Structure

Physi-Chem Properties

Molecular Weight:  722.15
Volume:  672.464
LogP:  3.646
LogD:  0.983
LogS:  -4.591
# Rotatable Bonds:  6
TPSA:  290.43
# H-Bond Aceptor:  17
# H-Bond Donor:  10
# Rings:  6
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.077
Synthetic Accessibility Score:  5.145
Fsp3:  0.229
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.895
MDCK Permeability:  6.324863079498755e-06
Pgp-inhibitor:  0.288
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.983
20% Bioavailability (F20%):  0.662
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  97.8274917602539%
Volume Distribution (VD):  0.381
Pgp-substrate:  5.025646209716797%

ADMET: Metabolism

CYP1A2-inhibitor:  0.484
CYP1A2-substrate:  0.015
CYP2C19-inhibitor:  0.083
CYP2C19-substrate:  0.036
CYP2C9-inhibitor:  0.563
CYP2C9-substrate:  0.067
CYP2D6-inhibitor:  0.176
CYP2D6-substrate:  0.114
CYP3A4-inhibitor:  0.073
CYP3A4-substrate:  0.026

ADMET: Excretion

Clearance (CL):  6.887
Half-life (T1/2):  0.933

ADMET: Toxicity

hERG Blockers:  0.103
Human Hepatotoxicity (H-HT):  0.162
Drug-inuced Liver Injury (DILI):  0.99
AMES Toxicity:  0.717
Rat Oral Acute Toxicity:  0.003
Maximum Recommended Daily Dose:  0.025
Skin Sensitization:  0.96
Carcinogencity:  0.043
Eye Corrosion:  0.003
Eye Irritation:  0.893
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: NPC231254

Natural Product ID:  NPC231254
Common Name*:   Thonningianin B
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  UJNCWORGHSATHA-XWSAIMBSSA-N
Standard InCHI:  InChI=1S/C35H30O17/c36-17(7-6-13-4-2-1-3-5-13)25-18(37)8-14(9-19(25)38)50-35-31(46)30(45)32-22(51-35)12-49-33(47)15-10-20(39)26(41)28(43)23(15)24-16(34(48)52-32)11-21(40)27(42)29(24)44/h1-5,8-11,22,30-32,35,37-46H,6-7,12H2/t22-,30-,31-,32-,35-/m1/s1
SMILES:  O[C@H]1[C@H](Oc2cc(O)c(c(c2)O)C(=O)CCc2ccccc2)O[C@H]2[C@H]([C@@H]1O)OC(=O)c1cc(O)c(c(c1c1c(C(=O)OC2)cc(c(c1O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL509123
PubChem CID:   10101397
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000238] Tannins
        • [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO1276 Thonningia sanguinea Species Balanophoraceae Eukaryota n.a. n.a. n.a. PMID[10843586]
NPO7630 Cyperus longus Species Cyperaceae Eukaryota n.a. Egyptian herbal medicine n.a. PMID[15104485]
NPO1276 Thonningia sanguinea Species Balanophoraceae Eukaryota Subaerial Parts n.a. n.a. PMID[30207720]
NPO1276 Thonningia sanguinea Species Balanophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18040 Huberantha nitidissima Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8626 Rhizophora stylosa Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14636 Piper betel Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10115 Merendera caucasica Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7630 Cyperus longus Species Cyperaceae 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
NPT5224 Individual Protein NS3 Hepatitis C virus IC50 = 800.0 nM PMID[507665]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Activity = 28.5 % PMID[507667]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 21700.0 nM PMID[507667]
NPT35 Others n.a. IC50 = 21000.0 nM PMID[507666]
NPT35 Others n.a. Activity = 90.0 % PMID[507666]

