NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.21
Volume:	318.362
LogP:	6.014
LogD:	3.276
LogS:	-4.965
# Rotatable Bonds:	12
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.532
Synthetic Accessibility Score:	1.602
Fsp3:	0.611
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:	-5.043
MDCK Permeability:	2.4702680093469098e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.584
30% Bioavailability (F30%):	0.778

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	98.69032287597656%
Volume Distribution (VD):	0.664
Pgp-substrate:	0.36280661821365356%

ADMET: Metabolism

CYP1A2-inhibitor:	0.315
CYP1A2-substrate:	0.193
CYP2C19-inhibitor:	0.322
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.346
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.05

ADMET: Excretion

Clearance (CL):	2.307
Half-life (T1/2):	0.721

ADMET: Toxicity

hERG Blockers:	0.107
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.925
Carcinogencity:	0.067
Eye Corrosion:	0.525
Eye Irritation:	0.978
Respiratory Toxicity:	0.768

Download Data

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

Natural Product: NPC44830

Natural Product ID:	NPC44830
*Common Name:**	12-Phenyldodecanoic Acid
IUPAC Name:	12-phenyldodecanoic acid
Synonyms:
Standard InCHIKey:	IXEHFJJSVBVZHI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H28O2/c19-18(20)16-12-7-5-3-1-2-4-6-9-13-17-14-10-8-11-15-17/h8,10-11,14-15H,1-7,9,12-13,16H2,(H,19,20)
SMILES:	OC(=O)CCCCCCCCCCCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1567811
PubChem CID:	151922
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

*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
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	bark	Indonesia	n.a.	PMID[15270571]
NPO21076	Nephthea armata	Species	Nephtheidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15387641]
NPO22180	Dracaena mannii	Species	Asparagaceae	Eukaryota	n.a.	stem	n.a.	PMID[18481024]
NPO22180	Dracaena mannii	Species	Asparagaceae	Eukaryota	stems	Yaound, village of Bangoua, near Bangangt	2007-APR	PMID[20553003]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22313254]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20571	Limnodynastes interioris	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22180	Dracaena mannii	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22064	Mannia fragrans	Species	Aytoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18284	Cytisus ciliatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20708	Mesua beccariana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21076	Nephthea armata	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22867	Stephanitis rhododendri	Species	Tingidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22525	Lobophytum denticulatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22923	Parthenium bipinnatifidum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19330	Cephalaria procera	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22007	Acer spicatum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21819	Domohinea perrieri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22125	Helipterum propinquum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29112	Streptomyces luteosporeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17813	Pittosporum undulatum	Species	Pittosporaceae	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	2
Potency	14

Activity Type	# Activity
Individual Protein	13
Organism	2
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	15848.9	nM	PMID[515538]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	14125.4	nM	PMID[515538]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	15811.4	nM	PMID[515538]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	28183.8	nM	PMID[515538]
NPT2944	Individual Protein	Relaxin receptor 1	Homo sapiens	Potency	=	35481.3	nM	PMID[515538]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[515538]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	398.1	nM	PMID[515538]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[515538]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	23934.1	nM	PMID[515538]
NPT1255	Individual Protein	Sentrin-specific protease 8	Homo sapiens	IC50	n.a.	100000.0	nM	PMID[515538]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[515538]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[515538]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[515538]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	369.6	nM	PMID[515538]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	23778.1	nM	PMID[515538]

