NPASS Compound

Structure

NPC469912 OpenBabel07101719522D 31 31 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 -1.7321 2.0000 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 -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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 6 24 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 25 1 0 0 0 0 17 28 1 0 0 0 0 18 28 1 0 0 0 0 19 23 1 0 0 0 0 19 26 2 0 0 0 0 21 3 1 6 0 0 0 22 4 1 6 0 0 0 23 27 2 0 0 0 0 24 25 2 0 0 0 0 24 26 1 0 0 0 0 25 27 1 0 0 0 0 26 29 1 0 0 0 0 27 30 1 0 0 0 0 28 7 1 6 0 0 0 28 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.38
Volume:	502.749
LogP:	8.326
LogD:	6.242
LogS:	-5.069
# 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:	0.246
Synthetic Accessibility Score:	3.826
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.887
MDCK Permeability:	1.3213516467658337e-05
Pgp-inhibitor:	0.146
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.734
Plasma Protein Binding (PPB):	100.35292053222656%
Volume Distribution (VD):	4.172
Pgp-substrate:	2.0869882106781006%

ADMET: Metabolism

CYP1A2-inhibitor:	0.122
CYP1A2-substrate:	0.248
CYP2C19-inhibitor:	0.477
CYP2C19-substrate:	0.681
CYP2C9-inhibitor:	0.163
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.449
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.235
CYP3A4-substrate:	0.104

ADMET: Excretion

Clearance (CL):	7.4
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.031
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.294
Skin Sensitization:	0.955
Carcinogencity:	0.021
Eye Corrosion:	0.236
Eye Irritation:	0.93
Respiratory Toxicity:	0.208

Download Data

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

Natural Product: NPC469912

Natural Product ID:	NPC469912
*Common Name:**	Beta-Tocopherylhydroquinone
IUPAC Name:	3-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-2,5-dimethylbenzene-1,4-diol
Synonyms:	Beta-Tocopherylhydroquinone
Standard InCHIKey:	BDNUOZAHAFRPOR-DQCZWYHMSA-N
Standard InCHI:	InChI=1S/C28H50O3/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7,31)18-16-25-24(6)26(29)19-23(5)27(25)30/h19-22,29-31H,8-18H2,1-7H3/t21-,22-,28-/m1/s1
SMILES:	CC1=CC(=C(C(=C1O)CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1258083
PubChem CID:	49765074
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	2

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	190000.0	nM	PMID[506759]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	500000.0	nM	PMID[506759]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	500000.0	nM	PMID[506759]

