NPASS Compound

Structure

CID199926 OpenBabel06191715592D 21 23 0 0 1 0 0 0 0 0999 V2000 3.4049 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9049 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 -1.0000 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 1 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 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 -1.7321 -3.0000 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 0.8660 -1.5000 0.0000 C 0 0 2 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 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 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 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 19 1 0 0 0 0 3 4 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 4 1 6 0 0 0 7 20 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 5 1 6 0 0 0 10 14 1 0 0 0 0 10 21 1 0 0 0 0 11 13 2 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 8 1 6 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.11
Volume:	284.522
LogP:	2.71
LogD:	2.198
LogS:	-3.457
# Rotatable Bonds:	3
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	3.827
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862
MDCK Permeability:	2.0876161215710454e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.207
Plasma Protein Binding (PPB):	94.78550720214844%
Volume Distribution (VD):	0.653
Pgp-substrate:	5.470870494842529%

ADMET: Metabolism

CYP1A2-inhibitor:	0.12
CYP1A2-substrate:	0.622
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.139
CYP2C9-substrate:	0.782
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.291
CYP3A4-inhibitor:	0.31
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	11.537
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.243
Drug-inuced Liver Injury (DILI):	0.726
AMES Toxicity:	0.243
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.714
Skin Sensitization:	0.923
Carcinogencity:	0.797
Eye Corrosion:	0.004
Eye Irritation:	0.775
Respiratory Toxicity:	0.394

Download Data

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

Natural Product: NPC199926

Natural Product ID:	NPC199926
*Common Name:**	(2S,3Ar,9Br)-6,7-Dihydroxy-8-Methoxy-2-Propyl-2,3,3A,9B-Tetrahydrofuro[3,2-C]Isochromen-5-One
IUPAC Name:	(2S,3aR,9bR)-6,7-dihydroxy-8-methoxy-2-propyl-2,3,3a,9b-tetrahydrofuro[3,2-c]isochromen-5-one
Synonyms:
Standard InCHIKey:	XFTQOARYRNZEFJ-LTRYTXMFSA-N
Standard InCHI:	InChI=1S/C15H18O6/c1-3-4-7-5-10-14(20-7)8-6-9(19-2)12(16)13(17)11(8)15(18)21-10/h6-7,10,14,16-17H,3-5H2,1-2H3/t7-,10+,14+/m0/s1
SMILES:	CCC[C@H]1C[C@@H]2[C@H](O1)c1cc(OC)c(c(c1C(=O)O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668326
PubChem CID:	51354813
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO31360	Colletotrichum	Genus	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21174408]
NPO32863	colletotrichum sp.	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21174408]
NPO40509	Setosphaeria sp. SCSIO41009	Strain	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30091601]

☑ 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	11

Activity Type	# Activity
Cell Line	4
Individual Protein	2
NON-MOLECULAR	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	23700.0	nM	PMID[540347]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	169800.0	nM	PMID[540347]
NPT793	Cell Line	MOLT-3	Homo sapiens	IC50	=	124300.0	nM	PMID[540347]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	>	16900.0	nM	PMID[540347]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	136000.0	nM	PMID[540347]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	169800.0	nM	PMID[540347]
NPT1	Others	Radical scavenging activity		IC50	=	23400.0	nM	PMID[540347]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	52600.0	nM	PMID[540347]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	>	679000.0	nM	PMID[540347]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11500.0	nM	PMID[540347]
NPT35	Others	n.a.		IC50	=	38000.0	nM	PMID[540348]

