NPASS Compound

Structure

CID260075 OpenBabel06191716062D 26 32 0 0 1 0 0 0 0 0999 V2000 -2.2665 -1.3083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2663 -0.4357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5113 -1.7446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5110 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0070 -1.1612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8303 -2.0730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5294 -2.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2860 -0.8181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2664 -1.3092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7559 0.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7093 -1.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7595 -0.8940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2666 -0.4366 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7555 -1.3086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7553 -0.4360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3619 0.6555 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5111 -1.7452 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1498 0.6557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5114 -0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7556 -0.4363 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7554 -1.3089 0.0000 C 0 0 1 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 2.1537 -1.9434 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5654 1.2264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0537 -2.1081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0187 -0.0656 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 14 2 0 0 0 0 4 15 2 0 0 0 0 5 8 1 0 0 0 0 5 12 2 0 0 0 0 6 7 1 0 0 0 0 6 21 1 0 0 0 0 7 23 1 0 0 0 0 8 26 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 13 9 1 1 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 10 1 1 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 21 1 6 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 24 2 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 23 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.16
Volume:	347.059
LogP:	0.275
LogD:	1.485
LogS:	-1.718
# Rotatable Bonds:	0
TPSA:	52.6
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	6.183
Fsp3:	0.571
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:	-5.356
MDCK Permeability:	2.828301330737304e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.959
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	15.342437744140625%
Volume Distribution (VD):	0.853
Pgp-substrate:	78.49274444580078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.278
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.735
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.1
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	14.844
Half-life (T1/2):	0.93

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.256
Carcinogencity:	0.961
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.884

Download Data

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

Natural Product: NPC260075

Natural Product ID:	NPC260075
*Common Name:**	Strychnine-N-Oxide
IUPAC Name:	(4aR,5aS,8aS,13aS,15aS,15bR)-6-oxido-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-6-ium-14-one
Synonyms:
Standard InCHIKey:	ADTDBAKUQAKBGZ-VXJIXCKJSA-N
Standard InCHI:	InChI=1S/C21H22N2O3/c24-18-10-16-19-13-9-17-21(6-7-23(17,25)11-12(13)5-8-26-16)14-3-1-2-4-15(14)22(18)20(19)21/h1-5,13,16-17,19-20H,6-11H2/t13-,16-,17-,19-,20-,21+,23?/m0/s1
SMILES:	O=C1C[C@@H]2OCC=C3[C@H]4[C@@H]2[C@@H]2N1c1ccccc1[C@]12CCN(=O)([C@H]1C4)C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL138585
PubChem CID:	73393
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos 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
