NPASS Compound

Structure

CID4108 OpenBabel06191715322D 36 40 0 0 1 0 0 0 0 0999 V2000 5.0610 -0.9102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1976 2.8452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0264 -3.4710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3316 3.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0602 -1.3455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3693 -0.3944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0821 -1.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3031 0.9568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9039 0.1573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7001 0.3487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4130 -0.8102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3997 1.3855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0659 -2.7492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0861 -2.5492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0529 0.8840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0643 -0.8297 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3316 2.3452 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7220 0.1408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4005 1.3452 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0747 0.6761 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3316 1.3452 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7476 -1.7783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4005 2.3452 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3266 -0.1330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0805 -0.9968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0264 -2.4710 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5345 2.8452 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5345 0.8452 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6680 -0.2375 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5928 -2.3127 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9957 -0.8761 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0675 -1.1572 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8924 -2.9710 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3115 -1.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4005 3.3452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 17 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 9 1 0 0 0 0 8 12 2 0 0 0 0 9 16 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 14 2 0 0 0 0 13 26 1 0 0 0 0 14 34 1 0 0 0 0 15 18 1 0 0 0 0 16 1 1 6 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 17 27 1 6 0 0 0 19 23 1 0 0 0 0 19 28 1 6 0 0 0 20 15 1 1 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 28 1 6 0 0 0 22 26 1 0 0 0 0 22 30 2 0 0 0 0 23 27 1 1 0 0 0 23 35 1 0 0 0 0 24 29 2 0 0 0 0 24 31 1 0 0 0 0 25 32 2 0 0 0 0 25 34 1 0 0 0 0 25 36 1 0 0 0 0 26 3 1 1 0 0 0 26 33 1 0 0 0 0 27 4 1 6 0 0 0 27 35 1 0 0 0 0 28 24 1 6 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	495.23
Volume:	501.498
LogP:	3.049
LogD:	3.288
LogS:	-4.021
# Rotatable Bonds:	2
TPSA:	114.46
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	6.093
Fsp3:	0.536
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.662
MDCK Permeability:	4.546814307104796e-05
Pgp-inhibitor:	0.198
Pgp-substrate:	0.191
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.839
Plasma Protein Binding (PPB):	88.34115600585938%
Volume Distribution (VD):	0.823
Pgp-substrate:	13.349326133728027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.216
CYP2C19-inhibitor:	0.399
CYP2C19-substrate:	0.512
CYP2C9-inhibitor:	0.151
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.117
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.952
CYP3A4-substrate:	0.646

ADMET: Excretion

Clearance (CL):	9.391
Half-life (T1/2):	0.285

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.717
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.638
Skin Sensitization:	0.474
Carcinogencity:	0.545
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC4108

Natural Product ID:	NPC4108
*Common Name:**	Cytochalasin E
IUPAC Name:	n.a.