☑ 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 NPC231254 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
0.9882 High Similarity NPC65489
0.9711 High Similarity NPC264302
0.9708 High Similarity NPC111490
0.9708 High Similarity NPC261623
0.9593 High Similarity NPC469650
0.9588 High Similarity NPC80956
0.954 High Similarity NPC93065
0.954 High Similarity NPC472720
0.954 High Similarity NPC469652
0.954 High Similarity NPC472724
0.954 High Similarity NPC472721
0.954 High Similarity NPC31208
0.954 High Similarity NPC160543
0.9538 High Similarity NPC260521
0.9538 High Similarity NPC469649
0.9532 High Similarity NPC8940
0.9483 High Similarity NPC290289
0.9483 High Similarity NPC477081
0.9483 High Similarity NPC477083
0.9483 High Similarity NPC240200
0.9483 High Similarity NPC223534
0.9483 High Similarity NPC158214
0.9477 High Similarity NPC97119
0.9477 High Similarity NPC135831
0.9477 High Similarity NPC297503
0.9471 High Similarity NPC472723
0.9429 High Similarity NPC201814
0.9429 High Similarity NPC187632
0.9425 High Similarity NPC105591
0.9408 High Similarity NPC67134
0.9408 High Similarity NPC47140
0.9375 High Similarity NPC40078
0.9375 High Similarity NPC471091
0.9375 High Similarity NPC97924
0.9364 High Similarity NPC132111
0.936 High Similarity NPC471030
0.9357 High Similarity NPC297574
0.9353 High Similarity NPC172033
0.9353 High Similarity NPC88560
0.9353 High Similarity NPC175230
0.9349 High Similarity NPC204937
0.9349 High Similarity NPC149011
0.9345 High Similarity NPC470271
0.9345 High Similarity NPC311389
0.9314 High Similarity NPC179947
0.9306 High Similarity NPC469371
0.9302 High Similarity NPC476618
0.9302 High Similarity NPC476622
0.9302 High Similarity NPC113836
0.9302 High Similarity NPC37668
0.9302 High Similarity NPC476620
0.9302 High Similarity NPC476623
0.9302 High Similarity NPC253521
0.9302 High Similarity NPC476619
0.9302 High Similarity NPC476621
0.9286 High Similarity NPC175793
0.9274 High Similarity NPC3474
0.927 High Similarity NPC477082
0.9261 High Similarity NPC119094
0.9261 High Similarity NPC173872
0.9261 High Similarity NPC473618
0.9257 High Similarity NPC104910
0.9257 High Similarity NPC474093
0.9253 High Similarity NPC123259
0.9253 High Similarity NPC129533
0.9244 High Similarity NPC144097
0.9244 High Similarity NPC61904
0.9244 High Similarity NPC472991
0.9244 High Similarity NPC472992
0.924 High Similarity NPC472993
0.9235 High Similarity NPC470272
0.9231 High Similarity NPC261411
0.9231 High Similarity NPC43918
0.9231 High Similarity NPC190204
0.9205 High Similarity NPC30011
0.9205 High Similarity NPC72554
0.9205 High Similarity NPC97817
0.9205 High Similarity NPC475179
0.92 High Similarity NPC318119
0.9195 High Similarity NPC53680
0.9195 High Similarity NPC208797
0.9191 High Similarity NPC267680
0.9191 High Similarity NPC267549
0.9191 High Similarity NPC196127
0.9191 High Similarity NPC35167
0.9191 High Similarity NPC217387
0.9191 High Similarity NPC472387
0.9191 High Similarity NPC258044
0.9191 High Similarity NPC293626
0.9186 High Similarity NPC223426
0.9186 High Similarity NPC81042
0.9186 High Similarity NPC34267
0.9186 High Similarity NPC214621
0.9176 High Similarity NPC198125
0.9176 High Similarity NPC95421
0.9167 High Similarity NPC189312
0.9153 High Similarity NPC269046
0.9153 High Similarity NPC7839