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0040-4020(73)80248-0]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/j.tet.2012.03.006]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[10.1016/j.tet.2012.03.006]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170658]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	root	n.a.	PMID[11170658]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398531]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	root	n.a.	PMID[12560037]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[16317898]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[17449162]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[19235686]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	Root bark	Central Africa	n.a.	PMID[19299148]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19666019]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[22707864]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23088673]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[2393954]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24593048]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[25594733]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25594733]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[4954818]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[7912074]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4386	Strychnos icaja	Species	Loganiaceae	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	5
Others	23

Activity Type	# Activity
Cell Line	5
Individual Protein	16
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT262	Individual Protein	Muscarinic acetylcholine receptor M1	Homo sapiens	Affinity	<	3.6	n.a.	PMID[495195]
NPT262	Individual Protein	Muscarinic acetylcholine receptor M1	Homo sapiens	Affinity	=	3.8	n.a.	PMID[495195]
NPT263	Individual Protein	Muscarinic acetylcholine receptor M2	Homo sapiens	Affinity	<	4.1	n.a.	PMID[495195]
NPT263	Individual Protein	Muscarinic acetylcholine receptor M2	Homo sapiens	Affinity	=	4.4	n.a.	PMID[495195]
NPT264	Individual Protein	Muscarinic acetylcholine receptor M3	Homo sapiens	Affinity	<	3.9	n.a.	PMID[495195]
NPT264	Individual Protein	Muscarinic acetylcholine receptor M3	Homo sapiens	Affinity	=	3.9	n.a.	PMID[495195]
NPT265	Individual Protein	Muscarinic acetylcholine receptor M4	Homo sapiens	Affinity	<	3.8	n.a.	PMID[495195]
NPT265	Individual Protein	Muscarinic acetylcholine receptor M4	Homo sapiens	Affinity	=	4.1	n.a.	PMID[495195]
NPT262	Individual Protein	Muscarinic acetylcholine receptor M1	Homo sapiens	Cooperativity	=	2.0	n.a.	PMID[495195]
NPT263	Individual Protein	Muscarinic acetylcholine receptor M2	Homo sapiens	Cooperativity	>	2.0	n.a.	PMID[495195]
NPT264	Individual Protein	Muscarinic acetylcholine receptor M3	Homo sapiens	Cooperativity	=	2.0	n.a.	PMID[495195]
NPT265	Individual Protein	Muscarinic acetylcholine receptor M4	Homo sapiens	Cooperativity	=	2.0	n.a.	PMID[495195]
NPT262	Individual Protein	Muscarinic acetylcholine receptor M1	Homo sapiens	Cooperativity	=	0.8	n.a.	PMID[495195]
NPT263	Individual Protein	Muscarinic acetylcholine receptor M2	Homo sapiens	Cooperativity	=	0.8	n.a.	PMID[495195]
NPT264	Individual Protein	Muscarinic acetylcholine receptor M3	Homo sapiens	Cooperativity	=	0.8	n.a.	PMID[495195]
NPT265	Individual Protein	Muscarinic acetylcholine receptor M4	Homo sapiens	Cooperativity	=	0.8	n.a.	PMID[495195]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[495196]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[495196]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[495196]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[495196]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[495196]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	=	13.5	%	PMID[495197]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	9.12	%	PMID[495197]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	3.06	%	PMID[495197]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	-6.02	%	PMID[495197]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	Inhibition	=	-3.57	%	PMID[495197]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	-14.45	%	PMID[495197]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	1.56	%	PMID[495197]

