NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	193.11
Volume:	202.367
LogP:	0.778
LogD:	1.14
LogS:	-0.349
# Rotatable Bonds:	1
TPSA:	41.49
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.712
Synthetic Accessibility Score:	2.893
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:	-4.713
MDCK Permeability:	1.6869169485289603e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.915
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.061
30% Bioavailability (F30%):	0.13

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.533
Plasma Protein Binding (PPB):	21.882266998291016%
Volume Distribution (VD):	2.501
Pgp-substrate:	71.23419952392578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.686
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.735
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.217
CYP2D6-inhibitor:	0.28
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.51

ADMET: Excretion

Clearance (CL):	10.872
Half-life (T1/2):	0.756

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.837
Drug-inuced Liver Injury (DILI):	0.228
AMES Toxicity:	0.179
Rat Oral Acute Toxicity:	0.576
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.46
Carcinogencity:	0.066
Eye Corrosion:	0.021
Eye Irritation:	0.067
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC294249

Natural Product ID:	NPC294249
*Common Name:**	(1S)-7-Methoxy-1-Methyl-1,2,3,4-Tetrahydroisoquinolin-6-Ol
IUPAC Name:	(1S)-7-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol
Synonyms:	(-)-Salsoline
Standard InCHIKey:	YTPRLBGPGZHUPD-ZETCQYMHSA-N
Standard InCHI:	InChI=1S/C11H15NO2/c1-7-9-6-11(14-2)10(13)5-8(9)3-4-12-7/h5-7,12-13H,3-4H2,1-2H3/t7-/m0/s1
SMILES:	C[C@H]1c2cc(c(cc2CCN1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1187592
PubChem CID:	442356
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
NPO15309	Salsola collina	Species	Chenopodiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17511147]
NPO15309	Salsola collina	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15309	Salsola collina	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15309	Salsola collina	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15309	Salsola collina	Species	Chenopodiaceae	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
Others	2
Potency	3

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	12589.3	nM	PMID[535786]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	39810.7	nM	PMID[535786]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	19952.6	nM	PMID[535786]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	10.75	%	PMID[535787]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-4.77	%	PMID[535787]

☑ 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 NPC294249 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	242
0.1-0.2	1849
0.2-0.3	11393
0.3-0.4	6640
0.4-0.5	8178
0.5-0.6	10697
0.6-0.7	2816
0.7-0.8	632
0.8-0.85	149
0.85-0.9	69
0.9-0.95	29
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9507	High Similarity	NPC277669
0.9507	High Similarity	NPC76213
0.9412	High Similarity	NPC253429
0.9366	High Similarity	NPC60538
0.9366	High Similarity	NPC207824
0.9338	High Similarity	NPC301050
0.9338	High Similarity	NPC131204
0.9259	High Similarity	NPC160692
0.9241	High Similarity	NPC2295
0.9241	High Similarity	NPC477564
0.9185	High Similarity	NPC302171
0.9185	High Similarity	NPC300020
0.9185	High Similarity	NPC33338
0.9091	High Similarity	NPC191376
0.9091	High Similarity	NPC321505
0.9091	High Similarity	NPC179825
0.9028	High Similarity	NPC147390
0.9028	High Similarity	NPC246587
0.9028	High Similarity	NPC428
0.9028	High Similarity	NPC476571
0.9028	High Similarity	NPC24233
0.9028	High Similarity	NPC135538
0.8951	High Similarity	NPC185838
0.8904	High Similarity	NPC97221
0.8904	High Similarity	NPC220858
0.8904	High Similarity	NPC192768
0.8904	High Similarity	NPC88249
0.8904	High Similarity	NPC151895
0.8882	High Similarity	NPC284183
