Structure

Physi-Chem Properties

Molecular Weight:  584.23
Volume:  580.834
LogP:  1.543
LogD:  2.208
LogS:  -3.826
# Rotatable Bonds:  13
TPSA:  156.53
# H-Bond Aceptor:  11
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.201
Synthetic Accessibility Score:  4.226
Fsp3:  0.355
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:  -5.181
MDCK Permeability:  1.4691240721731447e-05
Pgp-inhibitor:  0.989
Pgp-substrate:  0.684
Human Intestinal Absorption (HIA):  0.532
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.397
Plasma Protein Binding (PPB):  70.7594223022461%
Volume Distribution (VD):  0.615
Pgp-substrate:  24.23896598815918%

ADMET: Metabolism

CYP1A2-inhibitor:  0.009
CYP1A2-substrate:  0.275
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.874
CYP2C9-inhibitor:  0.034
CYP2C9-substrate:  0.752
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.601
CYP3A4-inhibitor:  0.659
CYP3A4-substrate:  0.931

ADMET: Excretion

Clearance (CL):  6.798
Half-life (T1/2):  0.576

ADMET: Toxicity

hERG Blockers:  0.108
Human Hepatotoxicity (H-HT):  0.138
Drug-inuced Liver Injury (DILI):  0.421
AMES Toxicity:  0.07
Rat Oral Acute Toxicity:  0.374
Maximum Recommended Daily Dose:  0.514
Skin Sensitization:  0.359
Carcinogencity:  0.046
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.01

Download Data

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

  Natural Product: NPC260397

Natural Product ID:  NPC260397
Common Name*:   Threo-Buddlenol B
IUPAC Name:   1-(4-hydroxy-3-methoxyphenyl)-2-[4-[3-(hydroxymethyl)-5-[(E)-3-hydroxyprop-1-enyl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenoxy]propane-1,3-diol
Synonyms:   Threo-Buddlenol B
Standard InCHIKey:  LCXGTSCVCJANHX-AATRIKPKSA-N
Standard InCHI:  InChI=1S/C31H36O11/c1-37-23-12-18(7-8-22(23)35)28(36)27(16-34)41-31-25(39-3)13-19(14-26(31)40-4)29-21(15-33)20-10-17(6-5-9-32)11-24(38-2)30(20)42-29/h5-8,10-14,21,27-29,32-36H,9,15-16H2,1-4H3/b6-5+
SMILES:  COc1cc(ccc1O)C(C(CO)Oc1c(cc(cc1OC)C1C(CO)c2cc(/C=C/CO)cc(c2O1)OC)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1761831
PubChem CID:   21627696
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0014-5793(03)00033-4]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1021/ac991142i]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1034/j.1399-3054.2003.00030.x]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1074/jbc.274.1.397]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1074/jbc.M302362200]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1074/jbc.M314195200]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1074/jbc.M411109200]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1104/pp.103.022368]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. leaf n.a. PMID[10952545]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[10952545]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[11005203]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[12637544]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[12805618]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[14745019]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[15280363]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[15820655]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[15834012]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota aerial parts n.a. n.a. PMID[15844959]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[1684022]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[17611796]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[18057039]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[18235971]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[18318836]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. leaf n.a. PMID[19521717]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[21193570]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[21194489]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[21395888]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota leaves and twigs n.a. n.a. PMID[21435874]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[21800258]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[23370715]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[23950498]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. root n.a. PMID[24163311]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[24285094]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. root n.a. PMID[25457500]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[27128895]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. root n.a. PMID[27363486]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[27432888]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota Resinous Wood n.a. n.a. PMID[29227647]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[8278506]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. root n.a. Database[MetaboLights]
NPO19866 Arabidopsis thaliana Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14558 Aquilaria sinensis Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19866 Arabidopsis thaliana 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
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 21300.0 nM PMID[447992]

