NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	184.07
Volume:	182.915
LogP:	2.104
LogD:	1.519
LogS:	-1.884
# Rotatable Bonds:	3
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.753
Synthetic Accessibility Score:	2.928
Fsp3:	0.444
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:	-5.239
MDCK Permeability:	1.4711788935528602e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	93.62609100341797%
Volume Distribution (VD):	0.455
Pgp-substrate:	8.861526489257812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.318
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.151
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.053

ADMET: Excretion

Clearance (CL):	3.369
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.788
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.77
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.452
Carcinogencity:	0.476
Eye Corrosion:	0.068
Eye Irritation:	0.689
Respiratory Toxicity:	0.734

Download Data

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

Natural Product: NPC48641

Natural Product ID:	NPC48641
*Common Name:**	(2R,3S)-4-Methylidene-5-Oxo-2-Propyloxolane-3-Carboxylic Acid
IUPAC Name:	(2R,3S)-4-methylidene-5-oxo-2-propyloxolane-3-carboxylic acid
Synonyms:
Standard InCHIKey:	SRQUTZJZABSZRQ-RQJHMYQMSA-N
Standard InCHI:	InChI=1S/C9H12O4/c1-3-4-6-7(8(10)11)5(2)9(12)13-6/h6-7H,2-4H2,1H3,(H,10,11)/t6-,7+/m1/s1
SMILES:	CCC[C@H]1OC(=O)C(=C)[C@@H]1C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL217676
PubChem CID:	21579153
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO16865.1	Prunus serrulata var. spontanea	Varieties	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16865.1	Prunus serrulata var. spontanea	Varieties	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16885	Phonus arborescens	Species	Asteraceae	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
Others	7

Activity Type	# Activity
Cell Line	1
Individual Protein	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	Activity	=	44.0	%	PMID[496359]
NPT1079	Individual Protein	Histone acetyltransferase p300	Homo sapiens	Activity	=	58.6	%	PMID[496361]
NPT1834	Individual Protein	CREB-binding protein	Homo sapiens	Activity	=	45.9	%	PMID[496361]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Activity	=	54.5	%	PMID[496361]
NPT1080	Individual Protein	Histone acetyltransferase PCAF	Homo sapiens	Activity	=	76.8	%	PMID[496361]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	IC50	=	100000.0	nM	PMID[496362]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	IC50	=	100000.0	nM	PMID[496363]
NPT2	Others	Unspecified		Activity	=	55.0	%	PMID[496360]
NPT2	Others	Unspecified		Inhibition	=	44.0	%	PMID[496361]

