NPASS Compound

Structure

NPC144283 OpenBabel07101719252D 31 34 0 0 0 0 0 0 0 0999 V2000 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 17 2 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 11 18 2 0 0 0 0 11 21 1 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 13 19 2 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 24 2 0 0 0 0 15 25 1 0 0 0 0 16 19 1 0 0 0 0 16 26 2 0 0 0 0 17 19 1 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 21 27 2 0 0 0 0 22 28 2 0 0 0 0 23 29 2 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.11
Volume:	419.328
LogP:	3.153
LogD:	2.317
LogS:	-5.75
# Rotatable Bonds:	3
TPSA:	106.97
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.814
Synthetic Accessibility Score:	2.959
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.142
MDCK Permeability:	1.5851745047257282e-05
Pgp-inhibitor:	0.899
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	96.03746795654297%
Volume Distribution (VD):	0.149
Pgp-substrate:	1.487573504447937%

ADMET: Metabolism

CYP1A2-inhibitor:	0.879
CYP1A2-substrate:	0.832
CYP2C19-inhibitor:	0.881
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.911
CYP2C9-substrate:	0.718
CYP2D6-inhibitor:	0.797
CYP2D6-substrate:	0.17
CYP3A4-inhibitor:	0.779
CYP3A4-substrate:	0.133

ADMET: Excretion

Clearance (CL):	2.716
Half-life (T1/2):	0.062

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.276
Drug-inuced Liver Injury (DILI):	0.854
AMES Toxicity:	0.865
Rat Oral Acute Toxicity:	0.823
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.426
Carcinogencity:	0.802
Eye Corrosion:	0.003
Eye Irritation:	0.907
Respiratory Toxicity:	0.074

Download Data

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

Natural Product: NPC144283

Natural Product ID:	NPC144283
*Common Name:**	Burmanin A
IUPAC Name:	6-hydroxy-5-methoxy-3-(5-methoxy-7-methyl-1,4-dioxonaphthalen-2-yl)-2-methylnaphthalene-1,4-dione
Synonyms:	Burmanin A
Standard InCHIKey:	WNJLSOROQWHGIS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H18O7/c1-10-7-13-19(17(8-10)30-3)16(26)9-14(22(13)28)18-11(2)21(27)12-5-6-15(25)24(31-4)20(12)23(18)29/h5-9,25H,1-4H3
SMILES:	Cc1cc2c(C(=O)C=C(C3=C(C)C(=O)c4ccc(c(c4C3=O)OC)O)C2=O)c(c1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071225
PubChem CID:	66553900
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO32707	burman diospyros burmanica	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22858297]

☑ 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

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	24000.0	nM	PMID[528954]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	0.053	nM	PMID[528954]
NPT2	Others	Unspecified		Ratio IC50	=	453.0	n.a.	PMID[528954]