☑ 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 NPC260397 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
0.9784 High Similarity NPC181615
0.9714 High Similarity NPC317053
0.9714 High Similarity NPC324492
0.9645 High Similarity NPC320671
0.9645 High Similarity NPC328567
0.9645 High Similarity NPC327412
0.9645 High Similarity NPC320970
0.9638 High Similarity NPC263261
0.9638 High Similarity NPC87725
0.9571 High Similarity NPC470097
0.9571 High Similarity NPC471415
0.9571 High Similarity NPC114119
0.9565 High Similarity NPC291101
0.9565 High Similarity NPC266197
0.9517 High Similarity NPC470769
0.9444 High Similarity NPC477612
0.9441 High Similarity NPC20757
0.9441 High Similarity NPC227516
0.9433 High Similarity NPC63879
0.9433 High Similarity NPC93323
0.9433 High Similarity NPC280092
0.9433 High Similarity NPC45257
0.9433 High Similarity NPC12641
0.9424 High Similarity NPC184797
0.9424 High Similarity NPC309124
0.942 High Similarity NPC477938
0.9379 High Similarity NPC329343
0.9379 High Similarity NPC324517
0.9379 High Similarity NPC321972
0.9375 High Similarity NPC211561
0.9362 High Similarity NPC47633
0.9362 High Similarity NPC102044
0.9362 High Similarity NPC85264
0.9357 High Similarity NPC178054
0.9357 High Similarity NPC311530
0.9353 High Similarity NPC260741
0.9353 High Similarity NPC70682
0.9353 High Similarity NPC236306
0.9353 High Similarity NPC473739
0.9353 High Similarity NPC22517
0.9353 High Similarity NPC232164
0.9348 High Similarity NPC263367
0.9348 High Similarity NPC477939
0.9348 High Similarity NPC29799
0.9348 High Similarity NPC54743
0.9348 High Similarity NPC156502
0.9348 High Similarity NPC77861
0.9348 High Similarity NPC177160
0.9348 High Similarity NPC209985
0.9348 High Similarity NPC10737
0.931 High Similarity NPC472710
0.931 High Similarity NPC472709
0.9291 High Similarity NPC107161
0.9286 High Similarity NPC254759
0.9286 High Similarity NPC160283
0.9262 High Similarity NPC470827
0.9241 High Similarity NPC473266
0.9241 High Similarity NPC470826
0.9241 High Similarity NPC470098
0.9236 High Similarity NPC101376
0.9236 High Similarity NPC263940
0.9236 High Similarity NPC262911
0.9236 High Similarity NPC294558
0.9236 High Similarity NPC236202
0.9236 High Similarity NPC170103
0.9236 High Similarity NPC70409
0.9236 High Similarity NPC204770
0.9236 High Similarity NPC108811
0.9236 High Similarity NPC202742
0.9236 High Similarity NPC18185
0.9236 High Similarity NPC21776
0.9236 High Similarity NPC58190
0.9236 High Similarity NPC16269
0.9236 High Similarity NPC82917
0.9225 High Similarity NPC477616
0.922 High Similarity NPC247291
0.922 High Similarity NPC35216
0.922 High Similarity NPC471389
0.9214 High Similarity NPC292882
0.9209 High Similarity NPC16435
0.9209 High Similarity NPC306441
0.9209 High Similarity NPC470802
0.9209 High Similarity NPC248727
0.9209 High Similarity NPC265433
0.9209 High Similarity NPC162659
0.9209 High Similarity NPC270456
0.9203 High Similarity NPC187616
0.9203 High Similarity NPC287745
0.9203 High Similarity NPC326095
0.9203 High Similarity NPC244983
0.9203 High Similarity NPC49603
0.9203 High Similarity NPC193026
0.92 High Similarity NPC470828
0.9189 High Similarity NPC157333
0.9172 High Similarity NPC473408
0.9172 High Similarity NPC329836
0.9172 High Similarity NPC270751
0.9167 High Similarity NPC96576
