Structure

Physi-Chem Properties

Molecular Weight:  754.23
Volume:  703.044
LogP:  0.723
LogD:  0.197
LogS:  -2.715
# Rotatable Bonds:  17
TPSA:  279.05
# H-Bond Aceptor:  19
# H-Bond Donor:  8
# Rings:  4
# Heavy Atoms:  19

MedChem Properties

QED Drug-Likeness Score:  0.076
Synthetic Accessibility Score:  5.006
Fsp3:  0.471
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.643
MDCK Permeability:  5.58035280846525e-05
Pgp-inhibitor:  0.039
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.979
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.16
Plasma Protein Binding (PPB):  71.02275848388672%
Volume Distribution (VD):  0.376
Pgp-substrate:  27.47100067138672%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.804
CYP2C19-inhibitor:  0.015
CYP2C19-substrate:  0.47
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.145
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.225
CYP3A4-inhibitor:  0.058
CYP3A4-substrate:  0.117

ADMET: Excretion

Clearance (CL):  6.093
Half-life (T1/2):  0.958

ADMET: Toxicity

hERG Blockers:  0.386
Human Hepatotoxicity (H-HT):  0.593
Drug-inuced Liver Injury (DILI):  0.032
AMES Toxicity:  0.088
Rat Oral Acute Toxicity:  0.012
Maximum Recommended Daily Dose:  0.035
Skin Sensitization:  0.968
Carcinogencity:  0.047
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.026

Download Data

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

  Natural Product: NPC90896

Natural Product ID:  NPC90896
Common Name*:   (3-O-Sinapoyl)-Beta-D-Fructofuranosyl-(2->1)-(6-O-Sinapoyl)-Alpha-D-Glucopyranoside
IUPAC Name:   [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2S,3S,4R,5R)-4-hydroxy-3-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  FHIJMQWMMZEFBL-OPSYHMPNSA-N
Standard InCHI:  InChI=1S/C34H42O19/c1-45-18-9-16(10-19(46-2)26(18)39)5-7-24(37)49-14-23-28(41)30(43)31(44)33(50-23)53-34(15-36)32(29(42)22(13-35)52-34)51-25(38)8-6-17-11-20(47-3)27(40)21(12-17)48-4/h5-12,22-23,28-33,35-36,39-44H,13-15H2,1-4H3/b7-5+,8-6+/t22-,23-,28-,29-,30+,31-,32+,33-,34+/m1/s1
SMILES:  COc1cc(/C=C/C(=O)OC[C@H]2O[C@H](O[C@]3(CO)O[C@@H]([C@H]([C@@H]3OC(=O)/C=C/c3cc(OC)c(c(c3)OC)O)O)CO)[C@@H]([C@H]([C@@H]2O)O)O)cc(c1O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3581233
PubChem CID:   11968389
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
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota roots n.a. n.a. PMID[16989524]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. rhizome n.a. PMID[22863942]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota aerial parts n.a. n.a. PMID[24042007]
NPO7539 Raphanus sativus Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[24176362]
NPO7539 Raphanus sativus Species Brassicaceae Eukaryota seeds n.a. n.a. PMID[25466198]
NPO41013 Polygala flavescens ssp. flavescens Strain Polygalaceae Eukaryota n.a. n.a. n.a. PMID[28692289]
NPO7539 Raphanus sativus Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7539 Raphanus sativus Species Brassicaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO7539 Raphanus sativus Species Brassicaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO7539 Raphanus sativus Species Brassicaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO7539 Raphanus sativus Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21485 Polygala sibirica Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7539 Raphanus sativus Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21485 Polygala sibirica Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21485 Polygala sibirica Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7539 Raphanus sativus Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7539 Raphanus sativus Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21485 Polygala sibirica Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21485 Polygala sibirica Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27260 Polygala tenuifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7539 Raphanus sativus Species Brassicaceae 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
NPT34 Cell Line BV-2 Mus musculus IC50 = 37150.0 nM PMID[572126]
NPT81 Cell Line A549 Homo sapiens IC50 = 21050.0 nM PMID[572126]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 = 16690.0 nM PMID[572126]
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 = 14150.0 nM PMID[572126]
NPT148 Cell Line HCT-15 Homo sapiens IC50 = 17200.0 nM PMID[572126]
NPT644 Individual Protein L-lactate dehydrogenase A chain Homo sapiens IC50 = 90400.0 nM PMID[572127]
NPT35 Others n.a. IC50 = 29.63 ug.mL-1 PMID[572126]

