NPASS Compound

Structure

NPC16352 OpenBabel07101718322D 30 34 0 0 0 0 0 0 0 0999 V2000 -5.7918 1.0191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0487 1.6882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5839 0.0409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0976 1.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2316 -1.0771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -4.0827 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 -4.6328 -0.2681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2261 -1.1816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 -3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8897 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7261 -2.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3194 -2.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7206 -2.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0625 -3.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0237 -0.0990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 -3.9781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.9285 -3.1303 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.3898 -1.4091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9580 -4.6249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 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 -1.0000 0.0000 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 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 11 2 0 0 0 0 4 15 2 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 21 1 0 0 0 0 9 14 2 0 0 0 0 9 22 1 0 0 0 0 10 29 1 0 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 20 25 2 0 0 0 0 26 30 1 0 0 0 0 27 30 2 0 0 0 0 28 30 2 0 0 0 0 29 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	423.05
Volume:	386.933
LogP:	1.364
LogD:	1.604
LogS:	-2.6
# Rotatable Bonds:	4
TPSA:	141.35
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.293
Synthetic Accessibility Score:	2.704
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.511
MDCK Permeability:	8.01555324869696e-06
Pgp-inhibitor:	0.058
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.222
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	99.6558837890625%
Volume Distribution (VD):	0.378
Pgp-substrate:	0.5464080572128296%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.175
CYP2C19-inhibitor:	0.329
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.385
CYP2C9-substrate:	0.976
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.302
CYP3A4-inhibitor:	0.836
CYP3A4-substrate:	0.053

ADMET: Excretion

Clearance (CL):	0.911
Half-life (T1/2):	0.246

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.944
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.605
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.078
Carcinogencity:	0.53
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.713

Download Data

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

Natural Product: NPC16352

Natural Product ID:	NPC16352
*Common Name:**	Arcyroxocin B-6-O-Sulfate
IUPAC Name:	[3-[4-(1H-indol-3-yl)-2,5-dioxopyrrol-3-yl]-1H-indol-6-yl] hydrogen sulfate
Synonyms:
Standard InCHIKey:	NGBRFUYDUQHTFT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H13N3O6S/c24-19-17(13-8-21-15-4-2-1-3-11(13)15)18(20(25)23-19)14-9-22-16-7-10(5-6-12(14)16)29-30(26,27)28/h1-9,21-22H,(H,23,24,25)(H,26,27,28)
SMILES:	O=C1N=C(C(=C1c1c[nH]c2c1ccc(c2)OS(=O)(=O)O)c1c[nH]c2c1cccc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498126
PubChem CID:	16083195
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000403] Organic sulfuric acids and derivatives [CHEMONTID:0004258] Arylsulfates

*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
NPO32752	Arcyria obvelata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO10376	Arcyria denudata	Species	Trichiidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[448115]

