NPASS Compound

Structure

CID224076 OpenBabel06191716022D 23 26 0 0 1 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3939 -2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8097 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5529 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8587 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8587 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5497 1.2601 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 7.5039 -1.3601 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3450 -2.6473 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.6508 -2.2872 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8097 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 13 2 0 0 0 0 2 14 1 0 0 0 0 3 1 1 6 0 0 0 3 6 1 0 0 0 0 3 21 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 5 17 1 1 0 0 0 6 22 1 1 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 16 1 6 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 18 23 1 0 0 0 0 19 23 2 0 0 0 0 20 23 1 0 0 0 0 22 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	363.01
Volume:	279.508
LogP:	-1.702
LogD:	-0.757
LogS:	-1.515
# Rotatable Bonds:	1
TPSA:	152.41
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	5.679
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.053
MDCK Permeability:	3.7874942790949717e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.112
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.402

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.516
Plasma Protein Binding (PPB):	42.520503997802734%
Volume Distribution (VD):	2.234
Pgp-substrate:	63.92200469970703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.135
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.071
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	1.452
Half-life (T1/2):	0.841

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.605
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.347
Rat Oral Acute Toxicity:	0.198
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.419
Carcinogencity:	0.268
Eye Corrosion:	0.004
Eye Irritation:	0.079
Respiratory Toxicity:	0.88

Download Data

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

Natural Product: NPC224076

Natural Product ID:	NPC224076
*Common Name:**	Tocladesine
IUPAC Name:	(4aR,6R,7R,7aS)-6-(6-amino-8-chloropurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
Synonyms:	8-CL-CAMP; Adenazole; ICN-1256; Tocladesine
Standard InCHIKey:	CLLFEJLEDNXZNR-UUOKFMHZSA-N
Standard InCHI:	InChI=1S/C10H11ClN5O6P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,17H,1H2,(H,18,19)(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
SMILES:	C1[C@@H]2[C@H]([C@H]([C@H](n3c4c(c(N)ncn4)nc3Cl)O2)O)OP(=O)(O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2107085
PubChem CID:	100299
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0001506] Purine nucleotides [CHEMONTID:0001491] Cyclic purine nucleotides [CHEMONTID:0001502] 3',5'-cyclic purine nucleotides

*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
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27617953]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28257196]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	71
IC50	2
Others	2

