NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.04
Volume:	171.722
LogP:	2.244
LogD:	2.536
LogS:	-2.25
# Rotatable Bonds:	1
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.703
Synthetic Accessibility Score:	2.777
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.751
MDCK Permeability:	9.55399536906043e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	95.98221588134766%
Volume Distribution (VD):	0.625
Pgp-substrate:	9.072514533996582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.877
CYP1A2-substrate:	0.848
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.277
CYP2C9-substrate:	0.798
CYP2D6-inhibitor:	0.572
CYP2D6-substrate:	0.691
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	13.619
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.364
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.777
Maximum Recommended Daily Dose:	0.329
Skin Sensitization:	0.833
Carcinogencity:	0.761
Eye Corrosion:	0.278
Eye Irritation:	0.942
Respiratory Toxicity:	0.62

Download Data

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

Natural Product: NPC90411

Natural Product ID:	NPC90411
*Common Name:**	Sid22414536
IUPAC Name:	7-hydroxy-5-methoxy-3H-2-benzofuran-1-one
Synonyms:
Standard InCHIKey:	DQVAVEZQPWBKEW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H8O4/c1-12-6-2-5-4-13-9(11)8(5)7(10)3-6/h2-3,10H,4H2,1H3
SMILES:	COc1cc2COC(=O)c2c(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507369
PubChem CID:	181107
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004191] Isocoumarans [CHEMONTID:0003409] Isobenzofuranones [CHEMONTID:0001873] Phthalides

*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
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	root	n.a.	n.a.	PMID[2778455]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29300477]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	Database[Article]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23736	Myrsine africana	Species	Primulaceae	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
EC50	1
ED50	3
IC50	1
Others	1
Potency	7

Activity Type	# Activity
Cell Line	2
Individual Protein	6
NON-MOLECULAR	1
Organism	1
Others	1
PROTEIN COMPLEX	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	28.0	ug ml-1	PMID[521563]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	100.0	ug ml-1	PMID[521563]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	35481.3	nM	PMID[521564]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	11220.2	nM	PMID[521564]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	25118.9	nM	PMID[521564]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	3981.1	nM	PMID[521564]
NPT140	Organism	Artemia	Artemia	LC50	>	1000.0	ppm	PMID[521563]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	100.0	ug ml-1	PMID[521563]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	7079.5	nM	PMID[521564]
NPT2	Others	Unspecified		Potency	n.a.	4.6	nM	PMID[521564]
NPT25197	PROTEIN COMPLEX	Corticotropin-releasing factor receptor 2/Corticotropin-releasing factor-binding protein	Homo sapiens	EC50	>	53000.0	nM	PMID[521564]
NPT25197	PROTEIN COMPLEX	Corticotropin-releasing factor receptor 2/Corticotropin-releasing factor-binding protein	Homo sapiens	IC50	>	47100.0	nM	PMID[521564]

☑ 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 NPC90411 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	346
0.1-0.2	1670
0.2-0.3	4216
0.3-0.4	9151
0.4-0.5	9002
0.5-0.6	3583
0.6-0.7	6080
0.7-0.8	6651
0.8-0.85	1616
0.85-0.9	302
0.9-0.95	76
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC135837
0.9552	High Similarity	NPC182496
0.9552	High Similarity	NPC180905
0.9424	High Similarity	NPC51106
0.9424	High Similarity	NPC472006
