NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	235.14
Volume:	263.54
LogP:	4.135
LogD:	3.227
LogS:	-3.38
# Rotatable Bonds:	0
TPSA:	3.24
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.676
Synthetic Accessibility Score:	2.584
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.493
MDCK Permeability:	2.1450532585731708e-05
Pgp-inhibitor:	0.707
Pgp-substrate:	0.858
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.864
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.98
Plasma Protein Binding (PPB):	93.12584686279297%
Volume Distribution (VD):	3.366
Pgp-substrate:	4.515598297119141%

ADMET: Metabolism

CYP1A2-inhibitor:	0.695
CYP1A2-substrate:	0.884
CYP2C19-inhibitor:	0.414
CYP2C19-substrate:	0.94
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.307
CYP2D6-inhibitor:	0.984
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.821

ADMET: Excretion

Clearance (CL):	9.843
Half-life (T1/2):	0.201

ADMET: Toxicity

hERG Blockers:	0.741
Human Hepatotoxicity (H-HT):	0.509
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.904
Rat Oral Acute Toxicity:	0.499
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.257
Carcinogencity:	0.37
Eye Corrosion:	0.003
Eye Irritation:	0.019
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: NPC239854

Natural Product ID:	NPC239854
*Common Name:**	6-Methyl-5,6,6A,7-Tetrahydro-4H-Dibenzo[De,G]Quinoline
IUPAC Name:	(6aR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
Synonyms:
Standard InCHIKey:	BZKUYNBAFQJRDM-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C17H17N/c1-18-10-9-12-6-4-8-15-14-7-3-2-5-13(14)11-16(18)17(12)15/h2-8,16H,9-11H2,1H3/t16-/m1/s1
SMILES:	CN1CCc2c3[C@H]1Cc1ccccc1c3ccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL281357
PubChem CID:	10421583
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]
NPO29514	Stizolobium capitatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29514	Stizolobium capitatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29272	Paronychia argentea	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28458	Coccoloba dugandiana	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28873	Epinetrum mangenotii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29520	Curculigo breviscapa	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29514	Stizolobium capitatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29235	Musca autumnalis	Species	Muscidae	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
Ki	9
Others	7

Activity Type	# Activity
Individual Protein	9
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4041	Individual Protein	Serotonin 7 (5-HT7) receptor	Rattus norvegicus	Ki	=	88.0	nM	PMID[558530]
NPT243	Individual Protein	Dopamine D2 receptor	Homo sapiens	Ki	=	527.0	nM	PMID[558530]
NPT288	Individual Protein	Serotonin 1a (5-HT1a) receptor	Rattus norvegicus	Ki	=	80.0	nM	PMID[558531]
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	Ki	=	717.0	nM	PMID[558531]
NPT243	Individual Protein	Dopamine D2 receptor	Homo sapiens	Ki	=	527.0	nM	PMID[558531]
NPT4041	Individual Protein	Serotonin 7 (5-HT7) receptor	Rattus norvegicus	Ki	=	88.0	nM	PMID[558532]
NPT243	Individual Protein	Dopamine D2 receptor	Homo sapiens	Ki	=	527.0	nM	PMID[558532]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	Ki	=	80.0	nM	PMID[558530]
NPT92	Individual Protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	Ki	=	80.0	nM	PMID[558532]