☑ 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 NPC199926 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	349
0.1-0.2	1419
0.2-0.3	3295
0.3-0.4	7770
0.4-0.5	10479
0.5-0.6	4073
0.6-0.7	5265
0.7-0.8	7312
0.8-0.85	2187
0.85-0.9	503
0.9-0.95	35
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC150227
0.9866	High Similarity	NPC77679
0.9866	High Similarity	NPC190020
0.9866	High Similarity	NPC84935
0.9797	High Similarity	NPC281477
0.9732	High Similarity	NPC79998
0.9732	High Similarity	NPC82592
0.9732	High Similarity	NPC16082
0.9728	High Similarity	NPC96501
0.9408	High Similarity	NPC227062
0.9324	High Similarity	NPC32058
0.9324	High Similarity	NPC85734
0.932	High Similarity	NPC27106
0.9276	High Similarity	NPC116850
0.9276	High Similarity	NPC197188
0.9276	High Similarity	NPC144801
0.9276	High Similarity	NPC43872
0.9276	High Similarity	NPC238672
0.9276	High Similarity	NPC291510
0.9272	High Similarity	NPC70016
0.9272	High Similarity	NPC215921
0.9272	High Similarity	NPC240768
0.9272	High Similarity	NPC473732
0.9272	High Similarity	NPC200773
0.9226	High Similarity	NPC200594
0.9211	High Similarity	NPC475116
0.9211	High Similarity	NPC295646
0.9205	High Similarity	NPC179178
0.9177	High Similarity	NPC472452
0.9172	High Similarity	NPC475985
0.9156	High Similarity	NPC54928
0.9145	High Similarity	NPC204350
0.9139	High Similarity	NPC237440
0.9139	High Similarity	NPC270160
0.9122	High Similarity	NPC258307
0.9122	High Similarity	NPC469542
0.9116	High Similarity	NPC90411
0.9114	High Similarity	NPC326520
0.9103	High Similarity	NPC24627
0.9091	High Similarity	NPC20541
0.9085	High Similarity	NPC167903
0.9067	High Similarity	NPC260946
0.9067	High Similarity	NPC138978
0.9057	High Similarity	NPC170245
0.9051	High Similarity	NPC249181
0.902	High Similarity	NPC228662
0.9007	High Similarity	NPC476463
0.8994	High Similarity	NPC191930
0.8993	High Similarity	NPC51106
0.8993	High Similarity	NPC472006
0.8987	High Similarity	NPC215612
0.8986	High Similarity	NPC1704
0.8986	High Similarity	NPC67650
0.8981	High Similarity	NPC36217
0.898	High Similarity	NPC471819
0.8974	High Similarity	NPC300727
0.8974	High Similarity	NPC241904
0.8968	High Similarity	NPC67396
0.8968	High Similarity	NPC38898
0.8968	High Similarity	NPC16286
0.8954	High Similarity	NPC151473
0.8954	High Similarity	NPC469670
0.8954	High Similarity	NPC469619
0.8951	High Similarity	NPC471181
0.894	High Similarity	NPC107625
0.8938	High Similarity	NPC20237
0.8933	High Similarity	NPC210425
0.8933	High Similarity	NPC277426
0.8933	High Similarity	NPC86373
0.8933	High Similarity	NPC280404
0.8931	High Similarity	NPC18100
0.8926	High Similarity	NPC469579
0.8924	High Similarity	NPC117985
0.8917	High Similarity	NPC470339
0.8917	High Similarity	NPC476242
0.8917	High Similarity	NPC238381
0.8917	High Similarity	NPC45846
0.8917	High Similarity	NPC329091
0.891	High Similarity	NPC274730
0.891	High Similarity	NPC24640
0.891	High Similarity	NPC197751
0.891	High Similarity	NPC301897
0.8903	High Similarity	NPC25127
0.8903	High Similarity	NPC287504
0.8903	High Similarity	NPC192189
0.8903	High Similarity	NPC18727
0.8882	High Similarity	NPC166583
0.8882	High Similarity	NPC283041
0.8882	High Similarity	NPC53362
0.8875	High Similarity	NPC473286
0.8875	High Similarity	NPC472277
0.8874	High Similarity	NPC316535
0.8868	High Similarity	NPC472964
0.8868	High Similarity	NPC144843
0.8868	High Similarity	NPC201800
0.8867	High Similarity	NPC27159
