NPASS Compound

Structure

CID326316 OpenBabel06191716192D 22 25 0 0 1 0 0 0 0 0999 V2000 1.6911 -3.8415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0165 1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4277 -0.2697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4994 -2.4494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5172 -1.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6510 -2.9187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6866 -0.9799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5043 -1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5085 -2.3937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0068 -2.8953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6595 0.0100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8203 -2.4186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6665 -0.9525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 -1.4492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8393 -2.4090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8276 0.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8389 -1.4360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0056 -0.9628 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 1.6809 -2.8772 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8175 1.4407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8299 0.4795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 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 10 15 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 17 1 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	295.16
Volume:	315.713
LogP:	3.155
LogD:	3.02
LogS:	-2.491
# Rotatable Bonds:	2
TPSA:	21.7
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.847
Synthetic Accessibility Score:	2.799
Fsp3:	0.368
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:	-4.539
MDCK Permeability:	2.4404411306022666e-05
Pgp-inhibitor:	0.821
Pgp-substrate:	0.932
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.259

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	85.2606430053711%
Volume Distribution (VD):	2.059
Pgp-substrate:	6.642257213592529%

ADMET: Metabolism

CYP1A2-inhibitor:	0.613
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.962
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.668
CYP2D6-inhibitor:	0.724
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.074
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	7.804
Half-life (T1/2):	0.268

ADMET: Toxicity

hERG Blockers:	0.73
Human Hepatotoxicity (H-HT):	0.192
Drug-inuced Liver Injury (DILI):	0.176
AMES Toxicity:	0.557
Rat Oral Acute Toxicity:	0.816
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.215
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC326316

Natural Product ID:	NPC326316
*Common Name:**	(+/-)-Nuciferine
IUPAC Name:	1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
Synonyms:
Standard InCHIKey:	ORJVQPIHKOARKV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H21NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3
SMILES:	CN1CCC2=CC(=C(C3=C2C1CC4=CC=CC=C43)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2414990
PubChem CID:	3108374
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
Ki	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1858	Individual Protein	Dopamine D2 receptor	Rattus norvegicus	Ki	=	173.38	nM	PMID[464242]
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	Ki	=	587.49	nM	PMID[464242]
NPT1858	Individual Protein	Dopamine D2 receptor	Rattus norvegicus	Ki	=	209.0	nM	PMID[464242]
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	Ki	=	630.0	nM	PMID[464242]

