NPASS Compound

Structure

CID237044 OpenBabel06191716032D 24 28 0 0 1 0 0 0 0 0999 V2000 -0.7695 -4.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5397 -0.8888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7697 0.4445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7699 -2.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3099 0.4442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3095 -1.3339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7702 0.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4477 -0.4453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5395 -3.5561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7700 -1.3333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5399 -0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5397 -0.8892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -2.6670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0797 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0795 -0.8895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7699 -1.3334 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0002 -0.8889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7697 -2.2224 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 -2.3094 -4.0007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -3.5842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9253 0.2740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9250 -1.1644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5396 -2.6670 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 13 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 15 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 18 1 0 0 0 0 13 21 1 6 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 12 1 1 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 6 0 0 0 18 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	329.13
Volume:	318.867
LogP:	1.601
LogD:	1.568
LogS:	-2.238
# 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:	4.198
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:	-4.739
MDCK Permeability:	4.8694826546125114e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.356
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.714

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.989
Plasma Protein Binding (PPB):	63.77898406982422%
Volume Distribution (VD):	1.897
Pgp-substrate:	37.77572250366211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.692
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.713
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.427
CYP2D6-inhibitor:	0.961
CYP2D6-substrate:	0.579
CYP3A4-inhibitor:	0.426
CYP3A4-substrate:	0.391

ADMET: Excretion

Clearance (CL):	13.444
Half-life (T1/2):	0.447

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.222
Drug-inuced Liver Injury (DILI):	0.258
AMES Toxicity:	0.077
Rat Oral Acute Toxicity:	0.928
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.055
Carcinogencity:	0.927
Eye Corrosion:	0.004
Eye Irritation:	0.012
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: NPC237044

Natural Product ID:	NPC237044
*Common Name:**	BIGUPJIJZYZJMV-VIBAHUMZSA-N
IUPAC Name:	n.a.
Synonyms:	1-Acetoxylycorine; 1-Acetyllycorine; 1-O-Acetyllycorine
Standard InCHIKey:	BIGUPJIJZYZJMV-VIBAHUMZSA-N
Standard InCHI:	InChI=1S/C18H19NO5/c1-9(20)24-18-13(21)4-10-2-3-19-7-11-5-14-15(23-8-22-14)6-12(11)16(18)17(10)19/h4-6,13,16-18,21H,2-3,7-8H2,1H3/t13-,16-,17+,18+/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@@H](O)C=C2[C@@H]3[C@@H]1c1cc4OCOc4cc1CN3CC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251077
PubChem CID:	443672
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]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7773	Crinum moorei	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]