0.8861	High Similarity	NPC472055
0.8861	High Similarity	NPC472902
0.8861	High Similarity	NPC14353
0.8861	High Similarity	NPC56085
0.8861	High Similarity	NPC292415
0.8861	High Similarity	NPC472624
0.8861	High Similarity	NPC228785
0.8854	High Similarity	NPC108456
0.8854	High Similarity	NPC474208
0.8854	High Similarity	NPC469584
0.8854	High Similarity	NPC179732
0.8854	High Similarity	NPC129684
0.8854	High Similarity	NPC48208
0.8854	High Similarity	NPC299520
0.8854	High Similarity	NPC162869
0.8854	High Similarity	NPC473395
0.8854	High Similarity	NPC475267
0.8854	High Similarity	NPC156057
0.8854	High Similarity	NPC474836
0.8846	High Similarity	NPC45849
0.8846	High Similarity	NPC200761
0.8846	High Similarity	NPC477503
0.8846	High Similarity	NPC470327
0.8844	High Similarity	NPC135837
0.8839	High Similarity	NPC302950
0.8839	High Similarity	NPC289968
0.8839	High Similarity	NPC219582
0.8839	High Similarity	NPC199773
0.8839	High Similarity	NPC236637
0.8831	High Similarity	NPC338131
0.8831	High Similarity	NPC119929
0.882	High Similarity	NPC477517
0.8816	High Similarity	NPC268366
0.8812	High Similarity	NPC186686
0.8812	High Similarity	NPC205265
0.8812	High Similarity	NPC474350
0.8812	High Similarity	NPC133065
0.8812	High Similarity	NPC124038
0.8812	High Similarity	NPC476822
0.8812	High Similarity	NPC472281
0.8812	High Similarity	NPC7483
0.8808	High Similarity	NPC470932
0.8805	High Similarity	NPC61010
0.8805	High Similarity	NPC473106
0.8805	High Similarity	NPC112418
0.8805	High Similarity	NPC278052
0.8805	High Similarity	NPC103201
0.8805	High Similarity	NPC474186
0.8805	High Similarity	NPC349525
0.8805	High Similarity	NPC40491
0.8805	High Similarity	NPC201560
0.88	High Similarity	NPC474385
0.88	High Similarity	NPC322112
0.8797	High Similarity	NPC100123
0.8797	High Similarity	NPC85121
0.8797	High Similarity	NPC279732
0.8797	High Similarity	NPC477410
0.8797	High Similarity	NPC210459
0.8797	High Similarity	NPC87317
0.8797	High Similarity	NPC315157
0.8792	High Similarity	NPC187690
0.879	High Similarity	NPC235165
0.879	High Similarity	NPC255106
0.879	High Similarity	NPC470328
0.879	High Similarity	NPC209614
0.879	High Similarity	NPC195796
0.879	High Similarity	NPC472626
0.879	High Similarity	NPC472050
0.879	High Similarity	NPC278778
0.879	High Similarity	NPC317383
0.879	High Similarity	NPC291878
0.879	High Similarity	NPC35038
0.8784	High Similarity	NPC472602
0.8784	High Similarity	NPC233780
0.8782	High Similarity	NPC301233
0.8782	High Similarity	NPC89474
0.8776	High Similarity	NPC235115
0.8774	High Similarity	NPC202157
0.8774	High Similarity	NPC151425
0.8773	High Similarity	NPC17219
0.8766	High Similarity	NPC4423
0.8766	High Similarity	NPC77325
0.8765	High Similarity	NPC471180
0.8765	High Similarity	NPC117854
0.8765	High Similarity	NPC6588
0.8765	High Similarity	NPC477154
0.8758	High Similarity	NPC30647
0.8758	High Similarity	NPC471788
0.8758	High Similarity	NPC475888
0.8758	High Similarity	NPC39306
0.8758	High Similarity	NPC210320
0.8758	High Similarity	NPC108433
0.8758	High Similarity	NPC8817
0.8758	High Similarity	NPC300053
0.8758	High Similarity	NPC55557
0.8758	High Similarity	NPC8070
0.8758	High Similarity	NPC61871
0.8758	High Similarity	NPC293319
0.875	High Similarity	NPC472635
0.875	High Similarity	NPC471745
0.875	High Similarity	NPC75694
0.875	High Similarity	NPC83272
0.875	High Similarity	NPC48860
0.875	High Similarity	NPC474763

