NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	208.07
Volume:	212.234
LogP:	1.643
LogD:	1.391
LogS:	-2.985
# Rotatable Bonds:	4
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.766
Synthetic Accessibility Score:	1.687
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.606
MDCK Permeability:	1.0461712008691393e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.853
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.604

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.414
Plasma Protein Binding (PPB):	74.51395416259766%
Volume Distribution (VD):	0.255
Pgp-substrate:	14.13071346282959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.104
CYP1A2-substrate:	0.817
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.789
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	7.898
Half-life (T1/2):	0.904

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.332
Drug-inuced Liver Injury (DILI):	0.89
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.884
Carcinogencity:	0.741
Eye Corrosion:	0.545
Eye Irritation:	0.97
Respiratory Toxicity:	0.289

Download Data

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

Natural Product: NPC294941

Natural Product ID:	NPC294941
*Common Name:**	O,O'-Dimethylcaffeic Acid
IUPAC Name:	(E)-3-(3,4-dimethoxyphenyl)prop-2-enoic acid
Synonyms:	O,O'-Dimethylcaffeic Acid
Standard InCHIKey:	HJBWJAPEBGSQPR-GQCTYLIASA-N
Standard InCHI:	InChI=1S/C11H12O4/c1-14-9-5-3-8(4-6-11(12)13)7-10(9)15-2/h3-7H,1-2H3,(H,12,13)/b6-4+
SMILES:	COc1cc(/C=C/C(=O)O)ccc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL320295
PubChem CID:	717531
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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

☑ 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
EC50	6
IC50	11
MIC	6
Others	22
Potency	17

Activity Type	# Activity
Cell Line	8
Individual Protein	19
NON-MOLECULAR	11
Organism	7
Others	16
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	9.0	%	PMID[455542]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	<	30.0	%	PMID[455545]
NPT453	Cell Line	HT-1080	Homo sapiens	EC50	>	480000.0	nM	PMID[455546]
NPT81	Cell Line	A549	Homo sapiens	EC50	>	480000.0	nM	PMID[455546]
NPT165	Cell Line	HeLa	Homo sapiens	EC50	>	480000.0	nM	PMID[455546]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	>	100.0	uM	PMID[455548]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	25118.9	nM	PMID[455549]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	39810.7	nM	PMID[455550]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	35481.3	nM	PMID[455549]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[455551]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	794.3	nM	PMID[455549]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	25118.9	nM	PMID[455549]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	22387.2	nM	PMID[455551]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	19952.6	nM	PMID[455550]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	12589.3	nM	PMID[455549]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	350000.0	nM	PMID[455553]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[455549]
NPT2966	Individual Protein	T-complex protein 1 subunit beta	Macaaca fascicularis	Potency	n.a.	8912.5	nM	PMID[455551]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	5.8	nM	PMID[455551]
NPT466	Cell Line	U-937	Homo sapiens	CC50	>	2000000.0	nM	PMID[455556]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	2000000.0	nM	PMID[455556]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	=	534660.0	nM	PMID[455560]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	100000.0	nM	PMID[455543]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	1.0	%	PMID[455543]