☑ 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 NPC326316 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	360
0.1-0.2	1962
0.2-0.3	10464
0.3-0.4	7281
0.4-0.5	7490
0.5-0.6	11451
0.6-0.7	2794
0.7-0.8	524
0.8-0.85	182
0.85-0.9	119
0.9-0.95	56
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC81733
0.966	High Similarity	NPC476572
0.9658	High Similarity	NPC325871
0.9658	High Similarity	NPC99659
0.9592	High Similarity	NPC126519
0.9592	High Similarity	NPC170503
0.9592	High Similarity	NPC203784
0.953	High Similarity	NPC27410
0.953	High Similarity	NPC477559
0.953	High Similarity	NPC160298
0.953	High Similarity	NPC166014
0.953	High Similarity	NPC306902
0.953	High Similarity	NPC266753
0.953	High Similarity	NPC232924
0.9342	High Similarity	NPC225774
0.9296	High Similarity	NPC470925
0.9281	High Similarity	NPC24264
0.9281	High Similarity	NPC219341
0.9281	High Similarity	NPC476432
0.9276	High Similarity	NPC324144
0.9225	High Similarity	NPC314682
0.9221	High Similarity	NPC158376
0.9221	High Similarity	NPC12053
0.9221	High Similarity	NPC117188
0.9221	High Similarity	NPC306555
0.9221	High Similarity	NPC205421
0.9221	High Similarity	NPC145832
0.9221	High Similarity	NPC247389
0.9221	High Similarity	NPC474931
0.9221	High Similarity	NPC298979
0.9221	High Similarity	NPC81218
0.9216	High Similarity	NPC477563
0.9216	High Similarity	NPC13504
0.9216	High Similarity	NPC306843
0.9216	High Similarity	NPC167546
0.9216	High Similarity	NPC253043
0.9216	High Similarity	NPC196447
0.9216	High Similarity	NPC78222
0.9216	High Similarity	NPC16805
0.9216	High Similarity	NPC302527
0.9216	High Similarity	NPC136508
0.9216	High Similarity	NPC212794
0.9216	High Similarity	NPC96603
0.9184	High Similarity	NPC219162
0.9184	High Similarity	NPC92541
0.9178	High Similarity	NPC210437
0.9178	High Similarity	NPC106295
0.9178	High Similarity	NPC16107
0.9178	High Similarity	NPC476144
0.9178	High Similarity	NPC51957
0.9161	High Similarity	NPC213206
0.9161	High Similarity	NPC328750
0.9161	High Similarity	NPC474915
0.9161	High Similarity	NPC188163
0.9161	High Similarity	NPC241055
0.9156	High Similarity	NPC35627
0.9156	High Similarity	NPC476573
0.9156	High Similarity	NPC86144
0.9156	High Similarity	NPC81247
0.9156	High Similarity	NPC304659
0.915	High Similarity	NPC1229
0.9128	High Similarity	NPC470924
0.9116	High Similarity	NPC7467
0.9097	High Similarity	NPC210918
0.9091	High Similarity	NPC168409
0.9048	High Similarity	NPC253883
0.9048	High Similarity	NPC90844
0.9048	High Similarity	NPC144863
0.9048	High Similarity	NPC95075
0.9034	High Similarity	NPC136860
0.9034	High Similarity	NPC128019
0.9034	High Similarity	NPC476567
0.9026	High Similarity	NPC189470
0.9007	High Similarity	NPC244112
0.8986	High Similarity	NPC130941
0.8981	High Similarity	NPC118274
0.8981	High Similarity	NPC168753
0.8974	High Similarity	NPC204947
0.8924	High Similarity	NPC149090
0.8924	High Similarity	NPC19520
0.8924	High Similarity	NPC239775
0.8919	High Similarity	NPC476151
0.8912	High Similarity	NPC185838
0.8868	High Similarity	NPC192135
0.8868	High Similarity	NPC66341
0.8868	High Similarity	NPC477020
0.8868	High Similarity	NPC285941
0.8861	High Similarity	NPC69712
0.8861	High Similarity	NPC26240
0.8861	High Similarity	NPC477562
0.8861	High Similarity	NPC6152
0.882	High Similarity	NPC114364
0.882	High Similarity	NPC320223
0.8812	High Similarity	NPC199465
0.8812	High Similarity	NPC229166
0.8812	High Similarity	NPC128560
0.88	High Similarity	NPC103379
0.88	High Similarity	NPC477565
0.8792	High Similarity	NPC179825
