NPASS Compound

Structure

NPC137415 OpenBabel07101718322D 21 21 0 0 0 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 10.5000 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 3.4641 9.0000 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 2.5981 7.5000 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 6.0000 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 4.5000 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 -0.0000 3.0000 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 -1.7321 1.0000 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 -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 -0.0000 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 -0.5000 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 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 17 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.24
Volume:	338.295
LogP:	7.195
LogD:	4.542
LogS:	-3.585
# Rotatable Bonds:	12
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.467
Synthetic Accessibility Score:	2.013
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.96
MDCK Permeability:	1.354881351289805e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	98.44715118408203%
Volume Distribution (VD):	3.674
Pgp-substrate:	0.8681949377059937%

ADMET: Metabolism

CYP1A2-inhibitor:	0.854
CYP1A2-substrate:	0.199
CYP2C19-inhibitor:	0.849
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.296
CYP2C9-substrate:	0.985
CYP2D6-inhibitor:	0.943
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.625
CYP3A4-substrate:	0.065

ADMET: Excretion

Clearance (CL):	7.753
Half-life (T1/2):	0.636

ADMET: Toxicity

hERG Blockers:	0.227
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.513
Skin Sensitization:	0.962
Carcinogencity:	0.029
Eye Corrosion:	0.973
Eye Irritation:	0.955
Respiratory Toxicity:	0.791

Download Data

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

Natural Product: NPC137415

Natural Product ID:	NPC137415
*Common Name:**	5-Tridecyl Resorcinol
IUPAC Name:	5-tridecylbenzene-1,3-diol
Synonyms:	5-Tridecyl Resorcinol; 6-Tridecylresorcylic Acid
Standard InCHIKey:	UXOGOSLLGMYCNL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-14-18(20)16-19(21)15-17/h14-16,20-21H,2-13H2,1H3
SMILES:	CCCCCCCCCCCCCc1cc(O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451044
PubChem CID:	174862
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[27140807]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	leaves	n.a.	n.a.	PMID[33127538]
NPO22588	Lysimachia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6090589]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	fresh sarcotestas	Kwanak Campus of Seoul National University, Seoul, Korea	1996-Sep	PMID[9677265]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	leaves	St. Louis	1996-SEP	PMID[9834151]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834158]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Wood	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22588	Lysimachia japonica	Species	Primulaceae	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	10
Others	2

Activity Type	# Activity
Cell Line	5
Individual Protein	4
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT657	Individual Protein	1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase gamma-1	Bos taurus	IC50	=	72320.0	nM	PMID[470917]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1.91	ug.mL-1	PMID[470917]
NPT658	Cell Line	HT1197	Homo sapiens	IC50	=	2.2	ug.mL-1	PMID[470917]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	15.32	ug.mL-1	PMID[470917]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[470917]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[470917]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	2380.0	nM	PMID[470919]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	2740.0	nM	PMID[470919]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	<	50.0	%	PMID[470919]
NPT27	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[470917]
NPT2	Others	Unspecified		IC50	=	8000.0	nM	PMID[470918]
NPT2	Others	Unspecified		Ratio IC50	=	0.87	n.a.	PMID[470919]

