NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.17
Volume:	307.22
LogP:	4.668
LogD:	3.124
LogS:	-4.732
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.8
Synthetic Accessibility Score:	2.352
Fsp3:	0.471
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.854
MDCK Permeability:	2.3510201572207734e-05
Pgp-inhibitor:	0.395
Pgp-substrate:	0.045
Human Intestinal Absorption (HIA):	0.119
20% Bioavailability (F20%):	0.291
30% Bioavailability (F30%):	0.395

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.154
Plasma Protein Binding (PPB):	99.45120239257812%
Volume Distribution (VD):	0.327
Pgp-substrate:	3.6840453147888184%

ADMET: Metabolism

CYP1A2-inhibitor:	0.224
CYP1A2-substrate:	0.831
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.122
CYP2C9-inhibitor:	0.414
CYP2C9-substrate:	0.469
CYP2D6-inhibitor:	0.693
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	0.996
Half-life (T1/2):	0.748

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.723
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.403
Skin Sensitization:	0.945
Carcinogencity:	0.044
Eye Corrosion:	0.238
Eye Irritation:	0.898
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC470039

Natural Product ID:	NPC470039
*Common Name:**	3-(3,5-Di-Tert-Butylphenyl-4-Hydroxy)Acrylic Acid
IUPAC Name:	(E)-3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-2-enoic acid
Synonyms:
Standard InCHIKey:	CTYWXRDQWMRIIM-BQYQJAHWSA-N
Standard InCHI:	InChI=1S/C17H24O3/c1-16(2,3)12-9-11(7-8-14(18)19)10-13(15(12)20)17(4,5)6/h7-10,20H,1-6H3,(H,18,19)/b8-7+
SMILES:	CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C=CC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651776
PubChem CID:	689095
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0002503] Hydroxycinnamic 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
NPO32851	brazilian green propolis	Species	n.a.	n.a.	n.a.	Brazilian green propolis	n.a.	PMID[21865046]

☑ 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	1
Others	15

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	5
Organism	1
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	108.4	%	PMID[484929]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	2.0	%	PMID[484928]
NPT2	Others	Unspecified		IC50	=	220000.0	nM	PMID[484928]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	97.8	%	PMID[484928]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[484928]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	35.7	%	PMID[484928]
NPT35	Others	n.a.		Activity	=	28.1	%	PMID[484928]
NPT35	Others	n.a.		Activity	=	26.9	%	PMID[484928]
NPT35	Others	n.a.		Activity	=	31.6	%	PMID[484928]
NPT35	Others	n.a.		Activity	=	36.9	%	PMID[484928]
NPT35	Others	n.a.		Activity	=	47.7	%	PMID[484928]
NPT35	Others	n.a.		Activity	=	26.5	%	PMID[484928]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	54.1	%	PMID[484928]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	53.9	%	PMID[484928]
NPT35	Others	n.a.		Activity	=	74.8	%	PMID[484928]
NPT2	Others	Unspecified		Ratio	=	0.77	n.a.	PMID[484929]

☑ 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 NPC470039 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	218
0.1-0.2	1440
0.2-0.3	3447
0.3-0.4	10826
0.4-0.5	9122
0.5-0.6	10120
0.6-0.7	6295
0.7-0.8	1101
0.8-0.85	104
0.85-0.9	17