☑ 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 NPC44830 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	173
0.1-0.2	910
0.2-0.3	3254
0.3-0.4	12219
0.4-0.5	17642
0.5-0.6	6802
0.6-0.7	1364
0.7-0.8	287
0.8-0.85	33
0.85-0.9	9
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.961	High Similarity	NPC127343
0.925	High Similarity	NPC285773
0.9036	High Similarity	NPC322387
0.9024	High Similarity	NPC95965
0.8941	High Similarity	NPC86670
0.8941	High Similarity	NPC274455
0.8941	High Similarity	NPC70940
0.8929	High Similarity	NPC329064
0.8837	High Similarity	NPC86987
0.8556	High Similarity	NPC477767
0.8554	High Similarity	NPC288903
0.8506	High Similarity	NPC84288
0.8488	Intermediate Similarity	NPC477704
0.8488	Intermediate Similarity	NPC477693
0.8462	Intermediate Similarity	NPC271475
0.8409	Intermediate Similarity	NPC317645
0.8409	Intermediate Similarity	NPC141607
0.8409	Intermediate Similarity	NPC187725
0.8391	Intermediate Similarity	NPC9822
0.8353	Intermediate Similarity	NPC294134
0.8333	Intermediate Similarity	NPC172925
0.8333	Intermediate Similarity	NPC155429
0.8315	Intermediate Similarity	NPC323164
0.828	Intermediate Similarity	NPC136810
0.828	Intermediate Similarity	NPC133809
0.828	Intermediate Similarity	NPC225079
0.828	Intermediate Similarity	NPC264728
0.828	Intermediate Similarity	NPC94487
0.828	Intermediate Similarity	NPC128248
0.8214	Intermediate Similarity	NPC323103
0.8202	Intermediate Similarity	NPC110704
0.8191	Intermediate Similarity	NPC475978
0.8191	Intermediate Similarity	NPC474820
0.8132	Intermediate Similarity	NPC206764
0.8118	Intermediate Similarity	NPC270507
0.8072	Intermediate Similarity	NPC272260
0.8065	Intermediate Similarity	NPC120393
0.8049	Intermediate Similarity	NPC9796
0.8043	Intermediate Similarity	NPC469893
0.8043	Intermediate Similarity	NPC261947
0.8023	Intermediate Similarity	NPC267704
0.8021	Intermediate Similarity	NPC19136
0.8021	Intermediate Similarity	NPC329282
0.8	Intermediate Similarity	NPC103387
0.7979	Intermediate Similarity	NPC217621
0.7978	Intermediate Similarity	NPC231591
0.7976	Intermediate Similarity	NPC121800
0.7957	Intermediate Similarity	NPC293628
0.7957	Intermediate Similarity	NPC469890
0.7957	Intermediate Similarity	NPC10781
0.7957	Intermediate Similarity	NPC122493
0.7957	Intermediate Similarity	NPC469891
0.7957	Intermediate Similarity	NPC469892
0.7957	Intermediate Similarity	NPC226041
0.7957	Intermediate Similarity	NPC324569
0.7931	Intermediate Similarity	NPC475710
0.7917	Intermediate Similarity	NPC329556
0.7907	Intermediate Similarity	NPC477770
0.7889	Intermediate Similarity	NPC62765
0.7875	Intermediate Similarity	NPC208302
0.7875	Intermediate Similarity	NPC74458
0.7872	Intermediate Similarity	NPC229242
0.7872	Intermediate Similarity	NPC160548
