NPASS Compound

Structure

NPC276657 OpenBabel07101718182D 24 27 0 0 0 0 0 0 0 0999 V2000 -4.9399 -1.9293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3521 -1.1203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5386 -2.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7484 -1.0557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5331 -2.8429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9508 -2.1384 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 -1.9563 -2.0339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3576 -1.2248 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 -1.2872 -2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6144 -0.5557 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 -5.1209 -3.6519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 -3.7281 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 9 1 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 7 19 1 0 0 0 0 8 14 2 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 15 2 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 19 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 23 2 0 0 0 0 18 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.08
Volume:	316.448
LogP:	2.9
LogD:	2.553
LogS:	-5.096
# Rotatable Bonds:	3
TPSA:	106.18
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	2.503
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.224
MDCK Permeability:	5.25510677107377e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.049
20% Bioavailability (F20%):	0.331
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	98.9649887084961%
Volume Distribution (VD):	0.494
Pgp-substrate:	2.3856141567230225%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.905
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.775
CYP2C9-substrate:	0.968
CYP2D6-inhibitor:	0.839
CYP2D6-substrate:	0.831
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	9.517
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.328
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.881
Rat Oral Acute Toxicity:	0.889
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.876
Carcinogencity:	0.088
Eye Corrosion:	0.004
Eye Irritation:	0.925
Respiratory Toxicity:	0.079

Download Data

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

Natural Product: NPC276657

Natural Product ID:	NPC276657
*Common Name:**	Hyrtiosin B
IUPAC Name:	1,2-bis(5-hydroxy-1H-indol-3-yl)ethane-1,2-dione
Synonyms:
Standard InCHIKey:	URWBQCGXPJSAQI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12N2O4/c21-9-1-3-15-11(5-9)13(7-19-15)17(23)18(24)14-8-20-16-4-2-10(22)6-12(14)16/h1-8,19-22H
SMILES:	O=C(c1c[nH]c2c1cc(O)cc2)C(=O)c1c[nH]c2c1cc(O)cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459354
PubChem CID:	638389
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0004162] Hydroxyindoles

*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
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514320]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497952]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17378531]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19167886]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19783432]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	Australian	n.a.	PMID[24973030]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28834433]

☑ 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	1

Activity Type	# Activity
Individual Protein	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	89000.0	nM	PMID[544701]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	89000.0	nM	PMID[544702]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	29.0	ug.mL-1	PMID[544702]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	100.0	ug.mL-1	PMID[544702]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	624400.0	nM	PMID[544701]

