NPASS Compound

Structure

CID228012 OpenBabel06191716022D 23 25 0 0 1 0 0 0 0 0999 V2000 3.4641 1.0000 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 1.7321 -2.0000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 2 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 0.8660 -1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 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 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 0.0000 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 10 1 0 0 0 0 4 7 2 0 0 0 0 4 9 1 0 0 0 0 5 7 1 0 0 0 0 5 11 2 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 8 13 1 0 0 0 0 8 18 1 6 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 1 0 0 0 14 15 1 0 0 0 0 15 20 2 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.07
Volume:	302.699
LogP:	0.847
LogD:	1.064
LogS:	-3.623
# Rotatable Bonds:	3
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.426
Synthetic Accessibility Score:	3.423
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.112
MDCK Permeability:	4.084889496880351e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.926
Human Intestinal Absorption (HIA):	0.816
20% Bioavailability (F20%):	0.136
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	90.07553100585938%
Volume Distribution (VD):	0.953
Pgp-substrate:	19.401878356933594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.406
CYP1A2-substrate:	0.848
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.118
CYP2C9-substrate:	0.523
CYP2D6-inhibitor:	0.164
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	1.851
Half-life (T1/2):	0.845

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.097
Drug-inuced Liver Injury (DILI):	0.874
AMES Toxicity:	0.619
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.263
Skin Sensitization:	0.75
Carcinogencity:	0.046
Eye Corrosion:	0.004
Eye Irritation:	0.887
Respiratory Toxicity:	0.129

Download Data

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

Natural Product: NPC228012

Natural Product ID:	NPC228012
*Common Name:**	Methyl (1R,2R)-2,8-Dihydroxy-6-(Hydroxymethyl)-9-Oxo-1,2-Dihydroxanthene-1-Carboxylate
IUPAC Name:	methyl (1R,2R)-2,8-dihydroxy-6-(hydroxymethyl)-9-oxo-1,2-dihydroxanthene-1-carboxylate
Synonyms:
Standard InCHIKey:	MPAKYMOQGZITTQ-OQPBUACISA-N
Standard InCHI:	InChI=1S/C16H14O7/c1-22-16(21)13-8(18)2-3-10-14(13)15(20)12-9(19)4-7(6-17)5-11(12)23-10/h2-5,8,13,17-19H,6H2,1H3/t8-,13+/m1/s1
SMILES:	COC(=O)[C@H]1[C@H](O)C=Cc2c1c(=O)c1c(o2)cc(cc1O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1812025
PubChem CID:	5472392
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647825]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24057165]

