NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	207.13
Volume:	219.663
LogP:	1.655
LogD:	1.579
LogS:	-1.807
# Rotatable Bonds:	2
TPSA:	21.7
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	1.894
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.44
MDCK Permeability:	1.8225571693619713e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.876
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.234
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.997
Plasma Protein Binding (PPB):	38.55070114135742%
Volume Distribution (VD):	2.117
Pgp-substrate:	50.77836608886719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.44
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.953
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.641
CYP2D6-inhibitor:	0.85
CYP2D6-substrate:	0.934
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.782

ADMET: Excretion

Clearance (CL):	10.826
Half-life (T1/2):	0.802

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.446
Drug-inuced Liver Injury (DILI):	0.873
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.675
Maximum Recommended Daily Dose:	0.45
Skin Sensitization:	0.713
Carcinogencity:	0.129
Eye Corrosion:	0.193
Eye Irritation:	0.042
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC160193

Natural Product ID:	NPC160193
*Common Name:**	6,7-Dimethoxy-2-Methyl-3,4-Dihydro-1H-Isoquinoline
IUPAC Name:	6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
Synonyms:
Standard InCHIKey:	TXPPKWZEHFNZOE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H17NO2/c1-13-5-4-9-6-11(14-2)12(15-3)7-10(9)8-13/h6-7H,4-5,8H2,1-3H3
SMILES:	CN1CCc2cc(c(cc2C1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1196025
PubChem CID:	27694
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
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1652	Arichanna gaschkevitchii	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16366	Citrus cavaleriei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4880	Artemisia ifranensis	Species	Asteraceae	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	12
Others	3

Activity Type	# Activity
Individual Protein	7
Others	4
Protein Complex	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT295	Individual Protein	Serotonin transporter	Homo sapiens	Ki	=	46700.0	nM	PMID[534783]
NPT246	Individual Protein	Dopamine transporter	Homo sapiens	Ki	>	10000000.0	nM	PMID[534783]
NPT228	Individual Protein	Norepinephrine transporter	Homo sapiens	Ki	=	128900.0	nM	PMID[534783]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	Ki	=	27000.0	nM	PMID[534783]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Ki	=	29000.0	nM	PMID[534783]
NPT410	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Homo sapiens	IC50	>	100000.0	nM	PMID[534784]
NPT410	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Homo sapiens	EC50	>	100000.0	nM	PMID[534784]
NPT412	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Rattus norvegicus	Ki	=	870.0	nM	PMID[534783]
NPT418	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta4	Rattus norvegicus	Ki	=	300000.0	nM	PMID[534783]
NPT417	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Rattus norvegicus	Ki	=	300000.0	nM	PMID[534783]
NPT2	Others	Unspecified		Ki	>	500000.0	nM	PMID[534783]
NPT964	Protein Complex	Nicotinic acetylcholine receptor alpha-4/beta-2	Mus musculus	IC50	=	12000.0	nM	PMID[534783]
NPT417	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Rattus norvegicus	IC50	=	100000.0	nM	PMID[534783]
