NPASS Compound

Structure

NPC69360 OpenBabel07101718182D 21 24 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 8 1 0 0 0 0 2 5 2 0 0 0 0 2 9 1 0 0 0 0 3 7 2 0 0 0 0 3 10 1 0 0 0 0 4 20 1 0 0 0 0 4 21 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 16 1 6 0 0 0 9 10 2 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 6 1 6 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 1 0 0 0 13 18 1 1 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	291.07
Volume:	267.03
LogP:	-0.399
LogD:	0.197
LogS:	-3.693
# Rotatable Bonds:	0
TPSA:	112.01
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.524
Synthetic Accessibility Score:	3.844
Fsp3:	0.357
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:	-5.71
MDCK Permeability:	4.727049145003548e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.348
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.599
Plasma Protein Binding (PPB):	58.33061981201172%
Volume Distribution (VD):	0.929
Pgp-substrate:	25.285900115966797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.296
CYP1A2-substrate:	0.63
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.282
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.215
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.061

ADMET: Excretion

Clearance (CL):	6.049
Half-life (T1/2):	0.373

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.778
AMES Toxicity:	0.248
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.181
Skin Sensitization:	0.041
Carcinogencity:	0.468
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.886

Download Data

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

Natural Product: NPC69360

Natural Product ID:	NPC69360
*Common Name:**	(+)-Lycoricidine
IUPAC Name:	(2S,3R,4S,4aR)-2,3,4-trihydroxy-3,4,4a,5-tetrahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
Synonyms:	7-Deoxynarciclasine
Standard InCHIKey:	YYDLFVZOIDOGSO-KKBFJBPOSA-N
Standard InCHI:	InChI=1S/C14H13NO6/c16-8-1-6-5-2-9-10(21-4-20-9)3-7(5)14(19)15-11(6)13(18)12(8)17/h1-3,8,11-13,16-18H,4H2,(H,15,19)/t8-,11+,12+,13-/m0/s1
SMILES:	O[C@H]1C=C2[C@H]([C@@H]([C@@H]1O)O)N=C(c1c2cc2OCOc2c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487798
PubChem CID:	73065
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000100] Phenanthridines and derivatives

*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
NPO32739	pancratium littorale	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1336040]

☑ 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	1
ED50	3
GI50	11
IC50	6
Others	20

Activity Type	# Activity
Cell Line	15
NON-MOLECULAR	2
Organism	9
Others	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	T/C	=	161.0	n.a.	PMID[458440]
NPT168	Cell Line	P388	Mus musculus	ED50	<	0.01	ug ml-1	PMID[458442]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI	=	0.12	ug ml-1	PMID[458442]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.093	ug.mL-1	PMID[458442]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	=	0.15	ug.mL-1	PMID[458442]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	0.062	ug.mL-1	PMID[458442]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.11	ug.mL-1	PMID[458442]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.019	ug ml-1	PMID[458443]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.07	ug.mL-1	PMID[458443]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.046	ug.mL-1	PMID[458443]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	0.12	ug.mL-1	PMID[458443]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.053	ug.mL-1	PMID[458443]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	=	0.084	ug.mL-1	PMID[458443]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	0.051	ug.mL-1	PMID[458443]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.02	ug ml-1	PMID[458440]
NPT33	Organism	Japanese encephalitis virus	Japanese encephalitis virus	IC50	=	0.056	ug.mL-1	PMID[458441]
NPT4327	Organism	Yellow fever virus	Yellow fever virus	IC50	=	0.053	ug.mL-1	PMID[458441]
NPT4328	Organism	Dengue virus type 4	Dengue virus 4	IC50	=	0.059	ug.mL-1	PMID[458441]
NPT27	Others	Unspecified		TI	=	4.9	n.a.	PMID[458441]
NPT27	Others	Unspecified		TI	=	5.6	n.a.	PMID[458441]
NPT27	Others	Unspecified		TI	=	4.2	n.a.	PMID[458441]
NPT341	Organism	Punta Toro virus	Punta Toro virus	IC50	=	0.042	ug.mL-1	PMID[458441]
NPT4329	Organism	Rift Valley fever virus	Rift Valley fever virus	IC50	=	0.15	ug.mL-1	PMID[458441]
NPT4330	Organism	Sandfly fever sicilian virus	Sandfly fever sicilian virus	IC50	=	0.058	ug.mL-1	PMID[458441]
NPT27	Others	Unspecified		TI	=	6.3	n.a.	PMID[458441]
NPT27	Others	Unspecified		TI	=	5.5	n.a.	PMID[458441]
NPT27	Others	Unspecified		TI	=	4.5	n.a.	PMID[458441]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	0.047	ug.mL-1	PMID[458442]
NPT35	Others	n.a.		Solubility	<	1000.0	ug.mL-1	PMID[458443]
NPT610	Others	Molecular identity unknown		Activity	=	6.0	%	PMID[458444]
NPT610	Others	Molecular identity unknown		Activity	=	28.0	%	PMID[458444]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	12.72	n.a.	PMID[458444]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	EC50	=	550.0	nM	PMID[458444]
NPT27	Others	Unspecified		CC50	=	7200.0	nM	PMID[458444]
NPT2	Others	Unspecified		Inhibition	=	83.1	%	PMID[458444]
NPT2	Others	Unspecified		Inhibition	=	91.4	%	PMID[458444]
NPT610	Others	Molecular identity unknown		FC	=	0.06	n.a.	PMID[458444]
NPT610	Others	Molecular identity unknown		FC	=	0.72	n.a.	PMID[458444]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	12.0	mm	PMID[458445]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	11.0	mm	PMID[458445]