☑ 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 NPC276657 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	578
0.1-0.2	3715
0.2-0.3	13260
0.3-0.4	7940
0.4-0.5	12471
0.5-0.6	2042
0.6-0.7	2109
0.7-0.8	525
0.8-0.85	47
0.85-0.9	6
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC207686
0.9055	High Similarity	NPC219087
0.9045	High Similarity	NPC171787
0.8767	High Similarity	NPC178858
0.8744	High Similarity	NPC264285
0.8702	High Similarity	NPC74360
0.8693	High Similarity	NPC213308
0.8618	High Similarity	NPC15801
0.8606	High Similarity	NPC27041
0.8578	High Similarity	NPC16352
0.8507	High Similarity	NPC45459
0.8507	High Similarity	NPC315491
0.8502	High Similarity	NPC110182
0.8434	Intermediate Similarity	NPC99666
0.8408	Intermediate Similarity	NPC131887
0.8402	Intermediate Similarity	NPC477549
0.8364	Intermediate Similarity	NPC229893
0.8358	Intermediate Similarity	NPC227582
0.8358	Intermediate Similarity	NPC156704
0.8358	Intermediate Similarity	NPC77555
0.835	Intermediate Similarity	NPC183777
0.8316	Intermediate Similarity	NPC314002
0.8308	Intermediate Similarity	NPC220765
0.8304	Intermediate Similarity	NPC74619
0.8278	Intermediate Similarity	NPC82370
0.8265	Intermediate Similarity	NPC204717
0.8263	Intermediate Similarity	NPC269270
0.8261	Intermediate Similarity	NPC88008
0.8261	Intermediate Similarity	NPC270918
0.8235	Intermediate Similarity	NPC252338
0.823	Intermediate Similarity	NPC309845
0.8224	Intermediate Similarity	NPC14686
0.8213	Intermediate Similarity	NPC175602
0.8182	Intermediate Similarity	NPC171171
0.8157	Intermediate Similarity	NPC476818
0.8141	Intermediate Similarity	NPC278434
0.8108	Intermediate Similarity	NPC97902
0.8103	Intermediate Similarity	NPC184964
0.81	Intermediate Similarity	NPC279189
0.81	Intermediate Similarity	NPC200553
0.8098	Intermediate Similarity	NPC74413
0.8095	Intermediate Similarity	NPC61038
0.8079	Intermediate Similarity	NPC276517
0.806	Intermediate Similarity	NPC154339
0.8049	Intermediate Similarity	NPC67288
0.8037	Intermediate Similarity	NPC322064
0.8036	Intermediate Similarity	NPC235685
0.8035	Intermediate Similarity	NPC91868
0.8035	Intermediate Similarity	NPC63971
0.8028	Intermediate Similarity	NPC477610
0.802	Intermediate Similarity	NPC476460
0.8019	Intermediate Similarity	NPC9894
0.8	Intermediate Similarity	NPC472285
0.8	Intermediate Similarity	NPC469727
0.8	Intermediate Similarity	NPC90229
0.8	Intermediate Similarity	NPC101350
0.7991	Intermediate Similarity	NPC216369
0.7991	Intermediate Similarity	NPC162002
0.799	Intermediate Similarity	NPC475070
0.7982	Intermediate Similarity	NPC78609
0.7981	Intermediate Similarity	NPC260900
0.7946	Intermediate Similarity	NPC174489
0.7944	Intermediate Similarity	NPC207866
0.7943	Intermediate Similarity	NPC476098
0.7943	Intermediate Similarity	NPC134848
0.7941	Intermediate Similarity	NPC267343
0.7934	Intermediate Similarity	NPC294375
0.7919	Intermediate Similarity	NPC284775
0.7895	Intermediate Similarity	NPC476073
0.7892	Intermediate Similarity	NPC477112
0.7887	Intermediate Similarity	NPC5145
0.7882	Intermediate Similarity	NPC83111
0.788	Intermediate Similarity	NPC477609
0.7876	Intermediate Similarity	NPC26641
0.7872	Intermediate Similarity	NPC63109
0.7871	Intermediate Similarity	NPC46580
0.7854	Intermediate Similarity	NPC304203
0.7848	Intermediate Similarity	NPC326363
0.7841	Intermediate Similarity	NPC41679
0.7834	Intermediate Similarity	NPC476041
0.7834	Intermediate Similarity	NPC304926
0.7833	Intermediate Similarity	NPC321708
0.7826	Intermediate Similarity	NPC74153
0.7817	Intermediate Similarity	NPC171393
0.7817	Intermediate Similarity	NPC295452
0.7816	Intermediate Similarity	NPC202812
0.7807	Intermediate Similarity	NPC37152
0.7805	Intermediate Similarity	NPC324149
0.7788	Intermediate Similarity	NPC182222
0.7788	Intermediate Similarity	NPC325976
0.7788	Intermediate Similarity	NPC36405
0.7783	Intermediate Similarity	NPC130570
0.7778	Intermediate Similarity	NPC266931
0.7767	Intermediate Similarity	NPC473821
0.7767	Intermediate Similarity	NPC307963
0.7758	Intermediate Similarity	NPC478078
0.7756	Intermediate Similarity	NPC138370
0.7746	Intermediate Similarity	NPC193238