NPT2	Others	Unspecified		Ratio Ki	>	300.0	n.a.	PMID[534783]
NPT417	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Rattus norvegicus	Ki	=	300000.0	nM	PMID[534784]
NPT418	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta4	Rattus norvegicus	Ki	=	300000.0	nM	PMID[534784]
NPT412	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Rattus norvegicus	Ki	=	870.0	nM	PMID[534784]
NPT964	Protein Complex	Nicotinic acetylcholine receptor alpha-4/beta-2	Mus musculus	IC50	=	12000.0	nM	PMID[534784]
NPT417	Protein Complex	Neuronal acetylcholine receptor; alpha3/beta4	Rattus norvegicus	IC50	=	100000.0	nM	PMID[534784]

☑ 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 NPC160193 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	274
0.1-0.2	2157
0.2-0.3	11753
0.3-0.4	6097
0.4-0.5	8606
0.5-0.6	10129
0.6-0.7	2776
0.7-0.8	690
0.8-0.85	158
0.85-0.9	42
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9449	High Similarity	NPC160692
0.938	High Similarity	NPC301050
0.938	High Similarity	NPC131204
0.938	High Similarity	NPC7018
0.9313	High Similarity	NPC314682
0.9308	High Similarity	NPC253429
0.9242	High Similarity	NPC328750
0.9242	High Similarity	NPC474915
0.9242	High Similarity	NPC188163
0.9242	High Similarity	NPC213206
0.9206	High Similarity	NPC172403
0.9104	High Similarity	NPC128019
0.9104	High Similarity	NPC476567
0.9104	High Similarity	NPC136860
0.8971	High Similarity	NPC185838
0.8971	High Similarity	NPC130926
0.8841	High Similarity	NPC106295
0.8841	High Similarity	NPC476151
0.8841	High Similarity	NPC51957
0.8841	High Similarity	NPC191376
0.8841	High Similarity	NPC210437
0.8841	High Similarity	NPC16107
0.8841	High Similarity	NPC321505
0.8841	High Similarity	NPC476144
0.8841	High Similarity	NPC179825
0.8777	High Similarity	NPC475959
0.8777	High Similarity	NPC24233
0.8777	High Similarity	NPC476571
0.8777	High Similarity	NPC7467
0.8777	High Similarity	NPC246587
0.8777	High Similarity	NPC135538
0.8777	High Similarity	NPC428
0.8777	High Similarity	NPC147390
0.8759	High Similarity	NPC294249
0.8714	High Similarity	NPC477565
0.8714	High Similarity	NPC103379
0.8652	High Similarity	NPC151895
0.8652	High Similarity	NPC88249
0.8652	High Similarity	NPC274026
0.8652	High Similarity	NPC192768
0.8652	High Similarity	NPC97221
0.8652	High Similarity	NPC220858
0.8643	High Similarity	NPC59907
0.8643	High Similarity	NPC37144
0.8594	High Similarity	NPC217277
0.8592	High Similarity	NPC326316
0.8592	High Similarity	NPC476568
0.8592	High Similarity	NPC81733
0.8592	High Similarity	NPC476579
0.8582	High Similarity	NPC219162
0.8582	High Similarity	NPC207824
0.8582	High Similarity	NPC92541
0.8582	High Similarity	NPC60538
0.8561	High Similarity	NPC476570
0.8531	High Similarity	NPC148898
0.8531	High Similarity	NPC82285
0.8531	High Similarity	NPC133011
0.8531	High Similarity	NPC210148
0.8531	High Similarity	NPC476580
0.8531	High Similarity	NPC233029
0.8519	High Similarity	NPC416184
0.8516	High Similarity	NPC298486
0.8511	High Similarity	NPC130941
0.8462	Intermediate Similarity	NPC119669
0.8462	Intermediate Similarity	NPC76213
0.8462	Intermediate Similarity	NPC277669
0.844	Intermediate Similarity	NPC90844
0.844	Intermediate Similarity	NPC253883
0.844	Intermediate Similarity	NPC95075
0.844	Intermediate Similarity	NPC144863
0.8414	Intermediate Similarity	NPC249797
0.8414	Intermediate Similarity	NPC295691
0.8414	Intermediate Similarity	NPC5238
0.8414	Intermediate Similarity	NPC127674
0.8414	Intermediate Similarity	NPC469817
0.8414	Intermediate Similarity	NPC325871
