NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	247.12
Volume:	251.852
LogP:	2.518
LogD:	2.141
LogS:	-3.002
# Rotatable Bonds:	3
TPSA:	38.77
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.767
Synthetic Accessibility Score:	1.899
Fsp3:	0.5
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:	-4.615
MDCK Permeability:	4.0623250242788345e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	47.572059631347656%
Volume Distribution (VD):	2.379
Pgp-substrate:	28.191740036010742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.906
CYP1A2-substrate:	0.436
CYP2C19-inhibitor:	0.542
CYP2C19-substrate:	0.532
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.104
CYP2D6-inhibitor:	0.979
CYP2D6-substrate:	0.852
CYP3A4-inhibitor:	0.721
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	16.19
Half-life (T1/2):	0.574

ADMET: Toxicity

hERG Blockers:	0.448
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.456
AMES Toxicity:	0.313
Rat Oral Acute Toxicity:	0.667
Maximum Recommended Daily Dose:	0.148
Skin Sensitization:	0.361
Carcinogencity:	0.791
Eye Corrosion:	0.018
Eye Irritation:	0.062
Respiratory Toxicity:	0.87

Download Data

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

Natural Product: NPC470088

Natural Product ID:	NPC470088
*Common Name:**	GUAGHEHHFOGEPB-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GUAGHEHHFOGEPB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H17NO3.ClH/c16-12(9-15-6-2-1-3-7-15)11-4-5-13-14(8-11)18-10-17-13;/h4-5,8H,1-3,6-7,9-10H2;1H
SMILES:	O=C(c1ccc2c(c1)OCO2)CN1CCCCC1.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1712955
PubChem CID:	44655462 16682281
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4039(01)00209-X]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10575373]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15467205]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16808005]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23102654]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31103896]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28928	Piper nigrum	Species	Piperaceae	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
Potency	4

Activity Type	# Activity
Individual Protein	5
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[505502]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	10318.3	nM	PMID[505502]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[505502]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	3180.0	nM	PMID[505503]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	>	100000.0	nM	PMID[505503]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2616.9	nM	PMID[505502]

