NPASS Compound

Structure

NPC475845 OpenBabel07101718322D 29 33 0 0 1 0 0 0 0 0999 V2000 -0.8629 -5.9192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0226 -3.2486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0785 -5.5819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0812 -3.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5232 -0.5458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9599 0.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0900 -2.3208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1327 0.0805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1327 -1.5457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7927 0.1809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0881 -0.7326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9115 -1.3369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4285 -0.3260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4285 -1.1392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8369 -0.3260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8369 -1.1392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3272 -2.9674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2571 -4.5979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3184 -2.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7927 -1.6462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0299 -0.9996 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6142 -2.6301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.1985 -4.2606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4970 -1.9554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6102 -0.0748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6102 -1.3904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5058 -3.9513 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3770 -3.2767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 23 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 26 1 0 0 0 0 11 27 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 15 16 2 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 22 1 0 0 0 0 17 28 1 1 0 0 0 18 24 2 0 0 0 0 18 28 1 0 0 0 0 19 25 2 0 0 0 0 19 29 1 0 0 0 0 20 14 1 6 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 1 0 0 0 22 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	399.17
Volume:	394.205
LogP:	3.333
LogD:	2.743
LogS:	-3.956
# Rotatable Bonds:	6
TPSA:	74.3
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	4.3
Fsp3:	0.545
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:	-4.87
MDCK Permeability:	4.479119525058195e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.98
Plasma Protein Binding (PPB):	72.01244354248047%
Volume Distribution (VD):	2.207
Pgp-substrate:	14.599798202514648%

ADMET: Metabolism

CYP1A2-inhibitor:	0.745
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.624
CYP2C19-substrate:	0.304
CYP2C9-inhibitor:	0.164
CYP2C9-substrate:	0.364
CYP2D6-inhibitor:	0.974
CYP2D6-substrate:	0.383
CYP3A4-inhibitor:	0.907
CYP3A4-substrate:	0.327

ADMET: Excretion

Clearance (CL):	17.874
Half-life (T1/2):	0.393

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.156
Drug-inuced Liver Injury (DILI):	0.716
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.835
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.053
Carcinogencity:	0.482
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC475845

Natural Product ID:	NPC475845
*Common Name:**	FHZQSULZQZRVBO-GUGJDKNPSA-N
IUPAC Name:	n.a.
Synonyms:	1,2-Dipropionyllycorine
Standard InCHIKey:	FHZQSULZQZRVBO-GUGJDKNPSA-N
Standard InCHI:	InChI=1S/C22H25NO6/c1-3-18(24)28-17-7-12-5-6-23-10-13-8-15-16(27-11-26-15)9-14(13)20(21(12)23)22(17)29-19(25)4-2/h7-9,17,20-22H,3-6,10-11H2,1-2H3/t17-,20-,21+,22+/m0/s1
SMILES:	CCC(=O)O[C@H]1C=C2CCN3Cc4cc5c(cc4[C@@H]([C@@H]23)[C@@H]1OC(=O)CC)OCO5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517229
PubChem CID:	44570428
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004120] Lycorine-type amaryllidaceae alkaloids

*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
NPO25024	Lycoris traubii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19013823]
NPO40778	Alkaloid lycorine	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22019045]
NPO25024	Lycoris traubii	Species	Amaryllidaceae	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
GI50	8
IC50	3
Others	1

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	2
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	23.8	ug.mL-1	PMID[515697]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	22000.0	nM	PMID[515699]
NPT169	Cell Line	B16-F10	Mus musculus	GI50	=	29000.0	nM	PMID[515699]
NPT1125	Cell Line	T98G	Homo sapiens	GI50	=	600.0	nM	PMID[515699]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	4000.0	nM	PMID[515699]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	=	43000.0	nM	PMID[515699]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	41000.0	nM	PMID[515699]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	4.2	ug.mL-1	PMID[515697]
NPT2	Others	Unspecified		Ratio IC50	>	23.8	n.a.	PMID[515697]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2700.0	nM	PMID[515698]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	8000.0	nM	PMID[515699]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	3000.0	nM	PMID[515699]