☑ 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 NPC90896 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 NPC283839
0.9792 High Similarity NPC472612
0.9792 High Similarity NPC289967
0.9792 High Similarity NPC472611
0.9716 High Similarity NPC287615
0.9716 High Similarity NPC83743
0.9716 High Similarity NPC262182
0.9716 High Similarity NPC216819
0.9645 High Similarity NPC297342
0.9514 High Similarity NPC28651
0.9514 High Similarity NPC80732
0.9514 High Similarity NPC300262
0.9514 High Similarity NPC215095
0.9514 High Similarity NPC192763
0.9514 High Similarity NPC210611
0.9514 High Similarity NPC261122
0.9514 High Similarity NPC199311
0.9514 High Similarity NPC3460
0.9514 High Similarity NPC201148
0.9507 High Similarity NPC110063
0.9448 High Similarity NPC106138
0.9384 High Similarity NPC188393
0.9384 High Similarity NPC470934
0.9379 High Similarity NPC478237
0.932 High Similarity NPC7145
0.932 High Similarity NPC85192
0.932 High Similarity NPC143480
0.932 High Similarity NPC125823
0.9291 High Similarity NPC226005
0.9241 High Similarity NPC476865
0.9231 High Similarity NPC157816
0.9231 High Similarity NPC140502
0.9184 High Similarity NPC471062
0.9184 High Similarity NPC473427
0.9184 High Similarity NPC476398
0.9184 High Similarity NPC306890
0.9184 High Similarity NPC259347
0.9184 High Similarity NPC476386
0.9184 High Similarity NPC94871
0.9184 High Similarity NPC470933
0.9172 High Similarity NPC34587
0.9172 High Similarity NPC476868
0.9172 High Similarity NPC476869
0.9172 High Similarity NPC34927
0.9172 High Similarity NPC476864
0.9172 High Similarity NPC100998
0.9172 High Similarity NPC476866
0.9172 High Similarity NPC476382
0.9172 High Similarity NPC252292
0.9167 High Similarity NPC478239
0.9149 High Similarity NPC157554
0.9128 High Similarity NPC478268
0.9122 High Similarity NPC257970
0.9122 High Similarity NPC470927
0.911 High Similarity NPC199928
0.9103 High Similarity NPC476867
0.9085 High Similarity NPC195196
0.9048 High Similarity NPC232992
0.9038 High Similarity NPC59516
0.9028 High Similarity NPC186406
0.9021 High Similarity NPC98777
0.9021 High Similarity NPC212770
0.9021 High Similarity NPC100389
0.9007 High Similarity NPC471883
0.8993 High Similarity NPC476871
0.8986 High Similarity NPC93924
0.8986 High Similarity NPC252402
0.8986 High Similarity NPC102934
0.8973 High Similarity NPC300894
0.8973 High Similarity NPC292443
0.8973 High Similarity NPC187774
0.8973 High Similarity NPC196063
0.8973 High Similarity NPC472713
0.8973 High Similarity NPC296954
0.8973 High Similarity NPC472712
0.8973 High Similarity NPC118385
0.8973 High Similarity NPC141455
0.8973 High Similarity NPC473046
0.8973 High Similarity NPC232228
0.8966 High Similarity NPC469559
0.8958 High Similarity NPC202700
0.8951 High Similarity NPC124149
0.8951 High Similarity NPC59324
0.8951 High Similarity NPC65530
0.894 High Similarity NPC150442
0.8936 High Similarity NPC132895
0.8933 High Similarity NPC213197
0.8919 High Similarity NPC41844
0.8919 High Similarity NPC39657
0.8904 High Similarity NPC40305
0.8904 High Similarity NPC105005
0.8897 High Similarity NPC47471
0.8897 High Similarity NPC134405
0.8897 High Similarity NPC476385
0.8897 High Similarity NPC476377
0.8889 High Similarity NPC328273
0.8889 High Similarity NPC321638
0.8889 High Similarity NPC321184
