NPASS Compound

Structure

NPC17059 OpenBabel07101719512D 21 24 0 0 1 0 0 0 0 0999 V2000 -3.2085 -2.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1867 -2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8995 -1.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8558 -2.1535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 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 -4.3776 0.4067 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 -3.5686 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 -0.3364 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 11 2 0 0 0 0 5 12 2 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 17 1 0 0 0 0 13 8 1 1 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 6 1 1 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	283.13
Volume:	285.818
LogP:	1.533
LogD:	1.587
LogS:	-2.332
# Rotatable Bonds:	2
TPSA:	65.2
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.87
Synthetic Accessibility Score:	2.976
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.631
MDCK Permeability:	9.593655704520643e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.637

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.668
Plasma Protein Binding (PPB):	51.38550567626953%
Volume Distribution (VD):	0.742
Pgp-substrate:	38.70112609863281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.479
CYP2C19-inhibitor:	0.556
CYP2C19-substrate:	0.18
CYP2C9-inhibitor:	0.191
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.694
CYP3A4-inhibitor:	0.566
CYP3A4-substrate:	0.182

ADMET: Excretion

Clearance (CL):	5.954
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.796
Drug-inuced Liver Injury (DILI):	0.202
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.779
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.377
Carcinogencity:	0.162
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.135

Download Data

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

Natural Product: NPC17059

Natural Product ID:	NPC17059
*Common Name:**	Brevianamide F
IUPAC Name:	(3S,8aS)-3-(1H-indol-3-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms:	Brevianamide F
Standard InCHIKey:	RYFZBPVMVYTEKZ-KBPBESRZSA-N
Standard InCHI:	InChI=1S/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14-/m0/s1
SMILES:	OC1=N[C@@H](Cc2c[nH]c3c2cccc3)C(=O)N2[C@H]1CCC2
Synthetic Gene Cluster:	BGC0000356;
ChEMBL Identifier:	CHEMBL563557
PubChem CID:	181567
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO41486	Streptomyces bullii + Aspergillus fumigatus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[31953204]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	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

Activity Type	# Activity
IC50	4
MIC	4
Others	4

Activity Type	# Activity
Cell Line	4
Individual Protein	3
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2960	Individual Protein	Brevianamide F prenyltransferase	Aspergillus fumigatus	Km	=	55000.0	nM	PMID[497660]
NPT2960	Individual Protein	Brevianamide F prenyltransferase	Aspergillus fumigatus	Kcat	=	5.57	/s	PMID[497660]
NPT2960	Individual Protein	Brevianamide F prenyltransferase	Aspergillus fumigatus	Ratio	=	675.0	n.a.	PMID[497660]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[497661]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	100000.0	nM	PMID[497661]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	200000.0	nM	PMID[497663]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	83.7	ug.mL-1	PMID[497662]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.6	ug.mL-1	PMID[497664]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	11.9	ug.mL-1	PMID[497664]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	20.0	ug.mL-1	PMID[497664]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC	=	44170.0	nM	PMID[497666]

