NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	193.11
Volume:	202.367
LogP:	1.167
LogD:	1.368
LogS:	-0.414
# Rotatable Bonds:	1
TPSA:	32.7
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.731
Synthetic Accessibility Score:	2.109
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.487
MDCK Permeability:	1.6036976376199163e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.135
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.291
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.997
Plasma Protein Binding (PPB):	29.22205924987793%
Volume Distribution (VD):	2.014
Pgp-substrate:	62.829036712646484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.235
CYP1A2-substrate:	0.922
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.915
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.48
CYP2D6-inhibitor:	0.749
CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.481

ADMET: Excretion

Clearance (CL):	15.966
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.25
Drug-inuced Liver Injury (DILI):	0.737
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.561
Maximum Recommended Daily Dose:	0.613
Skin Sensitization:	0.887
Carcinogencity:	0.148
Eye Corrosion:	0.147
Eye Irritation:	0.073
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC301050

Natural Product ID:	NPC301050
*Common Name:**	7-Methoxy-2-Methyl-3,4-Dihydro-1H-Isoquinolin-6-Ol
IUPAC Name:	7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-6-ol
Synonyms:
Standard InCHIKey:	VKAPHOQGGQKBAI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H15NO2/c1-12-4-3-8-5-10(13)11(14-2)6-9(8)7-12/h5-6,13H,3-4,7H2,1-2H3
SMILES:	COc1cc2CN(C)CCc2cc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3235514
PubChem CID:	2752173
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
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088436]
NPO25510	Plectranthus ernstii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19445517]
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22472691]
NPO28026	Grifola frondosa	Species	Schizophyllaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO859	Berberis oblonga	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8077	Artocarpus incisa	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO859	Berberis oblonga	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO435	Bohadschia marmorata	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28026	Grifola frondosa	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO859	Berberis oblonga	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1114	Cetraria australiensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10518	Chrysanthemum myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO595	Tephrosia falciformis	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8077	Artocarpus incisa	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25510	Plectranthus ernstii	Species	Lamiaceae	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	4

Activity Type	# Activity
Others	1
Protein Complex	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT412	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Rattus norvegicus	Ki	=	10000.0	nM	PMID[548498]
NPT418	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta4	Rattus norvegicus	Ki	=	100000.0	nM	PMID[548498]
NPT417	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Rattus norvegicus	Ki	=	300000.0	nM	PMID[548498]
NPT2	Others	Unspecified		Ki	>	500000.0	nM	PMID[548498]
NPT964	Protein Complex	Nicotinic acetylcholine receptor alpha-4/beta-2	Mus musculus	IC50	=	33000.0	nM	PMID[548498]
NPT417	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Rattus norvegicus	IC50	=	1000000.0	nM	PMID[548498]

☑ 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 NPC301050 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	230
0.1-0.2	1704
0.2-0.3	9640
0.3-0.4	8669
0.4-0.5	6503
0.5-0.6	10950
0.6-0.7	3734
0.7-0.8	1008
0.8-0.85	157
0.85-0.9	80
0.9-0.95	20
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC131204
0.938	High Similarity	NPC160193
0.9338	High Similarity	NPC294249
0.9275	High Similarity	NPC321505
