NPASS Compound

Structure

CID304675 OpenBabel06191716112D 24 28 0 0 1 0 0 0 0 0999 V2000 -0.7702 4.8900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5399 0.8891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7699 -0.4445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7698 2.2230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3103 -0.4445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3101 1.3339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7703 -0.4445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4486 0.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7701 4.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7700 1.3336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5402 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5401 0.8892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0803 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0802 0.8893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 2.6675 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7702 1.3336 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.8891 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7701 2.2228 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 -1.5400 3.5564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5610 2.6794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9260 -0.2745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9259 1.1642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 3.5565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 3 1 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 10 2 0 0 0 0 4 15 1 0 0 0 0 5 11 2 0 0 0 0 5 13 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 19 1 0 0 0 0 8 22 1 0 0 0 0 8 23 1 0 0 0 0 9 20 2 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 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 18 1 0 0 0 0 15 24 1 1 0 0 0 16 12 1 6 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 1 0 0 0 18 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	329.13
Volume:	318.867
LogP:	1.438
LogD:	1.647
LogS:	-2.364
# Rotatable Bonds:	2
TPSA:	68.23
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	4.169
Fsp3:	0.5
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:	-4.735
MDCK Permeability:	5.4400734370574355e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.181
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.666

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	66.29887390136719%
Volume Distribution (VD):	1.722
Pgp-substrate:	33.28745651245117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.713
CYP1A2-substrate:	0.285
CYP2C19-inhibitor:	0.131
CYP2C19-substrate:	0.77
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.436
CYP2D6-inhibitor:	0.952
CYP2D6-substrate:	0.596
CYP3A4-inhibitor:	0.58
CYP3A4-substrate:	0.432

ADMET: Excretion

Clearance (CL):	12.775
Half-life (T1/2):	0.353

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.326
AMES Toxicity:	0.118
Rat Oral Acute Toxicity:	0.882
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.056
Carcinogencity:	0.915
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC304675

Natural Product ID:	NPC304675
*Common Name:**	VDUHVXXNLXFPLR-WNRNVDISSA-N
IUPAC Name:	n.a.
Synonyms:	2-O-Acetyllycorine
Standard InCHIKey:	VDUHVXXNLXFPLR-WNRNVDISSA-N
Standard InCHI:	InChI=1S/C18H19NO5/c1-9(20)24-15-4-10-2-3-19-7-11-5-13-14(23-8-22-13)6-12(11)16(17(10)19)18(15)21/h4-6,15-18,21H,2-3,7-8H2,1H3/p+1/t15-,16-,17+,18+/m0/s1
SMILES:	CC(=O)O[C@H]1C=C2CC[NH+]3Cc4cc5c(cc4[C@@H]([C@@H]23)[C@@H]1O)OCO5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516707
