NPASS Compound

Structure

NPC474352 OpenBabel07101718222D 31 31 0 0 1 0 0 0 0 0999 V2000 -2.5981 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 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 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 7.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 0.0000 C 0 0 0 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 7.5000 0.0000 C 0 0 2 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 7.0000 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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 13 1 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 11 21 2 0 0 0 0 12 14 2 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 27 1 0 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 21 1 0 0 0 0 16 24 1 0 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 23 1 0 0 0 0 18 25 2 0 0 0 0 22 25 1 0 0 0 0 23 26 2 0 0 0 0 24 28 1 6 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 27 6 1 6 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.29
Volume:	483.697
LogP:	5.915
LogD:	4.53
LogS:	-3.978
# Rotatable Bonds:	11
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	4.146
Fsp3:	0.481
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.768
MDCK Permeability:	2.094823503284715e-05
Pgp-inhibitor:	0.663
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.158
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	98.51534271240234%
Volume Distribution (VD):	0.81
Pgp-substrate:	1.3552324771881104%

ADMET: Metabolism

CYP1A2-inhibitor:	0.35
CYP1A2-substrate:	0.205
CYP2C19-inhibitor:	0.504
CYP2C19-substrate:	0.464
CYP2C9-inhibitor:	0.637
CYP2C9-substrate:	0.907
CYP2D6-inhibitor:	0.906
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.857
CYP3A4-substrate:	0.205

ADMET: Excretion

Clearance (CL):	12.673
Half-life (T1/2):	0.477

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.921
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.822
Carcinogencity:	0.083
Eye Corrosion:	0.003
Eye Irritation:	0.484
Respiratory Toxicity:	0.405

Download Data

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

Natural Product: NPC474352

Natural Product ID:	NPC474352
*Common Name:**	Chabrolohydroxybenzoquinone F
IUPAC Name:	2-[(1Z,3S,6E,9S,10E)-3,9-dihydroxy-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraenyl]-5-methylbenzene-1,4-diol
Synonyms:	Chabrolohydroxybenzoquinone F
Standard InCHIKey:	UHUUMLHCKBNMSI-YQBDCGJDSA-N
Standard InCHI:	InChI=1S/C27H40O4/c1-19(2)9-7-10-20(3)15-24(28)16-21(4)11-8-13-27(6,31)14-12-23-18-25(29)22(5)17-26(23)30/h9,11-12,14-15,17-18,24,28-31H,7-8,10,13,16H2,1-6H3/b14-12-,20-15+,21-11+/t24-,27+/m1/s1
SMILES:	CC1=CC(=C(C=C1O)C=CC(C)(CCC=C(C)CC(C=C(C)CCC=C(C)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465562
PubChem CID:	44566532
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO16934	Nephthea chabrolii	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16309317]
NPO16934	Nephthea chabrolii	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	42300.0	nM	PMID[572911]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	44400.0	nM	PMID[572911]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	46700.0	nM	PMID[572911]