☑ 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 NPC475845 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	242
0.1-0.2	1210
0.2-0.3	3759
0.3-0.4	11743
0.4-0.5	7752
0.5-0.6	13726
0.6-0.7	3306
0.7-0.8	772
0.8-0.85	112
0.85-0.9	46
0.9-0.95	18
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC474708
0.9935	High Similarity	NPC474324
0.9935	High Similarity	NPC57812
0.9627	High Similarity	NPC474325
0.9625	High Similarity	NPC304675
0.9568	High Similarity	NPC474745
0.9565	High Similarity	NPC237044
0.9394	High Similarity	NPC474746
0.9394	High Similarity	NPC475981
0.9281	High Similarity	NPC230098
0.9245	High Similarity	NPC320104
0.9207	High Similarity	NPC474470
0.9193	High Similarity	NPC181653
0.9193	High Similarity	NPC190332
0.9074	High Similarity	NPC100566
0.8987	High Similarity	NPC78733
0.8909	High Similarity	NPC65403
0.8902	High Similarity	NPC266176
0.8902	High Similarity	NPC82533
0.8902	High Similarity	NPC158148
0.8902	High Similarity	NPC290759
0.8848	High Similarity	NPC75958
0.8834	High Similarity	NPC247972
0.8795	High Similarity	NPC470739
0.8795	High Similarity	NPC477640
0.8795	High Similarity	NPC225597
0.8788	High Similarity	NPC475686
0.8788	High Similarity	NPC58766
0.8765	High Similarity	NPC4304
0.8742	High Similarity	NPC148898
0.8735	High Similarity	NPC311991
0.8735	High Similarity	NPC474475
0.8734	High Similarity	NPC223125
0.872	High Similarity	NPC180306
0.8698	High Similarity	NPC148693
0.8698	High Similarity	NPC294790
0.8698	High Similarity	NPC118633
0.8667	High Similarity	NPC476002
0.865	High Similarity	NPC249274
0.865	High Similarity	NPC97072
0.865	High Similarity	NPC205167
0.865	High Similarity	NPC215829
0.8625	High Similarity	NPC233029
0.8625	High Similarity	NPC223124
0.8625	High Similarity	NPC210148
0.8614	High Similarity	NPC210918
0.8608	High Similarity	NPC475959
0.8606	High Similarity	NPC231198
0.8589	High Similarity	NPC477080
0.8588	High Similarity	NPC15919
0.858	High Similarity	NPC187678
0.8545	High Similarity	NPC218614
0.8538	High Similarity	NPC244554
0.8531	High Similarity	NPC33256
0.8494	Intermediate Similarity	NPC302527
0.8494	Intermediate Similarity	NPC16805
0.8494	Intermediate Similarity	NPC167546
0.8466	Intermediate Similarity	NPC234392
0.8466	Intermediate Similarity	NPC31311
0.8466	Intermediate Similarity	NPC146288
0.8457	Intermediate Similarity	NPC237579
0.8443	Intermediate Similarity	NPC24264
0.8443	Intermediate Similarity	NPC476432
0.8439	Intermediate Similarity	NPC102760
0.8421	Intermediate Similarity	NPC35680
0.8405	Intermediate Similarity	NPC216459
0.8405	Intermediate Similarity	NPC138487
0.8405	Intermediate Similarity	NPC41178
0.8393	Intermediate Similarity	NPC247389