☑ 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 NPC16352 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	485
0.1-0.2	3763
0.2-0.3	13259
0.3-0.4	13659
0.4-0.5	6666
0.5-0.6	2427
0.6-0.7	1911
0.7-0.8	503
0.8-0.85	20
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC264285
0.8883	High Similarity	NPC131887
0.8813	High Similarity	NPC78609
0.8578	High Similarity	NPC276657
0.8356	Intermediate Similarity	NPC178858
0.8341	Intermediate Similarity	NPC476073
0.8333	Intermediate Similarity	NPC46580
0.8273	Intermediate Similarity	NPC132329
0.8269	Intermediate Similarity	NPC183777
0.8244	Intermediate Similarity	NPC213308
0.8235	Intermediate Similarity	NPC67288
0.8199	Intermediate Similarity	NPC82370
0.8186	Intermediate Similarity	NPC227582
0.8125	Intermediate Similarity	NPC15801
0.8117	Intermediate Similarity	NPC325976
0.8111	Intermediate Similarity	NPC60621
0.81	Intermediate Similarity	NPC326363
0.8098	Intermediate Similarity	NPC77555
0.8082	Intermediate Similarity	NPC476818
0.8079	Intermediate Similarity	NPC99666
0.8068	Intermediate Similarity	NPC252338
0.8027	Intermediate Similarity	NPC207686
0.7991	Intermediate Similarity	NPC110182
0.7981	Intermediate Similarity	NPC315491
0.7981	Intermediate Similarity	NPC45459
0.7971	Intermediate Similarity	NPC306376
0.7965	Intermediate Similarity	NPC235685
0.7965	Intermediate Similarity	NPC91868
0.7965	Intermediate Similarity	NPC63971
0.7962	Intermediate Similarity	NPC175602
0.7933	Intermediate Similarity	NPC74413
0.793	Intermediate Similarity	NPC101350
0.7929	Intermediate Similarity	NPC96890
0.7913	Intermediate Similarity	NPC160898
0.7905	Intermediate Similarity	NPC260900
0.7883	Intermediate Similarity	NPC319232
0.7883	Intermediate Similarity	NPC24370
0.7867	Intermediate Similarity	NPC134848
0.7854	Intermediate Similarity	NPC269270
0.785	Intermediate Similarity	NPC61038
0.7844	Intermediate Similarity	NPC27041
0.7844	Intermediate Similarity	NPC472285
0.784	Intermediate Similarity	NPC270918
0.784	Intermediate Similarity	NPC88008
0.7837	Intermediate Similarity	NPC156704
0.7824	Intermediate Similarity	NPC219087
0.7818	Intermediate Similarity	NPC14686
0.7816	Intermediate Similarity	NPC324149
0.7812	Intermediate Similarity	NPC194740
0.7808	Intermediate Similarity	NPC303658
0.7806	Intermediate Similarity	NPC63109
0.7804	Intermediate Similarity	NPC210828
0.7804	Intermediate Similarity	NPC39679
0.7804	Intermediate Similarity	NPC86834
0.7804	Intermediate Similarity	NPC171787
0.7798	Intermediate Similarity	NPC170114
0.7793	Intermediate Similarity	NPC229893
0.7788	Intermediate Similarity	NPC242209
0.7783	Intermediate Similarity	NPC314002
0.7783	Intermediate Similarity	NPC53144
0.7778	Intermediate Similarity	NPC23294
0.7772	Intermediate Similarity	NPC220765
0.7756	Intermediate Similarity	NPC321708
0.7752	Intermediate Similarity	NPC474412
0.7752	Intermediate Similarity	NPC470549
0.775	Intermediate Similarity	NPC111275
0.7742	Intermediate Similarity	NPC294620
0.774	Intermediate Similarity	NPC326634
0.7734	Intermediate Similarity	NPC204717
0.7731	Intermediate Similarity	NPC303951
0.7731	Intermediate Similarity	NPC475746
0.7717	Intermediate Similarity	NPC36405
0.7713	Intermediate Similarity	NPC122436
0.7711	Intermediate Similarity	NPC72980
0.7706	Intermediate Similarity	NPC207866
0.7696	Intermediate Similarity	NPC87413
0.7692	Intermediate Similarity	NPC106937
0.7692	Intermediate Similarity	NPC213530
0.7692	Intermediate Similarity	NPC193267
0.7675	Intermediate Similarity	NPC323752
0.7664	Intermediate Similarity	NPC285558
0.7659	Intermediate Similarity	NPC171171
0.7656	Intermediate Similarity	NPC276517
0.7652	Intermediate Similarity	NPC28945
0.7637	Intermediate Similarity	NPC153400
0.7636	Intermediate Similarity	NPC330009
0.7636	Intermediate Similarity	NPC322064
0.7633	Intermediate Similarity	NPC83111
0.7626	Intermediate Similarity	NPC477610
0.7626	Intermediate Similarity	NPC31700
0.7624	Intermediate Similarity	NPC42979
0.7623	Intermediate Similarity	NPC473317
0.7621	Intermediate Similarity	NPC278434
0.7617	Intermediate Similarity	NPC200836
0.7613	Intermediate Similarity	NPC74360
0.7609	Intermediate Similarity	NPC477549
0.7602	Intermediate Similarity	NPC305984