PubChem CID:	25147570
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]
NPO1598	Leucojum vernum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1598	Leucojum vernum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25024	Lycoris traubii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1598	Leucojum vernum	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
IC50	12
MIC	2
Others	2

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	3
Organism	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	6.11	ug.mL-1	PMID[464889]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[464890]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	10000.0	nM	PMID[464890]
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[464890]
NPT3190	Cell Line	NHDF	Homo sapiens	IC50	>	100000.0	nM	PMID[464890]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	0.15	ug.mL-1	PMID[464889]
NPT2	Others	Unspecified		Ratio IC50	=	40.7	n.a.	PMID[464889]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	8.21	ug.mL-1	PMID[464889]
NPT2	Others	Unspecified		Ratio IC50	=	0.7	n.a.	PMID[464889]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[464890]
NPT27	Others	Unspecified		IC50	=	88500.0	nM	PMID[464890]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[464890]
NPT24393	ORGANISM	Flavobacterium columnare	Flavobacterium columnare	MIC	=	16.6	ug.mL-1	PMID[464891]
NPT24393	ORGANISM	Flavobacterium columnare	Flavobacterium columnare	MIC	=	3.3	ug.mL-1	PMID[464891]

☑ 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 NPC304675 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	215
0.1-0.2	1119
0.2-0.3	3298
0.3-0.4	10790
0.4-0.5	8735
0.5-0.6	13060
0.6-0.7	4371
0.7-0.8	922
0.8-0.85	101
0.85-0.9	37
0.9-0.95	32
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC237044
0.9876	High Similarity	NPC474325
0.9815	High Similarity	NPC474745
0.9686	High Similarity	NPC474324
0.9686	High Similarity	NPC57812
0.9636	High Similarity	NPC475981
0.9636	High Similarity	NPC474746
0.9625	High Similarity	NPC475845
0.9565	High Similarity	NPC474708
0.9563	High Similarity	NPC190332
0.9563	High Similarity	NPC181653
0.9521	High Similarity	NPC230098
0.9497	High Similarity	NPC320104
0.9451	High Similarity	NPC474470
0.9441	High Similarity	NPC100566
0.9146	High Similarity	NPC266176
0.9146	High Similarity	NPC290759
0.9146	High Similarity	NPC82533
0.9146	High Similarity	NPC158148
0.9091	High Similarity	NPC311991
0.9036	High Similarity	NPC477640
0.9036	High Similarity	NPC470739
0.9036	High Similarity	NPC225597
0.903	High Similarity	NPC475686
0.903	High Similarity	NPC58766
0.9012	High Similarity	NPC205167
0.9012	High Similarity	NPC249274
0.9012	High Similarity	NPC4304
0.8976	High Similarity	NPC474475
0.8935	High Similarity	NPC118633
0.8935	High Similarity	NPC148693
0.8935	High Similarity	NPC15919
0.8935	High Similarity	NPC294790
0.8929	High Similarity	NPC187678
0.8909	High Similarity	NPC476002
0.8896	High Similarity	NPC215829
0.8896	High Similarity	NPC97072
0.8772	High Similarity	NPC244554
0.8765	High Similarity	NPC78733
0.8757	High Similarity	NPC33256
0.8698	High Similarity	NPC65403
0.8675	High Similarity	NPC218614
0.8642	High Similarity	NPC223124
0.8639	High Similarity	NPC75958
0.8631	High Similarity	NPC252960
0.8623	High Similarity	NPC247972
0.8596	High Similarity	NPC49353
0.8571	High Similarity	NPC9867
0.8563	High Similarity	NPC275132
0.8538	High Similarity	NPC2314
0.8528	High Similarity	NPC148898
0.8519	High Similarity	NPC223125
0.8512	High Similarity	NPC180306
0.8485	Intermediate Similarity	NPC147091
0.8415	Intermediate Similarity	NPC210148
0.8415	Intermediate Similarity	NPC233029
