NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.17
Volume:	301.3
LogP:	3.732
LogD:	3.407
LogS:	-2.651
# Rotatable Bonds:	3
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.649
Synthetic Accessibility Score:	3.737
Fsp3:	0.529
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.605
MDCK Permeability:	1.601047915755771e-05
Pgp-inhibitor:	0.609
Pgp-substrate:	0.14
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.465

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	96.72183990478516%
Volume Distribution (VD):	4.673
Pgp-substrate:	3.6360819339752197%

ADMET: Metabolism

CYP1A2-inhibitor:	0.778
CYP1A2-substrate:	0.871
CYP2C19-inhibitor:	0.823
CYP2C19-substrate:	0.661
CYP2C9-inhibitor:	0.73
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.614
CYP2D6-substrate:	0.74
CYP3A4-inhibitor:	0.61
CYP3A4-substrate:	0.369

ADMET: Excretion

Clearance (CL):	6.671
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.289
Drug-inuced Liver Injury (DILI):	0.108
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.287
Maximum Recommended Daily Dose:	0.769
Skin Sensitization:	0.525
Carcinogencity:	0.112
Eye Corrosion:	0.008
Eye Irritation:	0.181
Respiratory Toxicity:	0.833

Download Data

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

Natural Product: NPC54373

Natural Product ID:	NPC54373
*Common Name:**	Methoxyconidiol
IUPAC Name:	2-[(1R,6S)-6-(2-methoxypropan-2-yl)-3-methylcyclohex-2-en-1-yl]benzene-1,4-diol
Synonyms:	Methoxyconidiol
Standard InCHIKey:	YVRSQIWWSKXPTR-ZFWWWQNUSA-N
Standard InCHI:	InChI=1S/C17H24O3/c1-11-5-7-15(17(2,3)20-4)13(9-11)14-10-12(18)6-8-16(14)19/h6,8-10,13,15,18-19H,5,7H2,1-4H3/t13-,15-/m0/s1
SMILES:	CC1=C[C@@H](c2cc(ccc2O)O)[C@H](CC1)C(C)(C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513459
PubChem CID:	11529200
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO33101	aplidium aff. densum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180826]

☑ 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	1
MIC	2

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	>	10000000.0	nM	PMID[506654]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	2000000.0	nM	PMID[506654]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	2000000.0	nM	PMID[506654]