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.97	High Similarity	NPC243677
0.9505	High Similarity	NPC303141
0.9307	High Similarity	NPC470202
0.9143	High Similarity	NPC75272
0.9143	High Similarity	NPC471954
0.8922	High Similarity	NPC225506
0.89	High Similarity	NPC144682
0.8824	High Similarity	NPC252821
0.8824	High Similarity	NPC122005
0.88	High Similarity	NPC289769
0.8713	High Similarity	NPC246679
0.8624	High Similarity	NPC139946
0.8614	High Similarity	NPC32977
0.8614	High Similarity	NPC81010
0.8585	High Similarity	NPC99557
0.8585	High Similarity	NPC219286
0.8584	High Similarity	NPC474890
0.8584	High Similarity	NPC161943
0.8584	High Similarity	NPC273282
0.8571	High Similarity	NPC83718
0.8545	High Similarity	NPC199462
0.8545	High Similarity	NPC228988
0.8544	High Similarity	NPC77492
0.8529	High Similarity	NPC8392
0.8476	Intermediate Similarity	NPC472585
0.8462	Intermediate Similarity	NPC128723
0.8462	Intermediate Similarity	NPC174991
0.8431	Intermediate Similarity	NPC152415
0.8431	Intermediate Similarity	NPC316301
0.8431	Intermediate Similarity	NPC27323
0.8426	Intermediate Similarity	NPC228737
0.8416	Intermediate Similarity	NPC204210
0.8416	Intermediate Similarity	NPC306074
0.8411	Intermediate Similarity	NPC138942
0.84	Intermediate Similarity	NPC70436
0.8396	Intermediate Similarity	NPC168829
0.8393	Intermediate Similarity	NPC114918
0.8381	Intermediate Similarity	NPC253746
0.8364	Intermediate Similarity	NPC473809
0.8362	Intermediate Similarity	NPC164852
0.8362	Intermediate Similarity	NPC241001
0.8333	Intermediate Similarity	NPC263754
0.8333	Intermediate Similarity	NPC122117
0.8333	Intermediate Similarity	NPC181709
0.8333	Intermediate Similarity	NPC174087
0.8333	Intermediate Similarity	NPC183154
0.8318	Intermediate Similarity	NPC288411
0.8304	Intermediate Similarity	NPC242136
0.8288	Intermediate Similarity	NPC228609
0.8286	Intermediate Similarity	NPC92730
0.8264	Intermediate Similarity	NPC229894
0.8264	Intermediate Similarity	NPC193203
0.8246	Intermediate Similarity	NPC471936
0.8235	Intermediate Similarity	NPC265413
0.8235	Intermediate Similarity	NPC10154
0.8235	Intermediate Similarity	NPC155908
0.8235	Intermediate Similarity	NPC270547
0.8224	Intermediate Similarity	NPC135784
0.8224	Intermediate Similarity	NPC304638
0.8224	Intermediate Similarity	NPC269212
0.822	Intermediate Similarity	NPC121168
0.8218	Intermediate Similarity	NPC242240
0.8218	Intermediate Similarity	NPC177420
0.8218	Intermediate Similarity	NPC318325
0.8218	Intermediate Similarity	NPC280347
0.8218	Intermediate Similarity	NPC98772
0.8218	Intermediate Similarity	NPC123273
0.8214	Intermediate Similarity	NPC228425
0.8208	Intermediate Similarity	NPC211885
0.8198	Intermediate Similarity	NPC183700
0.8198	Intermediate Similarity	NPC13482
0.8198	Intermediate Similarity	NPC222905
0.8197	Intermediate Similarity	NPC117899
0.819	Intermediate Similarity	NPC201967
0.819	Intermediate Similarity	NPC225464
0.8182	Intermediate Similarity	NPC279887
0.8182	Intermediate Similarity	NPC68260
0.8173	Intermediate Similarity	NPC26244
0.8173	Intermediate Similarity	NPC222146
0.8173	Intermediate Similarity	NPC257182
0.8165	Intermediate Similarity	NPC271274
0.8148	Intermediate Similarity	NPC93831
0.8142	Intermediate Similarity	NPC211421
0.8137	Intermediate Similarity	NPC55561
0.8136	Intermediate Similarity	NPC249340