☑ 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 NPC144283 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	1657
0.2-0.3	3996
0.3-0.4	10510
0.4-0.5	7677
0.5-0.6	3446
0.6-0.7	6416
0.7-0.8	6971
0.8-0.85	1437
0.85-0.9	142
0.9-0.95	36
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9527	High Similarity	NPC164912
0.9459	High Similarity	NPC118427
0.9459	High Similarity	NPC302783
0.9459	High Similarity	NPC473201
0.9448	High Similarity	NPC73416
0.9448	High Similarity	NPC160777
0.9338	High Similarity	NPC279605
0.9306	High Similarity	NPC84273
0.9241	High Similarity	NPC11314
0.92	High Similarity	NPC472838
0.92	High Similarity	NPC306011
0.9189	High Similarity	NPC58373
0.9167	High Similarity	NPC26386
0.915	High Similarity	NPC37543
0.915	High Similarity	NPC178976
0.915	High Similarity	NPC199463
0.9133	High Similarity	NPC58310
0.9133	High Similarity	NPC295977
0.911	High Similarity	NPC192597
0.911	High Similarity	NPC176030
0.911	High Similarity	NPC141817
0.911	High Similarity	NPC169214
0.911	High Similarity	NPC229218
0.9085	High Similarity	NPC5379
0.9085	High Similarity	NPC14561
0.9085	High Similarity	NPC77807
0.9034	High Similarity	NPC223336
0.9013	High Similarity	NPC149889
0.9013	High Similarity	NPC312338
0.8986	High Similarity	NPC196941
0.8986	High Similarity	NPC309169
0.8974	High Similarity	NPC311740
0.8961	High Similarity	NPC213401
0.8954	High Similarity	NPC107109
0.8947	High Similarity	NPC75377
0.894	High Similarity	NPC134293
0.8933	High Similarity	NPC52692
0.8926	High Similarity	NPC225351
0.891	High Similarity	NPC84571
0.8904	High Similarity	NPC470407
0.8889	High Similarity	NPC137125
0.8889	High Similarity	NPC3744
0.8867	High Similarity	NPC39361
0.8854	High Similarity	NPC318081
0.8851	High Similarity	NPC69755
0.8846	High Similarity	NPC104876
0.8846	High Similarity	NPC245891
0.8839	High Similarity	NPC288353
0.8831	High Similarity	NPC475770
0.8831	High Similarity	NPC474000
0.8831	High Similarity	NPC93552
0.8824	High Similarity	NPC70320
0.8816	High Similarity	NPC37220
0.8816	High Similarity	NPC472837
0.8816	High Similarity	NPC237441
0.8805	High Similarity	NPC303174
0.88	High Similarity	NPC478019
0.8792	High Similarity	NPC53016
0.8792	High Similarity	NPC50954
0.879	High Similarity	NPC185617
0.8759	High Similarity	NPC258502
0.8758	High Similarity	NPC472279
0.8758	High Similarity	NPC475718
0.8733	High Similarity	NPC91694
0.8733	High Similarity	NPC300603
0.8733	High Similarity	NPC472836
0.8718	High Similarity	NPC478223
0.871	High Similarity	NPC305710
0.871	High Similarity	NPC127172
0.8707	High Similarity	NPC416
0.8707	High Similarity	NPC61398
0.8701	High Similarity	NPC78505
0.8701	High Similarity	NPC256406
0.8699	High Similarity	NPC324929
0.869	High Similarity	NPC50924
0.8684	High Similarity	NPC77598
0.8671	High Similarity	NPC471973
0.8667	High Similarity	NPC239608
0.8667	High Similarity	NPC46161
0.8662	High Similarity	NPC167098
0.8662	High Similarity	NPC296044
0.8662	High Similarity	NPC136674
0.8654	High Similarity	NPC168247
0.8654	High Similarity	NPC57674
0.8654	High Similarity	NPC230149
0.8654	High Similarity	NPC152951
0.8654	High Similarity	NPC234485
0.8654	High Similarity	NPC117992
0.8649	High Similarity	NPC1268
0.8636	High Similarity	NPC31132
0.8636	High Similarity	NPC85131
0.8634	High Similarity	NPC263212
0.8634	High Similarity	NPC43319
0.8634	High Similarity	NPC37870
0.863	High Similarity	NPC88065
0.863	High Similarity	NPC89504