☑ 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 NPC54373 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	272
0.1-0.2	1463
0.2-0.3	3530
0.3-0.4	12048
0.4-0.5	7817
0.5-0.6	8920
0.6-0.7	6669
0.7-0.8	1748
0.8-0.85	177
0.85-0.9	50
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8962	High Similarity	NPC53740
0.8962	High Similarity	NPC469913
0.8899	High Similarity	NPC266937
0.8899	High Similarity	NPC470770
0.8899	High Similarity	NPC469912
0.8879	High Similarity	NPC320439
0.8868	High Similarity	NPC47284
0.8857	High Similarity	NPC108497
0.8846	High Similarity	NPC72729
0.8846	High Similarity	NPC129373
0.8846	High Similarity	NPC248396
0.8846	High Similarity	NPC48730
0.8839	High Similarity	NPC141001
0.8835	High Similarity	NPC475078
0.8835	High Similarity	NPC152097
0.8829	High Similarity	NPC471534
0.8818	High Similarity	NPC62867
0.8818	High Similarity	NPC177962
0.8785	High Similarity	NPC155072
0.8774	High Similarity	NPC475225
0.8762	High Similarity	NPC477685
0.8762	High Similarity	NPC80800
0.8762	High Similarity	NPC12221
0.875	High Similarity	NPC260775
0.8727	High Similarity	NPC77772
0.8716	High Similarity	NPC473524
0.8716	High Similarity	NPC299568
0.8716	High Similarity	NPC186385
0.8704	High Similarity	NPC66834
0.8679	High Similarity	NPC471228
0.8679	High Similarity	NPC235762
0.8667	High Similarity	NPC130756
0.8667	High Similarity	NPC12931
0.8667	High Similarity	NPC70677
0.8667	High Similarity	NPC130103
0.8654	High Similarity	NPC79241
0.8654	High Similarity	NPC6597
0.8649	High Similarity	NPC228452
0.8609	High Similarity	NPC51341
0.8598	High Similarity	NPC475580
0.8596	High Similarity	NPC320864
0.8584	High Similarity	NPC232165
0.8571	High Similarity	NPC319803
0.8559	High Similarity	NPC224527
0.8558	High Similarity	NPC312132
0.8558	High Similarity	NPC259512
0.8532	High Similarity	NPC474352
0.8505	High Similarity	NPC269212
0.8491	Intermediate Similarity	NPC174911
0.8482	Intermediate Similarity	NPC302371
0.8468	Intermediate Similarity	NPC132720
0.8455	Intermediate Similarity	NPC95344
0.8455	Intermediate Similarity	NPC306295
0.8448	Intermediate Similarity	NPC121866
0.8447	Intermediate Similarity	NPC29373
0.8426	Intermediate Similarity	NPC323810
0.8426	Intermediate Similarity	NPC272029
0.8411	Intermediate Similarity	NPC252105
0.8396	Intermediate Similarity	NPC299762
0.8396	Intermediate Similarity	NPC33675
0.8393	Intermediate Similarity	NPC275627
0.8378	Intermediate Similarity	NPC19808
0.8378	Intermediate Similarity	NPC33728
0.8376	Intermediate Similarity	NPC325544
0.8376	Intermediate Similarity	NPC477037
0.8376	Intermediate Similarity	NPC318581
0.8364	Intermediate Similarity	NPC158253
0.8364	Intermediate Similarity	NPC233320
0.8364	Intermediate Similarity	NPC232523
0.8364	Intermediate Similarity	NPC204901
0.8349	Intermediate Similarity	NPC37802
0.8349	Intermediate Similarity	NPC117115
0.8333	Intermediate Similarity	NPC233827
0.8304	Intermediate Similarity	NPC296683
0.8302	Intermediate Similarity	NPC474073
0.8291	Intermediate Similarity	NPC471449
0.8288	Intermediate Similarity	NPC174981
0.8273	Intermediate Similarity	NPC99836
0.8273	Intermediate Similarity	NPC21594
0.8273	Intermediate Similarity	NPC201662
0.8273	Intermediate Similarity	NPC54765
0.8273	Intermediate Similarity	NPC12640
0.8273	Intermediate Similarity	NPC310456
0.8269	Intermediate Similarity	NPC147284
0.8269	Intermediate Similarity	NPC210497
0.8269	Intermediate Similarity	NPC3358
0.8269	Intermediate Similarity	NPC306884
0.8269	Intermediate Similarity	NPC94139
0.8269	Intermediate Similarity	NPC162314
0.8261	Intermediate Similarity	NPC246760
0.8261	Intermediate Similarity	NPC84999
0.8257	Intermediate Similarity	NPC227458
0.8257	Intermediate Similarity	NPC130817
0.8257	Intermediate Similarity	NPC218879
0.8257	Intermediate Similarity	NPC244513
0.8252	Intermediate Similarity	NPC192
0.8246	Intermediate Similarity	NPC23804
0.8246	Intermediate Similarity	NPC261343
0.823	Intermediate Similarity	NPC151537
0.8214	Intermediate Similarity	NPC98392
0.8205	Intermediate Similarity	NPC9592