☑ 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 NPC48641 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	174
0.1-0.2	1661
0.2-0.3	6540
0.3-0.4	16032
0.4-0.5	9670
0.5-0.6	6225
0.6-0.7	1855
0.7-0.8	474
0.8-0.85	62
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9315	High Similarity	NPC19841
0.8481	Intermediate Similarity	NPC158756
0.8375	Intermediate Similarity	NPC470755
0.8333	Intermediate Similarity	NPC24417
0.8312	Intermediate Similarity	NPC167881
0.8312	Intermediate Similarity	NPC98557
0.8272	Intermediate Similarity	NPC469910
0.8228	Intermediate Similarity	NPC229825
0.8182	Intermediate Similarity	NPC108816
0.8182	Intermediate Similarity	NPC93763
0.8125	Intermediate Similarity	NPC40746
0.8125	Intermediate Similarity	NPC169575
0.8125	Intermediate Similarity	NPC59097
0.8125	Intermediate Similarity	NPC131669
0.8125	Intermediate Similarity	NPC473390
0.8072	Intermediate Similarity	NPC476803
0.8072	Intermediate Similarity	NPC475819
0.8072	Intermediate Similarity	NPC476805
0.8052	Intermediate Similarity	NPC141789
0.8052	Intermediate Similarity	NPC7563
0.8052	Intermediate Similarity	NPC320630
0.8052	Intermediate Similarity	NPC116177
0.8052	Intermediate Similarity	NPC476028
0.8052	Intermediate Similarity	NPC171204
0.8052	Intermediate Similarity	NPC97516
0.8025	Intermediate Similarity	NPC114979
0.8025	Intermediate Similarity	NPC96259
0.8025	Intermediate Similarity	NPC141193
0.8025	Intermediate Similarity	NPC191476
0.8025	Intermediate Similarity	NPC476804
0.7976	Intermediate Similarity	NPC12872
0.7976	Intermediate Similarity	NPC168679
0.7971	Intermediate Similarity	NPC472328
0.7952	Intermediate Similarity	NPC201658
0.7949	Intermediate Similarity	NPC471465
0.7949	Intermediate Similarity	NPC267231
0.7949	Intermediate Similarity	NPC196653
0.7927	Intermediate Similarity	NPC255307
0.7927	Intermediate Similarity	NPC165162
0.7895	Intermediate Similarity	NPC476355
0.7895	Intermediate Similarity	NPC140287
0.7882	Intermediate Similarity	NPC19087
0.7882	Intermediate Similarity	NPC474232
0.7875	Intermediate Similarity	NPC52861
0.7867	Intermediate Similarity	NPC474590
0.7867	Intermediate Similarity	NPC163003
0.7848	Intermediate Similarity	NPC470239
0.7848	Intermediate Similarity	NPC270126
0.7848	Intermediate Similarity	NPC470244
0.7831	Intermediate Similarity	NPC475461
0.7831	Intermediate Similarity	NPC469483
0.7831	Intermediate Similarity	NPC150755
0.7831	Intermediate Similarity	NPC236692
0.7831	Intermediate Similarity	NPC305475
0.7831	Intermediate Similarity	NPC309757
0.7831	Intermediate Similarity	NPC162071
0.7791	Intermediate Similarity	NPC184063
0.7778	Intermediate Similarity	NPC89555
0.7765	Intermediate Similarity	NPC38392
0.7763	Intermediate Similarity	NPC58956
0.7763	Intermediate Similarity	NPC269206
0.7763	Intermediate Similarity	NPC295633
0.775	Intermediate Similarity	NPC281132
0.775	Intermediate Similarity	NPC223904
0.7701	Intermediate Similarity	NPC469692
0.7701	Intermediate Similarity	NPC469645
0.7701	Intermediate Similarity	NPC475302
0.7692	Intermediate Similarity	NPC68819
0.7692	Intermediate Similarity	NPC123360
0.7683	Intermediate Similarity	NPC245665
0.7654	Intermediate Similarity	NPC281949
0.7654	Intermediate Similarity	NPC301477
0.7654	Intermediate Similarity	NPC25684
0.7654	Intermediate Similarity	NPC141810
0.7647	Intermediate Similarity	NPC207114
0.7647	Intermediate Similarity	NPC477302
0.7647	Intermediate Similarity	NPC136879
0.7647	Intermediate Similarity	NPC217983
0.7647	Intermediate Similarity	NPC473715
0.7647	Intermediate Similarity	NPC79549
0.7639	Intermediate Similarity	NPC470325
0.7639	Intermediate Similarity	NPC53642
0.7625	Intermediate Similarity	NPC617
0.7625	Intermediate Similarity	NPC178277
0.7619	Intermediate Similarity	NPC470242
0.7619	Intermediate Similarity	NPC187661
0.7619	Intermediate Similarity	NPC261721
0.7619	Intermediate Similarity	NPC238593
0.7619	Intermediate Similarity	NPC304558
0.7614	Intermediate Similarity	NPC121825
0.7595	Intermediate Similarity	NPC476794
0.7595	Intermediate Similarity	NPC474760
0.7595	Intermediate Similarity	NPC470240
0.7595	Intermediate Similarity	NPC122847
0.759	Intermediate Similarity	NPC156485
0.7586	Intermediate Similarity	NPC261607
0.7586	Intermediate Similarity	NPC111114
