NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	186.07
Volume:	200.757
LogP:	2.754
LogD:	3.561
LogS:	-2.848
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.782
Synthetic Accessibility Score:	1.478
Fsp3:	0.083
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.589
MDCK Permeability:	4.603244087775238e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.589
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.342
Plasma Protein Binding (PPB):	95.37179565429688%
Volume Distribution (VD):	0.206
Pgp-substrate:	3.3487119674682617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.249
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.075
CYP2C19-substrate:	0.289
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.939
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.356
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	5.893
Half-life (T1/2):	0.86

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.271
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.233
Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.727
Carcinogencity:	0.551
Eye Corrosion:	0.212
Eye Irritation:	0.94
Respiratory Toxicity:	0.107

Download Data

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

Natural Product: NPC172925

Natural Product ID:	NPC172925
*Common Name:**	2-Naphthalen-1-Ylacetic Acid
IUPAC Name:	2-naphthalen-1-ylacetic acid
Synonyms:	Naphthalen-1-ylacetic acid
Standard InCHIKey:	PRPINYUDVPFIRX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14)
SMILES:	c1ccc2c(c1)cccc2CC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL428495
PubChem CID:	6862
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2690	Carapichea ipecacuanha	Species	Rubiaceae	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
AC50	4
IC50	3
Others	4
Potency	45

Activity Type	# Activity
Individual Protein	14
Organism	1
Others	41

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	10000.0	nM	PMID[513178]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	1157.7	nM	PMID[513179]
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[513180]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	92.0	nM	PMID[513179]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	43277.1	nM	PMID[513181]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	1230	nM	PubChem BioAssay data set
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	32000.0	nM	PMID[513175]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	32000.0	nM	PMID[513176]
NPT2	Others	Unspecified		IC50	=	233000.0	nM	PMID[513177]
NPT2	Others	Unspecified		Potency	=	1299.5	nM	PMID[513179]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[513179]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[513179]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[513178]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	580.5	nM	PMID[513179]
NPT2	Others	Unspecified		AC50	n.a.	8912.5	nM	PMID[513181]
NPT2	Others	Unspecified		Ac50	n.a.	1.122	uM	PMID[513181]
NPT2	Others	Unspecified		Ac50	n.a.	8.913	uM	PMID[513181]
NPT2	Others	Unspecified		Ac50	n.a.	10.0	uM	PMID[513182]
NPT2	Others	Unspecified		AC50	n.a.	10000.0	nM	PMID[513182]
NPT2	Others	Unspecified		Ac50	n.a.	1.413	uM	PMID[513181]
NPT2	Others	Unspecified		AC50	n.a.	17782.8	nM	PMID[513181]
NPT2	Others	Unspecified		AC50	n.a.	1412.5	nM	PMID[513181]