Synonyms:	Cytochalasin E
Standard InCHIKey:	LAJXCUNOQSHRJO-ZYGJITOWSA-N
Standard InCHI:	InChI=1S/C28H33NO7/c1-16-9-8-12-19-23-27(4,35-23)17(2)21-20(15-18-10-6-5-7-11-18)29-24(31)28(19,21)36-25(32)34-14-13-26(3,33)22(16)30/h5-8,10-14,16-17,19-21,23,33H,9,15H2,1-4H3,(H,29,31)/b12-8+,14-13+/t16-,17-,19-,20-,21-,23-,26+,27+,28+/m0/s1
SMILES:	O=C1O/C=C/[C@@](C)(O)C(=O)[C@H](C/C=C/[C@@H]2[C@]3(O1)C(=N[C@H]([C@@H]3[C@H](C)[C@@]1([C@H]2O1)C)Cc1ccccc1)O)C
Synthetic Gene Cluster:	BGC0000983;
ChEMBL Identifier:	CHEMBL494856
PubChem CID:	5458385
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001821] Cytochalasans

*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
NPO40320	Rhinocladiella sp.	Species	Herpotrichiellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141120]
NPO33507	spicaria elegans	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16792402]
NPO33507	spicaria elegans	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18507474]
NPO19108	Arthrinium sacchari	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718054]
NPO19108	Arthrinium sacchari	Species	Apiosporaceae	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	70
IC50	4
Others	6

Activity Type	# Activity
Cell Line	75
Individual Protein	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	93.0	nM	PMID[514143]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6.2	nM	PMID[514143]
NPT323	Cell Line	SW-620	Homo sapiens	IC100	=	0.977	ug ml-1	PMID[514144]
NPT393	Cell Line	HCT-116	Homo sapiens	IC100	=	0.244	ug ml-1	PMID[514144]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	11.4	nM	PMID[514145]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	23.07	nM	PMID[514146]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	3162.28	nM	PMID[514146]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	197.24	nM	PMID[514146]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	10.0	nM	PMID[514146]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	19.91	nM	PMID[514146]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	23.93	nM	PMID[514146]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	83.75	nM	PMID[514146]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	16.9	nM	PMID[514146]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	10.0	nM	PMID[514146]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	21.13	nM	PMID[514146]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	25.12	nM	PMID[514146]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	1721.87	nM	PMID[514146]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	18.11	nM	PMID[514146]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	97.5	nM	PMID[514146]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	8590.14	nM	PMID[514146]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	20.56	nM	PMID[514146]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	5688.53	nM	PMID[514146]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	18.79	nM	PMID[514146]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	23550.49	nM	PMID[514146]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	11297.96	nM	PMID[514146]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	60.39	nM	PMID[514146]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	90.99	nM	PMID[514146]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	10.0	nM	PMID[514146]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	65.01	nM	PMID[514146]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	75.86	nM	PMID[514146]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	10.0	nM	PMID[514146]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	21777.1	nM	PMID[514146]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	43.15	nM	PMID[514146]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	17498.47	nM	PMID[514146]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	43.65	nM	PMID[514146]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	18.28	nM	PMID[514146]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	559.76	nM	PMID[514146]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	555.9	nM	PMID[514146]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	26.18	nM	PMID[514146]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	39.17	nM	PMID[514146]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	12.82	nM	PMID[514146]