0.9275	High Similarity	NPC179825
0.9275	High Similarity	NPC191376
0.9209	High Similarity	NPC24233
0.9209	High Similarity	NPC476571
0.9209	High Similarity	NPC246587
0.9209	High Similarity	NPC147390
0.9209	High Similarity	NPC135538
0.9209	High Similarity	NPC428
0.9143	High Similarity	NPC477565
0.9143	High Similarity	NPC103379
0.913	High Similarity	NPC185838
0.9078	High Similarity	NPC220858
0.9078	High Similarity	NPC97221
0.9078	High Similarity	NPC192768
0.9078	High Similarity	NPC88249
0.9078	High Similarity	NPC151895
0.9023	High Similarity	NPC160692
0.9	High Similarity	NPC476151
0.8963	High Similarity	NPC7018
0.8951	High Similarity	NPC133011
0.8951	High Similarity	NPC82285
0.8881	High Similarity	NPC76213
0.8881	High Similarity	NPC277669
0.8828	High Similarity	NPC276588
0.8828	High Similarity	NPC54379
0.8828	High Similarity	NPC249797
0.8828	High Similarity	NPC127674
0.8828	High Similarity	NPC207757
0.8828	High Similarity	NPC184026
0.8828	High Similarity	NPC5238
0.8828	High Similarity	NPC469817
0.8828	High Similarity	NPC204828
0.8828	High Similarity	NPC172765
0.8828	High Similarity	NPC189266
0.8828	High Similarity	NPC295691
0.8828	High Similarity	NPC193949
0.8828	High Similarity	NPC2413
0.8828	High Similarity	NPC278799
0.8828	High Similarity	NPC110416
0.8828	High Similarity	NPC39701
0.8768	High Similarity	NPC314682
0.8767	High Similarity	NPC147091
0.8759	High Similarity	NPC477564
0.8759	High Similarity	NPC2295
0.8759	High Similarity	NPC253429
0.8741	High Similarity	NPC207824
0.8741	High Similarity	NPC60538
0.8705	High Similarity	NPC474915
0.8705	High Similarity	NPC213206
0.8705	High Similarity	NPC328750
0.8705	High Similarity	NPC188163
0.869	High Similarity	NPC37272
0.8681	High Similarity	NPC274026
0.8649	High Similarity	NPC111485
0.8647	High Similarity	NPC172403
0.8591	High Similarity	NPC166014
0.8591	High Similarity	NPC135006
0.8591	High Similarity	NPC249274
0.8591	High Similarity	NPC205167
0.8591	High Similarity	NPC27410
0.8582	High Similarity	NPC136860
0.8582	High Similarity	NPC476567
0.8582	High Similarity	NPC128019
0.8533	High Similarity	NPC60186
0.8529	High Similarity	NPC130595
0.8529	High Similarity	NPC93882
0.8529	High Similarity	NPC33338
0.8529	High Similarity	NPC302171
0.8529	High Similarity	NPC300020
0.8514	High Similarity	NPC186063
0.8477	Intermediate Similarity	NPC324144
0.8467	Intermediate Similarity	NPC285078
0.8467	Intermediate Similarity	NPC313737
0.8467	Intermediate Similarity	NPC6854
0.8462	Intermediate Similarity	NPC130926
0.8456	Intermediate Similarity	NPC475326
0.8429	Intermediate Similarity	NPC231572
0.8421	Intermediate Similarity	NPC276944
0.8421	Intermediate Similarity	NPC253043
0.8421	Intermediate Similarity	NPC136508
0.8421	Intermediate Similarity	NPC24465
0.8421	Intermediate Similarity	NPC306843
0.8421	Intermediate Similarity	NPC232514
0.8421	Intermediate Similarity	NPC196447
0.8421	Intermediate Similarity	NPC4138
0.8421	Intermediate Similarity	NPC121275
0.8421	Intermediate Similarity	NPC284183
0.8421	Intermediate Similarity	NPC96603
0.8421	Intermediate Similarity	NPC78222
0.8421	Intermediate Similarity	NPC212794
0.8421	Intermediate Similarity	NPC477563
0.8421	Intermediate Similarity	NPC238530
0.8421	Intermediate Similarity	NPC13504
0.8406	Intermediate Similarity	NPC218530
0.8366	Intermediate Similarity	NPC13916
0.8366	Intermediate Similarity	NPC317272
0.8366	Intermediate Similarity	NPC42549
0.8366	Intermediate Similarity	NPC256012
0.8366	Intermediate Similarity	NPC264850
0.8366	Intermediate Similarity	NPC250846
0.8366	Intermediate Similarity	NPC268503
0.8366	Intermediate Similarity	NPC240841
0.8346	Intermediate Similarity	NPC140359
0.8346	Intermediate Similarity	NPC13020
0.8345	Intermediate Similarity	NPC210437
0.8345	Intermediate Similarity	NPC476144
0.8345	Intermediate Similarity	NPC51957
0.8345	Intermediate Similarity	NPC106295
0.8345	Intermediate Similarity	NPC16107
0.8344	Intermediate Similarity	NPC18402
0.8321	Intermediate Similarity	NPC308885
0.8321	Intermediate Similarity	NPC255550
0.8312	Intermediate Similarity	NPC306555
0.8312	Intermediate Similarity	NPC145832