☑ 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 NPC470088 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	297
0.1-0.2	1477
0.2-0.3	5578
0.3-0.4	12350
0.4-0.5	4515
0.5-0.6	10746
0.6-0.7	7313
0.7-0.8	387
0.8-0.85	29
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9574	High Similarity	NPC469978
0.8684	High Similarity	NPC470708
0.8552	High Similarity	NPC225745
0.8447	Intermediate Similarity	NPC67978
0.8447	Intermediate Similarity	NPC303581
0.844	Intermediate Similarity	NPC286683
0.8438	Intermediate Similarity	NPC86469
0.8425	Intermediate Similarity	NPC252107
0.8414	Intermediate Similarity	NPC180647
0.8356	Intermediate Similarity	NPC99078
0.8345	Intermediate Similarity	NPC167096
0.8344	Intermediate Similarity	NPC308267
0.8322	Intermediate Similarity	NPC138438
0.8322	Intermediate Similarity	NPC908
0.8312	Intermediate Similarity	NPC119669
0.8301	Intermediate Similarity	NPC469539
0.8301	Intermediate Similarity	NPC469540
0.8299	Intermediate Similarity	NPC220923
0.8288	Intermediate Similarity	NPC196609
0.8288	Intermediate Similarity	NPC251454
0.8288	Intermediate Similarity	NPC73883
0.8288	Intermediate Similarity	NPC136330
0.8288	Intermediate Similarity	NPC255817
0.8288	Intermediate Similarity	NPC277042
0.8288	Intermediate Similarity	NPC230698
0.8288	Intermediate Similarity	NPC205178
0.8176	Intermediate Similarity	NPC470707
0.8176	Intermediate Similarity	NPC28641
0.8176	Intermediate Similarity	NPC194359
0.8133	Intermediate Similarity	NPC121400
0.8042	Intermediate Similarity	NPC120066
0.8012	Intermediate Similarity	NPC153631
0.7987	Intermediate Similarity	NPC7018
0.7987	Intermediate Similarity	NPC145446
0.7987	Intermediate Similarity	NPC137172
0.7976	Intermediate Similarity	NPC27887
0.795	Intermediate Similarity	NPC26353
0.795	Intermediate Similarity	NPC135006
0.7943	Intermediate Similarity	NPC225245
0.7933	Intermediate Similarity	NPC95366
0.7933	Intermediate Similarity	NPC248505
0.7925	Intermediate Similarity	NPC169742
0.7919	Intermediate Similarity	NPC96406
0.7914	Intermediate Similarity	NPC35345
0.7907	Intermediate Similarity	NPC141440
0.7904	Intermediate Similarity	NPC207721
0.7902	Intermediate Similarity	NPC474691
0.7898	Intermediate Similarity	NPC223125
0.7895	Intermediate Similarity	NPC18306
0.7867	Intermediate Similarity	NPC416184
0.7857	Intermediate Similarity	NPC125134
0.7857	Intermediate Similarity	NPC137920
0.7857	Intermediate Similarity	NPC86455
0.7853	Intermediate Similarity	NPC207239
0.7852	Intermediate Similarity	NPC45783
0.7852	Intermediate Similarity	NPC328419
0.7852	Intermediate Similarity	NPC103947
0.7852	Intermediate Similarity	NPC94280
0.7852	Intermediate Similarity	NPC159150
0.7852	Intermediate Similarity	NPC193673
0.7843	Intermediate Similarity	NPC28398
0.7838	Intermediate Similarity	NPC217574
0.7838	Intermediate Similarity	NPC318862
0.7836	Intermediate Similarity	NPC116007
0.7806	Intermediate Similarity	NPC46880
0.7799	Intermediate Similarity	NPC223124
0.7778	Intermediate Similarity	NPC106786
0.7771	Intermediate Similarity	NPC153644
0.777	Intermediate Similarity	NPC477694
0.777	Intermediate Similarity	NPC477705
0.7756	Intermediate Similarity	NPC327052
0.7751	Intermediate Similarity	NPC35680
0.7748	Intermediate Similarity	NPC469808
0.7746	Intermediate Similarity	NPC169387
0.7746	Intermediate Similarity	NPC477259
0.7744	Intermediate Similarity	NPC59567
0.7733	Intermediate Similarity	NPC83511
0.7724	Intermediate Similarity	NPC30216
0.7718	Intermediate Similarity	NPC477706
0.7697	Intermediate Similarity	NPC306669
0.7697	Intermediate Similarity	NPC71124
0.7688	Intermediate Similarity	NPC58661
0.7688	Intermediate Similarity	NPC471073
0.7688	Intermediate Similarity	NPC270811
0.7682	Intermediate Similarity	NPC45404
0.7679	Intermediate Similarity	NPC227683
0.767	Intermediate Similarity	NPC254957
0.7658	Intermediate Similarity	NPC153620
0.7658	Intermediate Similarity	NPC24257
0.7658	Intermediate Similarity	NPC475959
0.7654	Intermediate Similarity	NPC5374
0.7647	Intermediate Similarity	NPC5167
0.7647	Intermediate Similarity	NPC85613
0.7643	Intermediate Similarity	NPC229787
0.7633	Intermediate Similarity	NPC329992
0.7614	Intermediate Similarity	NPC226708
0.7595	Intermediate Similarity	NPC296575