0.8889 High Similarity NPC11411
0.8889 High Similarity NPC171134
0.8881 High Similarity NPC37468
0.8881 High Similarity NPC203230
0.8881 High Similarity NPC186418
0.8881 High Similarity NPC242028
0.8874 High Similarity NPC176186
0.8874 High Similarity NPC169404
0.8874 High Similarity NPC53587
0.8851 High Similarity NPC212890
0.8851 High Similarity NPC229505
0.8836 High Similarity NPC189115
0.8836 High Similarity NPC5262
0.8836 High Similarity NPC472714
0.8836 High Similarity NPC475084
0.8831 High Similarity NPC472860
0.8828 High Similarity NPC210478
0.8828 High Similarity NPC473799
0.8828 High Similarity NPC475530
0.8816 High Similarity NPC246893
0.8811 High Similarity NPC476870
0.8811 High Similarity NPC185778
0.8803 High Similarity NPC254398
0.88 High Similarity NPC286235
0.88 High Similarity NPC206264
0.88 High Similarity NPC51328
0.88 High Similarity NPC212670
0.88 High Similarity NPC55158
0.88 High Similarity NPC475250
0.88 High Similarity NPC313334
0.88 High Similarity NPC478242
0.8794 High Similarity NPC219677
0.8784 High Similarity NPC475096
0.8784 High Similarity NPC477702
0.8782 High Similarity NPC149873
0.8782 High Similarity NPC7191
0.8776 High Similarity NPC76406
0.8776 High Similarity NPC112
0.8776 High Similarity NPC476380
0.8776 High Similarity NPC476375
0.8776 High Similarity NPC269141
0.8776 High Similarity NPC476397
0.8776 High Similarity NPC264632
0.8776 High Similarity NPC476378
0.8776 High Similarity NPC476381
0.8776 High Similarity NPC175214
0.8776 High Similarity NPC205864
0.8776 High Similarity NPC298257
0.8776 High Similarity NPC96795
0.8776 High Similarity NPC247032
0.8776 High Similarity NPC119537
0.8776 High Similarity NPC476384
0.8774 High Similarity NPC173726
0.8774 High Similarity NPC215400
0.8774 High Similarity NPC241600
0.8774 High Similarity NPC160780
0.8774 High Similarity NPC478269
0.8774 High Similarity NPC230531
0.8774 High Similarity NPC289811
0.8767 High Similarity NPC469661
0.8767 High Similarity NPC472711
0.8766 High Similarity NPC478266
0.8759 High Similarity NPC64141
0.8759 High Similarity NPC197316
0.8759 High Similarity NPC472350
0.8759 High Similarity NPC68092
0.8759 High Similarity NPC89105
0.8759 High Similarity NPC476383
0.8759 High Similarity NPC205195
0.8759 High Similarity NPC81515
0.875 High Similarity NPC302610
0.875 High Similarity NPC215060
0.875 High Similarity NPC52277
0.875 High Similarity NPC199459
0.875 High Similarity NPC177035
0.875 High Similarity NPC164857
0.875 High Similarity NPC476352
0.8741 High Similarity NPC135127
0.8741 High Similarity NPC886
0.8741 High Similarity NPC34293
0.8741 High Similarity NPC107478
0.8741 High Similarity NPC287597
0.8733 High Similarity NPC96294
0.8733 High Similarity NPC248132
0.8733 High Similarity NPC187398
0.8733 High Similarity NPC476348
0.8733 High Similarity NPC130449
0.8732 High Similarity NPC470270
0.8732 High Similarity NPC473924
0.8732 High Similarity NPC473285
0.8732 High Similarity NPC252833
0.8726 High Similarity NPC246024
0.8718 High Similarity NPC239966
0.8718 High Similarity NPC203020
0.8718 High Similarity NPC478265
0.8716 High Similarity NPC25292
0.8716 High Similarity NPC64195
0.8716 High Similarity NPC473045
0.871 High Similarity NPC226759
0.871 High Similarity NPC475592
0.871 High Similarity NPC1913
0.8707 High Similarity NPC265648