☑ 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	57
IC50	3
Others	2

Activity Type	# Activity
Cell Line	57
NON-MOLECULAR	4
Others	1

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.	4591.98	nM	PMID[476689]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	9862.79	nM	PMID[476689]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	19010.78	nM	PMID[476689]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	3775.72	nM	PMID[476689]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	8629.79	nM	PMID[476689]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	2249.05	nM	PMID[476689]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	3243.4	nM	PMID[476689]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	2673.01	nM	PMID[476689]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	5727.96	nM	PMID[476689]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	1737.8	nM	PMID[476689]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	3280.95	nM	PMID[476689]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	7261.06	nM	PMID[476689]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	8016.78	nM	PMID[476689]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	4518.56	nM	PMID[476689]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	17947.34	nM	PMID[476689]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	10495.42	nM	PMID[476689]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	17947.34	nM	PMID[476689]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	9506.05	nM	PMID[476689]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	5559.04	nM	PMID[476689]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	14092.89	nM	PMID[476689]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	17701.09	nM	PMID[476689]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	2344.23	nM	PMID[476689]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	5597.58	nM	PMID[476689]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	3111.72	nM	PMID[476689]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	1836.54	nM	PMID[476689]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	3706.81	nM	PMID[476689]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	5970.35	nM	PMID[476689]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	2494.59	nM	PMID[476689]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	3523.71	nM	PMID[476689]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	3318.94	nM	PMID[476689]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	2937.65	nM	PMID[476689]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	15240.53	nM	PMID[476689]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	16826.74	nM	PMID[476689]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	17864.88	nM	PMID[476689]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	2697.74	nM	PMID[476689]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	2296.15	nM	PMID[476689]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	6194.41	nM	PMID[476689]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	7177.94	nM	PMID[476689]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	2857.59	nM	PMID[476689]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	13335.21	nM	PMID[476689]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	20511.62	nM	PMID[476689]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	2697.74	nM	PMID[476689]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	18620.87	nM	PMID[476689]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	12302.69	nM	PMID[476689]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	7998.34	nM	PMID[476689]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	4149.54	nM	PMID[476689]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	10839.27	nM	PMID[476689]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	18365.38	nM	PMID[476689]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	24660.39	nM	PMID[476689]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	8851.16	nM	PMID[476689]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	2449.06	nM	PMID[476689]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	1690.44	nM	PMID[476689]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	25822.6	nM	PMID[476689]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	4159.11	nM	PMID[476689]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	3388.44	nM	PMID[476689]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	2798.98	nM	PMID[476689]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	5495.41	nM	PMID[476689]
NPT1	Others	Radical scavenging activity		IC50	=	17000.0	nM	PMID[476688]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	98.92	%	PMID[476690]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6600.0	nM	PMID[476690]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	101.58	%	PMID[476690]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6000.0	nM	PMID[476690]