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 NPC199926 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	857
0.2-0.3	1903
0.3-0.4	2554
0.4-0.5	1905
0.5-0.6	1003
0.6-0.7	451
0.7-0.8	144
0.8-0.85	22
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8839	High Similarity	NPD1934	Approved
0.875	High Similarity	NPD2532	Approved
0.875	High Similarity	NPD2533	Approved
0.875	High Similarity	NPD2534	Approved
0.8725	High Similarity	NPD970	Clinical (unspecified phase)
0.8671	High Similarity	NPD3882	Suspended
0.8671	High Similarity	NPD4868	Clinical (unspecified phase)
0.8662	High Similarity	NPD2393	Clinical (unspecified phase)
0.8634	High Similarity	NPD6232	Discontinued
0.8544	High Similarity	NPD1465	Phase 2
0.8544	High Similarity	NPD2801	Approved
0.8537	High Similarity	NPD3818	Discontinued
0.8476	Intermediate Similarity	NPD7473	Discontinued
0.8446	Intermediate Similarity	NPD230	Phase 1
0.8415	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD6166	Phase 2
0.8415	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD6234	Discontinued
0.8323	Intermediate Similarity	NPD7074	Phase 3
0.8323	Intermediate Similarity	NPD1511	Approved
0.8284	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD5494	Approved
0.8263	Intermediate Similarity	NPD7054	Approved
0.8263	Intermediate Similarity	NPD5844	Phase 1
0.8217	Intermediate Similarity	NPD1512	Approved
0.8214	Intermediate Similarity	NPD7472	Approved
0.8199	Intermediate Similarity	NPD7819	Suspended
0.8182	Intermediate Similarity	NPD5710	Approved
0.8182	Intermediate Similarity	NPD5711	Approved
0.816	Intermediate Similarity	NPD7075	Discontinued
0.8137	Intermediate Similarity	NPD37	Approved
0.8125	Intermediate Similarity	NPD4380	Phase 2
0.8098	Intermediate Similarity	NPD4965	Approved
0.8098	Intermediate Similarity	NPD4966	Approved
0.8098	Intermediate Similarity	NPD4967	Phase 2
0.8095	Intermediate Similarity	NPD7228	Approved
0.8086	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD6797	Phase 2
0.8052	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7251	Discontinued
0.8	Intermediate Similarity	NPD1549	Phase 2
0.8	Intermediate Similarity	NPD919	Approved
0.7975	Intermediate Similarity	NPD6799	Approved
0.7965	Intermediate Similarity	NPD7808	Phase 3
0.7961	Intermediate Similarity	NPD447	Suspended
0.7939	Intermediate Similarity	NPD3749	Approved
0.7939	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1510	Phase 2
0.7904	Intermediate Similarity	NPD6959	Discontinued
0.7904	Intermediate Similarity	NPD7199	Phase 2
0.7901	Intermediate Similarity	NPD6599	Discontinued
0.7895	Intermediate Similarity	NPD1240	Approved
0.7895	Intermediate Similarity	NPD943	Approved
0.7834	Intermediate Similarity	NPD2800	Approved
0.7829	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6801	Discontinued
0.7803	Intermediate Similarity	NPD6559	Discontinued
0.7798	Intermediate Similarity	NPD1247	Approved
0.7797	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1607	Approved
0.7756	Intermediate Similarity	NPD2935	Discontinued
0.775	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7411	Suspended
0.7716	Intermediate Similarity	NPD920	Approved
0.7711	Intermediate Similarity	NPD5402	Approved
0.7711	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD5353	Approved
0.7706	Intermediate Similarity	NPD3926	Phase 2
0.7703	Intermediate Similarity	NPD9269	Phase 2
0.7697	Intermediate Similarity	NPD3027	Phase 3
0.7682	Intermediate Similarity	NPD9494	Approved
0.7673	Intermediate Similarity	NPD4628	Phase 3
0.7673	Intermediate Similarity	NPD3750	Approved
0.7673	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1653	Approved
0.7662	Intermediate Similarity	NPD1613	Approved
0.7662	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2796	Approved
0.7643	Intermediate Similarity	NPD1551	Phase 2
0.763	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1243	Approved
0.76	Intermediate Similarity	NPD7685	Pre-registration
0.76	Intermediate Similarity	NPD7240	Approved
0.7593	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7768	Phase 2
0.7558	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD5242	Approved