0.8792	High Similarity	NPC321505
0.8792	High Similarity	NPC191376
0.8765	High Similarity	NPC220961
0.8765	High Similarity	NPC126284
0.8758	High Similarity	NPC249797
0.8758	High Similarity	NPC193949
0.8758	High Similarity	NPC184026
0.8758	High Similarity	NPC207757
0.8758	High Similarity	NPC278799
0.8758	High Similarity	NPC172765
0.8758	High Similarity	NPC41178
0.8758	High Similarity	NPC127674
0.8758	High Similarity	NPC54379
0.8758	High Similarity	NPC5238
0.8758	High Similarity	NPC138487
0.8758	High Similarity	NPC216459
0.8758	High Similarity	NPC189266
0.8758	High Similarity	NPC110416
0.8758	High Similarity	NPC2413
0.8758	High Similarity	NPC39701
0.8758	High Similarity	NPC276588
0.8758	High Similarity	NPC204828
0.8758	High Similarity	NPC295691
0.8758	High Similarity	NPC469817
0.875	High Similarity	NPC26601
0.8742	High Similarity	NPC152212
0.8733	High Similarity	NPC475959
0.8733	High Similarity	NPC24233
0.8733	High Similarity	NPC476571
0.8733	High Similarity	NPC135538
0.8733	High Similarity	NPC147390
0.8733	High Similarity	NPC246587
0.8733	High Similarity	NPC428
0.8718	High Similarity	NPC60186
0.8701	High Similarity	NPC146288
0.8662	High Similarity	NPC233650
0.8659	High Similarity	NPC248642
0.865	High Similarity	NPC474507
0.865	High Similarity	NPC267408
0.8642	High Similarity	NPC148709
0.8642	High Similarity	NPC112575
0.8642	High Similarity	NPC476577
0.8642	High Similarity	NPC173416
0.8636	High Similarity	NPC76079
0.8618	High Similarity	NPC151895
0.8618	High Similarity	NPC192768
0.8618	High Similarity	NPC88249
0.8618	High Similarity	NPC97221
0.8618	High Similarity	NPC220858
0.8608	High Similarity	NPC134858
0.8606	High Similarity	NPC302275
0.8606	High Similarity	NPC156576
0.8598	High Similarity	NPC474506
0.8598	High Similarity	NPC32413
0.8592	High Similarity	NPC160193
0.859	High Similarity	NPC477080
0.8589	High Similarity	NPC23219
0.8589	High Similarity	NPC190461
0.8581	High Similarity	NPC247639
0.8581	High Similarity	NPC323443
0.8581	High Similarity	NPC25084
0.8581	High Similarity	NPC186063
0.8581	High Similarity	NPC180756
0.8581	High Similarity	NPC31311
0.8581	High Similarity	NPC234392
0.858	High Similarity	NPC477558
0.8562	High Similarity	NPC476568
0.8553	High Similarity	NPC207824
0.8553	High Similarity	NPC60538
0.8545	High Similarity	NPC116284
0.8537	High Similarity	NPC470879
0.8537	High Similarity	NPC258695
0.8533	High Similarity	NPC130926
0.8516	High Similarity	NPC123323
0.8506	High Similarity	NPC210148
0.8506	High Similarity	NPC233029
0.85	High Similarity	NPC210140
0.85	High Similarity	NPC150879
0.8494	Intermediate Similarity	NPC276674
0.8494	Intermediate Similarity	NPC33902
0.8494	Intermediate Similarity	NPC135772
0.8485	Intermediate Similarity	NPC476574
0.8485	Intermediate Similarity	NPC312918
0.8485	Intermediate Similarity	NPC155442
0.8485	Intermediate Similarity	NPC477561
0.8485	Intermediate Similarity	NPC179704
0.8476	Intermediate Similarity	NPC148693
0.8476	Intermediate Similarity	NPC118633
0.8476	Intermediate Similarity	NPC294790
0.8471	Intermediate Similarity	NPC118804
0.8452	Intermediate Similarity	NPC477564
0.8452	Intermediate Similarity	NPC237579
0.8452	Intermediate Similarity	NPC2295
0.8451	Intermediate Similarity	NPC172403
0.8442	Intermediate Similarity	NPC76213
0.8442	Intermediate Similarity	NPC277669
0.8435	Intermediate Similarity	NPC253429
0.8434	Intermediate Similarity	NPC249405
0.8415	Intermediate Similarity	NPC287588
0.8414	Intermediate Similarity	NPC325568
0.8411	Intermediate Similarity	NPC145304