0.9161 High Similarity NPC304894
0.9161 High Similarity NPC473108
0.9161 High Similarity NPC50250
0.9161 High Similarity NPC15659
0.9155 High Similarity NPC59841
0.9155 High Similarity NPC2613
0.9155 High Similarity NPC475891
0.9155 High Similarity NPC204347
0.9149 High Similarity NPC22317
0.9149 High Similarity NPC27495
0.9149 High Similarity NPC259519
0.9137 High Similarity NPC234333
0.9137 High Similarity NPC112939
0.9137 High Similarity NPC260898
0.9137 High Similarity NPC47398
0.9137 High Similarity NPC474206
0.9137 High Similarity NPC470356
0.9137 High Similarity NPC94750
0.9137 High Similarity NPC121812
0.9137 High Similarity NPC61946
0.9137 High Similarity NPC473413
0.9137 High Similarity NPC93783
0.9137 High Similarity NPC112246
0.9137 High Similarity NPC256262
0.9133 High Similarity NPC125495
0.913 High Similarity NPC26394
0.913 High Similarity NPC475840
0.913 High Similarity NPC158331
0.9116 High Similarity NPC2745
0.9103 High Similarity NPC39657
0.9103 High Similarity NPC114505
0.9103 High Similarity NPC15956
0.9103 High Similarity NPC31325
0.9103 High Similarity NPC193473
0.9103 High Similarity NPC213074
0.9103 High Similarity NPC275284
0.9103 High Similarity NPC224674
0.9097 High Similarity NPC469557
0.9091 High Similarity NPC474104
0.9091 High Similarity NPC173203
0.9091 High Similarity NPC163508
0.9091 High Similarity NPC469630
0.9085 High Similarity NPC470372
0.9085 High Similarity NPC471414
0.9078 High Similarity NPC25966
0.9078 High Similarity NPC471388
0.9078 High Similarity NPC230124
0.9078 High Similarity NPC32630
0.9078 High Similarity NPC319647
0.9078 High Similarity NPC6300
0.9078 High Similarity NPC127218
0.9078 High Similarity NPC184613
0.9078 High Similarity NPC245207
0.9078 High Similarity NPC114171
0.9071 High Similarity NPC472334
0.9071 High Similarity NPC227503
0.9071 High Similarity NPC474639
0.9071 High Similarity NPC302701
0.9071 High Similarity NPC230734
0.9071 High Similarity NPC269091
0.9071 High Similarity NPC472336
0.9065 High Similarity NPC317380
0.9065 High Similarity NPC170694
0.9065 High Similarity NPC478085
0.9058 High Similarity NPC160991
0.9058 High Similarity NPC7903
0.9058 High Similarity NPC175067
0.9058 High Similarity NPC184447
0.9058 High Similarity NPC470752
0.9058 High Similarity NPC35932
0.9058 High Similarity NPC16208
0.9058 High Similarity NPC204215
0.9058 High Similarity NPC230219
0.9054 High Similarity NPC160196
0.9054 High Similarity NPC279406
0.9054 High Similarity NPC226809
0.9054 High Similarity NPC157783
0.9048 High Similarity NPC195561
0.9048 High Similarity NPC158784
0.9041 High Similarity NPC473876
0.9034 High Similarity NPC112251
0.9028 High Similarity NPC171932
0.9028 High Similarity NPC28440
0.9021 High Similarity NPC131971
0.9021 High Similarity NPC41782
0.9021 High Similarity NPC253878
0.9014 High Similarity NPC55793
0.9007 High Similarity NPC474390
0.9007 High Similarity NPC103976
0.9007 High Similarity NPC102904
0.9007 High Similarity NPC176051
0.9007 High Similarity NPC276490
0.9007 High Similarity NPC107551
0.9007 High Similarity NPC474282
0.9007 High Similarity NPC211549
0.9007 High Similarity NPC326797
0.9 High Similarity NPC151224
0.9 High Similarity NPC126409
0.9 High Similarity NPC472337
0.9 High Similarity NPC24490
0.9 High Similarity NPC202104
0.9 High Similarity NPC165155

