NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	223.14
Volume:	254.801
LogP:	3.353
LogD:	3.453
LogS:	-2.075
# Rotatable Bonds:	2
TPSA:	12.03
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.825
Synthetic Accessibility Score:	2.289
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.587
MDCK Permeability:	1.7832770026871003e-05
Pgp-inhibitor:	0.165
Pgp-substrate:	0.433
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.623

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.966
Plasma Protein Binding (PPB):	90.7981185913086%
Volume Distribution (VD):	1.533
Pgp-substrate:	10.818397521972656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.356
CYP1A2-substrate:	0.86
CYP2C19-inhibitor:	0.761
CYP2C19-substrate:	0.815
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.119
CYP2D6-inhibitor:	0.989
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.087
CYP3A4-substrate:	0.858

ADMET: Excretion

Clearance (CL):	7.3
Half-life (T1/2):	0.298

ADMET: Toxicity

hERG Blockers:	0.529
Human Hepatotoxicity (H-HT):	0.538
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.471
Rat Oral Acute Toxicity:	0.835
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.198
Carcinogencity:	0.082
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.766

Download Data

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

Natural Product: NPC329430

Natural Product ID:	NPC329430
*Common Name:**	1-Benzyl-1,2,3,4-Tetrahydroisoquinoline
IUPAC Name:	1-benzyl-1,2,3,4-tetrahydroisoquinoline
Synonyms:
Standard InCHIKey:	YRYCIFUZSUMAAY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H17N/c1-2-6-13(7-3-1)12-16-15-9-5-4-8-14(15)10-11-17-16/h1-9,16-17H,10-12H2
SMILES:	c1ccc(cc1)CC1NCCc2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL21640
PubChem CID:	98468
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

*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

☑ 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
ED50	2
IC50	3
Kd	1
Ki	3
Others	2

Activity Type	# Activity
Individual Protein	9
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6208	Individual Protein	Lysosomal Pro-X carboxypeptidase	Homo sapiens	IC50	=	1000.0	nM	PMID[483074]
NPT1067	Individual Protein	Sigma opioid receptor	Rattus norvegicus	IC50	=	430.0	nM	PMID[483074]
NPT4202	Individual Protein	Glutamate [NMDA] receptor subunit epsilon 3	Rattus norvegicus	ED50	=	26.0	mg.kg-1	PMID[483074]
NPT4202	Individual Protein	Glutamate [NMDA] receptor subunit epsilon 3	Rattus norvegicus	ED50	=	42.0	mg.kg-1	PMID[483074]
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	Ki	=	248800.0	nM	PMID[483075]
NPT1858	Individual Protein	Dopamine D2 receptor	Rattus norvegicus	Ki	=	3570.0	nM	PMID[483075]
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	Ki	=	36620.0	nM	PMID[483075]
NPT613	Individual Protein	Solute carrier family 22 member 1	Homo sapiens	IC50	=	82100.0	nM	PMID[483077]
NPT613	Individual Protein	Solute carrier family 22 member 1	Homo sapiens	Ratio	=	1.26	n.a.	PMID[483077]
NPT35	Others	n.a.		Kd	=	1.3	nM	PMID[483075]
NPT35	Others	n.a.		LogD7.4	n.a.	1.89	n.a.	PMID[483076]

