NPASS Compound

Structure

NPC469913 OpenBabel07101719522D 30 30 0 0 1 0 0 0 0 0999 V2000 -5.1962 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 -3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 -2.5981 -2.5000 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 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 -4.3301 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -7.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 2 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -3.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 5 23 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 16 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 27 1 0 0 0 0 17 27 1 0 0 0 0 18 23 1 0 0 0 0 18 25 2 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 21 3 1 6 0 0 0 22 4 1 6 0 0 0 23 26 2 0 0 0 0 24 26 1 0 0 0 0 25 28 1 0 0 0 0 26 29 1 0 0 0 0 27 6 1 6 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.36
Volume:	485.453
LogP:	7.848
LogD:	6.229
LogS:	-4.931
# Rotatable Bonds:	15
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.257
Synthetic Accessibility Score:	3.721
Fsp3:	0.778
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.9
MDCK Permeability:	1.3757025044469628e-05
Pgp-inhibitor:	0.083
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.534
Plasma Protein Binding (PPB):	99.9181900024414%
Volume Distribution (VD):	2.799
Pgp-substrate:	2.0962741374969482%

ADMET: Metabolism

CYP1A2-inhibitor:	0.184
CYP1A2-substrate:	0.21
CYP2C19-inhibitor:	0.627
CYP2C19-substrate:	0.408
CYP2C9-inhibitor:	0.212
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.734
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.423
CYP3A4-substrate:	0.102

ADMET: Excretion

Clearance (CL):	7.885
Half-life (T1/2):	0.265

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.037
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.741
Skin Sensitization:	0.962
Carcinogencity:	0.022
Eye Corrosion:	0.847
Eye Irritation:	0.939
Respiratory Toxicity:	0.177

Download Data

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

Natural Product: NPC469913

Natural Product ID:	NPC469913
*Common Name:**	Gama-Tocopherylhydroquinone
IUPAC Name:	2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-6-methylbenzene-1,4-diol
Synonyms:	Gama-Tocopherylhydroquinone
Standard InCHIKey:	IVKONZZPWXVIBM-VHFRWLAGSA-N
Standard InCHI:	InChI=1S/C27H48O3/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6,30)17-15-24-19-25(28)18-23(5)26(24)29/h18-22,28-30H,7-17H2,1-6H3/t21-,22-,27-/m1/s1
SMILES:	CC1=CC(=CC(=C1O)CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1258197
PubChem CID:	49765075
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
NPO33001	macroalgae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20801038]

☑ 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	3

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	IC50	>	100000.0	nM	PMID[570256]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	MIC	=	220000.0	nM	PMID[570256]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	500000.0	nM	PMID[570256]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	500000.0	nM	PMID[570256]