NPT35	Others	n.a.		log K	=	1.56	n.a.	PMID[455544]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	480000.0	nM	PMID[455546]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	480300.0	nM	PMID[455547]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	446.7	nM	PMID[455551]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	22387.2	nM	PMID[455549]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	39810.7	nM	PMID[455549]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	10.0	%	PMID[455552]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	9.0	%	PMID[455552]
NPT35	Others	n.a.		Inhibition	=	56.0	%	PMID[455552]
NPT2	Others	Unspecified		Inhibition	=	23.0	%	PMID[455552]
NPT2	Others	Unspecified		Potency	n.a.	29092.9	nM	PMID[455551]
NPT1	Others	Radical scavenging activity		EC50	>	250000.0	nM	PMID[455553]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	240.0	nM	PMID[455554]
NPT35	Others	n.a.		pKa	=	4.55	n.a.	PMID[455557]
NPT2	Others	Unspecified		Inhibition	=	75.6	%	PMID[455557]
NPT2	Others	Unspecified		IC50	=	206000.0	nM	PMID[455557]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	108.8	%	PMID[455558]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	91.89	%	PMID[455558]
NPT2	Others	Unspecified		Potency	n.a.	35481.3	nM	PMID[455549]
NPT27	Others	Unspecified		Ratio	=	1.1	n.a.	PMID[455559]
NPT27	Others	Unspecified		Papp	=	21.7	ucm/s	PMID[455559]
NPT27	Others	Unspecified		Papp	=	19.9	ucm/s	PMID[455559]
NPT35	Others	n.a.		LogD	=	-1.01	n.a.	PMID[455559]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	600000.0	nM	PMID[455560]
NPT2	Others	Unspecified		Ratio CC50/IC50	<	0.89	n.a.	PMID[455560]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	4.0	ug.mL-1	PMID[455563]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	2.0	ug.mL-1	PMID[455563]
NPT2	Others	Unspecified		IC50	>	250000.0	nM	PMID[455563]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	32.0	ug.mL-1	PMID[455563]
NPT22587	SINGLE PROTEIN	Taste receptor type 2 member 39	Homo sapiens	Inhibition	=	45.0	%	PMID[455564]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[455565]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[455565]

☑ 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 NPC294941 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	1787
0.2-0.3	5511
0.3-0.4	12270
0.4-0.5	5030
0.5-0.6	6373
0.6-0.7	9006
0.7-0.8	2129
0.8-0.85	210
0.85-0.9	83
0.9-0.95	29
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9636	High Similarity	NPC137537
0.9636	High Similarity	NPC124916
0.9636	High Similarity	NPC70744
0.9636	High Similarity	NPC272471
0.9636	High Similarity	NPC107588
0.9636	High Similarity	NPC164706
0.955	High Similarity	NPC37858
0.9464	High Similarity	NPC202474
0.9381	High Similarity	NPC204466
0.9375	High Similarity	NPC57501
0.9298	High Similarity	NPC70752
0.9298	High Similarity	NPC310373
0.9292	High Similarity	NPC2058
0.9196	High Similarity	NPC199209
0.9196	High Similarity	NPC212643
0.9196	High Similarity	NPC280001
0.9151	High Similarity	NPC288760
0.9115	High Similarity	NPC277460
0.9083	High Similarity	NPC179309
0.906	High Similarity	NPC246704
0.906	High Similarity	NPC146886
0.906	High Similarity	NPC60517
0.906	High Similarity	NPC20443
0.9057	High Similarity	NPC2518
0.9035	High Similarity	NPC69670
0.9027	High Similarity	NPC39793
0.9	High Similarity	NPC245552
0.9	High Similarity	NPC226250
0.8983	High Similarity	NPC300326
0.8983	High Similarity	NPC58279
0.8983	High Similarity	NPC289459
0.8981	High Similarity	NPC227894
0.8957	High Similarity	NPC222175
0.8947	High Similarity	NPC205502
0.8908	High Similarity	NPC213552
0.8908	High Similarity	NPC120225