0.7586	Intermediate Similarity	NPC300312
0.7564	Intermediate Similarity	NPC193351
0.7564	Intermediate Similarity	NPC138408
0.7564	Intermediate Similarity	NPC155587
0.7564	Intermediate Similarity	NPC226669
0.7558	Intermediate Similarity	NPC206001
0.7558	Intermediate Similarity	NPC155935
0.7558	Intermediate Similarity	NPC215556
0.7558	Intermediate Similarity	NPC218927
0.7531	Intermediate Similarity	NPC6823
0.7529	Intermediate Similarity	NPC266957
0.7529	Intermediate Similarity	NPC118601
0.7529	Intermediate Similarity	NPC186148
0.7529	Intermediate Similarity	NPC190753
0.7528	Intermediate Similarity	NPC193645
0.7528	Intermediate Similarity	NPC471142
0.7528	Intermediate Similarity	NPC90121
0.7528	Intermediate Similarity	NPC475659
0.7528	Intermediate Similarity	NPC477922
0.7528	Intermediate Similarity	NPC275960
0.7528	Intermediate Similarity	NPC475900
0.7528	Intermediate Similarity	NPC48803
0.75	Intermediate Similarity	NPC21469
0.75	Intermediate Similarity	NPC473263
0.75	Intermediate Similarity	NPC153590
0.75	Intermediate Similarity	NPC473273
0.75	Intermediate Similarity	NPC60386
0.75	Intermediate Similarity	NPC308656
0.75	Intermediate Similarity	NPC473234
0.7471	Intermediate Similarity	NPC297474
0.7471	Intermediate Similarity	NPC206614
0.7471	Intermediate Similarity	NPC71533
0.7471	Intermediate Similarity	NPC106510
0.7471	Intermediate Similarity	NPC473619
0.7471	Intermediate Similarity	NPC144133
0.7471	Intermediate Similarity	NPC129419
0.7471	Intermediate Similarity	NPC469368
0.7471	Intermediate Similarity	NPC474323
0.7471	Intermediate Similarity	NPC35809
0.7471	Intermediate Similarity	NPC179394
0.7471	Intermediate Similarity	NPC216284
0.7471	Intermediate Similarity	NPC475855
0.7471	Intermediate Similarity	NPC54065
0.747	Intermediate Similarity	NPC318468
0.747	Intermediate Similarity	NPC475947
0.747	Intermediate Similarity	NPC128429
0.747	Intermediate Similarity	NPC116543
0.747	Intermediate Similarity	NPC250315
0.7468	Intermediate Similarity	NPC235906
0.7444	Intermediate Similarity	NPC158416
0.7444	Intermediate Similarity	NPC91771
0.7444	Intermediate Similarity	NPC230800
0.7444	Intermediate Similarity	NPC76862
0.7444	Intermediate Similarity	NPC477921
0.7444	Intermediate Similarity	NPC39859
0.7444	Intermediate Similarity	NPC142529
0.7444	Intermediate Similarity	NPC476009
0.7444	Intermediate Similarity	NPC473859
0.7444	Intermediate Similarity	NPC470883
0.7442	Intermediate Similarity	NPC58219
0.7442	Intermediate Similarity	NPC177629
0.7442	Intermediate Similarity	NPC202672
0.7442	Intermediate Similarity	NPC178875
0.7439	Intermediate Similarity	NPC471325
0.7436	Intermediate Similarity	NPC114727
0.7436	Intermediate Similarity	NPC476590
0.7436	Intermediate Similarity	NPC320537
0.7436	Intermediate Similarity	NPC143979
0.7416	Intermediate Similarity	NPC473331
0.7416	Intermediate Similarity	NPC167219
0.7412	Intermediate Similarity	NPC9231
0.7412	Intermediate Similarity	NPC85698
0.7386	Intermediate Similarity	NPC35959
0.7386	Intermediate Similarity	NPC473321
0.7386	Intermediate Similarity	NPC57304
0.7386	Intermediate Similarity	NPC171360
0.7386	Intermediate Similarity	NPC293001
0.7386	Intermediate Similarity	NPC63193
0.7386	Intermediate Similarity	NPC184463
0.7386	Intermediate Similarity	NPC475881
0.7386	Intermediate Similarity	NPC155215
0.7386	Intermediate Similarity	NPC70251
0.7386	Intermediate Similarity	NPC131209
0.7386	Intermediate Similarity	NPC133888
0.7386	Intermediate Similarity	NPC29821
0.7386	Intermediate Similarity	NPC133698
0.7381	Intermediate Similarity	NPC138647
0.7381	Intermediate Similarity	NPC194859
0.7381	Intermediate Similarity	NPC224386
0.7381	Intermediate Similarity	NPC470238
0.7381	Intermediate Similarity	NPC159635
0.7381	Intermediate Similarity	NPC115786
0.7375	Intermediate Similarity	NPC65603
0.7375	Intermediate Similarity	NPC41780
0.7375	Intermediate Similarity	NPC187568
0.7375	Intermediate Similarity	NPC57744
0.7363	Intermediate Similarity	NPC169205
0.7363	Intermediate Similarity	NPC471462
0.7363	Intermediate Similarity	NPC311904
0.7363	Intermediate Similarity	NPC474313
0.7356	Intermediate Similarity	NPC307411
0.7356	Intermediate Similarity	NPC92974
0.7356	Intermediate Similarity	NPC268298