☑ 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 NPC228012 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	352
0.1-0.2	1484
0.2-0.3	3552
0.3-0.4	7885
0.4-0.5	10779
0.5-0.6	3911
0.6-0.7	5639
0.7-0.8	5034
0.8-0.85	3499
0.85-0.9	543
0.9-0.95	17
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9257	High Similarity	NPC39819
0.9252	High Similarity	NPC73236
0.9247	High Similarity	NPC146884
0.92	High Similarity	NPC237560
0.9195	High Similarity	NPC281272
0.9091	High Similarity	NPC268691
0.898	High Similarity	NPC469764
0.8933	High Similarity	NPC475717
0.8926	High Similarity	NPC191634
0.8919	High Similarity	NPC469758
0.8889	High Similarity	NPC154341
0.8867	High Similarity	NPC70764
0.8859	High Similarity	NPC71055
0.8844	High Similarity	NPC1534
0.8824	High Similarity	NPC326910
0.8808	High Similarity	NPC295036
0.8808	High Similarity	NPC474735
0.8758	High Similarity	NPC193200
0.8758	High Similarity	NPC198236
0.8758	High Similarity	NPC301233
0.8716	High Similarity	NPC476164
0.8716	High Similarity	NPC476310
0.8716	High Similarity	NPC73028
0.8707	High Similarity	NPC145673
0.8693	High Similarity	NPC271681
0.8684	High Similarity	NPC37348
0.8684	High Similarity	NPC470107
0.8684	High Similarity	NPC158866
0.8675	High Similarity	NPC240253
0.8675	High Similarity	NPC153417
0.8675	High Similarity	NPC240622
0.8675	High Similarity	NPC471641
0.8675	High Similarity	NPC471642
0.8658	High Similarity	NPC470909
0.8658	High Similarity	NPC10302
0.8658	High Similarity	NPC105381
0.8658	High Similarity	NPC113770
0.8658	High Similarity	NPC96216
0.8658	High Similarity	NPC89664
0.8658	High Similarity	NPC274085
0.8658	High Similarity	NPC474939
0.8654	High Similarity	NPC186113
0.8649	High Similarity	NPC24075
0.8645	High Similarity	NPC272550
0.8636	High Similarity	NPC472799
0.8636	High Similarity	NPC135522
0.863	High Similarity	NPC98395
0.863	High Similarity	NPC61590
0.8627	High Similarity	NPC475076
0.8627	High Similarity	NPC46564
0.8627	High Similarity	NPC290671
0.8627	High Similarity	NPC207346
0.8618	High Similarity	NPC4423
0.8618	High Similarity	NPC77325
0.8618	High Similarity	NPC474052
0.8609	High Similarity	NPC285748
0.86	High Similarity	NPC288910
0.86	High Similarity	NPC470554
0.86	High Similarity	NPC184649
0.86	High Similarity	NPC311144
0.86	High Similarity	NPC303185
0.86	High Similarity	NPC118059
0.86	High Similarity	NPC133060
0.86	High Similarity	NPC224714
0.8599	High Similarity	NPC130955
0.8591	High Similarity	NPC294432
0.8591	High Similarity	NPC472006
0.8591	High Similarity	NPC470556
0.8591	High Similarity	NPC51106
0.859	High Similarity	NPC44199
0.859	High Similarity	NPC108456
0.859	High Similarity	NPC281137
0.859	High Similarity	NPC282390
0.8581	High Similarity	NPC182421
0.8581	High Similarity	NPC175192
0.8571	High Similarity	NPC473967
0.8571	High Similarity	NPC321363
0.8571	High Similarity	NPC474843
0.8571	High Similarity	NPC256141
0.8571	High Similarity	NPC295339
0.8571	High Similarity	NPC18457
0.8571	High Similarity	NPC253904
0.8571	High Similarity	NPC273483
0.8571	High Similarity	NPC275878
0.8562	High Similarity	NPC470397
0.8562	High Similarity	NPC202595
0.8562	High Similarity	NPC180351
0.8562	High Similarity	NPC150928
0.8562	High Similarity	NPC472633
0.8553	High Similarity	NPC5537
0.8553	High Similarity	NPC2569
0.8553	High Similarity	NPC172329
0.8553	High Similarity	NPC37139
0.8543	High Similarity	NPC130176
0.8543	High Similarity	NPC99454
0.8543	High Similarity	NPC290133
0.8543	High Similarity	NPC107625
0.8543	High Similarity	NPC196114
0.8543	High Similarity	NPC472629
0.8543	High Similarity	NPC470322
0.8543	High Similarity	NPC299011
0.8543	High Similarity	NPC154217
0.8543	High Similarity	NPC187282
0.8543	High Similarity	NPC470910