NPT2	Others	Unspecified		Inhibition	=	42.7	%	PMID[558533]
NPT2	Others	Unspecified		Inhibition	=	30.0	%	PMID[558533]
NPT27	Others	Unspecified		Inhibition	=	41.1	%	PMID[558533]
NPT27	Others	Unspecified		Inhibition	=	86.0	%	PMID[558533]
NPT2	Others	Unspecified		IC50	=	5900.0	nM	PMID[558533]
NPT2	Others	Unspecified		Inhibition	=	22.3	%	PMID[558533]
NPT2	Others	Unspecified		Inhibition	=	72.2	%	PMID[558533]
NPT2	Others	Unspecified		Inhibition	=	59.2	%	PMID[558533]

☑ 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 NPC239854 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	619
0.1-0.2	4839
0.2-0.3	13547
0.3-0.4	16502
0.4-0.5	5624
0.5-0.6	1353
0.6-0.7	179
0.7-0.8	27
0.8-0.85	4
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9043	High Similarity	NPC470926
0.8384	Intermediate Similarity	NPC329430
0.8365	Intermediate Similarity	NPC474695
0.8191	Intermediate Similarity	NPC104070
0.781	Intermediate Similarity	NPC474582
0.7576	Intermediate Similarity	NPC258046
0.7447	Intermediate Similarity	NPC271642
0.7407	Intermediate Similarity	NPC291610
0.7374	Intermediate Similarity	NPC169016
0.734	Intermediate Similarity	NPC98976
0.7327	Intermediate Similarity	NPC60408
0.7288	Intermediate Similarity	NPC320656
0.7245	Intermediate Similarity	NPC231986
0.7238	Intermediate Similarity	NPC322040
0.7143	Intermediate Similarity	NPC315216
0.7121	Intermediate Similarity	NPC470925
0.7107	Intermediate Similarity	NPC475915
0.71	Intermediate Similarity	NPC119677
0.7094	Intermediate Similarity	NPC246904
0.7041	Intermediate Similarity	NPC159661
0.703	Intermediate Similarity	NPC133162
0.7016	Intermediate Similarity	NPC79698
0.7	Intermediate Similarity	NPC264580
0.6979	Remote Similarity	NPC307195
0.6967	Remote Similarity	NPC314192
0.6939	Remote Similarity	NPC245896
0.6939	Remote Similarity	NPC12857
0.6939	Remote Similarity	NPC66270
0.693	Remote Similarity	NPC79618
0.693	Remote Similarity	NPC434
0.6915	Remote Similarity	NPC72670
0.6891	Remote Similarity	NPC473573
0.6875	Remote Similarity	NPC126859
0.6875	Remote Similarity	NPC259665
0.6875	Remote Similarity	NPC258492
0.6875	Remote Similarity	NPC89769
0.6875	Remote Similarity	NPC96835
0.6842	Remote Similarity	NPC193578
0.6842	Remote Similarity	NPC87099
0.6842	Remote Similarity	NPC158028
0.6842	Remote Similarity	NPC1008
0.6842	Remote Similarity	NPC226999
0.6842	Remote Similarity	NPC135433
0.6842	Remote Similarity	NPC280135
0.6842	Remote Similarity	NPC39799
0.6837	Remote Similarity	NPC3190
0.6837	Remote Similarity	NPC325662
0.6837	Remote Similarity	NPC249018
0.6837	Remote Similarity	NPC98269
0.6822	Remote Similarity	NPC473962
0.6809	Remote Similarity	NPC139416
0.6809	Remote Similarity	NPC213570
0.6809	Remote Similarity	NPC246822
0.68	Remote Similarity	NPC50063
0.6797	Remote Similarity	NPC124802
0.6771	Remote Similarity	NPC54269
0.6754	Remote Similarity	NPC473418
0.6754	Remote Similarity	NPC167336
0.6744	Remote Similarity	NPC126458
0.6719	Remote Similarity	NPC8305
0.6719	Remote Similarity	NPC66177
0.6719	Remote Similarity	NPC268763
0.6667	Remote Similarity	NPC108800
0.6667	Remote Similarity	NPC290638
0.662	Remote Similarity	NPC326316
0.662	Remote Similarity	NPC81733
0.6606	Remote Similarity	NPC469330
0.66	Remote Similarity	NPC255345
0.6591	Remote Similarity	NPC325568
0.6566	Remote Similarity	NPC139658
0.6562	Remote Similarity	NPC251490
0.6562	Remote Similarity	NPC252794
0.6547	Remote Similarity	NPC469735
0.6542	Remote Similarity	NPC176858
0.6531	Remote Similarity	NPC113000