0.942	High Similarity	NPC67650
0.942	High Similarity	NPC1704
0.9416	High Similarity	NPC275356
0.9403	High Similarity	NPC153783
0.9371	High Similarity	NPC119929
0.9371	High Similarity	NPC96501
0.9362	High Similarity	NPC107625
0.9353	High Similarity	NPC474385
0.9306	High Similarity	NPC240768
0.9306	High Similarity	NPC200773
0.9291	High Similarity	NPC75694
0.9286	High Similarity	NPC469542
0.9281	High Similarity	NPC475730
0.9254	High Similarity	NPC219892
0.9254	High Similarity	NPC189823
0.9241	High Similarity	NPC271681
0.9236	High Similarity	NPC179178
0.9225	High Similarity	NPC472033
0.922	High Similarity	NPC210425
0.922	High Similarity	NPC86373
0.922	High Similarity	NPC277426
0.922	High Similarity	NPC280404
0.9209	High Similarity	NPC165172
0.9197	High Similarity	NPC235115
0.9191	High Similarity	NPC175943
0.9167	High Similarity	NPC198927
0.9161	High Similarity	NPC8817
0.9161	High Similarity	NPC472036
0.9161	High Similarity	NPC137296
0.9155	High Similarity	NPC472034
0.9143	High Similarity	NPC220106
0.9137	High Similarity	NPC268052
0.9137	High Similarity	NPC32360
0.913	High Similarity	NPC70380
0.9116	High Similarity	NPC199926
0.9116	High Similarity	NPC79998
0.9103	High Similarity	NPC469670
0.9103	High Similarity	NPC469619
0.9097	High Similarity	NPC153417
0.9091	High Similarity	NPC470357
0.9091	High Similarity	NPC260946
0.9085	High Similarity	NPC27106
0.9085	High Similarity	NPC66404
0.9085	High Similarity	NPC95123
0.9085	High Similarity	NPC470932
0.9078	High Similarity	NPC250755
0.9078	High Similarity	NPC297985
0.9078	High Similarity	NPC469579
0.9078	High Similarity	NPC105648
0.9065	High Similarity	NPC478200
0.9065	High Similarity	NPC33144
0.9065	High Similarity	NPC212693
0.9065	High Similarity	NPC94248
0.9065	High Similarity	NPC191835
0.9054	High Similarity	NPC150227
0.9041	High Similarity	NPC70016
0.9041	High Similarity	NPC215921
0.9034	High Similarity	NPC270160
0.9034	High Similarity	NPC4423
0.9034	High Similarity	NPC237440
0.9034	High Similarity	NPC77325
0.903	High Similarity	NPC293453
0.9028	High Similarity	NPC166583
0.9028	High Similarity	NPC210320
0.9028	High Similarity	NPC53362
0.9028	High Similarity	NPC14098
0.9021	High Similarity	NPC312789
0.9021	High Similarity	NPC134621
0.9021	High Similarity	NPC473692
0.9007	High Similarity	NPC244923
0.9007	High Similarity	NPC158634
0.9	High Similarity	NPC52358
0.9	High Similarity	NPC139634
0.9	High Similarity	NPC247409
0.9	High Similarity	NPC92655
0.9	High Similarity	NPC105456
0.9	High Similarity	NPC471819
0.8993	High Similarity	NPC84935
0.8993	High Similarity	NPC77679
0.8993	High Similarity	NPC190020
0.8993	High Similarity	NPC473395
0.8973	High Similarity	NPC295036
0.8973	High Similarity	NPC470107
0.8966	High Similarity	NPC471641
0.8966	High Similarity	NPC471642
0.8966	High Similarity	NPC240253
0.8966	High Similarity	NPC215711
0.8966	High Similarity	NPC73411
0.8966	High Similarity	NPC172329
0.8966	High Similarity	NPC240622
0.8966	High Similarity	NPC2569
0.8958	High Similarity	NPC267509
0.8958	High Similarity	NPC237208
0.8958	High Similarity	NPC85734
0.8958	High Similarity	NPC32058
0.8951	High Similarity	NPC184702
0.8936	High Similarity	NPC158472
0.8929	High Similarity	NPC472602
0.8921	High Similarity	NPC242712
0.8921	High Similarity	NPC158481
0.8921	High Similarity	NPC50455
0.8919	High Similarity	NPC281477
0.8912	High Similarity	NPC204350
0.8904	High Similarity	NPC476684
0.8897	High Similarity	NPC42292
0.8897	High Similarity	NPC307732
0.8889	High Similarity	NPC32470
0.8889	High Similarity	NPC316535
0.8889	High Similarity	NPC29577
0.8889	High Similarity	NPC83272
0.8881	High Similarity	NPC258307
0.8874	High Similarity	NPC200594
0.8873	High Similarity	NPC472035
