NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	230.06
Volume:	227.077
LogP:	2.878
LogD:	2.57
LogS:	-3.259
# Rotatable Bonds:	1
TPSA:	52.58
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.645
Synthetic Accessibility Score:	2.585
Fsp3:	0.154
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.748
MDCK Permeability:	2.3219319700729102e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.691

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	80.03483581542969%
Volume Distribution (VD):	0.693
Pgp-substrate:	15.4055757522583%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.859
CYP2C19-substrate:	0.564
CYP2C9-inhibitor:	0.547
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.541
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.383
CYP3A4-substrate:	0.355

ADMET: Excretion

Clearance (CL):	5.143
Half-life (T1/2):	0.463

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.177
Drug-inuced Liver Injury (DILI):	0.655
AMES Toxicity:	0.368
Rat Oral Acute Toxicity:	0.43
Maximum Recommended Daily Dose:	0.355
Skin Sensitization:	0.362
Carcinogencity:	0.748
Eye Corrosion:	0.006
Eye Irritation:	0.877
Respiratory Toxicity:	0.657

Download Data

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

Natural Product: NPC190572

Natural Product ID:	NPC190572
*Common Name:**	Visnagin
IUPAC Name:	4-methoxy-7-methylfuro[3,2-g]chromen-5-one
Synonyms:	Visnagin
Standard InCHIKey:	NZVQLVGOZRELTG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H10O4/c1-7-5-9(14)12-11(17-7)6-10-8(3-4-16-10)13(12)15-2/h3-6H,1-2H3
SMILES:	COc1c2c(=O)cc(oc2cc2c1cco2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL45176
PubChem CID:	6716
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones [CHEMONTID:0001735] Furanochromones

*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
NPO30530	Cimicifuga dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192237]
NPO30530	Cimicifuga dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22103	Ammi visnaga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22103	Ammi visnaga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30530	Cimicifuga dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22103	Ammi visnaga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22103	Ammi visnaga	Species	Apiaceae	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	2
Ki	2
Others	11
Potency	7

Activity Type	# Activity
Individual Protein	14
ORGANISM	2
Others	5
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1315	Individual Protein	Adenosine A1 receptor	Rattus norvegicus	Inhibition	=	36.0	%	PMID[564754]
NPT218	Individual Protein	Adenosine A3 receptor	Homo sapiens	Ki	=	60000.0	nM	PMID[564754]
NPT1316	Individual Protein	Adenosine A2a receptor	Rattus norvegicus	pKi(uM)	=	-1.63	n.a.	PMID[564755]
NPT218	Individual Protein	Adenosine A3 receptor	Homo sapiens	pKi(uM)	=	-1.78	n.a.	PMID[564755]
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	=	141253.8	nM	PMID[564757]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	1995.3	nM	PMID[564757]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	28183.8	nM	PMID[564757]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	3162.3	nM	PMID[564757]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	7.0	%	PMID[564758]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[564759]
NPT2554	Protein Family	Adenosine A2 receptor	Rattus norvegicus	Ki	=	42400.0	nM	PMID[564754]
NPT2555	Others	Adenosine receptors; A1 & A3	Rattus norvegicus	Ratio	=	2.0	n.a.	PMID[564754]
NPT2	Others	Unspecified		T/C	=	1.42	n.a.	PMID[564756]
NPT2	Others	Unspecified		T/C	=	0.51	n.a.	PMID[564756]
NPT2	Others	Unspecified		T/C	=	1.21	n.a.	PMID[564756]
NPT2	Others	Unspecified		Potency	=	1122.0	nM	PMID[564757]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	16.19	%	PMID[564758]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	98.15	%	PMID[564760]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	127.2	%	PMID[564760]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[564761]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[564761]

