NPASS Compound

Structure

NPC470924 OpenBabel07101719122D 23 26 0 0 1 0 0 0 0 0999 V2000 -2.2676 3.4586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 -1.8345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6328 -1.6123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7696 2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7696 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9036 2.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9036 0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4265 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4265 2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1715 2.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3890 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0376 2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0376 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 2.2515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6945 -0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1715 0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 2.7515 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6366 3.1342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 -1.3345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 -0.6235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 12 2 0 0 0 0 7 14 2 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 10 1 6 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 19 23 1 0 0 0 0 20 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	311.15
Volume:	324.503
LogP:	0.1
LogD:	1.372
LogS:	-0.85
# Rotatable Bonds:	2
TPSA:	41.52
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.63
Synthetic Accessibility Score:	3.644
Fsp3:	0.368
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:	-5.389
MDCK Permeability:	2.7199759642826393e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.785
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.492
Plasma Protein Binding (PPB):	42.493629455566406%
Volume Distribution (VD):	2.659
Pgp-substrate:	52.56150817871094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.142
CYP1A2-substrate:	0.869
CYP2C19-inhibitor:	0.084
CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.715
CYP2D6-inhibitor:	0.088
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.085
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	7.183
Half-life (T1/2):	0.864

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.45
Rat Oral Acute Toxicity:	0.246
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.054
Carcinogencity:	0.128
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.229

Download Data

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

Natural Product: NPC470924

Natural Product ID:	NPC470924
*Common Name:**	Nuciferine N-Oxide
IUPAC Name:	(6aR)-1,2-dimethoxy-6-methyl-6-oxido-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-6-ium
Synonyms:	Nuciferine N-Oxide
Standard InCHIKey:	SAWSWZQULQPSLR-IWPPFLRJSA-N
Standard InCHI:	InChI=1S/C19H21NO3/c1-20(21)9-8-13-11-16(22-2)19(23-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3/t15-,20?/m1/s1
SMILES:	COc1cc2CCN(=O)([C@H]3c2c(c1OC)c1ccccc1C3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2316498
PubChem CID:	71720427
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	7

Activity Type	# Activity
Others	8

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	-0.1	%	PMID[460851]
NPT2	Others	Unspecified	Inhibition	=	-3.2	%	PMID[460851]
NPT2	Others	Unspecified	Inhibition	=	-4.8	%	PMID[460851]
NPT27	Others	Unspecified	Inhibition	=	82.0	%	PMID[460851]
NPT27	Others	Unspecified	Inhibition	=	86.0	%	PMID[460851]
NPT2	Others	Unspecified	IC50	=	43000.0	nM	PMID[460851]
NPT2	Others	Unspecified	Inhibition	=	88.4	%	PMID[460851]
NPT2	Others	Unspecified	Inhibition	=	33.7	%	PMID[460851]