0.8136	Intermediate Similarity	NPC162935
0.8131	Intermediate Similarity	NPC51015
0.8131	Intermediate Similarity	NPC252105
0.8119	Intermediate Similarity	NPC113460
0.8119	Intermediate Similarity	NPC25493
0.8113	Intermediate Similarity	NPC245561
0.8113	Intermediate Similarity	NPC33675
0.8113	Intermediate Similarity	NPC299762
0.8113	Intermediate Similarity	NPC130193
0.8108	Intermediate Similarity	NPC282855
0.8108	Intermediate Similarity	NPC26013
0.8095	Intermediate Similarity	NPC283711
0.8095	Intermediate Similarity	NPC473388
0.8091	Intermediate Similarity	NPC260952
0.8083	Intermediate Similarity	NPC474532
0.8077	Intermediate Similarity	NPC128062
0.8077	Intermediate Similarity	NPC151715
0.8073	Intermediate Similarity	NPC47284
0.807	Intermediate Similarity	NPC41851
0.807	Intermediate Similarity	NPC197513
0.8067	Intermediate Similarity	NPC475192
0.8067	Intermediate Similarity	NPC67300
0.8065	Intermediate Similarity	NPC18798
0.8058	Intermediate Similarity	NPC304541
0.8056	Intermediate Similarity	NPC108497
0.8053	Intermediate Similarity	NPC250323
0.8053	Intermediate Similarity	NPC286222
0.8051	Intermediate Similarity	NPC131868
0.8039	Intermediate Similarity	NPC258219
0.8037	Intermediate Similarity	NPC52472
0.8036	Intermediate Similarity	NPC141782
0.8036	Intermediate Similarity	NPC63345
0.8036	Intermediate Similarity	NPC208229
0.8036	Intermediate Similarity	NPC296683
0.8034	Intermediate Similarity	NPC42657
0.802	Intermediate Similarity	NPC307235
0.802	Intermediate Similarity	NPC184169
0.802	Intermediate Similarity	NPC23167
0.802	Intermediate Similarity	NPC407
0.8019	Intermediate Similarity	NPC140619
0.8018	Intermediate Similarity	NPC61885
0.8018	Intermediate Similarity	NPC206341
0.8018	Intermediate Similarity	NPC31274
0.8018	Intermediate Similarity	NPC63698
0.8018	Intermediate Similarity	NPC262365
0.8017	Intermediate Similarity	NPC137416
0.8017	Intermediate Similarity	NPC278652
0.8	Intermediate Similarity	NPC53740
0.8	Intermediate Similarity	NPC286006
0.8	Intermediate Similarity	NPC477814
0.8	Intermediate Similarity	NPC29989
0.8	Intermediate Similarity	NPC69332
0.8	Intermediate Similarity	NPC95178
0.7983	Intermediate Similarity	NPC154696
0.7983	Intermediate Similarity	NPC251259
0.7981	Intermediate Similarity	NPC55903
0.7966	Intermediate Similarity	NPC478121
0.7965	Intermediate Similarity	NPC176279
0.7965	Intermediate Similarity	NPC470355
0.7965	Intermediate Similarity	NPC95716
0.7965	Intermediate Similarity	NPC260323
0.7963	Intermediate Similarity	NPC94343
0.7951	Intermediate Similarity	NPC473751
0.7946	Intermediate Similarity	NPC95172
0.7946	Intermediate Similarity	NPC79543
0.7946	Intermediate Similarity	NPC98392
0.7946	Intermediate Similarity	NPC88141
0.7944	Intermediate Similarity	NPC171843
0.7934	Intermediate Similarity	NPC184219
0.7928	Intermediate Similarity	NPC151477
0.7928	Intermediate Similarity	NPC320439
0.7925	Intermediate Similarity	NPC292730
0.7925	Intermediate Similarity	NPC82664
0.7925	Intermediate Similarity	NPC216520
0.7925	Intermediate Similarity	NPC132271
0.7921	Intermediate Similarity	NPC155393
0.7921	Intermediate Similarity	NPC197783
0.7917	Intermediate Similarity	NPC478058
0.7913	Intermediate Similarity	NPC195922
0.7913	Intermediate Similarity	NPC268160
0.7909	Intermediate Similarity	NPC227255
0.7909	Intermediate Similarity	NPC127676
