NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	109.05
Volume:	115.654
LogP:	0.141
LogD:	0.454
LogS:	-0.871
# Rotatable Bonds:	0
TPSA:	46.25
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.385
Synthetic Accessibility Score:	1.598
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.302
MDCK Permeability:	1.609472747077234e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.921
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.138
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	29.92412757873535%
Volume Distribution (VD):	1.586
Pgp-substrate:	69.83393859863281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.342
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.228
CYP2C19-substrate:	0.165
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.786
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.829
CYP3A4-inhibitor:	0.133
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	12.133
Half-life (T1/2):	0.698

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.062
Drug-inuced Liver Injury (DILI):	0.109
AMES Toxicity:	0.857
Rat Oral Acute Toxicity:	0.863
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.916
Carcinogencity:	0.833
Eye Corrosion:	0.913
Eye Irritation:	0.995
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC7018

Natural Product ID:	NPC7018
*Common Name:**	6-Methyl-7,8-Dihydro-5H-[1,3]Dioxolo[4,5-G]Isoquinoline
IUPAC Name:	6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline
Synonyms:
Standard InCHIKey:	XNZFFRJWTVYMBF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H13NO2/c1-12-3-2-8-4-10-11(14-7-13-10)5-9(8)6-12/h4-5H,2-3,6-7H2,1H3
SMILES:	CN1CCc2c(C1)cc1c(c2)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2140445
PubChem CID:	22301
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002955] Tetrahydroisoquinolines

*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
NPO29263	Tylopilus plumbeoviolaceus	Species	Boletaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[10785434]
NPO28926	Corydalis tuberosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28926	Corydalis tuberosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28926	Corydalis tuberosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29347	Hydnum aurantiacum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17311	Penicillium vulpinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29441	Eremophila oppositifolia	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29490	Taxillus yadoriki	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29086	Dovyalis hebecarpa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29246	Ixeris repens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29263	Tylopilus plumbeoviolaceus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29206	Lycopodium chinense	Species	Lycopodiaceae	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
IC50	5
Ki	7
Others	7
Potency	1

Activity Type	# Activity
Individual Protein	3
Organism	7
Others	1
Protein Complex	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	1000.0	nM	PMID[482713]
NPT410	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Homo sapiens	IC50	>	100000.0	nM	PMID[482715]
NPT410	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Homo sapiens	EC50	>	100000.0	nM	PMID[482715]
NPT412	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Rattus norvegicus	Ki	=	1700.0	nM	PMID[482714]
NPT418	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta4	Rattus norvegicus	Ki	=	50000.0	nM	PMID[482714]
NPT417	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Rattus norvegicus	Ki	=	300000.0	nM	PMID[482714]
NPT2	Others	Unspecified		Ki	=	500000.0	nM	PMID[482714]