0.7595	Intermediate Similarity	NPC224687
0.7586	Intermediate Similarity	NPC256167
0.7584	Intermediate Similarity	NPC33256
0.7584	Intermediate Similarity	NPC160193
0.7569	Intermediate Similarity	NPC295317
0.7568	Intermediate Similarity	NPC16651
0.7568	Intermediate Similarity	NPC32163
0.7568	Intermediate Similarity	NPC64948
0.7562	Intermediate Similarity	NPC478189
0.755	Intermediate Similarity	NPC153453
0.7543	Intermediate Similarity	NPC471650
0.7532	Intermediate Similarity	NPC231572
0.7529	Intermediate Similarity	NPC4669
0.7516	Intermediate Similarity	NPC38101
0.7514	Intermediate Similarity	NPC63152
0.75	Intermediate Similarity	NPC154275
0.7486	Intermediate Similarity	NPC207971
0.7486	Intermediate Similarity	NPC477258
0.7485	Intermediate Similarity	NPC231198
0.7471	Intermediate Similarity	NPC102760
0.7469	Intermediate Similarity	NPC148898
0.7468	Intermediate Similarity	NPC145304
0.7468	Intermediate Similarity	NPC230968
0.7468	Intermediate Similarity	NPC102260
0.7466	Intermediate Similarity	NPC298486
0.7457	Intermediate Similarity	NPC149285
0.7451	Intermediate Similarity	NPC11147
0.745	Intermediate Similarity	NPC172403
0.7446	Intermediate Similarity	NPC268077
0.7444	Intermediate Similarity	NPC24228
0.7443	Intermediate Similarity	NPC162694
0.744	Intermediate Similarity	NPC474858
0.7438	Intermediate Similarity	NPC59907
0.7438	Intermediate Similarity	NPC37144
0.7436	Intermediate Similarity	NPC470855
0.7434	Intermediate Similarity	NPC266425
0.7432	Intermediate Similarity	NPC473626
0.743	Intermediate Similarity	NPC469815
0.743	Intermediate Similarity	NPC469816
0.7425	Intermediate Similarity	NPC476569
0.7414	Intermediate Similarity	NPC473562
0.7407	Intermediate Similarity	NPC205054
0.7407	Intermediate Similarity	NPC37220
0.7407	Intermediate Similarity	NPC476579
0.7405	Intermediate Similarity	NPC472564
0.7403	Intermediate Similarity	NPC124302
0.7403	Intermediate Similarity	NPC95485
0.7403	Intermediate Similarity	NPC89504
0.7403	Intermediate Similarity	NPC88065
0.7403	Intermediate Similarity	NPC70290
0.7403	Intermediate Similarity	NPC215098
0.7403	Intermediate Similarity	NPC46744
0.7403	Intermediate Similarity	NPC73020
0.7403	Intermediate Similarity	NPC14622
0.7396	Intermediate Similarity	NPC284842
0.7389	Intermediate Similarity	NPC125924
0.7378	Intermediate Similarity	NPC308555
0.7378	Intermediate Similarity	NPC93593
0.7378	Intermediate Similarity	NPC138487
0.7378	Intermediate Similarity	NPC78733
0.7378	Intermediate Similarity	NPC216459
0.7378	Intermediate Similarity	NPC41178
0.7368	Intermediate Similarity	NPC118419
0.7362	Intermediate Similarity	NPC233029
0.7362	Intermediate Similarity	NPC210148
0.7345	Intermediate Similarity	NPC474009
0.7343	Intermediate Similarity	NPC111225
0.7342	Intermediate Similarity	NPC104956
0.7341	Intermediate Similarity	NPC283810
0.7341	Intermediate Similarity	NPC222524
0.7337	Intermediate Similarity	NPC206941
0.7333	Intermediate Similarity	NPC478213
0.7333	Intermediate Similarity	NPC31311
0.7333	Intermediate Similarity	NPC146288
0.7333	Intermediate Similarity	NPC234392
0.7333	Intermediate Similarity	NPC57512
0.7333	Intermediate Similarity	NPC244371
0.7329	Intermediate Similarity	NPC214239
0.7322	Intermediate Similarity	NPC120671
0.7322	Intermediate Similarity	NPC72788
0.7322	Intermediate Similarity	NPC314100
0.7322	Intermediate Similarity	NPC226652
0.732	Intermediate Similarity	NPC50763
0.7317	Intermediate Similarity	NPC220577
0.7312	Intermediate Similarity	NPC290404
0.731	Intermediate Similarity	NPC69670
0.7305	Intermediate Similarity	NPC158900
0.7303	Intermediate Similarity	NPC285776
0.7303	Intermediate Similarity	NPC66905
0.7301	Intermediate Similarity	NPC8337
0.7301	Intermediate Similarity	NPC85747
0.7301	Intermediate Similarity	NPC227980
0.7299	Intermediate Similarity	NPC329816
0.7296	Intermediate Similarity	NPC244338
0.7292	Intermediate Similarity	NPC199209
0.7292	Intermediate Similarity	NPC212643
0.7289	Intermediate Similarity	NPC3273
0.7289	Intermediate Similarity	NPC254163
0.7288	Intermediate Similarity	NPC214629
0.7286	Intermediate Similarity	NPC31279
0.7284	Intermediate Similarity	NPC211296
0.7278	Intermediate Similarity	NPC51681
0.7273	Intermediate Similarity	NPC153008