0.8412	Intermediate Similarity	NPC210918
0.8402	Intermediate Similarity	NPC231198
0.8395	Intermediate Similarity	NPC475959
0.8383	Intermediate Similarity	NPC59028
0.8383	Intermediate Similarity	NPC92191
0.8383	Intermediate Similarity	NPC111485
0.8383	Intermediate Similarity	NPC477080
0.8382	Intermediate Similarity	NPC199465
0.8382	Intermediate Similarity	NPC128560
0.8382	Intermediate Similarity	NPC229166
0.8352	Intermediate Similarity	NPC116284
0.8352	Intermediate Similarity	NPC248642
0.8343	Intermediate Similarity	NPC126284
0.8343	Intermediate Similarity	NPC32154
0.8333	Intermediate Similarity	NPC80472
0.8333	Intermediate Similarity	NPC241704
0.8305	Intermediate Similarity	NPC156576
0.8294	Intermediate Similarity	NPC302527
0.8294	Intermediate Similarity	NPC232514
0.8294	Intermediate Similarity	NPC16805
0.8294	Intermediate Similarity	NPC276944
0.8294	Intermediate Similarity	NPC167546
0.8294	Intermediate Similarity	NPC238530
0.8293	Intermediate Similarity	NPC274026
0.8286	Intermediate Similarity	NPC320223
0.8286	Intermediate Similarity	NPC114364
0.8268	Intermediate Similarity	NPC237579
0.8263	Intermediate Similarity	NPC146288
0.8263	Intermediate Similarity	NPC234392
0.8263	Intermediate Similarity	NPC31311
0.8246	Intermediate Similarity	NPC24264
0.8246	Intermediate Similarity	NPC476432
0.8235	Intermediate Similarity	NPC59567
0.8225	Intermediate Similarity	NPC165797
0.8212	Intermediate Similarity	NPC162694
0.8208	Intermediate Similarity	NPC474953
0.8204	Intermediate Similarity	NPC41178
0.8204	Intermediate Similarity	NPC138487
0.8204	Intermediate Similarity	NPC216459
0.8198	Intermediate Similarity	NPC301189
0.8198	Intermediate Similarity	NPC150879
0.8198	Intermediate Similarity	NPC298186
0.8198	Intermediate Similarity	NPC247389
0.8193	Intermediate Similarity	NPC133011
0.8193	Intermediate Similarity	NPC82285
0.8187	Intermediate Similarity	NPC225774
0.8146	Intermediate Similarity	NPC233718
0.8146	Intermediate Similarity	NPC102760
0.814	Intermediate Similarity	NPC219341
0.8136	Intermediate Similarity	NPC99179
0.8132	Intermediate Similarity	NPC94499
0.8125	Intermediate Similarity	NPC283999
0.8125	Intermediate Similarity	NPC35680
0.8122	Intermediate Similarity	NPC82763
0.8111	Intermediate Similarity	NPC214116
0.8098	Intermediate Similarity	NPC130926
0.8092	Intermediate Similarity	NPC298979
0.809	Intermediate Similarity	NPC477561
0.809	Intermediate Similarity	NPC155442
0.809	Intermediate Similarity	NPC476574
0.809	Intermediate Similarity	NPC312918
0.8077	Intermediate Similarity	NPC319549
0.8061	Intermediate Similarity	NPC147390
0.8061	Intermediate Similarity	NPC246587
0.8061	Intermediate Similarity	NPC135538
0.8061	Intermediate Similarity	NPC428
0.8061	Intermediate Similarity	NPC476571
0.8061	Intermediate Similarity	NPC24233
0.8059	Intermediate Similarity	NPC106786
0.8057	Intermediate Similarity	NPC57272
0.8057	Intermediate Similarity	NPC19520
0.8057	Intermediate Similarity	NPC149090
0.805	Intermediate Similarity	NPC7018
0.8035	Intermediate Similarity	NPC124657
0.8023	Intermediate Similarity	NPC233650
0.8012	Intermediate Similarity	NPC160298
0.8012	Intermediate Similarity	NPC477559
0.8012	Intermediate Similarity	NPC306902
0.8012	Intermediate Similarity	NPC266753
0.8012	Intermediate Similarity	NPC232924
0.8	Intermediate Similarity	NPC6152
0.8	Intermediate Similarity	NPC179825
0.8	Intermediate Similarity	NPC135772
0.8	Intermediate Similarity	NPC191376
0.8	Intermediate Similarity	NPC321505
0.7989	Intermediate Similarity	NPC474607
0.7989	Intermediate Similarity	NPC210140
0.7988	Intermediate Similarity	NPC76079
0.7988	Intermediate Similarity	NPC185838
0.7978	Intermediate Similarity	NPC477560