0.8414	Intermediate Similarity	NPC80129
0.8414	Intermediate Similarity	NPC54379
0.8414	Intermediate Similarity	NPC276588
0.8414	Intermediate Similarity	NPC99659
0.8414	Intermediate Similarity	NPC2413
0.8414	Intermediate Similarity	NPC138487
0.8414	Intermediate Similarity	NPC187022
0.8414	Intermediate Similarity	NPC278799
0.8414	Intermediate Similarity	NPC204828
0.8414	Intermediate Similarity	NPC93593
0.8414	Intermediate Similarity	NPC216459
0.8414	Intermediate Similarity	NPC78733
0.8414	Intermediate Similarity	NPC207757
0.8414	Intermediate Similarity	NPC184026
0.8414	Intermediate Similarity	NPC193949
0.8414	Intermediate Similarity	NPC39701
0.8414	Intermediate Similarity	NPC110416
0.8414	Intermediate Similarity	NPC172765
0.8414	Intermediate Similarity	NPC189266
0.8414	Intermediate Similarity	NPC41178
0.8392	Intermediate Similarity	NPC223125
0.8356	Intermediate Similarity	NPC247639
0.8356	Intermediate Similarity	NPC146288
0.8356	Intermediate Similarity	NPC147091
0.8356	Intermediate Similarity	NPC25084
0.8356	Intermediate Similarity	NPC57512
0.8345	Intermediate Similarity	NPC2295
0.8345	Intermediate Similarity	NPC477564
0.8309	Intermediate Similarity	NPC11147
0.8299	Intermediate Similarity	NPC476572
0.8298	Intermediate Similarity	NPC110337
0.8276	Intermediate Similarity	NPC470924
0.8276	Intermediate Similarity	NPC223124
0.8276	Intermediate Similarity	NPC37272
0.8248	Intermediate Similarity	NPC231884
0.8248	Intermediate Similarity	NPC42793
0.8248	Intermediate Similarity	NPC167944
0.8243	Intermediate Similarity	NPC118804
0.8243	Intermediate Similarity	NPC59028
0.8243	Intermediate Similarity	NPC216816
0.8243	Intermediate Similarity	NPC477080
0.8243	Intermediate Similarity	NPC92191
0.8243	Intermediate Similarity	NPC111485
0.8231	Intermediate Similarity	NPC234392
0.8231	Intermediate Similarity	NPC126519
0.8231	Intermediate Similarity	NPC31311
0.8231	Intermediate Similarity	NPC170503
0.8231	Intermediate Similarity	NPC203784
0.8222	Intermediate Similarity	NPC118419
0.8189	Intermediate Similarity	NPC120075
0.8188	Intermediate Similarity	NPC477559
0.8188	Intermediate Similarity	NPC166014
0.8188	Intermediate Similarity	NPC160298
0.8188	Intermediate Similarity	NPC232924
0.8188	Intermediate Similarity	NPC266753
0.8188	Intermediate Similarity	NPC205167
0.8188	Intermediate Similarity	NPC249274
0.8188	Intermediate Similarity	NPC27410
0.8188	Intermediate Similarity	NPC306902
0.8163	Intermediate Similarity	NPC244112
0.8151	Intermediate Similarity	NPC26601
0.8143	Intermediate Similarity	NPC470925
0.8133	Intermediate Similarity	NPC60186
0.8121	Intermediate Similarity	NPC106786
0.8108	Intermediate Similarity	NPC186063
0.8088	Intermediate Similarity	NPC130595
0.8088	Intermediate Similarity	NPC93882
0.8082	Intermediate Similarity	NPC85747
0.8082	Intermediate Similarity	NPC8337
0.8079	Intermediate Similarity	NPC59567
0.8079	Intermediate Similarity	NPC324144
0.8079	Intermediate Similarity	NPC233650
0.8079	Intermediate Similarity	NPC476569
0.8079	Intermediate Similarity	NPC475393
0.8074	Intermediate Similarity	NPC262641
0.8067	Intermediate Similarity	NPC135006
0.8067	Intermediate Similarity	NPC97072
0.8067	Intermediate Similarity	NPC215829
0.8054	Intermediate Similarity	NPC475326
0.8054	Intermediate Similarity	NPC315707
0.8054	Intermediate Similarity	NPC65490
0.8054	Intermediate Similarity	NPC40389
0.8054	Intermediate Similarity	NPC148014
0.8054	Intermediate Similarity	NPC78359
0.8054	Intermediate Similarity	NPC129603
0.8041	Intermediate Similarity	NPC76079