0.863	High Similarity	NPC95485
0.8627	High Similarity	NPC55327
0.8627	High Similarity	NPC474556
0.8625	High Similarity	NPC270837
0.8625	High Similarity	NPC236132
0.8621	High Similarity	NPC294226
0.8609	High Similarity	NPC142165
0.8608	High Similarity	NPC235448
0.8608	High Similarity	NPC204879
0.8608	High Similarity	NPC477410
0.8599	High Similarity	NPC470762
0.8599	High Similarity	NPC472455
0.8599	High Similarity	NPC474167
0.8598	High Similarity	NPC199357
0.8591	High Similarity	NPC82336
0.8591	High Similarity	NPC78987
0.859	High Similarity	NPC33051
0.859	High Similarity	NPC227337
0.859	High Similarity	NPC70433
0.859	High Similarity	NPC273462
0.859	High Similarity	NPC472905
0.859	High Similarity	NPC49402
0.858	High Similarity	NPC218226
0.8571	High Similarity	NPC264550
0.8571	High Similarity	NPC200060
0.8571	High Similarity	NPC472450
0.8571	High Similarity	NPC171916
0.8571	High Similarity	NPC38545
0.8571	High Similarity	NPC261322
0.8571	High Similarity	NPC264289
0.8571	High Similarity	NPC333691
0.8571	High Similarity	NPC195763
0.8571	High Similarity	NPC40290
0.8571	High Similarity	NPC275780
0.8571	High Similarity	NPC69430
0.8571	High Similarity	NPC142876
0.8571	High Similarity	NPC139293
0.8571	High Similarity	NPC239752
0.8562	High Similarity	NPC312929
0.8562	High Similarity	NPC245584
0.8562	High Similarity	NPC478018
0.8562	High Similarity	NPC294965
0.8562	High Similarity	NPC126767
0.8562	High Similarity	NPC190648
0.8562	High Similarity	NPC289042
0.8562	High Similarity	NPC149389
0.8562	High Similarity	NPC56433
0.8562	High Similarity	NPC118027
0.8553	High Similarity	NPC56085
0.8553	High Similarity	NPC228785
0.8553	High Similarity	NPC157133
0.8553	High Similarity	NPC14353
0.8553	High Similarity	NPC474960
0.8553	High Similarity	NPC36217
0.8545	High Similarity	NPC245975
0.8544	High Similarity	NPC219867
0.8544	High Similarity	NPC187745
0.8544	High Similarity	NPC472963
0.8544	High Similarity	NPC304008
0.8544	High Similarity	NPC474681
0.8544	High Similarity	NPC161960
0.8544	High Similarity	NPC180011
0.8544	High Similarity	NPC218313
0.8543	High Similarity	NPC254659
0.8542	High Similarity	NPC66905
0.8542	High Similarity	NPC117609
0.8537	High Similarity	NPC158226
0.8535	High Similarity	NPC66508
0.8535	High Similarity	NPC39184
0.8535	High Similarity	NPC130589
0.8535	High Similarity	NPC38898
0.8535	High Similarity	NPC226656
0.8535	High Similarity	NPC472280
0.8535	High Similarity	NPC256925
0.8535	High Similarity	NPC134287
0.8535	High Similarity	NPC234255
0.8533	High Similarity	NPC124365
0.8528	High Similarity	NPC163130
0.8528	High Similarity	NPC476637
0.8528	High Similarity	NPC165979
0.8526	High Similarity	NPC474993
0.8526	High Similarity	NPC237994
0.8526	High Similarity	NPC180388
0.8519	High Similarity	NPC39091
0.8516	High Similarity	NPC280295
0.8516	High Similarity	NPC290954
0.8516	High Similarity	NPC255641
0.8516	High Similarity	NPC470568
0.8514	High Similarity	NPC264022
0.8509	High Similarity	NPC248638
0.8509	High Similarity	NPC207690
0.8509	High Similarity	NPC220313
0.8509	High Similarity	NPC477689
0.8509	High Similarity	NPC23298
0.8509	High Similarity	NPC189473
0.8509	High Similarity	NPC152659
0.8509	High Similarity	NPC236521
0.8509	High Similarity	NPC186686
0.8509	High Similarity	NPC101769
0.8506	High Similarity	NPC254702
0.8506	High Similarity	NPC80710
0.8506	High Similarity	NPC166036
0.8506	High Similarity	NPC203077
0.8506	High Similarity	NPC139364