☑ 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 NPC469913 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	286
0.1-0.2	1552
0.2-0.3	4167
0.3-0.4	13683
0.4-0.5	6774
0.5-0.6	10173
0.6-0.7	4887
0.7-0.8	912
0.8-0.85	169
0.85-0.9	74
0.9-0.95	19
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9515	High Similarity	NPC469912
0.9495	High Similarity	NPC108497
0.9293	High Similarity	NPC129373
0.9293	High Similarity	NPC248396
0.9293	High Similarity	NPC48730
0.92	High Similarity	NPC477685
0.9192	High Similarity	NPC260775
0.9109	High Similarity	NPC269212
0.91	High Similarity	NPC12931
0.91	High Similarity	NPC70677
0.91	High Similarity	NPC130756
0.9091	High Similarity	NPC152097
0.9091	High Similarity	NPC475078
0.901	High Similarity	NPC80800
0.8962	High Similarity	NPC54373
0.8952	High Similarity	NPC282855
0.8952	High Similarity	NPC26013
0.8899	High Similarity	NPC141001
0.8868	High Similarity	NPC208229
0.8857	High Similarity	NPC279887
0.8857	High Similarity	NPC68260
0.8846	High Similarity	NPC53740
0.8846	High Similarity	NPC155072
0.8835	High Similarity	NPC272029
0.8774	High Similarity	NPC473524
0.8762	High Similarity	NPC320439
0.875	High Similarity	NPC47284
0.8725	High Similarity	NPC130103
0.8725	High Similarity	NPC72729
0.8716	High Similarity	NPC471534
0.8704	High Similarity	NPC177962
0.8704	High Similarity	NPC62867
0.8687	High Similarity	NPC94139
0.8687	High Similarity	NPC306884
0.8687	High Similarity	NPC162314
0.8687	High Similarity	NPC147284
0.8687	High Similarity	NPC29373
0.8687	High Similarity	NPC210497
0.8687	High Similarity	NPC3358
0.8679	High Similarity	NPC95344
0.8667	High Similarity	NPC12640
0.8667	High Similarity	NPC99836
0.8667	High Similarity	NPC201662
0.8661	High Similarity	NPC476020
0.8654	High Similarity	NPC475580
0.8649	High Similarity	NPC187993
0.8649	High Similarity	NPC238176
0.8641	High Similarity	NPC12221
0.8641	High Similarity	NPC24407
0.8641	High Similarity	NPC166313
0.8641	High Similarity	NPC147310
0.8641	High Similarity	NPC11280
0.8641	High Similarity	NPC137415
0.8641	High Similarity	NPC294186
0.8641	High Similarity	NPC192032
0.8624	High Similarity	NPC296144
0.8624	High Similarity	NPC28784
0.8611	High Similarity	NPC470770
0.8611	High Similarity	NPC266937
0.8611	High Similarity	NPC77772
0.8585	High Similarity	NPC232523
0.8585	High Similarity	NPC158253
0.8585	High Similarity	NPC474352
0.8585	High Similarity	NPC204901
0.8571	High Similarity	NPC37802
0.8571	High Similarity	NPC117115
0.8559	High Similarity	NPC69539
0.8558	High Similarity	NPC249828
0.8558	High Similarity	NPC471228
0.8558	High Similarity	NPC168303
0.8558	High Similarity	NPC71002
0.8558	High Similarity	NPC235762
0.8558	High Similarity	NPC53051
0.8558	High Similarity	NPC106396
0.8558	High Similarity	NPC242342
0.8558	High Similarity	NPC94351
0.8558	High Similarity	NPC302219
0.8558	High Similarity	NPC222522
0.8558	High Similarity	NPC146798
0.8558	High Similarity	NPC85479
0.8558	High Similarity	NPC313030
0.8558	High Similarity	NPC24404
0.8545	High Similarity	NPC474050
0.8545	High Similarity	NPC473931
0.8545	High Similarity	NPC114918
0.8545	High Similarity	NPC474114
0.8532	High Similarity	NPC302371
0.8529	High Similarity	NPC79241
0.8529	High Similarity	NPC6597
0.8529	High Similarity	NPC77492
0.8519	High Similarity	NPC132720
0.8515	High Similarity	NPC222146
0.8491	Intermediate Similarity	NPC54765
0.8485	Intermediate Similarity	NPC192
0.8476	Intermediate Similarity	NPC227458
0.8476	Intermediate Similarity	NPC244513
0.8476	Intermediate Similarity	NPC218879
0.8476	Intermediate Similarity	NPC475225
0.8469	Intermediate Similarity	NPC19680
0.8462	Intermediate Similarity	NPC284011
0.8462	Intermediate Similarity	NPC252105
0.8462	Intermediate Similarity	NPC72947
0.8455	Intermediate Similarity	NPC263753
0.844	Intermediate Similarity	NPC4493
0.844	Intermediate Similarity	NPC151537
