NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	265.15
Volume:	289.627
LogP:	3.885
LogD:	3.384
LogS:	-2.875
# Rotatable Bonds:	1
TPSA:	12.47
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.783
Synthetic Accessibility Score:	2.703
Fsp3:	0.333
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:	-4.512
MDCK Permeability:	1.9310788047732785e-05
Pgp-inhibitor:	0.937
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.485
30% Bioavailability (F30%):	0.721

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.996
Plasma Protein Binding (PPB):	87.18183898925781%
Volume Distribution (VD):	2.915
Pgp-substrate:	7.5820722579956055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.662
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.277
CYP2C19-substrate:	0.961
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.582
CYP2D6-inhibitor:	0.976
CYP2D6-substrate:	0.943
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.89

ADMET: Excretion

Clearance (CL):	9.695
Half-life (T1/2):	0.21

ADMET: Toxicity

hERG Blockers:	0.879
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.231
AMES Toxicity:	0.799
Rat Oral Acute Toxicity:	0.582
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.351
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.831

Download Data

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

Natural Product: NPC470925

Natural Product ID:	NPC470925
*Common Name:**	2-Methoxy-6-Methyl-5,6,6A,7-Tetrahydro-4H-Dibenzo[De,G]Quinoline
IUPAC Name:	2-methoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
Synonyms:
Standard InCHIKey:	UVNXQKRQDGRTSE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H19NO/c1-19-8-7-13-9-14(20-2)11-16-15-6-4-3-5-12(15)10-17(19)18(13)16/h3-6,9,11,17H,7-8,10H2,1-2H3
SMILES:	COc1cc2CCN(C3c2c(c1)c1ccccc1C3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2316503
PubChem CID:	71716168
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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	Fruit	n.a.	n.a.	Database[FooDB]
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	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]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	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	1
Others	6

Activity Type	# Activity
Others	7

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	54.7	%	PMID[530779]
NPT2	Others	Unspecified	Inhibition	=	39.1	%	PMID[530779]
NPT27	Others	Unspecified	Inhibition	=	98.0	%	PMID[530779]
NPT27	Others	Unspecified	Inhibition	=	76.7	%	PMID[530779]
NPT2	Others	Unspecified	IC50	=	2000.0	nM	PMID[530779]
NPT2	Others	Unspecified	Inhibition	=	82.5	%	PMID[530779]
NPT2	Others	Unspecified	Inhibition	=	76.0	%	PMID[530779]