0.76	Intermediate Similarity	NPC474409
0.7589	Intermediate Similarity	NPC220851
0.7581	Intermediate Similarity	NPC475070
0.7581	Intermediate Similarity	NPC470500
0.7574	Intermediate Similarity	NPC184964
0.7569	Intermediate Similarity	NPC85273
0.7569	Intermediate Similarity	NPC11464
0.7569	Intermediate Similarity	NPC5145
0.7557	Intermediate Similarity	NPC3207
0.7545	Intermediate Similarity	NPC282247
0.7537	Intermediate Similarity	NPC55772
0.7535	Intermediate Similarity	NPC476098
0.7532	Intermediate Similarity	NPC473187
0.7525	Intermediate Similarity	NPC224764
0.7524	Intermediate Similarity	NPC94943
0.7523	Intermediate Similarity	NPC232727
0.7522	Intermediate Similarity	NPC125597
0.7522	Intermediate Similarity	NPC70155
0.7522	Intermediate Similarity	NPC220852
0.7512	Intermediate Similarity	NPC476460
0.7512	Intermediate Similarity	NPC212535
0.7512	Intermediate Similarity	NPC4687
0.7512	Intermediate Similarity	NPC249583
0.7511	Intermediate Similarity	NPC237740
0.7511	Intermediate Similarity	NPC260434
0.75	Intermediate Similarity	NPC150239
0.75	Intermediate Similarity	NPC12344
0.75	Intermediate Similarity	NPC285343
0.75	Intermediate Similarity	NPC174760
0.75	Intermediate Similarity	NPC74153
0.7489	Intermediate Similarity	NPC167860
0.7489	Intermediate Similarity	NPC123976
0.7489	Intermediate Similarity	NPC247803
0.7488	Intermediate Similarity	NPC62749
0.7477	Intermediate Similarity	NPC204491
0.7477	Intermediate Similarity	NPC203614
0.7476	Intermediate Similarity	NPC190007
0.7468	Intermediate Similarity	NPC470784
0.7466	Intermediate Similarity	NPC266931
0.7464	Intermediate Similarity	NPC154339
0.7462	Intermediate Similarity	NPC131718
0.745	Intermediate Similarity	NPC78020
0.7447	Intermediate Similarity	NPC171393
0.7447	Intermediate Similarity	NPC295452
0.7444	Intermediate Similarity	NPC304926
0.7444	Intermediate Similarity	NPC476041
0.7443	Intermediate Similarity	NPC271862
0.7442	Intermediate Similarity	NPC300183
0.7441	Intermediate Similarity	NPC473821
0.7436	Intermediate Similarity	NPC477861
0.7425	Intermediate Similarity	NPC184680
0.7425	Intermediate Similarity	NPC184225
0.7421	Intermediate Similarity	NPC316981
0.7415	Intermediate Similarity	NPC271792
0.7411	Intermediate Similarity	NPC477609
0.7409	Intermediate Similarity	NPC309845
0.7407	Intermediate Similarity	NPC74619
0.7407	Intermediate Similarity	NPC211813
0.7404	Intermediate Similarity	NPC315555
0.7403	Intermediate Similarity	NPC279189
0.7403	Intermediate Similarity	NPC196718
0.7403	Intermediate Similarity	NPC200553
0.7402	Intermediate Similarity	NPC59269
0.74	Intermediate Similarity	NPC77101
0.7397	Intermediate Similarity	NPC127677
0.7397	Intermediate Similarity	NPC258062
0.7393	Intermediate Similarity	NPC41679
0.7393	Intermediate Similarity	NPC470785
0.7389	Intermediate Similarity	NPC149155
0.7389	Intermediate Similarity	NPC203468
0.7389	Intermediate Similarity	NPC110500
0.7386	Intermediate Similarity	NPC314882
0.7376	Intermediate Similarity	NPC9894
0.7373	Intermediate Similarity	NPC98715
0.7371	Intermediate Similarity	NPC13880
0.7371	Intermediate Similarity	NPC11445
0.7371	Intermediate Similarity	NPC251090
0.7368	Intermediate Similarity	NPC17059
0.7366	Intermediate Similarity	NPC283219
0.7366	Intermediate Similarity	NPC169402
0.7364	Intermediate Similarity	NPC325297
0.7358	Intermediate Similarity	NPC307963
0.7358	Intermediate Similarity	NPC267343
0.7356	Intermediate Similarity	NPC15102
0.7356	Intermediate Similarity	NPC99939
0.7356	Intermediate Similarity	NPC308931
0.7354	Intermediate Similarity	NPC478157
0.7353	Intermediate Similarity	NPC267885
0.7352	Intermediate Similarity	NPC225821
0.7352	Intermediate Similarity	NPC46225
0.7342	Intermediate Similarity	NPC310211
0.7342	Intermediate Similarity	NPC308137
0.7342	Intermediate Similarity	NPC151976
0.7342	Intermediate Similarity	NPC87856
0.7336	Intermediate Similarity	NPC153042
0.7333	Intermediate Similarity	NPC32771
0.7328	Intermediate Similarity	NPC102593
0.7328	Intermediate Similarity	NPC63031
0.7327	Intermediate Similarity	NPC193761
0.7325	Intermediate Similarity	NPC130570
0.7325	Intermediate Similarity	NPC147446
0.7324	Intermediate Similarity	NPC157828
0.7324	Intermediate Similarity	NPC195239