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 NPC326316 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	854
0.2-0.3	1024
0.3-0.4	1821
0.4-0.5	2636
0.5-0.6	1774
0.6-0.7	606
0.7-0.8	173
0.8-0.85	29
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9178	High Similarity	NPD4584	Approved
0.9161	High Similarity	NPD4664	Clinical (unspecified phase)
0.8725	High Similarity	NPD2420	Approved
0.8725	High Similarity	NPD2421	Approved
0.8562	High Similarity	NPD4017	Approved
0.8438	Intermediate Similarity	NPD3051	Approved
0.8428	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD3110	Approved
0.8414	Intermediate Similarity	NPD3109	Approved
0.8397	Intermediate Similarity	NPD7298	Approved
0.8344	Intermediate Similarity	NPD5241	Discontinued
0.8312	Intermediate Similarity	NPD3639	Approved
0.8312	Intermediate Similarity	NPD3641	Approved
0.8312	Intermediate Similarity	NPD3640	Phase 3
0.8311	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD2970	Approved
0.8272	Intermediate Similarity	NPD2969	Approved
0.8239	Intermediate Similarity	NPD6788	Approved
0.8232	Intermediate Similarity	NPD8252	Approved
0.8232	Intermediate Similarity	NPD8251	Approved
0.8232	Intermediate Similarity	NPD8099	Discontinued
0.8221	Intermediate Similarity	NPD27	Approved
0.8221	Intermediate Similarity	NPD2489	Approved
0.8221	Intermediate Similarity	NPD4481	Phase 3
0.8194	Intermediate Similarity	NPD6031	Approved
0.8194	Intermediate Similarity	NPD6030	Approved
0.8182	Intermediate Similarity	NPD8156	Discontinued
0.8151	Intermediate Similarity	NPD5718	Phase 2
0.811	Intermediate Similarity	NPD2898	Approved
0.8105	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD4773	Phase 2
0.8101	Intermediate Similarity	NPD4772	Phase 2
0.8082	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7833	Phase 2
0.8075	Intermediate Similarity	NPD7831	Phase 2
0.8	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD4474	Approved
0.7973	Intermediate Similarity	NPD4475	Approved
0.7941	Intermediate Similarity	NPD2968	Approved
0.7941	Intermediate Similarity	NPD2971	Approved
0.7935	Intermediate Similarity	NPD3845	Phase 1
0.7935	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7802	Discontinued
0.7895	Intermediate Similarity	NPD8053	Approved
0.7895	Intermediate Similarity	NPD8054	Approved
0.7891	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD3124	Discontinued
0.7879	Intermediate Similarity	NPD4010	Discontinued
0.7861	Intermediate Similarity	NPD7906	Approved
0.7844	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD4577	Approved
0.7836	Intermediate Similarity	NPD4578	Approved
0.7821	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD5754	Discontinued
0.7791	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7598	Phase 2
0.7763	Intermediate Similarity	NPD6895	Approved
0.7763	Intermediate Similarity	NPD6896	Approved
0.775	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7310	Approved
0.7733	Intermediate Similarity	NPD7311	Approved
0.7733	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7313	Approved
0.7733	Intermediate Similarity	NPD7312	Approved
0.7722	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6107	Approved
0.7701	Intermediate Similarity	NPD4663	Approved
0.7692	Intermediate Similarity	NPD6748	Discontinued
0.7688	Intermediate Similarity	NPD7309	Approved
0.7673	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD2488	Approved
0.767	Intermediate Similarity	NPD2490	Approved
0.7667	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD4166	Phase 2
0.7665	Intermediate Similarity	NPD6071	Discontinued
0.7628	Intermediate Similarity	NPD5177	Phase 3
0.7625	Intermediate Similarity	NPD4727	Phase 1
0.7622	Intermediate Similarity	NPD2563	Approved
0.7622	Intermediate Similarity	NPD2560	Approved
0.7622	Intermediate Similarity	NPD5978	Approved
0.7622	Intermediate Similarity	NPD5977	Approved
0.761	Intermediate Similarity	NPD1424	Approved
0.76	Intermediate Similarity	NPD5156	Approved
0.76	Intermediate Similarity	NPD5155	Approved
0.759	Intermediate Similarity	NPD7400	Phase 3
0.7558	Intermediate Similarity	NPD6297	Approved
0.7533	Intermediate Similarity	NPD3594	Approved
0.7533	Intermediate Similarity	NPD2606	Approved
0.7533	Intermediate Similarity	NPD2605	Approved
0.7533	Intermediate Similarity	NPD3595	Approved
0.7532	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4055	Discovery
0.7515	Intermediate Similarity	NPD6688	Approved
0.7515	Intermediate Similarity	NPD6687	Approved
0.75	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1753	Discontinued