  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 NPC260397 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
0.8921 High Similarity NPD1612 Clinical (unspecified phase)
0.8921 High Similarity NPD1613 Approved
0.8841 High Similarity NPD3027 Phase 3
0.8643 High Similarity NPD4907 Clinical (unspecified phase)
0.8633 High Similarity NPD1529 Clinical (unspecified phase)
0.8561 High Similarity NPD1530 Clinical (unspecified phase)
0.85 High Similarity NPD4908 Phase 1
0.8228 Intermediate Similarity NPD6234 Discontinued
0.8141 Intermediate Similarity NPD37 Approved
0.8129 Intermediate Similarity NPD1610 Phase 2
0.8125 Intermediate Similarity NPD7199 Phase 2
0.8101 Intermediate Similarity NPD4966 Approved
0.8101 Intermediate Similarity NPD4967 Phase 2
0.8101 Intermediate Similarity NPD4965 Approved
0.8098 Intermediate Similarity NPD7228 Approved
0.8089 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8086 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8086 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8086 Intermediate Similarity NPD6166 Phase 2
0.8067 Intermediate Similarity NPD6674 Discontinued
0.8042 Intermediate Similarity NPD2861 Phase 2
0.8025 Intermediate Similarity NPD1934 Approved
0.8 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD4625 Phase 3
0.7914 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7891 Intermediate Similarity NPD3620 Phase 2
0.7891 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD1653 Approved
0.7879 Intermediate Similarity NPD3818 Discontinued
0.7842 Intermediate Similarity NPD1548 Phase 1
0.7831 Intermediate Similarity NPD5844 Phase 1
0.7829 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7793 Intermediate Similarity NPD3018 Phase 2
0.7784 Intermediate Similarity NPD7074 Phase 3
0.777 Intermediate Similarity NPD4060 Phase 1
0.7764 Intermediate Similarity NPD3882 Suspended
0.7762 Intermediate Similarity NPD4749 Approved
0.775 Intermediate Similarity NPD2801 Approved
0.773 Intermediate Similarity NPD5494 Approved
0.7725 Intermediate Similarity NPD7054 Approved
0.7711 Intermediate Similarity NPD7473 Discontinued
0.7708 Intermediate Similarity NPD8651 Approved
0.7702 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD7472 Approved
0.7639 Intermediate Similarity NPD2982 Phase 2
0.7639 Intermediate Similarity NPD2983 Phase 2
0.7636 Intermediate Similarity NPD6232 Discontinued
0.7609 Intermediate Similarity NPD5283 Phase 1
0.7603 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD5735 Approved
0.7593 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD7240 Approved
0.7588 Intermediate Similarity NPD6559 Discontinued
0.7569 Intermediate Similarity NPD2981 Phase 2
0.7566 Intermediate Similarity NPD5588 Approved
0.7562 Intermediate Similarity NPD4380 Phase 2
0.753 Intermediate Similarity NPD7229 Phase 3
0.7529 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD1511 Approved
0.75 Intermediate Similarity NPD7157 Approved
0.75 Intermediate Similarity NPD4536 Approved
0.75 Intermediate Similarity NPD7075 Discontinued
0.75 Intermediate Similarity NPD4538 Approved
0.75 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD3817 Phase 2
0.7485 Intermediate Similarity NPD7251 Discontinued
0.7483 Intermediate Similarity NPD5124 Phase 1
0.7483 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD7447 Phase 1
0.7468 Intermediate Similarity NPD7266 Discontinued
0.7468 Intermediate Similarity NPD5762 Approved
0.7468 Intermediate Similarity NPD5763 Approved
0.7464 Intermediate Similarity NPD228 Approved
0.7452 Intermediate Similarity NPD5058 Phase 3
0.7442 Intermediate Similarity NPD7808 Phase 3
0.7436 Intermediate Similarity NPD7466 Approved
0.7436 Intermediate Similarity NPD6331 Phase 2
0.7429 Intermediate Similarity NPD7906 Approved
0.7427 Intermediate Similarity NPD6797 Phase 2
0.7423 Intermediate Similarity NPD8455 Phase 2
0.7421 Intermediate Similarity NPD1512 Approved
0.7414 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD7843 Approved
0.7405 Intermediate Similarity NPD7212 Phase 2
0.7405 Intermediate Similarity NPD7213 Phase 3
0.74 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD1091 Approved
0.7379 Intermediate Similarity NPD3705 Approved
0.7371 Intermediate Similarity NPD4663 Approved
0.7368 Intermediate Similarity NPD6355 Discontinued
0.7365 Intermediate Similarity NPD8127 Discontinued