☑ 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 NPC260075 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	317
0.1-0.2	1442
0.2-0.3	4371
0.3-0.4	21550
0.4-0.5	11112
0.5-0.6	3252
0.6-0.7	507
0.7-0.8	122
0.8-0.85	13
0.85-0.9	3
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9563	High Similarity	NPC251212
0.9563	High Similarity	NPC214626
0.9563	High Similarity	NPC139085
0.8844	High Similarity	NPC22689
0.8844	High Similarity	NPC105055
0.8547	High Similarity	NPC162440
0.8412	Intermediate Similarity	NPC96901
0.8407	Intermediate Similarity	NPC67904
0.8407	Intermediate Similarity	NPC138830
0.8253	Intermediate Similarity	NPC113946
0.8226	Intermediate Similarity	NPC329833
0.8155	Intermediate Similarity	NPC225319
0.8084	Intermediate Similarity	NPC29285
0.8012	Intermediate Similarity	NPC472106
0.8	Intermediate Similarity	NPC203202
0.8	Intermediate Similarity	NPC264482
0.7941	Intermediate Similarity	NPC248117
0.7895	Intermediate Similarity	NPC472120
0.7895	Intermediate Similarity	NPC99632
0.7895	Intermediate Similarity	NPC472101
0.7895	Intermediate Similarity	NPC282339
0.7882	Intermediate Similarity	NPC193410
0.7841	Intermediate Similarity	NPC469726
0.7841	Intermediate Similarity	NPC329338
0.7835	Intermediate Similarity	NPC159815
0.7824	Intermediate Similarity	NPC61013
0.7791	Intermediate Similarity	NPC286871
0.7791	Intermediate Similarity	NPC176983
0.7753	Intermediate Similarity	NPC476326
0.7738	Intermediate Similarity	NPC475763
0.7714	Intermediate Similarity	NPC167724
0.7714	Intermediate Similarity	NPC223595
0.7714	Intermediate Similarity	NPC224970
0.7709	Intermediate Similarity	NPC6974
0.7709	Intermediate Similarity	NPC99043
0.7709	Intermediate Similarity	NPC218594
0.7688	Intermediate Similarity	NPC472117
0.768	Intermediate Similarity	NPC159963
0.7661	Intermediate Similarity	NPC469536
0.7657	Intermediate Similarity	NPC214960
0.7657	Intermediate Similarity	NPC279527
0.7654	Intermediate Similarity	NPC186669
0.7616	Intermediate Similarity	NPC123241
0.7598	Intermediate Similarity	NPC320147
0.7596	Intermediate Similarity	NPC52262
0.7586	Intermediate Similarity	NPC293458
0.7584	Intermediate Similarity	NPC473743
0.7581	Intermediate Similarity	NPC25401
0.7562	Intermediate Similarity	NPC318525
0.7562	Intermediate Similarity	NPC10653
0.7529	Intermediate Similarity	NPC472102
0.7529	Intermediate Similarity	NPC309531
0.7529	Intermediate Similarity	NPC243756
0.7527	Intermediate Similarity	NPC476428
0.7514	Intermediate Similarity	NPC14994
0.7486	Intermediate Similarity	NPC476425
0.7471	Intermediate Similarity	NPC36495
0.746	Intermediate Similarity	NPC221687
0.7447	Intermediate Similarity	NPC473004
0.7442	Intermediate Similarity	NPC478076
0.7429	Intermediate Similarity	NPC143457
0.741	Intermediate Similarity	NPC186284
0.741	Intermediate Similarity	NPC22082
0.7374	Intermediate Similarity	NPC469915
0.7351	Intermediate Similarity	NPC97584
0.7308	Intermediate Similarity	NPC476441
0.7303	Intermediate Similarity	NPC471124
0.7294	Intermediate Similarity	NPC264589
0.7283	Intermediate Similarity	NPC122106
0.724	Intermediate Similarity	NPC473375
0.724	Intermediate Similarity	NPC97100
0.7231	Intermediate Similarity	NPC471512
0.7219	Intermediate Similarity	NPC259626
0.7219	Intermediate Similarity	NPC469537
0.7207	Intermediate Similarity	NPC475420
0.7204	Intermediate Similarity	NPC477159
0.72	Intermediate Similarity	NPC473297
0.7198	Intermediate Similarity	NPC285622
0.7188	Intermediate Similarity	NPC230313
0.7188	Intermediate Similarity	NPC243626
0.7178	Intermediate Similarity	NPC473006
0.7175	Intermediate Similarity	NPC471122
0.7169	Intermediate Similarity	NPC471123
0.7166	Intermediate Similarity	NPC2933
0.7158	Intermediate Similarity	NPC473008
0.7158	Intermediate Similarity	NPC13367
0.7143	Intermediate Similarity	NPC21425
0.7135	Intermediate Similarity	NPC474058
0.7128	Intermediate Similarity	NPC472209
0.7128	Intermediate Similarity	NPC473007