☑ 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 NPC469912 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	324
0.1-0.2	1610
0.2-0.3	3940
0.3-0.4	13252
0.4-0.5	7483
0.5-0.6	10228
0.6-0.7	4555
0.7-0.8	1043
0.8-0.85	200
0.85-0.9	53
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9515	High Similarity	NPC469913
0.932	High Similarity	NPC272029
0.9126	High Similarity	NPC477685
0.9048	High Similarity	NPC117115
0.9038	High Similarity	NPC108497
0.9009	High Similarity	NPC141001
0.9	High Similarity	NPC471534
0.8991	High Similarity	NPC302371
0.8981	High Similarity	NPC132720
0.8962	High Similarity	NPC53740
0.8942	High Similarity	NPC80800
0.8909	High Similarity	NPC263753
0.8899	High Similarity	NPC151537
0.8899	High Similarity	NPC54373
0.8879	High Similarity	NPC151477
0.8868	High Similarity	NPC47284
0.8857	High Similarity	NPC269212
0.8846	High Similarity	NPC72729
0.8846	High Similarity	NPC48730
0.8846	High Similarity	NPC129373
0.8846	High Similarity	NPC248396
0.8818	High Similarity	NPC62867
0.8818	High Similarity	NPC177962
0.8785	High Similarity	NPC21594
0.8774	High Similarity	NPC475580
0.875	High Similarity	NPC260775
0.8727	High Similarity	NPC266937
0.8727	High Similarity	NPC77772
0.8727	High Similarity	NPC470770
0.8707	High Similarity	NPC48623
0.8707	High Similarity	NPC168707
0.8704	High Similarity	NPC320439
0.8673	High Similarity	NPC471668
0.8667	High Similarity	NPC130756
0.8667	High Similarity	NPC12931
0.8667	High Similarity	NPC70677
0.8654	High Similarity	NPC79241
0.8654	High Similarity	NPC6597
0.8654	High Similarity	NPC152097
0.8654	High Similarity	NPC475078
0.8636	High Similarity	NPC224870
0.8621	High Similarity	NPC45663
0.8611	High Similarity	NPC201662
0.8611	High Similarity	NPC155072
0.8611	High Similarity	NPC99836
0.8611	High Similarity	NPC12640
0.8609	High Similarity	NPC469644
0.8609	High Similarity	NPC151197
0.8598	High Similarity	NPC475225
0.8596	High Similarity	NPC172219
0.8596	High Similarity	NPC304510
0.8585	High Similarity	NPC252105
0.8559	High Similarity	NPC260323
0.8559	High Similarity	NPC176279
0.8558	High Similarity	NPC312132
0.8558	High Similarity	NPC259512
0.8545	High Similarity	NPC282855
0.8545	High Similarity	NPC58865
0.8545	High Similarity	NPC186385
0.8545	High Similarity	NPC299568
0.8545	High Similarity	NPC26013
0.8532	High Similarity	NPC66834
0.8532	High Similarity	NPC474352
0.8532	High Similarity	NPC232523
0.8532	High Similarity	NPC204901
0.8532	High Similarity	NPC158253
0.8522	High Similarity	NPC154030
0.8522	High Similarity	NPC471671
0.8522	High Similarity	NPC206
0.8519	High Similarity	NPC37802
0.8505	High Similarity	NPC471228
0.8505	High Similarity	NPC235762
0.8482	Intermediate Similarity	NPC46940
0.8482	Intermediate Similarity	NPC250323
0.8468	Intermediate Similarity	NPC208229
0.8455	Intermediate Similarity	NPC279887
0.8455	Intermediate Similarity	NPC68260
0.8455	Intermediate Similarity	NPC95344
0.8455	Intermediate Similarity	NPC306295
0.8448	Intermediate Similarity	NPC93071
0.8448	Intermediate Similarity	NPC126002
0.8435	Intermediate Similarity	NPC320864
0.8426	Intermediate Similarity	NPC244513
0.8426	Intermediate Similarity	NPC238696
0.8426	Intermediate Similarity	NPC218879
0.8426	Intermediate Similarity	NPC227458
0.8421	Intermediate Similarity	NPC35797
0.8421	Intermediate Similarity	NPC192948
0.8421	Intermediate Similarity	NPC246760
0.8421	Intermediate Similarity	NPC469719
0.8421	Intermediate Similarity	NPC84999
0.8411	Intermediate Similarity	NPC12221
0.8407	Intermediate Similarity	NPC715
0.8407	Intermediate Similarity	NPC23804
0.8396	Intermediate Similarity	NPC299762
0.8396	Intermediate Similarity	NPC33675
0.8393	Intermediate Similarity	NPC95716
0.8393	Intermediate Similarity	NPC224527
0.8378	Intermediate Similarity	NPC473524
0.8365	Intermediate Similarity	NPC245187
0.8362	Intermediate Similarity	NPC469609
0.8362	Intermediate Similarity	NPC139047
0.8348	Intermediate Similarity	NPC38893