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	94.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	952.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	870.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	6001.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	3889.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	12.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	3063.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24336.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	38895.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	15089	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27535.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	194.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	389	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	12299.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	19493.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21872.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17228.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2433.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	544.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	691.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	15355.3	nM	PubChem BioAssay data set

☑ 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 NPC172925 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	260
0.1-0.2	1288
0.2-0.3	3317
0.3-0.4	11787
0.4-0.5	14468
0.5-0.6	9672
0.6-0.7	1647
0.7-0.8	227
0.8-0.85	22
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9101	High Similarity	NPC329064
0.88	High Similarity	NPC318327
0.8778	High Similarity	NPC322387
0.875	High Similarity	NPC285773
0.8673	High Similarity	NPC255676
0.8673	High Similarity	NPC329556
0.8544	High Similarity	NPC66208
0.85	High Similarity	NPC134120
0.8495	Intermediate Similarity	NPC70940
0.8495	Intermediate Similarity	NPC274455
0.8495	Intermediate Similarity	NPC86670
0.8469	Intermediate Similarity	NPC225079
0.8469	Intermediate Similarity	NPC133809
0.8469	Intermediate Similarity	NPC136810
0.8469	Intermediate Similarity	NPC128248
0.8416	Intermediate Similarity	NPC142326
0.8416	Intermediate Similarity	NPC94751
0.8409	Intermediate Similarity	NPC127343
0.8333	Intermediate Similarity	NPC44830
0.8317	Intermediate Similarity	NPC105899
0.8247	Intermediate Similarity	NPC261947
0.8191	Intermediate Similarity	NPC9822
0.8163	Intermediate Similarity	NPC226041
0.8152	Intermediate Similarity	NPC95965
0.8132	Intermediate Similarity	NPC288903
0.8095	Intermediate Similarity	NPC95126
0.8095	Intermediate Similarity	NPC475002
0.8081	Intermediate Similarity	NPC229242
0.8058	Intermediate Similarity	NPC37914
0.8021	Intermediate Similarity	NPC86987
0.8019	Intermediate Similarity	NPC186128
0.8	Intermediate Similarity	NPC328694
0.8	Intermediate Similarity	NPC221825
0.7982	Intermediate Similarity	NPC158157
0.7963	Intermediate Similarity	NPC186933
0.7961	Intermediate Similarity	NPC471186
0.7957	Intermediate Similarity	NPC294134
0.7921	Intermediate Similarity	NPC264728
0.787	Intermediate Similarity	NPC471721
0.7864	Intermediate Similarity	NPC329282
0.785	Intermediate Similarity	NPC79496
0.7849	Intermediate Similarity	NPC267704
0.7843	Intermediate Similarity	NPC304873
0.7843	Intermediate Similarity	NPC284477
0.7835	Intermediate Similarity	NPC317645
0.7835	Intermediate Similarity	NPC110704
0.7822	Intermediate Similarity	NPC217621
0.7812	Intermediate Similarity	NPC199567
0.781	Intermediate Similarity	NPC203732
0.7798	Intermediate Similarity	NPC221275
0.7788	Intermediate Similarity	NPC172483
0.7778	Intermediate Similarity	NPC93287
0.7767	Intermediate Similarity	NPC274443
0.7767	Intermediate Similarity	NPC247976
0.7755	Intermediate Similarity	NPC128645
0.7745	Intermediate Similarity	NPC282895
0.7723	Intermediate Similarity	NPC120393
0.7706	Intermediate Similarity	NPC196673
0.77	Intermediate Similarity	NPC469893
0.7692	Intermediate Similarity	NPC472221