☑ 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 NPC190572 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	507
0.1-0.2	1995
0.2-0.3	5146
0.3-0.4	12017
0.4-0.5	5860
0.5-0.6	4975
0.6-0.7	5664
0.7-0.8	4436
0.8-0.85	1553
0.85-0.9	483
0.9-0.95	47
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC135303
0.972	High Similarity	NPC148423
0.9648	High Similarity	NPC198427
0.9586	High Similarity	NPC130015
0.9586	High Similarity	NPC38361
0.958	High Similarity	NPC306788
0.9521	High Similarity	NPC41719
0.9517	High Similarity	NPC472407
0.9514	High Similarity	NPC88445
0.951	High Similarity	NPC304443
0.951	High Similarity	NPC74539
0.9456	High Similarity	NPC233776
0.9452	High Similarity	NPC263676
0.9448	High Similarity	NPC472406
0.9448	High Similarity	NPC191104
0.9371	High Similarity	NPC246903
0.9353	High Similarity	NPC29638
0.9252	High Similarity	NPC116604
0.9236	High Similarity	NPC208584
0.9231	High Similarity	NPC313036
0.9231	High Similarity	NPC166858
0.9231	High Similarity	NPC51146
0.9189	High Similarity	NPC253872
0.9178	High Similarity	NPC266743
0.9145	High Similarity	NPC264293
0.9085	High Similarity	NPC193998
0.9073	High Similarity	NPC269495
0.9067	High Similarity	NPC295608
0.9067	High Similarity	NPC278010
0.9067	High Similarity	NPC250769
0.9054	High Similarity	NPC155882
0.9034	High Similarity	NPC17262
0.9028	High Similarity	NPC254010
0.9026	High Similarity	NPC65846
0.9021	High Similarity	NPC262635
0.9007	High Similarity	NPC160015
0.9007	High Similarity	NPC247677
0.9	High Similarity	NPC131725
0.8986	High Similarity	NPC37226
0.8986	High Similarity	NPC226644
0.8958	High Similarity	NPC28337
0.8954	High Similarity	NPC49009
0.8954	High Similarity	NPC169
0.8947	High Similarity	NPC260902
0.8947	High Similarity	NPC270044
0.8947	High Similarity	NPC296957
0.8933	High Similarity	NPC67654
0.8897	High Similarity	NPC22467
0.8896	High Similarity	NPC14822
0.8896	High Similarity	NPC304387
0.8889	High Similarity	NPC476349
0.8889	High Similarity	NPC476350
0.8874	High Similarity	NPC213608
0.8874	High Similarity	NPC1477
0.8874	High Similarity	NPC122365
0.8867	High Similarity	NPC156244
0.8867	High Similarity	NPC170169
0.8865	High Similarity	NPC247743
0.8859	High Similarity	NPC296030
0.8859	High Similarity	NPC39929
0.8859	High Similarity	NPC317492
0.8851	High Similarity	NPC12148
0.8851	High Similarity	NPC130581
0.8846	High Similarity	NPC38914
0.8839	High Similarity	NPC219861
0.8836	High Similarity	NPC53192
0.8831	High Similarity	NPC95472
0.8831	High Similarity	NPC239270
0.8831	High Similarity	NPC303210
0.8828	High Similarity	NPC470856
0.8824	High Similarity	NPC65504
0.8816	High Similarity	NPC198490
0.8811	High Similarity	NPC254741
0.8808	High Similarity	NPC5871
0.88	High Similarity	NPC78335
0.88	High Similarity	NPC230713
0.8797	High Similarity	NPC41853
0.8794	High Similarity	NPC229646
0.8792	High Similarity	NPC135325
0.8792	High Similarity	NPC168085
0.8784	High Similarity	NPC210826
0.8784	High Similarity	NPC300267
0.8784	High Similarity	NPC51641
0.8782	High Similarity	NPC179464
0.8776	High Similarity	NPC225884
0.8776	High Similarity	NPC302181
0.8766	High Similarity	NPC33320
0.8759	High Similarity	NPC137009
0.875	High Similarity	NPC183874
0.875	High Similarity	NPC472462
0.8742	High Similarity	NPC98028
0.8734	High Similarity	NPC167479
0.8734	High Similarity	NPC241820
0.8733	High Similarity	NPC221868
0.8733	High Similarity	NPC37208
0.8733	High Similarity	NPC178202