0.8348	Intermediate Similarity	NPC115808
0.8348	Intermediate Similarity	NPC477137
0.8348	Intermediate Similarity	NPC308311
0.8348	Intermediate Similarity	NPC92
0.8348	Intermediate Similarity	NPC469663
0.8333	Intermediate Similarity	NPC249270
0.8333	Intermediate Similarity	NPC195922
0.8333	Intermediate Similarity	NPC233827
0.8333	Intermediate Similarity	NPC107240
0.8319	Intermediate Similarity	NPC228452
0.8319	Intermediate Similarity	NPC71094
0.8319	Intermediate Similarity	NPC471179
0.8318	Intermediate Similarity	NPC174911
0.8318	Intermediate Similarity	NPC130103
0.8318	Intermediate Similarity	NPC211885
0.8305	Intermediate Similarity	NPC129176
0.8304	Intermediate Similarity	NPC296683
0.8304	Intermediate Similarity	NPC141782
0.8304	Intermediate Similarity	NPC13482
0.8302	Intermediate Similarity	NPC77492
0.8291	Intermediate Similarity	NPC476020
0.8288	Intermediate Similarity	NPC11554
0.8286	Intermediate Similarity	NPC222146
0.8276	Intermediate Similarity	NPC470760
0.8276	Intermediate Similarity	NPC187993
0.8276	Intermediate Similarity	NPC477136
0.8276	Intermediate Similarity	NPC238176
0.8273	Intermediate Similarity	NPC310456
0.8273	Intermediate Similarity	NPC54765
0.8269	Intermediate Similarity	NPC147284
0.8269	Intermediate Similarity	NPC210497
0.8269	Intermediate Similarity	NPC29373
0.8269	Intermediate Similarity	NPC306884
0.8269	Intermediate Similarity	NPC3358
0.8269	Intermediate Similarity	NPC94139
0.8269	Intermediate Similarity	NPC162314
0.8261	Intermediate Similarity	NPC474486
0.8246	Intermediate Similarity	NPC117846
0.8246	Intermediate Similarity	NPC28784
0.8246	Intermediate Similarity	NPC296144
0.8246	Intermediate Similarity	NPC319803
0.8241	Intermediate Similarity	NPC166313
0.8241	Intermediate Similarity	NPC294186
0.8241	Intermediate Similarity	NPC137415
0.8241	Intermediate Similarity	NPC11280
0.8241	Intermediate Similarity	NPC147310
0.8241	Intermediate Similarity	NPC192032
0.8241	Intermediate Similarity	NPC24407
0.822	Intermediate Similarity	NPC318581
0.822	Intermediate Similarity	NPC325544
0.822	Intermediate Similarity	NPC477037
0.8214	Intermediate Similarity	NPC19808
0.8214	Intermediate Similarity	NPC33728
0.8205	Intermediate Similarity	NPC9592
0.8205	Intermediate Similarity	NPC48781
0.819	Intermediate Similarity	NPC126759
0.819	Intermediate Similarity	NPC219112
0.819	Intermediate Similarity	NPC308828
0.819	Intermediate Similarity	NPC242580
0.819	Intermediate Similarity	NPC236070
0.819	Intermediate Similarity	NPC69539
0.8182	Intermediate Similarity	NPC219286
0.8182	Intermediate Similarity	NPC471350
0.8182	Intermediate Similarity	NPC61685
0.8182	Intermediate Similarity	NPC138942
0.8182	Intermediate Similarity	NPC99557
0.8174	Intermediate Similarity	NPC268160
0.8174	Intermediate Similarity	NPC474114
0.8174	Intermediate Similarity	NPC474050
0.8174	Intermediate Similarity	NPC114918
0.8174	Intermediate Similarity	NPC473931
0.8173	Intermediate Similarity	NPC231150
0.8165	Intermediate Similarity	NPC222522
0.8165	Intermediate Similarity	NPC71002
0.8165	Intermediate Similarity	NPC313030
0.8165	Intermediate Similarity	NPC24404
0.8165	Intermediate Similarity	NPC53051
0.8165	Intermediate Similarity	NPC85479
0.8165	Intermediate Similarity	NPC146798
0.8165	Intermediate Similarity	NPC302219
0.8165	Intermediate Similarity	NPC106396
0.8165	Intermediate Similarity	NPC94351
0.8165	Intermediate Similarity	NPC249828
0.8165	Intermediate Similarity	NPC242342
0.8165	Intermediate Similarity	NPC168303
0.8158	Intermediate Similarity	NPC98372
0.8158	Intermediate Similarity	NPC166995
0.8158	Intermediate Similarity	NPC473521
0.8158	Intermediate Similarity	NPC228425
0.8148	Intermediate Similarity	NPC225506
0.8136	Intermediate Similarity	NPC323074
0.8125	Intermediate Similarity	NPC174981
0.8125	Intermediate Similarity	NPC64586
0.812	Intermediate Similarity	NPC299180
0.8115	Intermediate Similarity	NPC470726
0.8115	Intermediate Similarity	NPC124030
0.8113	Intermediate Similarity	NPC8392