NPT964	Protein Complex	Nicotinic acetylcholine receptor alpha-4/beta-2	Mus musculus	IC50	=	2600.0	nM	PMID[482714]
NPT417	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Rattus norvegicus	IC50	=	300000.0	nM	PMID[482714]
NPT417	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Rattus norvegicus	Ki	=	300000.0	nM	PMID[482715]
NPT418	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta4	Rattus norvegicus	Ki	=	50000.0	nM	PMID[482715]
NPT412	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Rattus norvegicus	Ki	=	17000.0	nM	PMID[482715]
NPT964	Protein Complex	Nicotinic acetylcholine receptor alpha-4/beta-2	Mus musculus	IC50	=	2600.0	nM	PMID[482715]
NPT417	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Rattus norvegicus	IC50	=	300000.0	nM	PMID[482715]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	11.12	%	PMID[482716]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	=	3.04	%	PMID[482716]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	14.65	%	PMID[482716]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	1.35	%	PMID[482716]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	-14.77	%	PMID[482716]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	Inhibition	=	-5.07	%	PMID[482716]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	-8.47	%	PMID[482716]

☑ 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 NPC7018 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	259
0.1-0.2	1820
0.2-0.3	10024
0.3-0.4	8228
0.4-0.5	8988
0.5-0.6	9824
0.6-0.7	2668
0.7-0.8	660
0.8-0.85	178
0.85-0.9	39
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.938	High Similarity	NPC160193
0.9209	High Similarity	NPC59907
0.9209	High Similarity	NPC37144
0.9209	High Similarity	NPC475959
0.9104	High Similarity	NPC416184
0.9023	High Similarity	NPC160692
0.8963	High Similarity	NPC131204
0.8963	High Similarity	NPC301050
0.8951	High Similarity	NPC233029
0.8951	High Similarity	NPC148898
0.8951	High Similarity	NPC210148
0.8944	High Similarity	NPC223125
0.8828	High Similarity	NPC216459
0.8828	High Similarity	NPC41178
0.8828	High Similarity	NPC78733
0.8828	High Similarity	NPC93593
0.8828	High Similarity	NPC138487
0.8819	High Similarity	NPC223124
0.8768	High Similarity	NPC314682
0.8767	High Similarity	NPC146288
0.8759	High Similarity	NPC253429
0.8705	High Similarity	NPC474915
0.8705	High Similarity	NPC213206
0.8705	High Similarity	NPC328750
0.8705	High Similarity	NPC188163
0.8649	High Similarity	NPC106786
0.8649	High Similarity	NPC111485
0.8649	High Similarity	NPC477080
0.8647	High Similarity	NPC172403
0.8639	High Similarity	NPC31311
0.8639	High Similarity	NPC234392
0.8592	High Similarity	NPC130926
0.8591	High Similarity	NPC266753
0.8591	High Similarity	NPC160298
0.8591	High Similarity	NPC306902
0.8591	High Similarity	NPC232924
0.8591	High Similarity	NPC477559
0.8582	High Similarity	NPC136860
0.8582	High Similarity	NPC476567
0.8582	High Similarity	NPC128019
0.8533	High Similarity	NPC24954
0.8477	Intermediate Similarity	NPC59567
0.8467	Intermediate Similarity	NPC215829
0.8467	Intermediate Similarity	NPC97072
0.8462	Intermediate Similarity	NPC185838
0.8446	Intermediate Similarity	NPC76079
0.8421	Intermediate Similarity	NPC302527
0.8421	Intermediate Similarity	NPC276944
0.8421	Intermediate Similarity	NPC232514
0.8421	Intermediate Similarity	NPC225774
0.8421	Intermediate Similarity	NPC238530
0.8421	Intermediate Similarity	NPC16805
0.8421	Intermediate Similarity	NPC167546
0.8421	Intermediate Similarity	NPC231198
0.8421	Intermediate Similarity	NPC306669
0.8392	Intermediate Similarity	NPC294249
0.8366	Intermediate Similarity	NPC476432
0.8366	Intermediate Similarity	NPC24264