NPT168	Cell Line	P388	Mus musculus	GI50	n.a.	16.6	nM	PMID[514146]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	392.64	nM	PMID[514146]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	24.77	nM	PMID[514146]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	25.29	nM	PMID[514146]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	10.19	nM	PMID[514146]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	138.36	nM	PMID[514146]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	83.37	nM	PMID[514146]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	50.0	nM	PMID[514146]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	63.83	nM	PMID[514146]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	74.99	nM	PMID[514146]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	29.17	nM	PMID[514146]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	14.09	nM	PMID[514146]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	54.83	nM	PMID[514146]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	29.17	nM	PMID[514146]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100.0	nM	PMID[514146]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	16.07	nM	PMID[514146]
NPT552	Cell Line	P388/ADR	Mus musculus	GI50	n.a.	314.05	nM	PMID[514146]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	13.21	nM	PMID[514146]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	18879.91	nM	PMID[514146]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	53.58	nM	PMID[514146]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	41.88	nM	PMID[514146]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	17.06	nM	PMID[514146]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	114.02	nM	PMID[514146]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	18.92	nM	PMID[514146]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	263.03	nM	PMID[514146]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	20.99	nM	PMID[514146]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	10.33	nM	PMID[514146]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	33.27	nM	PMID[514146]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	19.45	nM	PMID[514146]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	200.45	nM	PMID[514146]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	16.07	nM	PMID[514146]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	11.07	nM	PMID[514146]
NPT738	Cell Line	SN12K1	Homo sapiens	GI50	n.a.	10.0	nM	PMID[514146]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	17.1	nM	PMID[514146]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	5.91	%	PMID[514148]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC100	<	0.0153	ug ml-1	PMID[514144]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11.0	nM	PMID[514145]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	190.0	%	PMID[514147]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	9.25	%	PMID[514148]

☑ 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 NPC4108 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	183
0.1-0.2	821
0.2-0.3	2082
0.3-0.4	7043
0.4-0.5	17129
0.5-0.6	14519
0.6-0.7	872
0.7-0.8	28
0.8-0.85	8
0.85-0.9	8
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9161	High Similarity	NPC49565
0.8936	High Similarity	NPC175870
0.8784	High Similarity	NPC201692
0.8776	High Similarity	NPC173934