0.8393	Intermediate Similarity	NPC252960
0.8383	Intermediate Similarity	NPC225774
0.8343	Intermediate Similarity	NPC9867
0.8333	Intermediate Similarity	NPC219341
0.8333	Intermediate Similarity	NPC275132
0.8304	Intermediate Similarity	NPC2314
0.8302	Intermediate Similarity	NPC130926
0.8258	Intermediate Similarity	NPC63152
0.8258	Intermediate Similarity	NPC7018
0.8256	Intermediate Similarity	NPC49353
0.8253	Intermediate Similarity	NPC106786
0.8249	Intermediate Similarity	NPC141440
0.8246	Intermediate Similarity	NPC149090
0.8246	Intermediate Similarity	NPC19520
0.8232	Intermediate Similarity	NPC73020
0.8232	Intermediate Similarity	NPC14622
0.8232	Intermediate Similarity	NPC46744
0.8232	Intermediate Similarity	NPC124302
0.8232	Intermediate Similarity	NPC215098
0.8232	Intermediate Similarity	NPC70290
0.8214	Intermediate Similarity	NPC59567
0.8208	Intermediate Similarity	NPC241704
0.8204	Intermediate Similarity	NPC477559
0.8204	Intermediate Similarity	NPC306902
0.8204	Intermediate Similarity	NPC160298
0.8204	Intermediate Similarity	NPC232924
0.8204	Intermediate Similarity	NPC266753
0.8187	Intermediate Similarity	NPC6152
0.8182	Intermediate Similarity	NPC76079
0.8165	Intermediate Similarity	NPC188163
0.8165	Intermediate Similarity	NPC213206
0.8165	Intermediate Similarity	NPC328750
0.8165	Intermediate Similarity	NPC474915
0.8152	Intermediate Similarity	NPC119818
0.8152	Intermediate Similarity	NPC328700
0.8152	Intermediate Similarity	NPC202771
0.8152	Intermediate Similarity	NPC2173
0.815	Intermediate Similarity	NPC229166
0.815	Intermediate Similarity	NPC128560
0.815	Intermediate Similarity	NPC199465
0.8148	Intermediate Similarity	NPC37144
0.8148	Intermediate Similarity	NPC59907
0.8146	Intermediate Similarity	NPC166979
0.8144	Intermediate Similarity	NPC59028
0.8144	Intermediate Similarity	NPC92191
0.8144	Intermediate Similarity	NPC111485
0.8142	Intermediate Similarity	NPC226652
0.8142	Intermediate Similarity	NPC314100
0.8142	Intermediate Similarity	NPC120671
0.8142	Intermediate Similarity	NPC72788
0.8133	Intermediate Similarity	NPC323443
0.8133	Intermediate Similarity	NPC147091
0.8133	Intermediate Similarity	NPC180756
0.8129	Intermediate Similarity	NPC241055
0.8125	Intermediate Similarity	NPC248642
0.8125	Intermediate Similarity	NPC116284
0.8118	Intermediate Similarity	NPC80472
0.8114	Intermediate Similarity	NPC32154
0.8114	Intermediate Similarity	NPC126284
0.8114	Intermediate Similarity	NPC220961
0.8101	Intermediate Similarity	NPC314682
0.809	Intermediate Similarity	NPC162694
0.8081	Intermediate Similarity	NPC474953
0.8079	Intermediate Similarity	NPC156576
0.8072	Intermediate Similarity	NPC93593
0.8072	Intermediate Similarity	NPC99659