0.7872	Intermediate Similarity	NPC175852
0.7872	Intermediate Similarity	NPC210529
0.7857	Intermediate Similarity	NPC142326
0.7857	Intermediate Similarity	NPC244933
0.7857	Intermediate Similarity	NPC94751
0.7857	Intermediate Similarity	NPC170484
0.7857	Intermediate Similarity	NPC85560
0.7826	Intermediate Similarity	NPC34243
0.7812	Intermediate Similarity	NPC304873
0.7812	Intermediate Similarity	NPC25458
0.7805	Intermediate Similarity	NPC189371
0.7791	Intermediate Similarity	NPC73637
0.7791	Intermediate Similarity	NPC121478
0.7789	Intermediate Similarity	NPC54647
0.7789	Intermediate Similarity	NPC7435
0.7789	Intermediate Similarity	NPC12730
0.7789	Intermediate Similarity	NPC245561
0.7789	Intermediate Similarity	NPC221825
0.7778	Intermediate Similarity	NPC285679
0.7778	Intermediate Similarity	NPC271437
0.7766	Intermediate Similarity	NPC253423
0.7766	Intermediate Similarity	NPC289201
0.7765	Intermediate Similarity	NPC164449
0.7765	Intermediate Similarity	NPC184030
0.7765	Intermediate Similarity	NPC477703
0.7755	Intermediate Similarity	NPC321670
0.7738	Intermediate Similarity	NPC103488
0.7732	Intermediate Similarity	NPC255676
0.7727	Intermediate Similarity	NPC123476
0.7708	Intermediate Similarity	NPC52472
0.7684	Intermediate Similarity	NPC329387
0.7684	Intermediate Similarity	NPC317280
0.7683	Intermediate Similarity	NPC108218
0.7683	Intermediate Similarity	NPC208075
0.7667	Intermediate Similarity	NPC325441
0.766	Intermediate Similarity	NPC61944
0.7647	Intermediate Similarity	NPC139901
0.7647	Intermediate Similarity	NPC151405
0.764	Intermediate Similarity	NPC318107
0.7629	Intermediate Similarity	NPC284477
0.7629	Intermediate Similarity	NPC474112
0.7619	Intermediate Similarity	NPC298023
0.7614	Intermediate Similarity	NPC44546
0.7604	Intermediate Similarity	NPC228435
0.76	Intermediate Similarity	NPC249811
0.759	Intermediate Similarity	NPC206800
0.759	Intermediate Similarity	NPC32203
0.7579	Intermediate Similarity	NPC270654
0.7576	Intermediate Similarity	NPC105899
0.7558	Intermediate Similarity	NPC285716
0.7558	Intermediate Similarity	NPC17408
0.7558	Intermediate Similarity	NPC157055
0.7556	Intermediate Similarity	NPC194326
0.7551	Intermediate Similarity	NPC164859
0.7551	Intermediate Similarity	NPC247976
0.7551	Intermediate Similarity	NPC160382
0.7551	Intermediate Similarity	NPC13426
0.7549	Intermediate Similarity	NPC475002
0.7549	Intermediate Similarity	NPC95126
0.7529	Intermediate Similarity	NPC76455
0.7529	Intermediate Similarity	NPC137847
0.7529	Intermediate Similarity	NPC224544
0.7528	Intermediate Similarity	NPC99482
0.7526	Intermediate Similarity	NPC282895
0.7526	Intermediate Similarity	NPC469481
0.7525	Intermediate Similarity	NPC31274
0.75	Intermediate Similarity	NPC258627
0.75	Intermediate Similarity	NPC37914
0.75	Intermediate Similarity	NPC179411