0.7692	Intermediate Similarity	NPC472222
0.7677	Intermediate Similarity	NPC34243
0.7677	Intermediate Similarity	NPC261181
0.767	Intermediate Similarity	NPC244427
0.767	Intermediate Similarity	NPC25458
0.767	Intermediate Similarity	NPC222390
0.7658	Intermediate Similarity	NPC212891
0.7653	Intermediate Similarity	NPC187725
0.7653	Intermediate Similarity	NPC141607
0.7647	Intermediate Similarity	NPC228435
0.7636	Intermediate Similarity	NPC306740
0.7629	Intermediate Similarity	NPC418308
0.7629	Intermediate Similarity	NPC325709
0.7624	Intermediate Similarity	NPC270654
0.7624	Intermediate Similarity	NPC469892
0.7624	Intermediate Similarity	NPC469890
0.7624	Intermediate Similarity	NPC156021
0.7624	Intermediate Similarity	NPC469891
0.7624	Intermediate Similarity	NPC253423
0.7593	Intermediate Similarity	NPC474057
0.7589	Intermediate Similarity	NPC228318
0.7589	Intermediate Similarity	NPC45794
0.7586	Intermediate Similarity	NPC318067
0.7573	Intermediate Similarity	NPC469481
0.7551	Intermediate Similarity	NPC62765
0.7551	Intermediate Similarity	NPC277277
0.7549	Intermediate Similarity	NPC160548
0.7549	Intermediate Similarity	NPC210529
0.7549	Intermediate Similarity	NPC175852
0.7549	Intermediate Similarity	NPC271475
0.7547	Intermediate Similarity	NPC83409
0.7547	Intermediate Similarity	NPC244933
0.7547	Intermediate Similarity	NPC100767
0.7547	Intermediate Similarity	NPC85560
0.7547	Intermediate Similarity	NPC185763
0.7525	Intermediate Similarity	NPC61944
0.7523	Intermediate Similarity	NPC292834
0.7523	Intermediate Similarity	NPC471189
0.7523	Intermediate Similarity	NPC471188
0.7522	Intermediate Similarity	NPC318173
0.7521	Intermediate Similarity	NPC236189
0.7521	Intermediate Similarity	NPC111088
0.75	Intermediate Similarity	NPC155429
0.7477	Intermediate Similarity	NPC476357
0.7477	Intermediate Similarity	NPC112903
0.7477	Intermediate Similarity	NPC156648
0.7477	Intermediate Similarity	NPC21929
0.7477	Intermediate Similarity	NPC211439
0.7477	Intermediate Similarity	NPC249811
0.7476	Intermediate Similarity	NPC476042
0.7475	Intermediate Similarity	NPC103346
0.7455	Intermediate Similarity	NPC143768
0.7455	Intermediate Similarity	NPC286222
0.7451	Intermediate Similarity	NPC289201
0.7451	Intermediate Similarity	NPC477767
0.7447	Intermediate Similarity	NPC323103
0.7431	Intermediate Similarity	NPC265513
0.7431	Intermediate Similarity	NPC167504
0.7431	Intermediate Similarity	NPC210089
0.7426	Intermediate Similarity	NPC206764
0.7419	Intermediate Similarity	NPC121800
0.7414	Intermediate Similarity	NPC167323
0.7414	Intermediate Similarity	NPC269923
0.7411	Intermediate Similarity	NPC9274
0.7407	Intermediate Similarity	NPC85493
0.7404	Intermediate Similarity	NPC52472
0.7404	Intermediate Similarity	NPC42211
0.74	Intermediate Similarity	NPC323164
0.7391	Intermediate Similarity	NPC133389
0.7391	Intermediate Similarity	NPC183339
0.7391	Intermediate Similarity	NPC234337
0.7387	Intermediate Similarity	NPC67377
0.7374	Intermediate Similarity	NPC19256
0.7368	Intermediate Similarity	NPC270507
0.7364	Intermediate Similarity	NPC280789
0.7358	Intermediate Similarity	NPC249067
0.7358	Intermediate Similarity	NPC114594
0.7347	Intermediate Similarity	NPC477704
0.7347	Intermediate Similarity	NPC267262
0.7347	Intermediate Similarity	NPC477693
0.7333	Intermediate Similarity	NPC320891
0.7328	Intermediate Similarity	NPC241001
0.7327	Intermediate Similarity	NPC289883
0.732	Intermediate Similarity	NPC318107
0.7312	Intermediate Similarity	NPC170484
0.7312	Intermediate Similarity	NPC272260
0.7308	Intermediate Similarity	NPC118343
0.7308	Intermediate Similarity	NPC7435
0.7308	Intermediate Similarity	NPC245561