0.8072	Intermediate Similarity	NPC325871
0.8063	Intermediate Similarity	NPC128019
0.8063	Intermediate Similarity	NPC476567
0.8063	Intermediate Similarity	NPC136860
0.8059	Intermediate Similarity	NPC238530
0.8059	Intermediate Similarity	NPC232514
0.8059	Intermediate Similarity	NPC276944
0.8057	Intermediate Similarity	NPC114364
0.8057	Intermediate Similarity	NPC320223
0.8049	Intermediate Similarity	NPC274026
0.8037	Intermediate Similarity	NPC7467
0.8011	Intermediate Similarity	NPC267408
0.8	Intermediate Similarity	NPC283999
0.7976	Intermediate Similarity	NPC476572
0.7975	Intermediate Similarity	NPC476144
0.7975	Intermediate Similarity	NPC210437
0.7975	Intermediate Similarity	NPC106295
0.7975	Intermediate Similarity	NPC51957
0.7975	Intermediate Similarity	NPC16107
0.7965	Intermediate Similarity	NPC298979
0.7965	Intermediate Similarity	NPC150879
0.7964	Intermediate Similarity	NPC244112
0.7956	Intermediate Similarity	NPC319549
0.7955	Intermediate Similarity	NPC477560
0.7953	Intermediate Similarity	NPC168409
0.7953	Intermediate Similarity	NPC306669
0.7952	Intermediate Similarity	NPC82285
0.7952	Intermediate Similarity	NPC133011
0.7927	Intermediate Similarity	NPC130941
0.7921	Intermediate Similarity	NPC73492
0.7921	Intermediate Similarity	NPC299990
0.7921	Intermediate Similarity	NPC233718
0.7912	Intermediate Similarity	NPC94499
0.791	Intermediate Similarity	NPC99179
0.791	Intermediate Similarity	NPC27887
0.791	Intermediate Similarity	NPC470879
0.791	Intermediate Similarity	NPC258695
0.7907	Intermediate Similarity	NPC304659
0.7907	Intermediate Similarity	NPC86144
0.7901	Intermediate Similarity	NPC82763
0.7892	Intermediate Similarity	NPC476579
0.7889	Intermediate Similarity	NPC214116
0.7882	Intermediate Similarity	NPC165797
0.7879	Intermediate Similarity	NPC219162
0.7871	Intermediate Similarity	NPC160193
0.7865	Intermediate Similarity	NPC476574
0.7865	Intermediate Similarity	NPC32413
0.7865	Intermediate Similarity	NPC312918
0.7865	Intermediate Similarity	NPC155442
0.7865	Intermediate Similarity	NPC477561
0.7865	Intermediate Similarity	NPC474506
0.7861	Intermediate Similarity	NPC298186
0.7861	Intermediate Similarity	NPC301189
0.7857	Intermediate Similarity	NPC226708
0.7857	Intermediate Similarity	NPC475597
0.7857	Intermediate Similarity	NPC473716
0.7853	Intermediate Similarity	NPC23219
0.7853	Intermediate Similarity	NPC185838
0.7824	Intermediate Similarity	NPC118804
0.7818	Intermediate Similarity	NPC147390
0.7818	Intermediate Similarity	NPC428
0.7818	Intermediate Similarity	NPC246587
0.7818	Intermediate Similarity	NPC476571
0.7818	Intermediate Similarity	NPC135538
0.7818	Intermediate Similarity	NPC24233

