NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	204.08
Volume:	218.104
LogP:	2.856
LogD:	2.653
LogS:	-2.823
# 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:	0.584
Synthetic Accessibility Score:	2.298
Fsp3:	0.083
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:	-4.812
MDCK Permeability:	1.704838541627396e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.555
30% Bioavailability (F30%):	0.201

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	96.88424682617188%
Volume Distribution (VD):	0.337
Pgp-substrate:	1.1540822982788086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.404
CYP2C9-substrate:	0.326
CYP2D6-inhibitor:	0.057
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.086

ADMET: Excretion

Clearance (CL):	5.469
Half-life (T1/2):	0.927

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.659
Drug-inuced Liver Injury (DILI):	0.063
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.469
Maximum Recommended Daily Dose:	0.373
Skin Sensitization:	0.935
Carcinogencity:	0.107
Eye Corrosion:	0.119
Eye Irritation:	0.947
Respiratory Toxicity:	0.593

Download Data

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

Natural Product: NPC470202

Natural Product ID:	NPC470202
*Common Name:**	3-(4-Hydroxy-3-Allylphenyl)Acrylic Acid
IUPAC Name:	(E)-3-(4-hydroxy-3-prop-2-enylphenyl)prop-2-enoic acid
Synonyms:
Standard InCHIKey:	MAYTXVQHJNLZKO-FNORWQNLSA-N
Standard InCHI:	InChI=1S/C12H12O3/c1-2-3-10-8-9(4-6-11(10)13)5-7-12(14)15/h2,4-8,13H,1,3H2,(H,14,15)/b7-5+
SMILES:	C=CCC1=C(C=CC(=C1)C=CC(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1818960
PubChem CID:	21422472
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
Others	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	98.4	%	PMID[522273]
NPT2	Others	Unspecified		Ratio	=	0.9	n.a.	PMID[522273]