☑ 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 NPC17059 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	386
0.1-0.2	3847
0.2-0.3	21292
0.3-0.4	10335
0.4-0.5	2245
0.5-0.6	2420
0.6-0.7	1408
0.7-0.8	636
0.8-0.85	91
0.85-0.9	32
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC228835
0.9461	High Similarity	NPC11126
0.9405	High Similarity	NPC91179
0.9138	High Similarity	NPC213629
0.8944	High Similarity	NPC171317
0.8914	High Similarity	NPC94752
0.8865	High Similarity	NPC54420
0.8859	High Similarity	NPC473376
0.8814	High Similarity	NPC321708
0.88	High Similarity	NPC165495
0.8778	High Similarity	NPC294693
0.877	High Similarity	NPC478158
0.877	High Similarity	NPC162860
0.875	High Similarity	NPC99939
0.875	High Similarity	NPC308931
0.8721	High Similarity	NPC110500
0.8721	High Similarity	NPC149155
0.8721	High Similarity	NPC203468
0.8689	High Similarity	NPC293917
0.8678	High Similarity	NPC283219
0.8678	High Similarity	NPC126709
0.8678	High Similarity	NPC248041
0.8671	High Similarity	NPC267885
0.8634	High Similarity	NPC473640
0.8621	High Similarity	NPC14113
0.8621	High Similarity	NPC145885
0.8621	High Similarity	NPC84827
0.8595	High Similarity	NPC475506
0.8587	High Similarity	NPC100321
0.8549	High Similarity	NPC477715
0.8548	High Similarity	NPC155143
0.8542	High Similarity	NPC478157
0.8538	High Similarity	NPC49954
0.8538	High Similarity	NPC474561
0.8521	High Similarity	NPC279918
0.8514	High Similarity	NPC59269
0.8505	High Similarity	NPC477714
0.8492	Intermediate Similarity	NPC235684
0.849	Intermediate Similarity	NPC54744
0.8488	Intermediate Similarity	NPC78020
0.8488	Intermediate Similarity	NPC63751
0.8471	Intermediate Similarity	NPC282231
0.8448	Intermediate Similarity	NPC161861
0.8438	Intermediate Similarity	NPC75634
0.8436	Intermediate Similarity	NPC15102
0.8385	Intermediate Similarity	NPC72956
0.8377	Intermediate Similarity	NPC107077
0.8377	Intermediate Similarity	NPC223791
0.8342	Intermediate Similarity	NPC471194
0.8342	Intermediate Similarity	NPC471193
0.8342	Intermediate Similarity	NPC153980
0.8342	Intermediate Similarity	NPC6865
0.8324	Intermediate Similarity	NPC54988
0.8314	Intermediate Similarity	NPC194640
0.8306	Intermediate Similarity	NPC117244
0.8306	Intermediate Similarity	NPC473763
0.8305	Intermediate Similarity	NPC64436
0.8305	Intermediate Similarity	NPC217372
0.8305	Intermediate Similarity	NPC15573
0.8305	Intermediate Similarity	NPC183662
0.829	Intermediate Similarity	NPC320968
0.8258	Intermediate Similarity	NPC219336
0.8247	Intermediate Similarity	NPC110602
0.8247	Intermediate Similarity	NPC75726
0.8247	Intermediate Similarity	NPC31385
0.8245	Intermediate Similarity	NPC470497
0.8235	Intermediate Similarity	NPC131887
0.8235	Intermediate Similarity	NPC470499
0.8218	Intermediate Similarity	NPC160105
0.8214	Intermediate Similarity	NPC471192
0.8207	Intermediate Similarity	NPC476460
0.8202	Intermediate Similarity	NPC111275
0.8187	Intermediate Similarity	NPC62749
0.8182	Intermediate Similarity	NPC262898
0.8182	Intermediate Similarity	NPC227582
0.8156	Intermediate Similarity	NPC55772
0.8156	Intermediate Similarity	NPC213468
0.8156	Intermediate Similarity	NPC248462
0.815	Intermediate Similarity	NPC155444
0.8131	Intermediate Similarity	NPC281049
0.8128	Intermediate Similarity	NPC179701
0.8128	Intermediate Similarity	NPC191382
0.8128	Intermediate Similarity	NPC56109
0.8118	Intermediate Similarity	NPC469763
0.8118	Intermediate Similarity	NPC73952
0.8118	Intermediate Similarity	NPC469760
0.8118	Intermediate Similarity	NPC469765
0.8118	Intermediate Similarity	NPC469786
0.8118	Intermediate Similarity	NPC25008
0.8118	Intermediate Similarity	NPC259644
0.8105	Intermediate Similarity	NPC300183
0.8101	Intermediate Similarity	NPC248454
0.8095	Intermediate Similarity	NPC474318
0.8095	Intermediate Similarity	NPC268744
0.8095	Intermediate Similarity	NPC153123
0.8095	Intermediate Similarity	NPC475914
0.8095	Intermediate Similarity	NPC220797
0.8095	Intermediate Similarity	NPC201266
0.8084	Intermediate Similarity	NPC314372
0.8081	Intermediate Similarity	NPC469762