  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 NPC90896 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
0.88 High Similarity NPD1653 Approved
0.8759 High Similarity NPD7266 Discontinued
0.8282 Intermediate Similarity NPD7228 Approved
0.8264 Intermediate Similarity NPD3027 Phase 3
0.8187 Intermediate Similarity NPD6234 Discontinued
0.8182 Intermediate Similarity NPD7472 Approved
0.8171 Intermediate Similarity NPD3818 Discontinued
0.8121 Intermediate Similarity NPD7054 Approved
0.8101 Intermediate Similarity NPD37 Approved
0.8084 Intermediate Similarity NPD7685 Pre-registration
0.8072 Intermediate Similarity NPD7074 Phase 3
0.8063 Intermediate Similarity NPD4967 Phase 2
0.8063 Intermediate Similarity NPD4965 Approved
0.8063 Intermediate Similarity NPD4966 Approved
0.8036 Intermediate Similarity NPD7808 Phase 3
0.7976 Intermediate Similarity NPD7251 Discontinued
0.7973 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7973 Intermediate Similarity NPD1613 Approved
0.7929 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD6797 Phase 2
0.7898 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD7240 Approved
0.784 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD6559 Discontinued
0.7758 Intermediate Similarity NPD7199 Phase 2
0.7724 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7703 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6190 Approved
0.7683 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD1934 Approved
0.7635 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD1357 Approved
0.7602 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6166 Phase 2
0.7515 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD3882 Suspended
0.75 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD2982 Phase 2
0.7483 Intermediate Similarity NPD2983 Phase 2
0.7466 Intermediate Similarity NPD1091 Approved
0.7466 Intermediate Similarity NPD3705 Approved
0.7455 Intermediate Similarity NPD3817 Phase 2
0.7451 Intermediate Similarity NPD230 Phase 1
0.7446 Intermediate Similarity NPD7680 Approved
0.7418 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD2981 Phase 2
0.7394 Intermediate Similarity NPD2801 Approved
0.7394 Intermediate Similarity NPD8455 Phase 2
0.7384 Intermediate Similarity NPD5844 Phase 1
0.7375 Intermediate Similarity NPD4357 Discontinued
0.7365 Intermediate Similarity NPD7075 Discontinued
0.7342 Intermediate Similarity NPD6674 Discontinued
0.7342 Intermediate Similarity NPD1652 Phase 2
0.733 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD4380 Phase 2
0.7289 Intermediate Similarity NPD1465 Phase 2
0.7285 Intermediate Similarity NPD3018 Phase 2
0.7241 Intermediate Similarity NPD5536 Phase 2
0.7193 Intermediate Similarity NPD6232 Discontinued
0.7186 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD2977 Approved
0.7186 Intermediate Similarity NPD7819 Suspended
0.7186 Intermediate Similarity NPD2978 Approved
0.7182 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD8313 Approved
0.7175 Intermediate Similarity NPD8312 Approved
0.7168 Intermediate Similarity NPD7473 Discontinued
0.7167 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD1511 Approved
0.7143 Intermediate Similarity NPD5402 Approved
0.7143 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD8127 Discontinued
0.7124 Intermediate Similarity NPD4908 Phase 1
0.7115 Intermediate Similarity NPD5124 Phase 1
0.7115 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD422 Phase 1
0.7111 Intermediate Similarity NPD6843 Phase 3
0.7111 Intermediate Similarity NPD6842 Approved
0.7111 Intermediate Similarity NPD6841 Approved
0.7099 Intermediate Similarity NPD5058 Phase 3
0.7081 Intermediate Similarity NPD4628 Phase 3
0.7076 Intermediate Similarity NPD5494 Approved
0.7073 Intermediate Similarity NPD1512 Approved
0.7063 Intermediate Similarity NPD228 Approved
0.7041 Intermediate Similarity NPD5353 Approved
0.7032 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD5403 Approved
0.7024 Intermediate Similarity NPD6801 Discontinued
0.7022 Intermediate Similarity NPD7549 Discontinued
0.7021 Intermediate Similarity NPD1358 Approved
0.7006 Intermediate Similarity NPD1933 Approved
0.7 Intermediate Similarity NPD1610 Phase 2
0.6979 Remote Similarity NPD8151 Discontinued
0.6975 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6975 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6959 Remote Similarity NPD1548 Phase 1
0.6951 Remote Similarity NPD6799 Approved
0.6951 Remote Similarity NPD5297 Approved