Activity Type	# Activity
Cell Line	71
Others	1
Protein Family	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	10864.26	nM	PMID[558115]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	12647.36	nM	PMID[558115]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	16519.62	nM	PMID[558115]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	16405.9	nM	PMID[558115]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	5046.61	nM	PMID[558115]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	3605.79	nM	PMID[558115]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	12189.9	nM	PMID[558115]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	48977.88	nM	PMID[558115]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	12502.59	nM	PMID[558115]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	152054.75	nM	PMID[558115]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	152405.28	nM	PMID[558115]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	2824.88	nM	PMID[558115]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	67608.3	nM	PMID[558115]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	44874.54	nM	PMID[558115]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	19498.45	nM	PMID[558115]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	6998.42	nM	PMID[558115]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	67764.15	nM	PMID[558115]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	6668.07	nM	PMID[558115]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	5420.01	nM	PMID[558115]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	27669.42	nM	PMID[558115]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	122461.62	nM	PMID[558115]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	3147.75	nM	PMID[558115]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	4698.94	nM	PMID[558115]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	21527.82	nM	PMID[558115]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	12078.14	nM	PMID[558115]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	15135.61	nM	PMID[558115]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	299916.25	nM	PMID[558115]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	27101.92	nM	PMID[558115]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	8016.78	nM	PMID[558115]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	75509.22	nM	PMID[558115]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	18071.74	nM	PMID[558115]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	6471.43	nM	PMID[558115]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	51999.6	nM	PMID[558115]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	16595.87	nM	PMID[558115]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	5688.53	nM	PMID[558115]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	2697.74	nM	PMID[558115]
NPT168	Cell Line	P388	Mus musculus	GI50	n.a.	36728.23	nM	PMID[558115]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	99770.01	nM	PMID[558115]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	13489.63	nM	PMID[558115]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	22750.97	nM	PMID[558115]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	31768.74	nM	PMID[558115]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	37757.22	nM	PMID[558115]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	6698.85	nM	PMID[558115]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	3006.08	nM	PMID[558115]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	31988.95	nM	PMID[558115]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	8109.61	nM	PMID[558115]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	35563.13	nM	PMID[558115]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	26730.06	nM	PMID[558115]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	8298.51	nM	PMID[558115]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	14655.48	nM	PMID[558115]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	10616.96	nM	PMID[558115]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	7030.72	nM	PMID[558115]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	15667.51	nM	PMID[558115]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	5407.54	nM	PMID[558115]
NPT552	Cell Line	P388/ADR	Mus musculus	GI50	n.a.	4528.98	nM	PMID[558115]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	3605.79	nM	PMID[558115]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	24547.09	nM	PMID[558115]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	51168.18	nM	PMID[558115]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	28707.81	nM	PMID[558115]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	164816.24	nM	PMID[558115]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	8851.16	nM	PMID[558115]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	42559.84	nM	PMID[558115]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	3810.66	nM	PMID[558115]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	3483.37	nM	PMID[558115]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	6180.16	nM	PMID[558115]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	295120.92	nM	PMID[558115]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	8394.6	nM	PMID[558115]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[558115]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	7345.14	nM	PMID[558115]
NPT738	Cell Line	SN12K1	Homo sapiens	GI50	n.a.	7261.06	nM	PMID[558115]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	108893.01	nM	PMID[558115]
NPT2	Others	Unspecified		Ka'	=	3.1	n.a.	PMID[558114]
NPT2560	Protein Family	Phosphodiesterase 4	Homo sapiens	Hydrolysis	<	0.05	n.a.	PMID[558114]
NPT2560	Protein Family	Phosphodiesterase 4	Homo sapiens	IC50	=	59000.0	nM	PMID[558114]
NPT2560	Protein Family	Phosphodiesterase 4	Homo sapiens	IC50	=	22000.0	nM	PMID[558114]