0.8882	High Similarity	NPC121275
0.8882	High Similarity	NPC4138
0.8836	High Similarity	NPC103379
0.8836	High Similarity	NPC477565
0.8824	High Similarity	NPC81247
0.8824	High Similarity	NPC476573
0.8824	High Similarity	NPC35627
0.8759	High Similarity	NPC160193
0.8699	High Similarity	NPC476151
0.8667	High Similarity	NPC5238
0.8667	High Similarity	NPC2413
0.8667	High Similarity	NPC469817
0.8667	High Similarity	NPC39701
0.8667	High Similarity	NPC276588
0.8667	High Similarity	NPC295691
0.8667	High Similarity	NPC189266
0.8667	High Similarity	NPC193949
0.8667	High Similarity	NPC184026
0.8667	High Similarity	NPC110416
0.8667	High Similarity	NPC207757
0.8667	High Similarity	NPC278799
0.8667	High Similarity	NPC249797
0.8667	High Similarity	NPC172765
0.8667	High Similarity	NPC54379
0.8667	High Similarity	NPC127674
0.8667	High Similarity	NPC204828
0.8662	High Similarity	NPC211468
0.8662	High Similarity	NPC170170
0.8662	High Similarity	NPC219233
0.8658	High Similarity	NPC82285
0.8658	High Similarity	NPC133011
0.8654	High Similarity	NPC26240
0.8654	High Similarity	NPC69712
0.8654	High Similarity	NPC477562
0.8654	High Similarity	NPC109925
0.8609	High Similarity	NPC147091
0.8601	High Similarity	NPC314682
0.8601	High Similarity	NPC323123
0.8599	High Similarity	NPC108434
0.8599	High Similarity	NPC475215
0.8544	High Similarity	NPC477020
0.8544	High Similarity	NPC66341
0.8544	High Similarity	NPC192135
0.8542	High Similarity	NPC188163
0.8542	High Similarity	NPC328750
0.8542	High Similarity	NPC474915
0.8542	High Similarity	NPC213206
0.8533	High Similarity	NPC37272
0.8497	Intermediate Similarity	NPC111485
0.8487	Intermediate Similarity	NPC37205
0.8487	Intermediate Similarity	NPC160931
0.8456	Intermediate Similarity	NPC13020
0.8456	Intermediate Similarity	NPC140359
0.8456	Intermediate Similarity	NPC217277
0.8442	Intermediate Similarity	NPC249274
0.8442	Intermediate Similarity	NPC166014
0.8442	Intermediate Similarity	NPC27410
0.8442	Intermediate Similarity	NPC205167
0.8425	Intermediate Similarity	NPC128019
0.8425	Intermediate Similarity	NPC476567
0.8425	Intermediate Similarity	NPC136860
0.8421	Intermediate Similarity	NPC187022
0.8421	Intermediate Similarity	NPC80129
0.84	Intermediate Similarity	NPC274026
0.8392	Intermediate Similarity	NPC7018
0.8366	Intermediate Similarity	NPC126519
0.8366	Intermediate Similarity	NPC170503
0.8366	Intermediate Similarity	NPC203784
0.8333	Intermediate Similarity	NPC324144
0.8333	Intermediate Similarity	NPC474507
0.8323	Intermediate Similarity	NPC173416
0.8323	Intermediate Similarity	NPC148709
0.8323	Intermediate Similarity	NPC476577
0.8302	Intermediate Similarity	NPC152212
0.8282	Intermediate Similarity	NPC476574
0.8282	Intermediate Similarity	NPC155442
0.8282	Intermediate Similarity	NPC477561
0.8282	Intermediate Similarity	NPC312918
0.828	Intermediate Similarity	NPC477563
0.828	Intermediate Similarity	NPC306843
0.828	Intermediate Similarity	NPC196447
0.828	Intermediate Similarity	NPC232514
0.828	Intermediate Similarity	NPC253043
0.828	Intermediate Similarity	NPC24465
0.828	Intermediate Similarity	NPC238530
0.828	Intermediate Similarity	NPC78222
0.828	Intermediate Similarity	NPC212794
0.828	Intermediate Similarity	NPC96603
0.828	Intermediate Similarity	NPC13504
0.828	Intermediate Similarity	NPC136508
0.828	Intermediate Similarity	NPC276944
0.8248	Intermediate Similarity	NPC298486
0.8247	Intermediate Similarity	NPC186063
0.8228	Intermediate Similarity	NPC268503
0.8228	Intermediate Similarity	NPC317272
0.8228	Intermediate Similarity	NPC13916
0.8228	Intermediate Similarity	NPC256012
0.8228	Intermediate Similarity	NPC42549
0.8228	Intermediate Similarity	NPC264850
0.8228	Intermediate Similarity	NPC250846
0.8228	Intermediate Similarity	NPC240841
0.8201	Intermediate Similarity	NPC318965
0.82	Intermediate Similarity	NPC106295
0.82	Intermediate Similarity	NPC210437
0.82	Intermediate Similarity	NPC16107
0.82	Intermediate Similarity	NPC476144