☑ 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 NPC470924 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	394
0.1-0.2	2068
0.2-0.3	11221
0.3-0.4	6596
0.4-0.5	8299
0.5-0.6	10997
0.6-0.7	2314
0.7-0.8	511
0.8-0.85	142
0.85-0.9	130
0.9-0.95	22
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9128	High Similarity	NPC81733
0.9128	High Similarity	NPC326316
0.8882	High Similarity	NPC477560
0.8831	High Similarity	NPC476572
0.8828	High Similarity	NPC210086
0.8824	High Similarity	NPC99659
0.8824	High Similarity	NPC325871
0.8766	High Similarity	NPC170503
0.8766	High Similarity	NPC477133
0.8766	High Similarity	NPC126519
0.8766	High Similarity	NPC203784
0.8766	High Similarity	NPC477132
0.8742	High Similarity	NPC44869
0.872	High Similarity	NPC233718
0.8718	High Similarity	NPC166014
0.8718	High Similarity	NPC160298
0.8718	High Similarity	NPC27410
0.8718	High Similarity	NPC477559
0.8718	High Similarity	NPC306902
0.8718	High Similarity	NPC266753
0.8718	High Similarity	NPC232924
0.8693	High Similarity	NPC37272
0.8639	High Similarity	NPC314682
0.8609	High Similarity	NPC476144
0.8609	High Similarity	NPC16107
0.8609	High Similarity	NPC210437
0.8609	High Similarity	NPC51957
0.8609	High Similarity	NPC106295
0.8581	High Similarity	NPC328750
0.8581	High Similarity	NPC188163
0.8581	High Similarity	NPC213206
0.8581	High Similarity	NPC474915
0.8553	High Similarity	NPC7467
0.8553	High Similarity	NPC225774
0.85	High Similarity	NPC219341
0.85	High Similarity	NPC476432
0.85	High Similarity	NPC24264
0.8491	Intermediate Similarity	NPC324144
0.8467	Intermediate Similarity	NPC128019
0.8467	Intermediate Similarity	NPC136860
0.8467	Intermediate Similarity	NPC476567
0.8456	Intermediate Similarity	NPC470925
0.8447	Intermediate Similarity	NPC247389
0.8447	Intermediate Similarity	NPC158376
0.8447	Intermediate Similarity	NPC145832
0.8447	Intermediate Similarity	NPC298979
0.8447	Intermediate Similarity	NPC117188
0.8447	Intermediate Similarity	NPC81218
0.8447	Intermediate Similarity	NPC205421
0.8447	Intermediate Similarity	NPC306555
0.8447	Intermediate Similarity	NPC12053
0.8447	Intermediate Similarity	NPC474931
0.8438	Intermediate Similarity	NPC78222
0.8438	Intermediate Similarity	NPC253043
0.8438	Intermediate Similarity	NPC212794
0.8438	Intermediate Similarity	NPC196447
0.8438	Intermediate Similarity	NPC306843
0.8438	Intermediate Similarity	NPC477563
0.8438	Intermediate Similarity	NPC76116
0.8438	Intermediate Similarity	NPC302527
0.8438	Intermediate Similarity	NPC16805
0.8438	Intermediate Similarity	NPC136508
0.8438	Intermediate Similarity	NPC167546
0.8438	Intermediate Similarity	NPC96603
0.8438	Intermediate Similarity	NPC13504
0.8405	Intermediate Similarity	NPC10871
0.8395	Intermediate Similarity	NPC241055
0.8385	Intermediate Similarity	NPC86144
0.8385	Intermediate Similarity	NPC304659
0.8385	Intermediate Similarity	NPC35627
0.8385	Intermediate Similarity	NPC476573
0.8385	Intermediate Similarity	NPC81247
0.8377	Intermediate Similarity	NPC92541
0.8377	Intermediate Similarity	NPC219162
0.8375	Intermediate Similarity	NPC1229
0.8366	Intermediate Similarity	NPC476151
0.8355	Intermediate Similarity	NPC130926
0.8355	Intermediate Similarity	NPC185838
0.8354	Intermediate Similarity	NPC475326
0.8344	Intermediate Similarity	NPC329911
0.8333	Intermediate Similarity	NPC210918
0.8323	Intermediate Similarity	NPC168409
0.8302	Intermediate Similarity	NPC118804
0.8291	Intermediate Similarity	NPC323443
0.8291	Intermediate Similarity	NPC180756
0.8282	Intermediate Similarity	NPC164429
0.8282	Intermediate Similarity	NPC160570
0.8276	Intermediate Similarity	NPC160193
0.8261	Intermediate Similarity	NPC189470
0.8258	Intermediate Similarity	NPC103379
0.8258	Intermediate Similarity	NPC477565
0.8247	Intermediate Similarity	NPC253883
0.8247	Intermediate Similarity	NPC95075
0.8247	Intermediate Similarity	NPC321505
0.8247	Intermediate Similarity	NPC144863
0.8247	Intermediate Similarity	NPC191376
0.8247	Intermediate Similarity	NPC90844
0.8247	Intermediate Similarity	NPC179825
0.8232	Intermediate Similarity	NPC118274
0.8232	Intermediate Similarity	NPC168753