0.8077	Intermediate Similarity	NPC477003
0.807	Intermediate Similarity	NPC70922
0.807	Intermediate Similarity	NPC212376
0.807	Intermediate Similarity	NPC80597
0.807	Intermediate Similarity	NPC211572
0.807	Intermediate Similarity	NPC75540
0.8063	Intermediate Similarity	NPC476073
0.8053	Intermediate Similarity	NPC77241
0.8053	Intermediate Similarity	NPC252338
0.8053	Intermediate Similarity	NPC269203
0.8053	Intermediate Similarity	NPC13456
0.8053	Intermediate Similarity	NPC166209
0.8035	Intermediate Similarity	NPC135141
0.8035	Intermediate Similarity	NPC92796
0.8034	Intermediate Similarity	NPC314603
0.803	Intermediate Similarity	NPC470731
0.803	Intermediate Similarity	NPC470732
0.8023	Intermediate Similarity	NPC469785
0.8022	Intermediate Similarity	NPC470205
0.8011	Intermediate Similarity	NPC16659
0.8011	Intermediate Similarity	NPC469896
0.801	Intermediate Similarity	NPC89987
0.8	Intermediate Similarity	NPC284775
0.7977	Intermediate Similarity	NPC299594
0.7967	Intermediate Similarity	NPC233936
0.7964	Intermediate Similarity	NPC190296
0.7956	Intermediate Similarity	NPC265710
0.795	Intermediate Similarity	NPC475736
0.7927	Intermediate Similarity	NPC317701
0.7923	Intermediate Similarity	NPC163055
0.7921	Intermediate Similarity	NPC194411
0.7919	Intermediate Similarity	NPC285469
0.7913	Intermediate Similarity	NPC326363
0.7913	Intermediate Similarity	NPC470729
0.7913	Intermediate Similarity	NPC477176
0.7913	Intermediate Similarity	NPC470730
0.7913	Intermediate Similarity	NPC477175
0.7907	Intermediate Similarity	NPC200214
0.7901	Intermediate Similarity	NPC240088
0.7901	Intermediate Similarity	NPC68354
0.7901	Intermediate Similarity	NPC473380
0.7898	Intermediate Similarity	NPC311276
0.7895	Intermediate Similarity	NPC105818
0.7895	Intermediate Similarity	NPC24678
0.7892	Intermediate Similarity	NPC315555
0.7889	Intermediate Similarity	NPC469938
0.7884	Intermediate Similarity	NPC195239
0.7884	Intermediate Similarity	NPC157828
0.7876	Intermediate Similarity	NPC476874
0.7874	Intermediate Similarity	NPC474877
0.7874	Intermediate Similarity	NPC477177
0.7874	Intermediate Similarity	NPC475969
0.7874	Intermediate Similarity	NPC475859
0.787	Intermediate Similarity	NPC470440
0.787	Intermediate Similarity	NPC159856
0.7869	Intermediate Similarity	NPC71037
0.7865	Intermediate Similarity	NPC205254
0.7865	Intermediate Similarity	NPC303820
0.7865	Intermediate Similarity	NPC106771
0.7865	Intermediate Similarity	NPC23420
0.7861	Intermediate Similarity	NPC303658
0.7853	Intermediate Similarity	NPC474389
0.7842	Intermediate Similarity	NPC11445
0.7837	Intermediate Similarity	NPC165743
0.7829	Intermediate Similarity	NPC230869
0.7828	Intermediate Similarity	NPC82370
0.7828	Intermediate Similarity	NPC54981
0.7824	Intermediate Similarity	NPC52909
0.7824	Intermediate Similarity	NPC475935
0.7824	Intermediate Similarity	NPC94211
0.7824	Intermediate Similarity	NPC288838
0.7819	Intermediate Similarity	NPC243716
0.7816	Intermediate Similarity	NPC476491
0.7812	Intermediate Similarity	NPC74413
0.7807	Intermediate Similarity	NPC175474
0.7799	Intermediate Similarity	NPC63279
0.7797	Intermediate Similarity	NPC271797
0.7797	Intermediate Similarity	NPC271734
0.7797	Intermediate Similarity	NPC21174
0.7797	Intermediate Similarity	NPC40779
0.7791	Intermediate Similarity	NPC53947
0.779	Intermediate Similarity	NPC37423
0.779	Intermediate Similarity	NPC275305
0.7789	Intermediate Similarity	NPC202812
0.7784	Intermediate Similarity	NPC73767
0.7778	Intermediate Similarity	NPC6982
0.7772	Intermediate Similarity	NPC315491
0.7772	Intermediate Similarity	NPC45459
0.7772	Intermediate Similarity	NPC473310
0.7767	Intermediate Similarity	NPC319232
0.7767	Intermediate Similarity	NPC24370
0.7762	Intermediate Similarity	NPC297642
0.7762	Intermediate Similarity	NPC325976
0.776	Intermediate Similarity	NPC67288
0.7756	Intermediate Similarity	NPC64216
0.7755	Intermediate Similarity	NPC471191
0.775	Intermediate Similarity	NPC229348
0.7742	Intermediate Similarity	NPC133003
0.774	Intermediate Similarity	NPC69843
0.774	Intermediate Similarity	NPC16667