0.82	Intermediate Similarity	NPC51957
0.8194	Intermediate Similarity	NPC475326
0.8188	Intermediate Similarity	NPC130926
0.8182	Intermediate Similarity	NPC135772
0.8176	Intermediate Similarity	NPC12053
0.8176	Intermediate Similarity	NPC117188
0.8176	Intermediate Similarity	NPC205421
0.8176	Intermediate Similarity	NPC306555
0.8176	Intermediate Similarity	NPC145832
0.8176	Intermediate Similarity	NPC81218
0.8176	Intermediate Similarity	NPC158376
0.8176	Intermediate Similarity	NPC474931
0.8148	Intermediate Similarity	NPC477558
0.8146	Intermediate Similarity	NPC7467
0.8146	Intermediate Similarity	NPC475959
0.8125	Intermediate Similarity	NPC66573
0.8125	Intermediate Similarity	NPC83198
0.8125	Intermediate Similarity	NPC204908
0.8125	Intermediate Similarity	NPC470324
0.8112	Intermediate Similarity	NPC93882
0.8112	Intermediate Similarity	NPC130595
0.8101	Intermediate Similarity	NPC475393
0.8101	Intermediate Similarity	NPC1229
0.8089	Intermediate Similarity	NPC135006
0.8085	Intermediate Similarity	NPC172403
0.8077	Intermediate Similarity	NPC79328
0.8063	Intermediate Similarity	NPC210140
0.8056	Intermediate Similarity	NPC6854
0.8056	Intermediate Similarity	NPC313737
0.8056	Intermediate Similarity	NPC285078
0.8052	Intermediate Similarity	NPC26601
0.805	Intermediate Similarity	NPC2770
0.805	Intermediate Similarity	NPC39103
0.8042	Intermediate Similarity	NPC329595
0.8042	Intermediate Similarity	NPC326599
0.8038	Intermediate Similarity	NPC60186
0.8037	Intermediate Similarity	NPC329969
0.8036	Intermediate Similarity	NPC476576
0.8036	Intermediate Similarity	NPC186546
0.8025	Intermediate Similarity	NPC239775
0.8025	Intermediate Similarity	NPC476331
0.8025	Intermediate Similarity	NPC59028
0.8025	Intermediate Similarity	NPC92191
0.8015	Intermediate Similarity	NPC85276
0.8	Intermediate Similarity	NPC86144
0.8	Intermediate Similarity	NPC218530
0.8	Intermediate Similarity	NPC304659
0.7988	Intermediate Similarity	NPC48490
0.7988	Intermediate Similarity	NPC274661
0.7988	Intermediate Similarity	NPC11296
0.7988	Intermediate Similarity	NPC82457
0.7988	Intermediate Similarity	NPC175890
0.7987	Intermediate Similarity	NPC293871
0.7987	Intermediate Similarity	NPC326316
0.7987	Intermediate Similarity	NPC124433
0.7987	Intermediate Similarity	NPC476568
0.7987	Intermediate Similarity	NPC81733
0.7987	Intermediate Similarity	NPC189470
0.7975	Intermediate Similarity	NPC215829
0.7975	Intermediate Similarity	NPC226428
0.7975	Intermediate Similarity	NPC152680
0.7975	Intermediate Similarity	NPC232386
0.7975	Intermediate Similarity	NPC190783
0.7975	Intermediate Similarity	NPC97072
0.7963	Intermediate Similarity	NPC118274

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 NPC294249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	702
0.2-0.3	1189
0.3-0.4	1903
0.4-0.5	2761
0.5-0.6	1602
0.6-0.7	620
0.7-0.8	189
0.8-0.85	22
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8542	High Similarity	NPD4664	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD6031	Approved
0.8456	Intermediate Similarity	NPD6030	Approved
0.8421	Intermediate Similarity	NPD7298	Approved
0.8311	Intermediate Similarity	NPD3845	Phase 1
0.8276	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD4773	Phase 2
0.8235	Intermediate Similarity	NPD4772	Phase 2
0.8228	Intermediate Similarity	NPD4010	Discontinued
0.82	Intermediate Similarity	NPD4584	Approved
0.8188	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD2898	Approved
0.8112	Intermediate Similarity	NPD2674	Phase 3
0.8112	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD3060	Approved
0.8099	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD3640	Phase 3
0.8092	Intermediate Similarity	NPD3639	Approved
0.8092	Intermediate Similarity	NPD3641	Approved
0.8079	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD3053	Approved
0.8071	Intermediate Similarity	NPD3055	Approved
0.8013	Intermediate Similarity	NPD2977	Approved
0.8013	Intermediate Similarity	NPD2978	Approved