0.8366	Intermediate Similarity	NPC219341
0.8357	Intermediate Similarity	NPC252107
0.8356	Intermediate Similarity	NPC219162
0.8355	Intermediate Similarity	NPC320104
0.8345	Intermediate Similarity	NPC476151
0.8345	Intermediate Similarity	NPC321505
0.8345	Intermediate Similarity	NPC106295
0.8345	Intermediate Similarity	NPC210437
0.8345	Intermediate Similarity	NPC51957
0.8345	Intermediate Similarity	NPC179825
0.8345	Intermediate Similarity	NPC476144
0.8345	Intermediate Similarity	NPC191376
0.8345	Intermediate Similarity	NPC16107
0.8333	Intermediate Similarity	NPC145304
0.8312	Intermediate Similarity	NPC474324
0.8312	Intermediate Similarity	NPC57812
0.8312	Intermediate Similarity	NPC247389
0.8312	Intermediate Similarity	NPC210918
0.8312	Intermediate Similarity	NPC298979
0.8312	Intermediate Similarity	NPC100566
0.8301	Intermediate Similarity	NPC168409
0.8301	Intermediate Similarity	NPC247972
0.8299	Intermediate Similarity	NPC274026
0.8288	Intermediate Similarity	NPC147390
0.8288	Intermediate Similarity	NPC476571
0.8288	Intermediate Similarity	NPC135538
0.8288	Intermediate Similarity	NPC24233
0.8288	Intermediate Similarity	NPC246587
0.8288	Intermediate Similarity	NPC130941
0.8288	Intermediate Similarity	NPC7467
0.8288	Intermediate Similarity	NPC428
0.8286	Intermediate Similarity	NPC99078
0.8273	Intermediate Similarity	NPC167096
0.8258	Intermediate Similarity	NPC82533
0.8258	Intermediate Similarity	NPC290759
0.8258	Intermediate Similarity	NPC158148
0.8258	Intermediate Similarity	NPC241055
0.8258	Intermediate Similarity	NPC475845
0.8258	Intermediate Similarity	NPC266176
0.8247	Intermediate Similarity	NPC86144
0.8247	Intermediate Similarity	NPC304659
0.8235	Intermediate Similarity	NPC189470
0.8231	Intermediate Similarity	NPC103379
0.8231	Intermediate Similarity	NPC477565
0.8227	Intermediate Similarity	NPC220923
0.8227	Intermediate Similarity	NPC470707
0.8219	Intermediate Similarity	NPC95075
0.8219	Intermediate Similarity	NPC90844
0.8219	Intermediate Similarity	NPC253883
0.8214	Intermediate Similarity	NPC255817
0.8214	Intermediate Similarity	NPC277042
0.8214	Intermediate Similarity	NPC230698
0.8214	Intermediate Similarity	NPC205178
0.8214	Intermediate Similarity	NPC73883
0.8214	Intermediate Similarity	NPC251454
0.8214	Intermediate Similarity	NPC136330
0.8214	Intermediate Similarity	NPC196609
0.8209	Intermediate Similarity	NPC217277
0.8205	Intermediate Similarity	NPC474708
0.8205	Intermediate Similarity	NPC75958
0.8194	Intermediate Similarity	NPC181653
0.8194	Intermediate Similarity	NPC190332
0.8188	Intermediate Similarity	NPC133011
0.8188	Intermediate Similarity	NPC476570
0.8188	Intermediate Similarity	NPC82285
0.8176	Intermediate Similarity	NPC97221
0.8176	Intermediate Similarity	NPC151895
0.8176	Intermediate Similarity	NPC192768
0.8176	Intermediate Similarity	NPC88249
0.8176	Intermediate Similarity	NPC220858
0.8153	Intermediate Similarity	NPC19520
0.8153	Intermediate Similarity	NPC65403
0.8153	Intermediate Similarity	NPC470739
0.8153	Intermediate Similarity	NPC149090
0.8153	Intermediate Similarity	NPC477640
0.8153	Intermediate Similarity	NPC225597
0.8146	Intermediate Similarity	NPC147091
0.8141	Intermediate Similarity	NPC475686
0.8141	Intermediate Similarity	NPC58766
0.8129	Intermediate Similarity	NPC476002
0.8121	Intermediate Similarity	NPC476568
0.8121	Intermediate Similarity	NPC326316
0.8121	Intermediate Similarity	NPC476579
0.8121	Intermediate Similarity	NPC119669
0.8121	Intermediate Similarity	NPC81733
0.8108	Intermediate Similarity	NPC92541
0.8108	Intermediate Similarity	NPC207824
0.8108	Intermediate Similarity	NPC211296
0.8108	Intermediate Similarity	NPC60538