☑ 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 NPC470925 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	372
0.1-0.2	2004
0.2-0.3	10885
0.3-0.4	6465
0.4-0.5	9115
0.5-0.6	11184
0.6-0.7	1996
0.7-0.8	480
0.8-0.85	161
0.85-0.9	31
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9296	High Similarity	NPC326316
0.9296	High Similarity	NPC81733
0.9037	High Similarity	NPC325568
0.898	High Similarity	NPC476572
0.8973	High Similarity	NPC99659
0.8973	High Similarity	NPC325871
0.8912	High Similarity	NPC170503
0.8912	High Similarity	NPC203784
0.8912	High Similarity	NPC126519
0.8889	High Similarity	NPC92541
0.8889	High Similarity	NPC219162
0.8859	High Similarity	NPC266753
0.8859	High Similarity	NPC27410
0.8859	High Similarity	NPC160298
0.8859	High Similarity	NPC166014
0.8859	High Similarity	NPC232924
0.8859	High Similarity	NPC477559
0.8859	High Similarity	NPC306902
0.8786	High Similarity	NPC314682
0.875	High Similarity	NPC95075
0.875	High Similarity	NPC253883
0.875	High Similarity	NPC90844
0.875	High Similarity	NPC144863
0.8742	High Similarity	NPC1229
0.8723	High Similarity	NPC188163
0.8723	High Similarity	NPC474915
0.8723	High Similarity	NPC213206
0.8723	High Similarity	NPC328750
0.8716	High Similarity	NPC123323
0.869	High Similarity	NPC130941
0.8684	High Similarity	NPC225774
0.8627	High Similarity	NPC219341
0.8627	High Similarity	NPC24264
0.8627	High Similarity	NPC476432
0.8618	High Similarity	NPC324144
0.8601	High Similarity	NPC128019
0.8601	High Similarity	NPC136860
0.8601	High Similarity	NPC476567
0.8571	High Similarity	NPC298979
0.8571	High Similarity	NPC145832
0.8571	High Similarity	NPC81218
0.8571	High Similarity	NPC117188
0.8571	High Similarity	NPC205421
0.8571	High Similarity	NPC158376
0.8571	High Similarity	NPC474931
0.8571	High Similarity	NPC306555
0.8571	High Similarity	NPC12053
0.8571	High Similarity	NPC247389
0.8562	High Similarity	NPC477563
0.8562	High Similarity	NPC212794
0.8562	High Similarity	NPC306843
0.8562	High Similarity	NPC16805
0.8562	High Similarity	NPC96603
0.8562	High Similarity	NPC78222
0.8562	High Similarity	NPC136508
0.8562	High Similarity	NPC253043
0.8562	High Similarity	NPC13504
0.8562	High Similarity	NPC196447
0.8562	High Similarity	NPC167546
0.8562	High Similarity	NPC302527
0.8543	High Similarity	NPC221864
0.8516	High Similarity	NPC241055
0.8506	High Similarity	NPC304659
0.8506	High Similarity	NPC86144
0.8506	High Similarity	NPC35627
0.8506	High Similarity	NPC476573
0.8506	High Similarity	NPC81247
0.8493	Intermediate Similarity	NPC476144
0.8493	Intermediate Similarity	NPC51957
0.8493	Intermediate Similarity	NPC106295
0.8493	Intermediate Similarity	NPC16107
0.8493	Intermediate Similarity	NPC210437
0.8487	Intermediate Similarity	NPC119649
0.8487	Intermediate Similarity	NPC205255
0.8487	Intermediate Similarity	NPC230956
0.8487	Intermediate Similarity	NPC235143
0.8487	Intermediate Similarity	NPC271388
0.8483	Intermediate Similarity	NPC185838
0.8477	Intermediate Similarity	NPC79328
0.8467	Intermediate Similarity	NPC244112
0.8456	Intermediate Similarity	NPC470924
0.8456	Intermediate Similarity	NPC26601
0.8452	Intermediate Similarity	NPC210918
0.8442	Intermediate Similarity	NPC168409
0.8435	Intermediate Similarity	NPC7467
0.8431	Intermediate Similarity	NPC79402
0.8431	Intermediate Similarity	NPC80759
0.8421	Intermediate Similarity	NPC7393
0.8377	Intermediate Similarity	NPC189470
0.8367	Intermediate Similarity	NPC179825
0.8367	Intermediate Similarity	NPC191376
0.8367	Intermediate Similarity	NPC321505
0.8344	Intermediate Similarity	NPC76079
0.8344	Intermediate Similarity	NPC118274
0.8344	Intermediate Similarity	NPC168753
0.8333	Intermediate Similarity	NPC204947
0.8311	Intermediate Similarity	NPC246587
0.8311	Intermediate Similarity	NPC24233
0.8311	Intermediate Similarity	NPC147390
0.8311	Intermediate Similarity	NPC428
0.8311	Intermediate Similarity	NPC135538
0.8311	Intermediate Similarity	NPC476571
0.8311	Intermediate Similarity	NPC475959