0.8228	Intermediate Similarity	NPC244112
0.8228	Intermediate Similarity	NPC184026
0.8228	Intermediate Similarity	NPC138487
0.8228	Intermediate Similarity	NPC110416
0.8228	Intermediate Similarity	NPC189266
0.8228	Intermediate Similarity	NPC204828
0.8228	Intermediate Similarity	NPC469817
0.8228	Intermediate Similarity	NPC295691
0.8228	Intermediate Similarity	NPC127674
0.8228	Intermediate Similarity	NPC54379
0.8228	Intermediate Similarity	NPC278799
0.8228	Intermediate Similarity	NPC2413
0.8228	Intermediate Similarity	NPC216459
0.8228	Intermediate Similarity	NPC276588
0.8228	Intermediate Similarity	NPC5238
0.8228	Intermediate Similarity	NPC41178
0.8228	Intermediate Similarity	NPC39701
0.8228	Intermediate Similarity	NPC172765
0.8228	Intermediate Similarity	NPC207757
0.8228	Intermediate Similarity	NPC193949
0.8228	Intermediate Similarity	NPC249797
0.8221	Intermediate Similarity	NPC204947
0.8194	Intermediate Similarity	NPC476571
0.8194	Intermediate Similarity	NPC246587
0.8194	Intermediate Similarity	NPC135538
0.8194	Intermediate Similarity	NPC130941
0.8194	Intermediate Similarity	NPC24233
0.8194	Intermediate Similarity	NPC475959
0.8194	Intermediate Similarity	NPC428
0.8194	Intermediate Similarity	NPC147390
0.8182	Intermediate Similarity	NPC149090
0.8182	Intermediate Similarity	NPC19520
0.8182	Intermediate Similarity	NPC239775
0.8176	Intermediate Similarity	NPC146288
0.8153	Intermediate Similarity	NPC476579
0.8133	Intermediate Similarity	NPC66341
0.8133	Intermediate Similarity	NPC253429
0.8133	Intermediate Similarity	NPC192135
0.8133	Intermediate Similarity	NPC285941
0.8133	Intermediate Similarity	NPC477020
0.8121	Intermediate Similarity	NPC26240
0.8121	Intermediate Similarity	NPC6152
0.8121	Intermediate Similarity	NPC69712
0.8121	Intermediate Similarity	NPC475828
0.8121	Intermediate Similarity	NPC477562
0.8095	Intermediate Similarity	NPC114364
0.8095	Intermediate Similarity	NPC320223
0.8089	Intermediate Similarity	NPC220858
0.8089	Intermediate Similarity	NPC151895
0.8089	Intermediate Similarity	NPC274026
0.8089	Intermediate Similarity	NPC97221
0.8089	Intermediate Similarity	NPC192768
0.8089	Intermediate Similarity	NPC88249
0.8084	Intermediate Similarity	NPC229166
0.8084	Intermediate Similarity	NPC199465
0.8084	Intermediate Similarity	NPC128560
0.8075	Intermediate Similarity	NPC477080
0.8063	Intermediate Similarity	NPC234392
0.8063	Intermediate Similarity	NPC31311
0.8047	Intermediate Similarity	NPC220961
0.8047	Intermediate Similarity	NPC126284
0.8038	Intermediate Similarity	NPC476568
0.8038	Intermediate Similarity	NPC8337
0.8038	Intermediate Similarity	NPC85747
0.8025	Intermediate Similarity	NPC207824
0.8025	Intermediate Similarity	NPC60538
0.8012	Intermediate Similarity	NPC152212
0.8	Intermediate Similarity	NPC78733
0.7988	Intermediate Similarity	NPC39103
0.7988	Intermediate Similarity	NPC2770
0.7987	Intermediate Similarity	NPC26601
0.7987	Intermediate Similarity	NPC82285
0.7987	Intermediate Similarity	NPC233029
0.7987	Intermediate Similarity	NPC148898
0.7987	Intermediate Similarity	NPC133011
0.7987	Intermediate Similarity	NPC210148
0.7975	Intermediate Similarity	NPC60186
0.7953	Intermediate Similarity	NPC248642
0.7952	Intermediate Similarity	NPC470324
0.795	Intermediate Similarity	NPC147091
0.795	Intermediate Similarity	NPC247639
0.795	Intermediate Similarity	NPC25084
0.7941	Intermediate Similarity	NPC267408
0.7941	Intermediate Similarity	NPC474507
0.7939	Intermediate Similarity	NPC124657
0.7937	Intermediate Similarity	NPC477564
0.7937	Intermediate Similarity	NPC2295
0.7929	Intermediate Similarity	NPC112575
0.7929	Intermediate Similarity	NPC148709
0.7929	Intermediate Similarity	NPC173416
0.7929	Intermediate Similarity	NPC476577
0.7927	Intermediate Similarity	NPC233650
0.7925	Intermediate Similarity	NPC76213
0.7925	Intermediate Similarity	NPC277669
0.7914	Intermediate Similarity	NPC205167
0.7914	Intermediate Similarity	NPC249274
0.7907	Intermediate Similarity	NPC156576
0.7907	Intermediate Similarity	NPC302275
0.7895	Intermediate Similarity	NPC474506
0.7895	Intermediate Similarity	NPC32413