0.8101	Intermediate Similarity	NPC2314
0.8101	Intermediate Similarity	NPC4669
0.8099	Intermediate Similarity	NPC225745
0.8089	Intermediate Similarity	NPC311991
0.8089	Intermediate Similarity	NPC6152
0.8089	Intermediate Similarity	NPC474475
0.8085	Intermediate Similarity	NPC11147
0.8085	Intermediate Similarity	NPC180647
0.8067	Intermediate Similarity	NPC476580
0.805	Intermediate Similarity	NPC304675
0.805	Intermediate Similarity	NPC229166
0.805	Intermediate Similarity	NPC187678
0.805	Intermediate Similarity	NPC128560
0.805	Intermediate Similarity	NPC199465
0.8025	Intermediate Similarity	NPC86469
0.8	Intermediate Similarity	NPC298486
0.8	Intermediate Similarity	NPC287588
0.8	Intermediate Similarity	NPC118419
0.8	Intermediate Similarity	NPC76213
0.8	Intermediate Similarity	NPC237044
0.8	Intermediate Similarity	NPC474470
0.8	Intermediate Similarity	NPC277669
0.7987	Intermediate Similarity	NPC249274
0.7987	Intermediate Similarity	NPC470088
0.7987	Intermediate Similarity	NPC205167
0.7986	Intermediate Similarity	NPC77572
0.7975	Intermediate Similarity	NPC152212
0.7973	Intermediate Similarity	NPC144863
0.7961	Intermediate Similarity	NPC127674
0.7961	Intermediate Similarity	NPC172765
0.7961	Intermediate Similarity	NPC469817
0.7961	Intermediate Similarity	NPC278799
0.7961	Intermediate Similarity	NPC54379
0.7961	Intermediate Similarity	NPC80129
0.7961	Intermediate Similarity	NPC276588
0.7961	Intermediate Similarity	NPC207757
0.7961	Intermediate Similarity	NPC193949
0.7961	Intermediate Similarity	NPC99659
0.7961	Intermediate Similarity	NPC204828
0.7961	Intermediate Similarity	NPC295691
0.7961	Intermediate Similarity	NPC187022
0.7961	Intermediate Similarity	NPC244112
0.7961	Intermediate Similarity	NPC110416
0.7961	Intermediate Similarity	NPC325871
0.7961	Intermediate Similarity	NPC39701
0.7961	Intermediate Similarity	NPC249797
0.7961	Intermediate Similarity	NPC2413
0.7961	Intermediate Similarity	NPC189266
0.7961	Intermediate Similarity	NPC5238
0.7961	Intermediate Similarity	NPC184026
0.795	Intermediate Similarity	NPC474325
0.795	Intermediate Similarity	NPC118633
0.795	Intermediate Similarity	NPC294790

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 NPC7018 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	824
0.2-0.3	1115
0.3-0.4	2097
0.4-0.5	2697
0.5-0.6	1506
0.6-0.7	576
0.7-0.8	135
0.8-0.85	19
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8705	High Similarity	NPD4664	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD4584	Approved
0.8333	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD3641	Approved
0.8231	Intermediate Similarity	NPD3640	Phase 3
0.8231	Intermediate Similarity	NPD3639	Approved
0.8214	Intermediate Similarity	NPD2492	Phase 1
0.8188	Intermediate Similarity	NPD5718	Phase 2
0.8121	Intermediate Similarity	NPD4017	Approved
0.8108	Intermediate Similarity	NPD6031	Approved
0.8108	Intermediate Similarity	NPD6030	Approved
0.8043	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4773	Phase 2
0.8013	Intermediate Similarity	NPD4772	Phase 2
0.7961	Intermediate Similarity	NPD7298	Approved
0.7857	Intermediate Similarity	NPD2560	Approved
0.7857	Intermediate Similarity	NPD2563	Approved
0.7852	Intermediate Similarity	NPD1424	Approved
0.7847	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4166	Phase 2
0.7785	Intermediate Similarity	NPD6071	Discontinued
0.7778	Intermediate Similarity	NPD6895	Approved
0.7778	Intermediate Similarity	NPD6896	Approved
0.7722	Intermediate Similarity	NPD6107	Approved
0.7664	Intermediate Similarity	NPD3705	Approved
0.7658	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5241	Discontinued
0.7643	Intermediate Similarity	NPD5604	Discontinued