NPO7773	Crinum moorei	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
EC50	2
GI50	8
IC50	12
Ki	3
MIC	4
Others	4

Activity Type	# Activity
Cell Line	10
Individual Protein	4
NON-MOLECULAR	5
Organism	10
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	960.0	nM	PMID[524880]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	1.29	ug.mL-1	PMID[524881]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	7600.0	nM	PMID[524882]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Ki	=	7943.28	nM	PMID[524882]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[524883]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	10000.0	nM	PMID[524883]
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[524883]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Ki	=	430.0	nM	PMID[524885]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	4000.0	nM	PMID[524886]
NPT169	Cell Line	B16-F10	Mus musculus	GI50	=	43000.0	nM	PMID[524886]
NPT1125	Cell Line	T98G	Homo sapiens	GI50	=	2000.0	nM	PMID[524886]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	3000.0	nM	PMID[524886]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	=	3000.0	nM	PMID[524886]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	3000.0	nM	PMID[524886]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	5.22	ug.mL-1	PMID[524881]
NPT2	Others	Unspecified		Ratio IC50	=	0.2	n.a.	PMID[524881]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.36	ug.mL-1	PMID[524881]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.3	ug.mL-1	PMID[524881]
NPT2	Others	Unspecified		Ratio IC50	=	3.6	n.a.	PMID[524881]
NPT2	Others	Unspecified		Ratio IC50	=	4.3	n.a.	PMID[524881]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[524883]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	900.0	nM	PMID[524884]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	11000.0	nM	PMID[524886]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	4000.0	nM	PMID[524886]
NPT25178	ORGANISM	Edwardsiella ictaluri	Edwardsiella ictaluri	MIC	>	33.0	ug.mL-1	PMID[524887]
NPT24393	ORGANISM	Flavobacterium columnare	Flavobacterium columnare	MIC	=	3.3	ug.mL-1	PMID[524887]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	33.0	ug.mL-1	PMID[524887]
NPT1724	Organism	Dengue virus	Dengue virus	EC50	=	400.0	nM	PMID[524888]
NPT194	Organism	Dengue virus 2	Dengue virus 2	EC50	=	400.0	nM	PMID[524889]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	750.0	n.a.	PMID[524889]

☑ 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 NPC237044 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	217
0.1-0.2	1121
0.2-0.3	3306
0.3-0.4	10674
0.4-0.5	8663
0.5-0.6	12930
0.6-0.7	4679
0.7-0.8	904
0.8-0.85	120
0.85-0.9	34
0.9-0.95	33
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC474325
0.9938	High Similarity	NPC304675
0.9877	High Similarity	NPC474745
0.9697	High Similarity	NPC475981
0.9697	High Similarity	NPC474746
0.9625	High Similarity	NPC190332
0.9625	High Similarity	NPC57812
0.9625	High Similarity	NPC181653
0.9625	High Similarity	NPC474324
0.9581	High Similarity	NPC230098
0.9565	High Similarity	NPC475845
0.9506	High Similarity	NPC474708
0.9503	High Similarity	NPC100566
0.9437	High Similarity	NPC320104
0.9394	High Similarity	NPC474470
0.9096	High Similarity	NPC477640
0.9096	High Similarity	NPC470739
0.9096	High Similarity	NPC225597
0.9091	High Similarity	NPC82533
0.9091	High Similarity	NPC158148
0.9091	High Similarity	NPC58766
0.9091	High Similarity	NPC290759
0.9091	High Similarity	NPC475686
0.9091	High Similarity	NPC266176
0.9074	High Similarity	NPC249274
0.9074	High Similarity	NPC4304
0.9074	High Similarity	NPC205167
0.9036	High Similarity	NPC474475
0.9036	High Similarity	NPC311991
0.8988	High Similarity	NPC187678
0.897	High Similarity	NPC476002
0.8957	High Similarity	NPC97072
0.8957	High Similarity	NPC215829
0.8882	High Similarity	NPC294790