0.8312	Intermediate Similarity	NPC205421
0.8312	Intermediate Similarity	NPC474931
0.8312	Intermediate Similarity	NPC81218
0.8312	Intermediate Similarity	NPC158376
0.8312	Intermediate Similarity	NPC12053
0.8312	Intermediate Similarity	NPC210140
0.8312	Intermediate Similarity	NPC117188
0.8311	Intermediate Similarity	NPC26601
0.8288	Intermediate Similarity	NPC475959
0.8288	Intermediate Similarity	NPC59907
0.8288	Intermediate Similarity	NPC7467
0.8288	Intermediate Similarity	NPC37144
0.8278	Intermediate Similarity	NPC92191
0.8278	Intermediate Similarity	NPC59028
0.8258	Intermediate Similarity	NPC83198
0.8258	Intermediate Similarity	NPC204908
0.8258	Intermediate Similarity	NPC66573
0.8258	Intermediate Similarity	NPC470324
0.8247	Intermediate Similarity	NPC476573
0.8247	Intermediate Similarity	NPC35627
0.8247	Intermediate Similarity	NPC81247
0.8235	Intermediate Similarity	NPC1229
0.8235	Intermediate Similarity	NPC153990
0.8209	Intermediate Similarity	NPC217277
0.8205	Intermediate Similarity	NPC109925
0.8188	Intermediate Similarity	NPC223124
0.8188	Intermediate Similarity	NPC476570
0.8182	Intermediate Similarity	NPC134858
0.8156	Intermediate Similarity	NPC416184
0.8153	Intermediate Similarity	NPC476331
0.8153	Intermediate Similarity	NPC239775
0.8129	Intermediate Similarity	NPC214869
0.8121	Intermediate Similarity	NPC476579
0.8121	Intermediate Similarity	NPC81733
0.8121	Intermediate Similarity	NPC326316
0.8121	Intermediate Similarity	NPC119669
0.8121	Intermediate Similarity	NPC476568
0.8117	Intermediate Similarity	NPC233650
0.8108	Intermediate Similarity	NPC92541
0.8108	Intermediate Similarity	NPC219162
0.8105	Intermediate Similarity	NPC215829
0.8105	Intermediate Similarity	NPC97072
0.8105	Intermediate Similarity	NPC226428
0.8101	Intermediate Similarity	NPC190783
0.8101	Intermediate Similarity	NPC232386
0.8101	Intermediate Similarity	NPC152680
0.8099	Intermediate Similarity	NPC193528
0.8092	Intermediate Similarity	NPC40389
0.8092	Intermediate Similarity	NPC315707
0.8092	Intermediate Similarity	NPC148014
0.8092	Intermediate Similarity	NPC78359
0.8092	Intermediate Similarity	NPC65490
0.8089	Intermediate Similarity	NPC26240
0.8089	Intermediate Similarity	NPC69712
0.8089	Intermediate Similarity	NPC118274
0.8089	Intermediate Similarity	NPC168753
0.8089	Intermediate Similarity	NPC477562
0.8077	Intermediate Similarity	NPC100566
0.8077	Intermediate Similarity	NPC298979
0.8067	Intermediate Similarity	NPC476580
0.8067	Intermediate Similarity	NPC233029
0.8067	Intermediate Similarity	NPC148898
0.8067	Intermediate Similarity	NPC210148
0.8058	Intermediate Similarity	NPC114102
0.8054	Intermediate Similarity	NPC223125
0.805	Intermediate Similarity	NPC128560
0.805	Intermediate Similarity	NPC199465
0.805	Intermediate Similarity	NPC229166
0.8043	Intermediate Similarity	NPC155838
0.8042	Intermediate Similarity	NPC170170
0.8042	Intermediate Similarity	NPC211468
0.8042	Intermediate Similarity	NPC219233
0.8041	Intermediate Similarity	NPC130941
0.8038	Intermediate Similarity	NPC475215
0.8038	Intermediate Similarity	NPC108434
0.8013	Intermediate Similarity	NPC124657
0.8	Intermediate Similarity	NPC298486
0.7987	Intermediate Similarity	NPC66341
0.7987	Intermediate Similarity	NPC192135
0.7987	Intermediate Similarity	NPC477020
0.7986	Intermediate Similarity	NPC323123
0.7986	Intermediate Similarity	NPC195749

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 NPC301050 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	775
0.2-0.3	1175
0.3-0.4	1928
0.4-0.5	2652
0.5-0.6	1594
0.6-0.7	663
0.7-0.8	173
0.8-0.85	23
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)
0.8529	High Similarity	NPD2674	Phase 3
0.8378	Intermediate Similarity	NPD4772	Phase 2
0.8378	Intermediate Similarity	NPD4773	Phase 2
0.8366	Intermediate Similarity	NPD4010	Discontinued
0.8345	Intermediate Similarity	NPD4584	Approved
0.8321	Intermediate Similarity	NPD3145	Approved
0.8321	Intermediate Similarity	NPD3144	Approved
0.8258	Intermediate Similarity	NPD2898	Approved
0.8248	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD3639	Approved
0.8231	Intermediate Similarity	NPD3640	Phase 3