0.7643	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7833	Phase 2
0.7643	Intermediate Similarity	NPD7831	Phase 2
0.7628	Intermediate Similarity	NPD5978	Approved
0.7628	Intermediate Similarity	NPD5977	Approved
0.7622	Intermediate Similarity	NPD2674	Phase 3
0.761	Intermediate Similarity	NPD7802	Discontinued
0.7578	Intermediate Similarity	NPD2898	Approved
0.7562	Intermediate Similarity	NPD4010	Discontinued
0.755	Intermediate Similarity	NPD3124	Discontinued
0.7532	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6788	Approved
0.7452	Intermediate Similarity	NPD2978	Approved
0.7452	Intermediate Similarity	NPD2977	Approved
0.7452	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5312	Approved
0.7439	Intermediate Similarity	NPD5313	Approved
0.7436	Intermediate Similarity	NPD7110	Phase 1
0.7436	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD3145	Approved
0.7431	Intermediate Similarity	NPD3144	Approved
0.7429	Intermediate Similarity	NPD1420	Approved
0.7429	Intermediate Similarity	NPD1421	Approved
0.7425	Intermediate Similarity	NPD7280	Phase 3
0.7425	Intermediate Similarity	NPD7281	Phase 3
0.7417	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6688	Approved
0.7407	Intermediate Similarity	NPD6687	Approved
0.7403	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3885	Approved
0.7386	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1375	Discontinued
0.7378	Intermediate Similarity	NPD8252	Approved
0.7378	Intermediate Similarity	NPD8099	Discontinued
0.7378	Intermediate Similarity	NPD8251	Approved
0.7372	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7124	Phase 2
0.7362	Intermediate Similarity	NPD4481	Phase 3
0.7355	Intermediate Similarity	NPD4210	Discontinued
0.7349	Intermediate Similarity	NPD6297	Approved
0.7347	Intermediate Similarity	NPD2653	Approved
0.7346	Intermediate Similarity	NPD3051	Approved
0.7333	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8156	Discontinued
0.7329	Intermediate Similarity	NPD3109	Approved
0.7329	Intermediate Similarity	NPD3110	Approved
0.7314	Intermediate Similarity	NPD4420	Approved
0.7301	Intermediate Similarity	NPD2970	Approved
0.7301	Intermediate Similarity	NPD2969	Approved
0.7297	Intermediate Similarity	NPD6111	Discontinued
0.7285	Intermediate Similarity	NPD4237	Approved
0.7285	Intermediate Similarity	NPD3060	Approved
0.7285	Intermediate Similarity	NPD5177	Phase 3
0.7285	Intermediate Similarity	NPD4236	Phase 3
0.7285	Intermediate Similarity	NPD4162	Approved
0.7273	Intermediate Similarity	NPD7905	Discontinued
0.7267	Intermediate Similarity	NPD3656	Approved
0.7266	Intermediate Similarity	NPD2668	Approved
0.7266	Intermediate Similarity	NPD2667	Approved
0.7261	Intermediate Similarity	NPD6875	Approved
0.7261	Intermediate Similarity	NPD6876	Approved
0.726	Intermediate Similarity	NPD4474	Approved
0.726	Intermediate Similarity	NPD4475	Approved
0.7256	Intermediate Similarity	NPD27	Approved
0.7256	Intermediate Similarity	NPD2489	Approved
0.7255	Intermediate Similarity	NPD2120	Phase 2
0.7226	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5677	Discontinued
0.7219	Intermediate Similarity	NPD7153	Discontinued
0.7212	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2161	Phase 2
0.7197	Intermediate Similarity	NPD824	Approved
0.7194	Intermediate Similarity	NPD1357	Approved
0.7188	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1669	Approved
0.7179	Intermediate Similarity	NPD4727	Phase 1
0.7179	Intermediate Similarity	NPD5976	Discontinued
0.7176	Intermediate Similarity	NPD6851	Approved
0.7176	Intermediate Similarity	NPD6853	Approved
0.717	Intermediate Similarity	NPD5720	Discontinued