0.7304	Intermediate Similarity	NPC202015
0.7304	Intermediate Similarity	NPC42657
0.7297	Intermediate Similarity	NPC470253
0.729	Intermediate Similarity	NPC209632
0.7288	Intermediate Similarity	NPC328107
0.7288	Intermediate Similarity	NPC85511
0.7283	Intermediate Similarity	NPC9796
0.7282	Intermediate Similarity	NPC324569
0.7273	Intermediate Similarity	NPC260818
0.7273	Intermediate Similarity	NPC231591
0.7273	Intermediate Similarity	NPC113307
0.7273	Intermediate Similarity	NPC133308
0.7265	Intermediate Similarity	NPC369
0.7265	Intermediate Similarity	NPC293831
0.7264	Intermediate Similarity	NPC160382
0.7264	Intermediate Similarity	NPC60679
0.7264	Intermediate Similarity	NPC13426
0.7263	Intermediate Similarity	NPC103387
0.7255	Intermediate Similarity	NPC472880
0.7253	Intermediate Similarity	NPC189371
0.7248	Intermediate Similarity	NPC281604
0.7248	Intermediate Similarity	NPC475006
0.7241	Intermediate Similarity	NPC478121
0.7238	Intermediate Similarity	NPC473325
0.7238	Intermediate Similarity	NPC94487
0.7234	Intermediate Similarity	NPC95868
0.7232	Intermediate Similarity	NPC294458
0.7222	Intermediate Similarity	NPC317592
0.7216	Intermediate Similarity	NPC475710
0.7212	Intermediate Similarity	NPC329387
0.7212	Intermediate Similarity	NPC49994
0.7212	Intermediate Similarity	NPC317280
0.7207	Intermediate Similarity	NPC158282
0.7207	Intermediate Similarity	NPC321852
0.7204	Intermediate Similarity	NPC224544
0.7203	Intermediate Similarity	NPC121168
0.7203	Intermediate Similarity	NPC176208
0.7203	Intermediate Similarity	NPC244351
0.7203	Intermediate Similarity	NPC283514
0.72	Intermediate Similarity	NPC84288
0.72	Intermediate Similarity	NPC26224
0.72	Intermediate Similarity	NPC173413
0.7196	Intermediate Similarity	NPC120693
0.7196	Intermediate Similarity	NPC31786
0.7196	Intermediate Similarity	NPC269644
0.7196	Intermediate Similarity	NPC261573
0.7196	Intermediate Similarity	NPC8931
0.7193	Intermediate Similarity	NPC242764
0.7193	Intermediate Similarity	NPC105141
0.7193	Intermediate Similarity	NPC469843
0.7188	Intermediate Similarity	NPC273758

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 NPC172925 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	918
0.2-0.3	1216
0.3-0.4	3002
0.4-0.5	2381
0.5-0.6	1023
0.6-0.7	281
0.7-0.8	42
0.8-0.85	12
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD688	Clinical (unspecified phase)
0.9222	High Similarity	NPD1239	Approved
0.875	High Similarity	NPD9491	Approved
0.8737	High Similarity	NPD1564	Approved
0.8737	High Similarity	NPD1566	Phase 3
0.8737	High Similarity	NPD1565	Approved
0.8673	High Similarity	NPD1930	Approved
0.8673	High Similarity	NPD1931	Clinical (unspecified phase)
0.8673	High Similarity	NPD1929	Approved
0.8523	High Similarity	NPD226	Approved
0.8495	Intermediate Similarity	NPD1089	Approved
0.8495	Intermediate Similarity	NPD1086	Approved
0.8495	Intermediate Similarity	NPD1090	Approved
0.8421	Intermediate Similarity	NPD1563	Approved
0.8387	Intermediate Similarity	NPD800	Approved
0.8316	Intermediate Similarity	NPD1088	Approved
0.8295	Intermediate Similarity	NPD9490	Approved
0.8247	Intermediate Similarity	NPD1989	Approved
0.82	Intermediate Similarity	NPD1932	Approved
0.8182	Intermediate Similarity	NPD2066	Phase 3
0.8182	Intermediate Similarity	NPD225	Approved
0.8182	Intermediate Similarity	NPD227	Approved
0.8172	Intermediate Similarity	NPD1087	Approved
0.8144	Intermediate Similarity	NPD1693	Approved
0.8131	Intermediate Similarity	NPD5951	Approved
0.7979	Intermediate Similarity	NPD4793	Discontinued
0.7857	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5346	Phase 2