0.8029	Intermediate Similarity	NPC6854
0.8029	Intermediate Similarity	NPC285078
0.8029	Intermediate Similarity	NPC313737
0.8026	Intermediate Similarity	NPC96603
0.8026	Intermediate Similarity	NPC167546
0.8026	Intermediate Similarity	NPC78222
0.8026	Intermediate Similarity	NPC232514
0.8026	Intermediate Similarity	NPC276944
0.8026	Intermediate Similarity	NPC196447
0.8026	Intermediate Similarity	NPC231198
0.8026	Intermediate Similarity	NPC306843
0.8026	Intermediate Similarity	NPC212794
0.8026	Intermediate Similarity	NPC477563
0.8026	Intermediate Similarity	NPC4138
0.8026	Intermediate Similarity	NPC238530
0.8026	Intermediate Similarity	NPC302527
0.8026	Intermediate Similarity	NPC121275
0.8026	Intermediate Similarity	NPC13504
0.8026	Intermediate Similarity	NPC225774
0.8026	Intermediate Similarity	NPC136508
0.8026	Intermediate Similarity	NPC24465
0.8026	Intermediate Similarity	NPC16805
0.8026	Intermediate Similarity	NPC284183
0.8026	Intermediate Similarity	NPC134858
0.8026	Intermediate Similarity	NPC253043
0.8013	Intermediate Similarity	NPC24954
0.8	Intermediate Similarity	NPC210086
0.8	Intermediate Similarity	NPC231572
0.7987	Intermediate Similarity	NPC180756
0.7987	Intermediate Similarity	NPC323443
0.7985	Intermediate Similarity	NPC301713
0.7974	Intermediate Similarity	NPC13916
0.7974	Intermediate Similarity	NPC240841
0.7974	Intermediate Similarity	NPC219341
0.7974	Intermediate Similarity	NPC317272
0.7974	Intermediate Similarity	NPC268503
0.7974	Intermediate Similarity	NPC256012
0.7974	Intermediate Similarity	NPC476432

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 NPC160193 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	874
0.2-0.3	1069
0.3-0.4	1948
0.4-0.5	2713
0.5-0.6	1527
0.6-0.7	633
0.7-0.8	170
0.8-0.85	22
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9242	High Similarity	NPD4664	Clinical (unspecified phase)
0.8841	High Similarity	NPD4584	Approved
0.8769	High Similarity	NPD2669	Clinical (unspecified phase)
0.8714	High Similarity	NPD3641	Approved
0.8714	High Similarity	NPD3639	Approved
0.8714	High Similarity	NPD3640	Phase 3
0.8702	High Similarity	NPD5718	Phase 2
0.8592	High Similarity	NPD4017	Approved
0.8582	High Similarity	NPD6030	Approved
0.8582	High Similarity	NPD6031	Approved
0.855	High Similarity	NPD5752	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD4773	Phase 2
0.8472	Intermediate Similarity	NPD4772	Phase 2
0.8414	Intermediate Similarity	NPD7298	Approved
0.8321	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD1424	Approved
0.8248	Intermediate Similarity	NPD6895	Approved
0.8248	Intermediate Similarity	NPD6896	Approved
0.8099	Intermediate Similarity	NPD5241	Discontinued
0.8088	Intermediate Similarity	NPD2674	Phase 3
0.8079	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD2560	Approved
0.8054	Intermediate Similarity	NPD2563	Approved
0.8026	Intermediate Similarity	NPD6107	Approved
0.8026	Intermediate Similarity	NPD7802	Discontinued
0.7986	Intermediate Similarity	NPD3124	Discontinued
0.7974	Intermediate Similarity	NPD6071	Discontinued
0.7974	Intermediate Similarity	NPD4166	Phase 2
0.7974	Intermediate Similarity	NPD4010	Discontinued
0.7972	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7833	Phase 2
0.7947	Intermediate Similarity	NPD7831	Phase 2
0.7933	Intermediate Similarity	NPD5978	Approved
0.7933	Intermediate Similarity	NPD5977	Approved
0.7917	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD3145	Approved
0.7883	Intermediate Similarity	NPD3144	Approved