0.75	Intermediate Similarity	NPC322598
0.7475	Intermediate Similarity	NPC261573
0.7475	Intermediate Similarity	NPC120693
0.7475	Intermediate Similarity	NPC8931
0.7447	Intermediate Similarity	NPC261181
0.7442	Intermediate Similarity	NPC300205
0.7426	Intermediate Similarity	NPC20485
0.7426	Intermediate Similarity	NPC156648
0.7423	Intermediate Similarity	NPC325497
0.7412	Intermediate Similarity	NPC245966
0.7412	Intermediate Similarity	NPC329318
0.7404	Intermediate Similarity	NPC93287
0.7404	Intermediate Similarity	NPC477475
0.7404	Intermediate Similarity	NPC477476
0.7404	Intermediate Similarity	NPC287055
0.7404	Intermediate Similarity	NPC206414
0.7404	Intermediate Similarity	NPC306977
0.7404	Intermediate Similarity	NPC242957
0.74	Intermediate Similarity	NPC474307
0.74	Intermediate Similarity	NPC67043
0.74	Intermediate Similarity	NPC471186
0.74	Intermediate Similarity	NPC13495
0.7391	Intermediate Similarity	NPC220893
0.7386	Intermediate Similarity	NPC475199
0.7386	Intermediate Similarity	NPC283012
0.7386	Intermediate Similarity	NPC230068
0.7379	Intermediate Similarity	NPC319579
0.7374	Intermediate Similarity	NPC471317
0.7368	Intermediate Similarity	NPC130398
0.7363	Intermediate Similarity	NPC89377
0.7363	Intermediate Similarity	NPC69057
0.7356	Intermediate Similarity	NPC190567
0.7356	Intermediate Similarity	NPC164086
0.7356	Intermediate Similarity	NPC309279
0.7356	Intermediate Similarity	NPC95868
0.7353	Intermediate Similarity	NPC318327
0.7347	Intermediate Similarity	NPC473325
0.7347	Intermediate Similarity	NPC158623
0.734	Intermediate Similarity	NPC77273
0.7333	Intermediate Similarity	NPC294458
0.7333	Intermediate Similarity	NPC471721
0.7327	Intermediate Similarity	NPC475905
0.7327	Intermediate Similarity	NPC474111
0.7327	Intermediate Similarity	NPC100767
0.7327	Intermediate Similarity	NPC193640
0.7327	Intermediate Similarity	NPC329705
0.7327	Intermediate Similarity	NPC188677
0.7327	Intermediate Similarity	NPC317592
0.7327	Intermediate Similarity	NPC25385
0.7326	Intermediate Similarity	NPC285470
0.7326	Intermediate Similarity	NPC2785
0.7326	Intermediate Similarity	NPC50192
0.7326	Intermediate Similarity	NPC36342
0.732	Intermediate Similarity	NPC260000
0.732	Intermediate Similarity	NPC145052
0.732	Intermediate Similarity	NPC78701
0.732	Intermediate Similarity	NPC35448
0.7312	Intermediate Similarity	NPC213156
0.7312	Intermediate Similarity	NPC240108
0.7308	Intermediate Similarity	NPC474689
0.7308	Intermediate Similarity	NPC66208
0.7303	Intermediate Similarity	NPC273758
0.7273	Intermediate Similarity	NPC12936
0.7273	Intermediate Similarity	NPC145053
0.7273	Intermediate Similarity	NPC133050
0.7273	Intermediate Similarity	NPC273033
0.7264	Intermediate Similarity	NPC221275
0.7255	Intermediate Similarity	NPC21929