0.7903	Intermediate Similarity	NPC86257
0.7903	Intermediate Similarity	NPC288290
0.7899	Intermediate Similarity	NPC32322
0.7899	Intermediate Similarity	NPC259703
0.7895	Intermediate Similarity	NPC46940
0.789	Intermediate Similarity	NPC13426
0.789	Intermediate Similarity	NPC68269
0.7886	Intermediate Similarity	NPC243688
0.7885	Intermediate Similarity	NPC45040
0.7881	Intermediate Similarity	NPC473767
0.7876	Intermediate Similarity	NPC44732
0.7874	Intermediate Similarity	NPC477594
0.787	Intermediate Similarity	NPC248396
0.787	Intermediate Similarity	NPC48730
0.787	Intermediate Similarity	NPC72729
0.787	Intermediate Similarity	NPC129373
0.7863	Intermediate Similarity	NPC160199
0.7863	Intermediate Similarity	NPC477136
0.7851	Intermediate Similarity	NPC275145
0.785	Intermediate Similarity	NPC79241
0.785	Intermediate Similarity	NPC6597
0.785	Intermediate Similarity	NPC260000
0.785	Intermediate Similarity	NPC152097
0.7845	Intermediate Similarity	NPC35797
0.7845	Intermediate Similarity	NPC192948
0.7845	Intermediate Similarity	NPC147179
0.7838	Intermediate Similarity	NPC310456
0.7838	Intermediate Similarity	NPC155072
0.7838	Intermediate Similarity	NPC54765
0.7838	Intermediate Similarity	NPC294902
0.7838	Intermediate Similarity	NPC70843
0.7838	Intermediate Similarity	NPC1075
0.7838	Intermediate Similarity	NPC1786

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 NPC470039 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	987
0.2-0.3	1297
0.3-0.4	2773
0.4-0.5	2180
0.5-0.6	1178
0.6-0.7	448
0.7-0.8	64
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.89	High Similarity	NPD1809	Phase 2
0.8515	High Similarity	NPD845	Approved
0.8431	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8348	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8173	Intermediate Similarity	NPD2859	Approved
0.8173	Intermediate Similarity	NPD2860	Approved
0.8125	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD4626	Approved
0.8113	Intermediate Similarity	NPD3020	Approved
0.8077	Intermediate Similarity	NPD2934	Approved
0.8077	Intermediate Similarity	NPD2933	Approved
0.8037	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD940	Approved
0.7963	Intermediate Similarity	NPD846	Approved
0.783	Intermediate Similarity	NPD844	Approved
0.7757	Intermediate Similarity	NPD288	Approved
0.7742	Intermediate Similarity	NPD4208	Discontinued
0.7742	Intermediate Similarity	NPD4212	Discontinued
0.7731	Intermediate Similarity	NPD5691	Approved
0.7724	Intermediate Similarity	NPD1164	Approved
0.7723	Intermediate Similarity	NPD111	Approved
0.7723	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD4207	Discontinued
0.7611	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7635	Approved
0.7583	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD9266	Approved
0.7544	Intermediate Similarity	NPD74	Approved
0.7522	Intermediate Similarity	NPD3134	Approved
0.7521	Intermediate Similarity	NPD3019	Approved
0.7521	Intermediate Similarity	NPD2932	Approved
0.7521	Intermediate Similarity	NPD4589	Approved
0.7479	Intermediate Similarity	NPD9493	Approved
0.7478	Intermediate Similarity	NPD3022	Approved
0.7478	Intermediate Similarity	NPD3021	Approved
0.746	Intermediate Similarity	NPD5736	Approved
0.7459	Intermediate Similarity	NPD3143	Discontinued
0.7458	Intermediate Similarity	NPD5951	Approved