0.6948 Remote Similarity NPD9494 Approved
0.6948 Remote Similarity NPD2861 Phase 2
0.6943 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6943 Remote Similarity NPD3620 Phase 2
0.6943 Remote Similarity NPD4060 Phase 1
0.6941 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6932 Remote Similarity NPD3751 Discontinued
0.6918 Remote Similarity NPD7097 Phase 1
0.6909 Remote Similarity NPD5401 Approved
0.6901 Remote Similarity NPD7768 Phase 2
0.6899 Remote Similarity NPD4340 Discontinued
0.6879 Remote Similarity NPD6233 Phase 2
0.6871 Remote Similarity NPD8166 Discontinued
0.6871 Remote Similarity NPD3750 Approved
0.6864 Remote Similarity NPD7411 Suspended
0.6859 Remote Similarity NPD7095 Approved
0.6855 Remote Similarity NPD2492 Phase 1
0.6855 Remote Similarity NPD6653 Approved
0.6852 Remote Similarity NPD1549 Phase 2
0.6849 Remote Similarity NPD5283 Phase 1
0.6845 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6842 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6832 Remote Similarity NPD2935 Discontinued
0.6832 Remote Similarity NPD1551 Phase 2
0.6831 Remote Similarity NPD3134 Approved
0.6824 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6815 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6813 Remote Similarity NPD4978 Clinical (unspecified phase)
0.681 Remote Similarity NPD4237 Approved
0.681 Remote Similarity NPD4236 Phase 3
0.6805 Remote Similarity NPD4675 Approved
0.6805 Remote Similarity NPD4678 Approved
0.68 Remote Similarity NPD3787 Discontinued
0.6792 Remote Similarity NPD6355 Discontinued
0.6792 Remote Similarity NPD447 Suspended
0.679 Remote Similarity NPD1550 Clinical (unspecified phase)
0.679 Remote Similarity NPD5763 Approved
0.679 Remote Similarity NPD3540 Phase 1
0.679 Remote Similarity NPD1552 Clinical (unspecified phase)
0.679 Remote Similarity NPD5762 Approved
0.6786 Remote Similarity NPD3687 Approved
0.6786 Remote Similarity NPD3686 Approved
0.6784 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6781 Remote Similarity NPD7843 Approved
0.6776 Remote Similarity NPD8434 Phase 2
0.677 Remote Similarity NPD5588 Approved
0.677 Remote Similarity NPD1510 Phase 2
0.6768 Remote Similarity NPD4110 Phase 3
0.6768 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6766 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6766 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6765 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6765 Remote Similarity NPD6386 Approved
0.6765 Remote Similarity NPD6385 Approved
0.6761 Remote Similarity NPD5242 Approved
0.6755 Remote Similarity NPD5126 Approved
0.6755 Remote Similarity NPD5125 Phase 3
0.6752 Remote Similarity NPD4625 Phase 3
0.6748 Remote Similarity NPD970 Clinical (unspecified phase)
0.6732 Remote Similarity NPD9269 Phase 2
0.673 Remote Similarity NPD1558 Phase 1
0.6728 Remote Similarity NPD3539 Phase 1
0.6727 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6727 Remote Similarity NPD2219 Phase 1
0.6724 Remote Similarity NPD919 Approved
0.6723 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6719 Remote Similarity NPD7435 Discontinued
0.6712 Remote Similarity NPD969 Suspended
0.6711 Remote Similarity NPD3496 Discontinued
0.6709 Remote Similarity NPD6798 Discontinued
0.6708 Remote Similarity NPD4536 Approved
0.6708 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6708 Remote Similarity NPD4538 Approved
0.6707 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6707 Remote Similarity NPD3060 Approved
0.6707 Remote Similarity NPD2534 Approved
0.6707 Remote Similarity NPD2532 Approved
0.6707 Remote Similarity NPD2533 Approved
0.6707 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6707 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6706 Remote Similarity NPD6599 Discontinued
0.6706 Remote Similarity NPD7028 Phase 2
0.6688 Remote Similarity NPD4749 Approved
0.6686 Remote Similarity NPD5677 Discontinued
0.6685 Remote Similarity NPD7039 Approved
0.6685 Remote Similarity NPD7038 Approved
0.6667 Remote Similarity NPD6971 Discontinued
0.6667 Remote Similarity NPD7033 Discontinued
0.6667 Remote Similarity NPD7585 Approved
0.6647 Remote Similarity NPD4005 Discontinued
0.6647 Remote Similarity NPD3455 Phase 2
0.6647 Remote Similarity NPD7458 Discontinued
0.6646 Remote Similarity NPD2424 Discontinued
0.6645 Remote Similarity NPD3225 Approved
0.6644 Remote Similarity NPD7157 Approved
0.6626 Remote Similarity NPD3454 Phase 3

  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