☑ 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 NPC137415 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	241
0.1-0.2	1599
0.2-0.3	5070
0.3-0.4	14277
0.4-0.5	5239
0.5-0.6	8828
0.6-0.7	5673
0.7-0.8	1465
0.8-0.85	166
0.85-0.9	68
0.9-0.95	41
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC192032
1.0	High Similarity	NPC294186
1.0	High Similarity	NPC147310
1.0	High Similarity	NPC11280
1.0	High Similarity	NPC24407
1.0	High Similarity	NPC166313
0.9895	High Similarity	NPC106396
0.9895	High Similarity	NPC71002
0.9895	High Similarity	NPC168303
0.9895	High Similarity	NPC242342
0.9895	High Similarity	NPC222522
0.9895	High Similarity	NPC24404
0.9895	High Similarity	NPC94351
0.9895	High Similarity	NPC249828
0.9895	High Similarity	NPC146798
0.9895	High Similarity	NPC53051
0.9895	High Similarity	NPC302219
0.9895	High Similarity	NPC313030
0.9895	High Similarity	NPC85479
0.9789	High Similarity	NPC72947
0.9789	High Similarity	NPC284011
0.9684	High Similarity	NPC166761
0.9684	High Similarity	NPC10588
0.9592	High Similarity	NPC99836
0.9592	High Similarity	NPC12640
0.9592	High Similarity	NPC201662
0.9495	High Similarity	NPC232523
0.9495	High Similarity	NPC305603
0.9495	High Similarity	NPC61033
0.9495	High Similarity	NPC204901
0.9495	High Similarity	NPC158253
0.949	High Similarity	NPC37802
0.949	High Similarity	NPC134829
0.949	High Similarity	NPC246056
0.9394	High Similarity	NPC109691
0.9394	High Similarity	NPC39664
0.9394	High Similarity	NPC118286
0.9394	High Similarity	NPC470700
0.9394	High Similarity	NPC302681
0.9394	High Similarity	NPC39097
0.9388	High Similarity	NPC227458
0.9388	High Similarity	NPC241891
0.9388	High Similarity	NPC218879
0.9388	High Similarity	NPC244513
0.93	High Similarity	NPC54844
0.9255	High Similarity	NPC295295
0.9184	High Similarity	NPC100340
0.9184	High Similarity	NPC143659
0.9118	High Similarity	NPC299568
0.9118	High Similarity	NPC186385
0.9118	High Similarity	NPC19808
0.9118	High Similarity	NPC33728
0.9053	High Similarity	NPC3358
0.9053	High Similarity	NPC162314
0.9053	High Similarity	NPC147284
0.9053	High Similarity	NPC94139
0.9053	High Similarity	NPC210497
0.9053	High Similarity	NPC306884
0.9038	High Similarity	NPC166995
0.902	High Similarity	NPC174981
0.9	High Similarity	NPC102216
0.9	High Similarity	NPC30506
0.8952	High Similarity	NPC62546
0.8952	High Similarity	NPC263753
0.8952	High Similarity	NPC162113
0.8952	High Similarity	NPC23804
0.8942	High Similarity	NPC225679
0.8942	High Similarity	NPC4493
0.8942	High Similarity	NPC165770
0.8942	High Similarity	NPC224527
0.8942	High Similarity	NPC476632
0.89	High Similarity	NPC315022
0.8878	High Similarity	NPC291789
0.8857	High Similarity	NPC43525
0.8846	High Similarity	NPC168657
0.8842	High Similarity	NPC192
0.8812	High Similarity	NPC315936
0.8788	High Similarity	NPC80027
0.8774	High Similarity	NPC319803
0.8774	High Similarity	NPC117846
0.8725	High Similarity	NPC474839
0.8704	High Similarity	NPC114064
0.8704	High Similarity	NPC123559
0.87	High Similarity	NPC275053
0.87	High Similarity	NPC48730
0.87	High Similarity	NPC248573
0.87	High Similarity	NPC161571
0.87	High Similarity	NPC248396
0.87	High Similarity	NPC129373
0.8692	High Similarity	NPC107240
0.8679	High Similarity	NPC473521
0.8673	High Similarity	NPC32714
0.8667	High Similarity	NPC224870
0.8654	High Similarity	NPC61885
0.8654	High Similarity	NPC63698
0.8641	High Similarity	NPC469913
0.8632	High Similarity	NPC27974
0.8627	High Similarity	NPC119860
0.8624	High Similarity	NPC15860
0.8624	High Similarity	NPC127894
0.8624	High Similarity	NPC219070
0.8624	High Similarity	NPC470759
0.8614	High Similarity	NPC477685
0.8611	High Similarity	NPC53906
0.8611	High Similarity	NPC246760
0.8611	High Similarity	NPC84999