0.8291	Intermediate Similarity	NPC19520
0.8291	Intermediate Similarity	NPC239775
0.8291	Intermediate Similarity	NPC149090
0.8289	Intermediate Similarity	NPC29647
0.8289	Intermediate Similarity	NPC186063
0.8258	Intermediate Similarity	NPC233650
0.8243	Intermediate Similarity	NPC476151
0.8239	Intermediate Similarity	NPC285941
0.8239	Intermediate Similarity	NPC66341
0.8239	Intermediate Similarity	NPC477020
0.8239	Intermediate Similarity	NPC192135
0.8228	Intermediate Similarity	NPC26240
0.8228	Intermediate Similarity	NPC6152
0.8228	Intermediate Similarity	NPC69712
0.8228	Intermediate Similarity	NPC477562
0.8205	Intermediate Similarity	NPC134858
0.8205	Intermediate Similarity	NPC209377
0.82	Intermediate Similarity	NPC151895
0.82	Intermediate Similarity	NPC88249
0.82	Intermediate Similarity	NPC97221
0.82	Intermediate Similarity	NPC192768
0.82	Intermediate Similarity	NPC220858
0.8199	Intermediate Similarity	NPC114364
0.8199	Intermediate Similarity	NPC320223
0.8187	Intermediate Similarity	NPC229166
0.8187	Intermediate Similarity	NPC199465
0.8187	Intermediate Similarity	NPC128560
0.8182	Intermediate Similarity	NPC477080
0.817	Intermediate Similarity	NPC25084
0.817	Intermediate Similarity	NPC247639
0.8153	Intermediate Similarity	NPC223077
0.8153	Intermediate Similarity	NPC193853
0.8153	Intermediate Similarity	NPC195392
0.8153	Intermediate Similarity	NPC56887
0.8148	Intermediate Similarity	NPC126284
0.8148	Intermediate Similarity	NPC220961
0.8146	Intermediate Similarity	NPC476568
0.8143	Intermediate Similarity	NPC89769
0.8143	Intermediate Similarity	NPC126859
0.8143	Intermediate Similarity	NPC259665
0.8143	Intermediate Similarity	NPC160193
0.8133	Intermediate Similarity	NPC207824
0.8133	Intermediate Similarity	NPC477565
0.8133	Intermediate Similarity	NPC103379
0.8133	Intermediate Similarity	NPC60538
0.8113	Intermediate Similarity	NPC152212
0.8108	Intermediate Similarity	NPC130926
0.8105	Intermediate Similarity	NPC41178
0.8105	Intermediate Similarity	NPC127674
0.8105	Intermediate Similarity	NPC5238
0.8105	Intermediate Similarity	NPC193949
0.8105	Intermediate Similarity	NPC189266
0.8105	Intermediate Similarity	NPC138487
0.8105	Intermediate Similarity	NPC204828
0.8105	Intermediate Similarity	NPC54379
0.8105	Intermediate Similarity	NPC39701
0.8105	Intermediate Similarity	NPC276588
0.8105	Intermediate Similarity	NPC184026
0.8105	Intermediate Similarity	NPC207757
0.8105	Intermediate Similarity	NPC295691
0.8105	Intermediate Similarity	NPC278799
0.8105	Intermediate Similarity	NPC110416
0.8105	Intermediate Similarity	NPC2413
0.8105	Intermediate Similarity	NPC469817
0.8105	Intermediate Similarity	NPC216459
0.8105	Intermediate Similarity	NPC172765
0.8105	Intermediate Similarity	NPC249797
0.8101	Intermediate Similarity	NPC150879
0.8101	Intermediate Similarity	NPC210140
0.8092	Intermediate Similarity	NPC233029
0.8092	Intermediate Similarity	NPC210148
0.8077	Intermediate Similarity	NPC60186
0.8071	Intermediate Similarity	NPC124802
0.8052	Intermediate Similarity	NPC146288
0.8049	Intermediate Similarity	NPC248642
0.8037	Intermediate Similarity	NPC474507
0.8037	Intermediate Similarity	NPC267408
0.8026	Intermediate Similarity	NPC76213
0.8026	Intermediate Similarity	NPC277669
0.8026	Intermediate Similarity	NPC8337
0.8026	Intermediate Similarity	NPC85747
0.8025	Intermediate Similarity	NPC287588
0.8025	Intermediate Similarity	NPC148709
0.8025	Intermediate Similarity	NPC112575
0.8025	Intermediate Similarity	NPC173416
0.8025	Intermediate Similarity	NPC476577
0.8	Intermediate Similarity	NPC302275
0.8	Intermediate Similarity	NPC253429
0.8	Intermediate Similarity	NPC66177
0.8	Intermediate Similarity	NPC268763
0.8	Intermediate Similarity	NPC156576
0.8	Intermediate Similarity	NPC8305
0.8	Intermediate Similarity	NPC172403
0.7988	Intermediate Similarity	NPC32413
0.7988	Intermediate Similarity	NPC474506
0.7987	Intermediate Similarity	NPC80129
0.7987	Intermediate Similarity	NPC187022