0.8879	High Similarity	NPC471877
0.8879	High Similarity	NPC109083
0.8879	High Similarity	NPC224814
0.8879	High Similarity	NPC60962
0.8879	High Similarity	NPC269843
0.8879	High Similarity	NPC14007
0.8879	High Similarity	NPC189844
0.8868	High Similarity	NPC310905
0.8868	High Similarity	NPC12714
0.8839	High Similarity	NPC95381
0.8839	High Similarity	NPC303522
0.8824	High Similarity	NPC27352
0.8818	High Similarity	NPC233731
0.8818	High Similarity	NPC36108
0.8818	High Similarity	NPC7097
0.8818	High Similarity	NPC246358
0.8803	High Similarity	NPC114845
0.8803	High Similarity	NPC194416
0.8803	High Similarity	NPC177291
0.8772	High Similarity	NPC268317
0.8761	High Similarity	NPC328593
0.8761	High Similarity	NPC33749
0.8761	High Similarity	NPC261453
0.8761	High Similarity	NPC217472
0.876	High Similarity	NPC478215
0.876	High Similarity	NPC110313
0.876	High Similarity	NPC109275
0.8729	High Similarity	NPC286573
0.8729	High Similarity	NPC288238
0.8718	High Similarity	NPC158949
0.8704	High Similarity	NPC292792
0.8696	High Similarity	NPC65791
0.8696	High Similarity	NPC185738
0.8689	High Similarity	NPC83062
0.8689	High Similarity	NPC48315
0.8684	High Similarity	NPC233669
0.8684	High Similarity	NPC474967
0.8661	High Similarity	NPC257124
0.8661	High Similarity	NPC156840
0.8661	High Similarity	NPC55300
0.8661	High Similarity	NPC78918
0.8661	High Similarity	NPC8547
0.8661	High Similarity	NPC139617
0.8661	High Similarity	NPC173746
0.8655	High Similarity	NPC229084
0.8655	High Similarity	NPC160900
0.8655	High Similarity	NPC238810
0.8655	High Similarity	NPC18984
0.8655	High Similarity	NPC106659
0.8644	High Similarity	NPC193484
0.8624	High Similarity	NPC227255
0.8621	High Similarity	NPC212743
0.8621	High Similarity	NPC159916
0.8618	High Similarity	NPC285776
0.8611	High Similarity	NPC179686
0.8609	High Similarity	NPC281277
0.8609	High Similarity	NPC111225
0.8584	High Similarity	NPC165646
0.8584	High Similarity	NPC131530
0.8571	High Similarity	NPC137685
0.8571	High Similarity	NPC114298
0.8545	High Similarity	NPC294902
0.8545	High Similarity	NPC1075
0.8545	High Similarity	NPC1786
0.8532	High Similarity	NPC109637
0.8519	High Similarity	NPC94343
0.8512	High Similarity	NPC271985
0.8512	High Similarity	NPC280767
0.85	High Similarity	NPC4181
0.85	High Similarity	NPC21238
0.85	High Similarity	NPC164778
0.85	High Similarity	NPC242372
0.85	High Similarity	NPC257976
0.8482	Intermediate Similarity	NPC127326
0.848	Intermediate Similarity	NPC245120
0.848	Intermediate Similarity	NPC5423
0.848	Intermediate Similarity	NPC111888
0.8468	Intermediate Similarity	NPC258171
0.8462	Intermediate Similarity	NPC309434
0.8462	Intermediate Similarity	NPC275519
0.8462	Intermediate Similarity	NPC203124
0.8455	Intermediate Similarity	NPC128730
0.8443	Intermediate Similarity	NPC127604
0.8443	Intermediate Similarity	NPC154275
0.8443	Intermediate Similarity	NPC276014
0.843	Intermediate Similarity	NPC312404
0.843	Intermediate Similarity	NPC273686
0.8426	Intermediate Similarity	NPC253746
0.8421	Intermediate Similarity	NPC199462
0.8417	Intermediate Similarity	NPC256167
0.8413	Intermediate Similarity	NPC283823
0.8413	Intermediate Similarity	NPC475468
0.8413	Intermediate Similarity	NPC159418
0.8411	Intermediate Similarity	NPC175298
0.8403	Intermediate Similarity	NPC267064
0.8403	Intermediate Similarity	NPC307253
0.839	Intermediate Similarity	NPC299406
0.839	Intermediate Similarity	NPC241634
0.8378	Intermediate Similarity	NPC176971
0.8378	Intermediate Similarity	NPC326447
0.8376	Intermediate Similarity	NPC293619
0.8374	Intermediate Similarity	NPC194841
0.8374	Intermediate Similarity	NPC281020
0.8374	Intermediate Similarity	NPC5018
0.8374	Intermediate Similarity	NPC123228