0.8543	High Similarity	NPC24136
0.8535	High Similarity	NPC470339
0.8533	High Similarity	NPC307895
0.8533	High Similarity	NPC470216
0.8533	High Similarity	NPC33653
0.8533	High Similarity	NPC470553
0.8533	High Similarity	NPC475201
0.8533	High Similarity	NPC103910
0.8533	High Similarity	NPC184738
0.8531	High Similarity	NPC137264
0.8526	High Similarity	NPC472050
0.8523	High Similarity	NPC474385
0.8521	High Similarity	NPC187907
0.8514	High Similarity	NPC222342
0.8514	High Similarity	NPC329203
0.8514	High Similarity	NPC469523
0.8514	High Similarity	NPC310135
0.8514	High Similarity	NPC265871
0.8514	High Similarity	NPC20709
0.8514	High Similarity	NPC139554
0.8514	High Similarity	NPC150648
0.8514	High Similarity	NPC225153
0.8514	High Similarity	NPC274784
0.8506	High Similarity	NPC295650
0.8506	High Similarity	NPC70016
0.8506	High Similarity	NPC215921
0.8503	High Similarity	NPC332594
0.8503	High Similarity	NPC287068
0.8497	Intermediate Similarity	NPC470461
0.8497	Intermediate Similarity	NPC104236
0.8497	Intermediate Similarity	NPC139966
0.8497	Intermediate Similarity	NPC5173
0.8497	Intermediate Similarity	NPC307052
0.8497	Intermediate Similarity	NPC237440
0.8497	Intermediate Similarity	NPC19238
0.8497	Intermediate Similarity	NPC477941
0.8497	Intermediate Similarity	NPC270160
0.8497	Intermediate Similarity	NPC164205
0.8497	Intermediate Similarity	NPC269420
0.8497	Intermediate Similarity	NPC317492
0.8491	Intermediate Similarity	NPC473961
0.8487	Intermediate Similarity	NPC474108
0.8487	Intermediate Similarity	NPC308200
0.8487	Intermediate Similarity	NPC177995
0.8487	Intermediate Similarity	NPC472036
0.8483	Intermediate Similarity	NPC223457
0.8481	Intermediate Similarity	NPC472055
0.8477	Intermediate Similarity	NPC1886
0.8477	Intermediate Similarity	NPC316535
0.8477	Intermediate Similarity	NPC312789
0.8477	Intermediate Similarity	NPC87486
0.8477	Intermediate Similarity	NPC124780
0.8477	Intermediate Similarity	NPC196137
0.8477	Intermediate Similarity	NPC470890
0.8471	Intermediate Similarity	NPC246466
0.8471	Intermediate Similarity	NPC263483
0.8467	Intermediate Similarity	NPC469542
0.8467	Intermediate Similarity	NPC112829
0.8467	Intermediate Similarity	NPC472344
0.8467	Intermediate Similarity	NPC202981
0.8462	Intermediate Similarity	NPC473241
0.8462	Intermediate Similarity	NPC170189
0.8462	Intermediate Similarity	NPC478230
0.8462	Intermediate Similarity	NPC208173
0.8462	Intermediate Similarity	NPC12694
0.8462	Intermediate Similarity	NPC39753
0.8462	Intermediate Similarity	NPC115998
0.8462	Intermediate Similarity	NPC69043
0.8456	Intermediate Similarity	NPC284550
0.8456	Intermediate Similarity	NPC67650
0.8456	Intermediate Similarity	NPC76445
0.8456	Intermediate Similarity	NPC129853
0.8456	Intermediate Similarity	NPC1704
0.8456	Intermediate Similarity	NPC6407
0.8456	Intermediate Similarity	NPC158634
0.8456	Intermediate Similarity	NPC110228
0.8456	Intermediate Similarity	NPC188243
0.8452	Intermediate Similarity	NPC470340
0.8452	Intermediate Similarity	NPC184284
0.8452	Intermediate Similarity	NPC87708
0.8452	Intermediate Similarity	NPC175978
0.8452	Intermediate Similarity	NPC76041
0.8452	Intermediate Similarity	NPC154683
0.8452	Intermediate Similarity	NPC40356
0.8447	Intermediate Similarity	NPC13481
0.8447	Intermediate Similarity	NPC207575
0.8446	Intermediate Similarity	NPC118813
0.8446	Intermediate Similarity	NPC12175
0.8446	Intermediate Similarity	NPC279668
0.8446	Intermediate Similarity	NPC268052
0.8446	Intermediate Similarity	NPC90665
0.8446	Intermediate Similarity	NPC55162
0.8446	Intermediate Similarity	NPC278323
0.8446	Intermediate Similarity	NPC309154
0.8442	Intermediate Similarity	NPC469619
0.8442	Intermediate Similarity	NPC471115