0.8205	Intermediate Similarity	NPC206205
0.8205	Intermediate Similarity	NPC48781
0.8205	Intermediate Similarity	NPC469609
0.8205	Intermediate Similarity	NPC154030
0.8198	Intermediate Similarity	NPC151477
0.819	Intermediate Similarity	NPC245187
0.819	Intermediate Similarity	NPC152415
0.819	Intermediate Similarity	NPC76938
0.8182	Intermediate Similarity	NPC471350
0.8182	Intermediate Similarity	NPC138942
0.8173	Intermediate Similarity	NPC231150
0.8165	Intermediate Similarity	NPC222522
0.8165	Intermediate Similarity	NPC85479
0.8165	Intermediate Similarity	NPC302219
0.8165	Intermediate Similarity	NPC71002
0.8165	Intermediate Similarity	NPC24404
0.8165	Intermediate Similarity	NPC53051
0.8165	Intermediate Similarity	NPC94351
0.8165	Intermediate Similarity	NPC146798
0.8165	Intermediate Similarity	NPC249828
0.8165	Intermediate Similarity	NPC106396
0.8165	Intermediate Similarity	NPC242342
0.8165	Intermediate Similarity	NPC313030
0.8165	Intermediate Similarity	NPC168303
0.816	Intermediate Similarity	NPC473047
0.8158	Intermediate Similarity	NPC26615
0.8158	Intermediate Similarity	NPC98372
0.8158	Intermediate Similarity	NPC250323
0.8158	Intermediate Similarity	NPC474920
0.8158	Intermediate Similarity	NPC166995
0.8151	Intermediate Similarity	NPC129176
0.8151	Intermediate Similarity	NPC96423
0.8148	Intermediate Similarity	NPC166761
0.8148	Intermediate Similarity	NPC294741
0.8148	Intermediate Similarity	NPC10588
0.8142	Intermediate Similarity	NPC471535
0.8142	Intermediate Similarity	NPC13482
0.8136	Intermediate Similarity	NPC184302
0.8136	Intermediate Similarity	NPC323074
0.8136	Intermediate Similarity	NPC160235
0.8136	Intermediate Similarity	NPC151197
0.8136	Intermediate Similarity	NPC469644
0.8131	Intermediate Similarity	NPC88420
0.8131	Intermediate Similarity	NPC77492
0.8125	Intermediate Similarity	NPC68260
0.8125	Intermediate Similarity	NPC279887
0.8125	Intermediate Similarity	NPC11554
0.812	Intermediate Similarity	NPC69261
0.812	Intermediate Similarity	NPC304510
0.812	Intermediate Similarity	NPC238176
0.812	Intermediate Similarity	NPC187993
0.812	Intermediate Similarity	NPC172219
0.812	Intermediate Similarity	NPC33270
0.812	Intermediate Similarity	NPC477136
0.8115	Intermediate Similarity	NPC33654
0.8115	Intermediate Similarity	NPC470726
0.8113	Intermediate Similarity	NPC32714
0.8108	Intermediate Similarity	NPC67250
0.8108	Intermediate Similarity	NPC30416
0.8103	Intermediate Similarity	NPC473718
0.8099	Intermediate Similarity	NPC96940
0.8095	Intermediate Similarity	NPC55903
0.8091	Intermediate Similarity	NPC288411
0.8091	Intermediate Similarity	NPC241891
0.8091	Intermediate Similarity	NPC102216
0.8087	Intermediate Similarity	NPC123175
0.8087	Intermediate Similarity	NPC176730
0.8087	Intermediate Similarity	NPC190212
0.8087	Intermediate Similarity	NPC117846
0.8083	Intermediate Similarity	NPC168707
0.8083	Intermediate Similarity	NPC48623
0.808	Intermediate Similarity	NPC472793
0.8073	Intermediate Similarity	NPC147310
0.8073	Intermediate Similarity	NPC11280
0.8073	Intermediate Similarity	NPC166313
0.8073	Intermediate Similarity	NPC24407
0.8073	Intermediate Similarity	NPC137415
0.8073	Intermediate Similarity	NPC72947
0.8073	Intermediate Similarity	NPC294186
0.8073	Intermediate Similarity	NPC192032
0.8073	Intermediate Similarity	NPC284011
0.807	Intermediate Similarity	NPC476632
0.807	Intermediate Similarity	NPC95716
0.807	Intermediate Similarity	NPC4493
0.807	Intermediate Similarity	NPC165770
0.807	Intermediate Similarity	NPC225679
0.8067	Intermediate Similarity	NPC474131
0.8065	Intermediate Similarity	NPC211179
0.8065	Intermediate Similarity	NPC38604
0.8058	Intermediate Similarity	NPC27974
0.8053	Intermediate Similarity	NPC58865
0.8053	Intermediate Similarity	NPC26013
0.8053	Intermediate Similarity	NPC282855
0.8051	Intermediate Similarity	NPC190514
0.8051	Intermediate Similarity	NPC471671
0.8051	Intermediate Similarity	NPC206
0.8037	Intermediate Similarity	NPC292730
0.8037	Intermediate Similarity	NPC82664
0.8037	Intermediate Similarity	NPC216520

