Structure

Physi-Chem Properties

Molecular Weight:  506.22
Volume:  496.11
LogP:  1.689
LogD:  1.433
LogS:  -2.87
# Rotatable Bonds:  7
TPSA:  158.3
# H-Bond Aceptor:  10
# H-Bond Donor:  6
# Rings:  4
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.318
Synthetic Accessibility Score:  4.426
Fsp3:  0.538
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:  -6.215
MDCK Permeability:  8.538117981515825e-06
Pgp-inhibitor:  0.006
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.605
20% Bioavailability (F20%):  0.256
30% Bioavailability (F30%):  0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.039
Plasma Protein Binding (PPB):  96.0399169921875%
Volume Distribution (VD):  0.507
Pgp-substrate:  7.371337890625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.026
CYP1A2-substrate:  0.463
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.738
CYP2C9-inhibitor:  0.031
CYP2C9-substrate:  0.59
CYP2D6-inhibitor:  0.026
CYP2D6-substrate:  0.288
CYP3A4-inhibitor:  0.099
CYP3A4-substrate:  0.563

ADMET: Excretion

Clearance (CL):  9.206
Half-life (T1/2):  0.672

ADMET: Toxicity

hERG Blockers:  0.157
Human Hepatotoxicity (H-HT):  0.306
Drug-inuced Liver Injury (DILI):  0.766
AMES Toxicity:  0.307
Rat Oral Acute Toxicity:  0.102
Maximum Recommended Daily Dose:  0.848
Skin Sensitization:  0.63
Carcinogencity:  0.048
Eye Corrosion:  0.003
Eye Irritation:  0.181
Respiratory Toxicity:  0.662

Download Data

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

  Natural Product: NPC286245

Natural Product ID:  NPC286245
Common Name*:   Aviculin
IUPAC Name:   (2R,3R,4R,5R,6S)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-6-methyloxane-3,4,5-triol
Synonyms:   Aviculin
Standard InCHIKey:  FPJFPMQEUVMUKU-CDDCGRQRSA-N
Standard InCHI:  InChI=1S/C26H34O10/c1-12-23(30)24(31)25(32)26(36-12)35-11-17-15(10-27)6-14-8-21(34-3)19(29)9-16(14)22(17)13-4-5-18(28)20(7-13)33-2/h4-5,7-9,12,15,17,22-32H,6,10-11H2,1-3H3/t12-,15-,17-,22-,23-,24+,25+,26+/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@H]2[C@@H](Cc3cc(c(cc3[C@@H]2c2ccc(c(c2)OC)O)O)OC)CO)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2332673
PubChem CID:   10391477
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001511] Lignan glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO3057 Polygonum aviculare Species Polygonaceae Eukaryota n.a. whole plant n.a. DOI[10.1016/S1572-557X(05)02007-6]
NPO1276 Thonningia sanguinea Species Balanophoraceae Eukaryota n.a. n.a. n.a. PMID[10843586]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. Okinawan n.a. PMID[11076554]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[14600382]
NPO11304 Vitis thunbergii Species Vitaceae Eukaryota Roots n.a. n.a. PMID[15730246]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. red sea n.a. PMID[16180827]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. Red Sea n.a. PMID[17190441]
NPO27826 Sinularia maxima Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[23200246]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. PMID[23540981]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota Twigs n.a. n.a. PMID[25894905]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota Twigs n.a. n.a. PMID[28358502]
NPO1276 Thonningia sanguinea Species Balanophoraceae Eukaryota Subaerial Parts n.a. n.a. PMID[30207720]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. n.a. n.a. PMID[3572416]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. n.a. n.a. PMID[8778242]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. n.a. n.a. PMID[9461648]
NPO3057 Polygonum aviculare Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6084 Scurrura atropurpurea n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO27754 Rubia oncotricha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3057 Polygonum aviculare Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6084 Scurrura atropurpurea n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO3057 Polygonum aviculare Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27754 Rubia oncotricha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3057 Polygonum aviculare Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3057 Polygonum aviculare Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2201 Orthocaulis attenuatus Species Anastrophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28104 Streptomyces hachijoensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25532 Blitum virgatum Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26828 Barbarea verna Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26327 Chaenomeles sinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8519 Garcinia andamanica Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11941 Helleborus serbicus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28212 Ilex purpurea Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14372 Melochia tomentosa Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10086 Scrophularia scorodonia Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11304 Vitis thunbergii Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9038 Aconitum burnatii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25482 Phyllogeiton zeyheri n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4980 Lycopodium erythraeum Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27754 Rubia oncotricha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12049 Lecania gerlachei Species Ramalinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28173 Boronia coerulescens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18828 Iryanthera coriacea Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28155 Perezia carpholepis Species Pereziidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27826 Sinularia maxima Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28329 Cereus candicans Species Sagartiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23780 Psoroma crassum Species Pannariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16596 Dysoxylum schiffneri Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1276 Thonningia sanguinea Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5239 Hyrtios erecta Species Thorectidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10313 Plantago arborescens Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6028 Laurencia pinnatifida Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20597 Phascolion strombus Species Phascolionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26183 Scabiosa pyrenaica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3112 Honorius nutans Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5899 Ainsliaea uniflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28387 Acanthophyllum elatius Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO222 Phebalium drummondii Species Rutaceae 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
NPT113 Cell Line RAW264.7 Mus musculus Activity = 112.41 % PMID[504102]
NPT113 Cell Line RAW264.7 Mus musculus Activity = 39.68 % PMID[504102]
NPT76 Cell Line C6 Rattus norvegicus Activity = 123.06 % PMID[504103]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 > 10000.0 nM PMID[504103]
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[504103]
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 > 10000.0 nM PMID[504103]
NPT148 Cell Line HCT-15 Homo sapiens IC50 > 10000.0 nM PMID[504103]
NPT1 Others Radical scavenging activity ED50 = 44.8 uM PMID[504102]
NPT27 Others Unspecified Activity = 96.1 % PMID[504103]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 40200.0 nM PMID[504103]