☑ 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 NPC69360 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	284
0.1-0.2	1277
0.2-0.3	4937
0.3-0.4	12249
0.4-0.5	6546
0.5-0.6	11482
0.6-0.7	4803
0.7-0.8	1043
0.8-0.85	58
0.85-0.9	12
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC54125
0.9481	High Similarity	NPC89199
0.9423	High Similarity	NPC182257
0.9359	High Similarity	NPC304846
0.9241	High Similarity	NPC474953
0.9006	High Similarity	NPC110374
0.9006	High Similarity	NPC289743
0.8896	High Similarity	NPC115343
0.8896	High Similarity	NPC1291
0.8851	High Similarity	NPC77572
0.8848	High Similarity	NPC474607
0.8795	High Similarity	NPC474650
0.8675	High Similarity	NPC475794
0.8333	Intermediate Similarity	NPC4304
0.8314	Intermediate Similarity	NPC475919
0.8314	Intermediate Similarity	NPC474661
0.8303	Intermediate Similarity	NPC190332
0.8303	Intermediate Similarity	NPC181653
0.8224	Intermediate Similarity	NPC254610
0.8204	Intermediate Similarity	NPC474475
0.8193	Intermediate Similarity	NPC100566
0.8155	Intermediate Similarity	NPC470739
0.8155	Intermediate Similarity	NPC225597
0.8155	Intermediate Similarity	NPC477640
0.8144	Intermediate Similarity	NPC475686
0.8144	Intermediate Similarity	NPC58766
0.8133	Intermediate Similarity	NPC476002
0.8121	Intermediate Similarity	NPC320104
0.8084	Intermediate Similarity	NPC252960
0.8059	Intermediate Similarity	NPC187678
0.8036	Intermediate Similarity	NPC290759
0.8036	Intermediate Similarity	NPC266176
0.8036	Intermediate Similarity	NPC82533
0.8036	Intermediate Similarity	NPC158148
0.8024	Intermediate Similarity	NPC198741
0.8012	Intermediate Similarity	NPC218614
0.8012	Intermediate Similarity	NPC237044
0.8	Intermediate Similarity	NPC2314
0.8	Intermediate Similarity	NPC474051
0.7988	Intermediate Similarity	NPC311991
0.7965	Intermediate Similarity	NPC474325
0.7953	Intermediate Similarity	NPC304675
0.7919	Intermediate Similarity	NPC474745
0.7892	Intermediate Similarity	NPC205167
0.7892	Intermediate Similarity	NPC97072
0.7892	Intermediate Similarity	NPC249274
0.7892	Intermediate Similarity	NPC215829
0.7886	Intermediate Similarity	NPC474746
0.7886	Intermediate Similarity	NPC475981
0.7861	Intermediate Similarity	NPC15919
0.7857	Intermediate Similarity	NPC180306
0.7849	Intermediate Similarity	NPC49353
0.7838	Intermediate Similarity	NPC475768
0.7831	Intermediate Similarity	NPC59028
0.7831	Intermediate Similarity	NPC92191
0.7816	Intermediate Similarity	NPC244554
0.7803	Intermediate Similarity	NPC474470
0.7751	Intermediate Similarity	NPC247972
0.7733	Intermediate Similarity	NPC57272
0.7727	Intermediate Similarity	NPC248642
0.7697	Intermediate Similarity	NPC230098
0.7688	Intermediate Similarity	NPC228040
0.7684	Intermediate Similarity	NPC156576
0.7679	Intermediate Similarity	NPC165797