0.7746	Intermediate Similarity	NPC283117
0.7742	Intermediate Similarity	NPC474412
0.7739	Intermediate Similarity	NPC111275
0.7725	Intermediate Similarity	NPC211813
0.7722	Intermediate Similarity	NPC258048
0.7706	Intermediate Similarity	NPC469928
0.7703	Intermediate Similarity	NPC122436
0.77	Intermediate Similarity	NPC55772
0.77	Intermediate Similarity	NPC300156
0.77	Intermediate Similarity	NPC45190
0.7699	Intermediate Similarity	NPC196718
0.7692	Intermediate Similarity	NPC251090
0.7681	Intermediate Similarity	NPC326422
0.7679	Intermediate Similarity	NPC53534
0.7672	Intermediate Similarity	NPC208522
0.7664	Intermediate Similarity	NPC53344
0.7661	Intermediate Similarity	NPC237740
0.7659	Intermediate Similarity	NPC221873
0.7659	Intermediate Similarity	NPC296527
0.7659	Intermediate Similarity	NPC32771
0.7658	Intermediate Similarity	NPC220851
0.765	Intermediate Similarity	NPC12344
0.7644	Intermediate Similarity	NPC326634
0.7634	Intermediate Similarity	NPC319232
0.7634	Intermediate Similarity	NPC24370
0.7628	Intermediate Similarity	NPC86834
0.7628	Intermediate Similarity	NPC210828
0.7628	Intermediate Similarity	NPC39679
0.7621	Intermediate Similarity	NPC132329
0.7621	Intermediate Similarity	NPC102593
0.7621	Intermediate Similarity	NPC76748
0.7619	Intermediate Similarity	NPC474916
0.7613	Intermediate Similarity	NPC473317
0.7613	Intermediate Similarity	NPC60621
0.7612	Intermediate Similarity	NPC88363
0.7604	Intermediate Similarity	NPC23294
0.7597	Intermediate Similarity	NPC160898
0.7594	Intermediate Similarity	NPC471944
0.7588	Intermediate Similarity	NPC70155
0.7585	Intermediate Similarity	NPC92111
0.7581	Intermediate Similarity	NPC321428
0.758	Intermediate Similarity	NPC118228
0.7571	Intermediate Similarity	NPC473814
0.7571	Intermediate Similarity	NPC78767
0.7566	Intermediate Similarity	NPC477607
0.7566	Intermediate Similarity	NPC477608
0.7562	Intermediate Similarity	NPC152620
0.7558	Intermediate Similarity	NPC303951
0.7555	Intermediate Similarity	NPC39370
0.7549	Intermediate Similarity	NPC477003
0.7544	Intermediate Similarity	NPC473186
0.7536	Intermediate Similarity	NPC192315
0.7536	Intermediate Similarity	NPC306376
0.7525	Intermediate Similarity	NPC78020
0.7524	Intermediate Similarity	NPC222018
0.7524	Intermediate Similarity	NPC242209
0.7523	Intermediate Similarity	NPC317701
0.7522	Intermediate Similarity	NPC473187
0.7522	Intermediate Similarity	NPC157931
0.7512	Intermediate Similarity	NPC325297
0.7512	Intermediate Similarity	NPC476116
0.7511	Intermediate Similarity	NPC473312
0.7511	Intermediate Similarity	NPC125597
0.7511	Intermediate Similarity	NPC293151
0.75	Intermediate Similarity	NPC476167
0.75	Intermediate Similarity	NPC475746
0.7489	Intermediate Similarity	NPC184225
0.7489	Intermediate Similarity	NPC323969
0.7488	Intermediate Similarity	NPC470500
0.7476	Intermediate Similarity	NPC62749
0.7476	Intermediate Similarity	NPC93390
0.7476	Intermediate Similarity	NPC146724
0.7475	Intermediate Similarity	NPC59269
0.7475	Intermediate Similarity	NPC96890
0.7468	Intermediate Similarity	NPC148889
0.7466	Intermediate Similarity	NPC203614
0.7466	Intermediate Similarity	NPC204491
0.7465	Intermediate Similarity	NPC176538
0.7465	Intermediate Similarity	NPC127677
0.7465	Intermediate Similarity	NPC258062
0.7463	Intermediate Similarity	NPC203468
0.7463	Intermediate Similarity	NPC149155
0.7463	Intermediate Similarity	NPC110500
0.746	Intermediate Similarity	NPC77101
0.7449	Intermediate Similarity	NPC131718
0.7445	Intermediate Similarity	NPC6215
0.7443	Intermediate Similarity	NPC87413
0.7442	Intermediate Similarity	NPC98715
0.7441	Intermediate Similarity	NPC11445
0.7438	Intermediate Similarity	NPC283219
0.7435	Intermediate Similarity	NPC323752
0.7431	Intermediate Similarity	NPC271862
0.7426	Intermediate Similarity	NPC267885
0.7424	Intermediate Similarity	NPC119006
0.7424	Intermediate Similarity	NPC260434
0.7419	Intermediate Similarity	NPC46225
0.7419	Intermediate Similarity	NPC225821
0.7418	Intermediate Similarity	NPC132385
0.7418	Intermediate Similarity	NPC280714
0.7412	Intermediate Similarity	NPC194740
0.7407	Intermediate Similarity	NPC472259
0.7406	Intermediate Similarity	NPC471536