☑ 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 NPC224076 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	884
0.1-0.2	27782
0.2-0.3	9546
0.3-0.4	3660
0.4-0.5	529
0.5-0.6	127
0.6-0.7	69
0.7-0.8	31
0.8-0.85	31
0.85-0.9	14
0.9-0.95	18
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC302778
0.9859	High Similarity	NPC212551
0.9718	High Similarity	NPC185991
0.9718	High Similarity	NPC211025
0.9718	High Similarity	NPC85689
0.965	High Similarity	NPC321814
0.9583	High Similarity	NPC130586
0.9583	High Similarity	NPC164952
0.9517	High Similarity	NPC174802
0.9507	High Similarity	NPC121222
0.9437	High Similarity	NPC269827
0.9388	High Similarity	NPC316618
0.9388	High Similarity	NPC226245
0.931	High Similarity	NPC161224
0.9296	High Similarity	NPC156461
0.9296	High Similarity	NPC21448
0.9296	High Similarity	NPC107374
0.9231	High Similarity	NPC189068
0.9231	High Similarity	NPC164665
0.9167	High Similarity	NPC309832
0.9167	High Similarity	NPC219313
0.9155	High Similarity	NPC229974
0.9155	High Similarity	NPC314152
0.9079	High Similarity	NPC323091
0.9014	High Similarity	NPC209525
0.9014	High Similarity	NPC161659
0.8881	High Similarity	NPC317821
0.8861	High Similarity	NPC326529
0.8859	High Similarity	NPC472816
0.8805	High Similarity	NPC319100
0.8805	High Similarity	NPC324198
0.8726	High Similarity	NPC326082
0.8718	High Similarity	NPC261595
0.8662	High Similarity	NPC324033
0.8662	High Similarity	NPC321458
0.8627	High Similarity	NPC239737
0.8609	High Similarity	NPC207633
0.8571	High Similarity	NPC189261
0.8552	High Similarity	NPC129756
0.8477	Intermediate Similarity	NPC150853
0.8411	Intermediate Similarity	NPC136349
0.8387	Intermediate Similarity	NPC311197
0.8387	Intermediate Similarity	NPC54320
0.8387	Intermediate Similarity	NPC313754
0.8323	Intermediate Similarity	NPC52238
0.8267	Intermediate Similarity	NPC89147
0.8267	Intermediate Similarity	NPC274384
0.8247	Intermediate Similarity	NPC328479
0.8231	Intermediate Similarity	NPC33996
0.8231	Intermediate Similarity	NPC30326
0.8219	Intermediate Similarity	NPC320818
0.8079	Intermediate Similarity	NPC251233
0.8079	Intermediate Similarity	NPC211820
0.8067	Intermediate Similarity	NPC186619
0.8026	Intermediate Similarity	NPC177169
0.7987	Intermediate Similarity	NPC195140
0.7974	Intermediate Similarity	NPC64705
0.7974	Intermediate Similarity	NPC232408
0.7961	Intermediate Similarity	NPC318590
0.7925	Intermediate Similarity	NPC93365
0.7908	Intermediate Similarity	NPC317746
0.7885	Intermediate Similarity	NPC326694
0.7853	Intermediate Similarity	NPC324484
0.7818	Intermediate Similarity	NPC290959
0.7805	Intermediate Similarity	NPC325906
0.7738	Intermediate Similarity	NPC313897
0.7733	Intermediate Similarity	NPC61198
0.7667	Intermediate Similarity	NPC262926
0.7622	Intermediate Similarity	NPC14590
0.7562	Intermediate Similarity	NPC321052
0.7529	Intermediate Similarity	NPC24589
0.75	Intermediate Similarity	NPC282458
0.75	Intermediate Similarity	NPC78941
0.7483	Intermediate Similarity	NPC319221
0.7417	Intermediate Similarity	NPC324009
0.7303	Intermediate Similarity	NPC313514
0.7215	Intermediate Similarity	NPC315642
0.7215	Intermediate Similarity	NPC74306
0.7076	Intermediate Similarity	NPC33382
0.7035	Intermediate Similarity	NPC168702
0.7035	Intermediate Similarity	NPC125659
0.7021	Intermediate Similarity	NPC276373
0.6984	Remote Similarity	NPC5802
0.6954	Remote Similarity	NPC222174
0.6947	Remote Similarity	NPC157821
0.6897	Remote Similarity	NPC107160
0.6842	Remote Similarity	NPC321393
0.6796	Remote Similarity	NPC21461
0.6733	Remote Similarity	NPC327579
0.6619	Remote Similarity	NPC158055
0.6552	Remote Similarity	NPC250178
0.6541	Remote Similarity	NPC57279
0.6528	Remote Similarity	NPC476564
0.6519	Remote Similarity	NPC246193
0.6519	Remote Similarity	NPC104011
0.6434	Remote Similarity	NPC174114
0.6434	Remote Similarity	NPC87981
0.641	Remote Similarity	NPC248007
0.6309	Remote Similarity	NPC4837
0.6309	Remote Similarity	NPC312187
0.6263	Remote Similarity	NPC103388
0.6244	Remote Similarity	NPC160666
0.6218	Remote Similarity	NPC139776
0.6211	Remote Similarity	NPC287876
0.6171	Remote Similarity	NPC472834
0.6149	Remote Similarity	NPC14330
0.6081	Remote Similarity	NPC18335
0.5938	Remote Similarity	NPC109322
0.5904	Remote Similarity	NPC164845
0.5872	Remote Similarity	NPC217656
0.586	Remote Similarity	NPC68938
0.5838	Remote Similarity	NPC89139
0.5824	Remote Similarity	NPC296437
0.5789	Remote Similarity	NPC470266
0.5776	Remote Similarity	NPC5707
0.5769	Remote Similarity	NPC313547
0.5739	Remote Similarity	NPC244700
0.5723	Remote Similarity	NPC476528
0.5723	Remote Similarity	NPC476433
0.5706	Remote Similarity	NPC180493
0.5692	Remote Similarity	NPC265111
0.5691	Remote Similarity	NPC472833
0.569	Remote Similarity	NPC476013
0.569	Remote Similarity	NPC476522
0.569	Remote Similarity	NPC476520
0.569	Remote Similarity	NPC474986
0.5682	Remote Similarity	NPC476408
0.566	Remote Similarity	NPC189314
0.5657	Remote Similarity	NPC476521
0.5648	Remote Similarity	NPC473585
0.5629	Remote Similarity	NPC476561