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 NPC470925 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	891
0.2-0.3	913
0.3-0.4	1565
0.4-0.5	2761
0.5-0.6	1926
0.6-0.7	688
0.7-0.8	163
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9037	High Similarity	NPD3109	Approved
0.9037	High Similarity	NPD3110	Approved
0.8723	High Similarity	NPD4664	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD4584	Approved
0.8425	Intermediate Similarity	NPD2420	Approved
0.8425	Intermediate Similarity	NPD2421	Approved
0.8299	Intermediate Similarity	NPD3124	Discontinued
0.8286	Intermediate Similarity	NPD4474	Approved
0.8286	Intermediate Similarity	NPD4475	Approved
0.8214	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD4017	Approved
0.8143	Intermediate Similarity	NPD5156	Approved
0.8143	Intermediate Similarity	NPD5155	Approved
0.8071	Intermediate Similarity	NPD3595	Approved
0.8071	Intermediate Similarity	NPD2605	Approved
0.8071	Intermediate Similarity	NPD3594	Approved
0.8071	Intermediate Similarity	NPD2606	Approved
0.8054	Intermediate Similarity	NPD7598	Phase 2
0.8041	Intermediate Similarity	NPD5241	Discontinued
0.8025	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4727	Phase 1
0.8	Intermediate Similarity	NPD3635	Approved
0.8	Intermediate Similarity	NPD3636	Approved
0.8	Intermediate Similarity	NPD3637	Approved
0.7987	Intermediate Similarity	NPD7298	Approved
0.7973	Intermediate Similarity	NPD5754	Discontinued
0.7895	Intermediate Similarity	NPD3641	Approved
0.7895	Intermediate Similarity	NPD3640	Phase 3
0.7895	Intermediate Similarity	NPD3639	Approved
0.7867	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6748	Discontinued
0.7842	Intermediate Similarity	NPD1669	Approved
0.7832	Intermediate Similarity	NPD5718	Phase 2
0.7812	Intermediate Similarity	NPD3051	Approved
0.7786	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6030	Approved
0.7778	Intermediate Similarity	NPD6031	Approved
0.7762	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1753	Discontinued
0.7755	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD3845	Phase 1
0.7736	Intermediate Similarity	NPD7400	Phase 3
0.7722	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD7294	Phase 1
0.7707	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4773	Phase 2
0.7692	Intermediate Similarity	NPD4772	Phase 2
0.7682	Intermediate Similarity	NPD3301	Approved
0.7676	Intermediate Similarity	NPD7905	Discontinued
0.7673	Intermediate Similarity	NPD7831	Phase 2
0.7673	Intermediate Similarity	NPD7833	Phase 2
0.7673	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2969	Approved
0.7654	Intermediate Similarity	NPD2970	Approved
0.7622	Intermediate Similarity	NPD8251	Approved
0.7622	Intermediate Similarity	NPD8099	Discontinued
0.7622	Intermediate Similarity	NPD8252	Approved
0.761	Intermediate Similarity	NPD6788	Approved
0.7609	Intermediate Similarity	NPD4093	Discontinued
0.7607	Intermediate Similarity	NPD4481	Phase 3
0.7607	Intermediate Similarity	NPD2489	Approved
0.7607	Intermediate Similarity	NPD27	Approved
0.7606	Intermediate Similarity	NPD4098	Discontinued
0.7605	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6025	Phase 1
0.7578	Intermediate Similarity	NPD6037	Discontinued
0.7576	Intermediate Similarity	NPD8156	Discontinued
0.7569	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD2668	Approved
0.7554	Intermediate Similarity	NPD2667	Approved
0.7548	Intermediate Similarity	NPD1914	Approved
0.7531	Intermediate Similarity	NPD7802	Discontinued
0.753	Intermediate Similarity	NPD7479	Phase 2
0.75	Intermediate Similarity	NPD2898	Approved
0.75	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4010	Discontinued
0.7483	Intermediate Similarity	NPD7037	Approved
0.7482	Intermediate Similarity	NPD2594	Approved
0.7482	Intermediate Similarity	NPD2595	Approved
0.7452	Intermediate Similarity	NPD6357	Discontinued
0.745	Intermediate Similarity	NPD6896	Approved
0.745	Intermediate Similarity	NPD6895	Approved
0.7417	Intermediate Similarity	NPD4726	Approved
0.7417	Intermediate Similarity	NPD4725	Approved
0.7417	Intermediate Similarity	NPD4721	Approved
0.7403	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6066	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2233	Approved
0.7394	Intermediate Similarity	NPD2230	Approved
0.7394	Intermediate Similarity	NPD2232	Approved
0.7383	Intermediate Similarity	NPD2989	Phase 2
0.7383	Intermediate Similarity	NPD2986	Phase 2
0.7378	Intermediate Similarity	NPD6747	Phase 1
0.7372	Intermediate Similarity	NPD6090	Discontinued