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 NPC276657 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	646
0.2-0.3	866
0.3-0.4	1575
0.4-0.5	2803
0.5-0.6	1947
0.6-0.7	876
0.7-0.8	112
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8768	High Similarity	NPD4845	Discontinued
0.8507	High Similarity	NPD484	Approved
0.831	Intermediate Similarity	NPD6242	Discontinued
0.83	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD5901	Discontinued
0.8	Intermediate Similarity	NPD7948	Phase 1
0.7982	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD5426	Phase 3
0.7806	Intermediate Similarity	NPD6531	Approved
0.7806	Intermediate Similarity	NPD6530	Approved
0.7793	Intermediate Similarity	NPD7603	Discontinued
0.7793	Intermediate Similarity	NPD2509	Approved
0.7793	Intermediate Similarity	NPD2510	Approved
0.7768	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD1038	Approved
0.7706	Intermediate Similarity	NPD5612	Discontinued
0.7685	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7675	Intermediate Similarity	NPD3006	Discontinued
0.7672	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6999	Discontinued
0.7667	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD4429	Discontinued
0.7635	Intermediate Similarity	NPD2096	Phase 2
0.7635	Intermediate Similarity	NPD2091	Phase 2
0.7626	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD2095	Phase 2
0.7586	Intermediate Similarity	NPD2094	Phase 2
0.7586	Intermediate Similarity	NPD2092	Phase 2
0.7535	Intermediate Similarity	NPD7001	Phase 3
0.7524	Intermediate Similarity	NPD4948	Discontinued
0.7523	Intermediate Similarity	NPD7470	Discontinued
0.7488	Intermediate Similarity	NPD6987	Phase 1
0.7467	Intermediate Similarity	NPD3746	Discontinued
0.7466	Intermediate Similarity	NPD3389	Approved
0.7466	Intermediate Similarity	NPD3394	Approved
0.7466	Intermediate Similarity	NPD3393	Approved
0.7463	Intermediate Similarity	NPD482	Approved
0.7456	Intermediate Similarity	NPD5022	Discontinued
0.7447	Intermediate Similarity	NPD3959	Phase 2
0.7447	Intermediate Similarity	NPD3962	Phase 2
0.7436	Intermediate Similarity	NPD3914	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD8091	Phase 3
0.7426	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3947	Discontinued
0.7402	Intermediate Similarity	NPD6595	Phase 3
0.7399	Intermediate Similarity	NPD3354	Phase 2
0.7397	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7666	Phase 3
0.7385	Intermediate Similarity	NPD7665	Phase 2
0.7383	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5065	Approved
0.7353	Intermediate Similarity	NPD4558	Phase 2
0.7346	Intermediate Similarity	NPD802	Phase 2
0.7336	Intermediate Similarity	NPD8396	Approved
0.7336	Intermediate Similarity	NPD8395	Approved
0.733	Intermediate Similarity	NPD4852	Phase 2
0.7328	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD3960	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD6376	Discontinued
0.7295	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6164	Phase 2
0.7293	Intermediate Similarity	NPD6165	Phase 2
0.7284	Intermediate Similarity	NPD4373	Phase 2
0.7282	Intermediate Similarity	NPD3178	Discontinued
0.7277	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3825	Phase 3
0.7251	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5482	Discontinued
0.7246	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4952	Phase 3
0.7227	Intermediate Similarity	NPD2916	Discontinued
0.722	Intermediate Similarity	NPD3243	Approved
0.7215	Intermediate Similarity	NPD2008	Discontinued
0.7212	Intermediate Similarity	NPD3258	Approved
0.7207	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5416	Discontinued
0.7193	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8096	Phase 3
0.7175	Intermediate Similarity	NPD8097	Phase 3
0.7175	Intermediate Similarity	NPD2411	Approved
0.7175	Intermediate Similarity	NPD8093	Discontinued
0.7173	Intermediate Similarity	NPD6790	Phase 1
0.7169	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD750	Phase 2