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 NPC470924 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	864
0.2-0.3	1049
0.3-0.4	1907
0.4-0.5	2651
0.5-0.6	1719
0.6-0.7	569
0.7-0.8	140
0.8-0.85	16
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8609	High Similarity	NPD4584	Approved
0.8581	High Similarity	NPD4664	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD4017	Approved
0.8025	Intermediate Similarity	NPD3641	Approved
0.8025	Intermediate Similarity	NPD3640	Phase 3
0.8025	Intermediate Similarity	NPD3639	Approved
0.8	Intermediate Similarity	NPD2969	Approved
0.8	Intermediate Similarity	NPD2970	Approved
0.7952	Intermediate Similarity	NPD2489	Approved
0.7952	Intermediate Similarity	NPD4481	Phase 3
0.7952	Intermediate Similarity	NPD2898	Approved
0.7952	Intermediate Similarity	NPD27	Approved
0.7949	Intermediate Similarity	NPD2420	Approved
0.7949	Intermediate Similarity	NPD2421	Approved
0.7939	Intermediate Similarity	NPD3051	Approved
0.7888	Intermediate Similarity	NPD7298	Approved
0.7867	Intermediate Similarity	NPD3110	Approved
0.7867	Intermediate Similarity	NPD3109	Approved
0.7826	Intermediate Similarity	NPD4773	Phase 2
0.7826	Intermediate Similarity	NPD4772	Phase 2
0.7818	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD5241	Discontinued
0.7688	Intermediate Similarity	NPD7311	Approved
0.7688	Intermediate Similarity	NPD6030	Approved
0.7688	Intermediate Similarity	NPD7313	Approved
0.7688	Intermediate Similarity	NPD7310	Approved
0.7688	Intermediate Similarity	NPD6031	Approved
0.7688	Intermediate Similarity	NPD7312	Approved
0.7647	Intermediate Similarity	NPD8251	Approved
0.7647	Intermediate Similarity	NPD8252	Approved
0.7647	Intermediate Similarity	NPD8099	Discontinued
0.7644	Intermediate Similarity	NPD7309	Approved
0.7636	Intermediate Similarity	NPD6788	Approved
0.7616	Intermediate Similarity	NPD5718	Phase 2
0.761	Intermediate Similarity	NPD3124	Discontinued
0.7602	Intermediate Similarity	NPD8156	Discontinued
0.7515	Intermediate Similarity	NPD6071	Discontinued
0.7486	Intermediate Similarity	NPD2971	Approved
0.7486	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD2968	Approved
0.7485	Intermediate Similarity	NPD7831	Phase 2
0.7485	Intermediate Similarity	NPD7833	Phase 2
0.7485	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD2560	Approved
0.747	Intermediate Similarity	NPD2563	Approved
0.7456	Intermediate Similarity	NPD6107	Approved
0.7453	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7906	Approved
0.7412	Intermediate Similarity	NPD4166	Phase 2
0.7412	Intermediate Similarity	NPD4010	Discontinued
0.741	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4577	Approved
0.7386	Intermediate Similarity	NPD4578	Approved
0.7384	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7802	Discontinued
0.7346	Intermediate Similarity	NPD1424	Approved
0.7345	Intermediate Similarity	NPD8053	Approved
0.7345	Intermediate Similarity	NPD8054	Approved
0.7329	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5754	Discontinued
0.7301	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4663	Approved
0.7261	Intermediate Similarity	NPD6896	Approved
0.7261	Intermediate Similarity	NPD6895	Approved
0.7238	Intermediate Similarity	NPD2488	Approved
0.7238	Intermediate Similarity	NPD2490	Approved
0.7226	Intermediate Similarity	NPD4475	Approved
0.7226	Intermediate Similarity	NPD4474	Approved
0.7222	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3845	Phase 1
0.72	Intermediate Similarity	NPD5313	Approved
0.72	Intermediate Similarity	NPD5312	Approved
0.7178	Intermediate Similarity	NPD7598	Phase 2
0.7169	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6688	Approved
0.7168	Intermediate Similarity	NPD6687	Approved
0.7166	Intermediate Similarity	NPD4482	Phase 3
0.716	Intermediate Similarity	NPD5978	Approved
0.716	Intermediate Similarity	NPD5977	Approved
0.7152	Intermediate Similarity	NPD4727	Phase 1
0.7143	Intermediate Similarity	NPD5177	Phase 3
0.7128	Intermediate Similarity	NPD3533	Approved
0.7128	Intermediate Similarity	NPD3448	Approved
0.7128	Intermediate Similarity	NPD2491	Approved
0.7128	Intermediate Similarity	NPD2972	Approved
0.7119	Intermediate Similarity	NPD6297	Approved
0.7118	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4107	Approved
0.7107	Intermediate Similarity	NPD1753	Discontinued