0.7126	Intermediate Similarity	NPC154602
0.7112	Intermediate Similarity	NPC256288
0.7104	Intermediate Similarity	NPC473880
0.7097	Intermediate Similarity	NPC11149
0.7097	Intermediate Similarity	NPC286994
0.7095	Intermediate Similarity	NPC469741
0.7077	Intermediate Similarity	NPC100863
0.7072	Intermediate Similarity	NPC472115
0.7072	Intermediate Similarity	NPC472114
0.7069	Intermediate Similarity	NPC318086
0.7068	Intermediate Similarity	NPC473298
0.7044	Intermediate Similarity	NPC10732
0.7043	Intermediate Similarity	NPC321211
0.7041	Intermediate Similarity	NPC130251
0.7039	Intermediate Similarity	NPC315368
0.7039	Intermediate Similarity	NPC77777
0.7039	Intermediate Similarity	NPC477158
0.7037	Intermediate Similarity	NPC322621
0.7033	Intermediate Similarity	NPC63047
0.7033	Intermediate Similarity	NPC475248
0.7029	Intermediate Similarity	NPC66936
0.702	Intermediate Similarity	NPC473005
0.7006	Intermediate Similarity	NPC161827
0.7005	Intermediate Similarity	NPC288110
0.7005	Intermediate Similarity	NPC475489
0.7	Intermediate Similarity	NPC473615
0.6963	Remote Similarity	NPC181928
0.6963	Remote Similarity	NPC229484
0.6959	Remote Similarity	NPC470485
0.6944	Remote Similarity	NPC201424
0.6943	Remote Similarity	NPC203628
0.6943	Remote Similarity	NPC22476
0.6927	Remote Similarity	NPC284706
0.6927	Remote Similarity	NPC292675
0.6923	Remote Similarity	NPC34717
0.6902	Remote Similarity	NPC472118
0.6895	Remote Similarity	NPC245741
0.6893	Remote Similarity	NPC285381
0.6891	Remote Similarity	NPC473569
0.6891	Remote Similarity	NPC5630
0.6889	Remote Similarity	NPC263709
0.6889	Remote Similarity	NPC97380
0.6889	Remote Similarity	NPC243673
0.6889	Remote Similarity	NPC310403
0.6889	Remote Similarity	NPC63210
0.6889	Remote Similarity	NPC148468
0.6882	Remote Similarity	NPC469560
0.6875	Remote Similarity	NPC285841
0.6875	Remote Similarity	NPC473329
0.6866	Remote Similarity	NPC475847
0.6866	Remote Similarity	NPC185742
0.6859	Remote Similarity	NPC472107
0.6859	Remote Similarity	NPC476095
0.6859	Remote Similarity	NPC79062
0.6857	Remote Similarity	NPC212799
0.6856	Remote Similarity	NPC470483
0.6853	Remote Similarity	NPC90967
0.685	Remote Similarity	NPC1464
0.6839	Remote Similarity	NPC116519
0.6832	Remote Similarity	NPC477161
0.6831	Remote Similarity	NPC470069
0.6831	Remote Similarity	NPC52059
0.6828	Remote Similarity	NPC276993
0.6828	Remote Similarity	NPC181138
0.6828	Remote Similarity	NPC293255
0.6828	Remote Similarity	NPC298851
0.6828	Remote Similarity	NPC21752
0.6828	Remote Similarity	NPC210415
0.6823	Remote Similarity	NPC282092
0.6802	Remote Similarity	NPC301760
0.6802	Remote Similarity	NPC303214
0.6796	Remote Similarity	NPC469461
0.6776	Remote Similarity	NPC473458
0.6771	Remote Similarity	NPC469460
0.6766	Remote Similarity	NPC52801
0.6766	Remote Similarity	NPC162730
0.6757	Remote Similarity	NPC33507
0.675	Remote Similarity	NPC127178
0.6749	Remote Similarity	NPC246140
0.6749	Remote Similarity	NPC195787
0.674	Remote Similarity	NPC104345
0.674	Remote Similarity	NPC211525
0.674	Remote Similarity	NPC222029
0.674	Remote Similarity	NPC153694
0.6734	Remote Similarity	NPC218733
0.6734	Remote Similarity	NPC138615
0.6734	Remote Similarity	NPC265642
0.6734	Remote Similarity	NPC132874
0.6732	Remote Similarity	NPC477160
0.6723	Remote Similarity	NPC242000
0.6716	Remote Similarity	NPC232600
0.6716	Remote Similarity	NPC469732
0.6702	Remote Similarity	NPC475097
0.6702	Remote Similarity	NPC470548
0.67	Remote Similarity	NPC87714
0.6683	Remote Similarity	NPC475559
0.6683	Remote Similarity	NPC474116
0.6682	Remote Similarity	NPC222046
0.6667	Remote Similarity	NPC474121
0.6649	Remote Similarity	NPC307640
0.6647	Remote Similarity	NPC315051
0.6647	Remote Similarity	NPC243162
0.6635	Remote Similarity	NPC127996
0.6632	Remote Similarity	NPC472119
0.663	Remote Similarity	NPC472121
0.663	Remote Similarity	NPC85651
0.6629	Remote Similarity	NPC308197
0.662	Remote Similarity	NPC471513
0.6619	Remote Similarity	NPC234772
0.6618	Remote Similarity	NPC470489

