NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	145.05
Volume:	153.712
LogP:	1.9
LogD:	1.626
LogS:	-2.25
# Rotatable Bonds:	0
TPSA:	33.12
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	1.756
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.483
MDCK Permeability:	2.9764567443635315e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.938
30% Bioavailability (F30%):	0.664

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.442
Plasma Protein Binding (PPB):	85.23316955566406%
Volume Distribution (VD):	1.048
Pgp-substrate:	13.764662742614746%

ADMET: Metabolism

CYP1A2-inhibitor:	0.867
CYP1A2-substrate:	0.589
CYP2C19-inhibitor:	0.388
CYP2C19-substrate:	0.456
CYP2C9-inhibitor:	0.172
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.237
CYP2D6-substrate:	0.784
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	10.778
Half-life (T1/2):	0.785

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.044
Drug-inuced Liver Injury (DILI):	0.83
AMES Toxicity:	0.468
Rat Oral Acute Toxicity:	0.484
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.802
Carcinogencity:	0.289
Eye Corrosion:	0.444
Eye Irritation:	0.986
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC473764

Natural Product ID:	NPC473764
*Common Name:**	Quinosol
IUPAC Name:	n.a.
Synonyms:	8-Hydroxyquinoline Sulfate; Quinosol
Standard InCHIKey:	MRUMAIRJPMUAPZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H7NO.H2O4S/c11-8-5-1-3-7-4-2-6-10-9(7)8;1-5(2,3)4/h1-6,11H;(H2,1,2,3,4)
SMILES:	OS(=O)(=O)O.Oc1cccc2c1nccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451260
PubChem CID:	11507008 6451191
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000057] Hydroxyquinolines

*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
NPO2192	Cortinarius subtortus	Species	Cortinariaceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[18447384]
NPO2192	Cortinarius subtortus	Species	Cortinariaceae	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
EC50	1
Others	13
Potency	9

Activity Type	# Activity
Individual Protein	8
Organism	13
Others	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	11220.2	nM	PMID[547499]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	2238.7	nM	PMID[547499]
NPT1119	Individual Protein	Arachidonate 12-lipoxygenase	Homo sapiens	Potency	=	10000.0	nM	PMID[547499]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	4456.3	nM	PMID[547499]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	1000.0	nM	PMID[547499]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	2592.9	nM	PMID[547499]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	3264.3	nM	PMID[547499]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	125.9	nM	PMID[547499]
NPT3518	Organism	Colletotrichum coccodes	Colletotrichum coccodes	EC50	=	190.0	nM	PMID[547497]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	15.0	mm	PMID[547498]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	15.0	mm	PMID[547498]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	20.0	mm	PMID[547498]
NPT4338	Organism	Streptomyces viridochromogenes	Streptomyces viridochromogenes	IZ	=	0.0	mm	PMID[547498]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	11.0	mm	PMID[547498]
NPT2526	Organism	Rhizomucor miehei	Rhizomucor miehei	IZ	=	30.0	mm	PMID[547498]
NPT4339	Organism	Chlorella vulgaris	Chlorella vulgaris	IZ	=	25.0	mm	PMID[547498]
NPT4340	Organism	Chlorella sorokiniana	Chlorella sorokiniana	IZ	=	28.0	mm	PMID[547498]