0.9153 High Similarity NPC142291
0.9148 High Similarity NPC87583
0.9143 High Similarity NPC162394
0.9143 High Similarity NPC156785
0.9143 High Similarity NPC35924
0.9143 High Similarity NPC321916
0.9143 High Similarity NPC470718
0.9143 High Similarity NPC241781
0.9143 High Similarity NPC199172
0.9138 High Similarity NPC299149
0.9138 High Similarity NPC277710
0.9138 High Similarity NPC153578
0.9138 High Similarity NPC114257
0.9133 High Similarity NPC67629
0.9133 High Similarity NPC79736
0.9123 High Similarity NPC47521
0.9123 High Similarity NPC476365
0.9118 High Similarity NPC31034
0.9118 High Similarity NPC116745
0.9118 High Similarity NPC45400
0.9118 High Similarity NPC473818
0.9112 High Similarity NPC165720
0.9107 High Similarity NPC14030
0.9107 High Similarity NPC291957
0.9096 High Similarity NPC237202
0.9091 High Similarity NPC470713
0.9091 High Similarity NPC223860
0.9091 High Similarity NPC249560
0.9091 High Similarity NPC460984
0.9091 High Similarity NPC470416
0.9091 High Similarity NPC25946
0.9091 High Similarity NPC49690
0.9091 High Similarity NPC470717
0.9091 High Similarity NPC470720
0.9091 High Similarity NPC21359
0.9091 High Similarity NPC275977
0.9086 High Similarity NPC170203
0.908 High Similarity NPC217520
0.908 High Similarity NPC139571
0.908 High Similarity NPC477895
0.9075 High Similarity NPC253685
0.9066 High Similarity NPC174140
0.9064 High Similarity NPC222455
0.9064 High Similarity NPC229687
0.9064 High Similarity NPC105283
0.9059 High Similarity NPC8856
0.9059 High Similarity NPC473278
0.9059 High Similarity NPC260504
0.9059 High Similarity NPC89809
0.9056 High Similarity NPC476358
0.9053 High Similarity NPC88043
0.9053 High Similarity NPC29830
0.9053 High Similarity NPC168822
0.9053 High Similarity NPC470898
0.9053 High Similarity NPC121290
0.9045 High Similarity NPC205721
0.904 High Similarity NPC295625
0.904 High Similarity NPC473554
0.904 High Similarity NPC33083
0.904 High Similarity NPC470719
0.904 High Similarity NPC221140
0.904 High Similarity NPC475352
0.904 High Similarity NPC473686
0.904 High Similarity NPC475220
0.904 High Similarity NPC112380
0.904 High Similarity NPC229817
0.9034 High Similarity NPC473631
0.9034 High Similarity NPC475662
0.9034 High Similarity NPC293227
0.9034 High Similarity NPC473717
0.9034 High Similarity NPC476203
0.9034 High Similarity NPC36138
0.9029 High Similarity NPC212290
0.9029 High Similarity NPC472726
0.9029 High Similarity NPC472725
0.9023 High Similarity NPC154741
0.9023 High Similarity NPC296018
0.9017 High Similarity NPC263119
0.9017 High Similarity NPC34436
0.9017 High Similarity NPC166674
0.9017 High Similarity NPC473550
0.9017 High Similarity NPC46640
0.9017 High Similarity NPC219600
0.9012 High Similarity NPC20505
0.9012 High Similarity NPC231194
0.9012 High Similarity NPC471416
0.9012 High Similarity NPC51326
0.9012 High Similarity NPC218488
0.9012 High Similarity NPC181778
0.9012 High Similarity NPC155763
0.9012 High Similarity NPC34287
0.9012 High Similarity NPC235260
0.9006 High Similarity NPC229729
0.9006 High Similarity NPC298847
0.8994 High Similarity NPC77660
0.8994 High Similarity NPC300537
0.8994 High Similarity NPC472876
0.8994 High Similarity NPC189142
0.8994 High Similarity NPC127782
0.8989 High Similarity NPC64755
0.8989 High Similarity NPC269625
0.8988 High Similarity NPC289346