0.7661	Intermediate Similarity	NPC298186
0.7661	Intermediate Similarity	NPC301189
0.7661	Intermediate Similarity	NPC474324
0.7661	Intermediate Similarity	NPC57812
0.7657	Intermediate Similarity	NPC118633
0.7657	Intermediate Similarity	NPC148693
0.7657	Intermediate Similarity	NPC294790
0.7647	Intermediate Similarity	NPC470706
0.7643	Intermediate Similarity	NPC312770
0.7643	Intermediate Similarity	NPC14600
0.7643	Intermediate Similarity	NPC204848
0.7643	Intermediate Similarity	NPC160607
0.7643	Intermediate Similarity	NPC41473
0.764	Intermediate Similarity	NPC9867
0.763	Intermediate Similarity	NPC231371
0.763	Intermediate Similarity	NPC477115
0.7625	Intermediate Similarity	NPC178466
0.7625	Intermediate Similarity	NPC63628
0.7619	Intermediate Similarity	NPC329837
0.7619	Intermediate Similarity	NPC111485
0.7616	Intermediate Similarity	NPC475845
0.7614	Intermediate Similarity	NPC99179
0.7614	Intermediate Similarity	NPC126284
0.7605	Intermediate Similarity	NPC160931
0.7605	Intermediate Similarity	NPC147091
0.7605	Intermediate Similarity	NPC37205
0.7602	Intermediate Similarity	NPC68328
0.76	Intermediate Similarity	NPC283999
0.7595	Intermediate Similarity	NPC299583
0.7582	Intermediate Similarity	NPC469977
0.7572	Intermediate Similarity	NPC75958
0.7572	Intermediate Similarity	NPC474708
0.7561	Intermediate Similarity	NPC77359
0.7557	Intermediate Similarity	NPC114364
0.7557	Intermediate Similarity	NPC320223
0.7546	Intermediate Similarity	NPC16436
0.7545	Intermediate Similarity	NPC78733
0.7544	Intermediate Similarity	NPC232514
0.7544	Intermediate Similarity	NPC276944
0.7544	Intermediate Similarity	NPC238530
0.7543	Intermediate Similarity	NPC128560
0.7543	Intermediate Similarity	NPC229166
0.7543	Intermediate Similarity	NPC199465
0.7541	Intermediate Similarity	NPC33256
0.753	Intermediate Similarity	NPC270811
0.753	Intermediate Similarity	NPC148898
0.753	Intermediate Similarity	NPC471073
0.7529	Intermediate Similarity	NPC65403
0.7528	Intermediate Similarity	NPC476575
0.7528	Intermediate Similarity	NPC275132
0.7516	Intermediate Similarity	NPC264956
0.7515	Intermediate Similarity	NPC274026
0.75	Intermediate Similarity	NPC471032
0.75	Intermediate Similarity	NPC470935
0.75	Intermediate Similarity	NPC475959
0.75	Intermediate Similarity	NPC214116
0.7485	Intermediate Similarity	NPC189782
0.7484	Intermediate Similarity	NPC476570
0.747	Intermediate Similarity	NPC474560
0.747	Intermediate Similarity	NPC476568
0.7468	Intermediate Similarity	NPC246974
0.7468	Intermediate Similarity	NPC147247
0.7468	Intermediate Similarity	NPC174191
0.7459	Intermediate Similarity	NPC296742
0.7459	Intermediate Similarity	NPC112676
0.7451	Intermediate Similarity	NPC473960
0.7447	Intermediate Similarity	NPC159101
0.7444	Intermediate Similarity	NPC34780