NPT4341	Organism	Desmodesmus subspicatus	Desmodesmus subspicatus	IZ	=	27.0	mm	PMID[547498]
NPT2	Others	Unspecified		Potency	=	3981.1	nM	PMID[547499]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-8.5	%	PMID[547500]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	14.79	%	PMID[547501]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.05	%	PMID[547502]

☑ 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 NPC473764 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	651
0.1-0.2	6741
0.2-0.3	10849
0.3-0.4	13363
0.4-0.5	6922
0.5-0.6	2592
0.6-0.7	1373
0.7-0.8	196
0.8-0.85	7
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC314940
0.9554	High Similarity	NPC252590
0.8743	High Similarity	NPC192315
0.8693	High Similarity	NPC476167
0.8412	Intermediate Similarity	NPC478032
0.8407	Intermediate Similarity	NPC477113
0.8402	Intermediate Similarity	NPC184964
0.8333	Intermediate Similarity	NPC60553
0.8315	Intermediate Similarity	NPC477111
0.8303	Intermediate Similarity	NPC118511
0.8208	Intermediate Similarity	NPC220765
0.8161	Intermediate Similarity	NPC204717
0.8155	Intermediate Similarity	NPC44161
0.814	Intermediate Similarity	NPC42979
0.8129	Intermediate Similarity	NPC224764
0.8125	Intermediate Similarity	NPC220523
0.8114	Intermediate Similarity	NPC42591
0.8114	Intermediate Similarity	NPC314002
0.8068	Intermediate Similarity	NPC171171
0.8034	Intermediate Similarity	NPC144381
0.8024	Intermediate Similarity	NPC124542
0.8024	Intermediate Similarity	NPC471177
0.8024	Intermediate Similarity	NPC59779
0.8021	Intermediate Similarity	NPC18348
0.801	Intermediate Similarity	NPC477110
0.8	Intermediate Similarity	NPC475774
0.7987	Intermediate Similarity	NPC174421
0.7977	Intermediate Similarity	NPC96890
0.7967	Intermediate Similarity	NPC90229
0.7946	Intermediate Similarity	NPC470678
0.7944	Intermediate Similarity	NPC99666
0.7929	Intermediate Similarity	NPC471178
0.7919	Intermediate Similarity	NPC150048
0.7919	Intermediate Similarity	NPC203754
0.7903	Intermediate Similarity	NPC245816
0.7903	Intermediate Similarity	NPC476138
0.7901	Intermediate Similarity	NPC329541
0.7901	Intermediate Similarity	NPC230403
0.7857	Intermediate Similarity	NPC25899
0.7845	Intermediate Similarity	NPC324149
0.7831	Intermediate Similarity	NPC63562
0.7824	Intermediate Similarity	NPC8022
0.7824	Intermediate Similarity	NPC470799
0.7821	Intermediate Similarity	NPC46580
0.7811	Intermediate Similarity	NPC48192
0.7772	Intermediate Similarity	NPC77555
0.7766	Intermediate Similarity	NPC118832
0.7766	Intermediate Similarity	NPC470500
0.7766	Intermediate Similarity	NPC329708
0.7766	Intermediate Similarity	NPC264166
0.7766	Intermediate Similarity	NPC274291
0.7766	Intermediate Similarity	NPC165349
0.7766	Intermediate Similarity	NPC47059
0.7765	Intermediate Similarity	NPC97367
0.7765	Intermediate Similarity	NPC473057
0.776	Intermediate Similarity	NPC326634
0.7754	Intermediate Similarity	NPC211813
0.7749	Intermediate Similarity	NPC5145
0.7738	Intermediate Similarity	NPC132680
0.7738	Intermediate Similarity	NPC269919
0.7735	Intermediate Similarity	NPC3715
0.7717	Intermediate Similarity	NPC222018
0.7702	Intermediate Similarity	NPC318935
0.7697	Intermediate Similarity	NPC48938
0.768	Intermediate Similarity	NPC230805
0.7676	Intermediate Similarity	NPC156704
0.7676	Intermediate Similarity	NPC267928
0.7672	Intermediate Similarity	NPC475070
0.7667	Intermediate Similarity	NPC314573
0.7653	Intermediate Similarity	NPC173080