0.8374	Intermediate Similarity	NPC276466
0.8374	Intermediate Similarity	NPC123722
0.8374	Intermediate Similarity	NPC151167
0.8361	Intermediate Similarity	NPC85830
0.8346	Intermediate Similarity	NPC92830
0.8346	Intermediate Similarity	NPC471110
0.8346	Intermediate Similarity	NPC135127
0.8346	Intermediate Similarity	NPC111635
0.8333	Intermediate Similarity	NPC195873
0.8305	Intermediate Similarity	NPC470626
0.8305	Intermediate Similarity	NPC255675
0.8304	Intermediate Similarity	NPC151530
0.8304	Intermediate Similarity	NPC157473
0.8293	Intermediate Similarity	NPC84076
0.8293	Intermediate Similarity	NPC90128
0.8293	Intermediate Similarity	NPC303680
0.8293	Intermediate Similarity	NPC179777
0.8291	Intermediate Similarity	NPC221049
0.8288	Intermediate Similarity	NPC127676
0.8273	Intermediate Similarity	NPC304638
0.8257	Intermediate Similarity	NPC13755
0.825	Intermediate Similarity	NPC470849
0.825	Intermediate Similarity	NPC470848
0.825	Intermediate Similarity	NPC225245
0.825	Intermediate Similarity	NPC295317
0.8246	Intermediate Similarity	NPC31279
0.824	Intermediate Similarity	NPC304622
0.8235	Intermediate Similarity	NPC181969
0.8235	Intermediate Similarity	NPC24474
0.8235	Intermediate Similarity	NPC141791
0.8235	Intermediate Similarity	NPC311595
0.8235	Intermediate Similarity	NPC320987
0.8235	Intermediate Similarity	NPC263386
0.8235	Intermediate Similarity	NPC135961
0.8226	Intermediate Similarity	NPC117237
0.8226	Intermediate Similarity	NPC32163
0.8226	Intermediate Similarity	NPC16651
0.8226	Intermediate Similarity	NPC203719
0.822	Intermediate Similarity	NPC259638
0.822	Intermediate Similarity	NPC164386
0.822	Intermediate Similarity	NPC240664
0.8217	Intermediate Similarity	NPC90431
0.8217	Intermediate Similarity	NPC120852
0.8217	Intermediate Similarity	NPC157554
0.8217	Intermediate Similarity	NPC37468
0.8211	Intermediate Similarity	NPC87113
0.8211	Intermediate Similarity	NPC173608
0.8205	Intermediate Similarity	NPC296526
0.8203	Intermediate Similarity	NPC155098
0.8198	Intermediate Similarity	NPC79672
0.8198	Intermediate Similarity	NPC474603
0.8198	Intermediate Similarity	NPC283546
0.8198	Intermediate Similarity	NPC52087
0.8198	Intermediate Similarity	NPC12987
0.8197	Intermediate Similarity	NPC470887
0.8197	Intermediate Similarity	NPC279379
0.8197	Intermediate Similarity	NPC108545
0.8197	Intermediate Similarity	NPC163083
0.819	Intermediate Similarity	NPC165106

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 NPC294941 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	1033
0.2-0.3	1659
0.3-0.4	2746
0.4-0.5	1759
0.5-0.6	1026
0.6-0.7	611
0.7-0.8	75
0.8-0.85	5
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8807	High Similarity	NPD1358	Approved
0.8696	High Similarity	NPD5536	Phase 2
0.8661	High Similarity	NPD228	Approved
0.8655	High Similarity	NPD4379	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD3134	Approved
0.8235	Intermediate Similarity	NPD1357	Approved
0.8226	Intermediate Similarity	NPD9494	Approved
0.819	Intermediate Similarity	NPD5283	Phase 1
0.8167	Intermediate Similarity	NPD4626	Approved
0.7984	Intermediate Similarity	NPD447	Suspended
0.7951	Intermediate Similarity	NPD3496	Discontinued
0.7787	Intermediate Similarity	NPD5691	Approved
0.7652	Intermediate Similarity	NPD9697	Approved
0.7636	Intermediate Similarity	NPD9296	Approved
0.7619	Intermediate Similarity	NPD2982	Phase 2
0.7619	Intermediate Similarity	NPD2983	Phase 2
0.7609	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2684	Approved
0.76	Intermediate Similarity	NPD3705	Approved
0.754	Intermediate Similarity	NPD2981	Phase 2
0.7538	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD7843	Approved