0.7812	Intermediate Similarity	NPD5347	Phase 2
0.7736	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2329	Discontinued
0.77	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1202	Approved
0.7551	Intermediate Similarity	NPD9256	Approved
0.7551	Intermediate Similarity	NPD9258	Approved
0.7549	Intermediate Similarity	NPD9495	Approved
0.7521	Intermediate Similarity	NPD1283	Approved
0.7391	Intermediate Similarity	NPD2345	Approved
0.7379	Intermediate Similarity	NPD253	Approved
0.7374	Intermediate Similarity	NPD3673	Approved
0.7374	Intermediate Similarity	NPD3672	Approved
0.7358	Intermediate Similarity	NPD5909	Discontinued
0.7358	Intermediate Similarity	NPD1237	Approved
0.7321	Intermediate Similarity	NPD2629	Approved
0.732	Intermediate Similarity	NPD9259	Approved
0.732	Intermediate Similarity	NPD9257	Approved
0.7308	Intermediate Similarity	NPD1238	Approved
0.7273	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5618	Discontinued
0.7265	Intermediate Similarity	NPD1281	Approved
0.7234	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD1280	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD4479	Discontinued
0.7213	Intermediate Similarity	NPD7008	Discontinued
0.7196	Intermediate Similarity	NPD164	Approved
0.7193	Intermediate Similarity	NPD3797	Approved
0.7188	Intermediate Similarity	NPD3971	Phase 1
0.7179	Intermediate Similarity	NPD3881	Discontinued
0.7167	Intermediate Similarity	NPD1164	Approved
0.7158	Intermediate Similarity	NPD942	Approved
0.7155	Intermediate Similarity	NPD1855	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7798	Approved
0.713	Intermediate Similarity	NPD6065	Approved
0.7117	Intermediate Similarity	NPD3644	Approved
0.7117	Intermediate Similarity	NPD3643	Approved
0.7117	Intermediate Similarity	NPD3642	Approved
0.7115	Intermediate Similarity	NPD9566	Approved
0.7103	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD650	Approved
0.7069	Intermediate Similarity	NPD3798	Phase 3
0.7059	Intermediate Similarity	NPD1508	Approved
0.7059	Intermediate Similarity	NPD3880	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5162	Approved
0.7027	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4105	Approved
0.7009	Intermediate Similarity	NPD6993	Approved
0.7009	Intermediate Similarity	NPD6994	Approved
0.7009	Intermediate Similarity	NPD4102	Approved
0.7	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1201	Approved
0.6972	Remote Similarity	NPD1018	Approved
0.6972	Remote Similarity	NPD5048	Discontinued
0.6964	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7609	Phase 3
0.6952	Remote Similarity	NPD3495	Discontinued
0.6949	Remote Similarity	NPD4199	Phase 3
0.6944	Remote Similarity	NPD5765	Approved
0.6942	Remote Similarity	NPD1574	Approved
0.6937	Remote Similarity	NPD2182	Approved
0.693	Remote Similarity	NPD3598	Phase 3
0.693	Remote Similarity	NPD2652	Approved
0.693	Remote Similarity	NPD2650	Approved
0.6923	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6049	Phase 2
0.6917	Remote Similarity	NPD1608	Approved
0.6893	Remote Similarity	NPD7631	Approved
0.6891	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4135	Approved
0.6891	Remote Similarity	NPD4136	Approved
0.6891	Remote Similarity	NPD4879	Approved
0.6891	Remote Similarity	NPD4106	Approved
0.6875	Remote Similarity	NPD1317	Discontinued
0.6875	Remote Similarity	NPD1752	Approved
0.6875	Remote Similarity	NPD1756	Approved
0.687	Remote Similarity	NPD4766	Approved
0.687	Remote Similarity	NPD1246	Approved
0.6869	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1651	Approved
0.6857	Remote Similarity	NPD1843	Approved
0.6847	Remote Similarity	NPD2342	Discontinued