0.8767	High Similarity	NPC262216
0.859	High Similarity	NPC15506
0.8581	High Similarity	NPC237240
0.8581	High Similarity	NPC31171
0.8562	High Similarity	NPC477115
0.8531	High Similarity	NPC228511
0.8472	Intermediate Similarity	NPC279045
0.8472	Intermediate Similarity	NPC113325
0.844	Intermediate Similarity	NPC295478
0.8367	Intermediate Similarity	NPC239770
0.8264	Intermediate Similarity	NPC42423
0.8188	Intermediate Similarity	NPC111586
0.8188	Intermediate Similarity	NPC261709
0.8188	Intermediate Similarity	NPC108852
0.805	Intermediate Similarity	NPC156348
0.8042	Intermediate Similarity	NPC278097
0.8027	Intermediate Similarity	NPC90693
0.8027	Intermediate Similarity	NPC64897
0.7931	Intermediate Similarity	NPC71271
0.7724	Intermediate Similarity	NPC472414
0.7586	Intermediate Similarity	NPC472415
0.7467	Intermediate Similarity	NPC183722
0.7226	Intermediate Similarity	NPC208725
0.7212	Intermediate Similarity	NPC217801
0.7126	Intermediate Similarity	NPC235460
0.7102	Intermediate Similarity	NPC475345
0.7097	Intermediate Similarity	NPC477680
0.7086	Intermediate Similarity	NPC203005
0.7062	Intermediate Similarity	NPC475649
0.7024	Intermediate Similarity	NPC476194
0.7022	Intermediate Similarity	NPC474607
0.7011	Intermediate Similarity	NPC120667
0.7011	Intermediate Similarity	NPC278272
0.6993	Remote Similarity	NPC472413
0.6989	Remote Similarity	NPC476113
0.6983	Remote Similarity	NPC474650
0.6966	Remote Similarity	NPC475794
0.6933	Remote Similarity	NPC473889
0.6905	Remote Similarity	NPC212699
0.6905	Remote Similarity	NPC207675
0.689	Remote Similarity	NPC94602
0.6887	Remote Similarity	NPC108286
0.6887	Remote Similarity	NPC473870
0.6887	Remote Similarity	NPC473871
0.6885	Remote Similarity	NPC317882
0.6885	Remote Similarity	NPC473300
0.6885	Remote Similarity	NPC453583
0.6885	Remote Similarity	NPC475336
0.6885	Remote Similarity	NPC471754
0.6883	Remote Similarity	NPC116057
0.6871	Remote Similarity	NPC260194
0.6868	Remote Similarity	NPC471395
0.6868	Remote Similarity	NPC327699
0.6867	Remote Similarity	NPC472761
0.6862	Remote Similarity	NPC472375
0.6862	Remote Similarity	NPC472392
0.6859	Remote Similarity	NPC476977
0.6848	Remote Similarity	NPC33372
0.6848	Remote Similarity	NPC67246
0.6839	Remote Similarity	NPC93632
0.6831	Remote Similarity	NPC471623
0.6826	Remote Similarity	NPC275839
0.6825	Remote Similarity	NPC472391
0.6815	Remote Similarity	NPC476976
0.6807	Remote Similarity	NPC476744
0.6793	Remote Similarity	NPC324251
0.6793	Remote Similarity	NPC275170
0.6793	Remote Similarity	NPC206211
0.6793	Remote Similarity	NPC306001
0.6793	Remote Similarity	NPC471629
0.6793	Remote Similarity	NPC473400
0.679	Remote Similarity	NPC325078
0.6788	Remote Similarity	NPC227905
0.6788	Remote Similarity	NPC339338
0.6788	Remote Similarity	NPC146097
0.6779	Remote Similarity	NPC237420
0.6765	Remote Similarity	NPC154675
0.6754	Remote Similarity	NPC289383
0.6753	Remote Similarity	NPC476970
0.6753	Remote Similarity	NPC470158
0.6753	Remote Similarity	NPC475933
0.6747	Remote Similarity	NPC476743
0.6738	Remote Similarity	NPC242662
0.6738	Remote Similarity	NPC191193
0.6738	Remote Similarity	NPC215892
0.6738	Remote Similarity	NPC321072
0.6727	Remote Similarity	NPC313414
0.6725	Remote Similarity	NPC181924
0.6725	Remote Similarity	NPC471203
0.6723	Remote Similarity	NPC474953
0.6719	Remote Similarity	NPC116862
0.6712	Remote Similarity	NPC477246
0.6712	Remote Similarity	NPC477245
0.671	Remote Similarity	NPC476971
0.671	Remote Similarity	NPC476972
0.6707	Remote Similarity	NPC470274
0.6707	Remote Similarity	NPC185404
0.6705	Remote Similarity	NPC304846
0.6702	Remote Similarity	NPC181964
0.6702	Remote Similarity	NPC471606
0.6702	Remote Similarity	NPC208553
0.6689	Remote Similarity	NPC190663
0.6687	Remote Similarity	NPC475128
0.6686	Remote Similarity	NPC476741
0.6686	Remote Similarity	NPC49297
0.6685	Remote Similarity	NPC475919