0.8	Intermediate Similarity	NPD5241	Discontinued
0.7988	Intermediate Similarity	NPD6297	Approved
0.7987	Intermediate Similarity	NPD4017	Approved
0.7961	Intermediate Similarity	NPD1424	Approved
0.7945	Intermediate Similarity	NPD817	Approved
0.7945	Intermediate Similarity	NPD823	Approved
0.7937	Intermediate Similarity	NPD6107	Approved
0.7917	Intermediate Similarity	NPD3144	Approved
0.7917	Intermediate Similarity	NPD3145	Approved
0.7888	Intermediate Similarity	NPD4166	Phase 2
0.7875	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD4162	Approved
0.7862	Intermediate Similarity	NPD1136	Approved
0.7862	Intermediate Similarity	NPD1130	Approved
0.7862	Intermediate Similarity	NPD1132	Approved
0.7798	Intermediate Similarity	NPD6851	Approved
0.7798	Intermediate Similarity	NPD6853	Approved
0.7793	Intermediate Similarity	NPD601	Approved
0.7793	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD598	Approved
0.7793	Intermediate Similarity	NPD597	Approved
0.7746	Intermediate Similarity	NPD5310	Approved
0.7746	Intermediate Similarity	NPD5311	Approved
0.7692	Intermediate Similarity	NPD8053	Approved
0.7692	Intermediate Similarity	NPD8054	Approved
0.7683	Intermediate Similarity	NPD27	Approved
0.7683	Intermediate Similarity	NPD2489	Approved
0.7682	Intermediate Similarity	NPD7153	Discontinued
0.7677	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD5718	Phase 2
0.7662	Intermediate Similarity	NPD2420	Approved
0.7662	Intermediate Similarity	NPD2421	Approved
0.764	Intermediate Similarity	NPD7833	Phase 2
0.764	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7831	Phase 2
0.7639	Intermediate Similarity	NPD9620	Approved
0.7639	Intermediate Similarity	NPD9621	Approved
0.7639	Intermediate Similarity	NPD9619	Approved
0.7625	Intermediate Similarity	NPD2560	Approved
0.7625	Intermediate Similarity	NPD2563	Approved
0.7622	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD9377	Approved
0.7574	Intermediate Similarity	NPD9379	Approved
0.7561	Intermediate Similarity	NPD6071	Discontinued
0.7552	Intermediate Similarity	NPD9622	Approved
0.7534	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD824	Approved
0.7515	Intermediate Similarity	NPD2970	Approved
0.7515	Intermediate Similarity	NPD4083	Discontinued
0.7515	Intermediate Similarity	NPD2969	Approved
0.75	Intermediate Similarity	NPD228	Approved
0.7483	Intermediate Similarity	NPD1753	Discontinued
0.7467	Intermediate Similarity	NPD2653	Approved
0.7455	Intermediate Similarity	NPD3051	Approved
0.745	Intermediate Similarity	NPD3059	Approved
0.745	Intermediate Similarity	NPD3062	Approved
0.745	Intermediate Similarity	NPD3061	Approved
0.7436	Intermediate Similarity	NPD3124	Discontinued
0.7419	Intermediate Similarity	NPD5160	Discontinued
0.7403	Intermediate Similarity	NPD2458	Approved
0.7403	Intermediate Similarity	NPD2459	Approved
0.7403	Intermediate Similarity	NPD2460	Phase 3
0.7386	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2120	Phase 2
0.7368	Intermediate Similarity	NPD2156	Approved
0.7368	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2154	Approved
0.7368	Intermediate Similarity	NPD2155	Approved
0.7358	Intermediate Similarity	NPD3687	Approved
0.7358	Intermediate Similarity	NPD3686	Approved
0.7355	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3052	Approved
0.7351	Intermediate Similarity	NPD2989	Phase 2
0.7351	Intermediate Similarity	NPD3054	Approved
0.7351	Intermediate Similarity	NPD5314	Approved
0.7351	Intermediate Similarity	NPD2986	Phase 2
0.7346	Intermediate Similarity	NPD4585	Approved
0.7338	Intermediate Similarity	NPD593	Approved
0.7338	Intermediate Similarity	NPD595	Approved
0.7338	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1817	Approved
0.7329	Intermediate Similarity	NPD1819	Approved
0.7329	Intermediate Similarity	NPD1818	Approved
0.7329	Intermediate Similarity	NPD1820	Approved
0.7321	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3156	Discontinued