0.8873	High Similarity	NPC37530
0.8873	High Similarity	NPC313123
0.8873	High Similarity	NPC478217
0.8873	High Similarity	NPC478201
0.8873	High Similarity	NPC53649
0.8865	High Similarity	NPC57380
0.8865	High Similarity	NPC88269
0.8859	High Similarity	NPC82592
0.8859	High Similarity	NPC16082
0.8859	High Similarity	NPC99381
0.8857	High Similarity	NPC71256
0.8857	High Similarity	NPC194579
0.8851	High Similarity	NPC175978
0.8851	High Similarity	NPC167903
0.8851	High Similarity	NPC273483
0.8828	High Similarity	NPC225173
0.8828	High Similarity	NPC163846
0.8828	High Similarity	NPC138978
0.8819	High Similarity	NPC478203
0.8819	High Similarity	NPC475201
0.8819	High Similarity	NPC126882
0.8819	High Similarity	NPC210966
0.8815	High Similarity	NPC128428
0.8815	High Similarity	NPC305518
0.8811	High Similarity	NPC82913
0.8811	High Similarity	NPC96692
0.8811	High Similarity	NPC49108
0.8811	High Similarity	NPC322112
0.8806	High Similarity	NPC262671
0.8806	High Similarity	NPC201728
0.8803	High Similarity	NPC99441
0.8803	High Similarity	NPC472601
0.8803	High Similarity	NPC472600
0.8803	High Similarity	NPC155205
0.8794	High Similarity	NPC233780
0.8792	High Similarity	NPC192189
0.8784	High Similarity	NPC106372
0.8784	High Similarity	NPC115324
0.8784	High Similarity	NPC58668
0.8776	High Similarity	NPC233267
0.8776	High Similarity	NPC291049
0.8767	High Similarity	NPC125801
0.8767	High Similarity	NPC12305
0.8759	High Similarity	NPC257558
0.875	High Similarity	NPC159721
0.875	High Similarity	NPC310340
0.875	High Similarity	NPC478202
0.8741	High Similarity	NPC472603
0.8741	High Similarity	NPC472605
0.8741	High Similarity	NPC275734
0.8741	High Similarity	NPC472604
0.8725	High Similarity	NPC207624
0.8723	High Similarity	NPC474849
0.8723	High Similarity	NPC178467
0.8723	High Similarity	NPC65837
0.8723	High Similarity	NPC474771
0.8723	High Similarity	NPC149372
0.8716	High Similarity	NPC202595
0.8716	High Similarity	NPC60413
0.8707	High Similarity	NPC470359
0.8707	High Similarity	NPC216624
0.8707	High Similarity	NPC37139
0.8707	High Similarity	NPC105415
0.8705	High Similarity	NPC203817
0.8696	High Similarity	NPC470831
0.8696	High Similarity	NPC214702
0.8693	High Similarity	NPC117985
0.869	High Similarity	NPC42540
0.869	High Similarity	NPC151607
0.869	High Similarity	NPC19896
0.8686	High Similarity	NPC212379
0.8686	High Similarity	NPC69235
0.8684	High Similarity	NPC279732
0.8684	High Similarity	NPC470339
0.8681	High Similarity	NPC471644
0.8681	High Similarity	NPC182255
0.8681	High Similarity	NPC471640
0.8681	High Similarity	NPC94076
0.8681	High Similarity	NPC18714
0.8675	High Similarity	NPC227062
0.8675	High Similarity	NPC54928
0.8675	High Similarity	NPC146211

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 NPC90411 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	970
0.2-0.3	1884
0.3-0.4	2579
0.4-0.5	1759
0.5-0.6	1084
0.6-0.7	390
0.7-0.8	140
0.8-0.85	24
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9416	High Similarity	NPD970	Clinical (unspecified phase)
0.9291	High Similarity	NPD2534	Approved
0.9291	High Similarity	NPD2533	Approved
0.9291	High Similarity	NPD2532	Approved
0.844	Intermediate Similarity	NPD230	Phase 1
0.8421	Intermediate Similarity	NPD7819	Suspended
0.8397	Intermediate Similarity	NPD5710	Approved
0.8397	Intermediate Similarity	NPD5711	Approved
0.8392	Intermediate Similarity	NPD1510	Phase 2
0.8369	Intermediate Similarity	NPD1240	Approved
0.8288	Intermediate Similarity	NPD2800	Approved
0.828	Intermediate Similarity	NPD6232	Discontinued
0.8276	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD3749	Approved
0.8252	Intermediate Similarity	NPD1607	Approved
0.8231	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD1549	Phase 2