0.6531	Remote Similarity	NPC112609
0.6531	Remote Similarity	NPC122327
0.6525	Remote Similarity	NPC65855
0.6525	Remote Similarity	NPC292758
0.6512	Remote Similarity	NPC478079
0.6509	Remote Similarity	NPC17497
0.6509	Remote Similarity	NPC305602
0.6504	Remote Similarity	NPC313449
0.65	Remote Similarity	NPC469740
0.6481	Remote Similarity	NPC191444
0.6479	Remote Similarity	NPC206592
0.6466	Remote Similarity	NPC313352
0.6465	Remote Similarity	NPC276699
0.6454	Remote Similarity	NPC90844
0.6454	Remote Similarity	NPC144863
0.6454	Remote Similarity	NPC95075
0.6454	Remote Similarity	NPC253883
0.6446	Remote Similarity	NPC187036
0.6429	Remote Similarity	NPC1901
0.6421	Remote Similarity	NPC6107
0.6421	Remote Similarity	NPC267443
0.64	Remote Similarity	NPC110264
0.6396	Remote Similarity	NPC108339
0.6395	Remote Similarity	NPC476572
0.6392	Remote Similarity	NPC219246
0.6391	Remote Similarity	NPC149379
0.6383	Remote Similarity	NPC291066
0.6378	Remote Similarity	NPC109151
0.6371	Remote Similarity	NPC192209
0.637	Remote Similarity	NPC325871
0.637	Remote Similarity	NPC99659
0.6364	Remote Similarity	NPC299134
0.6364	Remote Similarity	NPC92541
0.6364	Remote Similarity	NPC33421
0.6364	Remote Similarity	NPC219162
0.6357	Remote Similarity	NPC116519
0.6355	Remote Similarity	NPC473031
0.635	Remote Similarity	NPC243162
0.6339	Remote Similarity	NPC471320
0.6339	Remote Similarity	NPC471319
0.6336	Remote Similarity	NPC40488
0.6327	Remote Similarity	NPC170503
0.6327	Remote Similarity	NPC203784
0.6327	Remote Similarity	NPC126519
0.6316	Remote Similarity	NPC289915
0.6316	Remote Similarity	NPC113837
0.6309	Remote Similarity	NPC477559
0.6309	Remote Similarity	NPC306902
0.6309	Remote Similarity	NPC166014
0.6309	Remote Similarity	NPC27410
0.6309	Remote Similarity	NPC232924
0.6309	Remote Similarity	NPC160298
0.6309	Remote Similarity	NPC266753
0.6303	Remote Similarity	NPC302790
0.6296	Remote Similarity	NPC111233
0.629	Remote Similarity	NPC313673
0.6286	Remote Similarity	NPC474088
0.6277	Remote Similarity	NPC113670
0.6263	Remote Similarity	NPC244738
0.6262	Remote Similarity	NPC203076
0.6239	Remote Similarity	NPC470877
0.6233	Remote Similarity	NPC26601
0.6232	Remote Similarity	NPC169433
0.6231	Remote Similarity	NPC122718
0.6225	Remote Similarity	NPC1229
0.6224	Remote Similarity	NPC263385
0.6224	Remote Similarity	NPC229235
0.6216	Remote Similarity	NPC473661
0.6211	Remote Similarity	NPC155172
0.6211	Remote Similarity	NPC32312
0.621	Remote Similarity	NPC288232
0.6197	Remote Similarity	NPC264589
0.6184	Remote Similarity	NPC225774
0.6182	Remote Similarity	NPC74936
0.6182	Remote Similarity	NPC159178
0.6182	Remote Similarity	NPC209764
0.6182	Remote Similarity	NPC141139
0.6182	Remote Similarity	NPC121872
0.6182	Remote Similarity	NPC471307
0.6182	Remote Similarity	NPC78041
0.6181	Remote Similarity	NPC130941
0.6179	Remote Similarity	NPC296163
0.6174	Remote Similarity	NPC323726
0.617	Remote Similarity	NPC71009
0.617	Remote Similarity	NPC22786
0.6159	Remote Similarity	NPC314102
0.6159	Remote Similarity	NPC251722
0.6149	Remote Similarity	NPC76079
0.6149	Remote Similarity	NPC123323
0.6147	Remote Similarity	NPC30445
0.6144	Remote Similarity	NPC219341
0.6144	Remote Similarity	NPC476432
0.6144	Remote Similarity	NPC24264
0.614	Remote Similarity	NPC311242
0.6118	Remote Similarity	NPC324144
0.6115	Remote Similarity	NPC130251
0.6111	Remote Similarity	NPC109787
0.6107	Remote Similarity	NPC56765
0.6107	Remote Similarity	NPC6436