0.7881	Intermediate Similarity	NPD6788	Approved
0.7871	Intermediate Similarity	NPD2898	Approved
0.7867	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD7110	Phase 1
0.7847	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6687	Approved
0.7806	Intermediate Similarity	NPD6688	Approved
0.7793	Intermediate Similarity	NPD7124	Phase 2
0.7786	Intermediate Similarity	NPD2492	Phase 1
0.7785	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD8099	Discontinued
0.7771	Intermediate Similarity	NPD8252	Approved
0.7771	Intermediate Similarity	NPD8251	Approved
0.777	Intermediate Similarity	NPD3110	Approved
0.777	Intermediate Similarity	NPD3109	Approved
0.7761	Intermediate Similarity	NPD1420	Approved
0.7761	Intermediate Similarity	NPD1421	Approved
0.773	Intermediate Similarity	NPD6111	Discontinued
0.7727	Intermediate Similarity	NPD2667	Approved
0.7727	Intermediate Similarity	NPD2668	Approved
0.7722	Intermediate Similarity	NPD5313	Approved
0.7722	Intermediate Similarity	NPD5312	Approved
0.7722	Intermediate Similarity	NPD8156	Discontinued
0.7721	Intermediate Similarity	NPD7905	Discontinued
0.7708	Intermediate Similarity	NPD5177	Phase 3
0.7708	Intermediate Similarity	NPD4162	Approved
0.7708	Intermediate Similarity	NPD3060	Approved
0.7698	Intermediate Similarity	NPD4475	Approved
0.7698	Intermediate Similarity	NPD4474	Approved
0.7667	Intermediate Similarity	NPD6876	Approved
0.7667	Intermediate Similarity	NPD6875	Approved
0.766	Intermediate Similarity	NPD2653	Approved
0.7639	Intermediate Similarity	NPD7153	Discontinued
0.763	Intermediate Similarity	NPD1669	Approved
0.7625	Intermediate Similarity	NPD6297	Approved
0.76	Intermediate Similarity	NPD824	Approved
0.7597	Intermediate Similarity	NPD5283	Phase 1
0.7595	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3656	Approved
0.7566	Intermediate Similarity	NPD5720	Discontinued
0.7556	Intermediate Similarity	NPD2232	Approved
0.7556	Intermediate Similarity	NPD2233	Approved
0.7556	Intermediate Similarity	NPD2230	Approved
0.7534	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD2595	Approved
0.7519	Intermediate Similarity	NPD2594	Approved
0.7518	Intermediate Similarity	NPD4098	Discontinued
0.7517	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3051	Approved
0.75	Intermediate Similarity	NPD1039	Discontinued
0.75	Intermediate Similarity	NPD2161	Phase 2
0.75	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5677	Discontinued
0.7485	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2969	Approved
0.7468	Intermediate Similarity	NPD2970	Approved
0.7466	Intermediate Similarity	NPD4236	Phase 3
0.7466	Intermediate Similarity	NPD4237	Approved
0.745	Intermediate Similarity	NPD4123	Phase 3
0.7447	Intermediate Similarity	NPD3531	Approved
0.7447	Intermediate Similarity	NPD3530	Approved
0.7447	Intermediate Similarity	NPD3532	Approved
0.7439	Intermediate Similarity	NPD6851	Approved
0.7439	Intermediate Similarity	NPD6618	Phase 2
0.7439	Intermediate Similarity	NPD6853	Approved
0.7439	Intermediate Similarity	NPD8054	Approved
0.7439	Intermediate Similarity	NPD8053	Approved
0.7432	Intermediate Similarity	NPD2120	Phase 2
0.7431	Intermediate Similarity	NPD1753	Discontinued
0.7421	Intermediate Similarity	NPD2489	Approved
0.7421	Intermediate Similarity	NPD27	Approved
0.7421	Intermediate Similarity	NPD4481	Phase 3
0.7417	Intermediate Similarity	NPD4210	Discontinued
0.7413	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2238	Phase 2
0.7383	Intermediate Similarity	NPD2420	Approved