☑ 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 NPC329430 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	682
0.1-0.2	5706
0.2-0.3	13735
0.3-0.4	15964
0.4-0.5	5040
0.5-0.6	1329
0.6-0.7	192
0.7-0.8	33
0.8-0.85	9
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9222	High Similarity	NPC470926
0.9091	High Similarity	NPC258046
0.8864	High Similarity	NPC169016
0.8384	Intermediate Similarity	NPC239854
0.8333	Intermediate Similarity	NPC104070
0.8333	Intermediate Similarity	NPC119677
0.8242	Intermediate Similarity	NPC133162
0.7978	Intermediate Similarity	NPC12857
0.7865	Intermediate Similarity	NPC325662
0.7865	Intermediate Similarity	NPC98269
0.7857	Intermediate Similarity	NPC322040
0.7788	Intermediate Similarity	NPC475915
0.7753	Intermediate Similarity	NPC139658
0.7556	Intermediate Similarity	NPC271642
0.7528	Intermediate Similarity	NPC122327
0.7528	Intermediate Similarity	NPC113000
0.7528	Intermediate Similarity	NPC112609
0.7522	Intermediate Similarity	NPC320656
0.75	Intermediate Similarity	NPC291610
0.7473	Intermediate Similarity	NPC290638
0.7453	Intermediate Similarity	NPC474695
0.7444	Intermediate Similarity	NPC98976
0.7426	Intermediate Similarity	NPC108339
0.7423	Intermediate Similarity	NPC60408
0.7386	Intermediate Similarity	NPC229235
0.7386	Intermediate Similarity	NPC219246
0.734	Intermediate Similarity	NPC231986
0.7327	Intermediate Similarity	NPC469330
0.7315	Intermediate Similarity	NPC434
0.7315	Intermediate Similarity	NPC79618
0.7253	Intermediate Similarity	NPC276699
0.7184	Intermediate Similarity	NPC471320
0.7184	Intermediate Similarity	NPC471319
0.71	Intermediate Similarity	NPC176858
0.7091	Intermediate Similarity	NPC302790
0.7059	Intermediate Similarity	NPC108800
0.7034	Intermediate Similarity	NPC314192
0.703	Intermediate Similarity	NPC191444
0.7025	Intermediate Similarity	NPC252794
0.6916	Remote Similarity	NPC474582
0.6818	Remote Similarity	NPC473418
0.6818	Remote Similarity	NPC167336
0.6774	Remote Similarity	NPC299134
0.6769	Remote Similarity	NPC170170
0.6769	Remote Similarity	NPC211468
0.6769	Remote Similarity	NPC219233
0.6752	Remote Similarity	NPC313673
0.6733	Remote Similarity	NPC305602
0.6733	Remote Similarity	NPC17497
0.6718	Remote Similarity	NPC323123
0.6667	Remote Similarity	NPC30445
0.6667	Remote Similarity	NPC126458
0.6667	Remote Similarity	NPC7067
0.6667	Remote Similarity	NPC244738
0.664	Remote Similarity	NPC40488
0.6639	Remote Similarity	NPC264580
0.6634	Remote Similarity	NPC203076
0.663	Remote Similarity	NPC72670
0.6629	Remote Similarity	NPC291066
0.6591	Remote Similarity	NPC22786
0.6591	Remote Similarity	NPC71009
0.6579	Remote Similarity	NPC24777
0.6579	Remote Similarity	NPC292758
0.6579	Remote Similarity	NPC65855
0.6569	Remote Similarity	NPC473031
0.656	Remote Similarity	NPC145754
0.6555	Remote Similarity	NPC313449
0.6535	Remote Similarity	NPC229477
0.6525	Remote Similarity	NPC101139
0.6522	Remote Similarity	NPC213570
0.6522	Remote Similarity	NPC246822
0.6522	Remote Similarity	NPC139416
0.6517	Remote Similarity	NPC113670
0.6491	Remote Similarity	NPC77294
0.6489	Remote Similarity	NPC54269
0.6481	Remote Similarity	NPC311242
0.6477	Remote Similarity	NPC246588
0.646	Remote Similarity	NPC473498
0.6452	Remote Similarity	NPC251490
0.6452	Remote Similarity	NPC263385
0.6452	Remote Similarity	NPC217277
0.6444	Remote Similarity	NPC155172
0.6442	Remote Similarity	NPC470877
0.6434	Remote Similarity	NPC149379
0.6429	Remote Similarity	NPC159661
0.6421	Remote Similarity	NPC96835
0.6421	Remote Similarity	NPC258492
0.6392	Remote Similarity	NPC249018
0.6392	Remote Similarity	NPC3190
0.6383	Remote Similarity	NPC87099
0.6383	Remote Similarity	NPC280135
0.6383	Remote Similarity	NPC226999
0.6383	Remote Similarity	NPC1008