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 NPC228012 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	923
0.2-0.3	1657
0.3-0.4	2526
0.4-0.5	2003
0.5-0.6	1138
0.6-0.7	372
0.7-0.8	142
0.8-0.85	59
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8707	High Similarity	NPD1878	Clinical (unspecified phase)
0.8562	High Similarity	NPD1551	Phase 2
0.8462	Intermediate Similarity	NPD5402	Approved
0.8446	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1934	Approved
0.8333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3750	Approved
0.8322	Intermediate Similarity	NPD1549	Phase 2
0.828	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD3226	Approved
0.8247	Intermediate Similarity	NPD5403	Approved
0.8243	Intermediate Similarity	NPD1510	Phase 2
0.8235	Intermediate Similarity	NPD5401	Approved
0.8235	Intermediate Similarity	NPD2532	Approved
0.8235	Intermediate Similarity	NPD2533	Approved
0.8235	Intermediate Similarity	NPD2534	Approved
0.8188	Intermediate Similarity	NPD2796	Approved
0.817	Intermediate Similarity	NPD1511	Approved
0.8165	Intermediate Similarity	NPD2801	Approved
0.8165	Intermediate Similarity	NPD7819	Suspended
0.8133	Intermediate Similarity	NPD2346	Discontinued
0.8125	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7075	Discontinued
0.8113	Intermediate Similarity	NPD3817	Phase 2
0.811	Intermediate Similarity	NPD7473	Discontinued
0.8108	Intermediate Similarity	NPD1607	Approved
0.8101	Intermediate Similarity	NPD6801	Discontinued
0.8089	Intermediate Similarity	NPD4380	Phase 2
0.8084	Intermediate Similarity	NPD6559	Discontinued
0.8082	Intermediate Similarity	NPD2313	Discontinued
0.8065	Intermediate Similarity	NPD1512	Approved
0.8061	Intermediate Similarity	NPD3818	Discontinued
0.805	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD7411	Suspended
0.8037	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3748	Approved
0.7975	Intermediate Similarity	NPD6959	Discontinued
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7973	Intermediate Similarity	NPD1240	Approved
0.7959	Intermediate Similarity	NPD411	Approved
0.795	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7768	Phase 2
0.7947	Intermediate Similarity	NPD2935	Discontinued
0.7939	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6166	Phase 2
0.7935	Intermediate Similarity	NPD6799	Approved
0.7929	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD447	Suspended
0.7908	Intermediate Similarity	NPD2800	Approved
0.7904	Intermediate Similarity	NPD7054	Approved
0.7902	Intermediate Similarity	NPD9717	Approved
0.7898	Intermediate Similarity	NPD920	Approved
0.7885	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD4308	Phase 3
0.7862	Intermediate Similarity	NPD1203	Approved
0.7857	Intermediate Similarity	NPD7472	Approved
0.7857	Intermediate Similarity	NPD7074	Phase 3
0.784	Intermediate Similarity	NPD3882	Suspended
0.7829	Intermediate Similarity	NPD6099	Approved
0.7829	Intermediate Similarity	NPD6100	Approved
0.7811	Intermediate Similarity	NPD6797	Phase 2
0.78	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD5844	Phase 1
0.7798	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3749	Approved
0.7778	Intermediate Similarity	NPD8313	Approved
0.7778	Intermediate Similarity	NPD8312	Approved
0.7771	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7251	Discontinued
0.7763	Intermediate Similarity	NPD2799	Discontinued
0.7763	Intermediate Similarity	NPD7033	Discontinued
0.7742	Intermediate Similarity	NPD4628	Phase 3
0.774	Intermediate Similarity	NPD2797	Approved
0.7725	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD4749	Approved
0.7719	Intermediate Similarity	NPD7808	Phase 3
0.7718	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD3268	Approved
0.7708	Intermediate Similarity	NPD422	Phase 1
0.7703	Intermediate Similarity	NPD6832	Phase 2
0.7697	Intermediate Similarity	NPD5494	Approved
0.7682	Intermediate Similarity	NPD5124	Phase 1
0.7682	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1243	Approved
0.7677	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4307	Phase 2
0.7605	Intermediate Similarity	NPD5710	Approved
0.7605	Intermediate Similarity	NPD5711	Approved
0.7602	Intermediate Similarity	NPD5953	Discontinued
