NPASS Compound

Structure

NPC6152 OpenBabel07101718252D 24 28 0 0 1 0 0 0 0 0999 V2000 -1.3523 4.0404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3179 2.2748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3776 0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7407 2.0456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3517 1.3767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.2769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9886 0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1038 2.4799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4093 2.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1785 3.4771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5831 2.7087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 1 0 0 0 0 3 10 1 0 0 0 0 4 20 1 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 12 18 1 0 0 0 0 13 5 1 6 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.13
Volume:	324.737
LogP:	2.678
LogD:	2.572
LogS:	-3.076
# Rotatable Bonds:	2
TPSA:	48.95
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.92
Synthetic Accessibility Score:	3.18
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:	-5.246
MDCK Permeability:	1.6798767319414765e-05
Pgp-inhibitor:	0.12
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.919
Plasma Protein Binding (PPB):	86.79938507080078%
Volume Distribution (VD):	2.44
Pgp-substrate:	4.265002727508545%

ADMET: Metabolism

CYP1A2-inhibitor:	0.735
CYP1A2-substrate:	0.716
CYP2C19-inhibitor:	0.372
CYP2C19-substrate:	0.856
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.669
CYP2D6-inhibitor:	0.803
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.62
CYP3A4-substrate:	0.869

ADMET: Excretion

Clearance (CL):	7.281
Half-life (T1/2):	0.247

ADMET: Toxicity

hERG Blockers:	0.378
Human Hepatotoxicity (H-HT):	0.403
Drug-inuced Liver Injury (DILI):	0.501
AMES Toxicity:	0.613
Rat Oral Acute Toxicity:	0.602
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.146
Carcinogencity:	0.234
Eye Corrosion:	0.003
Eye Irritation:	0.009
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: NPC6152

Natural Product ID:	NPC6152
*Common Name:**	YNWJEUJZYKLCJG-CYBMUJFWSA-N
IUPAC Name:	n.a.
Synonyms:	(-)-Nordicentrine
Standard InCHIKey:	YNWJEUJZYKLCJG-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C19H19NO4/c1-21-14-7-11-5-13-17-10(3-4-20-13)6-16-19(24-9-23-16)18(17)12(11)8-15(14)22-2/h6-8,13,20H,3-5,9H2,1-2H3/t13-/m1/s1
SMILES:	COc1cc2c(cc1OC)C[C@@H]1c3c2c2OCOc2cc3CCN1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518744
PubChem CID:	10336429
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
NPO22151	Stephania pierrei	Species	Menispermaceae	Eukaryota	tubers	n.a.	n.a.	PMID[8254346]
NPO22151	Stephania pierrei	Species	Menispermaceae	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
ED50	14
MIC	1
Others	2

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	5
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	1.7	ug ml-1	PMID[449631]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	3.3	ug ml-1	PMID[449631]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.8	ug ml-1	PMID[449631]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.6	ug ml-1	PMID[449631]
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	0.8	ug ml-1	PMID[449631]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	1.5	ug ml-1	PMID[449631]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	1.7	ug ml-1	PMID[449631]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.0	ug ml-1	PMID[449631]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	13.2	ug ml-1	PMID[449631]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.7	ug ml-1	PMID[449631]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.7	ug ml-1	PMID[449631]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.6	ug ml-1	PMID[449631]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	470.0	ng/ml	PMID[449631]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	1030.0	ng/ml	PMID[449631]
NPT2	Others	Unspecified		Ratio ED50	=	2.0	n.a.	PMID[449631]
NPT2	Others	Unspecified		Ratio ED50	=	1.0	n.a.	PMID[449631]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	12.5	ug.mL-1	PMID[449632]