0.8207	Intermediate Similarity	NPD1551	Phase 2
0.8194	Intermediate Similarity	NPD3882	Suspended
0.8188	Intermediate Similarity	NPD1511	Approved
0.8146	Intermediate Similarity	NPD920	Approved
0.8133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7473	Discontinued
0.8117	Intermediate Similarity	NPD1934	Approved
0.8108	Intermediate Similarity	NPD3750	Approved
0.8082	Intermediate Similarity	NPD2935	Discontinued
0.8079	Intermediate Similarity	NPD1512	Approved
0.8067	Intermediate Similarity	NPD6799	Approved
0.8065	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2801	Approved
0.8041	Intermediate Similarity	NPD1243	Approved
0.8013	Intermediate Similarity	NPD3817	Phase 2
0.8013	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6959	Discontinued
0.7972	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1465	Phase 2
0.7941	Intermediate Similarity	NPD9545	Approved
0.7935	Intermediate Similarity	NPD7411	Suspended
0.7931	Intermediate Similarity	NPD447	Suspended
0.7914	Intermediate Similarity	NPD9717	Approved
0.7911	Intermediate Similarity	NPD7075	Discontinued
0.7891	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD4380	Phase 2
0.7871	Intermediate Similarity	NPD6599	Discontinued
0.7853	Intermediate Similarity	NPD3818	Discontinued
0.7848	Intermediate Similarity	NPD7768	Phase 2
0.7838	Intermediate Similarity	NPD2796	Approved
0.7834	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD3226	Approved
0.7794	Intermediate Similarity	NPD9493	Approved
0.7785	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD3748	Approved
0.775	Intermediate Similarity	NPD919	Approved
0.7746	Intermediate Similarity	NPD1203	Approved
0.773	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD411	Approved
0.7724	Intermediate Similarity	NPD3764	Approved
0.7714	Intermediate Similarity	NPD422	Phase 1
0.7702	Intermediate Similarity	NPD5494	Approved
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7688	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2654	Approved
0.7673	Intermediate Similarity	NPD5402	Approved
0.7667	Intermediate Similarity	NPD2344	Approved
0.7667	Intermediate Similarity	NPD2346	Discontinued
0.7662	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD9269	Phase 2
0.7658	Intermediate Similarity	NPD37	Approved
0.7658	Intermediate Similarity	NPD6801	Discontinued
0.764	Intermediate Similarity	NPD6234	Discontinued
0.7635	Intermediate Similarity	NPD6651	Approved
0.7632	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD9268	Approved
0.7625	Intermediate Similarity	NPD4965	Approved
0.7625	Intermediate Similarity	NPD4966	Approved
0.7625	Intermediate Similarity	NPD4967	Phase 2
0.7622	Intermediate Similarity	NPD6166	Phase 2
0.7622	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD943	Approved
0.7607	Intermediate Similarity	NPD7229	Phase 3
0.7603	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7054	Approved
0.7569	Intermediate Similarity	NPD1019	Discontinued
0.7568	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6559	Discontinued
0.7546	Intermediate Similarity	NPD1247	Approved
0.7545	Intermediate Similarity	NPD7074	Phase 3
0.7545	Intermediate Similarity	NPD7472	Approved
0.7535	Intermediate Similarity	NPD1608	Approved
0.7533	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7485	Intermediate Similarity	NPD7286	Phase 2
0.7484	Intermediate Similarity	NPD7390	Discontinued
0.7483	Intermediate Similarity	NPD6100	Approved
0.7483	Intermediate Similarity	NPD6099	Approved
0.7468	Intermediate Similarity	NPD2309	Approved
0.7466	Intermediate Similarity	NPD6832	Phase 2
0.7456	Intermediate Similarity	NPD7251	Discontinued
0.7452	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5403	Approved