0.6685	Remote Similarity	NPC474661
0.6667	Remote Similarity	NPC291759
0.6667	Remote Similarity	NPC476278
0.6667	Remote Similarity	NPC473490
0.6667	Remote Similarity	NPC473558
0.6667	Remote Similarity	NPC473860
0.6647	Remote Similarity	NPC146310
0.6646	Remote Similarity	NPC140021
0.6646	Remote Similarity	NPC305162
0.6645	Remote Similarity	NPC470816
0.663	Remote Similarity	NPC34780
0.6627	Remote Similarity	NPC62792
0.6627	Remote Similarity	NPC473541
0.6627	Remote Similarity	NPC478123
0.6627	Remote Similarity	NPC476742
0.6612	Remote Similarity	NPC133591
0.6608	Remote Similarity	NPC251139
0.6608	Remote Similarity	NPC471176
0.6606	Remote Similarity	NPC91703
0.6604	Remote Similarity	NPC80599
0.6601	Remote Similarity	NPC160493
0.6601	Remote Similarity	NPC475328
0.6592	Remote Similarity	NPC88378
0.6592	Remote Similarity	NPC211713
0.6591	Remote Similarity	NPC54125
0.6591	Remote Similarity	NPC89199
0.6587	Remote Similarity	NPC476757
0.6587	Remote Similarity	NPC132771
0.6584	Remote Similarity	NPC6570
0.6581	Remote Similarity	NPC473083
0.6579	Remote Similarity	NPC80150
0.6577	Remote Similarity	NPC188010
0.6571	Remote Similarity	NPC43304
0.6571	Remote Similarity	NPC477190
0.6571	Remote Similarity	NPC477188
0.6571	Remote Similarity	NPC275477
0.6566	Remote Similarity	NPC471912
0.6566	Remote Similarity	NPC328824
0.6566	Remote Similarity	NPC80895
0.6561	Remote Similarity	NPC58061
0.6561	Remote Similarity	NPC230331
0.6558	Remote Similarity	NPC35996
0.6556	Remote Similarity	NPC474051
0.6556	Remote Similarity	NPC314992
0.6556	Remote Similarity	NPC310467
0.6545	Remote Similarity	NPC472546
0.6543	Remote Similarity	NPC472545
0.6543	Remote Similarity	NPC477557
0.6543	Remote Similarity	NPC472551
0.6541	Remote Similarity	NPC246913
0.6538	Remote Similarity	NPC45821
0.6538	Remote Similarity	NPC473082
0.6536	Remote Similarity	NPC476281
0.6536	Remote Similarity	NPC311175
0.6536	Remote Similarity	NPC37641
0.6536	Remote Similarity	NPC476184
0.6533	Remote Similarity	NPC2265
0.6529	Remote Similarity	NPC298072
0.6527	Remote Similarity	NPC277053
0.6527	Remote Similarity	NPC301946
0.6524	Remote Similarity	NPC472547
0.6524	Remote Similarity	NPC469360
0.6524	Remote Similarity	NPC97667
0.6524	Remote Similarity	NPC171207
0.6524	Remote Similarity	NPC275592
0.6524	Remote Similarity	NPC100913
0.6516	Remote Similarity	NPC77691
0.6516	Remote Similarity	NPC470815
0.6513	Remote Similarity	NPC475768
0.651	Remote Similarity	NPC473869
0.6509	Remote Similarity	NPC473215
0.6503	Remote Similarity	NPC322526
0.6503	Remote Similarity	NPC39549
0.65	Remote Similarity	NPC245836
0.65	Remote Similarity	NPC233910
0.6494	Remote Similarity	NPC70973
0.6491	Remote Similarity	NPC22571
0.6491	Remote Similarity	NPC233581
0.6491	Remote Similarity	NPC469647
0.6491	Remote Similarity	NPC138641
0.6491	Remote Similarity	NPC283875
0.6491	Remote Similarity	NPC469648
0.6491	Remote Similarity	NPC145649
0.649	Remote Similarity	NPC169328
0.6486	Remote Similarity	NPC38823
0.6486	Remote Similarity	NPC207033
0.6485	Remote Similarity	NPC87448
0.6485	Remote Similarity	NPC41481
0.6485	Remote Similarity	NPC27377
0.6485	Remote Similarity	NPC97947

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 NPC4108 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	472
0.2-0.3	938
0.3-0.4	2615
0.4-0.5	3448
0.5-0.6	1364
0.6-0.7	177
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8581	High Similarity	NPD7274	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8407	Phase 2
0.6923	Remote Similarity	NPD8361	Approved
0.6923	Remote Similarity	NPD8360	Approved
0.691	Remote Similarity	NPD8368	Discontinued
0.6862	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD8435	Approved
0.6813	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2575	Approved
0.6733	Remote Similarity	NPD5981	Approved
0.6702	Remote Similarity	NPD8485	Approved
0.6667	Remote Similarity	NPD8265	Approved