☑ 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 NPC474352 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	240
0.1-0.2	1320
0.2-0.3	4405
0.3-0.4	13250
0.4-0.5	7079
0.5-0.6	10613
0.6-0.7	4690
0.7-0.8	938
0.8-0.85	108
0.85-0.9	40
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9495	High Similarity	NPC80800
0.9192	High Similarity	NPC475078
0.9109	High Similarity	NPC477685
0.91	High Similarity	NPC260775
0.9048	High Similarity	NPC473524
0.902	High Similarity	NPC471228
0.902	High Similarity	NPC235762
0.901	High Similarity	NPC130756
0.901	High Similarity	NPC70677
0.901	High Similarity	NPC174911
0.901	High Similarity	NPC12931
0.901	High Similarity	NPC129373
0.901	High Similarity	NPC248396
0.901	High Similarity	NPC48730
0.9	High Similarity	NPC152097
0.8942	High Similarity	NPC53740
0.8932	High Similarity	NPC475225
0.8909	High Similarity	NPC320864
0.8857	High Similarity	NPC66834
0.8846	High Similarity	NPC47284
0.8835	High Similarity	NPC108497
0.8829	High Similarity	NPC206205
0.8824	High Similarity	NPC130103
0.8812	High Similarity	NPC474073
0.8812	High Similarity	NPC88420
0.8796	High Similarity	NPC302371
0.8788	High Similarity	NPC29373
0.8785	High Similarity	NPC471535
0.8687	High Similarity	NPC231150
0.8641	High Similarity	NPC72729
0.8636	High Similarity	NPC473931
0.8636	High Similarity	NPC474050
0.8636	High Similarity	NPC474114
0.8624	High Similarity	NPC228452
0.8586	High Similarity	NPC312304
0.8585	High Similarity	NPC469913
0.8585	High Similarity	NPC155072
0.8571	High Similarity	NPC130817
0.8558	High Similarity	NPC252105
0.8545	High Similarity	NPC28784
0.8545	High Similarity	NPC296144
0.8532	High Similarity	NPC54373
0.8532	High Similarity	NPC469912
0.8519	High Similarity	NPC98392
0.8468	Intermediate Similarity	NPC197513
0.8462	Intermediate Similarity	NPC294741
0.8447	Intermediate Similarity	NPC6597
0.8447	Intermediate Similarity	NPC79241
0.844	Intermediate Similarity	NPC132720
0.8421	Intermediate Similarity	NPC151197
0.8421	Intermediate Similarity	NPC476020
0.8416	Intermediate Similarity	NPC147284
0.8416	Intermediate Similarity	NPC306884
0.8416	Intermediate Similarity	NPC94139
0.8416	Intermediate Similarity	NPC3358
0.8416	Intermediate Similarity	NPC210497
0.8416	Intermediate Similarity	NPC162314
0.8396	Intermediate Similarity	NPC323810
0.8396	Intermediate Similarity	NPC272029
0.8393	Intermediate Similarity	NPC474486
0.8393	Intermediate Similarity	NPC232165
0.8378	Intermediate Similarity	NPC261343
0.8365	Intermediate Similarity	NPC33675
0.8365	Intermediate Similarity	NPC299762
0.835	Intermediate Similarity	NPC312132
0.835	Intermediate Similarity	NPC259512
0.8348	Intermediate Similarity	NPC325544
0.8348	Intermediate Similarity	NPC477037