0.765	Intermediate Similarity	NPC132631
0.765	Intermediate Similarity	NPC103687
0.7647	Intermediate Similarity	NPC131718
0.7647	Intermediate Similarity	NPC315491
0.7647	Intermediate Similarity	NPC45459
0.7647	Intermediate Similarity	NPC322976
0.7647	Intermediate Similarity	NPC324203
0.7647	Intermediate Similarity	NPC63338
0.7641	Intermediate Similarity	NPC142901
0.7607	Intermediate Similarity	NPC470394
0.7607	Intermediate Similarity	NPC470404
0.7607	Intermediate Similarity	NPC470403
0.7602	Intermediate Similarity	NPC177404
0.7586	Intermediate Similarity	NPC164664
0.7582	Intermediate Similarity	NPC46358
0.7582	Intermediate Similarity	NPC32771
0.756	Intermediate Similarity	NPC26872
0.7558	Intermediate Similarity	NPC263439
0.7558	Intermediate Similarity	NPC211187
0.7558	Intermediate Similarity	NPC102423
0.7553	Intermediate Similarity	NPC213308
0.7553	Intermediate Similarity	NPC19872
0.7539	Intermediate Similarity	NPC476124
0.7539	Intermediate Similarity	NPC476121
0.7538	Intermediate Similarity	NPC476287
0.7532	Intermediate Similarity	NPC256893
0.7527	Intermediate Similarity	NPC251090
0.7527	Intermediate Similarity	NPC242209
0.7526	Intermediate Similarity	NPC53144
0.7515	Intermediate Similarity	NPC470395
0.7514	Intermediate Similarity	NPC307963
0.7513	Intermediate Similarity	NPC185782
0.75	Intermediate Similarity	NPC193238
0.75	Intermediate Similarity	NPC476451
0.75	Intermediate Similarity	NPC153769
0.75	Intermediate Similarity	NPC477112
0.7486	Intermediate Similarity	NPC296527
0.7484	Intermediate Similarity	NPC151489
0.7474	Intermediate Similarity	NPC309845
0.7471	Intermediate Similarity	NPC108469
0.7446	Intermediate Similarity	NPC76748
0.7444	Intermediate Similarity	NPC266551
0.7444	Intermediate Similarity	NPC219963
0.7444	Intermediate Similarity	NPC161887
0.7442	Intermediate Similarity	NPC120798
0.7435	Intermediate Similarity	NPC200836
0.743	Intermediate Similarity	NPC72980
0.743	Intermediate Similarity	NPC88363
0.7427	Intermediate Similarity	NPC26850
0.7425	Intermediate Similarity	NPC257142
0.7405	Intermediate Similarity	NPC92111
0.7399	Intermediate Similarity	NPC79911
0.7398	Intermediate Similarity	NPC26679
0.7394	Intermediate Similarity	NPC224928
0.7386	Intermediate Similarity	NPC256828
0.7371	Intermediate Similarity	NPC41717
0.7368	Intermediate Similarity	NPC176538
0.7368	Intermediate Similarity	NPC315957
0.7368	Intermediate Similarity	NPC141353
0.7368	Intermediate Similarity	NPC234197
0.7365	Intermediate Similarity	NPC161292
0.7354	Intermediate Similarity	NPC212213
0.7346	Intermediate Similarity	NPC328029
0.7345	Intermediate Similarity	NPC158129
0.7345	Intermediate Similarity	NPC253810
0.7341	Intermediate Similarity	NPC322644
0.7337	Intermediate Similarity	NPC66083
0.732	Intermediate Similarity	NPC88008
0.7318	Intermediate Similarity	NPC288943
0.7316	Intermediate Similarity	NPC128823
0.7306	Intermediate Similarity	NPC472259
0.7303	Intermediate Similarity	NPC313791
0.7303	Intermediate Similarity	NPC474409
0.7297	Intermediate Similarity	NPC472289
0.7297	Intermediate Similarity	NPC242928
0.7296	Intermediate Similarity	NPC85273
0.7294	Intermediate Similarity	NPC284348
0.7287	Intermediate Similarity	NPC146724
0.7286	Intermediate Similarity	NPC476161
0.7282	Intermediate Similarity	NPC171787
0.7282	Intermediate Similarity	NPC287208
0.7278	Intermediate Similarity	NPC283152
0.7273	Intermediate Similarity	NPC133140
0.7273	Intermediate Similarity	NPC162530
0.7273	Intermediate Similarity	NPC195268