☑ 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 NPC6152 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	395
0.1-0.2	1988
0.2-0.3	9254
0.3-0.4	8776
0.4-0.5	7635
0.5-0.6	11470
0.6-0.7	2380
0.7-0.8	555
0.8-0.85	129
0.85-0.9	62
0.9-0.95	40
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9682	High Similarity	NPC304659
0.9682	High Similarity	NPC86144
0.963	High Similarity	NPC470879
0.963	High Similarity	NPC258695
0.9618	High Similarity	NPC167546
0.9618	High Similarity	NPC16805
0.9618	High Similarity	NPC302527
0.9571	High Similarity	NPC155442
0.9571	High Similarity	NPC312918
0.9571	High Similarity	NPC476574
0.9571	High Similarity	NPC32413
0.9571	High Similarity	NPC477561
0.9571	High Similarity	NPC474506
0.9568	High Similarity	NPC23219
0.9557	High Similarity	NPC476432
0.9557	High Similarity	NPC24264
0.9554	High Similarity	NPC189470
0.9509	High Similarity	NPC267408
0.9506	High Similarity	NPC112575
0.9497	High Similarity	NPC210918
0.9497	High Similarity	NPC247389
0.9494	High Similarity	NPC225774
0.9455	High Similarity	NPC135772
0.9444	High Similarity	NPC477558
0.9434	High Similarity	NPC219341
0.9341	High Similarity	NPC57036
0.9321	High Similarity	NPC19520
0.9321	High Similarity	NPC149090
0.9304	High Similarity	NPC160298
0.9304	High Similarity	NPC306902
0.9304	High Similarity	NPC232924
0.9304	High Similarity	NPC477559
0.9304	High Similarity	NPC266753
0.9286	High Similarity	NPC186546
0.9286	High Similarity	NPC476576
0.9259	High Similarity	NPC152212
0.9255	High Similarity	NPC204947
0.9236	High Similarity	NPC203784
0.9236	High Similarity	NPC126519
0.9236	High Similarity	NPC170503
0.9207	High Similarity	NPC128560
0.9207	High Similarity	NPC199465
0.9207	High Similarity	NPC229166
0.9172	High Similarity	NPC99659
0.9172	High Similarity	NPC325871
0.9162	High Similarity	NPC476575
0.9141	High Similarity	NPC26240
0.9141	High Similarity	NPC69712
0.9141	High Similarity	NPC477562
0.9096	High Similarity	NPC114364
0.9096	High Similarity	NPC320223
0.9057	High Similarity	NPC476572
0.9048	High Similarity	NPC275132
0.903	High Similarity	NPC66341
0.903	High Similarity	NPC477020
0.903	High Similarity	NPC192135
0.9018	High Similarity	NPC298979
0.9012	High Similarity	NPC117717
0.8963	High Similarity	NPC241055
0.8953	High Similarity	NPC475754
0.8935	High Similarity	NPC116284
0.8935	High Similarity	NPC248642
0.8929	High Similarity	NPC126284
0.8896	High Similarity	NPC168409
0.8882	High Similarity	NPC156576
0.8861	High Similarity	NPC326316
0.8861	High Similarity	NPC81733
0.8841	High Similarity	NPC476573
0.8841	High Similarity	NPC35627
0.8841	High Similarity	NPC81247
0.8817	High Similarity	NPC474507
0.878	High Similarity	NPC212794
0.878	High Similarity	NPC96603
0.878	High Similarity	NPC196447
0.878	High Similarity	NPC136508
0.878	High Similarity	NPC477563
0.878	High Similarity	NPC13504
0.878	High Similarity	NPC306843
0.878	High Similarity	NPC253043
0.878	High Similarity	NPC78222
0.8757	High Similarity	NPC118633
0.8757	High Similarity	NPC294790
0.8757	High Similarity	NPC148693
0.8728	High Similarity	NPC237579
0.872	High Similarity	NPC324144
0.8698	High Similarity	NPC173416
0.8698	High Similarity	NPC148709
0.8698	High Similarity	NPC476577
0.8696	High Similarity	NPC244112
0.8696	High Similarity	NPC41178
0.8696	High Similarity	NPC216459
0.8696	High Similarity	NPC138487
0.8678	High Similarity	NPC82763
0.8675	High Similarity	NPC474931
0.8675	High Similarity	NPC12053
0.8675	High Similarity	NPC81218
0.8675	High Similarity	NPC145832
0.8675	High Similarity	NPC306555
0.8675	High Similarity	NPC117188
0.8675	High Similarity	NPC205421
0.8675	High Similarity	NPC158376
0.8671	High Similarity	NPC214116
0.8671	High Similarity	NPC475959
0.8642	High Similarity	NPC146288
0.8621	High Similarity	NPC312531
0.8571	High Similarity	NPC210148