0.7978	Intermediate Similarity	NPC475754
0.7978	Intermediate Similarity	NPC63152
0.7977	Intermediate Similarity	NPC212794
0.7977	Intermediate Similarity	NPC306843
0.7977	Intermediate Similarity	NPC13504
0.7977	Intermediate Similarity	NPC253043
0.7977	Intermediate Similarity	NPC96603
0.7977	Intermediate Similarity	NPC78222
0.7977	Intermediate Similarity	NPC196447
0.7977	Intermediate Similarity	NPC134858
0.7977	Intermediate Similarity	NPC136508
0.7977	Intermediate Similarity	NPC477563
0.7967	Intermediate Similarity	NPC141440
0.7964	Intermediate Similarity	NPC220858
0.7964	Intermediate Similarity	NPC88249
0.7964	Intermediate Similarity	NPC151895
0.7964	Intermediate Similarity	NPC192768
0.7964	Intermediate Similarity	NPC97221
0.7963	Intermediate Similarity	NPC213206
0.7963	Intermediate Similarity	NPC474915
0.7963	Intermediate Similarity	NPC328750
0.7963	Intermediate Similarity	NPC188163
0.7957	Intermediate Similarity	NPC73020
0.7957	Intermediate Similarity	NPC124302
0.7957	Intermediate Similarity	NPC215098
0.7957	Intermediate Similarity	NPC14622
0.7957	Intermediate Similarity	NPC70290
0.7957	Intermediate Similarity	NPC46744
0.7953	Intermediate Similarity	NPC69360
0.7952	Intermediate Similarity	NPC59907
0.7952	Intermediate Similarity	NPC37144
0.7944	Intermediate Similarity	NPC476575
0.7944	Intermediate Similarity	NPC474650
0.7943	Intermediate Similarity	NPC241055
0.7941	Intermediate Similarity	NPC323443
0.7941	Intermediate Similarity	NPC180756
0.7933	Intermediate Similarity	NPC220961
0.7919	Intermediate Similarity	NPC324144
0.7914	Intermediate Similarity	NPC267414
0.7904	Intermediate Similarity	NPC477565
0.7904	Intermediate Similarity	NPC103379
0.7901	Intermediate Similarity	NPC314682
0.7895	Intermediate Similarity	NPC40389
0.7895	Intermediate Similarity	NPC78359
0.7895	Intermediate Similarity	NPC475326
0.7895	Intermediate Similarity	NPC65490
0.7895	Intermediate Similarity	NPC315707
0.7895	Intermediate Similarity	NPC148014
0.7892	Intermediate Similarity	NPC476151
0.7886	Intermediate Similarity	NPC474931
0.7886	Intermediate Similarity	NPC81218
0.7886	Intermediate Similarity	NPC158376
0.7886	Intermediate Similarity	NPC12053
0.7886	Intermediate Similarity	NPC117188

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 NPC304675 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	557
0.2-0.3	962
0.3-0.4	2254
0.4-0.5	2674
0.5-0.6	1772
0.6-0.7	658
0.7-0.8	118
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8256	Intermediate Similarity	NPD4481	Phase 3
0.8253	Intermediate Similarity	NPD4773	Phase 2
0.8253	Intermediate Similarity	NPD4772	Phase 2
0.8198	Intermediate Similarity	NPD2970	Approved
0.8198	Intermediate Similarity	NPD2969	Approved
0.814	Intermediate Similarity	NPD3051	Approved
0.8081	Intermediate Similarity	NPD6107	Approved
0.8077	Intermediate Similarity	NPD7296	Approved
0.8046	Intermediate Similarity	NPD27	Approved
0.8046	Intermediate Similarity	NPD2489	Approved
0.7989	Intermediate Similarity	NPD7281	Phase 3
0.7989	Intermediate Similarity	NPD7280	Phase 3
0.7963	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD4420	Approved
0.7931	Intermediate Similarity	NPD6071	Discontinued
0.7895	Intermediate Similarity	NPD2560	Approved
0.7895	Intermediate Similarity	NPD2563	Approved
0.7884	Intermediate Similarity	NPD5006	Approved
0.7884	Intermediate Similarity	NPD5005	Approved
0.7845	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD5313	Approved
0.7809	Intermediate Similarity	NPD5312	Approved
0.7798	Intermediate Similarity	NPD3640	Phase 3
0.7798	Intermediate Similarity	NPD3639	Approved
0.7798	Intermediate Similarity	NPD3641	Approved