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 NPC260075 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	572
0.2-0.3	732
0.3-0.4	1771
0.4-0.5	3772
0.5-0.6	1904
0.6-0.7	193
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7011	Intermediate Similarity	NPD5997	Discontinued
0.6894	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7487	Discontinued
0.6763	Remote Similarity	NPD6566	Discontinued
0.676	Remote Similarity	NPD4120	Approved
0.676	Remote Similarity	NPD4121	Phase 3
0.6722	Remote Similarity	NPD5742	Approved
0.6722	Remote Similarity	NPD5743	Approved
0.6722	Remote Similarity	NPD5741	Approved
0.6667	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6805	Discontinued
0.6536	Remote Similarity	NPD4682	Phase 2
0.6535	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3422	Phase 3
0.6526	Remote Similarity	NPD3423	Phase 2
0.6519	Remote Similarity	NPD8401	Approved
0.6519	Remote Similarity	NPD8402	Approved
0.6519	Remote Similarity	NPD8400	Approved
0.6497	Remote Similarity	NPD5918	Discontinued
0.6497	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6878	Phase 2
0.6477	Remote Similarity	NPD6879	Phase 2
0.6464	Remote Similarity	NPD7606	Phase 3
0.6461	Remote Similarity	NPD7295	Approved
0.644	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7599	Phase 2
0.6429	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4601	Approved
0.6422	Remote Similarity	NPD4600	Approved
0.6414	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7205	Discontinued
0.6398	Remote Similarity	NPD7600	Phase 2
0.6395	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.639	Remote Similarity	NPD6238	Discontinued
0.6389	Remote Similarity	NPD7478	Approved
0.6383	Remote Similarity	NPD7036	Phase 3
0.6383	Remote Similarity	NPD7035	Approved
0.6373	Remote Similarity	NPD5600	Discontinued
0.6369	Remote Similarity	NPD5931	Phase 3
0.6369	Remote Similarity	NPD5933	Phase 3
0.6369	Remote Similarity	NPD5932	Phase 3
0.6364	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6995	Phase 1
0.6359	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7082	Approved
0.6344	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD2670	Approved
0.6341	Remote Similarity	NPD4501	Approved
0.6341	Remote Similarity	NPD4500	Approved
0.6324	Remote Similarity	NPD1663	Discontinued
0.6313	Remote Similarity	NPD7259	Approved
0.6304	Remote Similarity	NPD2790	Discontinued
0.6292	Remote Similarity	NPD6768	Approved
0.6289	Remote Similarity	NPD5312	Approved
0.6289	Remote Similarity	NPD5313	Approved
0.6283	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5941	Approved
0.6264	Remote Similarity	NPD5182	Approved
0.6264	Remote Similarity	NPD5942	Approved
0.6264	Remote Similarity	NPD5184	Approved
0.6264	Remote Similarity	NPD5185	Approved
0.6257	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD2820	Phase 3
0.6257	Remote Similarity	NPD4549	Discontinued
0.6257	Remote Similarity	NPD4430	Phase 2
0.625	Remote Similarity	NPD6358	Phase 2
0.625	Remote Similarity	NPD4334	Discontinued
0.6244	Remote Similarity	NPD8281	Discontinued
0.6243	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD4041	Approved
0.6236	Remote Similarity	NPD3625	Discontinued
0.6235	Remote Similarity	NPD5180	Approved
0.6235	Remote Similarity	NPD5179	Approved
0.6235	Remote Similarity	NPD5181	Approved
0.6232	Remote Similarity	NPD6321	Discontinued
0.6224	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD7244	Discontinued
0.6219	Remote Similarity	NPD4499	Approved
0.6218	Remote Similarity	NPD3377	Discontinued
0.6203	Remote Similarity	NPD8630	Approved
0.6201	Remote Similarity	NPD2365	Approved
0.62	Remote Similarity	NPD6891	Phase 2
0.6198	Remote Similarity	NPD5183	Approved
0.6198	Remote Similarity	NPD5186	Approved
0.6188	Remote Similarity	NPD5504	Discontinued
0.6186	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD6489	Phase 3
0.6173	Remote Similarity	NPD7881	Approved
0.6173	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD2948	Discontinued
0.6162	Remote Similarity	NPD3399	Approved
0.6161	Remote Similarity	NPD7688	Phase 1