0.8882	High Similarity	NPC15919
0.8882	High Similarity	NPC148693
0.8882	High Similarity	NPC118633
0.8814	High Similarity	NPC33256
0.8721	High Similarity	NPC244554
0.8712	High Similarity	NPC78733
0.869	High Similarity	NPC252960
0.8647	High Similarity	NPC65403
0.8629	High Similarity	NPC9867
0.8623	High Similarity	NPC218614
0.8596	High Similarity	NPC2314
0.8589	High Similarity	NPC223124
0.8588	High Similarity	NPC75958
0.8571	High Similarity	NPC247972
0.8547	High Similarity	NPC49353
0.8545	High Similarity	NPC147091
0.8514	High Similarity	NPC275132
0.8476	Intermediate Similarity	NPC148898
0.8466	Intermediate Similarity	NPC223125
0.8462	Intermediate Similarity	NPC180306
0.8443	Intermediate Similarity	NPC59028
0.8443	Intermediate Similarity	NPC92191
0.8443	Intermediate Similarity	NPC111485
0.8439	Intermediate Similarity	NPC229166
0.8439	Intermediate Similarity	NPC128560
0.8439	Intermediate Similarity	NPC199465
0.8409	Intermediate Similarity	NPC116284
0.8409	Intermediate Similarity	NPC248642
0.84	Intermediate Similarity	NPC32154
0.84	Intermediate Similarity	NPC126284
0.8391	Intermediate Similarity	NPC241704
0.8387	Intermediate Similarity	NPC80472
0.8364	Intermediate Similarity	NPC233029
0.8364	Intermediate Similarity	NPC210148
0.8363	Intermediate Similarity	NPC210918
0.8362	Intermediate Similarity	NPC156576
0.8354	Intermediate Similarity	NPC274026
0.8353	Intermediate Similarity	NPC231198
0.8353	Intermediate Similarity	NPC232514
0.8353	Intermediate Similarity	NPC276944
0.8353	Intermediate Similarity	NPC238530
0.8344	Intermediate Similarity	NPC475959
0.8343	Intermediate Similarity	NPC320223
0.8343	Intermediate Similarity	NPC114364
0.8333	Intermediate Similarity	NPC477080
0.8284	Intermediate Similarity	NPC165797
0.8268	Intermediate Similarity	NPC162694
0.8266	Intermediate Similarity	NPC474953
0.8256	Intermediate Similarity	NPC298186
0.8256	Intermediate Similarity	NPC150879
0.8256	Intermediate Similarity	NPC301189
0.8253	Intermediate Similarity	NPC133011
0.8253	Intermediate Similarity	NPC82285
0.8246	Intermediate Similarity	NPC167546
0.8246	Intermediate Similarity	NPC302527
0.8246	Intermediate Similarity	NPC16805
0.8222	Intermediate Similarity	NPC237579
0.8214	Intermediate Similarity	NPC234392
0.8214	Intermediate Similarity	NPC31311
0.8214	Intermediate Similarity	NPC146288
0.8202	Intermediate Similarity	NPC233718
0.8198	Intermediate Similarity	NPC24264
0.8198	Intermediate Similarity	NPC476432
0.8192	Intermediate Similarity	NPC99179
0.8187	Intermediate Similarity	NPC59567
0.8187	Intermediate Similarity	NPC94499
0.8182	Intermediate Similarity	NPC283999
0.8177	Intermediate Similarity	NPC82763
0.8167	Intermediate Similarity	NPC214116
0.8155	Intermediate Similarity	NPC41178
0.8155	Intermediate Similarity	NPC138487
0.8155	Intermediate Similarity	NPC216459
0.815	Intermediate Similarity	NPC247389
0.815	Intermediate Similarity	NPC298979
0.8146	Intermediate Similarity	NPC312918
0.8146	Intermediate Similarity	NPC476574
0.8146	Intermediate Similarity	NPC477561
0.8146	Intermediate Similarity	NPC155442
0.814	Intermediate Similarity	NPC225774
0.8121	Intermediate Similarity	NPC135538
0.8121	Intermediate Similarity	NPC428
0.8121	Intermediate Similarity	NPC24233
0.8121	Intermediate Similarity	NPC476571
0.8121	Intermediate Similarity	NPC147390
0.8121	Intermediate Similarity	NPC246587
0.8114	Intermediate Similarity	NPC57272
0.8101	Intermediate Similarity	NPC102760
0.8092	Intermediate Similarity	NPC124657
0.8092	Intermediate Similarity	NPC219341
0.8081	Intermediate Similarity	NPC233650
0.8079	Intermediate Similarity	NPC35680
0.8061	Intermediate Similarity	NPC179825
0.8061	Intermediate Similarity	NPC321505
0.8061	Intermediate Similarity	NPC191376
0.8056	Intermediate Similarity	NPC135772
0.8049	Intermediate Similarity	NPC185838
0.8049	Intermediate Similarity	NPC130926