0.7444	Intermediate Similarity	NPC69213
0.7439	Intermediate Similarity	NPC277857
0.7439	Intermediate Similarity	NPC115144
0.7438	Intermediate Similarity	NPC477837
0.7438	Intermediate Similarity	NPC477838
0.743	Intermediate Similarity	NPC233718
0.7425	Intermediate Similarity	NPC82285
0.7425	Intermediate Similarity	NPC223124
0.7425	Intermediate Similarity	NPC18614
0.7425	Intermediate Similarity	NPC133011
0.7423	Intermediate Similarity	NPC313414
0.7423	Intermediate Similarity	NPC5462
0.7421	Intermediate Similarity	NPC474595
0.7414	Intermediate Similarity	NPC66573
0.7414	Intermediate Similarity	NPC160570
0.7403	Intermediate Similarity	NPC157740
0.7403	Intermediate Similarity	NPC99798
0.7403	Intermediate Similarity	NPC191302
0.7403	Intermediate Similarity	NPC224293
0.7399	Intermediate Similarity	NPC124657
0.7394	Intermediate Similarity	NPC59907
0.7394	Intermediate Similarity	NPC37144
0.7391	Intermediate Similarity	NPC29472
0.7391	Intermediate Similarity	NPC275150
0.7389	Intermediate Similarity	NPC104077
0.7389	Intermediate Similarity	NPC219671
0.7389	Intermediate Similarity	NPC259742
0.7389	Intermediate Similarity	NPC97316
0.7389	Intermediate Similarity	NPC135772
0.7389	Intermediate Similarity	NPC147616
0.7389	Intermediate Similarity	NPC106739
0.7389	Intermediate Similarity	NPC471505
0.7381	Intermediate Similarity	NPC10875
0.7381	Intermediate Similarity	NPC10730
0.7375	Intermediate Similarity	NPC474039
0.7374	Intermediate Similarity	NPC476574
0.7374	Intermediate Similarity	NPC312918
0.7374	Intermediate Similarity	NPC477561
0.7374	Intermediate Similarity	NPC155442
0.7372	Intermediate Similarity	NPC329595
0.7372	Intermediate Similarity	NPC326599
0.7365	Intermediate Similarity	NPC127402
0.7365	Intermediate Similarity	NPC52475
0.7358	Intermediate Similarity	NPC7018
0.7358	Intermediate Similarity	NPC101624
0.7358	Intermediate Similarity	NPC18576
0.7358	Intermediate Similarity	NPC184938
0.7356	Intermediate Similarity	NPC150879
0.7356	Intermediate Similarity	NPC247389
0.7353	Intermediate Similarity	NPC78359
0.7353	Intermediate Similarity	NPC40389
0.7353	Intermediate Similarity	NPC148014
0.7353	Intermediate Similarity	NPC315707
0.7353	Intermediate Similarity	NPC65490
0.7349	Intermediate Similarity	NPC182119
0.7346	Intermediate Similarity	NPC472711
0.7345	Intermediate Similarity	NPC477558
0.7342	Intermediate Similarity	NPC218530
0.7342	Intermediate Similarity	NPC58585
0.7341	Intermediate Similarity	NPC167546
0.7341	Intermediate Similarity	NPC16805
0.7341	Intermediate Similarity	NPC302527
0.7338	Intermediate Similarity	NPC251466
0.7338	Intermediate Similarity	NPC156944
0.7337	Intermediate Similarity	NPC117717
0.7337	Intermediate Similarity	NPC138487
0.7337	Intermediate Similarity	NPC94499
0.7337	Intermediate Similarity	NPC216459