0.6158	Remote Similarity	NPD2569	Approved
0.6158	Remote Similarity	NPD2567	Approved
0.6154	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6395	Phase 2
0.615	Remote Similarity	NPD6571	Approved
0.615	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6570	Approved
0.6146	Remote Similarity	NPD6457	Approved
0.6145	Remote Similarity	NPD2093	Discontinued
0.6141	Remote Similarity	NPD1405	Approved
0.6138	Remote Similarity	NPD2506	Approved
0.6133	Remote Similarity	NPD2435	Approved
0.6132	Remote Similarity	NPD2916	Discontinued
0.6127	Remote Similarity	NPD4365	Phase 2
0.6124	Remote Similarity	NPD3170	Approved
0.6122	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7595	Discontinued
0.612	Remote Similarity	NPD1802	Approved
0.612	Remote Similarity	NPD1801	Approved
0.6119	Remote Similarity	NPD3437	Discontinued
0.6117	Remote Similarity	NPD3828	Approved
0.6117	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3470	Approved
0.6111	Remote Similarity	NPD3471	Approved
0.6111	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5427	Suspended
0.6103	Remote Similarity	NPD7940	Phase 3
0.6102	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6557	Phase 2
0.6099	Remote Similarity	NPD6622	Phase 1
0.6099	Remote Similarity	NPD6017	Discontinued
0.6098	Remote Similarity	NPD4602	Approved
0.6094	Remote Similarity	NPD5823	Approved
0.6091	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD8025	Phase 2
0.6087	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4644	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD6518	Discontinued
0.6082	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.608	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4315	Phase 2
0.6077	Remote Similarity	NPD5024	Approved
0.6071	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.607	Remote Similarity	NPD5444	Phase 1
0.6066	Remote Similarity	NPD3141	Discontinued
0.6066	Remote Similarity	NPD1956	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD7105	Phase 1
0.6064	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD7126	Discontinued
0.6061	Remote Similarity	NPD4330	Approved
0.6061	Remote Similarity	NPD4329	Approved
0.6054	Remote Similarity	NPD7186	Phase 3
0.6048	Remote Similarity	NPD2994	Approved
0.6045	Remote Similarity	NPD2791	Discontinued
0.6044	Remote Similarity	NPD7824	Approved
0.6043	Remote Similarity	NPD8016	Phase 3
0.6043	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD3449	Discontinued
0.6041	Remote Similarity	NPD3792	Approved
0.604	Remote Similarity	NPD6484	Approved
0.604	Remote Similarity	NPD6483	Approved
0.6039	Remote Similarity	NPD6206	Phase 1
0.6038	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD3912	Discontinued
0.6034	Remote Similarity	NPD5131	Approved
0.6034	Remote Similarity	NPD4946	Phase 2
0.6034	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD7795	Phase 2
0.6029	Remote Similarity	NPD8240	Discontinued
0.6029	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD6659	Phase 2
0.6025	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6176	Phase 1
0.6012	Remote Similarity	NPD5993	Phase 1
0.6011	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.601	Remote Similarity	NPD5071	Phase 2
0.601	Remote Similarity	NPD7775	Approved
0.6009	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7528	Approved
0.6	Remote Similarity	NPD2432	Approved
0.6	Remote Similarity	NPD2427	Approved
0.6	Remote Similarity	NPD3824	Phase 1
0.6	Remote Similarity	NPD2431	Approved
0.6	Remote Similarity	NPD7962	Phase 2
0.6	Remote Similarity	NPD3551	Approved
0.599	Remote Similarity	NPD3790	Phase 2
0.599	Remote Similarity	NPD8007	Approved
0.599	Remote Similarity	NPD8008	Approved
0.5988	Remote Similarity	NPD2116	Approved
0.5988	Remote Similarity	NPD5990	Approved
0.5988	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD5991	Approved
0.5988	Remote Similarity	NPD2115	Approved
0.5988	Remote Similarity	NPD2117	Pre-registration
0.5981	Remote Similarity	NPD7665	Phase 2
0.5981	Remote Similarity	NPD8027	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