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 NPC469912 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	1005
0.2-0.3	1603
0.3-0.4	3051
0.4-0.5	1779
0.5-0.6	1059
0.6-0.7	286
0.7-0.8	50
0.8-0.85	5
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD7635	Approved
0.8558	High Similarity	NPD288	Approved
0.8545	High Similarity	NPD4750	Phase 3
0.8491	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD6696	Suspended
0.8462	Intermediate Similarity	NPD844	Approved
0.8269	Intermediate Similarity	NPD845	Approved
0.8198	Intermediate Similarity	NPD2342	Discontinued
0.819	Intermediate Similarity	NPD7340	Approved
0.7949	Intermediate Similarity	NPD6671	Approved
0.7944	Intermediate Similarity	NPD1809	Phase 2
0.7931	Intermediate Similarity	NPD1398	Phase 1
0.789	Intermediate Similarity	NPD3020	Approved
0.7863	Intermediate Similarity	NPD497	Approved
0.7778	Intermediate Similarity	NPD498	Approved
0.7778	Intermediate Similarity	NPD495	Approved
0.7778	Intermediate Similarity	NPD496	Approved
0.7748	Intermediate Similarity	NPD940	Approved
0.7748	Intermediate Similarity	NPD846	Approved
0.7731	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD4625	Phase 3
0.7685	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4749	Approved
0.7623	Intermediate Similarity	NPD4626	Approved
0.7623	Intermediate Similarity	NPD4059	Approved
0.7619	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD2859	Approved
0.7615	Intermediate Similarity	NPD2860	Approved
0.7603	Intermediate Similarity	NPD3091	Approved
0.7586	Intermediate Similarity	NPD3022	Approved
0.7586	Intermediate Similarity	NPD3021	Approved
0.7523	Intermediate Similarity	NPD2933	Approved
0.7523	Intermediate Similarity	NPD2934	Approved
0.752	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3092	Approved
0.748	Intermediate Similarity	NPD2932	Approved
0.748	Intermediate Similarity	NPD3019	Approved
0.7478	Intermediate Similarity	NPD1444	Approved
0.7478	Intermediate Similarity	NPD1445	Approved
0.7458	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1792	Phase 2
0.7402	Intermediate Similarity	NPD3094	Phase 2
0.7377	Intermediate Similarity	NPD7644	Approved
0.736	Intermediate Similarity	NPD1201	Approved
0.7339	Intermediate Similarity	NPD2286	Discontinued
0.7333	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD2861	Phase 2
0.7258	Intermediate Similarity	NPD4093	Discontinued
0.7258	Intermediate Similarity	NPD5691	Approved
0.7222	Intermediate Similarity	NPD1611	Approved
0.7217	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD9500	Approved
0.72	Intermediate Similarity	NPD3095	Discontinued
0.72	Intermediate Similarity	NPD1751	Approved
0.7193	Intermediate Similarity	NPD1242	Phase 1
0.719	Intermediate Similarity	NPD2229	Approved
0.719	Intermediate Similarity	NPD2228	Approved
0.719	Intermediate Similarity	NPD2234	Approved
0.7177	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD111	Approved
0.7165	Intermediate Similarity	NPD2233	Approved
0.7165	Intermediate Similarity	NPD2232	Approved
0.7165	Intermediate Similarity	NPD2230	Approved
0.7154	Intermediate Similarity	NPD5736	Approved
0.7132	Intermediate Similarity	NPD1470	Approved
0.7132	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6099	Approved
0.7132	Intermediate Similarity	NPD6100	Approved
0.7042	Intermediate Similarity	NPD6090	Discontinued
0.704	Intermediate Similarity	NPD5303	Approved
0.704	Intermediate Similarity	NPD5304	Approved
0.704	Intermediate Similarity	NPD7330	Discontinued
0.7037	Intermediate Similarity	NPD4097	Suspended
0.7015	Intermediate Similarity	NPD4060	Phase 1
0.6992	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD2194	Approved
0.6947	Remote Similarity	NPD2195	Approved
0.6947	Remote Similarity	NPD4624	Approved
0.694	Remote Similarity	NPD6663	Approved
0.6934	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4589	Approved
0.6929	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1283	Approved
0.6901	Remote Similarity	NPD7390	Discontinued
0.6894	Remote Similarity	NPD3637	Approved
0.6894	Remote Similarity	NPD3635	Approved
0.6894	Remote Similarity	NPD3636	Approved
0.6889	Remote Similarity	NPD2238	Phase 2
0.6884	Remote Similarity	NPD5405	Approved
0.6884	Remote Similarity	NPD5408	Approved
0.6884	Remote Similarity	NPD5404	Approved
0.6884	Remote Similarity	NPD5406	Approved