0.8732	High Similarity	NPC292998
0.8725	High Similarity	NPC17816
0.8718	High Similarity	NPC234536
0.8718	High Similarity	NPC78612
0.8716	High Similarity	NPC179970
0.8716	High Similarity	NPC155144
0.8716	High Similarity	NPC230943
0.8716	High Similarity	NPC98926
0.871	High Similarity	NPC243509
0.8705	High Similarity	NPC50583
0.8693	High Similarity	NPC473193
0.8693	High Similarity	NPC148938
0.869	High Similarity	NPC36414
0.8681	High Similarity	NPC161196
0.8681	High Similarity	NPC222633
0.8681	High Similarity	NPC472516
0.8671	High Similarity	NPC155264
0.8671	High Similarity	NPC193881
0.8671	High Similarity	NPC67450
0.8671	High Similarity	NPC210460
0.8667	High Similarity	NPC272194
0.8662	High Similarity	NPC109180
0.8662	High Similarity	NPC182428
0.8662	High Similarity	NPC472581
0.8654	High Similarity	NPC216092
0.8645	High Similarity	NPC40583
0.8645	High Similarity	NPC250076
0.8634	High Similarity	NPC62640
0.8633	High Similarity	NPC49852
0.8633	High Similarity	NPC475496
0.863	High Similarity	NPC472515
0.863	High Similarity	NPC37206
0.863	High Similarity	NPC136095
0.863	High Similarity	NPC11566
0.8627	High Similarity	NPC235333
0.8627	High Similarity	NPC473194
0.8625	High Similarity	NPC190351
0.8621	High Similarity	NPC253616
0.8621	High Similarity	NPC259685
0.8618	High Similarity	NPC115324
0.8611	High Similarity	NPC60667
0.8611	High Similarity	NPC46869
0.8608	High Similarity	NPC136641
0.8601	High Similarity	NPC223354
0.86	High Similarity	NPC471285
0.8592	High Similarity	NPC284424
0.8592	High Similarity	NPC278556
0.8591	High Similarity	NPC271590
0.8591	High Similarity	NPC234629
0.8591	High Similarity	NPC311741
0.8591	High Similarity	NPC110776
0.8591	High Similarity	NPC297788
0.8581	High Similarity	NPC96342
0.8581	High Similarity	NPC164110
0.8581	High Similarity	NPC212967
0.8581	High Similarity	NPC246647
0.8581	High Similarity	NPC268360
0.8581	High Similarity	NPC162476
0.8571	High Similarity	NPC157522
0.8571	High Similarity	NPC101366
0.8571	High Similarity	NPC213936
0.8571	High Similarity	NPC473907
0.8571	High Similarity	NPC297531
0.8571	High Similarity	NPC472409
0.8562	High Similarity	NPC327269
0.8562	High Similarity	NPC207624
0.8562	High Similarity	NPC31627
0.8562	High Similarity	NPC17848
0.8562	High Similarity	NPC476238
0.8553	High Similarity	NPC321896
0.8553	High Similarity	NPC472421
0.8553	High Similarity	NPC167576
0.8553	High Similarity	NPC476185
0.8552	High Similarity	NPC268081
0.8543	High Similarity	NPC39195
0.8543	High Similarity	NPC266572
0.8542	High Similarity	NPC125269
0.8542	High Similarity	NPC125920
0.8533	High Similarity	NPC476153
0.8533	High Similarity	NPC215885
0.8533	High Similarity	NPC2416
0.8531	High Similarity	NPC101294
0.8531	High Similarity	NPC473655
0.8526	High Similarity	NPC472877
0.8523	High Similarity	NPC59522
0.8516	High Similarity	NPC470625
0.8516	High Similarity	NPC180924
0.8514	High Similarity	NPC55832
0.8514	High Similarity	NPC3188
0.8514	High Similarity	NPC26051
0.8514	High Similarity	NPC268204
0.8514	High Similarity	NPC469404
0.8514	High Similarity	NPC52789
0.8514	High Similarity	NPC110969
0.8514	High Similarity	NPC171870
0.8514	High Similarity	NPC103362
0.8511	High Similarity	NPC473894
0.8506	High Similarity	NPC42458
0.8506	High Similarity	NPC158261
0.8506	High Similarity	NPC72370
0.8503	High Similarity	NPC23257
0.8503	High Similarity	NPC295384
0.8503	High Similarity	NPC473076
0.8503	High Similarity	NPC18260