0.6383	Remote Similarity	NPC135433
0.6383	Remote Similarity	NPC193578
0.6383	Remote Similarity	NPC39799
0.6383	Remote Similarity	NPC158028
0.6381	Remote Similarity	NPC74936
0.6381	Remote Similarity	NPC141139
0.6381	Remote Similarity	NPC78041
0.6381	Remote Similarity	NPC471307
0.6381	Remote Similarity	NPC159178
0.6381	Remote Similarity	NPC121872
0.6381	Remote Similarity	NPC209764
0.6377	Remote Similarity	NPC109787
0.6364	Remote Similarity	NPC315216
0.6356	Remote Similarity	NPC187036
0.6354	Remote Similarity	NPC307195
0.6346	Remote Similarity	NPC111233
0.6341	Remote Similarity	NPC273830
0.6337	Remote Similarity	NPC474088
0.6337	Remote Similarity	NPC134825
0.6327	Remote Similarity	NPC66270
0.6327	Remote Similarity	NPC255345
0.6327	Remote Similarity	NPC245896
0.632	Remote Similarity	NPC192533
0.6316	Remote Similarity	NPC1901
0.6304	Remote Similarity	NPC267443
0.6303	Remote Similarity	NPC246904
0.6292	Remote Similarity	NPC210849
0.6292	Remote Similarity	NPC238023
0.6292	Remote Similarity	NPC310758
0.629	Remote Similarity	NPC268534
0.6288	Remote Similarity	NPC478140
0.6286	Remote Similarity	NPC207824
0.6286	Remote Similarity	NPC60538
0.6283	Remote Similarity	NPC150254
0.6283	Remote Similarity	NPC304761
0.6283	Remote Similarity	NPC275467
0.6283	Remote Similarity	NPC226778
0.6283	Remote Similarity	NPC147000
0.6281	Remote Similarity	NPC192209
0.627	Remote Similarity	NPC79698
0.6262	Remote Similarity	NPC473661
0.626	Remote Similarity	NPC313352
0.626	Remote Similarity	NPC326232
0.625	Remote Similarity	NPC114327
0.625	Remote Similarity	NPC36357
0.6239	Remote Similarity	NPC319579
0.6232	Remote Similarity	NPC264589
0.6228	Remote Similarity	NPC67043
0.6222	Remote Similarity	NPC66517
0.622	Remote Similarity	NPC146373
0.622	Remote Similarity	NPC119326
0.622	Remote Similarity	NPC166424
0.622	Remote Similarity	NPC245244
0.621	Remote Similarity	NPC71684
0.6204	Remote Similarity	NPC471309
0.6204	Remote Similarity	NPC291070
0.6204	Remote Similarity	NPC246757
0.62	Remote Similarity	NPC50063
0.6197	Remote Similarity	NPC277669
0.6197	Remote Similarity	NPC76213
0.6183	Remote Similarity	NPC33338
0.6183	Remote Similarity	NPC300020
0.6183	Remote Similarity	NPC302171
0.6172	Remote Similarity	NPC478079
0.617	Remote Similarity	NPC200936
0.617	Remote Similarity	NPC33421
0.617	Remote Similarity	NPC473206
0.6154	Remote Similarity	NPC21211
0.614	Remote Similarity	NPC469974
0.6136	Remote Similarity	NPC474473
0.6129	Remote Similarity	NPC6107
0.6124	Remote Similarity	NPC8305
0.6124	Remote Similarity	NPC268763
0.6124	Remote Similarity	NPC328590
0.6124	Remote Similarity	NPC66177
0.6122	Remote Similarity	NPC110264
0.6119	Remote Similarity	NPC325252
0.6116	Remote Similarity	NPC473573
0.6116	Remote Similarity	NPC288232
0.6111	Remote Similarity	NPC135924
0.6111	Remote Similarity	NPC477564
0.6111	Remote Similarity	NPC2295
0.6107	Remote Similarity	NPC473962
0.6107	Remote Similarity	NPC282398
0.6106	Remote Similarity	NPC327226
0.6103	Remote Similarity	NPC314682
0.6103	Remote Similarity	NPC88097
0.6095	Remote Similarity	NPC262295
0.6094	Remote Similarity	NPC318965
0.6087	Remote Similarity	NPC32312
0.6087	Remote Similarity	NPC476198
0.6087	Remote Similarity	NPC311330
0.6087	Remote Similarity	NPC198023
0.6083	Remote Similarity	NPC296163
0.6077	Remote Similarity	NPC124802
0.6075	Remote Similarity	NPC172128
0.6075	Remote Similarity	NPC316108
0.6074	Remote Similarity	NPC253429
0.6071	Remote Similarity	NPC323726
0.6061	Remote Similarity	NPC101165
0.6058	Remote Similarity	NPC188163
0.6058	Remote Similarity	NPC470925
0.6058	Remote Similarity	NPC213206
0.6058	Remote Similarity	NPC474915
0.6058	Remote Similarity	NPC328750
0.6056	Remote Similarity	NPC206592
0.6048	Remote Similarity	NPC91958