0.6647	Remote Similarity	NPD8417	Discontinued
0.6609	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD5618	Discontinued
0.6582	Remote Similarity	NPD4738	Phase 2
0.6556	Remote Similarity	NPD2217	Approved
0.6556	Remote Similarity	NPD4479	Discontinued
0.6556	Remote Similarity	NPD2218	Phase 2
0.6543	Remote Similarity	NPD6852	Discontinued
0.6517	Remote Similarity	NPD8404	Phase 2
0.65	Remote Similarity	NPD4746	Phase 3
0.65	Remote Similarity	NPD3090	Approved
0.65	Remote Similarity	NPD2571	Approved
0.65	Remote Similarity	NPD3087	Approved
0.65	Remote Similarity	NPD3615	Approved
0.65	Remote Similarity	NPD3089	Approved
0.65	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2566	Approved
0.65	Remote Similarity	NPD3614	Approved
0.65	Remote Similarity	NPD2574	Discontinued
0.65	Remote Similarity	NPD2570	Approved
0.65	Remote Similarity	NPD2573	Approved
0.65	Remote Similarity	NPD4745	Approved
0.65	Remote Similarity	NPD3088	Approved
0.65	Remote Similarity	NPD3616	Approved
0.6474	Remote Similarity	NPD6325	Discontinued
0.6463	Remote Similarity	NPD3642	Approved
0.6463	Remote Similarity	NPD3644	Approved
0.6463	Remote Similarity	NPD3643	Approved
0.6461	Remote Similarity	NPD7315	Approved
0.645	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4621	Approved
0.6438	Remote Similarity	NPD4619	Approved
0.6432	Remote Similarity	NPD7801	Approved
0.642	Remote Similarity	NPD4685	Phase 3
0.642	Remote Similarity	NPD4686	Approved
0.642	Remote Similarity	NPD4684	Phase 3
0.6415	Remote Similarity	NPD2613	Approved
0.6398	Remote Similarity	NPD5036	Approved
0.6393	Remote Similarity	NPD7007	Discovery
0.6387	Remote Similarity	NPD4807	Approved
0.6387	Remote Similarity	NPD4806	Approved
0.6382	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD7874	Approved
0.6378	Remote Similarity	NPD5035	Approved
0.6373	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5305	Approved
0.6364	Remote Similarity	NPD5038	Approved
0.6364	Remote Similarity	NPD5037	Approved
0.6364	Remote Similarity	NPD5306	Approved
0.6358	Remote Similarity	NPD2238	Phase 2
0.6358	Remote Similarity	NPD6311	Approved
0.6358	Remote Similarity	NPD6310	Approved
0.6358	Remote Similarity	NPD6309	Approved
0.6352	Remote Similarity	NPD5204	Approved
0.6348	Remote Similarity	NPD6746	Phase 2
0.6343	Remote Similarity	NPD7972	Discontinued
0.6329	Remote Similarity	NPD2625	Approved
0.6329	Remote Similarity	NPD2626	Approved
0.6329	Remote Similarity	NPD2628	Approved
0.6329	Remote Similarity	NPD2160	Approved
0.6329	Remote Similarity	NPD2627	Approved
0.6329	Remote Similarity	NPD2159	Approved
0.6325	Remote Similarity	NPD1375	Discontinued
0.6324	Remote Similarity	NPD5032	Approved
0.6322	Remote Similarity	NPD6072	Discontinued
0.6316	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7296	Approved
0.6312	Remote Similarity	NPD4620	Approved
0.6312	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD5201	Approved
0.6312	Remote Similarity	NPD5203	Approved
0.6312	Remote Similarity	NPD4617	Approved
0.631	Remote Similarity	NPD3400	Discontinued
0.6304	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4583	Approved
0.6294	Remote Similarity	NPD4582	Approved
0.6289	Remote Similarity	NPD7565	Approved
0.6276	Remote Similarity	NPD6823	Phase 2
0.6272	Remote Similarity	NPD8323	Discontinued
0.627	Remote Similarity	NPD5030	Phase 2
0.627	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD5121	Approved
0.6258	Remote Similarity	NPD5126	Approved
0.6258	Remote Similarity	NPD5125	Phase 3
0.6258	Remote Similarity	NPD5119	Approved
0.6258	Remote Similarity	NPD5120	Approved
0.6258	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD4666	Phase 3
0.6256	Remote Similarity	NPD4580	Approved
0.625	Remote Similarity	NPD3661	Approved
0.625	Remote Similarity	NPD3662	Phase 3
0.625	Remote Similarity	NPD6535	Approved
0.625	Remote Similarity	NPD3663	Approved