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 NPC190572 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	432
0.1-0.2	1018
0.2-0.3	1715
0.3-0.4	2814
0.4-0.5	1829
0.5-0.6	935
0.6-0.7	271
0.7-0.8	100
0.8-0.85	27
0.85-0.9	3
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.951	High Similarity	NPD920	Approved
0.9371	High Similarity	NPD642	Clinical (unspecified phase)
0.9231	High Similarity	NPD643	Clinical (unspecified phase)
0.9145	High Similarity	NPD1247	Approved
0.9021	High Similarity	NPD1243	Approved
0.8766	High Similarity	NPD919	Approved
0.8681	High Similarity	NPD2796	Approved
0.8467	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD1510	Phase 2
0.8311	Intermediate Similarity	NPD1549	Phase 2
0.8258	Intermediate Similarity	NPD7411	Suspended
0.8243	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD5494	Approved
0.8207	Intermediate Similarity	NPD1240	Approved
0.8133	Intermediate Similarity	NPD2800	Approved
0.8105	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1607	Approved
0.8077	Intermediate Similarity	NPD4380	Phase 2
0.8039	Intermediate Similarity	NPD6799	Approved
0.8038	Intermediate Similarity	NPD7819	Suspended
0.8038	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1471	Phase 3
0.8	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD2344	Approved
0.7975	Intermediate Similarity	NPD3926	Phase 2
0.7975	Intermediate Similarity	NPD6801	Discontinued
0.7964	Intermediate Similarity	NPD6559	Discontinued
0.7937	Intermediate Similarity	NPD3882	Suspended
0.7933	Intermediate Similarity	NPD1551	Phase 2
0.7927	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1511	Approved
0.7895	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7075	Discontinued
0.7881	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD3748	Approved
0.7862	Intermediate Similarity	NPD1934	Approved
0.7848	Intermediate Similarity	NPD6599	Discontinued
0.7831	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1512	Approved
0.7812	Intermediate Similarity	NPD2801	Approved
0.7792	Intermediate Similarity	NPD2309	Approved
0.7778	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3817	Phase 2
0.7756	Intermediate Similarity	NPD2532	Approved
0.7756	Intermediate Similarity	NPD2534	Approved
0.7756	Intermediate Similarity	NPD2533	Approved
0.7725	Intermediate Similarity	NPD3818	Discontinued
0.7716	Intermediate Similarity	NPD7768	Phase 2
0.7712	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2313	Discontinued
0.7692	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6959	Discontinued
0.7632	Intermediate Similarity	NPD2799	Discontinued
0.7613	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD3750	Approved
0.759	Intermediate Similarity	NPD6808	Phase 2
0.7584	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6832	Phase 2
0.7562	Intermediate Similarity	NPD3226	Approved
0.7548	Intermediate Similarity	NPD2654	Approved
0.7532	Intermediate Similarity	NPD5401	Approved
0.7531	Intermediate Similarity	NPD6280	Approved
0.7531	Intermediate Similarity	NPD6279	Approved
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2403	Approved
0.7485	Intermediate Similarity	NPD5953	Discontinued
0.7471	Intermediate Similarity	NPD7286	Phase 2
0.7468	Intermediate Similarity	NPD2935	Discontinued
0.7439	Intermediate Similarity	NPD5402	Approved
0.7438	Intermediate Similarity	NPD5403	Approved
0.7434	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1019	Discontinued
0.7429	Intermediate Similarity	NPD1241	Discontinued
0.7396	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6166	Phase 2
0.7386	Intermediate Similarity	NPD6651	Approved
0.7381	Intermediate Similarity	NPD6232	Discontinued
0.7365	Intermediate Similarity	NPD3266	Approved
0.7365	Intermediate Similarity	NPD3267	Approved
0.7353	Intermediate Similarity	NPD7473	Discontinued
0.7351	Intermediate Similarity	NPD1296	Phase 2
0.7329	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD1729	Discontinued
0.7308	Intermediate Similarity	NPD2346	Discontinued
0.7305	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD9717	Approved
0.7267	Intermediate Similarity	NPD5844	Phase 1
0.7267	Intermediate Similarity	NPD7054	Approved