0.86	High Similarity	NPC260775
0.8598	High Similarity	NPC261343
0.8571	High Similarity	NPC76938
0.8545	High Similarity	NPC206
0.8545	High Similarity	NPC9592
0.8545	High Similarity	NPC48781
0.8544	High Similarity	NPC292452
0.8532	High Similarity	NPC115808
0.8519	High Similarity	NPC276737
0.8519	High Similarity	NPC22610
0.8515	High Similarity	NPC130756
0.8515	High Similarity	NPC12931
0.8515	High Similarity	NPC70677
0.85	High Similarity	NPC152097
0.85	High Similarity	NPC474073
0.8491	Intermediate Similarity	NPC242178
0.8485	Intermediate Similarity	NPC222146
0.8469	Intermediate Similarity	NPC55903
0.8462	Intermediate Similarity	NPC248904
0.8462	Intermediate Similarity	NPC164576
0.8455	Intermediate Similarity	NPC33270
0.8455	Intermediate Similarity	NPC69261
0.8455	Intermediate Similarity	NPC470760
0.8455	Intermediate Similarity	NPC277588
0.8455	Intermediate Similarity	NPC474933
0.8454	Intermediate Similarity	NPC55561
0.844	Intermediate Similarity	NPC808
0.8438	Intermediate Similarity	NPC19680
0.8431	Intermediate Similarity	NPC252105
0.8411	Intermediate Similarity	NPC268032
0.8396	Intermediate Similarity	NPC202647
0.8378	Intermediate Similarity	NPC190514
0.8378	Intermediate Similarity	NPC144343
0.8365	Intermediate Similarity	NPC471350
0.8364	Intermediate Similarity	NPC141090
0.8364	Intermediate Similarity	NPC150624
0.8351	Intermediate Similarity	NPC242240
0.8351	Intermediate Similarity	NPC318325
0.8351	Intermediate Similarity	NPC280347
0.8351	Intermediate Similarity	NPC123273
0.8351	Intermediate Similarity	NPC177420
0.835	Intermediate Similarity	NPC196479
0.835	Intermediate Similarity	NPC108497
0.8333	Intermediate Similarity	NPC72729
0.8333	Intermediate Similarity	NPC294741
0.8319	Intermediate Similarity	NPC24125
0.8318	Intermediate Similarity	NPC475018
0.8317	Intermediate Similarity	NPC79241
0.8317	Intermediate Similarity	NPC6597
0.8317	Intermediate Similarity	NPC475078
0.8316	Intermediate Similarity	NPC150837
0.8304	Intermediate Similarity	NPC184302
0.8304	Intermediate Similarity	NPC191866
0.8304	Intermediate Similarity	NPC217174
0.83	Intermediate Similarity	NPC26244
0.83	Intermediate Similarity	NPC274678
0.8286	Intermediate Similarity	NPC155072
0.8273	Intermediate Similarity	NPC472893
0.8273	Intermediate Similarity	NPC167934
0.8252	Intermediate Similarity	NPC80800
0.8247	Intermediate Similarity	NPC113460
0.8247	Intermediate Similarity	NPC25493
0.8246	Intermediate Similarity	NPC39029
0.8246	Intermediate Similarity	NPC237667
0.8241	Intermediate Similarity	NPC469912
0.8235	Intermediate Similarity	NPC33675
0.8235	Intermediate Similarity	NPC299762
0.823	Intermediate Similarity	NPC223451
0.8218	Intermediate Similarity	NPC312132
0.8218	Intermediate Similarity	NPC259512
0.8218	Intermediate Similarity	NPC473388
0.8208	Intermediate Similarity	NPC66834
0.8208	Intermediate Similarity	NPC176527
0.82	Intermediate Similarity	NPC245187
0.82	Intermediate Similarity	NPC27323
0.82	Intermediate Similarity	NPC152415
0.82	Intermediate Similarity	NPC316301
0.82	Intermediate Similarity	NPC151715
0.819	Intermediate Similarity	NPC47284
0.8182	Intermediate Similarity	NPC304541
0.8182	Intermediate Similarity	NPC231150
0.8182	Intermediate Similarity	NPC228287
0.8182	Intermediate Similarity	NPC180508
0.8174	Intermediate Similarity	NPC122175
0.8173	Intermediate Similarity	NPC471228
0.8173	Intermediate Similarity	NPC269212
0.8173	Intermediate Similarity	NPC235762
0.8173	Intermediate Similarity	NPC168393
0.8163	Intermediate Similarity	NPC258219
0.8158	Intermediate Similarity	NPC218753
0.8155	Intermediate Similarity	NPC211885
0.8155	Intermediate Similarity	NPC174911
0.8155	Intermediate Similarity	NPC130103
0.8148	Intermediate Similarity	NPC2682