☑ 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 NPC286245 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 NPC272619
0.9927 High Similarity NPC253015
0.9927 High Similarity NPC471065
0.9716 High Similarity NPC44452
0.951 High Similarity NPC225815
0.951 High Similarity NPC214326
0.951 High Similarity NPC9933
0.951 High Similarity NPC145979
0.951 High Similarity NPC185955
0.951 High Similarity NPC469707
0.951 High Similarity NPC182368
0.951 High Similarity NPC469706
0.951 High Similarity NPC260781
0.951 High Similarity NPC218041
0.9429 High Similarity NPC113680
0.9429 High Similarity NPC278961
0.9424 High Similarity NPC472711
0.9416 High Similarity NPC52277
0.9416 High Similarity NPC177035
0.9416 High Similarity NPC199459
0.9357 High Similarity NPC48309
0.9291 High Similarity NPC477898
0.9291 High Similarity NPC470950
0.9291 High Similarity NPC185307
0.9247 High Similarity NPC21902
0.9241 High Similarity NPC183380
0.9225 High Similarity NPC129417
0.9225 High Similarity NPC84181
0.9225 High Similarity NPC283995
0.9225 High Similarity NPC470235
0.922 High Similarity NPC476356
0.922 High Similarity NPC5262
0.922 High Similarity NPC472714
0.9214 High Similarity NPC106944
0.9209 High Similarity NPC138738
0.9209 High Similarity NPC304152
0.9209 High Similarity NPC470413
0.9167 High Similarity NPC275284
0.9167 High Similarity NPC114505
0.9167 High Similarity NPC31325
0.9167 High Similarity NPC15956
0.9167 High Similarity NPC213074
0.9167 High Similarity NPC224674
0.9167 High Similarity NPC193473
0.9161 High Similarity NPC279298
0.9161 High Similarity NPC22150
0.9161 High Similarity NPC38041
0.9155 High Similarity NPC46092
0.913 High Similarity NPC35731
0.9097 High Similarity NPC112861
0.9091 High Similarity NPC133251
0.9091 High Similarity NPC164183
0.9091 High Similarity NPC473046
0.9091 High Similarity NPC118385
0.9091 High Similarity NPC472712
0.9091 High Similarity NPC472713
0.9091 High Similarity NPC187774
0.9085 High Similarity NPC60249
0.9065 High Similarity NPC101624
0.9065 High Similarity NPC184938
0.9054 High Similarity NPC106669
0.9054 High Similarity NPC475227
0.9054 High Similarity NPC200645
0.9051 High Similarity NPC248307
0.9051 High Similarity NPC65942
0.9034 High Similarity NPC39657
0.9028 High Similarity NPC43508
0.9028 High Similarity NPC18979
0.9028 High Similarity NPC476301
0.9014 High Similarity NPC76871
0.9007 High Similarity NPC156376
0.8993 High Similarity NPC471942
0.8993 High Similarity NPC311256
0.8993 High Similarity NPC476411
0.8993 High Similarity NPC187194
0.8986 High Similarity NPC478268
0.8986 High Similarity NPC474442
0.8986 High Similarity NPC254275
0.898 High Similarity NPC475224
0.898 High Similarity NPC98624
0.8973 High Similarity NPC179809
0.8958 High Similarity NPC471667
0.8958 High Similarity NPC79429
0.8958 High Similarity NPC473045
0.8958 High Similarity NPC217635
0.8958 High Similarity NPC471063
0.8958 High Similarity NPC25292
0.8951 High Similarity NPC246947
0.8951 High Similarity NPC189115
0.8951 High Similarity NPC469559
0.8912 High Similarity NPC220006
0.8912 High Similarity NPC181452
0.8912 High Similarity NPC55158
0.8912 High Similarity NPC51328
0.8912 High Similarity NPC286235
0.8912 High Similarity NPC474893
0.8912 High Similarity NPC475940
0.8905 High Similarity NPC307110
0.8897 High Similarity NPC100998