0.75	Intermediate Similarity	NPD5535	Approved
0.746	Intermediate Similarity	NPD422	Phase 1
0.7459	Intermediate Similarity	NPD7157	Approved
0.7444	Intermediate Similarity	NPD230	Phase 1
0.744	Intermediate Similarity	NPD1778	Approved
0.7438	Intermediate Similarity	NPD1241	Discontinued
0.7424	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD1283	Approved
0.7419	Intermediate Similarity	NPD9545	Approved
0.7405	Intermediate Similarity	NPD7095	Approved
0.7402	Intermediate Similarity	NPD9717	Approved
0.7394	Intermediate Similarity	NPD1653	Approved
0.7391	Intermediate Similarity	NPD291	Approved
0.7391	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4110	Phase 3
0.7388	Intermediate Similarity	NPD2653	Approved
0.7388	Intermediate Similarity	NPD2492	Phase 1
0.7385	Intermediate Similarity	NPD3018	Phase 2
0.7381	Intermediate Similarity	NPD3847	Discontinued
0.7373	Intermediate Similarity	NPD290	Approved
0.7357	Intermediate Similarity	NPD4357	Discontinued
0.7353	Intermediate Similarity	NPD2935	Discontinued
0.7348	Intermediate Similarity	NPD3145	Approved
0.7348	Intermediate Similarity	NPD3144	Approved
0.7323	Intermediate Similarity	NPD1281	Approved
0.7313	Intermediate Similarity	NPD1933	Approved
0.7299	Intermediate Similarity	NPD7266	Discontinued
0.7293	Intermediate Similarity	NPD2674	Phase 3
0.7258	Intermediate Similarity	NPD9493	Approved
0.725	Intermediate Similarity	NPD3021	Approved
0.725	Intermediate Similarity	NPD3022	Approved
0.7231	Intermediate Similarity	NPD987	Approved
0.7222	Intermediate Similarity	NPD5585	Approved
0.7218	Intermediate Similarity	NPD411	Approved
0.7203	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1535	Discovery
0.7185	Intermediate Similarity	NPD4340	Discontinued
0.7154	Intermediate Similarity	NPD2922	Phase 1
0.7153	Intermediate Similarity	NPD3686	Approved
0.7153	Intermediate Similarity	NPD3687	Approved
0.7143	Intermediate Similarity	NPD968	Approved
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD1894	Discontinued
0.7143	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6653	Approved
0.7132	Intermediate Similarity	NPD1608	Approved
0.7132	Intermediate Similarity	NPD1481	Phase 2
0.713	Intermediate Similarity	NPD111	Approved
0.7121	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3620	Phase 2
0.7111	Intermediate Similarity	NPD1613	Approved
0.7111	Intermediate Similarity	NPD1558	Phase 1
0.7107	Intermediate Similarity	NPD556	Approved
0.7099	Intermediate Similarity	NPD1203	Approved
0.709	Intermediate Similarity	NPD5110	Phase 2
0.709	Intermediate Similarity	NPD5109	Approved
0.709	Intermediate Similarity	NPD6798	Discontinued
0.709	Intermediate Similarity	NPD5111	Phase 2
0.7087	Intermediate Similarity	NPD9268	Approved
0.7087	Intermediate Similarity	NPD1651	Approved
0.7077	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD821	Approved
0.7068	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6355	Discontinued
0.7054	Intermediate Similarity	NPD9365	Approved
0.7054	Intermediate Similarity	NPD1611	Approved
0.705	Intermediate Similarity	NPD1375	Discontinued
0.704	Intermediate Similarity	NPD709	Approved
0.704	Intermediate Similarity	NPD6671	Approved
0.7037	Intermediate Similarity	NPD6233	Phase 2
0.7037	Intermediate Similarity	NPD4062	Phase 3
0.7037	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD17	Approved
0.7027	Intermediate Similarity	NPD9295	Approved
0.7023	Intermediate Similarity	NPD3225	Approved
0.7021	Intermediate Similarity	NPD8166	Discontinued
0.7007	Intermediate Similarity	NPD6873	Phase 2
0.7007	Intermediate Similarity	NPD6385	Approved
0.7007	Intermediate Similarity	NPD6386	Approved
0.7	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9269	Phase 2