0.8231	Intermediate Similarity	NPD3641	Approved
0.8219	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD5718	Phase 2
0.8138	Intermediate Similarity	NPD5241	Discontinued
0.8121	Intermediate Similarity	NPD4017	Approved
0.8108	Intermediate Similarity	NPD6031	Approved
0.8108	Intermediate Similarity	NPD6030	Approved
0.8105	Intermediate Similarity	NPD7833	Phase 2
0.8105	Intermediate Similarity	NPD7831	Phase 2
0.8105	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD2560	Approved
0.8092	Intermediate Similarity	NPD2563	Approved
0.8043	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6071	Discontinued
0.8	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD824	Approved
0.7961	Intermediate Similarity	NPD7298	Approved
0.7908	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD228	Approved
0.7877	Intermediate Similarity	NPD3060	Approved
0.7852	Intermediate Similarity	NPD1424	Approved
0.7847	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD8053	Approved
0.7805	Intermediate Similarity	NPD8054	Approved
0.7799	Intermediate Similarity	NPD2489	Approved
0.7799	Intermediate Similarity	NPD27	Approved
0.7785	Intermediate Similarity	NPD2421	Approved
0.7785	Intermediate Similarity	NPD2420	Approved
0.7778	Intermediate Similarity	NPD6895	Approved
0.7778	Intermediate Similarity	NPD6896	Approved
0.7755	Intermediate Similarity	NPD5177	Phase 3
0.7718	Intermediate Similarity	NPD3845	Phase 1
0.7647	Intermediate Similarity	NPD2668	Approved
0.7647	Intermediate Similarity	NPD2667	Approved
0.7635	Intermediate Similarity	NPD4162	Approved
0.7625	Intermediate Similarity	NPD2969	Approved
0.7625	Intermediate Similarity	NPD2970	Approved
0.761	Intermediate Similarity	NPD6107	Approved
0.761	Intermediate Similarity	NPD7802	Discontinued
0.7609	Intermediate Similarity	NPD2230	Approved
0.7609	Intermediate Similarity	NPD2233	Approved
0.7609	Intermediate Similarity	NPD2232	Approved
0.7603	Intermediate Similarity	NPD1753	Discontinued
0.76	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3053	Approved
0.7571	Intermediate Similarity	NPD3055	Approved
0.7568	Intermediate Similarity	NPD7153	Discontinued
0.7562	Intermediate Similarity	NPD3051	Approved
0.7562	Intermediate Similarity	NPD4166	Phase 2
0.7561	Intermediate Similarity	NPD6297	Approved
0.7552	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3124	Discontinued
0.7533	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5977	Approved
0.7516	Intermediate Similarity	NPD5978	Approved
0.75	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5310	Approved
0.75	Intermediate Similarity	NPD3656	Approved
0.75	Intermediate Similarity	NPD5311	Approved
0.75	Intermediate Similarity	NPD4123	Phase 3
0.7483	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6788	Approved
0.7452	Intermediate Similarity	NPD2978	Approved
0.7452	Intermediate Similarity	NPD2977	Approved
0.7451	Intermediate Similarity	NPD6090	Discontinued
0.7448	Intermediate Similarity	NPD2238	Phase 2
0.7444	Intermediate Similarity	NPD9379	Approved
0.7444	Intermediate Similarity	NPD9377	Approved
0.7436	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7110	Phase 1
0.7432	Intermediate Similarity	NPD2161	Phase 2
0.7429	Intermediate Similarity	NPD1669	Approved
0.7423	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3692	Discontinued
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)
0.74	Intermediate Similarity	NPD4237	Approved
0.74	Intermediate Similarity	NPD4236	Phase 3
0.7394	Intermediate Similarity	NPD9621	Approved
0.7394	Intermediate Similarity	NPD9620	Approved
0.7394	Intermediate Similarity	NPD9619	Approved
0.7381	Intermediate Similarity	NPD6851	Approved
0.7381	Intermediate Similarity	NPD6853	Approved
0.7378	Intermediate Similarity	NPD8099	Discontinued
0.7378	Intermediate Similarity	NPD8251	Approved
0.7378	Intermediate Similarity	NPD8252	Approved
0.7376	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7124	Phase 2
0.7353	Intermediate Similarity	NPD7906	Approved
0.7347	Intermediate Similarity	NPD823	Approved
0.7347	Intermediate Similarity	NPD2492	Phase 1
0.7347	Intermediate Similarity	NPD817	Approved