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 NPC475845 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	594
0.2-0.3	948
0.3-0.4	2297
0.4-0.5	2698
0.5-0.6	1776
0.6-0.7	544
0.7-0.8	112
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8452	Intermediate Similarity	NPD4481	Phase 3
0.8383	Intermediate Similarity	NPD6107	Approved
0.8232	Intermediate Similarity	NPD4420	Approved
0.8165	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8152	Intermediate Similarity	NPD5006	Approved
0.8152	Intermediate Similarity	NPD5005	Approved
0.8098	Intermediate Similarity	NPD3640	Phase 3
0.8098	Intermediate Similarity	NPD3639	Approved
0.8098	Intermediate Similarity	NPD3641	Approved
0.8092	Intermediate Similarity	NPD5312	Approved
0.8092	Intermediate Similarity	NPD5313	Approved
0.8012	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4772	Phase 2
0.8012	Intermediate Similarity	NPD4773	Phase 2
0.7975	Intermediate Similarity	NPD4584	Approved
0.7966	Intermediate Similarity	NPD7280	Phase 3
0.7966	Intermediate Similarity	NPD7281	Phase 3
0.7956	Intermediate Similarity	NPD7296	Approved
0.7861	Intermediate Similarity	NPD2969	Approved
0.7861	Intermediate Similarity	NPD2970	Approved
0.7831	Intermediate Similarity	NPD4210	Discontinued
0.7803	Intermediate Similarity	NPD3051	Approved
0.7803	Intermediate Similarity	NPD4166	Phase 2
0.7744	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2489	Approved
0.7714	Intermediate Similarity	NPD27	Approved
0.7701	Intermediate Similarity	NPD6071	Discontinued
0.7667	Intermediate Similarity	NPD2968	Approved
0.7667	Intermediate Similarity	NPD2971	Approved
0.7661	Intermediate Similarity	NPD2563	Approved
0.7661	Intermediate Similarity	NPD2560	Approved
0.7647	Intermediate Similarity	NPD7298	Approved
0.7584	Intermediate Similarity	NPD8156	Discontinued
0.7574	Intermediate Similarity	NPD4017	Approved
0.756	Intermediate Similarity	NPD6031	Approved
0.756	Intermediate Similarity	NPD6030	Approved
0.754	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD5582	Discontinued
0.7532	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8099	Discontinued
0.7528	Intermediate Similarity	NPD8252	Approved
0.7528	Intermediate Similarity	NPD8251	Approved
0.7514	Intermediate Similarity	NPD2898	Approved
0.75	Intermediate Similarity	NPD7827	Phase 1
0.7486	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4107	Approved
0.7473	Intermediate Similarity	NPD7310	Approved
0.7473	Intermediate Similarity	NPD7312	Approved
0.7473	Intermediate Similarity	NPD7313	Approved
0.7473	Intermediate Similarity	NPD7311	Approved
0.7456	Intermediate Similarity	NPD4727	Phase 1
0.7455	Intermediate Similarity	NPD4236	Phase 3
0.7455	Intermediate Similarity	NPD4237	Approved
0.7432	Intermediate Similarity	NPD6851	Approved
0.7432	Intermediate Similarity	NPD7309	Approved
0.7432	Intermediate Similarity	NPD6853	Approved
0.7403	Intermediate Similarity	NPD6297	Approved
0.7399	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD4482	Phase 3
0.733	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2490	Approved
0.7326	Intermediate Similarity	NPD2488	Approved
0.7317	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6788	Approved
0.7312	Intermediate Similarity	NPD7906	Approved
0.7301	Intermediate Similarity	NPD2492	Phase 1
0.7299	Intermediate Similarity	NPD2978	Approved
0.7299	Intermediate Similarity	NPD5772	Approved
0.7299	Intermediate Similarity	NPD2977	Approved
0.7299	Intermediate Similarity	NPD5773	Approved
0.7288	Intermediate Similarity	NPD5677	Discontinued
0.7283	Intermediate Similarity	NPD6386	Approved
0.7283	Intermediate Similarity	NPD4577	Approved
0.7283	Intermediate Similarity	NPD4578	Approved
0.7283	Intermediate Similarity	NPD6385	Approved
0.7273	Intermediate Similarity	NPD7833	Phase 2
0.7273	Intermediate Similarity	NPD7831	Phase 2
0.7273	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5241	Discontinued
0.7258	Intermediate Similarity	NPD4663	Approved
0.7257	Intermediate Similarity	NPD5978	Approved
0.7257	Intermediate Similarity	NPD5977	Approved
0.7244	Intermediate Similarity	NPD3705	Approved
0.7243	Intermediate Similarity	NPD8054	Approved
0.7243	Intermediate Similarity	NPD8053	Approved
0.7234	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2975	Approved
0.7225	Intermediate Similarity	NPD2974	Approved
0.7225	Intermediate Similarity	NPD2973	Approved