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 NPC329430 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	873
0.2-0.3	1065
0.3-0.4	2596
0.4-0.5	2737
0.5-0.6	1169
0.6-0.7	269
0.7-0.8	100
0.8-0.85	29
0.85-0.9	8
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9667	High Similarity	NPD2005	Discontinued
0.9355	High Similarity	NPD1946	Clinical (unspecified phase)
0.9255	High Similarity	NPD1916	Discontinued
0.913	High Similarity	NPD5554	Approved
0.8776	High Similarity	NPD4936	Approved
0.8776	High Similarity	NPD4937	Approved
0.8696	High Similarity	NPD5915	Approved
0.8602	High Similarity	NPD2998	Approved
0.8602	High Similarity	NPD2997	Approved
0.8602	High Similarity	NPD3000	Approved
0.8571	High Similarity	NPD4146	Approved
0.8571	High Similarity	NPD4145	Approved
0.8444	Intermediate Similarity	NPD2539	Approved
0.8444	Intermediate Similarity	NPD2538	Approved
0.8421	Intermediate Similarity	NPD6548	Approved
0.8421	Intermediate Similarity	NPD6549	Approved
0.8404	Intermediate Similarity	NPD4543	Discontinued
0.837	Intermediate Similarity	NPD3426	Approved
0.837	Intermediate Similarity	NPD3428	Approved
0.8352	Intermediate Similarity	NPD9505	Clinical (unspecified phase)
0.8316	Intermediate Similarity	NPD4407	Approved
0.8316	Intermediate Similarity	NPD4408	Approved
0.8316	Intermediate Similarity	NPD4405	Approved
0.8261	Intermediate Similarity	NPD4406	Approved
0.8261	Intermediate Similarity	NPD4409	Approved
0.8242	Intermediate Similarity	NPD3429	Approved
0.8242	Intermediate Similarity	NPD3427	Approved
0.8229	Intermediate Similarity	NPD735	Approved
0.8229	Intermediate Similarity	NPD736	Approved
0.8191	Intermediate Similarity	NPD5656	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD4027	Approved
0.8111	Intermediate Similarity	NPD4026	Approved
0.8085	Intermediate Similarity	NPD3345	Approved
0.8081	Intermediate Similarity	NPD6499	Approved
0.8081	Intermediate Similarity	NPD6498	Approved
0.8065	Intermediate Similarity	NPD5252	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD4636	Approved
0.8041	Intermediate Similarity	NPD3980	Approved
0.8041	Intermediate Similarity	NPD4542	Approved
0.8041	Intermediate Similarity	NPD3982	Approved
0.8041	Intermediate Similarity	NPD2878	Approved
0.8041	Intermediate Similarity	NPD4545	Approved
0.8022	Intermediate Similarity	NPD4701	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD4170	Approved
0.8022	Intermediate Similarity	NPD4169	Approved
0.8019	Intermediate Similarity	NPD2038	Approved
0.8019	Intermediate Similarity	NPD2039	Approved
0.798	Intermediate Similarity	NPD5597	Approved
0.798	Intermediate Similarity	NPD5598	Approved
0.7979	Intermediate Similarity	NPD2002	Discontinued
0.7978	Intermediate Similarity	NPD296	Approved
0.7978	Intermediate Similarity	NPD293	Approved
0.7978	Intermediate Similarity	NPD295	Approved
0.7935	Intermediate Similarity	NPD831	Approved
0.7935	Intermediate Similarity	NPD830	Approved
0.7928	Intermediate Similarity	NPD5517	Phase 2
0.7928	Intermediate Similarity	NPD5516	Phase 2
0.7912	Intermediate Similarity	NPD3035	Approved
0.7889	Intermediate Similarity	NPD590	Approved
0.7889	Intermediate Similarity	NPD589	Approved
0.7857	Intermediate Similarity	NPD243	Approved
0.7857	Intermediate Similarity	NPD8	Approved
0.7849	Intermediate Similarity	NPD785	Approved