0.7099	Intermediate Similarity	NPD6748	Discontinued
0.7078	Intermediate Similarity	NPD3636	Approved
0.7078	Intermediate Similarity	NPD3637	Approved
0.7078	Intermediate Similarity	NPD3635	Approved
0.7055	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD2975	Approved
0.7043	Intermediate Similarity	NPD2973	Approved
0.7043	Intermediate Similarity	NPD2974	Approved
0.7037	Intermediate Similarity	NPD3057	Approved
0.7033	Intermediate Similarity	NPD7291	Discontinued
0.7032	Intermediate Similarity	NPD3595	Approved
0.7032	Intermediate Similarity	NPD3594	Approved
0.7032	Intermediate Similarity	NPD2605	Approved
0.7032	Intermediate Similarity	NPD2606	Approved
0.7017	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2674	Phase 3
0.6994	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6037	Discontinued
0.6989	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5155	Approved
0.6987	Remote Similarity	NPD5156	Approved
0.6982	Remote Similarity	NPD7110	Phase 1
0.6982	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4055	Discovery
0.6961	Remote Similarity	NPD6853	Approved
0.6961	Remote Similarity	NPD6851	Approved
0.6951	Remote Similarity	NPD3692	Discontinued
0.6946	Remote Similarity	NPD5976	Discontinued
0.6943	Remote Similarity	NPD1039	Discontinued
0.6943	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7400	Phase 3
0.6931	Remote Similarity	NPD4580	Approved
0.6909	Remote Similarity	NPD7124	Phase 2
0.6895	Remote Similarity	NPD2493	Approved
0.6895	Remote Similarity	NPD3450	Approved
0.6895	Remote Similarity	NPD2494	Approved
0.6895	Remote Similarity	NPD3452	Approved
0.6893	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6090	Discontinued
0.6883	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD8095	Phase 1
0.6875	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4257	Approved
0.6871	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4256	Phase 2
0.6852	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5160	Discontinued
0.6845	Remote Similarity	NPD1914	Approved
0.6845	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7248	Discontinued
0.6842	Remote Similarity	NPD5720	Discontinued
0.6837	Remote Similarity	NPD5676	Approved
0.6835	Remote Similarity	NPD3145	Approved
0.6835	Remote Similarity	NPD3144	Approved
0.6825	Remote Similarity	NPD4420	Approved
0.6824	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1421	Approved
0.6818	Remote Similarity	NPD1669	Approved
0.6818	Remote Similarity	NPD1420	Approved
0.681	Remote Similarity	NPD4725	Approved
0.681	Remote Similarity	NPD4721	Approved
0.681	Remote Similarity	NPD4726	Approved
0.6802	Remote Similarity	NPD4585	Approved
0.6795	Remote Similarity	NPD7905	Discontinued
0.6788	Remote Similarity	NPD4582	Approved
0.6788	Remote Similarity	NPD4583	Approved
0.6788	Remote Similarity	NPD6331	Phase 2
0.6778	Remote Similarity	NPD3920	Phase 2
0.6776	Remote Similarity	NPD2667	Approved
0.6776	Remote Similarity	NPD2668	Approved
0.6776	Remote Similarity	NPD6618	Phase 2
0.6772	Remote Similarity	NPD1024	Discontinued
0.677	Remote Similarity	NPD2492	Phase 1
0.6757	Remote Similarity	NPD3398	Discontinued
0.6755	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6612	Phase 2
0.6753	Remote Similarity	NPD2232	Approved
0.6753	Remote Similarity	NPD2230	Approved
0.6753	Remote Similarity	NPD2233	Approved
0.674	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4004	Approved
0.6736	Remote Similarity	NPD4002	Approved
0.6731	Remote Similarity	NPD4098	Discontinued
0.673	Remote Similarity	NPD7294	Phase 1
0.6728	Remote Similarity	NPD2200	Suspended
0.6728	Remote Similarity	NPD6111	Discontinued
0.6727	Remote Similarity	NPD4237	Approved
0.6727	Remote Similarity	NPD4236	Phase 3
0.6727	Remote Similarity	NPD4162	Approved
0.6727	Remote Similarity	NPD3060	Approved
0.6725	Remote Similarity	NPD6876	Approved
0.6725	Remote Similarity	NPD6875	Approved
0.6707	Remote Similarity	NPD2120	Phase 2
0.6705	Remote Similarity	NPD2904	Discontinued
0.6705	Remote Similarity	NPD5677	Discontinued
0.6702	Remote Similarity	NPD7262	Phase 1
0.6701	Remote Similarity	NPD4040	Phase 1
0.6685	Remote Similarity	NPD7479	Phase 2
0.6684	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5005	Approved
0.6684	Remote Similarity	NPD4859	Phase 1
0.6684	Remote Similarity	NPD7034	Discontinued

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