0.8571	High Similarity	NPC233029
0.8537	High Similarity	NPC477080
0.8528	High Similarity	NPC234392
0.8528	High Similarity	NPC31311
0.8521	High Similarity	NPC239775
0.8516	High Similarity	NPC244606
0.8516	High Similarity	NPC156728
0.85	High Similarity	NPC211296
0.8494	Intermediate Similarity	NPC1229
0.8485	Intermediate Similarity	NPC27410
0.8485	Intermediate Similarity	NPC166014
0.8466	Intermediate Similarity	NPC281581
0.8466	Intermediate Similarity	NPC76079
0.8444	Intermediate Similarity	NPC212163
0.8439	Intermediate Similarity	NPC179704
0.8438	Intermediate Similarity	NPC130941
0.8432	Intermediate Similarity	NPC46990
0.8424	Intermediate Similarity	NPC7393
0.8385	Intermediate Similarity	NPC219162
0.8382	Intermediate Similarity	NPC220961
0.8372	Intermediate Similarity	NPC287588
0.8363	Intermediate Similarity	NPC2314
0.8354	Intermediate Similarity	NPC93593
0.8353	Intermediate Similarity	NPC118274
0.8353	Intermediate Similarity	NPC168753
0.8352	Intermediate Similarity	NPC295676
0.8333	Intermediate Similarity	NPC276944
0.8333	Intermediate Similarity	NPC232514
0.8333	Intermediate Similarity	NPC238530
0.8313	Intermediate Similarity	NPC111485
0.8286	Intermediate Similarity	NPC249405
0.8272	Intermediate Similarity	NPC60538
0.8272	Intermediate Similarity	NPC207824
0.8269	Intermediate Similarity	NPC253429
0.8261	Intermediate Similarity	NPC95075
0.8261	Intermediate Similarity	NPC51957
0.8261	Intermediate Similarity	NPC476144
0.8261	Intermediate Similarity	NPC253883
0.8261	Intermediate Similarity	NPC106295
0.8261	Intermediate Similarity	NPC16107
0.8261	Intermediate Similarity	NPC210437
0.8261	Intermediate Similarity	NPC90844
0.825	Intermediate Similarity	NPC145304
0.8242	Intermediate Similarity	NPC80129
0.8242	Intermediate Similarity	NPC187022
0.8239	Intermediate Similarity	NPC476567
0.8239	Intermediate Similarity	NPC128019
0.8239	Intermediate Similarity	NPC136860
0.8235	Intermediate Similarity	NPC150879
0.8235	Intermediate Similarity	NPC57812
0.8235	Intermediate Similarity	NPC474324
0.8232	Intermediate Similarity	NPC114124
0.8228	Intermediate Similarity	NPC213206
0.8228	Intermediate Similarity	NPC188163
0.8228	Intermediate Similarity	NPC470925
0.8228	Intermediate Similarity	NPC474915
0.8228	Intermediate Similarity	NPC328750
0.8218	Intermediate Similarity	NPC190461
0.8214	Intermediate Similarity	NPC60186
0.821	Intermediate Similarity	NPC7467
0.8208	Intermediate Similarity	NPC329969
0.8202	Intermediate Similarity	NPC474904
0.8198	Intermediate Similarity	NPC65403
0.8193	Intermediate Similarity	NPC323443
0.8193	Intermediate Similarity	NPC180756
0.8187	Intermediate Similarity	NPC475845
0.8182	Intermediate Similarity	NPC233718
0.8182	Intermediate Similarity	NPC477564
0.8182	Intermediate Similarity	NPC299990
0.8182	Intermediate Similarity	NPC73492
0.8182	Intermediate Similarity	NPC2295
0.8176	Intermediate Similarity	NPC56887
0.8176	Intermediate Similarity	NPC223077
0.8176	Intermediate Similarity	NPC193853
0.8171	Intermediate Similarity	NPC76213
0.8171	Intermediate Similarity	NPC277669
0.8166	Intermediate Similarity	NPC320104
0.8165	Intermediate Similarity	NPC314682
0.816	Intermediate Similarity	NPC92541
0.814	Intermediate Similarity	NPC311991
0.814	Intermediate Similarity	NPC474708
0.814	Intermediate Similarity	NPC75958
0.8136	Intermediate Similarity	NPC302275
0.8129	Intermediate Similarity	NPC181653
0.8129	Intermediate Similarity	NPC190332
0.8121	Intermediate Similarity	NPC470924
0.8118	Intermediate Similarity	NPC209377
0.8103	Intermediate Similarity	NPC187678
0.8098	Intermediate Similarity	NPC37144
0.8098	Intermediate Similarity	NPC59907
0.8089	Intermediate Similarity	NPC7018
0.8084	Intermediate Similarity	NPC186063
0.807	Intermediate Similarity	NPC195392
0.8068	Intermediate Similarity	NPC475479