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 NPC144283 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	993
0.2-0.3	1461
0.3-0.4	2641
0.4-0.5	1921
0.5-0.6	1060
0.6-0.7	525
0.7-0.8	166
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8562	High Similarity	NPD6232	Discontinued
0.8519	High Similarity	NPD7473	Discontinued
0.8353	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD2801	Approved
0.8239	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1934	Approved
0.8137	Intermediate Similarity	NPD3882	Suspended
0.8092	Intermediate Similarity	NPD2346	Discontinued
0.8026	Intermediate Similarity	NPD2935	Discontinued
0.7987	Intermediate Similarity	NPD3226	Approved
0.7962	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD9494	Approved
0.7937	Intermediate Similarity	NPD4380	Phase 2
0.7931	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6166	Phase 2
0.7898	Intermediate Similarity	NPD1511	Approved
0.7879	Intermediate Similarity	NPD5494	Approved
0.7875	Intermediate Similarity	NPD7458	Discontinued
0.787	Intermediate Similarity	NPD5844	Phase 1
0.7857	Intermediate Similarity	NPD2344	Approved
0.7843	Intermediate Similarity	NPD2799	Discontinued
0.7829	Intermediate Similarity	NPD1607	Approved
0.7823	Intermediate Similarity	NPD1470	Approved
0.7821	Intermediate Similarity	NPD7003	Approved
0.7815	Intermediate Similarity	NPD943	Approved
0.7811	Intermediate Similarity	NPD3818	Discontinued
0.7799	Intermediate Similarity	NPD1512	Approved
0.7791	Intermediate Similarity	NPD7819	Suspended
0.7736	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1510	Phase 2
0.7725	Intermediate Similarity	NPD6959	Discontinued
0.7719	Intermediate Similarity	NPD7074	Phase 3
0.7697	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1240	Approved
0.7683	Intermediate Similarity	NPD1465	Phase 2
0.7661	Intermediate Similarity	NPD7054	Approved
0.7658	Intermediate Similarity	NPD2309	Approved
0.7651	Intermediate Similarity	NPD7075	Discontinued
0.7651	Intermediate Similarity	NPD2798	Approved
0.764	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD3817	Phase 2
0.7625	Intermediate Similarity	NPD2533	Approved
0.7625	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2534	Approved
0.7625	Intermediate Similarity	NPD2532	Approved
0.7619	Intermediate Similarity	NPD3972	Approved
0.7616	Intermediate Similarity	NPD7472	Approved
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.7595	Intermediate Similarity	NPD8166	Discontinued
0.7586	Intermediate Similarity	NPD1651	Approved
0.7576	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD2313	Discontinued
0.7564	Intermediate Similarity	NPD5404	Approved
0.7564	Intermediate Similarity	NPD5408	Approved
0.7564	Intermediate Similarity	NPD5405	Approved
0.7564	Intermediate Similarity	NPD5406	Approved
0.7562	Intermediate Similarity	NPD7390	Discontinued
0.7551	Intermediate Similarity	NPD1201	Approved
0.7543	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD447	Suspended
0.7532	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1283	Approved
0.7516	Intermediate Similarity	NPD1471	Phase 3
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD3300	Phase 2
0.75	Intermediate Similarity	NPD7028	Phase 2
0.7486	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3750	Approved
0.7471	Intermediate Similarity	NPD6797	Phase 2
0.7468	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1549	Phase 2
0.7458	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7411	Suspended
0.7453	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD5536	Phase 2
0.7443	Intermediate Similarity	NPD8313	Approved
0.7443	Intermediate Similarity	NPD8312	Approved
0.744	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7251	Discontinued
0.7427	Intermediate Similarity	NPD3926	Phase 2
0.7415	Intermediate Similarity	NPD4626	Approved
0.741	Intermediate Similarity	NPD6801	Discontinued
0.7405	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1876	Approved
0.7386	Intermediate Similarity	NPD7808	Phase 3
0.7355	Intermediate Similarity	NPD4060	Phase 1
0.7351	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6781	Approved
0.7351	Intermediate Similarity	NPD6778	Approved
0.7351	Intermediate Similarity	NPD6776	Approved
0.7351	Intermediate Similarity	NPD6779	Approved
0.7351	Intermediate Similarity	NPD6777	Approved
0.7351	Intermediate Similarity	NPD6782	Approved