0.8348	Intermediate Similarity	NPC318581
0.8333	Intermediate Similarity	NPC233320
0.8333	Intermediate Similarity	NPC61033
0.8333	Intermediate Similarity	NPC232523
0.8333	Intermediate Similarity	NPC204901
0.8333	Intermediate Similarity	NPC320439
0.8333	Intermediate Similarity	NPC9592
0.8333	Intermediate Similarity	NPC305603
0.8333	Intermediate Similarity	NPC158253
0.8333	Intermediate Similarity	NPC48781
0.8318	Intermediate Similarity	NPC471350
0.8302	Intermediate Similarity	NPC269212
0.8288	Intermediate Similarity	NPC62867
0.8288	Intermediate Similarity	NPC177962
0.8273	Intermediate Similarity	NPC208229
0.8261	Intermediate Similarity	NPC323074
0.8261	Intermediate Similarity	NPC121866
0.8257	Intermediate Similarity	NPC169450
0.8257	Intermediate Similarity	NPC241549
0.8241	Intermediate Similarity	NPC12640
0.8241	Intermediate Similarity	NPC201662
0.8241	Intermediate Similarity	NPC310456
0.8241	Intermediate Similarity	NPC99836
0.8235	Intermediate Similarity	NPC325292
0.8235	Intermediate Similarity	NPC138117
0.8224	Intermediate Similarity	NPC475580
0.8224	Intermediate Similarity	NPC93831
0.8218	Intermediate Similarity	NPC47950
0.8218	Intermediate Similarity	NPC192
0.8214	Intermediate Similarity	NPC319803
0.8208	Intermediate Similarity	NPC101025
0.8208	Intermediate Similarity	NPC12221
0.8208	Intermediate Similarity	NPC471578
0.82	Intermediate Similarity	NPC27974
0.8198	Intermediate Similarity	NPC77772
0.8198	Intermediate Similarity	NPC266937
0.8198	Intermediate Similarity	NPC470770
0.8198	Intermediate Similarity	NPC228609
0.819	Intermediate Similarity	NPC232295
0.819	Intermediate Similarity	NPC128723
0.8182	Intermediate Similarity	NPC26013
0.8182	Intermediate Similarity	NPC282855
0.8158	Intermediate Similarity	NPC92
0.8158	Intermediate Similarity	NPC469663
0.8158	Intermediate Similarity	NPC141001
0.8155	Intermediate Similarity	NPC245187
0.8148	Intermediate Similarity	NPC37802
0.8136	Intermediate Similarity	NPC46586
0.8136	Intermediate Similarity	NPC204535
0.8131	Intermediate Similarity	NPC233827
0.8125	Intermediate Similarity	NPC26615
0.8125	Intermediate Similarity	NPC474920
0.8125	Intermediate Similarity	NPC228425
0.8103	Intermediate Similarity	NPC32152
0.8103	Intermediate Similarity	NPC160235
0.81	Intermediate Similarity	NPC407
0.81	Intermediate Similarity	NPC307235
0.8091	Intermediate Similarity	NPC279887
0.8091	Intermediate Similarity	NPC68260
0.8091	Intermediate Similarity	NPC306295
0.8091	Intermediate Similarity	NPC262365
0.8087	Intermediate Similarity	NPC477136
0.8081	Intermediate Similarity	NPC150837
0.8081	Intermediate Similarity	NPC286904
0.8077	Intermediate Similarity	NPC32714
0.8077	Intermediate Similarity	NPC313650