0.625	Remote Similarity	NPD6534	Approved
0.625	Remote Similarity	NPD3664	Approved
0.625	Remote Similarity	NPD5557	Phase 1
0.6244	Remote Similarity	NPD4002	Approved
0.6244	Remote Similarity	NPD4004	Approved
0.6242	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD8462	Phase 1
0.6237	Remote Similarity	NPD4954	Approved
0.6237	Remote Similarity	NPD7699	Phase 2
0.6237	Remote Similarity	NPD5034	Approved
0.6237	Remote Similarity	NPD4955	Approved
0.6237	Remote Similarity	NPD36	Approved
0.6237	Remote Similarity	NPD5028	Approved
0.6237	Remote Similarity	NPD5026	Approved
0.6237	Remote Similarity	NPD7700	Phase 2
0.6235	Remote Similarity	NPD6667	Approved
0.6235	Remote Similarity	NPD6666	Approved
0.623	Remote Similarity	NPD3909	Discontinued
0.6229	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD2494	Approved
0.6224	Remote Similarity	NPD2493	Approved
0.6218	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4136	Approved
0.6218	Remote Similarity	NPD4135	Approved
0.6218	Remote Similarity	NPD4106	Approved
0.6213	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD8319	Approved
0.6212	Remote Similarity	NPD8320	Phase 1
0.6211	Remote Similarity	NPD6836	Approved
0.6203	Remote Similarity	NPD7313	Approved
0.6203	Remote Similarity	NPD7312	Approved
0.6203	Remote Similarity	NPD7310	Approved
0.6203	Remote Similarity	NPD7311	Approved
0.6201	Remote Similarity	NPD5709	Phase 3
0.6186	Remote Similarity	NPD2975	Approved
0.6186	Remote Similarity	NPD2974	Approved
0.6186	Remote Similarity	NPD2973	Approved
0.6184	Remote Similarity	NPD2629	Approved
0.6183	Remote Similarity	NPD5031	Approved
0.6183	Remote Similarity	NPD5027	Approved
0.6183	Remote Similarity	NPD5039	Approved
0.6183	Remote Similarity	NPD5029	Approved
0.6178	Remote Similarity	NPD3529	Phase 2
0.6178	Remote Similarity	NPD2608	Approved
0.6178	Remote Similarity	NPD4218	Approved
0.6178	Remote Similarity	NPD4215	Approved
0.6178	Remote Similarity	NPD3131	Approved
0.6178	Remote Similarity	NPD2609	Approved
0.6178	Remote Similarity	NPD4217	Approved
0.6178	Remote Similarity	NPD3132	Approved
0.6178	Remote Similarity	NPD2612	Approved
0.6178	Remote Similarity	NPD2610	Approved
0.6178	Remote Similarity	NPD2611	Approved
0.6178	Remote Similarity	NPD4216	Approved
0.6173	Remote Similarity	NPD6782	Approved
0.6173	Remote Similarity	NPD6781	Approved
0.6173	Remote Similarity	NPD6777	Approved
0.6173	Remote Similarity	NPD6778	Approved
0.6173	Remote Similarity	NPD6779	Approved
0.6173	Remote Similarity	NPD6780	Approved
0.6173	Remote Similarity	NPD6776	Approved
0.617	Remote Similarity	NPD7309	Approved
0.617	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD7522	Discontinued
0.6168	Remote Similarity	NPD2161	Phase 2
0.6162	Remote Similarity	NPD7497	Discontinued
0.6158	Remote Similarity	NPD6843	Phase 3
0.6158	Remote Similarity	NPD5772	Approved
0.6158	Remote Similarity	NPD7827	Phase 1
0.6158	Remote Similarity	NPD6842	Approved
0.6158	Remote Similarity	NPD5773	Approved
0.6158	Remote Similarity	NPD7906	Approved
0.6158	Remote Similarity	NPD6841	Approved
0.6149	Remote Similarity	NPD6406	Approved
0.6142	Remote Similarity	NPD3452	Approved
0.6142	Remote Similarity	NPD3450	Approved
0.6138	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD7526	Approved
0.6127	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD7613	Discontinued
0.6127	Remote Similarity	NPD52	Approved
0.6119	Remote Similarity	NPD7701	Phase 2
0.6118	Remote Similarity	NPD6676	Phase 2
0.6117	Remote Similarity	NPD4577	Approved
0.6117	Remote Similarity	NPD4578	Approved
0.6114	Remote Similarity	NPD4005	Discontinued
0.6108	Remote Similarity	NPD4108	Discontinued
0.6105	Remote Similarity	NPD4663	Approved
0.6103	Remote Similarity	NPD7282	Approved
0.61	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7999	Approved
0.6098	Remote Similarity	NPD5729	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