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 NPC16352 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	645
0.2-0.3	884
0.3-0.4	1553
0.4-0.5	2760
0.5-0.6	2087
0.6-0.7	865
0.7-0.8	91
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD5426	Phase 3
0.8134	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6999	Discontinued
0.8056	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.8048	Intermediate Similarity	NPD7001	Phase 3
0.801	Intermediate Similarity	NPD7948	Phase 1
0.7981	Intermediate Similarity	NPD484	Approved
0.783	Intermediate Similarity	NPD5901	Discontinued
0.7804	Intermediate Similarity	NPD7665	Phase 2
0.7804	Intermediate Similarity	NPD7666	Phase 3
0.7803	Intermediate Similarity	NPD7603	Discontinued
0.7778	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4852	Phase 2
0.7692	Intermediate Similarity	NPD802	Phase 2
0.7689	Intermediate Similarity	NPD4845	Discontinued
0.7639	Intermediate Similarity	NPD2916	Discontinued
0.7598	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6242	Discontinued
0.7534	Intermediate Similarity	NPD7470	Discontinued
0.7533	Intermediate Similarity	NPD6164	Phase 2
0.7533	Intermediate Similarity	NPD6165	Phase 2
0.7521	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD3746	Discontinued
0.7476	Intermediate Similarity	NPD2091	Phase 2
0.7476	Intermediate Similarity	NPD2096	Phase 2
0.744	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD2095	Phase 2
0.7427	Intermediate Similarity	NPD2094	Phase 2
0.7427	Intermediate Similarity	NPD2092	Phase 2
0.7406	Intermediate Similarity	NPD5482	Discontinued
0.7399	Intermediate Similarity	NPD5612	Discontinued
0.7391	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD482	Approved
0.7371	Intermediate Similarity	NPD7558	Phase 2
0.7358	Intermediate Similarity	NPD1038	Approved
0.7353	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD8395	Approved
0.7349	Intermediate Similarity	NPD8396	Approved
0.7342	Intermediate Similarity	NPD8093	Discontinued
0.733	Intermediate Similarity	NPD6595	Phase 3
0.7318	Intermediate Similarity	NPD2510	Approved
0.7318	Intermediate Similarity	NPD2509	Approved
0.7311	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD8094	Discontinued
0.7306	Intermediate Similarity	NPD6530	Approved
0.7306	Intermediate Similarity	NPD6531	Approved
0.7304	Intermediate Similarity	NPD5065	Approved
0.7297	Intermediate Similarity	NPD8349	Phase 1
0.7283	Intermediate Similarity	NPD7181	Phase 3
0.7277	Intermediate Similarity	NPD2844	Phase 3
0.7258	Intermediate Similarity	NPD8284	Discontinued
0.7257	Intermediate Similarity	NPD6790	Phase 1
0.7252	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6995	Phase 1
0.7196	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2781	Approved
0.7189	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5632	Approved
0.7181	Intermediate Similarity	NPD3354	Phase 2
0.7177	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD8091	Phase 3
0.7149	Intermediate Similarity	NPD4373	Phase 2
0.7136	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1392	Approved
0.7117	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8097	Phase 3
0.7111	Intermediate Similarity	NPD8096	Phase 3
0.7109	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7106	Intermediate Similarity	NPD4885	Approved
0.7104	Intermediate Similarity	NPD8098	Approved
0.7103	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD2782	Approved
0.7094	Intermediate Similarity	NPD4952	Phase 3
0.7094	Intermediate Similarity	NPD2780	Approved
0.7087	Intermediate Similarity	NPD750	Phase 2
0.708	Intermediate Similarity	NPD6456	Discontinued
0.708	Intermediate Similarity	NPD3243	Approved
0.7072	Intermediate Similarity	NPD3003	Approved
0.7061	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5450	Discontinued
0.7049	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4948	Discontinued
0.7032	Intermediate Similarity	NPD3825	Phase 3
0.7032	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3947	Discontinued
0.7022	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5658	Approved