0.8067	Intermediate Similarity	NPC474130
0.8067	Intermediate Similarity	NPC261992
0.8056	Intermediate Similarity	NPC227458
0.8056	Intermediate Similarity	NPC244513
0.8056	Intermediate Similarity	NPC218879
0.8053	Intermediate Similarity	NPC190212
0.8039	Intermediate Similarity	NPC55561
0.8039	Intermediate Similarity	NPC300017
0.8037	Intermediate Similarity	NPC91461
0.8037	Intermediate Similarity	NPC7686
0.8037	Intermediate Similarity	NPC40258
0.8036	Intermediate Similarity	NPC275627
0.8036	Intermediate Similarity	NPC308689
0.8034	Intermediate Similarity	NPC223451
0.8034	Intermediate Similarity	NPC474131
0.802	Intermediate Similarity	NPC104216
0.8019	Intermediate Similarity	NPC132078
0.8019	Intermediate Similarity	NPC78119
0.8019	Intermediate Similarity	NPC216468
0.8019	Intermediate Similarity	NPC51333
0.8018	Intermediate Similarity	NPC33728
0.8018	Intermediate Similarity	NPC19808
0.8018	Intermediate Similarity	NPC316052
0.8017	Intermediate Similarity	NPC283616
0.8	Intermediate Similarity	NPC219112
0.8	Intermediate Similarity	NPC308311
0.8	Intermediate Similarity	NPC154256
0.8	Intermediate Similarity	NPC290470
0.8	Intermediate Similarity	NPC308828
0.8	Intermediate Similarity	NPC38893
0.8	Intermediate Similarity	NPC155393
0.8	Intermediate Similarity	NPC477137
0.7983	Intermediate Similarity	NPC188997
0.7982	Intermediate Similarity	NPC471534
0.7982	Intermediate Similarity	NPC41851
0.7982	Intermediate Similarity	NPC117115
0.7982	Intermediate Similarity	NPC114918
0.7982	Intermediate Similarity	NPC12656
0.7981	Intermediate Similarity	NPC152415
0.7981	Intermediate Similarity	NPC76938
0.7965	Intermediate Similarity	NPC166995
0.7963	Intermediate Similarity	NPC85479
0.7963	Intermediate Similarity	NPC222522
0.7963	Intermediate Similarity	NPC249828
0.7963	Intermediate Similarity	NPC196479
0.7963	Intermediate Similarity	NPC168303
0.7963	Intermediate Similarity	NPC53051
0.7963	Intermediate Similarity	NPC94351
0.7963	Intermediate Similarity	NPC24404
0.7963	Intermediate Similarity	NPC313030
0.7963	Intermediate Similarity	NPC242342
0.7963	Intermediate Similarity	NPC106396
0.7963	Intermediate Similarity	NPC146798
0.7963	Intermediate Similarity	NPC302219
0.7963	Intermediate Similarity	NPC62351
0.7963	Intermediate Similarity	NPC71002
0.7961	Intermediate Similarity	NPC270547
0.7949	Intermediate Similarity	NPC469644
0.7949	Intermediate Similarity	NPC471449
0.7946	Intermediate Similarity	NPC174096
0.7946	Intermediate Similarity	NPC120982
0.7946	Intermediate Similarity	NPC147634
0.7946	Intermediate Similarity	NPC44732
0.7946	Intermediate Similarity	NPC79793
0.7946	Intermediate Similarity	NPC226401
0.7944	Intermediate Similarity	NPC166761