0.7849	Intermediate Similarity	NPD5178	Approved
0.7802	Intermediate Similarity	NPD5372	Approved
0.7802	Intermediate Similarity	NPD5371	Approved
0.7789	Intermediate Similarity	NPD783	Approved
0.7789	Intermediate Similarity	NPD781	Approved
0.7789	Intermediate Similarity	NPD782	Approved
0.7789	Intermediate Similarity	NPD780	Approved
0.7768	Intermediate Similarity	NPD1922	Discontinued
0.7767	Intermediate Similarity	NPD5103	Approved
0.7742	Intermediate Similarity	NPD4635	Approved
0.7732	Intermediate Similarity	NPD3344	Approved
0.7732	Intermediate Similarity	NPD3346	Approved
0.7714	Intermediate Similarity	NPD7170	Discontinued
0.7692	Intermediate Similarity	NPD2939	Approved
0.7692	Intermediate Similarity	NPD2937	Phase 1
0.7667	Intermediate Similarity	NPD4147	Approved
0.7667	Intermediate Similarity	NPD4144	Approved
0.7667	Intermediate Similarity	NPD603	Approved
0.7658	Intermediate Similarity	NPD5162	Approved
0.7653	Intermediate Similarity	NPD7160	Approved
0.7624	Intermediate Similarity	NPD713	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3979	Approved
0.7609	Intermediate Similarity	NPD3904	Approved
0.7609	Intermediate Similarity	NPD3903	Approved
0.7609	Intermediate Similarity	NPD3981	Approved
0.7582	Intermediate Similarity	NPD9564	Approved
0.7582	Intermediate Similarity	NPD9563	Approved
0.7582	Intermediate Similarity	NPD79	Approved
0.7579	Intermediate Similarity	NPD5916	Discontinued
0.757	Intermediate Similarity	NPD8010	Approved
0.757	Intermediate Similarity	NPD8009	Approved
0.7553	Intermediate Similarity	NPD2001	Discontinued
0.7545	Intermediate Similarity	NPD6562	Approved
0.7545	Intermediate Similarity	NPD6561	Approved
0.7545	Intermediate Similarity	NPD2913	Approved
0.7545	Intermediate Similarity	NPD2914	Approved
0.7528	Intermediate Similarity	NPD9593	Approved
0.7528	Intermediate Similarity	NPD9588	Approved
0.7528	Intermediate Similarity	NPD9594	Approved
0.7528	Intermediate Similarity	NPD80	Approved
0.7528	Intermediate Similarity	NPD9591	Approved
0.7528	Intermediate Similarity	NPD9590	Approved
0.7528	Intermediate Similarity	NPD9592	Approved
0.7528	Intermediate Similarity	NPD9589	Approved
0.7525	Intermediate Similarity	NPD5963	Phase 2
0.7525	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5964	Phase 2
0.7525	Intermediate Similarity	NPD1738	Approved
0.7524	Intermediate Similarity	NPD2980	Phase 2
0.7522	Intermediate Similarity	NPD2395	Approved
0.7522	Intermediate Similarity	NPD5511	Discontinued
0.7522	Intermediate Similarity	NPD2396	Approved
0.7477	Intermediate Similarity	NPD7062	Discontinued
0.7474	Intermediate Similarity	NPD4544	Approved
0.7419	Intermediate Similarity	NPD1617	Discontinued
0.7419	Intermediate Similarity	NPD260	Discontinued
0.7391	Intermediate Similarity	NPD4416	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5832	Phase 3
0.7364	Intermediate Similarity	NPD3001	Approved
0.7364	Intermediate Similarity	NPD2999	Approved
0.7347	Intermediate Similarity	NPD5675	Discontinued
0.7339	Intermediate Similarity	NPD7633	Discontinued
0.7339	Intermediate Similarity	NPD4116	Approved
0.7339	Intermediate Similarity	NPD6235	Approved
0.7339	Intermediate Similarity	NPD6236	Approved
0.7321	Intermediate Similarity	NPD5629	Discontinued
0.7315	Intermediate Similarity	NPD5253	Approved