0.7308	Intermediate Similarity	NPD3692	Discontinued
0.7308	Intermediate Similarity	NPD2677	Approved
0.7303	Intermediate Similarity	NPD6895	Approved
0.7303	Intermediate Similarity	NPD6896	Approved
0.7297	Intermediate Similarity	NPD596	Approved
0.7297	Intermediate Similarity	NPD600	Approved
0.729	Intermediate Similarity	NPD5177	Phase 3
0.7284	Intermediate Similarity	NPD5720	Discontinued
0.7278	Intermediate Similarity	NPD8251	Approved
0.7278	Intermediate Similarity	NPD8252	Approved
0.7278	Intermediate Similarity	NPD2874	Phase 2
0.7278	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8099	Discontinued
0.7278	Intermediate Similarity	NPD3645	Discontinued
0.7273	Intermediate Similarity	NPD9384	Approved
0.7273	Intermediate Similarity	NPD9381	Approved
0.7267	Intermediate Similarity	NPD259	Phase 1
0.7267	Intermediate Similarity	NPD3531	Approved
0.7267	Intermediate Similarity	NPD3530	Approved
0.7267	Intermediate Similarity	NPD3532	Approved
0.7257	Intermediate Similarity	NPD7906	Approved
0.7256	Intermediate Similarity	NPD6788	Approved
0.7254	Intermediate Similarity	NPD316	Approved
0.7241	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD8156	Discontinued
0.7235	Intermediate Similarity	NPD5312	Approved
0.7235	Intermediate Similarity	NPD5313	Approved
0.7233	Intermediate Similarity	NPD52	Approved
0.7233	Intermediate Similarity	NPD7526	Approved
0.7233	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4666	Phase 3
0.7225	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7313	Approved
0.7225	Intermediate Similarity	NPD4578	Approved
0.7225	Intermediate Similarity	NPD4577	Approved
0.7225	Intermediate Similarity	NPD7312	Approved
0.7225	Intermediate Similarity	NPD7311	Approved
0.7225	Intermediate Similarity	NPD7310	Approved
0.7222	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1774	Approved
0.72	Intermediate Similarity	NPD1039	Discontinued
0.72	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1336	Approved
0.7193	Intermediate Similarity	NPD7479	Phase 2
0.7188	Intermediate Similarity	NPD5976	Discontinued
0.7186	Intermediate Similarity	NPD7802	Discontinued
0.7184	Intermediate Similarity	NPD7309	Approved
0.7184	Intermediate Similarity	NPD6618	Phase 2
0.7183	Intermediate Similarity	NPD9615	Approved
0.7183	Intermediate Similarity	NPD9613	Approved
0.7183	Intermediate Similarity	NPD9616	Approved
0.7179	Intermediate Similarity	NPD4236	Phase 3
0.7179	Intermediate Similarity	NPD4237	Approved
0.7171	Intermediate Similarity	NPD555	Phase 2
0.717	Intermediate Similarity	NPD3536	Discontinued
0.7169	Intermediate Similarity	NPD5709	Phase 3
0.7168	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2667	Approved
0.7153	Intermediate Similarity	NPD2668	Approved
0.7152	Intermediate Similarity	NPD1423	Approved
0.7135	Intermediate Similarity	NPD4873	Discontinued
0.7134	Intermediate Similarity	NPD5772	Approved
0.7134	Intermediate Similarity	NPD5773	Approved
0.7133	Intermediate Similarity	NPD3166	Approved
0.7133	Intermediate Similarity	NPD3164	Approved
0.7133	Intermediate Similarity	NPD3165	Approved
0.7133	Intermediate Similarity	NPD3167	Approved
0.7125	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2233	Approved
0.7123	Intermediate Similarity	NPD2232	Approved
0.7123	Intermediate Similarity	NPD2230	Approved
0.7115	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD9569	Approved
0.7108	Intermediate Similarity	NPD4055	Discovery
0.7107	Intermediate Similarity	NPD7598	Phase 2
0.7105	Intermediate Similarity	NPD3109	Approved
0.7105	Intermediate Similarity	NPD3110	Approved
0.7102	Intermediate Similarity	NPD4663	Approved
0.7099	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4005	Discontinued
0.7097	Intermediate Similarity	NPD2161	Phase 2
0.7095	Intermediate Similarity	NPD1794	Approved
0.7092	Intermediate Similarity	NPD9614	Approved
0.7092	Intermediate Similarity	NPD9618	Approved
0.7091	Intermediate Similarity	NPD5977	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