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 NPC474352 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	911
0.2-0.3	1707
0.3-0.4	2986
0.4-0.5	1796
0.5-0.6	1120
0.6-0.7	361
0.7-0.8	50
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8614	High Similarity	NPD844	Approved
0.8462	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.835	Intermediate Similarity	NPD288	Approved
0.8288	Intermediate Similarity	NPD7635	Approved
0.807	Intermediate Similarity	NPD6671	Approved
0.7857	Intermediate Similarity	NPD4750	Phase 3
0.781	Intermediate Similarity	NPD2934	Approved
0.781	Intermediate Similarity	NPD2933	Approved
0.7736	Intermediate Similarity	NPD2859	Approved
0.7736	Intermediate Similarity	NPD2860	Approved
0.7714	Intermediate Similarity	NPD845	Approved
0.7685	Intermediate Similarity	NPD3020	Approved
0.7642	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD111	Approved
0.7563	Intermediate Similarity	NPD3091	Approved
0.7545	Intermediate Similarity	NPD940	Approved
0.7545	Intermediate Similarity	NPD846	Approved
0.7544	Intermediate Similarity	NPD3022	Approved
0.7544	Intermediate Similarity	NPD3021	Approved
0.7522	Intermediate Similarity	NPD2342	Discontinued
0.7521	Intermediate Similarity	NPD9618	Approved
0.7521	Intermediate Similarity	NPD9614	Approved
0.7521	Intermediate Similarity	NPD3496	Discontinued
0.7436	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD968	Approved
0.7419	Intermediate Similarity	NPD6696	Suspended
0.7414	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1809	Phase 2
0.7373	Intermediate Similarity	NPD497	Approved
0.7368	Intermediate Similarity	NPD290	Approved
0.736	Intermediate Similarity	NPD3094	Phase 2
0.7333	Intermediate Similarity	NPD9616	Approved
0.7333	Intermediate Similarity	NPD9613	Approved
0.7333	Intermediate Similarity	NPD9615	Approved
0.7317	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3092	Approved
0.7317	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1242	Phase 1
0.7295	Intermediate Similarity	NPD3095	Discontinued
0.7288	Intermediate Similarity	NPD495	Approved
0.7288	Intermediate Similarity	NPD498	Approved
0.7288	Intermediate Similarity	NPD496	Approved
0.7281	Intermediate Similarity	NPD1444	Approved
0.7281	Intermediate Similarity	NPD1445	Approved
0.7273	Intermediate Similarity	NPD316	Approved
0.7273	Intermediate Similarity	NPD9088	Approved
0.725	Intermediate Similarity	NPD7340	Approved
0.7244	Intermediate Similarity	NPD2861	Phase 2
0.7209	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD600	Approved
0.7188	Intermediate Similarity	NPD596	Approved
0.7172	Intermediate Similarity	NPD9294	Approved
0.7165	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD839	Approved
0.7154	Intermediate Similarity	NPD4626	Approved
0.7154	Intermediate Similarity	NPD840	Approved
0.7154	Intermediate Similarity	NPD1778	Approved
0.7143	Intermediate Similarity	NPD1398	Phase 1
0.7119	Intermediate Similarity	NPD228	Approved
0.7117	Intermediate Similarity	NPD9273	Approved
0.7107	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD1792	Phase 2
0.7063	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4749	Approved
0.7059	Intermediate Similarity	NPD7843	Approved
0.7025	Intermediate Similarity	NPD7157	Approved
0.7018	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD9500	Approved
0.7016	Intermediate Similarity	NPD9381	Approved
0.7016	Intermediate Similarity	NPD4059	Approved
0.7016	Intermediate Similarity	NPD9384	Approved
0.7009	Intermediate Similarity	NPD9295	Approved
0.7009	Intermediate Similarity	NPD2684	Approved
0.7	Intermediate Similarity	NPD2234	Approved
0.7	Intermediate Similarity	NPD2229	Approved
0.7	Intermediate Similarity	NPD2228	Approved
0.7	Intermediate Similarity	NPD3027	Phase 3
0.6992	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD3028	Approved
0.6984	Remote Similarity	NPD2233	Approved
0.6984	Remote Similarity	NPD2235	Phase 2
0.6984	Remote Similarity	NPD2231	Phase 2
0.6984	Remote Similarity	NPD2230	Approved
0.6984	Remote Similarity	NPD2232	Approved
0.6977	Remote Similarity	NPD5736	Approved
0.696	Remote Similarity	NPD1983	Approved
0.696	Remote Similarity	NPD1980	Approved
0.696	Remote Similarity	NPD1981	Approved
0.6935	Remote Similarity	NPD5691	Approved
0.6935	Remote Similarity	NPD1357	Approved
0.6929	Remote Similarity	NPD9622	Approved
0.6911	Remote Similarity	NPD856	Approved