0.6842	Remote Similarity	NPD7094	Approved
0.6842	Remote Similarity	NPD6858	Approved
0.6842	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD1066	Discontinued
0.6814	Remote Similarity	NPD5927	Discontinued
0.6807	Remote Similarity	NPD5306	Approved
0.6807	Remote Similarity	NPD3019	Approved
0.6807	Remote Similarity	NPD2932	Approved
0.6807	Remote Similarity	NPD5305	Approved
0.6792	Remote Similarity	NPD1875	Phase 1
0.6789	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5406	Approved
0.6769	Remote Similarity	NPD5404	Approved
0.6769	Remote Similarity	NPD5405	Approved
0.6769	Remote Similarity	NPD5408	Approved
0.6762	Remote Similarity	NPD9260	Approved
0.6757	Remote Similarity	NPD6685	Approved
0.6757	Remote Similarity	NPD467	Phase 1
0.6754	Remote Similarity	NPD9508	Approved
0.6752	Remote Similarity	NPD4574	Approved
0.6752	Remote Similarity	NPD4576	Approved
0.6748	Remote Similarity	NPD1470	Approved
0.6746	Remote Similarity	NPD3764	Approved
0.6726	Remote Similarity	NPD4234	Approved
0.6726	Remote Similarity	NPD4233	Approved
0.6726	Remote Similarity	NPD5278	Discontinued
0.6724	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1245	Approved
0.6723	Remote Similarity	NPD5981	Approved
0.6705	Remote Similarity	NPD675	Discontinued
0.6702	Remote Similarity	NPD9716	Approved
0.6696	Remote Similarity	NPD7635	Approved
0.6696	Remote Similarity	NPD2607	Approved
0.6696	Remote Similarity	NPD181	Approved
0.6695	Remote Similarity	NPD7610	Discontinued
0.6694	Remote Similarity	NPD4807	Approved
0.6694	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD4806	Approved
0.6667	Remote Similarity	NPD188	Approved
0.6667	Remote Similarity	NPD531	Approved
0.6667	Remote Similarity	NPD1101	Approved
0.6667	Remote Similarity	NPD719	Approved
0.6667	Remote Similarity	NPD3020	Approved
0.6667	Remote Similarity	NPD720	Approved
0.6667	Remote Similarity	NPD6966	Discovery
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD1040	Phase 2
0.6667	Remote Similarity	NPD189	Phase 3
0.6641	Remote Similarity	NPD4476	Approved
0.6641	Remote Similarity	NPD2979	Phase 3
0.6641	Remote Similarity	NPD4477	Approved
0.6639	Remote Similarity	NPD1894	Discontinued
0.6639	Remote Similarity	NPD7009	Phase 2
0.6639	Remote Similarity	NPD4878	Approved
0.6638	Remote Similarity	NPD6010	Discontinued
0.6638	Remote Similarity	NPD1374	Approved
0.6638	Remote Similarity	NPD1370	Approved
0.6638	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD1373	Approved
0.6638	Remote Similarity	NPD1371	Approved
0.6636	Remote Similarity	NPD6647	Phase 2
0.6636	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD2313	Discontinued
0.6613	Remote Similarity	NPD6564	Approved
0.6613	Remote Similarity	NPD6563	Approved
0.6613	Remote Similarity	NPD6565	Approved
0.661	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1616	Discontinued
0.6604	Remote Similarity	NPD3772	Phase 3
0.6591	Remote Similarity	NPD2346	Discontinued
0.6571	Remote Similarity	NPD752	Approved
0.6567	Remote Similarity	NPD7003	Approved
0.6562	Remote Similarity	NPD9294	Approved
0.6562	Remote Similarity	NPD6663	Approved
0.6557	Remote Similarity	NPD3131	Approved
0.6557	Remote Similarity	NPD4218	Approved
0.6557	Remote Similarity	NPD4217	Approved
0.6557	Remote Similarity	NPD2609	Approved
0.6557	Remote Similarity	NPD2612	Approved
0.6557	Remote Similarity	NPD2608	Approved
0.6557	Remote Similarity	NPD4215	Approved
0.6557	Remote Similarity	NPD3132	Approved
0.6557	Remote Similarity	NPD4216	Approved
0.6557	Remote Similarity	NPD2610	Approved
0.6557	Remote Similarity	NPD2611	Approved
0.6552	Remote Similarity	NPD5277	Phase 2

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