0.7268	Intermediate Similarity	NPC284678
0.7268	Intermediate Similarity	NPC207851
0.7268	Intermediate Similarity	NPC156059
0.7264	Intermediate Similarity	NPC292958
0.7263	Intermediate Similarity	NPC312872
0.7263	Intermediate Similarity	NPC303225
0.7254	Intermediate Similarity	NPC476098
0.7253	Intermediate Similarity	NPC474798
0.725	Intermediate Similarity	NPC476041
0.725	Intermediate Similarity	NPC304926
0.725	Intermediate Similarity	NPC469727
0.7241	Intermediate Similarity	NPC279918
0.7238	Intermediate Similarity	NPC149402
0.7234	Intermediate Similarity	NPC226202
0.7231	Intermediate Similarity	NPC283117
0.7228	Intermediate Similarity	NPC295158
0.7228	Intermediate Similarity	NPC20249
0.7225	Intermediate Similarity	NPC287437
0.7225	Intermediate Similarity	NPC129721
0.7222	Intermediate Similarity	NPC112206
0.7222	Intermediate Similarity	NPC202605
0.7207	Intermediate Similarity	NPC471294
0.7206	Intermediate Similarity	NPC167908
0.7205	Intermediate Similarity	NPC324611
0.7202	Intermediate Similarity	NPC159856
0.7202	Intermediate Similarity	NPC66815
0.72	Intermediate Similarity	NPC47298
0.72	Intermediate Similarity	NPC282231
0.72	Intermediate Similarity	NPC315214
0.72	Intermediate Similarity	NPC224632
0.72	Intermediate Similarity	NPC288349
0.7196	Intermediate Similarity	NPC276517
0.7194	Intermediate Similarity	NPC476157
0.7188	Intermediate Similarity	NPC249040
0.7186	Intermediate Similarity	NPC266931
0.7186	Intermediate Similarity	NPC477610
0.7184	Intermediate Similarity	NPC230869
0.7183	Intermediate Similarity	NPC473312
0.7174	Intermediate Similarity	NPC62069
0.7173	Intermediate Similarity	NPC239954
0.717	Intermediate Similarity	NPC212125
0.717	Intermediate Similarity	NPC306397
0.717	Intermediate Similarity	NPC165370
0.7168	Intermediate Similarity	NPC477889
0.7164	Intermediate Similarity	NPC473513

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 NPC473764 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	824
0.2-0.3	731
0.3-0.4	1597
0.4-0.5	2865
0.5-0.6	2066
0.6-0.7	666
0.7-0.8	86
0.8-0.85	5
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9682	High Similarity	NPD9690	Approved
0.9608	High Similarity	NPD9705	Discontinued
0.9608	High Similarity	NPD112	Approved
0.8947	High Similarity	NPD9695	Approved
0.8889	High Similarity	NPD9689	Approved
0.8726	High Similarity	NPD9706	Clinical (unspecified phase)
0.8588	High Similarity	NPD9687	Approved
0.8588	High Similarity	NPD9688	Approved
0.8187	Intermediate Similarity	NPD6159	Phase 2
0.8121	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD425	Approved
0.8095	Intermediate Similarity	NPD424	Approved
0.8	Intermediate Similarity	NPD2615	Phase 3
0.8	Intermediate Similarity	NPD2616	Phase 3
0.7978	Intermediate Similarity	NPD408	Approved
0.7978	Intermediate Similarity	NPD2177	Approved
0.7978	Intermediate Similarity	NPD2176	Approved
0.7978	Intermediate Similarity	NPD2175	Phase 3
0.7933	Intermediate Similarity	NPD1213	Phase 3
0.7929	Intermediate Similarity	NPD926	Approved
0.7929	Intermediate Similarity	NPD925	Approved
0.7923	Intermediate Similarity	NPD712	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD5255	Approved
0.7901	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD2781	Approved
0.7824	Intermediate Similarity	NPD2780	Approved
0.7824	Intermediate Similarity	NPD2782	Approved
0.7797	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD4036	Approved
0.7766	Intermediate Similarity	NPD4035	Approved