0.7471	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3636	Approved
0.7467	Intermediate Similarity	NPD3637	Approved
0.7467	Intermediate Similarity	NPD3635	Approved
0.7459	Intermediate Similarity	NPD2974	Approved
0.7459	Intermediate Similarity	NPD2973	Approved
0.7459	Intermediate Similarity	NPD2975	Approved
0.7458	Intermediate Similarity	NPD7291	Discontinued
0.7452	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5312	Approved
0.7442	Intermediate Similarity	NPD5313	Approved
0.744	Intermediate Similarity	NPD6037	Discontinued
0.7439	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7110	Phase 1
0.7432	Intermediate Similarity	NPD1669	Approved
0.7421	Intermediate Similarity	NPD5160	Discontinued
0.7407	Intermediate Similarity	NPD1914	Approved
0.7407	Intermediate Similarity	NPD5976	Discontinued
0.7386	Intermediate Similarity	NPD6851	Approved
0.7386	Intermediate Similarity	NPD6853	Approved
0.7377	Intermediate Similarity	NPD8095	Phase 1
0.7375	Intermediate Similarity	NPD7124	Phase 2
0.7358	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6090	Discontinued
0.7337	Intermediate Similarity	NPD4580	Approved
0.7326	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7294	Phase 1
0.7301	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3920	Phase 2
0.7297	Intermediate Similarity	NPD3452	Approved
0.7297	Intermediate Similarity	NPD2494	Approved
0.7297	Intermediate Similarity	NPD3450	Approved
0.7297	Intermediate Similarity	NPD2493	Approved
0.7289	Intermediate Similarity	NPD5720	Discontinued
0.7285	Intermediate Similarity	NPD7905	Discontinued
0.7278	Intermediate Similarity	NPD4726	Approved
0.7278	Intermediate Similarity	NPD4725	Approved
0.7278	Intermediate Similarity	NPD4721	Approved
0.7273	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2674	Phase 3
0.7257	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6747	Phase 1
0.725	Intermediate Similarity	NPD6331	Phase 2
0.7233	Intermediate Similarity	NPD4257	Approved
0.7233	Intermediate Similarity	NPD4256	Phase 2
0.7228	Intermediate Similarity	NPD4420	Approved
0.7219	Intermediate Similarity	NPD4098	Discontinued
0.7205	Intermediate Similarity	NPD3301	Approved
0.7205	Intermediate Similarity	NPD3692	Discontinued
0.72	Intermediate Similarity	NPD7479	Phase 2
0.7198	Intermediate Similarity	NPD7262	Phase 1
0.7197	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7427	Discontinued
0.7191	Intermediate Similarity	NPD6618	Phase 2
0.7188	Intermediate Similarity	NPD3060	Approved
0.7188	Intermediate Similarity	NPD4162	Approved
0.7181	Intermediate Similarity	NPD4583	Approved
0.7181	Intermediate Similarity	NPD4582	Approved
0.7174	Intermediate Similarity	NPD7034	Discontinued
0.7169	Intermediate Similarity	NPD6875	Approved
0.7169	Intermediate Similarity	NPD6876	Approved
0.7162	Intermediate Similarity	NPD2668	Approved
0.7162	Intermediate Similarity	NPD2667	Approved
0.7153	Intermediate Similarity	NPD5283	Phase 1
0.7151	Intermediate Similarity	NPD4107	Approved
0.7151	Intermediate Similarity	NPD6612	Phase 2
0.7143	Intermediate Similarity	NPD1024	Discontinued
0.7143	Intermediate Similarity	NPD3924	Approved
0.7143	Intermediate Similarity	NPD3922	Approved
0.7143	Intermediate Similarity	NPD42	Phase 2
0.7143	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3921	Approved
0.7143	Intermediate Similarity	NPD3923	Approved
0.7143	Intermediate Similarity	NPD6042	Phase 2
0.7135	Intermediate Similarity	NPD5677	Discontinued
0.7133	Intermediate Similarity	NPD2232	Approved
0.7133	Intermediate Similarity	NPD2233	Approved
0.7133	Intermediate Similarity	NPD2230	Approved
0.7128	Intermediate Similarity	NPD4004	Approved
0.7128	Intermediate Similarity	NPD4002	Approved
0.7126	Intermediate Similarity	NPD5938	Phase 3
0.7125	Intermediate Similarity	NPD7037	Approved
0.7108	Intermediate Similarity	NPD4005	Discontinued
0.7097	Intermediate Similarity	NPD3144	Approved
0.7097	Intermediate Similarity	NPD3145	Approved
0.7095	Intermediate Similarity	NPD3443	Approved
0.7095	Intermediate Similarity	NPD3445	Approved
0.7095	Intermediate Similarity	NPD3444	Approved
0.7095	Intermediate Similarity	NPD4093	Discontinued
0.709	Intermediate Similarity	NPD4040	Phase 1
0.7088	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6025	Phase 1
0.7086	Intermediate Similarity	NPD1421	Approved
0.7086	Intermediate Similarity	NPD1420	Approved
0.7083	Intermediate Similarity	NPD7945	Clinical (unspecified phase)

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