0.7439	Intermediate Similarity	NPD7199	Phase 2
0.7436	Intermediate Similarity	NPD5401	Approved
0.7412	Intermediate Similarity	NPD7808	Phase 3
0.7397	Intermediate Similarity	NPD9494	Approved
0.7396	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2313	Discontinued
0.7349	Intermediate Similarity	NPD3926	Phase 2
0.7349	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD17	Approved
0.7324	Intermediate Similarity	NPD4626	Approved
0.7324	Intermediate Similarity	NPD1778	Approved
0.7321	Intermediate Similarity	NPD7228	Approved
0.731	Intermediate Similarity	NPD1283	Approved
0.731	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7033	Discontinued
0.7286	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1470	Approved
0.7257	Intermediate Similarity	NPD4287	Approved
0.7255	Intermediate Similarity	NPD5404	Approved
0.7255	Intermediate Similarity	NPD5408	Approved
0.7255	Intermediate Similarity	NPD5406	Approved
0.7255	Intermediate Similarity	NPD5405	Approved
0.7254	Intermediate Similarity	NPD5691	Approved
0.7251	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1296	Phase 2
0.7239	Intermediate Similarity	NPD4288	Approved
0.7239	Intermediate Similarity	NPD5353	Approved
0.7222	Intermediate Similarity	NPD1610	Phase 2
0.7222	Intermediate Similarity	NPD1201	Approved
0.7219	Intermediate Similarity	NPD3751	Discontinued
0.7208	Intermediate Similarity	NPD6005	Phase 3
0.7208	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1471	Phase 3
0.7208	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6004	Phase 3
0.7208	Intermediate Similarity	NPD6002	Phase 3
0.7208	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD9266	Approved
0.7206	Intermediate Similarity	NPD74	Approved
0.7183	Intermediate Similarity	NPD1548	Phase 1
0.7159	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3496	Discontinued
0.7143	Intermediate Similarity	NPD1164	Approved
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD5242	Approved
0.7133	Intermediate Similarity	NPD3268	Approved
0.7132	Intermediate Similarity	NPD9264	Approved
0.7132	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9263	Approved
0.7132	Intermediate Similarity	NPD9267	Approved
0.7114	Intermediate Similarity	NPD4908	Phase 1
0.7103	Intermediate Similarity	NPD1281	Approved
0.7101	Intermediate Similarity	NPD2403	Approved
0.7095	Intermediate Similarity	NPD2798	Approved
0.7086	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3787	Discontinued
0.7078	Intermediate Similarity	NPD4308	Phase 3
0.7075	Intermediate Similarity	NPD3225	Approved
0.707	Intermediate Similarity	NPD7003	Approved
0.7069	Intermediate Similarity	NPD8312	Approved
0.7069	Intermediate Similarity	NPD8313	Approved
0.7063	Intermediate Similarity	NPD6273	Approved
0.7059	Intermediate Similarity	NPD8151	Discontinued
0.7055	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1481	Phase 2
0.7047	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8434	Phase 2
0.7039	Intermediate Similarity	NPD1613	Approved
0.7039	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4060	Phase 1
0.7039	Intermediate Similarity	NPD2979	Phase 3
0.7035	Intermediate Similarity	NPD1729	Discontinued
0.7025	Intermediate Similarity	NPD6190	Approved
0.702	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4749	Approved
0.7006	Intermediate Similarity	NPD1652	Phase 2
0.7	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5124	Phase 1
0.6993	Remote Similarity	NPD6355	Discontinued
0.6993	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1933	Approved
0.6986	Remote Similarity	NPD3705	Approved
0.6986	Remote Similarity	NPD1535	Discovery
0.6986	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6917	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