0.6105	Remote Similarity	NPC45756
0.6104	Remote Similarity	NPC205421
0.6104	Remote Similarity	NPC474931
0.6104	Remote Similarity	NPC145832
0.6104	Remote Similarity	NPC81218
0.6104	Remote Similarity	NPC306555
0.6104	Remote Similarity	NPC117188
0.6104	Remote Similarity	NPC158376
0.6104	Remote Similarity	NPC12053
0.6104	Remote Similarity	NPC298979
0.6104	Remote Similarity	NPC247389
0.6094	Remote Similarity	NPC316582
0.6091	Remote Similarity	NPC298115
0.6078	Remote Similarity	NPC253043
0.6078	Remote Similarity	NPC167546
0.6078	Remote Similarity	NPC212794
0.6078	Remote Similarity	NPC13504
0.6078	Remote Similarity	NPC136508
0.6078	Remote Similarity	NPC78222
0.6078	Remote Similarity	NPC196447
0.6078	Remote Similarity	NPC477563
0.6078	Remote Similarity	NPC302527
0.6078	Remote Similarity	NPC16805
0.6078	Remote Similarity	NPC96603
0.6078	Remote Similarity	NPC306843
0.6071	Remote Similarity	NPC314682

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 NPC239854 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	978
0.2-0.3	986
0.3-0.4	2658
0.4-0.5	2805
0.5-0.6	1037
0.6-0.7	260
0.7-0.8	84
0.8-0.85	17
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD4408	Approved
0.8947	High Similarity	NPD4405	Approved
0.8947	High Similarity	NPD4407	Approved
0.8776	High Similarity	NPD5598	Approved
0.8776	High Similarity	NPD5597	Approved
0.8469	Intermediate Similarity	NPD4542	Approved
0.8469	Intermediate Similarity	NPD4545	Approved
0.8469	Intermediate Similarity	NPD6549	Approved
0.8469	Intermediate Similarity	NPD6548	Approved
0.8462	Intermediate Similarity	NPD7170	Discontinued
0.8454	Intermediate Similarity	NPD2997	Approved
0.8454	Intermediate Similarity	NPD3000	Approved
0.8454	Intermediate Similarity	NPD2998	Approved
0.83	Intermediate Similarity	NPD2005	Discontinued
0.8298	Intermediate Similarity	NPD2538	Approved
0.8298	Intermediate Similarity	NPD2539	Approved
0.8269	Intermediate Similarity	NPD4937	Approved
0.8269	Intermediate Similarity	NPD4936	Approved
0.8137	Intermediate Similarity	NPD6499	Approved
0.8137	Intermediate Similarity	NPD6498	Approved
0.8137	Intermediate Similarity	NPD5832	Phase 3
0.8125	Intermediate Similarity	NPD4406	Approved
0.8125	Intermediate Similarity	NPD4409	Approved
0.8061	Intermediate Similarity	NPD5656	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD1946	Clinical (unspecified phase)
0.802	Intermediate Similarity	NPD5554	Approved
0.7979	Intermediate Similarity	NPD4027	Approved
0.7979	Intermediate Similarity	NPD4026	Approved
0.7963	Intermediate Similarity	NPD8009	Approved
0.7963	Intermediate Similarity	NPD8010	Approved
0.7959	Intermediate Similarity	NPD3345	Approved
0.7941	Intermediate Similarity	NPD6472	Discontinued
0.7938	Intermediate Similarity	NPD5252	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD4636	Approved
0.7917	Intermediate Similarity	NPD4544	Approved
0.7895	Intermediate Similarity	NPD4170	Approved
0.7895	Intermediate Similarity	NPD4701	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4169	Approved
0.789	Intermediate Similarity	NPD6236	Approved
0.789	Intermediate Similarity	NPD6235	Approved
0.781	Intermediate Similarity	NPD1916	Discontinued
0.7789	Intermediate Similarity	NPD3035	Approved
0.7748	Intermediate Similarity	NPD2038	Approved
0.7748	Intermediate Similarity	NPD2039	Approved
0.7745	Intermediate Similarity	NPD2878	Approved
0.7732	Intermediate Similarity	NPD5178	Approved
0.7684	Intermediate Similarity	NPD5372	Approved