  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 NPC231254 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
0.896 High Similarity NPD7993 Clinical (unspecified phase)
0.8902 High Similarity NPD7472 Approved
0.8902 High Similarity NPD7074 Phase 3
0.8895 High Similarity NPD3818 Discontinued
0.8857 High Similarity NPD4338 Clinical (unspecified phase)
0.8851 High Similarity NPD6797 Phase 2
0.8844 High Similarity NPD7054 Approved
0.881 High Similarity NPD4868 Clinical (unspecified phase)
0.8807 High Similarity NPD8312 Approved
0.8807 High Similarity NPD8313 Approved
0.88 High Similarity NPD7251 Discontinued
0.8757 High Similarity NPD4381 Clinical (unspecified phase)
0.875 High Similarity NPD7808 Phase 3
0.8671 High Similarity NPD6167 Clinical (unspecified phase)
0.8671 High Similarity NPD6168 Clinical (unspecified phase)
0.8671 High Similarity NPD6166 Phase 2
0.8564 High Similarity NPD8397 Clinical (unspecified phase)
0.847 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8418 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8418 Intermediate Similarity NPD5844 Phase 1
0.8412 Intermediate Similarity NPD1934 Approved
0.8391 Intermediate Similarity NPD6959 Discontinued
0.8385 Intermediate Similarity NPD8151 Discontinued
0.838 Intermediate Similarity NPD6559 Discontinued
0.8363 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8363 Intermediate Similarity NPD1465 Phase 2
0.8352 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8343 Intermediate Similarity NPD6232 Discontinued
0.8305 Intermediate Similarity NPD7473 Discontinued
0.8256 Intermediate Similarity NPD8455 Phase 2
0.8256 Intermediate Similarity NPD7819 Suspended
0.8218 Intermediate Similarity NPD3749 Approved
0.8187 Intermediate Similarity NPD4380 Phase 2
0.8156 Intermediate Similarity NPD7228 Approved
0.8156 Intermediate Similarity NPD3751 Discontinued
0.815 Intermediate Similarity NPD2801 Approved
0.8136 Intermediate Similarity NPD3787 Discontinued
0.8114 Intermediate Similarity NPD7075 Discontinued
0.8103 Intermediate Similarity NPD3817 Phase 2
0.8079 Intermediate Similarity NPD7199 Phase 2
0.8057 Intermediate Similarity NPD7768 Phase 2
0.8057 Intermediate Similarity NPD3882 Suspended
0.8047 Intermediate Similarity NPD1511 Approved
0.8035 Intermediate Similarity NPD7411 Suspended
0.8 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD5402 Approved
0.7966 Intermediate Similarity NPD6234 Discontinued
0.7953 Intermediate Similarity NPD1512 Approved
0.7943 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7938 Intermediate Similarity NPD7435 Discontinued
0.7929 Intermediate Similarity NPD7783 Phase 2
0.7929 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7921 Intermediate Similarity NPD5494 Approved
0.7907 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7903 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7889 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7886 Intermediate Similarity NPD6801 Discontinued
0.7886 Intermediate Similarity NPD37 Approved
0.788 Intermediate Similarity NPD7685 Pre-registration
0.7876 Intermediate Similarity NPD6776 Approved
0.7876 Intermediate Similarity NPD6781 Approved
0.7876 Intermediate Similarity NPD6778 Approved
0.7876 Intermediate Similarity NPD6779 Approved
0.7876 Intermediate Similarity NPD6782 Approved
0.7876 Intermediate Similarity NPD6780 Approved
0.7876 Intermediate Similarity NPD6777 Approved
0.7861 Intermediate Similarity NPD1653 Approved
0.7857 Intermediate Similarity NPD1549 Phase 2
0.7853 Intermediate Similarity NPD4966 Approved
0.7853 Intermediate Similarity NPD4967 Phase 2
0.7853 Intermediate Similarity NPD4965 Approved
0.7806 Intermediate Similarity NPD7871 Phase 2
0.7806 Intermediate Similarity NPD7870 Phase 2
0.7803 Intermediate Similarity NPD5403 Approved
0.7798 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7789 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7789 Intermediate Similarity NPD7874 Approved
0.7784 Intermediate Similarity NPD7240 Approved
0.7765 Intermediate Similarity NPD3750 Approved
0.7755 Intermediate Similarity NPD7697 Approved
0.7755 Intermediate Similarity NPD7698 Approved
0.7755 Intermediate Similarity NPD7696 Phase 3
0.7733 Intermediate Similarity NPD6799 Approved
0.7688 Intermediate Similarity NPD5401 Approved
0.7688 Intermediate Similarity NPD7701 Phase 2
0.7688 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD6599 Discontinued
0.7626 Intermediate Similarity NPD8320 Phase 1
0.7626 Intermediate Similarity NPD8319 Approved
0.7617 Intermediate Similarity NPD6534 Approved
0.7617 Intermediate Similarity NPD6535 Approved
0.7614 Intermediate Similarity NPD6823 Phase 2