0.844	Intermediate Similarity	NPC165770
0.844	Intermediate Similarity	NPC476632
0.844	Intermediate Similarity	NPC225679
0.8431	Intermediate Similarity	NPC259512
0.8431	Intermediate Similarity	NPC312132
0.8426	Intermediate Similarity	NPC299568
0.8426	Intermediate Similarity	NPC186385
0.8421	Intermediate Similarity	NPC474131
0.8411	Intermediate Similarity	NPC66834
0.8411	Intermediate Similarity	NPC151477
0.8396	Intermediate Similarity	NPC219286
0.8396	Intermediate Similarity	NPC138942
0.8396	Intermediate Similarity	NPC99557
0.8365	Intermediate Similarity	NPC225506
0.8365	Intermediate Similarity	NPC10588
0.8365	Intermediate Similarity	NPC166761
0.8365	Intermediate Similarity	NPC174911
0.8364	Intermediate Similarity	NPC98372
0.8364	Intermediate Similarity	NPC43525
0.835	Intermediate Similarity	NPC474073
0.8349	Intermediate Similarity	NPC296683
0.8333	Intermediate Similarity	NPC32152
0.8333	Intermediate Similarity	NPC8392
0.8333	Intermediate Similarity	NPC306295
0.8333	Intermediate Similarity	NPC32714
0.8319	Intermediate Similarity	NPC320864
0.8318	Intermediate Similarity	NPC21594
0.8304	Intermediate Similarity	NPC473718
0.8302	Intermediate Similarity	NPC288411
0.8288	Intermediate Similarity	NPC117846
0.8288	Intermediate Similarity	NPC23804
0.8283	Intermediate Similarity	NPC27974
0.8276	Intermediate Similarity	NPC168707
0.8276	Intermediate Similarity	NPC48623
0.8273	Intermediate Similarity	NPC224527
0.8269	Intermediate Similarity	NPC252821
0.8269	Intermediate Similarity	NPC299762
0.8269	Intermediate Similarity	NPC33675
0.8269	Intermediate Similarity	NPC128723
0.8269	Intermediate Similarity	NPC122005
0.8261	Intermediate Similarity	NPC232295
0.8257	Intermediate Similarity	NPC98392
0.8257	Intermediate Similarity	NPC19808
0.8257	Intermediate Similarity	NPC33728
0.8246	Intermediate Similarity	NPC206
0.8241	Intermediate Similarity	NPC61033
0.8241	Intermediate Similarity	NPC233320
0.8241	Intermediate Similarity	NPC305603
0.8235	Intermediate Similarity	NPC76938
0.8235	Intermediate Similarity	NPC289769
0.8235	Intermediate Similarity	NPC245187
0.8235	Intermediate Similarity	NPC152415
0.823	Intermediate Similarity	NPC471668
0.8224	Intermediate Similarity	NPC134829
0.8224	Intermediate Similarity	NPC246056
0.8218	Intermediate Similarity	NPC231150
0.8218	Intermediate Similarity	NPC204210
0.8214	Intermediate Similarity	NPC107240
0.8208	Intermediate Similarity	NPC168829
0.8208	Intermediate Similarity	NPC233827
0.82	Intermediate Similarity	NPC70436
0.8198	Intermediate Similarity	NPC228425
0.8198	Intermediate Similarity	NPC166995
0.8198	Intermediate Similarity	NPC228452
0.819	Intermediate Similarity	NPC211885
0.819	Intermediate Similarity	NPC474175
0.819	Intermediate Similarity	NPC45663
0.8182	Intermediate Similarity	NPC13482
0.8182	Intermediate Similarity	NPC407
0.8182	Intermediate Similarity	NPC471535
0.8182	Intermediate Similarity	NPC224870
0.8182	Intermediate Similarity	NPC307235
0.8174	Intermediate Similarity	NPC469644
0.8174	Intermediate Similarity	NPC323074
0.8174	Intermediate Similarity	NPC151197
0.8173	Intermediate Similarity	NPC88420
0.8165	Intermediate Similarity	NPC63698
0.8165	Intermediate Similarity	NPC174981
0.8165	Intermediate Similarity	NPC61885
0.8158	Intermediate Similarity	NPC304510
0.8158	Intermediate Similarity	NPC172219
0.8155	Intermediate Similarity	NPC144682
0.8148	Intermediate Similarity	NPC39664
0.8148	Intermediate Similarity	NPC470700
0.8148	Intermediate Similarity	NPC39097
0.8148	Intermediate Similarity	NPC118286
0.8148	Intermediate Similarity	NPC310456
0.8148	Intermediate Similarity	NPC109691
0.8148	Intermediate Similarity	NPC302681
0.8148	Intermediate Similarity	NPC271274
0.8142	Intermediate Similarity	NPC84999
0.8142	Intermediate Similarity	NPC474486
0.8142	Intermediate Similarity	NPC232165
0.8142	Intermediate Similarity	NPC246760
0.8137	Intermediate Similarity	NPC55903