0.8897 High Similarity NPC475096
0.8897 High Similarity NPC34587
0.8897 High Similarity NPC476382
0.8897 High Similarity NPC34927
0.8897 High Similarity NPC252292
0.8889 High Similarity NPC473044
0.8881 High Similarity NPC471908
0.8881 High Similarity NPC469661
0.8857 High Similarity NPC470881
0.8851 High Similarity NPC472710
0.8851 High Similarity NPC472709
0.8849 High Similarity NPC106739
0.8849 High Similarity NPC471505
0.8849 High Similarity NPC227002
0.8844 High Similarity NPC130959
0.8844 High Similarity NPC304048
0.8844 High Similarity NPC474834
0.8844 High Similarity NPC290902
0.8844 High Similarity NPC159697
0.8844 High Similarity NPC248132
0.8844 High Similarity NPC474795
0.8844 High Similarity NPC117788
0.8844 High Similarity NPC226153
0.8844 High Similarity NPC130449
0.8844 High Similarity NPC291326
0.8844 High Similarity NPC303013
0.8844 High Similarity NPC474856
0.8844 High Similarity NPC474940
0.8836 High Similarity NPC276753
0.8836 High Similarity NPC190714
0.8836 High Similarity NPC125755
0.8836 High Similarity NPC99515
0.8836 High Similarity NPC205796
0.8832 High Similarity NPC307050
0.8832 High Similarity NPC474178
0.8832 High Similarity NPC252307
0.8832 High Similarity NPC245826
0.8832 High Similarity NPC277458
0.8819 High Similarity NPC253878
0.8819 High Similarity NPC140502
0.8819 High Similarity NPC302506
0.88 High Similarity NPC78809
0.8794 High Similarity NPC135777
0.8794 High Similarity NPC142547
0.8786 High Similarity NPC6836
0.8777 High Similarity NPC476345
0.8776 High Similarity NPC232992
0.8776 High Similarity NPC227902
0.8768 High Similarity NPC184092
0.8767 High Similarity NPC469586
0.8767 High Similarity NPC277867
0.8767 High Similarity NPC161700
0.8759 High Similarity NPC108659
0.8759 High Similarity NPC265154
0.8759 High Similarity NPC264900
0.8759 High Similarity NPC118533
0.8759 High Similarity NPC231607
0.8759 High Similarity NPC79715
0.8759 High Similarity NPC165045
0.8758 High Similarity NPC478269
0.875 High Similarity NPC471414
0.875 High Similarity NPC11411
0.8741 High Similarity NPC123526
0.8741 High Similarity NPC88640
0.8741 High Similarity NPC114171
0.8741 High Similarity NPC193666
0.8741 High Similarity NPC212770
0.8741 High Similarity NPC6300
0.8741 High Similarity NPC98777
0.8741 High Similarity NPC230124
0.8741 High Similarity NPC184613
0.8732 High Similarity NPC77861
0.8725 High Similarity NPC24425
0.8723 High Similarity NPC107478
0.8716 High Similarity NPC175976
0.8716 High Similarity NPC270751
0.8716 High Similarity NPC116229
0.8714 High Similarity NPC252833
0.8707 High Similarity NPC241846
0.8707 High Similarity NPC93610
0.8705 High Similarity NPC77040
0.8705 High Similarity NPC242807
0.8705 High Similarity NPC241522
0.8705 High Similarity NPC42300
0.8705 High Similarity NPC145305
0.8705 High Similarity NPC173308
0.8705 High Similarity NPC92164
0.8705 High Similarity NPC472024
0.8705 High Similarity NPC257582
0.8705 High Similarity NPC187998
0.8705 High Similarity NPC64201
0.8705 High Similarity NPC181079
0.8705 High Similarity NPC153739
0.8705 High Similarity NPC80600
0.8705 High Similarity NPC174495
0.8705 High Similarity NPC275950
0.8701 High Similarity NPC100936
0.8701 High Similarity NPC1253
0.8699 High Similarity NPC138227
0.8699 High Similarity NPC168579
0.8699 High Similarity NPC179521