0.7602	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1019	Discontinued
0.7568	Intermediate Similarity	NPD2798	Approved
0.7566	Intermediate Similarity	NPD230	Phase 1
0.7548	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD9493	Approved
0.7534	Intermediate Similarity	NPD1608	Approved
0.7532	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD919	Approved
0.7516	Intermediate Similarity	NPD6651	Approved
0.75	Intermediate Similarity	NPD3267	Approved
0.75	Intermediate Similarity	NPD3266	Approved
0.7485	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7286	Phase 2
0.7448	Intermediate Similarity	NPD1778	Approved
0.7443	Intermediate Similarity	NPD8434	Phase 2
0.7439	Intermediate Similarity	NPD37	Approved
0.7439	Intermediate Similarity	NPD6844	Discontinued
0.7436	Intermediate Similarity	NPD6002	Phase 3
0.7436	Intermediate Similarity	NPD6004	Phase 3
0.7436	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6005	Phase 3
0.7436	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2344	Approved
0.7432	Intermediate Similarity	NPD3225	Approved
0.7427	Intermediate Similarity	NPD3751	Discontinued
0.7414	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4965	Approved
0.741	Intermediate Similarity	NPD4967	Phase 2
0.741	Intermediate Similarity	NPD4966	Approved
0.7394	Intermediate Similarity	NPD1465	Phase 2
0.7386	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1613	Approved
0.7383	Intermediate Similarity	NPD1470	Approved
0.7368	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1296	Phase 2
0.7351	Intermediate Similarity	NPD4908	Phase 1
0.7349	Intermediate Similarity	NPD4288	Approved
0.7347	Intermediate Similarity	NPD1610	Phase 2
0.7345	Intermediate Similarity	NPD8150	Discontinued
0.7342	Intermediate Similarity	NPD1652	Phase 2
0.7338	Intermediate Similarity	NPD1933	Approved
0.7337	Intermediate Similarity	NPD1247	Approved
0.7333	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD17	Approved
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.731	Intermediate Similarity	NPD1548	Phase 1
0.7303	Intermediate Similarity	NPD4625	Phase 3
0.7301	Intermediate Similarity	NPD1653	Approved
0.7284	Intermediate Similarity	NPD6273	Approved
0.7279	Intermediate Similarity	NPD3496	Discontinued
0.7273	Intermediate Similarity	NPD943	Approved
0.7263	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2309	Approved
0.723	Intermediate Similarity	NPD1201	Approved
0.7219	Intermediate Similarity	NPD5647	Approved
0.7209	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD4360	Phase 2
0.7198	Intermediate Similarity	NPD4363	Phase 3
0.7193	Intermediate Similarity	NPD7229	Phase 3
0.7192	Intermediate Similarity	NPD9545	Approved
0.7176	Intermediate Similarity	NPD6746	Phase 2
0.7172	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7435	Discontinued
0.716	Intermediate Similarity	NPD7390	Discontinued
0.716	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5406	Approved
0.7152	Intermediate Similarity	NPD5405	Approved
0.7152	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD5408	Approved
0.7151	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7135	Intermediate Similarity	NPD7199	Phase 2
0.7134	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7228	Approved
0.7124	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6355	Discontinued
0.7097	Intermediate Similarity	NPD6779	Approved
0.7097	Intermediate Similarity	NPD6776	Approved
0.7097	Intermediate Similarity	NPD6777	Approved
0.7097	Intermediate Similarity	NPD6782	Approved
0.7097	Intermediate Similarity	NPD6781	Approved
0.7097	Intermediate Similarity	NPD6780	Approved
0.7097	Intermediate Similarity	NPD6778	Approved
0.7093	Intermediate Similarity	NPD3787	Discontinued
0.7086	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD5760	Phase 2
0.7083	Intermediate Similarity	NPD5761	Phase 2
0.7083	Intermediate Similarity	NPD1241	Discontinued
0.7081	Intermediate Similarity	NPD7003	Approved
0.7078	Intermediate Similarity	NPD3027	Phase 3
0.707	Intermediate Similarity	NPD6653	Approved
0.7068	Intermediate Similarity	NPD8151	Discontinued
0.7059	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2861	Phase 2
0.7048	Intermediate Similarity	NPD7458	Discontinued
0.7044	Intermediate Similarity	NPD6032	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