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 NPC69360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	624
0.2-0.3	1158
0.3-0.4	2498
0.4-0.5	2450
0.5-0.6	1558
0.6-0.7	589
0.7-0.8	96
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8354	Intermediate Similarity	NPD4005	Discontinued
0.7711	Intermediate Similarity	NPD2978	Approved
0.7711	Intermediate Similarity	NPD2977	Approved
0.7711	Intermediate Similarity	NPD5773	Approved
0.7711	Intermediate Similarity	NPD5772	Approved
0.7701	Intermediate Similarity	NPD7007	Discovery
0.7679	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1375	Discontinued
0.7625	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD52	Approved
0.75	Intermediate Similarity	NPD7526	Approved
0.75	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD2970	Approved
0.7457	Intermediate Similarity	NPD2969	Approved
0.7439	Intermediate Similarity	NPD4123	Phase 3
0.7407	Intermediate Similarity	NPD6331	Phase 2
0.7368	Intermediate Similarity	NPD5604	Discontinued
0.7362	Intermediate Similarity	NPD5241	Discontinued
0.7353	Intermediate Similarity	NPD2560	Approved
0.7353	Intermediate Similarity	NPD2563	Approved
0.7346	Intermediate Similarity	NPD4237	Approved
0.7346	Intermediate Similarity	NPD4236	Phase 3
0.7325	Intermediate Similarity	NPD2674	Phase 3
0.7321	Intermediate Similarity	NPD4675	Approved
0.7321	Intermediate Similarity	NPD4678	Approved
0.7314	Intermediate Similarity	NPD27	Approved
0.7314	Intermediate Similarity	NPD2489	Approved
0.7308	Intermediate Similarity	NPD6843	Phase 3
0.7308	Intermediate Similarity	NPD6842	Approved
0.7308	Intermediate Similarity	NPD6841	Approved
0.7299	Intermediate Similarity	NPD3051	Approved
0.7267	Intermediate Similarity	NPD2161	Phase 2
0.7253	Intermediate Similarity	NPD4663	Approved
0.7237	Intermediate Similarity	NPD3705	Approved
0.7229	Intermediate Similarity	NPD4739	Approved
0.7215	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7906	Approved
0.72	Intermediate Similarity	NPD6071	Discontinued
0.7182	Intermediate Similarity	NPD7313	Approved
0.7182	Intermediate Similarity	NPD4578	Approved
0.7182	Intermediate Similarity	NPD4577	Approved
0.7182	Intermediate Similarity	NPD7312	Approved
0.7182	Intermediate Similarity	NPD7311	Approved
0.7182	Intermediate Similarity	NPD7310	Approved
0.7176	Intermediate Similarity	NPD4773	Phase 2
0.7176	Intermediate Similarity	NPD4772	Phase 2
0.7168	Intermediate Similarity	NPD4055	Discovery
0.7152	Intermediate Similarity	NPD3145	Approved
0.7152	Intermediate Similarity	NPD3144	Approved
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7309	Approved
0.7143	Intermediate Similarity	NPD2122	Discontinued
0.7108	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4108	Discontinued
0.7097	Intermediate Similarity	NPD7296	Approved
0.7093	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5089	Approved
0.7076	Intermediate Similarity	NPD5090	Approved
0.7073	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7827	Phase 1
0.7048	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3692	Discontinued
0.703	Intermediate Similarity	NPD3060	Approved
0.7022	Intermediate Similarity	NPD4481	Phase 3
0.7012	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7153	Discontinued
0.6957	Remote Similarity	NPD2238	Phase 2
0.6936	Remote Similarity	NPD37	Approved
0.6936	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1357	Approved
0.6923	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4584	Approved
0.6923	Remote Similarity	NPD9622	Approved
0.6901	Remote Similarity	NPD3686	Approved
0.6901	Remote Similarity	NPD3687	Approved
0.6897	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD839	Approved
0.6894	Remote Similarity	NPD840	Approved
0.6889	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3027	Phase 3
0.6871	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2677	Approved
0.6845	Remote Similarity	NPD2219	Phase 1
0.6826	Remote Similarity	NPD6674	Discontinued
0.6826	Remote Similarity	NPD5177	Phase 3
0.6826	Remote Similarity	NPD4162	Approved
0.6823	Remote Similarity	NPD4420	Approved
0.6818	Remote Similarity	NPD4966	Approved
0.6818	Remote Similarity	NPD4967	Phase 2
0.6818	Remote Similarity	NPD4965	Approved
0.6815	Remote Similarity	NPD1669	Approved