0.7784	Intermediate Similarity	NPD4584	Approved
0.774	Intermediate Similarity	NPD2898	Approved
0.7697	Intermediate Similarity	NPD4236	Phase 3
0.7697	Intermediate Similarity	NPD4237	Approved
0.7692	Intermediate Similarity	NPD7310	Approved
0.7692	Intermediate Similarity	NPD7312	Approved
0.7692	Intermediate Similarity	NPD7311	Approved
0.7692	Intermediate Similarity	NPD7313	Approved
0.766	Intermediate Similarity	NPD5582	Discontinued
0.765	Intermediate Similarity	NPD7309	Approved
0.7647	Intermediate Similarity	NPD4210	Discontinued
0.763	Intermediate Similarity	NPD2977	Approved
0.763	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD2978	Approved
0.7614	Intermediate Similarity	NPD7827	Phase 1
0.7568	Intermediate Similarity	NPD4663	Approved
0.7566	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5773	Approved
0.7529	Intermediate Similarity	NPD5772	Approved
0.7528	Intermediate Similarity	NPD4166	Phase 2
0.7527	Intermediate Similarity	NPD7906	Approved
0.75	Intermediate Similarity	NPD4578	Approved
0.75	Intermediate Similarity	NPD5241	Discontinued
0.75	Intermediate Similarity	NPD4577	Approved
0.7471	Intermediate Similarity	NPD7298	Approved
0.7459	Intermediate Similarity	NPD8054	Approved
0.7459	Intermediate Similarity	NPD6851	Approved
0.7459	Intermediate Similarity	NPD6853	Approved
0.7459	Intermediate Similarity	NPD8053	Approved
0.7447	Intermediate Similarity	NPD2490	Approved
0.7447	Intermediate Similarity	NPD2488	Approved
0.7432	Intermediate Similarity	NPD6297	Approved
0.743	Intermediate Similarity	NPD4010	Discontinued
0.7418	Intermediate Similarity	NPD8156	Discontinued
0.7405	Intermediate Similarity	NPD2968	Approved
0.7405	Intermediate Similarity	NPD2971	Approved
0.7401	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7833	Phase 2
0.7401	Intermediate Similarity	NPD7831	Phase 2
0.7399	Intermediate Similarity	NPD4017	Approved
0.7384	Intermediate Similarity	NPD6030	Approved
0.7384	Intermediate Similarity	NPD6031	Approved
0.7368	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8099	Discontinued
0.7363	Intermediate Similarity	NPD8252	Approved
0.7363	Intermediate Similarity	NPD8251	Approved
0.7346	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5604	Discontinued
0.7283	Intermediate Similarity	NPD4727	Phase 1
0.7263	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3656	Approved
0.7254	Intermediate Similarity	NPD2975	Approved
0.7254	Intermediate Similarity	NPD2973	Approved
0.7254	Intermediate Similarity	NPD2974	Approved
0.7251	Intermediate Similarity	NPD6666	Approved
0.7251	Intermediate Similarity	NPD6667	Approved
0.7247	Intermediate Similarity	NPD4965	Approved
0.7247	Intermediate Similarity	NPD4967	Phase 2
0.7247	Intermediate Similarity	NPD4966	Approved
0.7245	Intermediate Similarity	NPD3057	Approved
0.7241	Intermediate Similarity	NPD3687	Approved
0.7241	Intermediate Similarity	NPD3686	Approved
0.7231	Intermediate Similarity	NPD4107	Approved
0.7231	Intermediate Similarity	NPD4580	Approved
0.7194	Intermediate Similarity	NPD3452	Approved
0.7194	Intermediate Similarity	NPD2493	Approved
0.7194	Intermediate Similarity	NPD2494	Approved
0.7194	Intermediate Similarity	NPD3450	Approved
0.7175	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4582	Approved
0.7172	Intermediate Similarity	NPD4583	Approved
0.7167	Intermediate Similarity	NPD6234	Discontinued
0.7163	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD2972	Approved
0.7157	Intermediate Similarity	NPD3533	Approved
0.7152	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6788	Approved
0.7143	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6723	Discontinued