0.6911	Remote Similarity	NPD16	Approved
0.6905	Remote Similarity	NPD1091	Approved
0.6891	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.688	Remote Similarity	NPD3019	Approved
0.688	Remote Similarity	NPD2932	Approved
0.688	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.687	Remote Similarity	NPD4625	Phase 3
0.6869	Remote Similarity	NPD9087	Approved
0.686	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2238	Phase 2
0.681	Remote Similarity	NPD9610	Approved
0.681	Remote Similarity	NPD9608	Approved
0.6803	Remote Similarity	NPD1793	Approved
0.6803	Remote Similarity	NPD1791	Approved
0.6777	Remote Similarity	NPD9377	Approved
0.6777	Remote Similarity	NPD9379	Approved
0.6774	Remote Similarity	NPD318	Approved
0.6774	Remote Similarity	NPD317	Approved
0.6772	Remote Similarity	NPD1611	Approved
0.6769	Remote Similarity	NPD9621	Approved
0.6769	Remote Similarity	NPD602	Approved
0.6769	Remote Similarity	NPD599	Approved
0.6769	Remote Similarity	NPD859	Approved
0.6769	Remote Similarity	NPD9619	Approved
0.6769	Remote Similarity	NPD858	Approved
0.6769	Remote Similarity	NPD9620	Approved
0.6767	Remote Similarity	NPD6663	Approved
0.6767	Remote Similarity	NPD6405	Approved
0.6767	Remote Similarity	NPD6407	Approved
0.6746	Remote Similarity	NPD2286	Discontinued
0.6741	Remote Similarity	NPD2568	Approved
0.6741	Remote Similarity	NPD5314	Approved
0.6741	Remote Similarity	NPD6653	Approved
0.6721	Remote Similarity	NPD5283	Phase 1
0.6719	Remote Similarity	NPD2562	Approved
0.6719	Remote Similarity	NPD2561	Approved
0.6718	Remote Similarity	NPD2237	Approved
0.6716	Remote Similarity	NPD3059	Approved
0.6716	Remote Similarity	NPD3062	Approved
0.6716	Remote Similarity	NPD3061	Approved
0.6716	Remote Similarity	NPD4060	Phase 1
0.6716	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1613	Approved
0.6715	Remote Similarity	NPD2935	Discontinued
0.6694	Remote Similarity	NPD9493	Approved
0.6694	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1133	Approved
0.6692	Remote Similarity	NPD1134	Approved
0.6692	Remote Similarity	NPD1135	Approved
0.6692	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1129	Approved
0.6692	Remote Similarity	NPD597	Approved
0.6692	Remote Similarity	NPD4103	Phase 2
0.6692	Remote Similarity	NPD601	Approved
0.6692	Remote Similarity	NPD1131	Approved
0.6692	Remote Similarity	NPD598	Approved
0.6691	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD7266	Discontinued
0.6667	Remote Similarity	NPD4659	Approved
0.6667	Remote Similarity	NPD4093	Discontinued
0.6667	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD5762	Approved
0.6643	Remote Similarity	NPD6090	Discontinued
0.6642	Remote Similarity	NPD1130	Approved
0.6642	Remote Similarity	NPD1136	Approved
0.6642	Remote Similarity	NPD7743	Approved
0.6642	Remote Similarity	NPD1132	Approved
0.6642	Remote Similarity	NPD7742	Approved
0.6641	Remote Similarity	NPD1201	Approved
0.6641	Remote Similarity	NPD558	Phase 2
0.6641	Remote Similarity	NPD6584	Phase 3
0.6639	Remote Similarity	NPD821	Approved
0.6614	Remote Similarity	NPD4589	Approved
0.6614	Remote Similarity	NPD1751	Approved
0.6613	Remote Similarity	NPD709	Approved
0.6593	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3620	Phase 2
0.6587	Remote Similarity	NPD1548	Phase 1
0.6587	Remote Similarity	NPD1759	Phase 1
0.6587	Remote Similarity	NPD5304	Approved
0.6587	Remote Similarity	NPD5303	Approved
0.6587	Remote Similarity	NPD7330	Discontinued
0.6583	Remote Similarity	NPD9266	Approved
0.6583	Remote Similarity	NPD74	Approved
0.6581	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7985	Registered
0.6565	Remote Similarity	NPD1470	Approved
0.6555	Remote Similarity	NPD3134	Approved
0.6544	Remote Similarity	NPD5735	Approved
0.6538	Remote Similarity	NPD5327	Phase 3
0.6538	Remote Similarity	NPD3685	Discontinued
0.6535	Remote Similarity	NPD5585	Approved
0.6532	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD9609	Approved
0.6522	Remote Similarity	NPD9495	Approved
0.6522	Remote Similarity	NPD9612	Approved
0.6522	Remote Similarity	NPD9611	Approved
0.6515	Remote Similarity	NPD3690	Phase 2
0.6515	Remote Similarity	NPD4624	Approved
0.6515	Remote Similarity	NPD3691	Phase 2
0.6512	Remote Similarity	NPD1610	Phase 2
0.6509	Remote Similarity	NPD9089	Approved
0.6508	Remote Similarity	NPD1758	Phase 1

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