0.7365 Intermediate Similarity NPD6959 Discontinued
0.7358 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD8054 Approved
0.7356 Intermediate Similarity NPD8053 Approved
0.7347 Intermediate Similarity NPD6696 Suspended
0.7341 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD7549 Discontinued
0.7338 Intermediate Similarity NPD5960 Phase 3
0.7337 Intermediate Similarity NPD2489 Approved
0.7337 Intermediate Similarity NPD27 Approved
0.7333 Intermediate Similarity NPD7768 Phase 2
0.7325 Intermediate Similarity NPD3892 Phase 2
0.7321 Intermediate Similarity NPD3051 Approved
0.7319 Intermediate Similarity NPD3022 Approved
0.7319 Intermediate Similarity NPD3021 Approved
0.7317 Intermediate Similarity NPD1465 Phase 2
0.7317 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD7819 Suspended
0.731 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD1558 Phase 1
0.7301 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD4578 Approved
0.7299 Intermediate Similarity NPD4577 Approved
0.7299 Intermediate Similarity NPD7312 Approved
0.7299 Intermediate Similarity NPD7313 Approved
0.7299 Intermediate Similarity NPD7311 Approved
0.7299 Intermediate Similarity NPD7310 Approved
0.7296 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD6100 Approved
0.729 Intermediate Similarity NPD6099 Approved
0.7289 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD6798 Discontinued
0.7283 Intermediate Similarity NPD7680 Approved
0.7279 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD5327 Phase 3
0.7278 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD2969 Approved
0.7278 Intermediate Similarity NPD2970 Approved
0.7267 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD1652 Phase 2
0.7261 Intermediate Similarity NPD5177 Phase 3
0.7257 Intermediate Similarity NPD7309 Approved
0.7257 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD6801 Discontinued
0.7254 Intermediate Similarity NPD6671 Approved
0.7253 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD6584 Phase 3
0.7246 Intermediate Similarity NPD2684 Approved
0.7244 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD3540 Phase 1
0.7241 Intermediate Similarity NPD5846 Approved
0.7241 Intermediate Similarity NPD6516 Phase 2
0.7239 Intermediate Similarity NPD4678 Approved
0.7239 Intermediate Similarity NPD4675 Approved
0.7219 Intermediate Similarity NPD7095 Approved
0.7215 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD2424 Discontinued
0.7195 Intermediate Similarity NPD7411 Suspended
0.719 Intermediate Similarity NPD4140 Approved
0.7188 Intermediate Similarity NPD7041 Phase 2
0.7188 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD3094 Phase 2
0.7179 Intermediate Similarity NPD3539 Phase 1
0.7178 Intermediate Similarity NPD4005 Discontinued
0.7174 Intermediate Similarity NPD290 Approved
0.7172 Intermediate Similarity NPD1357 Approved
0.717 Intermediate Similarity NPD6190 Approved
0.717 Intermediate Similarity NPD2677 Approved
0.7169 Intermediate Similarity NPD2560 Approved
0.7169 Intermediate Similarity NPD2563 Approved
0.7161 Intermediate Similarity NPD7097 Phase 1
0.7152 Intermediate Similarity NPD4236 Phase 3
0.7152 Intermediate Similarity NPD4237 Approved
0.7143 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD422 Phase 1
0.7134 Intermediate Similarity NPD6002 Phase 3
0.7134 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD6004 Phase 3
0.7134 Intermediate Similarity NPD6005 Phase 3
0.7134 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD7124 Phase 2
0.7124 Intermediate Similarity NPD6233 Phase 2
0.7118 Intermediate Similarity NPD6071 Discontinued
0.7115 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD4110 Phase 3
0.7107 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4097 Suspended
0.7097 Intermediate Similarity NPD6353 Approved
0.7097 Intermediate Similarity NPD6653 Approved
0.7095 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD6072 Discontinued
0.7089 Intermediate Similarity NPD7037 Approved
0.7089 Intermediate Similarity NPD1549 Phase 2
0.7078 Intermediate Similarity NPD2238 Phase 2
0.7078 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD3926 Phase 2
0.7066 Intermediate Similarity NPD5402 Approved
0.7047 Intermediate Similarity NPD6582 Phase 2

  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