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 NPC470088 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	758
0.2-0.3	1105
0.3-0.4	2205
0.4-0.5	2553
0.5-0.6	1639
0.6-0.7	637
0.7-0.8	55
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8288	Intermediate Similarity	NPD2492	Phase 1
0.828	Intermediate Similarity	NPD5978	Approved
0.828	Intermediate Similarity	NPD5977	Approved
0.8258	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD6385	Approved
0.8089	Intermediate Similarity	NPD6386	Approved
0.8027	Intermediate Similarity	NPD3140	Approved
0.8027	Intermediate Similarity	NPD3142	Approved
0.7962	Intermediate Similarity	NPD824	Approved
0.7806	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7110	Phase 1
0.775	Intermediate Similarity	NPD6873	Phase 2
0.775	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5718	Phase 2
0.7632	Intermediate Similarity	NPD743	Approved
0.7628	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3640	Phase 3
0.761	Intermediate Similarity	NPD3641	Approved
0.761	Intermediate Similarity	NPD3639	Approved
0.7607	Intermediate Similarity	NPD5353	Approved
0.7517	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6876	Approved
0.7469	Intermediate Similarity	NPD6875	Approved
0.7418	Intermediate Similarity	NPD5457	Discontinued
0.7403	Intermediate Similarity	NPD4420	Approved
0.7396	Intermediate Similarity	NPD5242	Approved
0.7391	Intermediate Similarity	NPD1670	Discontinued
0.7351	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4413	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7281	Phase 3
0.7314	Intermediate Similarity	NPD7280	Phase 3
0.7312	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5297	Approved
0.7278	Intermediate Similarity	NPD2654	Approved
0.7244	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD5006	Approved
0.7243	Intermediate Similarity	NPD5005	Approved
0.7226	Intermediate Similarity	NPD2653	Approved
0.7219	Intermediate Similarity	NPD9494	Approved
0.7216	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1307	Phase 2
0.7202	Intermediate Similarity	NPD1309	Phase 2
0.7186	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6895	Approved
0.7179	Intermediate Similarity	NPD6896	Approved
0.7175	Intermediate Similarity	NPD6618	Phase 2
0.716	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3146	Approved
0.7151	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4107	Approved
0.7119	Intermediate Similarity	NPD2968	Approved
0.7119	Intermediate Similarity	NPD2971	Approved
0.7102	Intermediate Similarity	NPD7039	Approved
0.7102	Intermediate Similarity	NPD7038	Approved
0.7073	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2822	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6844	Discontinued
0.7066	Intermediate Similarity	NPD7577	Discontinued
0.7056	Intermediate Similarity	NPD7291	Discontinued
0.7055	Intermediate Similarity	NPD5536	Phase 2
0.7048	Intermediate Similarity	NPD2592	Discontinued
0.7045	Intermediate Similarity	NPD6297	Approved
0.7043	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2978	Approved
0.7024	Intermediate Similarity	NPD2977	Approved
0.7005	Intermediate Similarity	NPD4482	Phase 3
0.7	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3455	Phase 2
0.6983	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3057	Approved
0.6964	Remote Similarity	NPD6280	Approved
0.6964	Remote Similarity	NPD6279	Approved
0.6954	Remote Similarity	NPD2898	Approved
0.6954	Remote Similarity	NPD1755	Approved
0.6951	Remote Similarity	NPD4584	Approved
0.6935	Remote Similarity	NPD5071	Phase 2
0.6928	Remote Similarity	NPD4210	Discontinued
0.6923	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5604	Discontinued
0.6889	Remote Similarity	NPD6851	Approved
0.6889	Remote Similarity	NPD6853	Approved
0.6887	Remote Similarity	NPD3972	Approved
0.6886	Remote Similarity	NPD2649	Approved
0.6886	Remote Similarity	NPD2651	Approved
0.6885	Remote Similarity	NPD2488	Approved
0.6885	Remote Similarity	NPD2490	Approved
0.6882	Remote Similarity	NPD5564	Approved
0.6879	Remote Similarity	NPD6107	Approved