0.6993	Remote Similarity	NPD5297	Approved
0.6986	Remote Similarity	NPD824	Approved
0.6986	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4140	Approved
0.698	Remote Similarity	NPD3817	Phase 2
0.6974	Remote Similarity	NPD2821	Approved
0.6972	Remote Similarity	NPD6190	Approved
0.6972	Remote Similarity	NPD2219	Phase 1
0.697	Remote Similarity	NPD2797	Approved
0.6967	Remote Similarity	NPD5451	Approved
0.6963	Remote Similarity	NPD5718	Phase 2
0.6963	Remote Similarity	NPD1048	Approved
0.696	Remote Similarity	NPD690	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3060	Approved
0.6947	Remote Similarity	NPD4359	Approved
0.6944	Remote Similarity	NPD4739	Approved
0.6944	Remote Similarity	NPD3146	Approved
0.6944	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7028	Phase 2
0.6934	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD776	Approved
0.6917	Remote Similarity	NPD1019	Discontinued
0.6917	Remote Similarity	NPD258	Approved
0.6917	Remote Similarity	NPD257	Approved
0.6917	Remote Similarity	NPD5647	Approved
0.6912	Remote Similarity	NPD259	Phase 1
0.6906	Remote Similarity	NPD2799	Discontinued
0.6894	Remote Similarity	NPD196	Phase 1
0.6894	Remote Similarity	NPD1876	Approved
0.6889	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1182	Approved
0.6871	Remote Similarity	NPD3111	Phase 1
0.6871	Remote Similarity	NPD3455	Phase 2
0.687	Remote Similarity	NPD2933	Approved
0.687	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2934	Approved
0.687	Remote Similarity	NPD3972	Approved
0.6864	Remote Similarity	NPD1242	Phase 1
0.6863	Remote Similarity	NPD8127	Discontinued
0.6861	Remote Similarity	NPD2979	Phase 3
0.6861	Remote Similarity	NPD825	Approved
0.6861	Remote Similarity	NPD826	Approved
0.6857	Remote Similarity	NPD6032	Approved
0.6857	Remote Similarity	NPD2438	Suspended
0.6857	Remote Similarity	NPD2161	Phase 2
0.6846	Remote Similarity	NPD1934	Approved
0.6846	Remote Similarity	NPD37	Approved
0.6838	Remote Similarity	NPD3268	Approved
0.6838	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7097	Phase 1
0.6835	Remote Similarity	NPD6895	Approved
0.6835	Remote Similarity	NPD6896	Approved
0.6831	Remote Similarity	NPD4237	Approved
0.6831	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4236	Phase 3
0.6831	Remote Similarity	NPD4162	Approved
0.6831	Remote Similarity	NPD1652	Phase 2
0.6821	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3882	Suspended
0.6818	Remote Similarity	NPD6232	Discontinued
0.6818	Remote Similarity	NPD1669	Approved
0.6815	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2614	Approved
0.6815	Remote Similarity	NPD6832	Phase 2
0.6812	Remote Similarity	NPD3657	Discovery
0.6812	Remote Similarity	NPD555	Phase 2
0.681	Remote Similarity	NPD844	Approved
0.681	Remote Similarity	NPD2859	Approved
0.681	Remote Similarity	NPD2860	Approved
0.6809	Remote Similarity	NPD5763	Approved
0.6809	Remote Similarity	NPD3656	Approved
0.6809	Remote Similarity	NPD3540	Phase 1
0.6809	Remote Similarity	NPD5762	Approved
0.68	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.68	Remote Similarity	NPD9379	Approved
0.68	Remote Similarity	NPD1138	Approved
0.68	Remote Similarity	NPD9377	Approved
0.68	Remote Similarity	NPD2801	Approved
0.6794	Remote Similarity	NPD1091	Approved
0.6791	Remote Similarity	NPD6584	Phase 3
0.6791	Remote Similarity	NPD2798	Approved
0.6788	Remote Similarity	NPD5745	Approved
0.6786	Remote Similarity	NPD4308	Phase 3
0.6783	Remote Similarity	NPD7003	Approved
0.6781	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3020	Approved
0.6779	Remote Similarity	NPD5089	Approved
0.6779	Remote Similarity	NPD5090	Approved
0.6774	Remote Similarity	NPD9280	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