0.7128	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4666	Phase 3
0.7127	Intermediate Similarity	NPD5677	Discontinued
0.7126	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2492	Phase 1
0.7121	Intermediate Similarity	NPD4004	Approved
0.7121	Intermediate Similarity	NPD4002	Approved
0.712	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6997	Phase 2
0.7107	Intermediate Similarity	NPD4482	Phase 3
0.7102	Intermediate Similarity	NPD4005	Discontinued
0.7093	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7228	Approved
0.7079	Intermediate Similarity	NPD37	Approved
0.7076	Intermediate Similarity	NPD4162	Approved
0.7076	Intermediate Similarity	NPD5177	Phase 3
0.7076	Intermediate Similarity	NPD3060	Approved
0.7073	Intermediate Similarity	NPD7047	Phase 3
0.7072	Intermediate Similarity	NPD5709	Phase 3
0.7071	Intermediate Similarity	NPD3448	Approved
0.7071	Intermediate Similarity	NPD2491	Approved
0.7068	Intermediate Similarity	NPD6842	Approved
0.7068	Intermediate Similarity	NPD6841	Approved
0.7068	Intermediate Similarity	NPD6843	Phase 3
0.7063	Intermediate Similarity	NPD3705	Approved
0.7059	Intermediate Similarity	NPD1375	Discontinued
0.7035	Intermediate Similarity	NPD5754	Discontinued
0.7033	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6386	Approved
0.7022	Intermediate Similarity	NPD6385	Approved
0.7016	Intermediate Similarity	NPD3857	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6688	Approved
0.7011	Intermediate Similarity	NPD3124	Discontinued
0.7011	Intermediate Similarity	NPD2420	Approved
0.7011	Intermediate Similarity	NPD6687	Approved
0.7011	Intermediate Similarity	NPD2421	Approved
0.7006	Intermediate Similarity	NPD2238	Phase 2
0.7006	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4040	Phase 1
0.7	Intermediate Similarity	NPD2161	Phase 2
0.7	Intermediate Similarity	NPD5977	Approved
0.7	Intermediate Similarity	NPD5978	Approved
0.6988	Remote Similarity	NPD5718	Phase 2
0.6984	Remote Similarity	NPD7549	Discontinued
0.698	Remote Similarity	NPD4859	Phase 1
0.6977	Remote Similarity	NPD6625	Approved
0.6971	Remote Similarity	NPD1424	Approved
0.697	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5676	Approved
0.6954	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7497	Discontinued
0.6944	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4108	Discontinued
0.694	Remote Similarity	NPD2904	Discontinued
0.6936	Remote Similarity	NPD6331	Phase 2
0.6935	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7240	Approved
0.6923	Remote Similarity	NPD2653	Approved
0.6923	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD3885	Approved
0.6905	Remote Similarity	NPD3109	Approved
0.6905	Remote Similarity	NPD3110	Approved
0.6902	Remote Similarity	NPD7199	Phase 2
0.6897	Remote Similarity	NPD2677	Approved
0.6895	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5976	Discontinued
0.6893	Remote Similarity	NPD2122	Discontinued
0.6889	Remote Similarity	NPD3384	Approved
0.6889	Remote Similarity	NPD3383	Approved
0.6889	Remote Similarity	NPD3382	Approved
0.6889	Remote Similarity	NPD4433	Discontinued
0.6885	Remote Similarity	NPD7400	Phase 3
0.6882	Remote Similarity	NPD6896	Approved
0.6882	Remote Similarity	NPD6895	Approved
0.6882	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7999	Approved
0.6881	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6674	Discontinued
0.6875	Remote Similarity	NPD3536	Discontinued
0.6875	Remote Similarity	NPD4123	Phase 3
0.6857	Remote Similarity	NPD3845	Phase 1
0.6857	Remote Similarity	NPD7124	Phase 2
0.6845	Remote Similarity	NPD2674	Phase 3
0.6842	Remote Similarity	NPD7038	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