0.7219	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4859	Phase 1
0.7207	Intermediate Similarity	NPD4010	Discontinued
0.7202	Intermediate Similarity	NPD4580	Approved
0.7202	Intermediate Similarity	NPD5754	Discontinued
0.7195	Intermediate Similarity	NPD2653	Approved
0.7191	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6625	Approved
0.7176	Intermediate Similarity	NPD3124	Discontinued
0.7175	Intermediate Similarity	NPD5604	Discontinued
0.7168	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6688	Approved
0.7167	Intermediate Similarity	NPD6687	Approved
0.716	Intermediate Similarity	NPD5718	Phase 2
0.7143	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1424	Approved
0.7135	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3656	Approved
0.7119	Intermediate Similarity	NPD4965	Approved
0.7119	Intermediate Similarity	NPD4967	Phase 2
0.7119	Intermediate Similarity	NPD4966	Approved
0.7118	Intermediate Similarity	NPD6666	Approved
0.7118	Intermediate Similarity	NPD6667	Approved
0.711	Intermediate Similarity	NPD3686	Approved
0.711	Intermediate Similarity	NPD3687	Approved
0.7086	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7110	Phase 1
0.7077	Intermediate Similarity	NPD3452	Approved
0.7077	Intermediate Similarity	NPD3450	Approved
0.7077	Intermediate Similarity	NPD2493	Approved
0.7077	Intermediate Similarity	NPD2494	Approved
0.7073	Intermediate Similarity	NPD3109	Approved
0.7073	Intermediate Similarity	NPD3110	Approved
0.7072	Intermediate Similarity	NPD5242	Approved
0.7065	Intermediate Similarity	NPD3885	Approved
0.7056	Intermediate Similarity	NPD4583	Approved
0.7056	Intermediate Similarity	NPD4582	Approved
0.7052	Intermediate Similarity	NPD5976	Discontinued
0.7048	Intermediate Similarity	NPD6896	Approved
0.7048	Intermediate Similarity	NPD6895	Approved
0.7045	Intermediate Similarity	NPD3384	Approved
0.7045	Intermediate Similarity	NPD3383	Approved
0.7045	Intermediate Similarity	NPD3382	Approved
0.7041	Intermediate Similarity	NPD3057	Approved
0.7039	Intermediate Similarity	NPD7400	Phase 3
0.7039	Intermediate Similarity	NPD6234	Discontinued
0.7037	Intermediate Similarity	NPD7291	Discontinued
0.7033	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD6723	Discontinued
0.7024	Intermediate Similarity	NPD1375	Discontinued
0.7018	Intermediate Similarity	NPD7124	Phase 2
0.7005	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4002	Approved
0.7005	Intermediate Similarity	NPD6997	Phase 2
0.7005	Intermediate Similarity	NPD4004	Approved
0.6988	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5353	Approved
0.6961	Remote Similarity	NPD7802	Discontinued
0.6961	Remote Similarity	NPD7047	Phase 3
0.6959	Remote Similarity	NPD5564	Approved
0.6954	Remote Similarity	NPD2972	Approved
0.6954	Remote Similarity	NPD3533	Approved
0.6949	Remote Similarity	NPD37	Approved
0.6935	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6875	Approved
0.6932	Remote Similarity	NPD6876	Approved
0.6927	Remote Similarity	NPD5980	Discovery
0.691	Remote Similarity	NPD4585	Approved
0.691	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4474	Approved
0.6909	Remote Similarity	NPD4475	Approved
0.6905	Remote Similarity	NPD4108	Discontinued
0.6902	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6873	Phase 2
0.6884	Remote Similarity	NPD4040	Phase 1
0.6882	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5297	Approved
0.6875	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4005	Discontinued
0.6869	Remote Similarity	NPD2491	Approved
0.6869	Remote Similarity	NPD3448	Approved
0.6865	Remote Similarity	NPD7228	Approved
0.6864	Remote Similarity	NPD2161	Phase 2
0.6862	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7549	Discontinued
0.6859	Remote Similarity	NPD3349	Phase 2
0.6857	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7248	Discontinued
0.6851	Remote Similarity	NPD5709	Phase 3
0.6845	Remote Similarity	NPD6111	Discontinued
0.6842	Remote Similarity	NPD5177	Phase 3
0.6842	Remote Similarity	NPD3060	Approved
0.6842	Remote Similarity	NPD4162	Approved
0.6834	Remote Similarity	NPD7497	Discontinued
0.6825	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4666	Phase 3
0.6806	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6331	Phase 2
0.6802	Remote Similarity	NPD8095	Phase 1

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