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 NPC224076 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	2195
0.2-0.3	3287
0.3-0.4	2213
0.4-0.5	905
0.5-0.6	162
0.6-0.7	123
0.7-0.8	41
0.8-0.85	17
0.85-0.9	11
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD169	Phase 2
0.9718	High Similarity	NPD283	Approved
0.9583	High Similarity	NPD242	Approved
0.9583	High Similarity	NPD338	Approved
0.9517	High Similarity	NPD339	Approved
0.9437	High Similarity	NPD186	Discovery
0.9296	High Similarity	NPD250	Approved
0.9296	High Similarity	NPD249	Approved
0.9167	High Similarity	NPD195	Approved
0.9155	High Similarity	NPD185	Approved
0.9028	High Similarity	NPD166	Approved
0.8839	High Similarity	NPD7988	Suspended
0.8805	High Similarity	NPD4171	Clinical (unspecified phase)
0.88	High Similarity	NPD1369	Phase 2
0.88	High Similarity	NPD3107	Discontinued
0.88	High Similarity	NPD1750	Clinical (unspecified phase)
0.875	High Similarity	NPD193	Suspended
0.875	High Similarity	NPD1412	Clinical (unspecified phase)
0.875	High Similarity	NPD2646	Discontinued
0.8718	High Similarity	NPD247	Clinical (unspecified phase)
0.8645	High Similarity	NPD3083	Approved
0.8627	High Similarity	NPD1732	Phase 3
0.8627	High Similarity	NPD2624	Phase 2
0.8528	High Similarity	NPD4716	Approved
0.8476	Intermediate Similarity	NPD4744	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD548	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD218	Approved
0.8387	Intermediate Similarity	NPD217	Approved
0.8387	Intermediate Similarity	NPD220	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD216	Approved
0.8387	Intermediate Similarity	NPD219	Phase 3
0.8313	Intermediate Similarity	NPD2647	Phase 3
0.8284	Intermediate Similarity	NPD2632	Approved
0.8284	Intermediate Similarity	NPD2631	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD2630	Approved
0.8194	Intermediate Similarity	NPD213	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD214	Approved
0.8171	Intermediate Similarity	NPD5666	Phase 2
0.8166	Intermediate Similarity	NPD6417	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD248	Discontinued
0.7931	Intermediate Similarity	NPD9633	Phase 3
0.7925	Intermediate Similarity	NPD546	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD7158	Phase 1
0.7877	Intermediate Similarity	NPD9632	Phase 3
0.7847	Intermediate Similarity	NPD9408	Phase 3
0.7805	Intermediate Similarity	NPD1776	Approved
0.7805	Intermediate Similarity	NPD1777	Approved
0.7771	Intermediate Similarity	NPD3085	Phase 1
0.7764	Intermediate Similarity	NPD4074	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD870	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD252	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD3086	Phase 3
0.7644	Intermediate Similarity	NPD5684	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD5683	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD5682	Phase 3
0.763	Intermediate Similarity	NPD1692	Approved
0.7561	Intermediate Similarity	NPD516	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD549	Approved
0.7514	Intermediate Similarity	NPD4054	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD194	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3695	Approved
0.7419	Intermediate Similarity	NPD3696	Approved
0.7346	Intermediate Similarity	NPD536	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7138	Phase 2
0.7247	Intermediate Similarity	NPD1063	Phase 2
0.7215	Intermediate Similarity	NPD582	Approved
0.7125	Intermediate Similarity	NPD171	Discontinued
0.7117	Intermediate Similarity	NPD3708	Phase 2
0.7073	Intermediate Similarity	NPD353	Discontinued
0.7068	Intermediate Similarity	NPD2824	Phase 2
0.7063	Intermediate Similarity	NPD4240	Approved
0.7	Intermediate Similarity	NPD2965	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2876	Phase 3
0.6928	Remote Similarity	NPD231	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2902	Phase 2