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 NPC17059 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	520
0.2-0.3	1102
0.3-0.4	1700
0.4-0.5	2257
0.5-0.6	2249
0.6-0.7	920
0.7-0.8	160
0.8-0.85	24
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8721	High Similarity	NPD482	Approved
0.8689	High Similarity	NPD7621	Clinical (unspecified phase)
0.8663	High Similarity	NPD8493	Clinical (unspecified phase)
0.8636	High Similarity	NPD2095	Phase 2
0.8636	High Similarity	NPD2092	Phase 2
0.8636	High Similarity	NPD2094	Phase 2
0.8588	High Similarity	NPD2091	Phase 2
0.8588	High Similarity	NPD2096	Phase 2
0.8571	High Similarity	NPD7619	Phase 3
0.8571	High Similarity	NPD7618	Phase 3
0.8563	High Similarity	NPD749	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD750	Phase 2
0.8446	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD7970	Approved
0.8427	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD7470	Discontinued
0.8333	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.8306	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.829	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD3961	Discontinued
0.8238	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD6595	Phase 3
0.8201	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD5426	Phase 3
0.8168	Intermediate Similarity	NPD8272	Phase 2
0.8146	Intermediate Similarity	NPD4075	Phase 2
0.8128	Intermediate Similarity	NPD7781	Approved
0.8128	Intermediate Similarity	NPD7780	Approved
0.8125	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7944	Discontinued
0.8061	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.804	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.8033	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6217	Discontinued
0.7989	Intermediate Similarity	NPD6664	Approved
0.7956	Intermediate Similarity	NPD4076	Approved
0.7956	Intermediate Similarity	NPD4079	Approved
0.7917	Intermediate Similarity	NPD5017	Discontinued
0.7901	Intermediate Similarity	NPD3506	Approved
0.7901	Intermediate Similarity	NPD3505	Approved
0.7887	Intermediate Similarity	NPD5901	Discontinued
0.7879	Intermediate Similarity	NPD8093	Discontinued
0.7865	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD3100	Discontinued
0.7816	Intermediate Similarity	NPD7731	Approved
0.7816	Intermediate Similarity	NPD7730	Approved
0.7811	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7271	Approved
0.7802	Intermediate Similarity	NPD2144	Approved
0.7799	Intermediate Similarity	NPD7951	Approved
0.7799	Intermediate Similarity	NPD7789	Approved
0.7799	Intermediate Similarity	NPD7953	Approved
0.7799	Intermediate Similarity	NPD7790	Approved
0.7799	Intermediate Similarity	NPD7950	Approved
0.7799	Intermediate Similarity	NPD7791	Approved
0.7799	Intermediate Similarity	NPD7952	Approved
0.7796	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD4128	Approved
0.779	Intermediate Similarity	NPD5065	Approved
0.7784	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD786	Approved
0.7778	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD484	Approved
0.7755	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7824	Approved
0.7733	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1722	Approved
0.7688	Intermediate Similarity	NPD2172	Phase 1
0.7681	Intermediate Similarity	NPD7711	Discontinued
0.7681	Intermediate Similarity	NPD7603	Discontinued
0.7676	Intermediate Similarity	NPD3038	Discontinued
0.766	Intermediate Similarity	NPD8431	Approved
0.766	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD6999	Discontinued
0.7626	Intermediate Similarity	NPD8322	Phase 2
0.7617	Intermediate Similarity	NPD2880	Discontinued
0.7598	Intermediate Similarity	NPD3583	Phase 2
0.7592	Intermediate Similarity	NPD6665	Discontinued
0.7588	Intermediate Similarity	NPD7665	Phase 2
0.7588	Intermediate Similarity	NPD7666	Phase 3
0.7576	Intermediate Similarity	NPD7001	Phase 3
0.7574	Intermediate Similarity	NPD8094	Discontinued
0.7569	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2639	Approved
0.7514	Intermediate Similarity	NPD4181	Approved