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 NPC6152 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	788
0.2-0.3	1111
0.3-0.4	2148
0.4-0.5	2755
0.5-0.6	1506
0.6-0.7	512
0.7-0.8	110
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD4584	Approved
0.8242	Intermediate Similarity	NPD7298	Approved
0.8228	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD4481	Phase 3
0.807	Intermediate Similarity	NPD3051	Approved
0.8049	Intermediate Similarity	NPD6030	Approved
0.8049	Intermediate Similarity	NPD6031	Approved
0.8049	Intermediate Similarity	NPD4727	Phase 1
0.7963	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD2970	Approved
0.7919	Intermediate Similarity	NPD2969	Approved
0.7834	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8252	Approved
0.7784	Intermediate Similarity	NPD8099	Discontinued
0.7784	Intermediate Similarity	NPD8251	Approved
0.7771	Intermediate Similarity	NPD2489	Approved
0.7771	Intermediate Similarity	NPD27	Approved
0.7765	Intermediate Similarity	NPD2977	Approved
0.7765	Intermediate Similarity	NPD2978	Approved
0.7758	Intermediate Similarity	NPD2420	Approved
0.7758	Intermediate Similarity	NPD2421	Approved
0.774	Intermediate Similarity	NPD8156	Discontinued
0.7735	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5976	Discontinued
0.7697	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3845	Phase 1
0.7674	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6788	Approved
0.7667	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7906	Approved
0.7633	Intermediate Similarity	NPD4017	Approved
0.7624	Intermediate Similarity	NPD2968	Approved
0.7624	Intermediate Similarity	NPD2971	Approved
0.7605	Intermediate Similarity	NPD1424	Approved
0.76	Intermediate Similarity	NPD6107	Approved
0.7557	Intermediate Similarity	NPD4166	Phase 2
0.7543	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4578	Approved
0.7527	Intermediate Similarity	NPD7311	Approved
0.7527	Intermediate Similarity	NPD7310	Approved
0.7527	Intermediate Similarity	NPD7312	Approved
0.7527	Intermediate Similarity	NPD7313	Approved
0.7527	Intermediate Similarity	NPD4577	Approved
0.7526	Intermediate Similarity	NPD4859	Phase 1
0.7515	Intermediate Similarity	NPD3639	Approved
0.7515	Intermediate Similarity	NPD3640	Phase 3
0.7515	Intermediate Similarity	NPD3641	Approved
0.7513	Intermediate Similarity	NPD4420	Approved
0.75	Intermediate Similarity	NPD4663	Approved
0.7486	Intermediate Similarity	NPD8053	Approved
0.7486	Intermediate Similarity	NPD8054	Approved
0.7486	Intermediate Similarity	NPD7309	Approved
0.7462	Intermediate Similarity	NPD7827	Phase 1
0.7459	Intermediate Similarity	NPD6297	Approved
0.7457	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3110	Approved
0.7453	Intermediate Similarity	NPD3109	Approved
0.744	Intermediate Similarity	NPD7598	Phase 2
0.7425	Intermediate Similarity	NPD5241	Discontinued
0.7378	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD2898	Approved
0.736	Intermediate Similarity	NPD6071	Discontinued
0.7358	Intermediate Similarity	NPD5006	Approved
0.7358	Intermediate Similarity	NPD5005	Approved
0.7356	Intermediate Similarity	NPD4585	Approved
0.7341	Intermediate Similarity	NPD4772	Phase 2
0.7341	Intermediate Similarity	NPD4773	Phase 2
0.733	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7831	Phase 2
0.733	Intermediate Similarity	NPD7833	Phase 2
0.7314	Intermediate Similarity	NPD2563	Approved
0.7314	Intermediate Similarity	NPD2560	Approved
0.7305	Intermediate Similarity	NPD3060	Approved
0.7299	Intermediate Similarity	NPD3382	Approved
0.7299	Intermediate Similarity	NPD3384	Approved
0.7299	Intermediate Similarity	NPD3383	Approved
0.7297	Intermediate Similarity	NPD6853	Approved
0.7297	Intermediate Similarity	NPD6851	Approved
0.7287	Intermediate Similarity	NPD2490	Approved
0.7287	Intermediate Similarity	NPD2488	Approved
0.7277	Intermediate Similarity	NPD2974	Approved
0.7277	Intermediate Similarity	NPD2975	Approved
0.7277	Intermediate Similarity	NPD2973	Approved
0.7263	Intermediate Similarity	NPD4010	Discontinued
0.7262	Intermediate Similarity	NPD5754	Discontinued
0.7262	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4055	Discovery
0.7229	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5718	Phase 2