  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 NPC286245 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
0.8881 High Similarity NPD6674 Discontinued
0.8608 High Similarity NPD7228 Approved
0.8483 Intermediate Similarity NPD7266 Discontinued
0.8397 Intermediate Similarity NPD6234 Discontinued
0.8369 Intermediate Similarity NPD3027 Phase 3
0.8312 Intermediate Similarity NPD37 Approved
0.8269 Intermediate Similarity NPD4966 Approved
0.8269 Intermediate Similarity NPD4967 Phase 2
0.8269 Intermediate Similarity NPD4965 Approved
0.8194 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.8194 Intermediate Similarity NPD3620 Phase 2
0.8069 Intermediate Similarity NPD1613 Approved
0.8069 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD7240 Approved
0.8058 Intermediate Similarity NPD3705 Approved
0.787 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7831 Intermediate Similarity NPD7074 Phase 3
0.7821 Intermediate Similarity NPD1653 Approved
0.7793 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD7054 Approved
0.7763 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD7685 Pre-registration
0.773 Intermediate Similarity NPD7199 Phase 2
0.7725 Intermediate Similarity NPD7472 Approved
0.7724 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD8455 Phase 2
0.7687 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD1091 Approved
0.7671 Intermediate Similarity NPD4908 Phase 1
0.7664 Intermediate Similarity NPD5283 Phase 1
0.766 Intermediate Similarity NPD5125 Phase 3
0.766 Intermediate Similarity NPD5126 Approved
0.7651 Intermediate Similarity NPD5735 Approved
0.7616 Intermediate Similarity NPD4108 Discontinued
0.7611 Intermediate Similarity NPD7680 Approved
0.7603 Intermediate Similarity NPD2861 Phase 2
0.7589 Intermediate Similarity NPD1357 Approved
0.7584 Intermediate Similarity NPD4060 Phase 1
0.7564 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD8312 Approved
0.7544 Intermediate Similarity NPD8313 Approved
0.753 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD7251 Discontinued
0.7529 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD228 Approved
0.75 Intermediate Similarity NPD3818 Discontinued
0.75 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5058 Phase 3
0.7485 Intermediate Similarity NPD7808 Phase 3
0.7471 Intermediate Similarity NPD6797 Phase 2
0.7466 Intermediate Similarity NPD3094 Phase 2
0.7456 Intermediate Similarity NPD5844 Phase 1
0.7434 Intermediate Similarity NPD7097 Phase 1
0.741 Intermediate Similarity NPD8127 Discontinued
0.7405 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD5762 Approved
0.7403 Intermediate Similarity NPD5763 Approved
0.7403 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD4625 Phase 3
0.7381 Intermediate Similarity NPD6166 Phase 2
0.7381 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD3021 Approved
0.7372 Intermediate Similarity NPD3022 Approved
0.7362 Intermediate Similarity NPD2978 Approved
0.7362 Intermediate Similarity NPD2977 Approved
0.7351 Intermediate Similarity NPD4140 Approved
0.7345 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7473 Discontinued
0.7333 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD5327 Phase 3
0.7329 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD4538 Approved
0.732 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD4536 Approved
0.731 Intermediate Similarity NPD1610 Phase 2
0.731 Intermediate Similarity NPD3092 Approved
0.7305 Intermediate Similarity NPD7157 Approved
0.7303 Intermediate Similarity NPD3657 Discovery
0.7301 Intermediate Similarity NPD1934 Approved
0.7278 Intermediate Similarity NPD2489 Approved
0.7278 Intermediate Similarity NPD27 Approved
0.7273 Intermediate Similarity NPD7906 Approved
0.7262 Intermediate Similarity NPD6232 Discontinued
0.7262 Intermediate Similarity NPD3051 Approved
0.7261 Intermediate Similarity NPD8166 Discontinued
0.7256 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7312 Approved
0.7241 Intermediate Similarity NPD7311 Approved
0.7241 Intermediate Similarity NPD7310 Approved
0.7241 Intermediate Similarity NPD7313 Approved
0.7233 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD7041 Phase 2
0.7229 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD6559 Discontinued
0.7219 Intermediate Similarity NPD2969 Approved