0.7766	Intermediate Similarity	NPD4033	Approved
0.7766	Intermediate Similarity	NPD4039	Approved
0.7766	Intermediate Similarity	NPD31	Approved
0.7766	Intermediate Similarity	NPD4037	Approved
0.7766	Intermediate Similarity	NPD4034	Approved
0.7766	Intermediate Similarity	NPD32	Approved
0.7766	Intermediate Similarity	NPD4122	Approved
0.7766	Intermediate Similarity	NPD4038	Approved
0.7738	Intermediate Similarity	NPD9382	Approved
0.7738	Intermediate Similarity	NPD9383	Approved
0.7684	Intermediate Similarity	NPD6290	Phase 2
0.768	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7948	Phase 1
0.7654	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7603	Discontinued
0.7647	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD484	Approved
0.763	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3477	Phase 2
0.7611	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD1856	Discontinued
0.7557	Intermediate Similarity	NPD5065	Approved
0.7554	Intermediate Similarity	NPD6569	Phase 2
0.7529	Intermediate Similarity	NPD2582	Approved
0.7529	Intermediate Similarity	NPD2581	Approved
0.7526	Intermediate Similarity	NPD4502	Phase 2
0.7526	Intermediate Similarity	NPD5939	Approved
0.7526	Intermediate Similarity	NPD5936	Approved
0.7514	Intermediate Similarity	NPD1038	Approved
0.75	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2882	Phase 1
0.75	Intermediate Similarity	NPD6158	Phase 2
0.7487	Intermediate Similarity	NPD1229	Phase 2
0.7474	Intermediate Similarity	NPD3931	Approved
0.7474	Intermediate Similarity	NPD3928	Approved
0.7455	Intermediate Similarity	NPD3813	Approved
0.7444	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD2123	Phase 3
0.7432	Intermediate Similarity	NPD2383	Phase 1
0.7427	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5100	Phase 3
0.7407	Intermediate Similarity	NPD5999	Phase 2
0.7374	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1740	Approved
0.7368	Intermediate Similarity	NPD1739	Approved
0.7358	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD862	Approved
0.7356	Intermediate Similarity	NPD863	Approved
0.7356	Intermediate Similarity	NPD861	Approved
0.7321	Intermediate Similarity	NPD1661	Suspended
0.7321	Intermediate Similarity	NPD4702	Approved
0.7321	Intermediate Similarity	NPD4703	Approved
0.732	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD4429	Discontinued
0.73	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6975	Discontinued
0.7289	Intermediate Similarity	NPD3525	Discontinued
0.7286	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7112	Discontinued
0.7286	Intermediate Similarity	NPD5612	Discontinued
0.7273	Intermediate Similarity	NPD3921	Approved
0.7273	Intermediate Similarity	NPD3923	Approved
0.7273	Intermediate Similarity	NPD3922	Approved
0.7273	Intermediate Similarity	NPD3924	Approved
0.7263	Intermediate Similarity	NPD158	Discontinued
0.7253	Intermediate Similarity	NPD4203	Approved
0.7253	Intermediate Similarity	NPD4204	Approved
0.7238	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6361	Phase 2
0.7234	Intermediate Similarity	NPD4551	Phase 2
0.7231	Intermediate Similarity	NPD7222	Phase 2
0.7228	Intermediate Similarity	NPD4889	Approved
0.7222	Intermediate Similarity	NPD2381	Approved
0.7222	Intermediate Similarity	NPD2380	Approved
0.7222	Intermediate Similarity	NPD2382	Approved
0.7216	Intermediate Similarity	NPD4795	Phase 2
0.72	Intermediate Similarity	NPD1685	Approved
0.72	Intermediate Similarity	NPD1684	Approved