0.7009	Intermediate Similarity	NPD6376	Discontinued
0.7008	Intermediate Similarity	NPD4558	Phase 2
0.7	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD8403	Phase 1
0.6996	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6665	Discontinued
0.699	Remote Similarity	NPD1325	Approved
0.699	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.699	Remote Similarity	NPD1326	Approved
0.6986	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7946	Pre-registration
0.6983	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5902	Approved
0.6974	Remote Similarity	NPD5903	Approved
0.6968	Remote Similarity	NPD4511	Phase 1
0.6967	Remote Similarity	NPD3178	Discontinued
0.6966	Remote Similarity	NPD7426	Phase 1
0.6964	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.696	Remote Similarity	NPD3330	Phase 1
0.696	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD3814	Phase 1
0.6951	Remote Similarity	NPD6987	Phase 1
0.6946	Remote Similarity	NPD3006	Discontinued
0.6944	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3394	Approved
0.6943	Remote Similarity	NPD3393	Approved
0.6943	Remote Similarity	NPD3389	Approved
0.6937	Remote Similarity	NPD8073	Approved
0.6936	Remote Similarity	NPD3259	Approved
0.6933	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.692	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5067	Phase 2
0.6916	Remote Similarity	NPD5066	Phase 2
0.6901	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7711	Discontinued
0.6891	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8431	Approved
0.6883	Remote Similarity	NPD4429	Discontinued
0.6881	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD8512	Phase 3
0.6875	Remote Similarity	NPD4795	Phase 2
0.6864	Remote Similarity	NPD5003	Discontinued
0.6861	Remote Similarity	NPD6975	Discontinued
0.686	Remote Similarity	NPD8016	Phase 3
0.686	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3258	Approved
0.6849	Remote Similarity	NPD7688	Phase 1
0.6849	Remote Similarity	NPD7944	Discontinued
0.6846	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.684	Remote Similarity	NPD5818	Discontinued
0.6837	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5559	Phase 2
0.6835	Remote Similarity	NPD3404	Approved
0.6833	Remote Similarity	NPD6963	Approved
0.6833	Remote Similarity	NPD6964	Approved
0.683	Remote Similarity	NPD8072	Approved
0.6826	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7970	Approved
0.6826	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7069	Discontinued
0.681	Remote Similarity	NPD7878	Phase 2
0.6803	Remote Similarity	NPD6517	Phase 3
0.6803	Remote Similarity	NPD6716	Phase 1
0.6802	Remote Similarity	NPD1768	Approved
0.68	Remote Similarity	NPD8283	Approved
0.68	Remote Similarity	NPD56	Approved
0.68	Remote Similarity	NPD8282	Approved
0.6797	Remote Similarity	NPD8160	Phase 2
0.6796	Remote Similarity	NPD5138	Approved
0.6796	Remote Similarity	NPD5140	Approved
0.6792	Remote Similarity	NPD6494	Phase 2
0.6792	Remote Similarity	NPD7951	Approved
0.6792	Remote Similarity	NPD7790	Approved
0.6792	Remote Similarity	NPD7950	Approved
0.6792	Remote Similarity	NPD7953	Approved
0.6792	Remote Similarity	NPD7789	Approved
0.6792	Remote Similarity	NPD7791	Approved
0.6792	Remote Similarity	NPD7952	Approved
0.6792	Remote Similarity	NPD4850	Phase 1
0.6784	Remote Similarity	NPD2189	Approved
0.6784	Remote Similarity	NPD2187	Approved
0.6779	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3809	Discontinued
0.6773	Remote Similarity	NPD7618	Phase 3
0.6773	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD7619	Phase 3
0.6773	Remote Similarity	NPD4418	Discontinued
0.6771	Remote Similarity	NPD1739	Approved
0.6771	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD1740	Approved
0.677	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8364	Approved
0.677	Remote Similarity	NPD7957	Phase 1
0.677	Remote Similarity	NPD8363	Approved
0.6769	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7710	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