0.688	Remote Similarity	NPD405	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7636	Approved
0.6875	Remote Similarity	NPD3026	Approved
0.6875	Remote Similarity	NPD3496	Discontinued
0.6875	Remote Similarity	NPD3023	Approved
0.6866	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7985	Registered
0.6861	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1793	Approved
0.6855	Remote Similarity	NPD1791	Approved
0.6853	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1651	Approved
0.685	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3024	Approved
0.685	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3025	Approved
0.6842	Remote Similarity	NPD2606	Approved
0.6842	Remote Similarity	NPD2605	Approved
0.6835	Remote Similarity	NPD5762	Approved
0.6835	Remote Similarity	NPD5763	Approved
0.6835	Remote Similarity	NPD4725	Approved
0.6835	Remote Similarity	NPD4721	Approved
0.6835	Remote Similarity	NPD4726	Approved
0.6831	Remote Similarity	NPD3300	Phase 2
0.6827	Remote Similarity	NPD9088	Approved
0.6812	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.68	Remote Similarity	NPD709	Approved
0.6791	Remote Similarity	NPD5155	Approved
0.6791	Remote Similarity	NPD5156	Approved
0.6786	Remote Similarity	NPD4256	Phase 2
0.6786	Remote Similarity	NPD4257	Approved
0.6774	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD2237	Approved
0.6765	Remote Similarity	NPD3620	Phase 2
0.6765	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.675	Remote Similarity	NPD968	Approved
0.6748	Remote Similarity	NPD228	Approved
0.6744	Remote Similarity	NPD3143	Discontinued
0.6741	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD9273	Approved
0.672	Remote Similarity	NPD9614	Approved
0.672	Remote Similarity	NPD9618	Approved
0.6718	Remote Similarity	NPD5327	Phase 3
0.6716	Remote Similarity	NPD3595	Approved
0.6716	Remote Similarity	NPD4908	Phase 1
0.6716	Remote Similarity	NPD3594	Approved
0.6715	Remote Similarity	NPD5735	Approved
0.6694	Remote Similarity	NPD1138	Approved
0.6692	Remote Similarity	NPD1281	Approved
0.6692	Remote Similarity	NPD1610	Phase 2
0.6691	Remote Similarity	NPD7743	Approved
0.6691	Remote Similarity	NPD7742	Approved
0.6667	Remote Similarity	NPD6387	Discontinued
0.6667	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2157	Approved
0.6667	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD6353	Approved
0.6643	Remote Similarity	NPD2935	Discontinued
0.6642	Remote Similarity	NPD1712	Approved
0.6641	Remote Similarity	NPD7741	Discontinued
0.6641	Remote Similarity	NPD3070	Discontinued
0.664	Remote Similarity	NPD5283	Phase 1
0.662	Remote Similarity	NPD6674	Discontinued
0.6617	Remote Similarity	NPD1131	Approved
0.6617	Remote Similarity	NPD1129	Approved
0.6617	Remote Similarity	NPD1133	Approved
0.6617	Remote Similarity	NPD1134	Approved
0.6617	Remote Similarity	NPD1135	Approved
0.6615	Remote Similarity	NPD1980	Approved
0.6615	Remote Similarity	NPD1983	Approved
0.6615	Remote Similarity	NPD1981	Approved
0.6615	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD1139	Approved
0.6613	Remote Similarity	NPD1137	Approved
0.661	Remote Similarity	NPD3028	Approved
0.66	Remote Similarity	NPD5929	Approved
0.6596	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1669	Approved
0.6585	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD9608	Approved
0.6583	Remote Similarity	NPD9610	Approved
0.6569	Remote Similarity	NPD6407	Approved
0.6569	Remote Similarity	NPD6405	Approved
0.6565	Remote Similarity	NPD3705	Approved
0.6562	Remote Similarity	NPD9613	Approved
0.6562	Remote Similarity	NPD9615	Approved
0.6562	Remote Similarity	NPD9616	Approved
0.656	Remote Similarity	NPD9377	Approved
0.656	Remote Similarity	NPD9379	Approved
0.6555	Remote Similarity	NPD4817	Approved
0.6555	Remote Similarity	NPD4818	Approved
0.6552	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7041	Phase 2
0.6544	Remote Similarity	NPD3027	Phase 3
0.6541	Remote Similarity	NPD8651	Approved
0.6538	Remote Similarity	NPD2668	Approved
0.6538	Remote Similarity	NPD5126	Approved
0.6538	Remote Similarity	NPD9384	Approved
0.6538	Remote Similarity	NPD2667	Approved
0.6538	Remote Similarity	NPD9381	Approved
0.6538	Remote Similarity	NPD5125	Phase 3
0.6535	Remote Similarity	NPD7157	Approved
0.6522	Remote Similarity	NPD4140	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