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 NPC137415 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	1029
0.2-0.3	1616
0.3-0.4	2987
0.4-0.5	1793
0.5-0.6	1051
0.6-0.7	371
0.7-0.8	46
0.8-0.85	10
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9118	High Similarity	NPD4750	Phase 3
0.899	High Similarity	NPD940	Approved
0.899	High Similarity	NPD846	Approved
0.87	High Similarity	NPD1242	Phase 1
0.8485	Intermediate Similarity	NPD844	Approved
0.83	Intermediate Similarity	NPD2859	Approved
0.83	Intermediate Similarity	NPD2860	Approved
0.8235	Intermediate Similarity	NPD3020	Approved
0.8218	Intermediate Similarity	NPD288	Approved
0.82	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD2934	Approved
0.82	Intermediate Similarity	NPD2933	Approved
0.8155	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD9093	Approved
0.7949	Intermediate Similarity	NPD4749	Approved
0.7921	Intermediate Similarity	NPD845	Approved
0.7895	Intermediate Similarity	NPD9089	Approved
0.789	Intermediate Similarity	NPD3021	Approved
0.789	Intermediate Similarity	NPD3022	Approved
0.7835	Intermediate Similarity	NPD111	Approved
0.7778	Intermediate Similarity	NPD1444	Approved
0.7778	Intermediate Similarity	NPD1445	Approved
0.7767	Intermediate Similarity	NPD1809	Phase 2
0.775	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7635	Approved
0.7642	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6671	Approved
0.7568	Intermediate Similarity	NPD1792	Phase 2
0.7561	Intermediate Similarity	NPD4625	Phase 3
0.7561	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD9500	Approved
0.7459	Intermediate Similarity	NPD599	Approved
0.7459	Intermediate Similarity	NPD602	Approved
0.7459	Intermediate Similarity	NPD858	Approved
0.7459	Intermediate Similarity	NPD859	Approved
0.7426	Intermediate Similarity	NPD9094	Approved
0.7387	Intermediate Similarity	NPD2342	Discontinued
0.7339	Intermediate Similarity	NPD4908	Phase 1
0.7333	Intermediate Similarity	NPD1610	Phase 2
0.7304	Intermediate Similarity	NPD2228	Approved
0.7304	Intermediate Similarity	NPD2234	Approved
0.7304	Intermediate Similarity	NPD2229	Approved
0.729	Intermediate Similarity	NPD9273	Approved
0.7288	Intermediate Similarity	NPD1548	Phase 1
0.7288	Intermediate Similarity	NPD3091	Approved
0.7281	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD228	Approved
0.7258	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1791	Approved
0.7241	Intermediate Similarity	NPD1793	Approved
0.7231	Intermediate Similarity	NPD6099	Approved
0.7231	Intermediate Similarity	NPD6100	Approved
0.7222	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD422	Phase 1
0.719	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3092	Approved
0.7167	Intermediate Similarity	NPD3019	Approved
0.7167	Intermediate Similarity	NPD2932	Approved
0.7167	Intermediate Similarity	NPD4059	Approved
0.7156	Intermediate Similarity	NPD3028	Approved
0.7155	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6696	Suspended
0.7132	Intermediate Similarity	NPD2568	Approved
0.7117	Intermediate Similarity	NPD9610	Approved
0.7117	Intermediate Similarity	NPD9608	Approved
0.7105	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3094	Phase 2
0.7097	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD9618	Approved
0.7094	Intermediate Similarity	NPD9614	Approved
0.7083	Intermediate Similarity	NPD4093	Discontinued
0.7069	Intermediate Similarity	NPD9379	Approved
0.7069	Intermediate Similarity	NPD9377	Approved
0.7053	Intermediate Similarity	NPD9087	Approved
0.7043	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2684	Approved
0.7015	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9269	Phase 2
0.6977	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD943	Approved
0.6977	Remote Similarity	NPD1613	Approved
0.6949	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD9268	Approved
0.6939	Remote Similarity	NPD9088	Approved
0.6935	Remote Similarity	NPD2983	Phase 2
0.6935	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2982	Phase 2
0.6923	Remote Similarity	NPD7843	Approved
0.6917	Remote Similarity	NPD9616	Approved
0.6917	Remote Similarity	NPD9615	Approved
0.6917	Remote Similarity	NPD9613	Approved
0.6917	Remote Similarity	NPD16	Approved
0.6917	Remote Similarity	NPD856	Approved
0.6911	Remote Similarity	NPD1201	Approved