0.717	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3349	Phase 2
0.7151	Intermediate Similarity	NPD5006	Approved
0.7151	Intermediate Similarity	NPD5005	Approved
0.7133	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4108	Discontinued
0.7132	Intermediate Similarity	NPD5283	Phase 1
0.7124	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2232	Approved
0.7113	Intermediate Similarity	NPD2233	Approved
0.7113	Intermediate Similarity	NPD2230	Approved
0.7097	Intermediate Similarity	NPD5297	Approved
0.7083	Intermediate Similarity	NPD4098	Discontinued
0.7076	Intermediate Similarity	NPD8054	Approved
0.7076	Intermediate Similarity	NPD8053	Approved
0.7076	Intermediate Similarity	NPD6618	Phase 2
0.7075	Intermediate Similarity	NPD1336	Approved
0.7075	Intermediate Similarity	NPD1039	Discontinued
0.7071	Intermediate Similarity	NPD2595	Approved
0.7071	Intermediate Similarity	NPD2594	Approved
0.707	Intermediate Similarity	NPD1914	Approved
0.7063	Intermediate Similarity	NPD3384	Approved
0.7063	Intermediate Similarity	NPD3383	Approved
0.7063	Intermediate Similarity	NPD3382	Approved
0.7051	Intermediate Similarity	NPD4123	Phase 3
0.7035	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD709	Approved
0.7027	Intermediate Similarity	NPD3530	Approved
0.7027	Intermediate Similarity	NPD3532	Approved
0.7027	Intermediate Similarity	NPD3531	Approved
0.702	Intermediate Similarity	NPD1753	Discontinued
0.7019	Intermediate Similarity	NPD5772	Approved
0.7019	Intermediate Similarity	NPD5773	Approved
0.7013	Intermediate Similarity	NPD6331	Phase 2
0.7013	Intermediate Similarity	NPD5754	Discontinued
0.7011	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5582	Discontinued
0.6993	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2420	Approved
0.6987	Remote Similarity	NPD2421	Approved
0.6985	Remote Similarity	NPD228	Approved
0.698	Remote Similarity	NPD2238	Phase 2
0.6977	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3156	Discontinued
0.6968	Remote Similarity	NPD3692	Discontinued
0.6959	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD743	Approved
0.6946	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4739	Approved
0.6943	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7296	Approved
0.6923	Remote Similarity	NPD3845	Phase 1
0.6919	Remote Similarity	NPD2971	Approved
0.6919	Remote Similarity	NPD2968	Approved
0.6918	Remote Similarity	NPD7247	Discontinued
0.6908	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6748	Discontinued
0.6899	Remote Similarity	NPD6090	Discontinued
0.6894	Remote Similarity	NPD6873	Phase 2
0.6894	Remote Similarity	NPD6386	Approved
0.6894	Remote Similarity	NPD6385	Approved
0.689	Remote Similarity	NPD4055	Discovery
0.6887	Remote Similarity	NPD2986	Phase 2
0.6887	Remote Similarity	NPD2989	Phase 2
0.6882	Remote Similarity	NPD3920	Phase 2
0.6879	Remote Similarity	NPD2486	Discontinued
0.6875	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7291	Discontinued
0.6857	Remote Similarity	NPD7906	Approved
0.6854	Remote Similarity	NPD6493	Phase 3
0.6853	Remote Similarity	NPD3294	Phase 2
0.6851	Remote Similarity	NPD5457	Discontinued
0.6848	Remote Similarity	NPD7400	Phase 3
0.6846	Remote Similarity	NPD5109	Approved
0.6846	Remote Similarity	NPD5110	Phase 2
0.6846	Remote Similarity	NPD5111	Phase 2
0.6842	Remote Similarity	NPD7119	Phase 2
0.6842	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD593	Approved
0.6835	Remote Similarity	NPD595	Approved
0.6832	Remote Similarity	NPD4675	Approved
0.6832	Remote Similarity	NPD4678	Approved
0.6831	Remote Similarity	NPD3443	Approved
0.6831	Remote Similarity	NPD6382	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data