0.6815	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD600	Approved
0.6813	Remote Similarity	NPD596	Approved
0.6809	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5582	Discontinued
0.6804	Remote Similarity	NPD3450	Approved
0.6804	Remote Similarity	NPD3452	Approved
0.6802	Remote Similarity	NPD4210	Discontinued
0.679	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD9381	Approved
0.6774	Remote Similarity	NPD8053	Approved
0.6774	Remote Similarity	NPD8054	Approved
0.6774	Remote Similarity	NPD9384	Approved
0.6769	Remote Similarity	NPD5006	Approved
0.6769	Remote Similarity	NPD5005	Approved
0.6768	Remote Similarity	NPD823	Approved
0.6768	Remote Similarity	NPD817	Approved
0.6765	Remote Similarity	NPD4357	Discontinued
0.6761	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6107	Approved
0.675	Remote Similarity	NPD1712	Approved
0.6748	Remote Similarity	NPD1613	Approved
0.6748	Remote Similarity	NPD1558	Phase 1
0.6748	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6234	Discontinued
0.674	Remote Similarity	NPD2898	Approved
0.6739	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5109	Approved
0.6728	Remote Similarity	NPD5110	Phase 2
0.6728	Remote Similarity	NPD5111	Phase 2
0.6725	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7315	Approved
0.6722	Remote Similarity	NPD4010	Discontinued
0.6718	Remote Similarity	NPD2493	Approved
0.6718	Remote Similarity	NPD2494	Approved
0.6688	Remote Similarity	NPD776	Approved
0.6687	Remote Similarity	NPD1130	Approved
0.6687	Remote Similarity	NPD558	Phase 2
0.6687	Remote Similarity	NPD1132	Approved
0.6687	Remote Similarity	NPD1136	Approved
0.6686	Remote Similarity	NPD6072	Discontinued
0.6684	Remote Similarity	NPD2974	Approved
0.6684	Remote Similarity	NPD2975	Approved
0.6684	Remote Similarity	NPD2973	Approved
0.6667	Remote Similarity	NPD2157	Approved
0.6667	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1774	Approved
0.665	Remote Similarity	NPD4004	Approved
0.665	Remote Similarity	NPD4002	Approved
0.6647	Remote Similarity	NPD9570	Approved
0.6647	Remote Similarity	NPD3640	Phase 3
0.6647	Remote Similarity	NPD3641	Approved
0.6647	Remote Similarity	NPD3639	Approved
0.6646	Remote Similarity	NPD3620	Phase 2
0.6646	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD7281	Phase 3
0.6631	Remote Similarity	NPD7280	Phase 3
0.663	Remote Similarity	NPD8156	Discontinued
0.663	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD601	Approved
0.6626	Remote Similarity	NPD597	Approved
0.6626	Remote Similarity	NPD598	Approved
0.6616	Remote Similarity	NPD4582	Approved
0.6616	Remote Similarity	NPD4583	Approved
0.6614	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD4666	Phase 3
0.6611	Remote Similarity	NPD6746	Phase 2
0.6609	Remote Similarity	NPD1653	Approved
0.6604	Remote Similarity	NPD3685	Discontinued
0.6597	Remote Similarity	NPD2488	Approved
0.6597	Remote Similarity	NPD2490	Approved
0.6593	Remote Similarity	NPD4083	Discontinued
0.6592	Remote Similarity	NPD7833	Phase 2
0.6592	Remote Similarity	NPD7831	Phase 2
0.6592	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3778	Approved
0.659	Remote Similarity	NPD1349	Approved
0.659	Remote Similarity	NPD1351	Approved
0.659	Remote Similarity	NPD1350	Approved
0.6587	Remote Similarity	NPD1753	Discontinued
0.6584	Remote Similarity	NPD9621	Approved
0.6584	Remote Similarity	NPD9620	Approved
0.6584	Remote Similarity	NPD9619	Approved
0.6582	Remote Similarity	NPD4580	Approved
0.6582	Remote Similarity	NPD1091	Approved
0.658	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3349	Phase 2
0.6579	Remote Similarity	NPD4157	Discontinued
0.6576	Remote Similarity	NPD8251	Approved
0.6576	Remote Similarity	NPD3909	Discontinued
0.6576	Remote Similarity	NPD8252	Approved
0.6576	Remote Similarity	NPD7228	Approved
0.6576	Remote Similarity	NPD8099	Discontinued
0.6571	Remote Similarity	NPD4017	Approved
0.6566	Remote Similarity	NPD2492	Phase 1
0.6564	Remote Similarity	NPD1024	Discontinued
0.6562	Remote Similarity	NPD3634	Approved
0.6562	Remote Similarity	NPD3633	Approved
0.6562	Remote Similarity	NPD2922	Phase 1
0.6556	Remote Similarity	NPD5709	Phase 3
0.6554	Remote Similarity	NPD3383	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