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 NPC469913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	1013
0.2-0.3	1620
0.3-0.4	3021
0.4-0.5	1763
0.5-0.6	1089
0.6-0.7	317
0.7-0.8	45
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8725	High Similarity	NPD289	Clinical (unspecified phase)
0.8704	High Similarity	NPD7635	Approved
0.8515	High Similarity	NPD844	Approved
0.85	High Similarity	NPD845	Approved
0.8431	Intermediate Similarity	NPD288	Approved
0.8426	Intermediate Similarity	NPD4750	Phase 3
0.8304	Intermediate Similarity	NPD6671	Approved
0.8155	Intermediate Similarity	NPD1809	Phase 2
0.8113	Intermediate Similarity	NPD846	Approved
0.8113	Intermediate Similarity	NPD940	Approved
0.8095	Intermediate Similarity	NPD3020	Approved
0.8067	Intermediate Similarity	NPD6696	Suspended
0.7981	Intermediate Similarity	NPD2860	Approved
0.7981	Intermediate Similarity	NPD2859	Approved
0.7885	Intermediate Similarity	NPD2933	Approved
0.7885	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD2934	Approved
0.7768	Intermediate Similarity	NPD3021	Approved
0.7768	Intermediate Similarity	NPD3022	Approved
0.7759	Intermediate Similarity	NPD7340	Approved
0.7748	Intermediate Similarity	NPD2342	Discontinued
0.7658	Intermediate Similarity	NPD1445	Approved
0.7658	Intermediate Similarity	NPD1444	Approved
0.7632	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD9500	Approved
0.7541	Intermediate Similarity	NPD4749	Approved
0.7525	Intermediate Similarity	NPD111	Approved
0.7523	Intermediate Similarity	NPD1242	Phase 1
0.75	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1398	Phase 1
0.7456	Intermediate Similarity	NPD1792	Phase 2
0.744	Intermediate Similarity	NPD2861	Phase 2
0.7436	Intermediate Similarity	NPD497	Approved
0.7402	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4059	Approved
0.735	Intermediate Similarity	NPD496	Approved
0.735	Intermediate Similarity	NPD2228	Approved
0.735	Intermediate Similarity	NPD498	Approved
0.735	Intermediate Similarity	NPD2234	Approved
0.735	Intermediate Similarity	NPD495	Approved
0.735	Intermediate Similarity	NPD2229	Approved
0.7333	Intermediate Similarity	NPD3091	Approved
0.7323	Intermediate Similarity	NPD4625	Phase 3
0.7311	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD3092	Approved
0.7213	Intermediate Similarity	NPD4626	Approved
0.7213	Intermediate Similarity	NPD3019	Approved
0.7213	Intermediate Similarity	NPD2932	Approved
0.719	Intermediate Similarity	NPD5304	Approved
0.719	Intermediate Similarity	NPD5303	Approved
0.719	Intermediate Similarity	NPD7330	Discontinued
0.7177	Intermediate Similarity	NPD2233	Approved
0.7177	Intermediate Similarity	NPD2230	Approved
0.7177	Intermediate Similarity	NPD2232	Approved
0.7172	Intermediate Similarity	NPD9088	Approved
0.7154	Intermediate Similarity	NPD3496	Discontinued
0.7143	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3094	Phase 2
0.7131	Intermediate Similarity	NPD4093	Discontinued
0.7097	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1201	Approved
0.7073	Intermediate Similarity	NPD4589	Approved
0.7049	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD968	Approved
0.7034	Intermediate Similarity	NPD228	Approved
0.7027	Intermediate Similarity	NPD9273	Approved
0.7025	Intermediate Similarity	NPD7636	Approved
0.7008	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1791	Approved
0.7	Intermediate Similarity	NPD9618	Approved
0.7	Intermediate Similarity	NPD9614	Approved
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1793	Approved
0.6992	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7644	Approved
0.6949	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1751	Approved
0.6935	Remote Similarity	NPD3095	Discontinued
0.6935	Remote Similarity	NPD2286	Discontinued
0.6935	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3028	Approved
0.6899	Remote Similarity	NPD5736	Approved
0.6894	Remote Similarity	NPD4060	Phase 1
0.6894	Remote Similarity	NPD2238	Phase 2
0.6889	Remote Similarity	NPD2935	Discontinued
0.6889	Remote Similarity	NPD6100	Approved
0.6889	Remote Similarity	NPD6099	Approved
0.688	Remote Similarity	NPD3143	Discontinued
0.6875	Remote Similarity	NPD1131	Approved
0.6875	Remote Similarity	NPD1133	Approved
0.6875	Remote Similarity	NPD1135	Approved