0.717	Intermediate Similarity	NPD9080	Approved
0.717	Intermediate Similarity	NPD9284	Approved
0.7167	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD3321	Discontinued
0.7157	Intermediate Similarity	NPD4945	Discontinued
0.7152	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1034	Phase 3
0.7151	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD802	Phase 2
0.7136	Intermediate Similarity	NPD3330	Phase 1
0.7135	Intermediate Similarity	NPD3825	Phase 3
0.7135	Intermediate Similarity	NPD4548	Discontinued
0.7135	Intermediate Similarity	NPD5862	Discovery
0.7115	Intermediate Similarity	NPD5022	Discontinued
0.7111	Intermediate Similarity	NPD2076	Approved
0.7111	Intermediate Similarity	NPD2077	Approved
0.7105	Intermediate Similarity	NPD3395	Approved
0.7105	Intermediate Similarity	NPD3396	Approved
0.7104	Intermediate Similarity	NPD9510	Approved
0.7085	Intermediate Similarity	NPD3779	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4044	Discontinued
0.7066	Intermediate Similarity	NPD1649	Discontinued
0.7065	Intermediate Similarity	NPD3386	Phase 2
0.7062	Intermediate Similarity	NPD4511	Phase 1
0.7056	Intermediate Similarity	NPD7452	Approved
0.7056	Intermediate Similarity	NPD7453	Approved
0.705	Intermediate Similarity	NPD7069	Discontinued
0.7044	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6590	Discontinued
0.701	Intermediate Similarity	NPD6389	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4375	Approved
0.7005	Intermediate Similarity	NPD706	Phase 1
0.7	Intermediate Similarity	NPD4372	Phase 1
0.7	Intermediate Similarity	NPD3404	Approved
0.6989	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD9506	Approved
0.6984	Remote Similarity	NPD8063	Discontinued
0.6982	Remote Similarity	NPD3717	Discontinued
0.698	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5512	Phase 3
0.6977	Remote Similarity	NPD3576	Approved
0.6977	Remote Similarity	NPD1183	Approved
0.6977	Remote Similarity	NPD3575	Approved
0.6973	Remote Similarity	NPD1570	Approved
0.697	Remote Similarity	NPD1392	Approved
0.6968	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7469	Discontinued
0.6959	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3082	Discontinued
0.6952	Remote Similarity	NPD2762	Phase 2
0.6952	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4699	Discontinued
0.6947	Remote Similarity	NPD2334	Discontinued
0.6946	Remote Similarity	NPD2896	Discontinued
0.6943	Remote Similarity	NPD2952	Discontinued
0.694	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD2720	Phase 1
0.6927	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5530	Phase 1
0.6919	Remote Similarity	NPD6452	Discontinued
0.6915	Remote Similarity	NPD4131	Phase 3
0.6915	Remote Similarity	NPD5067	Phase 2
0.6915	Remote Similarity	NPD5066	Phase 2
0.6915	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3809	Discontinued
0.6908	Remote Similarity	NPD8356	Approved
0.6907	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1325	Approved
0.6906	Remote Similarity	NPD1326	Approved
0.6906	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD1032	Phase 2
0.6902	Remote Similarity	NPD8122	Approved
0.6902	Remote Similarity	NPD8123	Approved
0.6897	Remote Similarity	NPD3262	Approved
0.6895	Remote Similarity	NPD5316	Approved
0.6895	Remote Similarity	NPD6281	Approved
0.6885	Remote Similarity	NPD6492	Phase 2
0.6878	Remote Similarity	NPD9364	Phase 2
0.6878	Remote Similarity	NPD3354	Phase 2

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