0.7149	Intermediate Similarity	NPD2189	Approved
0.7149	Intermediate Similarity	NPD2187	Approved
0.7143	Intermediate Similarity	NPD8094	Discontinued
0.7137	Intermediate Similarity	NPD4850	Phase 1
0.7116	Intermediate Similarity	NPD4848	Phase 1
0.7111	Intermediate Similarity	NPD3257	Approved
0.711	Intermediate Similarity	NPD4511	Phase 1
0.7097	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD2844	Phase 3
0.7093	Intermediate Similarity	NPD7878	Phase 2
0.7093	Intermediate Similarity	NPD5632	Approved
0.7089	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2336	Approved
0.7088	Intermediate Similarity	NPD8349	Phase 1
0.7085	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6733	Discontinued
0.707	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7994	Phase 2
0.7067	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3795	Approved
0.7067	Intermediate Similarity	NPD3794	Approved
0.7059	Intermediate Similarity	NPD4561	Discontinued
0.7059	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6995	Phase 1
0.7039	Intermediate Similarity	NPD5559	Phase 2
0.7037	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3986	Discontinued
0.7035	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD8358	Approved
0.7009	Intermediate Similarity	NPD5479	Discontinued
0.7	Intermediate Similarity	NPD6456	Discontinued
0.6996	Remote Similarity	NPD3259	Approved
0.6996	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5475	Discontinued
0.6976	Remote Similarity	NPD1573	Approved
0.6976	Remote Similarity	NPD1575	Approved
0.6976	Remote Similarity	NPD1325	Approved
0.6976	Remote Similarity	NPD1326	Approved
0.6972	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD3809	Discontinued
0.6959	Remote Similarity	NPD2307	Discontinued
0.695	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4885	Approved
0.6948	Remote Similarity	NPD8431	Approved
0.6947	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3330	Phase 1
0.6947	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3222	Phase 2
0.6933	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7112	Discontinued
0.693	Remote Similarity	NPD8160	Phase 2
0.6923	Remote Similarity	NPD8073	Approved
0.6923	Remote Similarity	NPD4328	Approved
0.692	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.692	Remote Similarity	NPD7558	Phase 2
0.6912	Remote Similarity	NPD4418	Discontinued
0.6907	Remote Similarity	NPD6962	Phase 2
0.6906	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5450	Discontinued
0.6905	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5067	Phase 2
0.6903	Remote Similarity	NPD5066	Phase 2
0.6903	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.69	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6176	Phase 1
0.6886	Remote Similarity	NPD5293	Phase 2
0.6886	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD8463	Approved
0.688	Remote Similarity	NPD6228	Discontinued
0.6875	Remote Similarity	NPD7452	Approved
0.6875	Remote Similarity	NPD7453	Approved
0.6875	Remote Similarity	NPD7222	Phase 2
0.6873	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6873	Remote Similarity	NPD7181	Phase 3
0.6864	Remote Similarity	NPD3814	Phase 1
0.6862	Remote Similarity	NPD7853	Phase 2
0.6861	Remote Similarity	NPD8098	Approved
0.6861	Remote Similarity	NPD4795	Phase 2
0.6861	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7925	Phase 2
0.685	Remote Similarity	NPD7924	Phase 2
0.6849	Remote Similarity	NPD5003	Discontinued
0.6847	Remote Similarity	NPD3931	Approved
0.6847	Remote Similarity	NPD6975	Discontinued
0.6847	Remote Similarity	NPD3928	Approved
0.6845	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD5658	Approved
0.6842	Remote Similarity	NPD3004	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6770	Approved
0.6838	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8101	Phase 3
0.6825	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2479	Phase 3
0.6825	Remote Similarity	NPD2481	Approved
0.682	Remote Similarity	NPD6665	Discontinued

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