0.7383	Intermediate Similarity	NPD2421	Approved
0.7379	Intermediate Similarity	NPD3156	Discontinued
0.7376	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1336	Approved
0.7365	Intermediate Similarity	NPD3692	Discontinued
0.7351	Intermediate Similarity	NPD5976	Discontinued
0.7329	Intermediate Similarity	NPD1375	Discontinued
0.7315	Intermediate Similarity	NPD3845	Phase 1
0.7313	Intermediate Similarity	NPD2486	Discontinued
0.731	Intermediate Similarity	NPD3693	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD228	Approved
0.7297	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6748	Discontinued
0.7297	Intermediate Similarity	NPD6331	Phase 2
0.7292	Intermediate Similarity	NPD2986	Phase 2
0.7292	Intermediate Similarity	NPD2989	Phase 2
0.7285	Intermediate Similarity	NPD6090	Discontinued
0.7279	Intermediate Similarity	NPD3294	Phase 2
0.7273	Intermediate Similarity	NPD595	Approved
0.7273	Intermediate Similarity	NPD593	Approved
0.7267	Intermediate Similarity	NPD5297	Approved
0.7261	Intermediate Similarity	NPD5604	Discontinued
0.7261	Intermediate Similarity	NPD4055	Discovery
0.7259	Intermediate Similarity	NPD3445	Approved
0.7259	Intermediate Similarity	NPD6382	Discontinued
0.7259	Intermediate Similarity	NPD3443	Approved
0.7259	Intermediate Similarity	NPD3444	Approved
0.7254	Intermediate Similarity	NPD5109	Approved
0.7254	Intermediate Similarity	NPD5110	Phase 2
0.7254	Intermediate Similarity	NPD5111	Phase 2
0.7239	Intermediate Similarity	NPD3920	Phase 2
0.7237	Intermediate Similarity	NPD1914	Approved
0.7226	Intermediate Similarity	NPD3705	Approved
0.7219	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4675	Approved
0.7208	Intermediate Similarity	NPD4678	Approved
0.7203	Intermediate Similarity	NPD2245	Discovery
0.7202	Intermediate Similarity	NPD7291	Discontinued
0.72	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2922	Phase 1
0.7183	Intermediate Similarity	NPD1024	Discontinued
0.7179	Intermediate Similarity	NPD4585	Approved
0.7179	Intermediate Similarity	NPD5772	Approved
0.7179	Intermediate Similarity	NPD5773	Approved
0.7164	Intermediate Similarity	NPD3596	Phase 2
0.7162	Intermediate Similarity	NPD2170	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6873	Phase 2
0.7161	Intermediate Similarity	NPD6386	Approved
0.7161	Intermediate Similarity	NPD6385	Approved
0.7152	Intermediate Similarity	NPD7598	Phase 2
0.7143	Intermediate Similarity	NPD4005	Discontinued
0.7143	Intermediate Similarity	NPD4083	Discontinued
0.7143	Intermediate Similarity	NPD3053	Approved
0.7143	Intermediate Similarity	NPD3055	Approved
0.7133	Intermediate Similarity	NPD3301	Approved
0.7133	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4093	Discontinued
0.7124	Intermediate Similarity	NPD2122	Discontinued
0.7117	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD44	Approved
0.7114	Intermediate Similarity	NPD6364	Approved
0.7108	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1341	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2987	Approved
0.7092	Intermediate Similarity	NPD2990	Approved
0.7091	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3686	Approved
0.7078	Intermediate Similarity	NPD3687	Approved
0.7078	Intermediate Similarity	NPD2883	Discontinued
0.7076	Intermediate Similarity	NPD3921	Approved
0.7076	Intermediate Similarity	NPD3923	Approved
0.7076	Intermediate Similarity	NPD3922	Approved
0.7076	Intermediate Similarity	NPD3924	Approved
0.7075	Intermediate Similarity	NPD6380	Phase 1

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