0.6875	Remote Similarity	NPD1470	Approved
0.6875	Remote Similarity	NPD1129	Approved
0.6875	Remote Similarity	NPD1134	Approved
0.687	Remote Similarity	NPD9610	Approved
0.687	Remote Similarity	NPD9608	Approved
0.6864	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5691	Approved
0.6846	Remote Similarity	NPD4908	Phase 1
0.6833	Remote Similarity	NPD1138	Approved
0.6833	Remote Similarity	NPD9377	Approved
0.6833	Remote Similarity	NPD9379	Approved
0.6829	Remote Similarity	NPD9616	Approved
0.6829	Remote Similarity	NPD9613	Approved
0.6829	Remote Similarity	NPD9615	Approved
0.6825	Remote Similarity	NPD1610	Phase 2
0.6825	Remote Similarity	NPD1611	Approved
0.6818	Remote Similarity	NPD6405	Approved
0.6818	Remote Similarity	NPD6407	Approved
0.6812	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6387	Discontinued
0.68	Remote Similarity	NPD9384	Approved
0.68	Remote Similarity	NPD9381	Approved
0.6796	Remote Similarity	NPD9093	Approved
0.6794	Remote Similarity	NPD3027	Phase 3
0.6783	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2684	Approved
0.6777	Remote Similarity	NPD5283	Phase 1
0.6774	Remote Similarity	NPD316	Approved
0.6772	Remote Similarity	NPD3070	Discontinued
0.6769	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD9087	Approved
0.6759	Remote Similarity	NPD9295	Approved
0.675	Remote Similarity	NPD1137	Approved
0.675	Remote Similarity	NPD1139	Approved
0.6748	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD9089	Approved
0.6719	Remote Similarity	NPD9622	Approved
0.6719	Remote Similarity	NPD4659	Approved
0.6718	Remote Similarity	NPD596	Approved
0.6718	Remote Similarity	NPD600	Approved
0.6718	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4818	Approved
0.6696	Remote Similarity	NPD4817	Approved
0.6695	Remote Similarity	NPD290	Approved
0.6694	Remote Similarity	NPD856	Approved
0.6694	Remote Similarity	NPD16	Approved
0.6694	Remote Similarity	NPD7843	Approved
0.6692	Remote Similarity	NPD2194	Approved
0.6692	Remote Similarity	NPD858	Approved
0.6692	Remote Similarity	NPD4624	Approved
0.6692	Remote Similarity	NPD602	Approved
0.6692	Remote Similarity	NPD599	Approved
0.6692	Remote Similarity	NPD2195	Approved
0.6692	Remote Similarity	NPD6663	Approved
0.6692	Remote Similarity	NPD859	Approved
0.669	Remote Similarity	NPD6090	Discontinued
0.6667	Remote Similarity	NPD4097	Suspended
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD709	Approved
0.6667	Remote Similarity	NPD2668	Approved
0.6667	Remote Similarity	NPD7157	Approved
0.6667	Remote Similarity	NPD2667	Approved
0.6667	Remote Similarity	NPD8651	Approved
0.6641	Remote Similarity	NPD2231	Phase 2
0.6641	Remote Similarity	NPD2235	Phase 2
0.6641	Remote Similarity	NPD3636	Approved
0.6641	Remote Similarity	NPD3637	Approved
0.6641	Remote Similarity	NPD1608	Approved
0.6641	Remote Similarity	NPD3635	Approved
0.6641	Remote Similarity	NPD2237	Approved
0.664	Remote Similarity	NPD1548	Phase 1
0.664	Remote Similarity	NPD7741	Discontinued
0.6615	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD4103	Phase 2
0.6614	Remote Similarity	NPD1980	Approved
0.6614	Remote Similarity	NPD3026	Approved
0.6614	Remote Similarity	NPD1983	Approved
0.6614	Remote Similarity	NPD1981	Approved
0.6614	Remote Similarity	NPD3023	Approved
0.6596	Remote Similarity	NPD3300	Phase 2
0.6594	Remote Similarity	NPD4725	Approved
0.6594	Remote Similarity	NPD5763	Approved
0.6594	Remote Similarity	NPD4721	Approved
0.6594	Remote Similarity	NPD4726	Approved
0.6594	Remote Similarity	NPD5762	Approved
0.6591	Remote Similarity	NPD2606	Approved
0.6591	Remote Similarity	NPD2605	Approved
0.6589	Remote Similarity	NPD1755	Approved
0.6587	Remote Similarity	NPD3025	Approved
0.6587	Remote Similarity	NPD3024	Approved
0.6585	Remote Similarity	NPD475	Phase 2
0.6569	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD9294	Approved
0.6567	Remote Similarity	NPD840	Approved
0.6567	Remote Similarity	NPD839	Approved
0.6565	Remote Similarity	NPD3690	Phase 2
0.6565	Remote Similarity	NPD9621	Approved
0.6565	Remote Similarity	NPD9619	Approved
0.6565	Remote Similarity	NPD3691	Phase 2
0.6565	Remote Similarity	NPD9620	Approved
0.6565	Remote Similarity	NPD6584	Phase 3
0.6562	Remote Similarity	NPD422	Phase 1
0.656	Remote Similarity	NPD318	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