0.759 Intermediate Similarity NPD7699 Phase 2
0.759 Intermediate Similarity NPD7700 Phase 2
0.7586 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7579 Intermediate Similarity NPD8150 Discontinued
0.7574 Intermediate Similarity NPD7801 Approved
0.7574 Intermediate Similarity NPD1510 Phase 2
0.7544 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD2796 Approved
0.7529 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD7390 Discontinued
0.7514 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD6190 Approved
0.7514 Intermediate Similarity NPD3226 Approved
0.75 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3926 Phase 2
0.7487 Intermediate Similarity NPD7680 Approved
0.7486 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD2532 Approved
0.7486 Intermediate Similarity NPD2533 Approved
0.7486 Intermediate Similarity NPD2534 Approved
0.7485 Intermediate Similarity NPD7266 Discontinued
0.7471 Intermediate Similarity NPD3748 Approved
0.7457 Intermediate Similarity NPD4628 Phase 3
0.7457 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD943 Approved
0.744 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD1613 Approved
0.7416 Intermediate Similarity NPD7458 Discontinued
0.7399 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD230 Phase 1
0.7396 Intermediate Similarity NPD8434 Phase 2
0.7386 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD6212 Phase 3
0.7385 Intermediate Similarity NPD6213 Phase 3
0.7385 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD919 Approved
0.7374 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD1240 Approved
0.7326 Intermediate Similarity NPD5406 Approved
0.7326 Intermediate Similarity NPD5408 Approved
0.7326 Intermediate Similarity NPD1551 Phase 2
0.7326 Intermediate Similarity NPD5405 Approved
0.7326 Intermediate Similarity NPD5404 Approved
0.732 Intermediate Similarity NPD4287 Approved
0.7294 Intermediate Similarity NPD1933 Approved
0.7291 Intermediate Similarity NPD7584 Approved
0.7283 Intermediate Similarity NPD2346 Discontinued
0.7267 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD1607 Approved
0.725 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD2935 Discontinued
0.7207 Intermediate Similarity NPD920 Approved
0.7204 Intermediate Similarity NPD8127 Discontinued
0.7204 Intermediate Similarity NPD1247 Approved
0.7202 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD447 Suspended
0.7191 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7173 Intermediate Similarity NPD5953 Discontinued
0.7166 Intermediate Similarity NPD7229 Phase 3
0.7143 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD7930 Approved
0.7118 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD7177 Discontinued
0.7102 Intermediate Similarity NPD6674 Discontinued
0.7087 Intermediate Similarity NPD7585 Approved
0.7086 Intermediate Similarity NPD2344 Approved
0.7083 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD8059 Phase 3
0.7079 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD5711 Approved
0.7074 Intermediate Similarity NPD5710 Approved
0.7073 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD2799 Discontinued
0.7068 Intermediate Similarity NPD7286 Phase 2
0.7062 Intermediate Similarity NPD8166 Discontinued
0.7062 Intermediate Similarity NPD7003 Approved
0.7059 Intermediate Similarity NPD3027 Phase 3
0.7056 Intermediate Similarity NPD6273 Approved
0.7039 Intermediate Similarity NPD7583 Approved
0.7026 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD3764 Approved
0.7018 Intermediate Similarity NPD2313 Discontinued
0.701 Intermediate Similarity NPD5006 Approved
0.701 Intermediate Similarity NPD5005 Approved
0.7006 Intermediate Similarity NPD1243 Approved
0.7006 Intermediate Similarity NPD2800 Approved
0.7 Intermediate Similarity NPD4908 Phase 1
0.6966 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6947 Remote Similarity NPD5242 Approved
0.6946 Remote Similarity NPD8285 Discontinued
0.6935 Remote Similarity NPD4288 Approved
0.6932 Remote Similarity NPD6099 Approved
0.6932 Remote Similarity NPD6100 Approved
0.6927 Remote Similarity NPD2309 Approved
0.6923 Remote Similarity NPD1203 Approved
0.6923 Remote Similarity NPD7549 Discontinued
0.6919 Remote Similarity NPD6798 Discontinued
0.6919 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6914 Remote Similarity NPD7097 Phase 1
0.6901 Remote Similarity NPD6832 Phase 2
0.6897 Remote Similarity NPD4420 Approved
0.6875 Remote Similarity NPD7033 Discontinued
0.6845 Remote Similarity NPD9269 Phase 2
0.6845 Remote Similarity NPD5353 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