0.7684	Intermediate Similarity	NPD5371	Approved
0.7653	Intermediate Similarity	NPD5916	Discontinued
0.7629	Intermediate Similarity	NPD4635	Approved
0.7624	Intermediate Similarity	NPD3346	Approved
0.7624	Intermediate Similarity	NPD5915	Approved
0.7624	Intermediate Similarity	NPD3344	Approved
0.7611	Intermediate Similarity	NPD7059	Approved
0.7611	Intermediate Similarity	NPD2913	Approved
0.7611	Intermediate Similarity	NPD7060	Approved
0.7611	Intermediate Similarity	NPD2914	Approved
0.7596	Intermediate Similarity	NPD2895	Discontinued
0.7593	Intermediate Similarity	NPD2939	Approved
0.7593	Intermediate Similarity	NPD2937	Phase 1
0.7576	Intermediate Similarity	NPD3099	Discontinued
0.7573	Intermediate Similarity	NPD3980	Approved
0.7573	Intermediate Similarity	NPD3982	Approved
0.7553	Intermediate Similarity	NPD4144	Approved
0.7553	Intermediate Similarity	NPD603	Approved
0.7553	Intermediate Similarity	NPD4147	Approved
0.75	Intermediate Similarity	NPD3904	Approved
0.75	Intermediate Similarity	NPD3979	Approved
0.75	Intermediate Similarity	NPD5103	Approved
0.75	Intermediate Similarity	NPD3903	Approved
0.75	Intermediate Similarity	NPD3981	Approved
0.7436	Intermediate Similarity	NPD5511	Discontinued
0.7429	Intermediate Similarity	NPD5964	Phase 2
0.7429	Intermediate Similarity	NPD5963	Phase 2
0.7411	Intermediate Similarity	NPD7633	Discontinued
0.7411	Intermediate Similarity	NPD4116	Approved
0.7377	Intermediate Similarity	NPD5838	Phase 2
0.7373	Intermediate Similarity	NPD5516	Phase 2
0.7373	Intermediate Similarity	NPD5517	Phase 2
0.7327	Intermediate Similarity	NPD4145	Approved
0.7327	Intermediate Similarity	NPD4146	Approved
0.7321	Intermediate Similarity	NPD1721	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2396	Approved
0.7288	Intermediate Similarity	NPD2395	Approved
0.7258	Intermediate Similarity	NPD7582	Discontinued
0.7255	Intermediate Similarity	NPD5675	Discontinued
0.7248	Intermediate Similarity	NPD4734	Approved
0.7248	Intermediate Similarity	NPD4735	Approved
0.7241	Intermediate Similarity	NPD5629	Discontinued
0.7238	Intermediate Similarity	NPD8	Approved
0.7238	Intermediate Similarity	NPD243	Approved
0.7232	Intermediate Similarity	NPD5253	Approved
0.7216	Intermediate Similarity	NPD1053	Approved
0.7216	Intermediate Similarity	NPD1052	Approved
0.7216	Intermediate Similarity	NPD1051	Approved
0.7216	Intermediate Similarity	NPD508	Approved
0.7216	Intermediate Similarity	NPD507	Approved
0.7213	Intermediate Similarity	NPD7464	Phase 3
0.7213	Intermediate Similarity	NPD6025	Phase 1
0.7212	Intermediate Similarity	NPD4543	Discontinued
0.7203	Intermediate Similarity	NPD5130	Phase 3
0.7167	Intermediate Similarity	NPD4416	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD3428	Approved
0.7157	Intermediate Similarity	NPD3426	Approved
0.7129	Intermediate Similarity	NPD9505	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7679	Phase 2
0.7094	Intermediate Similarity	NPD3551	Approved
0.7094	Intermediate Similarity	NPD2508	Discontinued
0.7091	Intermediate Similarity	NPD5753	Discontinued
0.7091	Intermediate Similarity	NPD6027	Approved
0.7091	Intermediate Similarity	NPD6024	Approved
0.7064	Intermediate Similarity	NPD4008	Approved
0.7064	Intermediate Similarity	NPD4007	Approved
0.7054	Intermediate Similarity	NPD959	Discontinued
0.703	Intermediate Similarity	NPD3427	Approved
0.703	Intermediate Similarity	NPD3429	Approved
0.7009	Intermediate Similarity	NPD6562	Approved
0.7009	Intermediate Similarity	NPD6561	Approved