0.7456	Intermediate Similarity	NPD9263	Approved
0.7456	Intermediate Similarity	NPD9264	Approved
0.7456	Intermediate Similarity	NPD2342	Discontinued
0.7456	Intermediate Similarity	NPD9267	Approved
0.7398	Intermediate Similarity	NPD422	Phase 1
0.7395	Intermediate Similarity	NPD256	Approved
0.7395	Intermediate Similarity	NPD255	Approved
0.7355	Intermediate Similarity	NPD3091	Approved
0.7355	Intermediate Similarity	NPD7330	Discontinued
0.7355	Intermediate Similarity	NPD5304	Approved
0.7355	Intermediate Similarity	NPD5303	Approved
0.7355	Intermediate Similarity	NPD9545	Approved
0.7339	Intermediate Similarity	NPD3070	Discontinued
0.7333	Intermediate Similarity	NPD7003	Approved
0.7328	Intermediate Similarity	NPD4750	Phase 3
0.7317	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3496	Discontinued
0.7308	Intermediate Similarity	NPD4060	Phase 1
0.7304	Intermediate Similarity	NPD1358	Approved
0.7302	Intermediate Similarity	NPD2797	Approved
0.7293	Intermediate Similarity	NPD5408	Approved
0.7293	Intermediate Similarity	NPD5404	Approved
0.7293	Intermediate Similarity	NPD5406	Approved
0.7293	Intermediate Similarity	NPD2935	Discontinued
0.7293	Intermediate Similarity	NPD5405	Approved
0.7236	Intermediate Similarity	NPD4059	Approved
0.7231	Intermediate Similarity	NPD6663	Approved
0.7231	Intermediate Similarity	NPD4248	Discontinued
0.7227	Intermediate Similarity	NPD2229	Approved
0.7227	Intermediate Similarity	NPD2228	Approved
0.7227	Intermediate Similarity	NPD2234	Approved
0.7218	Intermediate Similarity	NPD2799	Discontinued
0.719	Intermediate Similarity	NPD7636	Approved
0.7143	Intermediate Similarity	NPD2066	Phase 3
0.7143	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD9697	Approved
0.712	Intermediate Similarity	NPD3092	Approved
0.7105	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1929	Approved
0.7105	Intermediate Similarity	NPD1930	Approved
0.7105	Intermediate Similarity	NPD9261	Approved
0.7097	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6049	Phase 2
0.708	Intermediate Similarity	NPD8166	Discontinued
0.708	Intermediate Similarity	NPD3028	Approved
0.7073	Intermediate Similarity	NPD1759	Phase 1
0.7069	Intermediate Similarity	NPD1445	Approved
0.7069	Intermediate Similarity	NPD1444	Approved
0.7064	Intermediate Similarity	NPD1088	Approved
0.7049	Intermediate Similarity	NPD9568	Approved
0.7049	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD9608	Approved
0.7043	Intermediate Similarity	NPD9610	Approved
0.704	Intermediate Similarity	NPD3847	Discontinued
0.7037	Intermediate Similarity	NPD9258	Approved
0.7037	Intermediate Similarity	NPD9256	Approved
0.7025	Intermediate Similarity	NPD9281	Approved
0.7023	Intermediate Similarity	NPD3764	Approved
0.7023	Intermediate Similarity	NPD3268	Approved
0.7019	Intermediate Similarity	NPD3971	Phase 1
0.7007	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1138	Approved
0.6992	Remote Similarity	NPD5124	Phase 1
0.6992	Remote Similarity	NPD1758	Phase 1
0.6992	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1201	Approved
0.6967	Remote Similarity	NPD7157	Approved
0.6967	Remote Similarity	NPD6671	Approved
0.696	Remote Similarity	NPD3095	Discontinued
0.696	Remote Similarity	NPD1778	Approved
0.696	Remote Similarity	NPD1751	Approved
0.6957	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6647	Phase 2