0.8046	Intermediate Similarity	NPC210140
0.8045	Intermediate Similarity	NPC474607
0.8035	Intermediate Similarity	NPC13504
0.8035	Intermediate Similarity	NPC134858
0.8035	Intermediate Similarity	NPC136508
0.8035	Intermediate Similarity	NPC253043
0.8035	Intermediate Similarity	NPC96603
0.8035	Intermediate Similarity	NPC78222
0.8035	Intermediate Similarity	NPC196447
0.8035	Intermediate Similarity	NPC477563
0.8035	Intermediate Similarity	NPC306843
0.8035	Intermediate Similarity	NPC212794
0.8033	Intermediate Similarity	NPC319549
0.8024	Intermediate Similarity	NPC220858
0.8024	Intermediate Similarity	NPC97221
0.8024	Intermediate Similarity	NPC88249
0.8024	Intermediate Similarity	NPC151895
0.8024	Intermediate Similarity	NPC192768
0.8012	Intermediate Similarity	NPC69360
0.8012	Intermediate Similarity	NPC106786
0.8011	Intermediate Similarity	NPC149090
0.8011	Intermediate Similarity	NPC19520
0.8	Intermediate Similarity	NPC476575
0.8	Intermediate Similarity	NPC7018
0.8	Intermediate Similarity	NPC474650
0.7977	Intermediate Similarity	NPC324144
0.7968	Intermediate Similarity	NPC267414
0.7965	Intermediate Similarity	NPC266753
0.7965	Intermediate Similarity	NPC160298
0.7965	Intermediate Similarity	NPC232924
0.7965	Intermediate Similarity	NPC306902
0.7965	Intermediate Similarity	NPC477559
0.7964	Intermediate Similarity	NPC477565
0.7964	Intermediate Similarity	NPC103379
0.7955	Intermediate Similarity	NPC6152
0.7953	Intermediate Similarity	NPC148014
0.7953	Intermediate Similarity	NPC78359
0.7953	Intermediate Similarity	NPC65490
0.7953	Intermediate Similarity	NPC315707
0.7953	Intermediate Similarity	NPC40389
0.7953	Intermediate Similarity	NPC475326
0.7952	Intermediate Similarity	NPC476151
0.7943	Intermediate Similarity	NPC158376
0.7943	Intermediate Similarity	NPC474931
0.7943	Intermediate Similarity	NPC306555
0.7943	Intermediate Similarity	NPC81218
0.7943	Intermediate Similarity	NPC117188
0.7943	Intermediate Similarity	NPC205421
0.7943	Intermediate Similarity	NPC145832
0.7943	Intermediate Similarity	NPC12053
0.7941	Intermediate Similarity	NPC39701
0.7941	Intermediate Similarity	NPC469817
0.7941	Intermediate Similarity	NPC172765
0.7941	Intermediate Similarity	NPC295691
0.7941	Intermediate Similarity	NPC127674
0.7941	Intermediate Similarity	NPC76079
0.7941	Intermediate Similarity	NPC110416
0.7941	Intermediate Similarity	NPC184026
0.7941	Intermediate Similarity	NPC5238
0.7941	Intermediate Similarity	NPC193949
0.7941	Intermediate Similarity	NPC278799
0.7941	Intermediate Similarity	NPC2413
0.7941	Intermediate Similarity	NPC276588
0.7941	Intermediate Similarity	NPC54379
0.7941	Intermediate Similarity	NPC207757
0.7941	Intermediate Similarity	NPC204828
0.7941	Intermediate Similarity	NPC249797
0.7941	Intermediate Similarity	NPC189266
0.7935	Intermediate Similarity	NPC226708

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 NPC237044 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	565
0.2-0.3	973
0.3-0.4	2234
0.4-0.5	2651
0.5-0.6	1783
0.6-0.7	671
0.7-0.8	118
0.8-0.85	6
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	NPD2969	Approved
0.8256	Intermediate Similarity	NPD2970	Approved
0.8208	Intermediate Similarity	NPD4481	Phase 3
0.8204	Intermediate Similarity	NPD4772	Phase 2
0.8204	Intermediate Similarity	NPD4773	Phase 2
0.8103	Intermediate Similarity	NPD2489	Approved
0.8103	Intermediate Similarity	NPD27	Approved
0.8092	Intermediate Similarity	NPD3051	Approved
0.8035	Intermediate Similarity	NPD6107	Approved
0.8033	Intermediate Similarity	NPD7296	Approved
0.7989	Intermediate Similarity	NPD6071	Discontinued
0.7953	Intermediate Similarity	NPD2560	Approved
0.7953	Intermediate Similarity	NPD2563	Approved
0.7944	Intermediate Similarity	NPD7280	Phase 3
0.7944	Intermediate Similarity	NPD7281	Phase 3
0.7914	Intermediate Similarity	NPD4420	Approved