0.7256	Intermediate Similarity	NPD5890	Approved
0.7256	Intermediate Similarity	NPD5889	Approved
0.7255	Intermediate Similarity	NPD943	Approved
0.7248	Intermediate Similarity	NPD1203	Approved
0.7232	Intermediate Similarity	NPD8434	Phase 2
0.7229	Intermediate Similarity	NPD2296	Approved
0.7225	Intermediate Similarity	NPD7074	Phase 3
0.7225	Intermediate Similarity	NPD7472	Approved
0.72	Intermediate Similarity	NPD2798	Approved
0.7184	Intermediate Similarity	NPD6797	Phase 2
0.7176	Intermediate Similarity	NPD7229	Phase 3
0.7176	Intermediate Similarity	NPD5711	Approved
0.7176	Intermediate Similarity	NPD5710	Approved
0.717	Intermediate Similarity	NPD4628	Phase 3
0.7169	Intermediate Similarity	NPD5761	Phase 2
0.7169	Intermediate Similarity	NPD5760	Phase 2
0.7162	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD4307	Phase 2
0.7143	Intermediate Similarity	NPD7251	Discontinued
0.7124	Intermediate Similarity	NPD3268	Approved
0.7102	Intermediate Similarity	NPD7808	Phase 3
0.7102	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD447	Suspended
0.7097	Intermediate Similarity	NPD1933	Approved
0.7097	Intermediate Similarity	NPD230	Phase 1
0.7095	Intermediate Similarity	NPD422	Phase 1
0.7091	Intermediate Similarity	NPD6585	Discontinued
0.7075	Intermediate Similarity	NPD17	Approved
0.707	Intermediate Similarity	NPD7033	Discontinued
0.7067	Intermediate Similarity	NPD1876	Approved
0.7066	Intermediate Similarity	NPD1465	Phase 2
0.7056	Intermediate Similarity	NPD4287	Approved
0.7055	Intermediate Similarity	NPD1548	Phase 1
0.7049	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4361	Phase 2
0.7013	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4363	Phase 3
0.6995	Remote Similarity	NPD4360	Phase 2
0.6993	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1610	Phase 2
0.6962	Remote Similarity	NPD4308	Phase 3
0.6946	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD9545	Approved
0.6937	Remote Similarity	NPD2424	Discontinued
0.6933	Remote Similarity	NPD7390	Discontinued
0.6933	Remote Similarity	NPD1608	Approved
0.6923	Remote Similarity	NPD3142	Approved
0.6923	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4288	Approved
0.6923	Remote Similarity	NPD3140	Approved
0.6903	Remote Similarity	NPD411	Approved
0.6898	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1651	Approved
0.6883	Remote Similarity	NPD4908	Phase 1
0.6879	Remote Similarity	NPD5124	Phase 1
0.6879	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6104	Discontinued
0.6852	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3225	Approved
0.6839	Remote Similarity	NPD5242	Approved
0.6828	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3751	Discontinued
0.6818	Remote Similarity	NPD2163	Approved
0.6818	Remote Similarity	NPD9494	Approved
0.6813	Remote Similarity	NPD6099	Approved
0.6813	Remote Similarity	NPD6100	Approved
0.681	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3887	Approved
0.6805	Remote Similarity	NPD6844	Discontinued
0.6803	Remote Similarity	NPD9493	Approved
0.6797	Remote Similarity	NPD2797	Approved
0.6797	Remote Similarity	NPD1164	Approved
0.6795	Remote Similarity	NPD3764	Approved
0.6788	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6002	Phase 3
0.677	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2353	Approved
0.677	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6005	Phase 3
0.677	Remote Similarity	NPD6004	Phase 3
0.677	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.676	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1281	Approved
0.6726	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7458	Discontinued
0.6725	Remote Similarity	NPD5353	Approved
0.6724	Remote Similarity	NPD7199	Phase 2
0.6709	Remote Similarity	NPD1613	Approved
0.6709	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2979	Phase 3
0.6705	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1470	Approved
0.6687	Remote Similarity	NPD4662	Approved
0.6687	Remote Similarity	NPD1652	Phase 2
0.6687	Remote Similarity	NPD4661	Approved
0.6686	Remote Similarity	NPD3787	Discontinued
0.6686	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4947	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