0.6953	Remote Similarity	NPD1283	Approved
0.6949	Remote Similarity	NPD2684	Approved
0.6947	Remote Similarity	NPD7095	Approved
0.693	Remote Similarity	NPD1242	Phase 1
0.6929	Remote Similarity	NPD3972	Approved
0.6929	Remote Similarity	NPD9717	Approved
0.6923	Remote Similarity	NPD7458	Discontinued
0.6917	Remote Similarity	NPD4140	Approved
0.6917	Remote Similarity	NPD1139	Approved
0.6917	Remote Similarity	NPD1137	Approved
0.6905	Remote Similarity	NPD3023	Approved
0.6905	Remote Similarity	NPD3026	Approved
0.6903	Remote Similarity	NPD9273	Approved
0.69	Remote Similarity	NPD9716	Approved
0.6899	Remote Similarity	NPD1470	Approved
0.6899	Remote Similarity	NPD3094	Phase 2
0.6897	Remote Similarity	NPD5909	Discontinued
0.6894	Remote Similarity	NPD2313	Discontinued
0.6891	Remote Similarity	NPD1792	Phase 2
0.6885	Remote Similarity	NPD2629	Approved
0.6885	Remote Similarity	NPD1793	Approved
0.6885	Remote Similarity	NPD1791	Approved
0.6881	Remote Similarity	NPD1086	Approved
0.6881	Remote Similarity	NPD1090	Approved
0.6881	Remote Similarity	NPD1089	Approved
0.688	Remote Similarity	NPD4093	Discontinued
0.688	Remote Similarity	NPD3024	Approved
0.688	Remote Similarity	NPD3025	Approved
0.6846	Remote Similarity	NPD2798	Approved
0.6835	Remote Similarity	NPD4628	Phase 3
0.6829	Remote Similarity	NPD4198	Discontinued
0.6829	Remote Similarity	NPD6387	Discontinued
0.6825	Remote Similarity	NPD2286	Discontinued
0.6822	Remote Similarity	NPD6696	Suspended
0.681	Remote Similarity	NPD9500	Approved
0.68	Remote Similarity	NPD1894	Discontinued
0.6791	Remote Similarity	NPD2203	Discontinued
0.6791	Remote Similarity	NPD6346	Approved
0.6789	Remote Similarity	NPD800	Approved
0.6788	Remote Similarity	NPD4477	Approved
0.6788	Remote Similarity	NPD4476	Approved
0.6786	Remote Similarity	NPD1693	Approved
0.6777	Remote Similarity	NPD228	Approved
0.6769	Remote Similarity	NPD1134	Approved
0.6769	Remote Similarity	NPD1129	Approved
0.6769	Remote Similarity	NPD1133	Approved
0.6769	Remote Similarity	NPD1131	Approved
0.6769	Remote Similarity	NPD1203	Approved
0.6769	Remote Similarity	NPD1135	Approved
0.6767	Remote Similarity	NPD6798	Discontinued
0.6767	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD9495	Approved
0.675	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1755	Approved
0.6741	Remote Similarity	NPD6355	Discontinued
0.6739	Remote Similarity	NPD2346	Discontinued
0.6739	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7843	Approved
0.6719	Remote Similarity	NPD1535	Discovery
0.6719	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1611	Approved
0.6719	Remote Similarity	NPD1281	Approved
0.6718	Remote Similarity	NPD258	Approved
0.6718	Remote Similarity	NPD2195	Approved
0.6718	Remote Similarity	NPD2194	Approved
0.6718	Remote Similarity	NPD257	Approved
0.6715	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3750	Approved
0.6714	Remote Similarity	NPD3400	Discontinued
0.6698	Remote Similarity	NPD9491	Approved
0.6694	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD8651	Approved
0.6692	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD3225	Approved
0.6692	Remote Similarity	NPD7008	Discontinued
0.6692	Remote Similarity	NPD3136	Phase 2
0.6691	Remote Similarity	NPD4097	Suspended

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