0.7219	Intermediate Similarity	NPD5160	Discontinued
0.7207	Intermediate Similarity	NPD7802	Discontinued
0.7191	Intermediate Similarity	NPD5709	Phase 3
0.7181	Intermediate Similarity	NPD3349	Phase 2
0.7165	Intermediate Similarity	NPD5457	Discontinued
0.7165	Intermediate Similarity	NPD4580	Approved
0.7158	Intermediate Similarity	NPD6042	Phase 2
0.7158	Intermediate Similarity	NPD42	Phase 2
0.7151	Intermediate Similarity	NPD4666	Phase 3
0.7143	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5604	Discontinued
0.7128	Intermediate Similarity	NPD3450	Approved
0.7128	Intermediate Similarity	NPD3452	Approved
0.7128	Intermediate Similarity	NPD2494	Approved
0.7128	Intermediate Similarity	NPD2493	Approved
0.7118	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4162	Approved
0.7095	Intermediate Similarity	NPD7400	Phase 3
0.7077	Intermediate Similarity	NPD6612	Phase 2
0.7077	Intermediate Similarity	NPD4107	Approved
0.7075	Intermediate Similarity	NPD6723	Discontinued
0.7073	Intermediate Similarity	NPD4475	Approved
0.7073	Intermediate Similarity	NPD3763	Approved
0.7073	Intermediate Similarity	NPD4474	Approved
0.7059	Intermediate Similarity	NPD7280	Phase 3
0.7059	Intermediate Similarity	NPD7281	Phase 3
0.7059	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6037	Discontinued
0.7053	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3124	Discontinued
0.7026	Intermediate Similarity	NPD8095	Phase 1
0.7021	Intermediate Similarity	NPD6618	Phase 2
0.7021	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4583	Approved
0.702	Intermediate Similarity	NPD4040	Phase 1
0.702	Intermediate Similarity	NPD4582	Approved
0.7011	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6896	Approved
0.7006	Intermediate Similarity	NPD5720	Discontinued
0.7006	Intermediate Similarity	NPD6895	Approved
0.6994	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3705	Approved
0.6977	Remote Similarity	NPD7124	Phase 2
0.6973	Remote Similarity	NPD5313	Approved
0.6973	Remote Similarity	NPD5312	Approved
0.697	Remote Similarity	NPD4004	Approved
0.697	Remote Similarity	NPD4002	Approved
0.6964	Remote Similarity	NPD4108	Discontinued
0.6954	Remote Similarity	NPD4482	Phase 3
0.6946	Remote Similarity	NPD2653	Approved
0.6946	Remote Similarity	NPD2492	Phase 1
0.6941	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6688	Approved
0.694	Remote Similarity	NPD6687	Approved
0.6935	Remote Similarity	NPD7479	Phase 2
0.6932	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4005	Discontinued
0.6927	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5977	Approved
0.6927	Remote Similarity	NPD5978	Approved
0.6919	Remote Similarity	NPD2677	Approved
0.6911	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4236	Phase 3
0.6901	Remote Similarity	NPD4237	Approved
0.6898	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4873	Discontinued
0.6879	Remote Similarity	NPD2120	Phase 2
0.6872	Remote Similarity	NPD5582	Discontinued
0.6868	Remote Similarity	NPD5677	Discontinued
0.6867	Remote Similarity	NPD3532	Approved
0.6867	Remote Similarity	NPD3531	Approved
0.6867	Remote Similarity	NPD3530	Approved
0.6864	Remote Similarity	NPD2154	Approved
0.6864	Remote Similarity	NPD2156	Approved
0.6864	Remote Similarity	NPD2155	Approved
0.6863	Remote Similarity	NPD3816	Phase 1
0.6863	Remote Similarity	NPD3815	Phase 1
0.686	Remote Similarity	NPD6748	Discontinued
0.6848	Remote Similarity	NPD4083	Discontinued
0.6845	Remote Similarity	NPD7047	Phase 3
0.6845	Remote Similarity	NPD2989	Phase 2
0.6845	Remote Similarity	NPD2986	Phase 2
0.6842	Remote Similarity	NPD4257	Approved
0.6842	Remote Similarity	NPD4256	Phase 2
0.6837	Remote Similarity	NPD7034	Discontinued
0.6834	Remote Similarity	NPD3057	Approved
0.6816	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8153	Approved
0.6816	Remote Similarity	NPD8152	Approved
0.681	Remote Similarity	NPD6997	Phase 2
0.6807	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5177	Phase 3
0.6802	Remote Similarity	NPD6674	Discontinued
0.68	Remote Similarity	NPD2874	Phase 2
0.68	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5095	Phase 3
0.6791	Remote Similarity	NPD5096	Phase 3

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