0.6894	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7157	Approved
0.6885	Remote Similarity	NPD2286	Discontinued
0.6885	Remote Similarity	NPD3095	Discontinued
0.6885	Remote Similarity	NPD9381	Approved
0.6885	Remote Similarity	NPD9384	Approved
0.6885	Remote Similarity	NPD1751	Approved
0.6885	Remote Similarity	NPD4626	Approved
0.6864	Remote Similarity	NPD5283	Phase 1
0.686	Remote Similarity	NPD7330	Discontinued
0.686	Remote Similarity	NPD316	Approved
0.6855	Remote Similarity	NPD2233	Approved
0.6855	Remote Similarity	NPD2981	Phase 2
0.6855	Remote Similarity	NPD2232	Approved
0.6855	Remote Similarity	NPD2230	Approved
0.685	Remote Similarity	NPD5736	Approved
0.685	Remote Similarity	NPD2861	Phase 2
0.685	Remote Similarity	NPD3018	Phase 2
0.6846	Remote Similarity	NPD2238	Phase 2
0.6842	Remote Similarity	NPD968	Approved
0.6837	Remote Similarity	NPD9294	Approved
0.6833	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD1129	Approved
0.6825	Remote Similarity	NPD1133	Approved
0.6825	Remote Similarity	NPD1131	Approved
0.6825	Remote Similarity	NPD1135	Approved
0.6825	Remote Similarity	NPD1134	Approved
0.6822	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.68	Remote Similarity	NPD9622	Approved
0.68	Remote Similarity	NPD4659	Approved
0.68	Remote Similarity	NPD1755	Approved
0.6794	Remote Similarity	NPD230	Phase 1
0.6783	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD290	Approved
0.6777	Remote Similarity	NPD318	Approved
0.6777	Remote Similarity	NPD317	Approved
0.6772	Remote Similarity	NPD6584	Phase 3
0.6769	Remote Similarity	NPD6405	Approved
0.6769	Remote Similarity	NPD6407	Approved
0.675	Remote Similarity	NPD255	Approved
0.675	Remote Similarity	NPD256	Approved
0.6748	Remote Similarity	NPD4589	Approved
0.6746	Remote Similarity	NPD5311	Approved
0.6746	Remote Similarity	NPD5310	Approved
0.6739	Remote Similarity	NPD7390	Discontinued
0.6724	Remote Similarity	NPD74	Approved
0.6724	Remote Similarity	NPD9266	Approved
0.6721	Remote Similarity	NPD1759	Phase 1
0.6721	Remote Similarity	NPD5304	Approved
0.6721	Remote Similarity	NPD5303	Approved
0.672	Remote Similarity	NPD1608	Approved
0.672	Remote Similarity	NPD2562	Approved
0.672	Remote Similarity	NPD2561	Approved
0.6718	Remote Similarity	NPD1240	Approved
0.6694	Remote Similarity	NPD9493	Approved
0.6694	Remote Similarity	NPD3496	Discontinued
0.6694	Remote Similarity	NPD7636	Approved
0.6694	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7340	Approved
0.6693	Remote Similarity	NPD1470	Approved
0.6693	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD4103	Phase 2
0.6693	Remote Similarity	NPD3053	Approved
0.6693	Remote Similarity	NPD3055	Approved
0.6692	Remote Similarity	NPD6111	Discontinued
0.6667	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD475	Phase 2
0.6667	Remote Similarity	NPD9244	Approved
0.6667	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD497	Approved
0.6667	Remote Similarity	NPD5451	Approved
0.6642	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2195	Approved
0.6641	Remote Similarity	NPD2194	Approved
0.6641	Remote Similarity	NPD9619	Approved
0.6641	Remote Similarity	NPD9621	Approved
0.6641	Remote Similarity	NPD6663	Approved
0.6641	Remote Similarity	NPD9620	Approved
0.6639	Remote Similarity	NPD1758	Phase 1
0.6639	Remote Similarity	NPD821	Approved
0.6638	Remote Similarity	NPD9263	Approved
0.6638	Remote Similarity	NPD9264	Approved
0.6638	Remote Similarity	NPD9267	Approved
0.6637	Remote Similarity	NPD4818	Approved
0.6637	Remote Similarity	NPD4817	Approved
0.6618	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD1607	Approved
0.6613	Remote Similarity	NPD1778	Approved
0.6613	Remote Similarity	NPD2667	Approved
0.6613	Remote Similarity	NPD2668	Approved
0.6612	Remote Similarity	NPD709	Approved
0.6591	Remote Similarity	NPD6346	Approved
0.6591	Remote Similarity	NPD1555	Discontinued
0.6589	Remote Similarity	NPD3636	Approved
0.6589	Remote Similarity	NPD3637	Approved
0.6589	Remote Similarity	NPD3635	Approved
0.6587	Remote Similarity	NPD2231	Phase 2
0.6587	Remote Similarity	NPD2235	Phase 2
0.6585	Remote Similarity	NPD9545	Approved
0.6585	Remote Similarity	NPD7741	Discontinued
0.6583	Remote Similarity	NPD495	Approved
0.6583	Remote Similarity	NPD1398	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