0.7914	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD5005	Approved
0.7842	Intermediate Similarity	NPD5006	Approved
0.7797	Intermediate Similarity	NPD2898	Approved
0.7771	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5313	Approved
0.7765	Intermediate Similarity	NPD5312	Approved
0.7751	Intermediate Similarity	NPD3640	Phase 3
0.7751	Intermediate Similarity	NPD3641	Approved
0.7751	Intermediate Similarity	NPD3639	Approved
0.7747	Intermediate Similarity	NPD7311	Approved
0.7747	Intermediate Similarity	NPD7310	Approved
0.7747	Intermediate Similarity	NPD7313	Approved
0.7747	Intermediate Similarity	NPD7312	Approved
0.7738	Intermediate Similarity	NPD4584	Approved
0.7713	Intermediate Similarity	NPD5582	Discontinued
0.7705	Intermediate Similarity	NPD7309	Approved
0.7688	Intermediate Similarity	NPD2977	Approved
0.7688	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2978	Approved
0.7665	Intermediate Similarity	NPD7827	Phase 1
0.7651	Intermediate Similarity	NPD4236	Phase 3
0.7651	Intermediate Similarity	NPD4237	Approved
0.7622	Intermediate Similarity	NPD4663	Approved
0.7602	Intermediate Similarity	NPD4210	Discontinued
0.7592	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5772	Approved
0.7586	Intermediate Similarity	NPD5773	Approved
0.7581	Intermediate Similarity	NPD7906	Approved
0.756	Intermediate Similarity	NPD5241	Discontinued
0.7554	Intermediate Similarity	NPD4577	Approved
0.7554	Intermediate Similarity	NPD4578	Approved
0.7526	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8054	Approved
0.7514	Intermediate Similarity	NPD8053	Approved
0.75	Intermediate Similarity	NPD2488	Approved
0.75	Intermediate Similarity	NPD2490	Approved
0.7486	Intermediate Similarity	NPD4166	Phase 2
0.7486	Intermediate Similarity	NPD4010	Discontinued
0.7458	Intermediate Similarity	NPD7831	Phase 2
0.7458	Intermediate Similarity	NPD7833	Phase 2
0.7458	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7298	Approved
0.7427	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6851	Approved
0.7419	Intermediate Similarity	NPD6853	Approved
0.7394	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6297	Approved
0.7377	Intermediate Similarity	NPD8156	Discontinued
0.7366	Intermediate Similarity	NPD2971	Approved
0.7366	Intermediate Similarity	NPD2968	Approved
0.736	Intermediate Similarity	NPD5604	Discontinued
0.7356	Intermediate Similarity	NPD4017	Approved
0.7341	Intermediate Similarity	NPD6031	Approved
0.7341	Intermediate Similarity	NPD6030	Approved
0.7322	Intermediate Similarity	NPD8251	Approved
0.7322	Intermediate Similarity	NPD8252	Approved
0.7322	Intermediate Similarity	NPD8099	Discontinued
0.731	Intermediate Similarity	NPD6667	Approved
0.731	Intermediate Similarity	NPD6666	Approved
0.7303	Intermediate Similarity	NPD4967	Phase 2
0.7303	Intermediate Similarity	NPD4965	Approved
0.7303	Intermediate Similarity	NPD4966	Approved
0.7301	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3687	Approved
0.7299	Intermediate Similarity	NPD3686	Approved
0.7296	Intermediate Similarity	NPD3057	Approved
0.7287	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD3450	Approved
0.7245	Intermediate Similarity	NPD3452	Approved
0.7245	Intermediate Similarity	NPD2494	Approved
0.7245	Intermediate Similarity	NPD2493	Approved
0.7241	Intermediate Similarity	NPD4727	Phase 1
0.7232	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4582	Approved
0.7222	Intermediate Similarity	NPD6234	Discontinued
0.7222	Intermediate Similarity	NPD4583	Approved
0.7219	Intermediate Similarity	NPD3656	Approved
0.7216	Intermediate Similarity	NPD2974	Approved
0.7216	Intermediate Similarity	NPD2975	Approved
0.7216	Intermediate Similarity	NPD2973	Approved
0.7212	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3533	Approved
0.7208	Intermediate Similarity	NPD2972	Approved