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 NPC44830 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	797
0.2-0.3	1498
0.3-0.4	3082
0.4-0.5	2205
0.5-0.6	1038
0.6-0.7	286
0.7-0.8	52
0.8-0.85	13
0.85-0.9	6
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9506	High Similarity	NPD4793	Discontinued
0.9487	High Similarity	NPD226	Approved
0.9277	High Similarity	NPD5346	Phase 2
0.9277	High Similarity	NPD5347	Phase 2
0.925	High Similarity	NPD9491	Approved
0.9103	High Similarity	NPD227	Approved
0.9103	High Similarity	NPD225	Approved
0.9048	High Similarity	NPD800	Approved
0.8941	High Similarity	NPD1089	Approved
0.8941	High Similarity	NPD1086	Approved
0.8941	High Similarity	NPD1090	Approved
0.8851	High Similarity	NPD5122	Clinical (unspecified phase)
0.875	High Similarity	NPD9490	Approved
0.8736	High Similarity	NPD1088	Approved
0.8621	High Similarity	NPD1239	Approved
0.8588	High Similarity	NPD1087	Approved
0.8539	High Similarity	NPD1693	Approved
0.8506	High Similarity	NPD3673	Approved
0.8506	High Similarity	NPD3672	Approved
0.8444	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD2066	Phase 3
0.837	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.8152	Intermediate Similarity	NPD1566	Phase 3
0.8152	Intermediate Similarity	NPD1564	Approved
0.8152	Intermediate Similarity	NPD1565	Approved
0.8065	Intermediate Similarity	NPD253	Approved
0.8043	Intermediate Similarity	NPD1989	Approved
0.8	Intermediate Similarity	NPD1932	Approved
0.7957	Intermediate Similarity	NPD9566	Approved
0.7917	Intermediate Similarity	NPD1930	Approved
0.7917	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1929	Approved
0.7889	Intermediate Similarity	NPD9256	Approved
0.7889	Intermediate Similarity	NPD9258	Approved
0.7872	Intermediate Similarity	NPD9495	Approved
0.7835	Intermediate Similarity	NPD5909	Discontinued
0.7826	Intermediate Similarity	NPD1563	Approved
0.7826	Intermediate Similarity	NPD1066	Discontinued
0.7732	Intermediate Similarity	NPD5765	Approved
0.77	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD9257	Approved
0.764	Intermediate Similarity	NPD9259	Approved
0.7624	Intermediate Similarity	NPD5278	Discontinued
0.7604	Intermediate Similarity	NPD7798	Approved
0.759	Intermediate Similarity	NPD9716	Approved
0.7576	Intermediate Similarity	NPD5048	Discontinued
0.7551	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6647	Phase 2
0.7549	Intermediate Similarity	NPD3643	Approved
0.7549	Intermediate Similarity	NPD3644	Approved
0.7549	Intermediate Similarity	NPD3642	Approved
0.7528	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD2329	Discontinued
0.75	Intermediate Similarity	NPD3971	Phase 1
0.75	Intermediate Similarity	NPD6685	Approved
0.75	Intermediate Similarity	NPD467	Phase 1
0.7451	Intermediate Similarity	NPD1317	Discontinued
0.7447	Intermediate Similarity	NPD1202	Approved
0.7423	Intermediate Similarity	NPD1067	Discontinued
0.7356	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3598	Phase 3
0.7333	Intermediate Similarity	NPD2650	Approved
0.7333	Intermediate Similarity	NPD2652	Approved
0.7273	Intermediate Similarity	NPD942	Approved
0.7264	Intermediate Similarity	NPD5951	Approved
0.7264	Intermediate Similarity	NPD2629	Approved
0.7212	Intermediate Similarity	NPD189	Phase 3
0.7212	Intermediate Similarity	NPD188	Approved
0.7143	Intermediate Similarity	NPD6912	Phase 3
0.713	Intermediate Similarity	NPD5162	Approved
0.7129	Intermediate Similarity	NPD1237	Approved
0.7115	Intermediate Similarity	NPD4234	Approved
0.7115	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4233	Approved
0.7115	Intermediate Similarity	NPD2067	Discontinued
0.7097	Intermediate Similarity	NPD1101	Approved
0.7075	Intermediate Similarity	NPD5277	Phase 2
0.7071	Intermediate Similarity	NPD1238	Approved
0.7059	Intermediate Similarity	NPD1018	Approved
0.7059	Intermediate Similarity	NPD1040	Phase 2
0.7053	Intermediate Similarity	NPD7609	Phase 3
0.7048	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD476	Approved
0.7019	Intermediate Similarity	NPD2182	Approved
0.7011	Intermediate Similarity	NPD9294	Approved
0.701	Intermediate Similarity	NPD9260	Approved
0.7009	Intermediate Similarity	NPD1280	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6010	Discontinued
0.6979	Remote Similarity	NPD7631	Approved
0.6972	Remote Similarity	NPD3797	Approved
0.697	Remote Similarity	NPD5926	Approved
0.6961	Remote Similarity	NPD164	Approved
0.6952	Remote Similarity	NPD1752	Approved
