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD5844 Phase 1
0.7014 Intermediate Similarity NPD5125 Phase 3
0.7014 Intermediate Similarity NPD5126 Approved
0.7012 Intermediate Similarity NPD1465 Phase 2
0.7011 Intermediate Similarity NPD7680 Approved
0.6988 Remote Similarity NPD7075 Discontinued
0.6978 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6978 Remote Similarity NPD228 Approved
0.6974 Remote Similarity NPD4060 Phase 1
0.697 Remote Similarity NPD3817 Phase 2
0.6943 Remote Similarity NPD1652 Phase 2
0.6928 Remote Similarity NPD4340 Discontinued
0.6923 Remote Similarity NPD5536 Phase 2
0.6918 Remote Similarity NPD5058 Phase 3
0.6909 Remote Similarity NPD2978 Approved
0.6909 Remote Similarity NPD2801 Approved
0.6909 Remote Similarity NPD2977 Approved
0.6908 Remote Similarity NPD6233 Phase 2
0.6887 Remote Similarity NPD7095 Approved
0.6882 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6875 Remote Similarity NPD9545 Approved
0.6867 Remote Similarity NPD5402 Approved
0.6867 Remote Similarity NPD2861 Phase 2
0.6857 Remote Similarity NPD969 Suspended
0.6848 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6842 Remote Similarity NPD3764 Approved
0.6826 Remote Similarity NPD3882 Suspended
0.6825 Remote Similarity NPD8151 Discontinued
0.6821 Remote Similarity NPD4908 Phase 1
0.6818 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6818 Remote Similarity NPD5124 Phase 1
0.6812 Remote Similarity NPD1358 Approved
0.6809 Remote Similarity NPD7843 Approved
0.6807 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6807 Remote Similarity NPD7819 Suspended
0.6798 Remote Similarity NPD8150 Discontinued
0.6791 Remote Similarity NPD8320 Phase 1
0.6791 Remote Similarity NPD8319 Approved
0.6774 Remote Similarity NPD6653 Approved
0.6774 Remote Similarity NPD5314 Approved
0.677 Remote Similarity NPD1511 Approved
0.6768 Remote Similarity NPD7458 Discontinued
0.6763 Remote Similarity NPD3751 Discontinued
0.6761 Remote Similarity NPD5283 Phase 1
0.6757 Remote Similarity NPD9269 Phase 2
0.6755 Remote Similarity NPD5736 Approved
0.6753 Remote Similarity NPD3061 Approved
0.6753 Remote Similarity NPD3062 Approved
0.6753 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6753 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6753 Remote Similarity NPD3620 Phase 2
0.6753 Remote Similarity NPD3059 Approved
0.6752 Remote Similarity NPD2935 Discontinued
0.6748 Remote Similarity NPD5403 Approved
0.6739 Remote Similarity NPD7699 Phase 2
0.6739 Remote Similarity NPD7700 Phase 2
0.6735 Remote Similarity NPD3496 Discontinued
0.6733 Remote Similarity NPD3094 Phase 2
0.6732 Remote Similarity NPD6798 Discontinued
0.6732 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6732 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6731 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6731 Remote Similarity NPD4538 Approved
0.6731 Remote Similarity NPD4536 Approved
0.673 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6728 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6728 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6725 Remote Similarity NPD6232 Discontinued
0.6711 Remote Similarity NPD2982 Phase 2
0.6711 Remote Similarity NPD2983 Phase 2
0.671 Remote Similarity NPD1933 Approved
0.671 Remote Similarity NPD6355 Discontinued
0.6709 Remote Similarity NPD5762 Approved
0.6709 Remote Similarity NPD5763 Approved
0.6707 Remote Similarity NPD3686 Approved
0.6707 Remote Similarity NPD3687 Approved
0.6705 Remote Similarity NPD7473 Discontinued
0.6689 Remote Similarity NPD422 Phase 1
0.6687 Remote Similarity NPD1512 Approved
0.6687 Remote Similarity NPD6385 Approved
0.6687 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6687 Remote Similarity NPD6386 Approved
0.6686 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6685 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9384 Approved
0.6667 Remote Similarity NPD6841 Approved
0.6667 Remote Similarity NPD6843 Phase 3
0.6667 Remote Similarity NPD9381 Approved
0.6667 Remote Similarity NPD7157 Approved
0.6667 Remote Similarity NPD7549 Discontinued
0.6667 Remote Similarity NPD6842 Approved
0.6649 Remote Similarity NPD7435 Discontinued
0.6647 Remote Similarity NPD6801 Discontinued
0.6646 Remote Similarity NPD9570 Approved
0.6645 Remote Similarity NPD825 Approved
0.6645 Remote Similarity NPD943 Approved
0.6645 Remote Similarity NPD3018 Phase 2
0.6645 Remote Similarity NPD9494 Approved
0.6645 Remote Similarity NPD1558 Phase 1
0.6645 Remote Similarity NPD826 Approved
0.6644 Remote Similarity NPD2981 Phase 2
0.6629 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6628 Remote Similarity NPD3787 Discontinued
0.6627 Remote Similarity NPD7768 Phase 2
0.6626 Remote Similarity NPD5401 Approved
0.6626 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6626 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6625 Remote Similarity NPD3060 Approved
0.6625 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6619 Remote Similarity NPD3134 Approved
0.6617 Remote Similarity NPD2933 Approved
0.6617 Remote Similarity NPD2934 Approved
0.661 Remote Similarity NPD7039 Approved
0.661 Remote Similarity NPD7038 Approved
0.6608 Remote Similarity NPD5494 Approved
0.66 Remote Similarity NPD9622 Approved
0.6587 Remote Similarity NPD7411 Suspended
0.6584 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6584 Remote Similarity NPD3750 Approved
0.6584 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6584 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6584 Remote Similarity NPD4110 Phase 3
0.6582 Remote Similarity NPD4108 Discontinued
0.6582 Remote Similarity NPD5588 Approved
0.6582 Remote Similarity NPD7033 Discontinued
0.6582 Remote Similarity NPD5960 Phase 3
0.6581 Remote Similarity NPD4062 Phase 3
0.6581 Remote Similarity NPD6663 Approved
0.658 Remote Similarity NPD7783 Phase 2
0.658 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6577 Remote Similarity NPD3092 Approved
0.6577 Remote Similarity NPD1610 Phase 2
0.6576 Remote Similarity NPD6535 Approved
0.6576 Remote Similarity NPD6534 Approved
0.6573 Remote Similarity NPD5535 Approved
0.6568 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6567 Remote Similarity NPD2859 Approved
0.6567 Remote Similarity NPD2860 Approved
0.6564 Remote Similarity NPD6799 Approved
0.6564 Remote Similarity NPD4357 Discontinued
0.6561 Remote Similarity NPD7698 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data