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 NPC54373 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	969
0.2-0.3	1445
0.3-0.4	2920
0.4-0.5	1827
0.5-0.6	1219
0.6-0.7	448
0.7-0.8	55
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8716	High Similarity	NPD4750	Phase 3
0.8667	High Similarity	NPD289	Clinical (unspecified phase)
0.8558	High Similarity	NPD288	Approved
0.8482	Intermediate Similarity	NPD7635	Approved
0.8462	Intermediate Similarity	NPD844	Approved
0.8261	Intermediate Similarity	NPD6671	Approved
0.8224	Intermediate Similarity	NPD3020	Approved
0.8099	Intermediate Similarity	NPD4749	Approved
0.8095	Intermediate Similarity	NPD845	Approved
0.7984	Intermediate Similarity	NPD2861	Phase 2
0.7944	Intermediate Similarity	NPD2860	Approved
0.7944	Intermediate Similarity	NPD2859	Approved
0.7909	Intermediate Similarity	NPD846	Approved
0.7909	Intermediate Similarity	NPD940	Approved
0.7895	Intermediate Similarity	NPD3022	Approved
0.7895	Intermediate Similarity	NPD3021	Approved
0.7886	Intermediate Similarity	NPD6696	Suspended
0.785	Intermediate Similarity	NPD2934	Approved
0.785	Intermediate Similarity	NPD2933	Approved
0.785	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD2342	Discontinued
0.7632	Intermediate Similarity	NPD1445	Approved
0.7632	Intermediate Similarity	NPD1444	Approved
0.7615	Intermediate Similarity	NPD1809	Phase 2
0.7603	Intermediate Similarity	NPD3091	Approved
0.7586	Intermediate Similarity	NPD1792	Phase 2
0.7583	Intermediate Similarity	NPD7340	Approved
0.7581	Intermediate Similarity	NPD2233	Approved
0.7581	Intermediate Similarity	NPD2230	Approved
0.7581	Intermediate Similarity	NPD2232	Approved
0.7578	Intermediate Similarity	NPD4625	Phase 3
0.752	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3092	Approved
0.75	Intermediate Similarity	NPD1242	Phase 1
0.748	Intermediate Similarity	NPD4059	Approved
0.748	Intermediate Similarity	NPD2932	Approved
0.7479	Intermediate Similarity	NPD2228	Approved
0.7479	Intermediate Similarity	NPD2229	Approved
0.7479	Intermediate Similarity	NPD2234	Approved
0.7479	Intermediate Similarity	NPD1398	Phase 1
0.7417	Intermediate Similarity	NPD497	Approved
0.7402	Intermediate Similarity	NPD3094	Phase 2
0.7364	Intermediate Similarity	NPD4908	Phase 1
0.736	Intermediate Similarity	NPD1610	Phase 2
0.7339	Intermediate Similarity	NPD4626	Approved
0.7339	Intermediate Similarity	NPD3019	Approved
0.7333	Intermediate Similarity	NPD495	Approved
0.7333	Intermediate Similarity	NPD496	Approved
0.7333	Intermediate Similarity	NPD498	Approved
0.7333	Intermediate Similarity	NPD111	Approved
0.7328	Intermediate Similarity	NPD968	Approved
0.728	Intermediate Similarity	NPD3496	Discontinued
0.7273	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2238	Phase 2
0.7252	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1201	Approved
0.72	Intermediate Similarity	NPD3095	Discontinued
0.719	Intermediate Similarity	NPD5283	Phase 1
0.7177	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3027	Phase 3
0.7167	Intermediate Similarity	NPD228	Approved
0.7167	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5736	Approved
0.7154	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6099	Approved
0.7132	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6100	Approved
0.712	Intermediate Similarity	NPD4093	Discontinued
0.7077	Intermediate Similarity	NPD4624	Approved
0.7063	Intermediate Similarity	NPD1778	Approved
0.7063	Intermediate Similarity	NPD1751	Approved
0.7063	Intermediate Similarity	NPD2667	Approved
0.7063	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2668	Approved
0.705	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD1548	Phase 1
0.704	Intermediate Similarity	NPD5303	Approved
0.704	Intermediate Similarity	NPD5304	Approved
0.7031	Intermediate Similarity	NPD1608	Approved
0.7016	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD1470	Approved
0.6992	Remote Similarity	NPD1793	Approved
0.6992	Remote Similarity	NPD1791	Approved
0.6992	Remote Similarity	NPD9614	Approved
0.6992	Remote Similarity	NPD9618	Approved
0.699	Remote Similarity	NPD9088	Approved
0.6984	Remote Similarity	NPD5691	Approved
0.697	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1611	Approved
0.694	Remote Similarity	NPD6663	Approved