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 NPC48641 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	2394
0.2-0.3	3792
0.3-0.4	1879
0.4-0.5	650
0.5-0.6	189
0.6-0.7	37
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7528	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5785	Approved
0.6778	Remote Similarity	NPD1695	Approved
0.6768	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5363	Approved
0.6703	Remote Similarity	NPD46	Approved
0.6703	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6629	Remote Similarity	NPD5786	Approved
0.6628	Remote Similarity	NPD5369	Approved
0.6562	Remote Similarity	NPD4225	Approved
0.6552	Remote Similarity	NPD4269	Approved
0.6552	Remote Similarity	NPD4270	Approved
0.6512	Remote Similarity	NPD4252	Approved
0.6512	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7983	Approved
0.641	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6371	Approved
0.6364	Remote Similarity	NPD5209	Approved
0.6364	Remote Similarity	NPD6435	Approved
0.6333	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1694	Approved
0.6316	Remote Similarity	NPD5282	Discontinued
0.6292	Remote Similarity	NPD5362	Discontinued
0.6279	Remote Similarity	NPD4268	Approved
0.6279	Remote Similarity	NPD4271	Approved
0.6264	Remote Similarity	NPD4249	Approved
0.6237	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6101	Approved
0.6211	Remote Similarity	NPD5778	Approved
0.6211	Remote Similarity	NPD6399	Phase 3
0.6211	Remote Similarity	NPD5779	Approved
0.6196	Remote Similarity	NPD4250	Approved
0.6196	Remote Similarity	NPD4251	Approved
0.618	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD229	Approved
0.617	Remote Similarity	NPD7838	Discovery
0.6164	Remote Similarity	NPD9298	Approved
0.6136	Remote Similarity	NPD5368	Approved
0.6136	Remote Similarity	NPD4820	Approved
0.6136	Remote Similarity	NPD4819	Approved
0.6136	Remote Similarity	NPD4822	Approved
0.6136	Remote Similarity	NPD4821	Approved
0.6105	Remote Similarity	NPD8034	Phase 2
0.6105	Remote Similarity	NPD8035	Phase 2
0.6105	Remote Similarity	NPD6411	Approved
0.6064	Remote Similarity	NPD5370	Suspended
0.6061	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7839	Suspended
0.5938	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7115	Discovery
0.5909	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6686	Approved
0.5888	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.58	Remote Similarity	NPD7902	Approved
0.5795	Remote Similarity	NPD4756	Discovery
0.5773	Remote Similarity	NPD7637	Suspended
0.5761	Remote Similarity	NPD5332	Approved
0.5761	Remote Similarity	NPD5331	Approved
0.5747	Remote Similarity	NPD8039	Approved
0.5745	Remote Similarity	NPD6422	Discontinued
0.5714	Remote Similarity	NPD4790	Discontinued
0.5702	Remote Similarity	NPD8513	Phase 3
0.5702	Remote Similarity	NPD8517	Approved
0.5702	Remote Similarity	NPD8515	Approved
0.5702	Remote Similarity	NPD8516	Approved
0.5699	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD6053	Discontinued
0.5648	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.56	Remote Similarity	NPD5695	Phase 3

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