0.7351	Intermediate Similarity	NPD6780	Approved
0.7346	Intermediate Similarity	NPD6799	Approved
0.7342	Intermediate Similarity	NPD2796	Approved
0.7337	Intermediate Similarity	NPD3749	Approved
0.733	Intermediate Similarity	NPD6559	Discontinued
0.7321	Intermediate Similarity	NPD5978	Approved
0.7321	Intermediate Similarity	NPD5977	Approved
0.7317	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1281	Approved
0.7308	Intermediate Similarity	NPD1933	Approved
0.7294	Intermediate Similarity	NPD6234	Discontinued
0.7283	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7768	Phase 2
0.7273	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6273	Approved
0.7244	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3620	Phase 2
0.7234	Intermediate Similarity	NPD7435	Discontinued
0.7219	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1247	Approved
0.7205	Intermediate Similarity	NPD2800	Approved
0.7202	Intermediate Similarity	NPD37	Approved
0.72	Intermediate Similarity	NPD3751	Discontinued
0.72	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD919	Approved
0.7172	Intermediate Similarity	NPD5283	Phase 1
0.717	Intermediate Similarity	NPD3748	Approved
0.7153	Intermediate Similarity	NPD228	Approved
0.7152	Intermediate Similarity	NPD6651	Approved
0.7143	Intermediate Similarity	NPD7696	Phase 3
0.7143	Intermediate Similarity	NPD7697	Approved
0.7143	Intermediate Similarity	NPD7698	Approved
0.7135	Intermediate Similarity	NPD8151	Discontinued
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.7134	Intermediate Similarity	NPD2979	Phase 3
0.7127	Intermediate Similarity	NPD8434	Phase 2
0.7125	Intermediate Similarity	NPD2438	Suspended
0.7124	Intermediate Similarity	NPD1203	Approved
0.7118	Intermediate Similarity	NPD5402	Approved
0.7118	Intermediate Similarity	NPD2296	Approved
0.7115	Intermediate Similarity	NPD3764	Approved
0.7114	Intermediate Similarity	NPD5691	Approved
0.7105	Intermediate Similarity	NPD7870	Phase 2
0.7105	Intermediate Similarity	NPD7871	Phase 2
0.7102	Intermediate Similarity	NPD7177	Discontinued
0.7102	Intermediate Similarity	NPD7228	Approved
0.7089	Intermediate Similarity	NPD230	Phase 1
0.7083	Intermediate Similarity	NPD7701	Phase 2
0.7081	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6535	Approved
0.7081	Intermediate Similarity	NPD6534	Approved
0.7076	Intermediate Similarity	NPD4965	Approved
0.7076	Intermediate Similarity	NPD4967	Phase 2
0.7076	Intermediate Similarity	NPD4966	Approved
0.7069	Intermediate Similarity	NPD5710	Approved
0.7069	Intermediate Similarity	NPD5711	Approved
0.7067	Intermediate Similarity	NPD2932	Approved
0.7063	Intermediate Similarity	NPD4308	Phase 3
0.7055	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3027	Phase 3
0.7041	Intermediate Similarity	NPD6873	Phase 2
0.7027	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6212	Phase 3
0.7027	Intermediate Similarity	NPD6213	Phase 3
0.7024	Intermediate Similarity	NPD824	Approved
0.7019	Intermediate Similarity	NPD1551	Phase 2
0.7019	Intermediate Similarity	NPD6100	Approved
0.7019	Intermediate Similarity	NPD6099	Approved
0.7013	Intermediate Similarity	NPD1164	Approved
0.7012	Intermediate Similarity	NPD6190	Approved
0.7011	Intermediate Similarity	NPD7199	Phase 2
0.7011	Intermediate Similarity	NPD8127	Discontinued
0.701	Intermediate Similarity	NPD7874	Approved
0.701	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5403	Approved
0.7006	Intermediate Similarity	NPD6798	Discontinued
0.7006	Intermediate Similarity	NPD3268	Approved
0.7006	Intermediate Similarity	NPD411	Approved
0.7	Intermediate Similarity	NPD6844	Discontinued
0.7	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6823	Phase 2
0.6987	Remote Similarity	NPD6832	Phase 2
0.6983	Remote Similarity	NPD5953	Discontinued
0.6981	Remote Similarity	NPD6355	Discontinued
0.6974	Remote Similarity	NPD7801	Approved
0.6968	Remote Similarity	NPD7699	Phase 2
0.6968	Remote Similarity	NPD7700	Phase 2
0.6954	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3019	Approved
0.6951	Remote Similarity	NPD4110	Phase 3
0.6951	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5049	Phase 3
0.6943	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6385	Approved
0.6941	Remote Similarity	NPD6386	Approved
0.6932	Remote Similarity	NPD7184	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