0.6935	Remote Similarity	NPD709	Approved
0.6929	Remote Similarity	NPD4589	Approved
0.6929	Remote Similarity	NPD2286	Discontinued
0.6923	Remote Similarity	NPD9500	Approved
0.6923	Remote Similarity	NPD8651	Approved
0.6923	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD2684	Approved
0.6912	Remote Similarity	NPD4097	Suspended
0.6909	Remote Similarity	NPD9295	Approved
0.6899	Remote Similarity	NPD2231	Phase 2
0.6899	Remote Similarity	NPD2235	Phase 2
0.6897	Remote Similarity	NPD3028	Approved
0.6894	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2237	Approved
0.6889	Remote Similarity	NPD1613	Approved
0.6889	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2935	Discontinued
0.687	Remote Similarity	NPD4103	Phase 2
0.687	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.687	Remote Similarity	NPD9273	Approved
0.686	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4659	Approved
0.6842	Remote Similarity	NPD596	Approved
0.6842	Remote Similarity	NPD600	Approved
0.6835	Remote Similarity	NPD5762	Approved
0.6835	Remote Similarity	NPD5763	Approved
0.6833	Remote Similarity	NPD290	Approved
0.6831	Remote Similarity	NPD3300	Phase 2
0.6829	Remote Similarity	NPD1138	Approved
0.6825	Remote Similarity	NPD9615	Approved
0.6825	Remote Similarity	NPD9616	Approved
0.6825	Remote Similarity	NPD9613	Approved
0.6825	Remote Similarity	NPD7644	Approved
0.6822	Remote Similarity	NPD1091	Approved
0.6822	Remote Similarity	NPD422	Phase 1
0.6818	Remote Similarity	NPD6584	Phase 3
0.6818	Remote Similarity	NPD2194	Approved
0.6818	Remote Similarity	NPD2195	Approved
0.6812	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7157	Approved
0.6797	Remote Similarity	NPD17	Approved
0.6797	Remote Similarity	NPD9384	Approved
0.6797	Remote Similarity	NPD9381	Approved
0.6794	Remote Similarity	NPD1283	Approved
0.6772	Remote Similarity	NPD7741	Discontinued
0.6772	Remote Similarity	NPD316	Approved
0.6772	Remote Similarity	NPD7330	Discontinued
0.6767	Remote Similarity	NPD1712	Approved
0.6767	Remote Similarity	NPD3636	Approved
0.6767	Remote Similarity	NPD3635	Approved
0.6767	Remote Similarity	NPD3637	Approved
0.6765	Remote Similarity	NPD3620	Phase 2
0.6765	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1137	Approved
0.6748	Remote Similarity	NPD1139	Approved
0.6746	Remote Similarity	NPD7636	Approved
0.6744	Remote Similarity	NPD1981	Approved
0.6744	Remote Similarity	NPD1983	Approved
0.6744	Remote Similarity	NPD3023	Approved
0.6744	Remote Similarity	NPD3026	Approved
0.6744	Remote Similarity	NPD1980	Approved
0.6742	Remote Similarity	NPD2797	Approved
0.6736	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD9610	Approved
0.6723	Remote Similarity	NPD9608	Approved
0.6721	Remote Similarity	NPD5451	Approved
0.6719	Remote Similarity	NPD1651	Approved
0.6719	Remote Similarity	NPD3024	Approved
0.6719	Remote Similarity	NPD5585	Approved
0.6719	Remote Similarity	NPD3025	Approved
0.6718	Remote Similarity	NPD5327	Phase 3
0.6718	Remote Similarity	NPD9622	Approved
0.6718	Remote Similarity	NPD1755	Approved
0.6716	Remote Similarity	NPD2605	Approved
0.6716	Remote Similarity	NPD2606	Approved
0.6715	Remote Similarity	NPD5735	Approved
0.6714	Remote Similarity	NPD4726	Approved
0.6714	Remote Similarity	NPD4721	Approved
0.6714	Remote Similarity	NPD4725	Approved
0.6695	Remote Similarity	NPD4818	Approved
0.6695	Remote Similarity	NPD4817	Approved
0.6694	Remote Similarity	NPD7843	Approved
0.6694	Remote Similarity	NPD9377	Approved
0.6694	Remote Similarity	NPD9379	Approved
0.6693	Remote Similarity	NPD856	Approved
0.6693	Remote Similarity	NPD16	Approved
0.6692	Remote Similarity	NPD3705	Approved
0.6691	Remote Similarity	NPD839	Approved
0.6691	Remote Similarity	NPD6407	Approved
0.6691	Remote Similarity	NPD6405	Approved
0.6691	Remote Similarity	NPD840	Approved
0.669	Remote Similarity	NPD6090	Discontinued
0.6667	Remote Similarity	NPD6387	Discontinued
0.6667	Remote Similarity	NPD5156	Approved
0.6667	Remote Similarity	NPD5155	Approved
0.6667	Remote Similarity	NPD6353	Approved
0.6642	Remote Similarity	NPD3018	Phase 2
0.6642	Remote Similarity	NPD4140	Approved
0.6641	Remote Similarity	NPD2561	Approved
0.6641	Remote Similarity	NPD9545	Approved
0.6641	Remote Similarity	NPD2562	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