0.7312	Intermediate Similarity	NPD1051	Approved
0.7312	Intermediate Similarity	NPD507	Approved
0.7312	Intermediate Similarity	NPD1053	Approved
0.7312	Intermediate Similarity	NPD1052	Approved
0.7312	Intermediate Similarity	NPD508	Approved
0.7292	Intermediate Similarity	NPD9395	Approved
0.7282	Intermediate Similarity	NPD528	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5130	Phase 3
0.7273	Intermediate Similarity	NPD771	Phase 3
0.7238	Intermediate Similarity	NPD5630	Phase 1
0.7232	Intermediate Similarity	NPD7060	Approved
0.7232	Intermediate Similarity	NPD7059	Approved
0.7196	Intermediate Similarity	NPD1026	Approved
0.7196	Intermediate Similarity	NPD1028	Approved
0.7193	Intermediate Similarity	NPD4660	Discontinued
0.7184	Intermediate Similarity	NPD6472	Discontinued
0.7184	Intermediate Similarity	NPD2895	Discontinued
0.717	Intermediate Similarity	NPD6024	Approved
0.717	Intermediate Similarity	NPD6027	Approved
0.7168	Intermediate Similarity	NPD3551	Approved
0.7168	Intermediate Similarity	NPD4674	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3099	Discontinued
0.713	Intermediate Similarity	NPD1269	Approved
0.713	Intermediate Similarity	NPD959	Discontinued
0.713	Intermediate Similarity	NPD1268	Approved
0.7111	Intermediate Similarity	NPD294	Approved
0.7111	Intermediate Similarity	NPD292	Approved
0.7105	Intermediate Similarity	NPD1720	Phase 2
0.7105	Intermediate Similarity	NPD1723	Phase 2
0.71	Intermediate Similarity	NPD9349	Approved
0.71	Intermediate Similarity	NPD9	Approved
0.71	Intermediate Similarity	NPD9348	Approved
0.71	Intermediate Similarity	NPD9350	Approved
0.71	Intermediate Similarity	NPD9351	Phase 3
0.71	Intermediate Similarity	NPD297	Approved
0.7094	Intermediate Similarity	NPD5961	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1935	Phase 3
0.7043	Intermediate Similarity	NPD7679	Phase 2
0.7041	Intermediate Similarity	NPD2205	Approved
0.7041	Intermediate Similarity	NPD2208	Approved
0.7034	Intermediate Similarity	NPD5576	Approved
0.7034	Intermediate Similarity	NPD5579	Approved
0.7025	Intermediate Similarity	NPD5838	Phase 2
0.7025	Intermediate Similarity	NPD3826	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5581	Approved
0.7009	Intermediate Similarity	NPD4734	Approved
0.7009	Intermediate Similarity	NPD2841	Approved
0.7009	Intermediate Similarity	NPD5716	Approved
0.7009	Intermediate Similarity	NPD4735	Approved
0.7	Intermediate Similarity	NPD2940	Approved
0.7	Intermediate Similarity	NPD2938	Approved
0.6981	Remote Similarity	NPD523	Approved
0.6981	Remote Similarity	NPD4007	Approved
0.6981	Remote Similarity	NPD524	Approved
0.6981	Remote Similarity	NPD4008	Approved
0.6975	Remote Similarity	NPD4323	Clinical (unspecified phase)
0.697	Remote Similarity	NPD304	Approved
0.697	Remote Similarity	NPD305	Approved
0.6957	Remote Similarity	NPD4032	Approved
0.6957	Remote Similarity	NPD4031	Approved
0.6957	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD2961	Approved
0.6942	Remote Similarity	NPD2962	Approved
0.6937	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5180	Approved
0.693	Remote Similarity	NPD5179	Approved
0.693	Remote Similarity	NPD5181	Approved
0.6923	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3546	Approved
0.6909	Remote Similarity	NPD3545	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