0.7194	Intermediate Similarity	NPD4580	Approved
0.7194	Intermediate Similarity	NPD4107	Approved
0.7183	Intermediate Similarity	NPD6723	Discontinued
0.7182	Intermediate Similarity	NPD4666	Phase 3
0.7181	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4002	Approved
0.7172	Intermediate Similarity	NPD4004	Approved
0.7163	Intermediate Similarity	NPD6997	Phase 2
0.7135	Intermediate Similarity	NPD5177	Phase 3
0.7135	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD3060	Approved
0.7135	Intermediate Similarity	NPD37	Approved
0.7127	Intermediate Similarity	NPD5709	Phase 3
0.7122	Intermediate Similarity	NPD7047	Phase 3
0.7121	Intermediate Similarity	NPD2491	Approved
0.7121	Intermediate Similarity	NPD3448	Approved
0.7111	Intermediate Similarity	NPD6788	Approved
0.7108	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5677	Discontinued
0.7086	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2492	Phase 1
0.7071	Intermediate Similarity	NPD4482	Phase 3
0.7069	Intermediate Similarity	NPD2421	Approved
0.7069	Intermediate Similarity	NPD2420	Approved
0.7068	Intermediate Similarity	NPD3857	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2238	Phase 2
0.7062	Intermediate Similarity	NPD4005	Discontinued
0.7052	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4040	Phase 1
0.7047	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7549	Discontinued
0.7035	Intermediate Similarity	NPD4162	Approved
0.7031	Intermediate Similarity	NPD6843	Phase 3
0.7031	Intermediate Similarity	NPD6841	Approved
0.7031	Intermediate Similarity	NPD6842	Approved
0.7019	Intermediate Similarity	NPD3705	Approved
0.7018	Intermediate Similarity	NPD1375	Discontinued
0.7011	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5676	Approved
0.6995	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5754	Discontinued
0.6983	Remote Similarity	NPD6386	Approved
0.6983	Remote Similarity	NPD6385	Approved
0.6982	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6687	Approved
0.6973	Remote Similarity	NPD6688	Approved
0.6971	Remote Similarity	NPD3124	Discontinued
0.6966	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5977	Approved
0.6961	Remote Similarity	NPD5978	Approved
0.6959	Remote Similarity	NPD2161	Phase 2
0.6949	Remote Similarity	NPD2122	Discontinued
0.6947	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4859	Phase 1
0.6946	Remote Similarity	NPD5718	Phase 2
0.6944	Remote Similarity	NPD6625	Approved
0.6932	Remote Similarity	NPD4123	Phase 3
0.6932	Remote Similarity	NPD1424	Approved
0.6932	Remote Similarity	NPD3536	Discontinued
0.6928	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7497	Discontinued
0.6914	Remote Similarity	NPD3845	Phase 1
0.6906	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2674	Phase 3
0.6902	Remote Similarity	NPD2904	Discontinued
0.6901	Remote Similarity	NPD4108	Discontinued
0.6901	Remote Similarity	NPD1753	Discontinued
0.6898	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6331	Phase 2
0.6895	Remote Similarity	NPD7240	Approved
0.6895	Remote Similarity	NPD7039	Approved
0.6895	Remote Similarity	NPD7038	Approved
0.6893	Remote Similarity	NPD6090	Discontinued
0.6885	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2653	Approved
0.6878	Remote Similarity	NPD3885	Approved
0.6875	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7199	Phase 2
0.6864	Remote Similarity	NPD3109	Approved
0.6864	Remote Similarity	NPD3110	Approved
0.686	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2677	Approved
0.6854	Remote Similarity	NPD5976	Discontinued
0.6851	Remote Similarity	NPD3382	Approved
0.6851	Remote Similarity	NPD3383	Approved
0.6851	Remote Similarity	NPD3384	Approved
0.6851	Remote Similarity	NPD4433	Discontinued
0.6848	Remote Similarity	NPD7400	Phase 3
0.6847	Remote Similarity	NPD7607	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