0.7514	Intermediate Similarity	NPD2642	Approved
0.7513	Intermediate Similarity	NPD8073	Approved
0.75	Intermediate Similarity	NPD4922	Phase 2
0.75	Intermediate Similarity	NPD7564	Discontinued
0.7487	Intermediate Similarity	NPD4499	Approved
0.7487	Intermediate Similarity	NPD7957	Phase 1
0.7487	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD8072	Approved
0.7474	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4848	Phase 1
0.7473	Intermediate Similarity	NPD4638	Approved
0.7473	Intermediate Similarity	NPD4640	Approved
0.7473	Intermediate Similarity	NPD4639	Approved
0.7461	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7716	Approved
0.7416	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7717	Approved
0.7413	Intermediate Similarity	NPD2509	Approved
0.7413	Intermediate Similarity	NPD2442	Approved
0.7413	Intermediate Similarity	NPD2443	Approved
0.7413	Intermediate Similarity	NPD2510	Approved
0.7411	Intermediate Similarity	NPD4601	Approved
0.7411	Intermediate Similarity	NPD4600	Approved
0.7407	Intermediate Similarity	NPD6178	Phase 3
0.7405	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD2837	Discontinued
0.74	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3178	Discontinued
0.7393	Intermediate Similarity	NPD6164	Phase 2
0.7393	Intermediate Similarity	NPD6165	Phase 2
0.7389	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4463	Approved
0.7386	Intermediate Similarity	NPD4462	Approved
0.7382	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5818	Discontinued
0.7377	Intermediate Similarity	NPD2844	Phase 3
0.7366	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD3319	Phase 1
0.7354	Intermediate Similarity	NPD3318	Approved
0.7354	Intermediate Similarity	NPD3320	Approved
0.7347	Intermediate Similarity	NPD7948	Phase 1
0.7323	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5505	Discontinued
0.7313	Intermediate Similarity	NPD2008	Discontinued
0.7308	Intermediate Similarity	NPD3323	Discontinued
0.7295	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2511	Approved
0.7293	Intermediate Similarity	NPD1404	Approved
0.7293	Intermediate Similarity	NPD1403	Approved
0.7287	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6368	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2641	Approved
0.7283	Intermediate Similarity	NPD2640	Approved
0.7268	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5106	Approved
0.7263	Intermediate Similarity	NPD5105	Approved
0.726	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6771	Discontinued
0.7251	Intermediate Similarity	NPD200	Phase 2
0.7251	Intermediate Similarity	NPD201	Phase 2
0.7245	Intermediate Similarity	NPD4602	Approved
0.7243	Intermediate Similarity	NPD1326	Approved
0.7243	Intermediate Similarity	NPD1325	Approved
0.7241	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7026	Phase 2
0.7236	Intermediate Similarity	NPD4501	Approved
0.7236	Intermediate Similarity	NPD4500	Approved
0.7233	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1096	Discontinued
0.7225	Intermediate Similarity	NPD7483	Phase 2
0.7225	Intermediate Similarity	NPD7482	Phase 2
0.7209	Intermediate Similarity	NPD2896	Discontinued
0.7206	Intermediate Similarity	NPD2408	Discontinued
0.7204	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6249	Phase 2
0.7186	Intermediate Similarity	NPD6248	Phase 2
0.7184	Intermediate Similarity	NPD4852	Phase 2
0.7184	Intermediate Similarity	NPD2411	Approved
0.7181	Intermediate Similarity	NPD6044	Discontinued
0.7181	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4703	Approved
0.7175	Intermediate Similarity	NPD1661	Suspended
0.7175	Intermediate Similarity	NPD4702	Approved
0.717	Intermediate Similarity	NPD6173	Approved
0.7165	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5400	Approved
0.7157	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5809	Phase 3
0.7143	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5199	Approved
0.7143	Intermediate Similarity	NPD5198	Approved
0.7135	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD8257	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