0.691	Remote Similarity	NPD1046	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5080	Phase 2
0.6826	Remote Similarity	NPD9605	Phase 3
0.6818	Remote Similarity	NPD5079	Phase 2
0.6779	Remote Similarity	NPD9606	Approved
0.6733	Remote Similarity	NPD9607	Approved
0.665	Remote Similarity	NPD4495	Phase 1
0.6619	Remote Similarity	NPD6840	Approved
0.6604	Remote Similarity	NPD209	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD9409	Discontinued
0.6541	Remote Similarity	NPD545	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD527	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1730	Discontinued
0.6467	Remote Similarity	NPD9374	Approved
0.6443	Remote Similarity	NPD9373	Approved
0.6438	Remote Similarity	NPD547	Clinical (unspecified phase)
0.641	Remote Similarity	NPD9084	Phase 2
0.6405	Remote Similarity	NPD307	Approved
0.6375	Remote Similarity	NPD282	Approved
0.6358	Remote Similarity	NPD1119	Phase 2
0.6294	Remote Similarity	NPD775	Approved
0.6263	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD4458	Phase 2
0.6228	Remote Similarity	NPD1431	Approved
0.6228	Remote Similarity	NPD2253	Discontinued
0.6228	Remote Similarity	NPD1430	Approved
0.6211	Remote Similarity	NPD8829	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD9083	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD1058	Discontinued
0.6182	Remote Similarity	NPD6112	Approved
0.6178	Remote Similarity	NPD207	Discontinued
0.6144	Remote Similarity	NPD9584	Phase 2
0.614	Remote Similarity	NPD7531	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD2452	Phase 2
0.6089	Remote Similarity	NPD2453	Phase 2
0.6089	Remote Similarity	NPD2451	Phase 2
0.6089	Remote Similarity	NPD2450	Phase 2
0.6087	Remote Similarity	NPD1128	Approved
0.6087	Remote Similarity	NPD1127	Approved
0.6081	Remote Similarity	NPD8836	Approved
0.6062	Remote Similarity	NPD281	Approved
0.6061	Remote Similarity	NPD9484	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD799	Phase 1
0.6048	Remote Similarity	NPD1808	Phase 1
0.6019	Remote Similarity	NPD6381	Phase 2
0.5976	Remote Similarity	NPD1118	Discontinued
0.597	Remote Similarity	NPD5486	Discontinued
0.596	Remote Similarity	NPD9416	Phase 3
0.596	Remote Similarity	NPD9417	Phase 3
0.596	Remote Similarity	NPD691	Discontinued
0.5956	Remote Similarity	NPD8250	Phase 2
0.5948	Remote Similarity	NPD9375	Discontinued
0.5941	Remote Similarity	NPD4715	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD34	Approved
0.5941	Remote Similarity	NPD4713	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4714	Approved
0.5938	Remote Similarity	NPD798	Discontinued
0.5936	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD1120	Approved
0.5928	Remote Similarity	NPD1121	Approved
0.5928	Remote Similarity	NPD535	Approved
0.5882	Remote Similarity	NPD5458	Discontinued
0.5867	Remote Similarity	NPD9626	Clinical (unspecified phase)
0.5828	Remote Similarity	NPD515	Phase 1
0.5814	Remote Similarity	NPD1117	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD9582	Phase 3
0.5789	Remote Similarity	NPD1816	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD3849	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD8830	Phase 3
0.5767	Remote Similarity	NPD6036	Suspended
0.5732	Remote Similarity	NPD9406	Approved
0.573	Remote Similarity	NPD7842	Phase 2
0.5723	Remote Similarity	NPD237	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD78	Approved
0.5706	Remote Similarity	NPD9544	Approved
0.5701	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD5627	Approved
0.57	Remote Similarity	NPD796	Phase 2
0.5691	Remote Similarity	NPD1017	Clinical (unspecified phase)
0.5665	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.566	Remote Similarity	NPD8831	Approved
0.566	Remote Similarity	NPD8833	Approved
0.5652	Remote Similarity	NPD6351	Discovery
0.5633	Remote Similarity	NPD757	Phase 3
0.5628	Remote Similarity	NPD537	Phase 2
0.5628	Remote Similarity	NPD534	Phase 2
0.5625	Remote Similarity	NPD9360	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