0.6992	Remote Similarity	NPD7461	Approved
0.6991	Remote Similarity	NPD3545	Approved
0.6991	Remote Similarity	NPD3546	Approved
0.699	Remote Similarity	NPD780	Approved
0.699	Remote Similarity	NPD783	Approved
0.699	Remote Similarity	NPD782	Approved
0.699	Remote Similarity	NPD781	Approved
0.6967	Remote Similarity	NPD5576	Approved
0.6967	Remote Similarity	NPD5579	Approved
0.6961	Remote Similarity	NPD2208	Approved
0.6961	Remote Similarity	NPD2205	Approved
0.6949	Remote Similarity	NPD5631	Phase 3
0.6944	Remote Similarity	NPD1738	Approved
0.6935	Remote Similarity	NPD3549	Approved
0.6935	Remote Similarity	NPD3547	Approved
0.6935	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4114	Approved
0.693	Remote Similarity	NPD4115	Approved
0.6916	Remote Similarity	NPD736	Approved
0.6916	Remote Similarity	NPD735	Approved
0.6885	Remote Similarity	NPD6806	Phase 1
0.6885	Remote Similarity	NPD5961	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5836	Discontinued
0.6881	Remote Similarity	NPD713	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5156	Approved
0.6875	Remote Similarity	NPD5155	Approved
0.687	Remote Similarity	NPD8125	Discontinued
0.6864	Remote Similarity	NPD5180	Approved
0.6864	Remote Similarity	NPD5181	Approved
0.6864	Remote Similarity	NPD5179	Approved
0.6861	Remote Similarity	NPD2420	Approved
0.6861	Remote Similarity	NPD2421	Approved
0.6842	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1935	Phase 3
0.6827	Remote Similarity	NPD2002	Discontinued
0.6797	Remote Similarity	NPD2605	Approved
0.6797	Remote Similarity	NPD3595	Approved
0.6797	Remote Similarity	NPD2606	Approved
0.6797	Remote Similarity	NPD3594	Approved
0.6789	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6299	Approved
0.6783	Remote Similarity	NPD6300	Approved
0.6769	Remote Similarity	NPD7578	Phase 2
0.6768	Remote Similarity	NPD295	Approved
0.6768	Remote Similarity	NPD293	Approved
0.6768	Remote Similarity	NPD296	Approved
0.6765	Remote Similarity	NPD830	Approved
0.6765	Remote Similarity	NPD831	Approved
0.6765	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD588	Approved
0.6762	Remote Similarity	NPD587	Approved
0.6729	Remote Similarity	NPD7160	Approved
0.6727	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4657	Approved
0.6727	Remote Similarity	NPD4655	Approved
0.6726	Remote Similarity	NPD5655	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD2242	Phase 1
0.6723	Remote Similarity	NPD2659	Approved
0.6723	Remote Similarity	NPD3148	Approved
0.6723	Remote Similarity	NPD3149	Approved
0.6723	Remote Similarity	NPD3147	Approved
0.6723	Remote Similarity	NPD2658	Approved
0.6723	Remote Similarity	NPD3150	Approved
0.6721	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD3635	Approved
0.6719	Remote Similarity	NPD3636	Approved
0.6719	Remote Similarity	NPD3637	Approved
0.67	Remote Similarity	NPD589	Approved
0.67	Remote Similarity	NPD590	Approved
0.6699	Remote Similarity	NPD785	Approved
0.6695	Remote Similarity	NPD3001	Approved
0.6695	Remote Similarity	NPD2999	Approved
0.6694	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1302	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4263	Approved
0.6667	Remote Similarity	NPD4813	Approved
0.6667	Remote Similarity	NPD1922	Discontinued
0.6667	Remote Similarity	NPD7062	Discontinued
0.6639	Remote Similarity	NPD1762	Approved
0.6639	Remote Similarity	NPD1764	Approved
0.6637	Remote Similarity	NPD5716	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