0.7333	Intermediate Similarity	NPD5312	Approved
0.7333	Intermediate Similarity	NPD8156	Discontinued
0.7333	Intermediate Similarity	NPD5313	Approved
0.7329	Intermediate Similarity	NPD3109	Approved
0.7329	Intermediate Similarity	NPD3110	Approved
0.7321	Intermediate Similarity	NPD4577	Approved
0.7321	Intermediate Similarity	NPD7310	Approved
0.7321	Intermediate Similarity	NPD7312	Approved
0.7321	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4578	Approved
0.7321	Intermediate Similarity	NPD7313	Approved
0.7321	Intermediate Similarity	NPD7311	Approved
0.7319	Intermediate Similarity	NPD4093	Discontinued
0.7312	Intermediate Similarity	NPD5604	Discontinued
0.731	Intermediate Similarity	NPD1039	Discontinued
0.731	Intermediate Similarity	NPD597	Approved
0.731	Intermediate Similarity	NPD601	Approved
0.731	Intermediate Similarity	NPD598	Approved
0.7305	Intermediate Similarity	NPD1421	Approved
0.7305	Intermediate Similarity	NPD1420	Approved
0.7297	Intermediate Similarity	NPD6111	Discontinued
0.7278	Intermediate Similarity	NPD7309	Approved
0.7273	Intermediate Similarity	NPD7905	Discontinued
0.7267	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6876	Approved
0.7261	Intermediate Similarity	NPD6875	Approved
0.7261	Intermediate Similarity	NPD4675	Approved
0.7261	Intermediate Similarity	NPD4678	Approved
0.726	Intermediate Similarity	NPD1130	Approved
0.726	Intermediate Similarity	NPD1132	Approved
0.726	Intermediate Similarity	NPD4475	Approved
0.726	Intermediate Similarity	NPD1136	Approved
0.726	Intermediate Similarity	NPD4474	Approved
0.725	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6331	Phase 2
0.7233	Intermediate Similarity	NPD5773	Approved
0.7233	Intermediate Similarity	NPD5772	Approved
0.723	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2653	Approved
0.7222	Intermediate Similarity	NPD3635	Approved
0.7222	Intermediate Similarity	NPD3636	Approved
0.7222	Intermediate Similarity	NPD3637	Approved
0.7218	Intermediate Similarity	NPD1792	Phase 2
0.7211	Intermediate Similarity	NPD3062	Approved
0.7211	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3059	Approved
0.7211	Intermediate Similarity	NPD3620	Phase 2
0.7211	Intermediate Similarity	NPD3061	Approved
0.7206	Intermediate Similarity	NPD1793	Approved
0.7206	Intermediate Similarity	NPD1791	Approved
0.72	Intermediate Similarity	NPD3156	Discontinued
0.7195	Intermediate Similarity	NPD4083	Discontinued
0.7193	Intermediate Similarity	NPD4663	Approved
0.7179	Intermediate Similarity	NPD2122	Discontinued
0.7179	Intermediate Similarity	NPD1914	Approved
0.717	Intermediate Similarity	NPD5720	Discontinued
0.7168	Intermediate Similarity	NPD2488	Approved
0.7168	Intermediate Similarity	NPD2490	Approved
0.7153	Intermediate Similarity	NPD6584	Phase 3
0.7152	Intermediate Similarity	NPD1375	Discontinued
0.7143	Intermediate Similarity	NPD9381	Approved
0.7143	Intermediate Similarity	NPD1751	Approved
0.7143	Intermediate Similarity	NPD9384	Approved
0.7134	Intermediate Similarity	NPD3686	Approved
0.7134	Intermediate Similarity	NPD3687	Approved
0.7133	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3693	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2229	Approved
0.7132	Intermediate Similarity	NPD2228	Approved
0.7132	Intermediate Similarity	NPD2234	Approved
0.7132	Intermediate Similarity	NPD5283	Phase 1
0.7124	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1444	Approved
0.7121	Intermediate Similarity	NPD1445	Approved
0.7118	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5677	Discontinued
0.7115	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5314	Approved
0.7113	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7037	Approved
0.7099	Intermediate Similarity	NPD4055	Discovery
0.7095	Intermediate Similarity	NPD1558	Phase 1
0.7089	Intermediate Similarity	NPD4005	Discontinued
0.7083	Intermediate Similarity	NPD4098	Discontinued
0.7076	Intermediate Similarity	NPD6618	Phase 2
0.7071	Intermediate Similarity	NPD2595	Approved
0.7071	Intermediate Similarity	NPD2594	Approved
0.7063	Intermediate Similarity	NPD9622	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