0.75	Intermediate Similarity	NPD5403	Approved
0.7469	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD9268	Approved
0.741	Intermediate Similarity	NPD3226	Approved
0.7382	Intermediate Similarity	NPD8151	Discontinued
0.7378	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5401	Approved
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7374	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3751	Discontinued
0.7358	Intermediate Similarity	NPD3748	Approved
0.7342	Intermediate Similarity	NPD6651	Approved
0.7341	Intermediate Similarity	NPD3787	Discontinued
0.7341	Intermediate Similarity	NPD7229	Phase 3
0.734	Intermediate Similarity	NPD5005	Approved
0.734	Intermediate Similarity	NPD5006	Approved
0.7326	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8312	Approved
0.7318	Intermediate Similarity	NPD8313	Approved
0.7312	Intermediate Similarity	NPD6100	Approved
0.7312	Intermediate Similarity	NPD6099	Approved
0.7308	Intermediate Similarity	NPD3764	Approved
0.7308	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD8150	Discontinued
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.7284	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1933	Approved
0.7273	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2344	Approved
0.725	Intermediate Similarity	NPD2799	Discontinued
0.7248	Intermediate Similarity	NPD9545	Approved
0.7247	Intermediate Similarity	NPD5953	Discontinued
0.7237	Intermediate Similarity	NPD9717	Approved
0.7232	Intermediate Similarity	NPD7286	Phase 2
0.7219	Intermediate Similarity	NPD6386	Approved
0.7219	Intermediate Similarity	NPD4420	Approved
0.7219	Intermediate Similarity	NPD6385	Approved
0.7212	Intermediate Similarity	NPD7390	Discontinued
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.7208	Intermediate Similarity	NPD1203	Approved
0.7178	Intermediate Similarity	NPD2654	Approved
0.7178	Intermediate Similarity	NPD1652	Phase 2
0.7171	Intermediate Similarity	NPD422	Phase 1
0.7171	Intermediate Similarity	NPD3705	Approved
0.717	Intermediate Similarity	NPD6355	Discontinued
0.7159	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD6782	Approved
0.7143	Intermediate Similarity	NPD6779	Approved
0.7143	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD6778	Approved
0.7143	Intermediate Similarity	NPD6781	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD6777	Approved
0.7134	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4110	Phase 3
0.7124	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD7680	Approved
0.7114	Intermediate Similarity	NPD9493	Approved
0.7107	Intermediate Similarity	NPD4060	Phase 1
0.7101	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2309	Approved
0.7089	Intermediate Similarity	NPD411	Approved
0.7086	Intermediate Similarity	NPD8127	Discontinued
0.7078	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6832	Phase 2
0.7063	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7266	Discontinued
0.7041	Intermediate Similarity	NPD7783	Phase 2
0.7041	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4287	Approved
0.7018	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5404	Approved
0.6994	Remote Similarity	NPD5406	Approved
0.6994	Remote Similarity	NPD5408	Approved
0.6994	Remote Similarity	NPD5405	Approved
0.699	Remote Similarity	NPD7874	Approved
0.699	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6798	Discontinued
0.6981	Remote Similarity	NPD2313	Discontinued
0.6971	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4908	Phase 1
0.6957	Remote Similarity	NPD5124	Phase 1
0.6957	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6005	Phase 3
0.6951	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6002	Phase 3
0.6951	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6004	Phase 3
0.6948	Remote Similarity	NPD1610	Phase 2
0.6943	Remote Similarity	NPD1019	Discontinued
0.6943	Remote Similarity	NPD7698	Approved
0.6943	Remote Similarity	NPD7697	Approved
0.6943	Remote Similarity	NPD7696	Phase 3
0.6935	Remote Similarity	NPD7930	Approved
0.6928	Remote Similarity	NPD4626	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