0.6952	Remote Similarity	NPD1756	Approved
0.6944	Remote Similarity	NPD747	Discontinued
0.6944	Remote Similarity	NPD1246	Approved
0.6937	Remote Similarity	NPD6993	Approved
0.6937	Remote Similarity	NPD4105	Approved
0.6937	Remote Similarity	NPD4102	Approved
0.6937	Remote Similarity	NPD6994	Approved
0.6937	Remote Similarity	NPD5981	Approved
0.6916	Remote Similarity	NPD7094	Approved
0.6916	Remote Similarity	NPD181	Approved
0.6916	Remote Similarity	NPD2607	Approved
0.6916	Remote Similarity	NPD6858	Approved
0.6915	Remote Similarity	NPD531	Approved
0.6907	Remote Similarity	NPD3718	Approved
0.6907	Remote Similarity	NPD3719	Approved
0.6887	Remote Similarity	NPD5927	Discontinued
0.6881	Remote Similarity	NPD255	Approved
0.6881	Remote Similarity	NPD1348	Approved
0.6881	Remote Similarity	NPD256	Approved
0.6875	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5306	Approved
0.6875	Remote Similarity	NPD5305	Approved
0.6852	Remote Similarity	NPD1681	Approved
0.6852	Remote Similarity	NPD1682	Approved
0.6852	Remote Similarity	NPD1680	Approved
0.6847	Remote Similarity	NPD3798	Phase 3
0.6847	Remote Similarity	NPD2617	Discontinued
0.6837	Remote Similarity	NPD4814	Discontinued
0.6837	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6049	Phase 2
0.6832	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD9508	Approved
0.6814	Remote Similarity	NPD3881	Discontinued
0.6814	Remote Similarity	NPD4135	Approved
0.6814	Remote Similarity	NPD4106	Approved
0.6814	Remote Similarity	NPD4136	Approved
0.6809	Remote Similarity	NPD9538	Approved
0.6809	Remote Similarity	NPD650	Approved
0.6789	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4766	Approved
0.6786	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1855	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD2860	Approved
0.6768	Remote Similarity	NPD2859	Approved
0.6762	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD9267	Approved
0.6762	Remote Similarity	NPD9264	Approved
0.6762	Remote Similarity	NPD9263	Approved
0.6757	Remote Similarity	NPD1758	Phase 1
0.6754	Remote Similarity	NPD3603	Phase 3
0.6754	Remote Similarity	NPD3131	Approved
0.6754	Remote Similarity	NPD4807	Approved
0.6754	Remote Similarity	NPD3132	Approved
0.6754	Remote Similarity	NPD4215	Approved
0.6754	Remote Similarity	NPD2608	Approved
0.6754	Remote Similarity	NPD2610	Approved
0.6754	Remote Similarity	NPD4217	Approved
0.6754	Remote Similarity	NPD2611	Approved
0.6754	Remote Similarity	NPD4218	Approved
0.6754	Remote Similarity	NPD4806	Approved
0.6754	Remote Similarity	NPD4216	Approved
0.6754	Remote Similarity	NPD2612	Approved
0.6754	Remote Similarity	NPD2609	Approved
0.6735	Remote Similarity	NPD719	Approved
0.6735	Remote Similarity	NPD720	Approved
0.6735	Remote Similarity	NPD1409	Phase 3
0.6733	Remote Similarity	NPD9712	Approved
0.6726	Remote Similarity	NPD2345	Approved
0.6726	Remote Similarity	NPD4199	Phase 3
0.6701	Remote Similarity	NPD530	Approved
0.67	Remote Similarity	NPD1875	Phase 1
0.67	Remote Similarity	NPD3495	Discontinued
0.6698	Remote Similarity	NPD74	Approved
0.6698	Remote Similarity	NPD9266	Approved
0.6697	Remote Similarity	NPD1370	Approved
0.6697	Remote Similarity	NPD1374	Approved
0.6697	Remote Similarity	NPD1371	Approved
0.6697	Remote Similarity	NPD1373	Approved
0.6696	Remote Similarity	NPD4479	Discontinued
0.6696	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1894	Discontinued
0.6696	Remote Similarity	NPD1759	Phase 1
0.6667	Remote Similarity	NPD4576	Approved
0.6667	Remote Similarity	NPD9568	Approved
0.6667	Remote Similarity	NPD4574	Approved
0.6667	Remote Similarity	NPD2933	Approved
0.6667	Remote Similarity	NPD4094	Approved
0.6667	Remote Similarity	NPD689	Discontinued
0.6667	Remote Similarity	NPD2934	Approved
0.6637	Remote Similarity	NPD1245	Approved
0.6634	Remote Similarity	NPD9710	Approved
0.6634	Remote Similarity	NPD9711	Approved
0.6633	Remote Similarity	NPD752	Approved
0.6633	Remote Similarity	NPD1508	Approved
0.6633	Remote Similarity	NPD6690	Approved
0.6632	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4761	Approved
0.6609	Remote Similarity	NPD4762	Approved
0.6609	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7610	Discontinued
0.6607	Remote Similarity	NPD2116	Approved
0.6607	Remote Similarity	NPD2115	Approved
0.6607	Remote Similarity	NPD2117	Pre-registration
0.6607	Remote Similarity	NPD6065	Approved
0.6606	Remote Similarity	NPD1279	Clinical (unspecified phase)

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