0.6878	Remote Similarity	NPD2491	Approved
0.6878	Remote Similarity	NPD3533	Approved
0.6878	Remote Similarity	NPD3448	Approved
0.6878	Remote Similarity	NPD2972	Approved
0.6875	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3818	Discontinued
0.6875	Remote Similarity	NPD2163	Approved
0.6871	Remote Similarity	NPD5241	Discontinued
0.6864	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6862	Phase 2
0.6852	Remote Similarity	NPD4236	Phase 3
0.6852	Remote Similarity	NPD3060	Approved
0.6852	Remote Similarity	NPD4237	Approved
0.6852	Remote Similarity	NPD4162	Approved
0.6848	Remote Similarity	NPD1424	Approved
0.6839	Remote Similarity	NPD4166	Phase 2
0.6839	Remote Similarity	NPD5186	Approved
0.6839	Remote Similarity	NPD5183	Approved
0.6836	Remote Similarity	NPD5313	Approved
0.6836	Remote Similarity	NPD5312	Approved
0.6835	Remote Similarity	NPD1933	Approved
0.6832	Remote Similarity	NPD1375	Discontinued
0.6829	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7124	Phase 2
0.6828	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2245	Discovery
0.6813	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5890	Approved
0.6805	Remote Similarity	NPD5889	Approved
0.6798	Remote Similarity	NPD3885	Approved
0.6798	Remote Similarity	NPD2325	Approved
0.6792	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2975	Approved
0.6791	Remote Similarity	NPD2974	Approved
0.6791	Remote Similarity	NPD2973	Approved
0.6786	Remote Similarity	NPD4017	Approved
0.6781	Remote Similarity	NPD1241	Discontinued
0.6769	Remote Similarity	NPD683	Approved
0.6766	Remote Similarity	NPD6030	Approved
0.6766	Remote Similarity	NPD6031	Approved
0.6761	Remote Similarity	NPD4481	Phase 3
0.6761	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7296	Approved
0.6748	Remote Similarity	NPD5177	Phase 3
0.6747	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6585	Discontinued
0.6746	Remote Similarity	NPD7028	Phase 2
0.6744	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3882	Suspended
0.6743	Remote Similarity	NPD6808	Phase 2
0.6733	Remote Similarity	NPD1357	Approved
0.6733	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3686	Approved
0.6726	Remote Similarity	NPD3687	Approved
0.6724	Remote Similarity	NPD5677	Discontinued
0.6724	Remote Similarity	NPD5494	Approved
0.6718	Remote Similarity	NPD5914	Approved
0.6711	Remote Similarity	NPD3705	Approved
0.671	Remote Similarity	NPD7905	Discontinued
0.6709	Remote Similarity	NPD2674	Phase 3
0.6707	Remote Similarity	NPD2186	Approved
0.6705	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5950	Discontinued
0.6701	Remote Similarity	NPD4859	Phase 1
0.6689	Remote Similarity	NPD2667	Approved
0.6689	Remote Similarity	NPD2668	Approved
0.6688	Remote Similarity	NPD1876	Approved
0.6688	Remote Similarity	NPD196	Phase 1
0.6688	Remote Similarity	NPD5746	Approved
0.6686	Remote Similarity	NPD5967	Approved
0.6686	Remote Similarity	NPD2821	Approved
0.6685	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4580	Approved
0.6684	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3382	Approved
0.6667	Remote Similarity	NPD3383	Approved
0.6667	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3384	Approved
0.6667	Remote Similarity	NPD7427	Discontinued
0.6667	Remote Similarity	NPD7317	Phase 3
0.6649	Remote Similarity	NPD3452	Approved
0.6649	Remote Similarity	NPD2493	Approved
0.6649	Remote Similarity	NPD2494	Approved
0.6649	Remote Similarity	NPD3450	Approved
0.6647	Remote Similarity	NPD4662	Approved
0.6647	Remote Similarity	NPD4661	Approved
0.6647	Remote Similarity	NPD4739	Approved
0.6646	Remote Similarity	NPD2569	Approved
0.6646	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6111	Discontinued
0.6646	Remote Similarity	NPD2567	Approved
0.663	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.663	Remote Similarity	NPD1298	Discontinued
0.6628	Remote Similarity	NPD5772	Approved
0.6628	Remote Similarity	NPD5773	Approved
0.6628	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4618	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