0.7368	Intermediate Similarity	NPD4257	Approved
0.7368	Intermediate Similarity	NPD4256	Phase 2
0.7358	Intermediate Similarity	NPD7438	Suspended
0.7357	Intermediate Similarity	NPD3444	Approved
0.7357	Intermediate Similarity	NPD3443	Approved
0.7357	Intermediate Similarity	NPD3445	Approved
0.7353	Intermediate Similarity	NPD2971	Approved
0.7353	Intermediate Similarity	NPD2968	Approved
0.7353	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1420	Approved
0.7343	Intermediate Similarity	NPD1421	Approved
0.7342	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5160	Discontinued
0.7333	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5977	Approved
0.7329	Intermediate Similarity	NPD5978	Approved
0.7325	Intermediate Similarity	NPD7427	Discontinued
0.732	Intermediate Similarity	NPD44	Approved
0.732	Intermediate Similarity	NPD6364	Approved
0.7317	Intermediate Similarity	NPD6107	Approved
0.731	Intermediate Similarity	NPD2987	Approved
0.731	Intermediate Similarity	NPD8053	Approved
0.731	Intermediate Similarity	NPD8054	Approved
0.731	Intermediate Similarity	NPD2990	Approved
0.7289	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5304	Approved
0.7286	Intermediate Similarity	NPD6580	Approved
0.7286	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6581	Approved
0.7286	Intermediate Similarity	NPD5303	Approved
0.7285	Intermediate Similarity	NPD4108	Discontinued
0.7283	Intermediate Similarity	NPD7906	Approved
0.7273	Intermediate Similarity	NPD4166	Phase 2
0.7266	Intermediate Similarity	NPD3596	Phase 2
0.7262	Intermediate Similarity	NPD42	Phase 2
0.7262	Intermediate Similarity	NPD6042	Phase 2
0.7251	Intermediate Similarity	NPD4578	Approved
0.7251	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD4577	Approved
0.7248	Intermediate Similarity	NPD2238	Phase 2
0.7234	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6382	Discontinued
0.723	Intermediate Similarity	NPD1039	Discontinued
0.7226	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3692	Discontinued
0.7219	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7018	Phase 2
0.7192	Intermediate Similarity	NPD6584	Phase 3
0.7192	Intermediate Similarity	NPD2195	Approved
0.7192	Intermediate Similarity	NPD2194	Approved
0.7184	Intermediate Similarity	NPD7291	Discontinued
0.7179	Intermediate Similarity	NPD6667	Approved
0.7179	Intermediate Similarity	NPD2120	Phase 2
0.7179	Intermediate Similarity	NPD6666	Approved
0.7176	Intermediate Similarity	NPD6297	Approved
0.7168	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2486	Discontinued
0.7162	Intermediate Similarity	NPD1024	Discontinued
0.716	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3364	Phase 3
0.7152	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7313	Approved
0.7151	Intermediate Similarity	NPD7311	Approved
0.7151	Intermediate Similarity	NPD7312	Approved
0.7151	Intermediate Similarity	NPD7310	Approved
0.7143	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7110	Phase 1
0.7133	Intermediate Similarity	NPD3294	Phase 2
0.7126	Intermediate Similarity	NPD6687	Approved
0.7126	Intermediate Similarity	NPD4663	Approved
0.7126	Intermediate Similarity	NPD6688	Approved
0.7117	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5967	Approved
0.7113	Intermediate Similarity	NPD1651	Approved
0.711	Intermediate Similarity	NPD7309	Approved
0.7103	Intermediate Similarity	NPD6539	Approved
0.7103	Intermediate Similarity	NPD6543	Approved
0.7103	Intermediate Similarity	NPD6542	Approved
0.7103	Intermediate Similarity	NPD6540	Phase 3
0.7102	Intermediate Similarity	NPD2488	Approved
0.7102	Intermediate Similarity	NPD2490	Approved
0.7097	Intermediate Similarity	NPD2459	Approved
0.7097	Intermediate Similarity	NPD2458	Approved
0.7097	Intermediate Similarity	NPD2460	Phase 3
0.7089	Intermediate Similarity	NPD7019	Approved
0.7089	Intermediate Similarity	NPD2874	Phase 2
0.7089	Intermediate Similarity	NPD7020	Approved
0.7089	Intermediate Similarity	NPD6322	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7030	Discontinued
0.7078	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7124	Phase 2
0.7067	Intermediate Similarity	NPD7477	Discontinued
0.7066	Intermediate Similarity	NPD6071	Discontinued
0.7063	Intermediate Similarity	NPD1751	Approved
0.7059	Intermediate Similarity	NPD6380	Phase 1
0.7059	Intermediate Similarity	NPD5312	Approved
0.7059	Intermediate Similarity	NPD5313	Approved
0.7055	Intermediate Similarity	NPD6738	Phase 2

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