0.7219 Intermediate Similarity NPD2970 Approved
0.7216 Intermediate Similarity NPD4663 Approved
0.7215 Intermediate Similarity NPD6190 Approved
0.7214 Intermediate Similarity NPD7843 Approved
0.7211 Intermediate Similarity NPD2983 Phase 2
0.7211 Intermediate Similarity NPD2982 Phase 2
0.72 Intermediate Similarity NPD7309 Approved
0.7195 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD7028 Phase 2
0.7162 Intermediate Similarity NPD8651 Approved
0.7161 Intermediate Similarity NPD5588 Approved
0.7161 Intermediate Similarity NPD5960 Phase 3
0.716 Intermediate Similarity NPD3787 Discontinued
0.7153 Intermediate Similarity NPD3091 Approved
0.7152 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7095 Approved
0.7143 Intermediate Similarity NPD4578 Approved
0.7143 Intermediate Similarity NPD2981 Phase 2
0.7143 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6353 Approved
0.7143 Intermediate Similarity NPD4577 Approved
0.7133 Intermediate Similarity NPD3018 Phase 2
0.7126 Intermediate Similarity NPD7833 Phase 2
0.7126 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7831 Phase 2
0.7124 Intermediate Similarity NPD1558 Phase 1
0.7115 Intermediate Similarity NPD2438 Suspended
0.7107 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD5241 Discontinued
0.7099 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD4749 Approved
0.7089 Intermediate Similarity NPD3060 Approved
0.7089 Intermediate Similarity NPD5177 Phase 3
0.7081 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD4380 Phase 2
0.707 Intermediate Similarity NPD1375 Discontinued
0.7067 Intermediate Similarity NPD4624 Approved
0.7063 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD2684 Approved
0.7048 Intermediate Similarity NPD1465 Phase 2
0.7044 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD4628 Phase 3
0.7044 Intermediate Similarity NPD6331 Phase 2
0.7044 Intermediate Similarity NPD4110 Phase 3
0.7025 Intermediate Similarity NPD7037 Approved
0.702 Intermediate Similarity NPD5736 Approved
0.7013 Intermediate Similarity NPD2238 Phase 2
0.7012 Intermediate Similarity NPD7458 Discontinued
0.7012 Intermediate Similarity NPD4005 Discontinued
0.7 Intermediate Similarity NPD2677 Approved
0.6994 Remote Similarity NPD3751 Discontinued
0.6993 Remote Similarity NPD5111 Phase 2
0.6993 Remote Similarity NPD5110 Phase 2
0.6993 Remote Similarity NPD5109 Approved
0.6989 Remote Similarity NPD6823 Phase 2
0.6983 Remote Similarity NPD6842 Approved
0.6983 Remote Similarity NPD6841 Approved
0.6983 Remote Similarity NPD6843 Phase 3
0.6981 Remote Similarity NPD4236 Phase 3
0.6981 Remote Similarity NPD4237 Approved
0.6973 Remote Similarity NPD6778 Approved
0.6973 Remote Similarity NPD6776 Approved
0.6973 Remote Similarity NPD6779 Approved
0.6973 Remote Similarity NPD6780 Approved
0.6973 Remote Similarity NPD6782 Approved
0.6973 Remote Similarity NPD6781 Approved
0.6973 Remote Similarity NPD6777 Approved
0.6971 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6355 Discontinued
0.6954 Remote Similarity NPD6584 Phase 3
0.6952 Remote Similarity NPD7435 Discontinued
0.6948 Remote Similarity NPD6233 Phase 2
0.6946 Remote Similarity NPD2801 Approved
0.6944 Remote Similarity NPD6671 Approved
0.6943 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6943 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6939 Remote Similarity NPD5846 Approved
0.6939 Remote Similarity NPD3095 Discontinued
0.6939 Remote Similarity NPD4626 Approved
0.6939 Remote Similarity NPD6516 Phase 2
0.6937 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6933 Remote Similarity NPD1283 Approved
0.6933 Remote Similarity NPD6273 Approved
0.6933 Remote Similarity NPD6696 Suspended
0.6923 Remote Similarity NPD4097 Suspended
0.6923 Remote Similarity NPD6653 Approved
0.6918 Remote Similarity NPD1548 Phase 1
0.691 Remote Similarity NPD8053 Approved
0.691 Remote Similarity NPD8054 Approved
0.6909 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6905 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6903 Remote Similarity NPD2979 Phase 3
0.6901 Remote Similarity NPD6959 Discontinued
0.6894 Remote Similarity NPD5307 Clinical (unspecified phase)
0.689 Remote Similarity NPD4727 Phase 1
0.6889 Remote Similarity NPD7243 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