☑ 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 NPC470202 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	241
0.1-0.2	1654
0.2-0.3	4526
0.3-0.4	13070
0.4-0.5	6190
0.5-0.6	9540
0.6-0.7	6126
0.7-0.8	1162
0.8-0.85	150
0.85-0.9	29
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9794	High Similarity	NPC303141
0.9592	High Similarity	NPC243677
0.9406	High Similarity	NPC471954
0.9406	High Similarity	NPC75272
0.9368	High Similarity	NPC246679
0.9307	High Similarity	NPC470039
0.9263	High Similarity	NPC81010
0.9263	High Similarity	NPC32977
0.8854	High Similarity	NPC204210
0.88	High Similarity	NPC253746
0.8776	High Similarity	NPC257182
0.8776	High Similarity	NPC8392
0.8774	High Similarity	NPC199462
0.8763	High Similarity	NPC181709
0.8725	High Similarity	NPC93831
0.87	High Similarity	NPC128723
0.87	High Similarity	NPC245561
0.8687	High Similarity	NPC283711
0.8673	High Similarity	NPC128062
0.8646	High Similarity	NPC70436
0.8636	High Similarity	NPC474890
0.8636	High Similarity	NPC161943
0.8636	High Similarity	NPC273282
0.8627	High Similarity	NPC304638
0.8627	High Similarity	NPC135784
0.8614	High Similarity	NPC52472
0.86	High Similarity	NPC77492
0.86	High Similarity	NPC140619
0.8598	High Similarity	NPC228988
0.8586	High Similarity	NPC286006
0.8526	High Similarity	NPC155393
0.8519	High Similarity	NPC242136
0.8515	High Similarity	NPC252821
0.8515	High Similarity	NPC122005
0.8476	Intermediate Similarity	NPC228737
0.8469	Intermediate Similarity	NPC45040
0.8455	Intermediate Similarity	NPC83718
0.8454	Intermediate Similarity	NPC258219
0.8454	Intermediate Similarity	NPC123273
0.8454	Intermediate Similarity	NPC318325
0.8454	Intermediate Similarity	NPC242240
0.8447	Intermediate Similarity	NPC13426
0.8447	Intermediate Similarity	NPC168829
0.844	Intermediate Similarity	NPC114918
0.8438	Intermediate Similarity	NPC307235
0.8438	Intermediate Similarity	NPC407
0.8438	Intermediate Similarity	NPC23167
0.8431	Intermediate Similarity	NPC225506
0.8421	Intermediate Similarity	NPC175313
0.8416	Intermediate Similarity	NPC201967
0.8411	Intermediate Similarity	NPC473809
0.8411	Intermediate Similarity	NPC183700
0.84	Intermediate Similarity	NPC144682
0.8396	Intermediate Similarity	NPC206341
0.8381	Intermediate Similarity	NPC294902
0.8381	Intermediate Similarity	NPC1786
0.8381	Intermediate Similarity	NPC1075
0.8367	Intermediate Similarity	NPC300017
0.8365	Intermediate Similarity	NPC288411
0.8351	Intermediate Similarity	NPC113460
0.8351	Intermediate Similarity	NPC25493
0.835	Intermediate Similarity	NPC94343
0.8349	Intermediate Similarity	NPC211421
0.8333	Intermediate Similarity	NPC228609
0.8333	Intermediate Similarity	NPC139946
0.8333	Intermediate Similarity	NPC130193
0.8333	Intermediate Similarity	NPC197783
0.8333	Intermediate Similarity	NPC171843
0.8318	Intermediate Similarity	NPC79543
0.8316	Intermediate Similarity	NPC265146
0.8302	Intermediate Similarity	NPC260952
0.83	Intermediate Similarity	NPC151715
0.83	Intermediate Similarity	NPC289769
0.8288	Intermediate Similarity	NPC471936
0.8286	Intermediate Similarity	NPC13495
0.8286	Intermediate Similarity	NPC127676
0.8286	Intermediate Similarity	NPC138942
0.8286	Intermediate Similarity	NPC227255
0.8283	Intermediate Similarity	NPC306074
0.8283	Intermediate Similarity	NPC304541
0.8273	Intermediate Similarity	NPC41851
0.8265	Intermediate Similarity	NPC280347
0.8265	Intermediate Similarity	NPC177420
0.8261	Intermediate Similarity	NPC67300
0.8235	Intermediate Similarity	NPC260000
0.8229	Intermediate Similarity	NPC248817
0.8229	Intermediate Similarity	NPC286904
0.8224	Intermediate Similarity	NPC68260
0.8224	Intermediate Similarity	NPC279887
0.8218	Intermediate Similarity	NPC26244
0.8218	Intermediate Similarity	NPC274678
0.8214	Intermediate Similarity	NPC183154
0.8214	Intermediate Similarity	NPC278652
0.8214	Intermediate Similarity	NPC263754
0.8208	Intermediate Similarity	NPC69332
0.8208	Intermediate Similarity	NPC95178
0.8208	Intermediate Similarity	NPC29989
0.8208	Intermediate Similarity	NPC54765
0.82	Intermediate Similarity	NPC138117
0.82	Intermediate Similarity	NPC271440
0.82	Intermediate Similarity	NPC325292
0.819	Intermediate Similarity	NPC2518
0.819	Intermediate Similarity	NPC174991
0.8182	Intermediate Similarity	NPC55561
0.8173	Intermediate Similarity	NPC472585
0.8163	Intermediate Similarity	NPC104216
0.8155	Intermediate Similarity	NPC80027
0.8155	Intermediate Similarity	NPC280869
0.8148	Intermediate Similarity	NPC88141
0.8148	Intermediate Similarity	NPC95172
0.8148	Intermediate Similarity	NPC282855
0.8148	Intermediate Similarity	NPC26013
0.8142	Intermediate Similarity	NPC184527
0.8137	Intermediate Similarity	NPC473388
0.8131	Intermediate Similarity	NPC141523
0.8131	Intermediate Similarity	NPC29883
0.8131	Intermediate Similarity	NPC226699
0.8125	Intermediate Similarity	NPC124436
0.812	Intermediate Similarity	NPC184219
0.8119	Intermediate Similarity	NPC152415
0.8119	Intermediate Similarity	NPC27323
0.8119	Intermediate Similarity	NPC316301
0.8108	Intermediate Similarity	NPC197513
0.81	Intermediate Similarity	NPC155908
0.8095	Intermediate Similarity	NPC68269
0.8095	Intermediate Similarity	NPC108497
0.8091	Intermediate Similarity	NPC286222
0.8091	Intermediate Similarity	NPC17693
0.8073	Intermediate Similarity	NPC63345
0.8073	Intermediate Similarity	NPC208229
0.807	Intermediate Similarity	NPC473767
0.8061	Intermediate Similarity	NPC184169
0.8056	Intermediate Similarity	NPC262365
0.8056	Intermediate Similarity	NPC95344
0.8056	Intermediate Similarity	NPC100551
0.8056	Intermediate Similarity	NPC61885
0.8056	Intermediate Similarity	NPC31274
0.8056	Intermediate Similarity	NPC63698
0.8056	Intermediate Similarity	NPC224584
0.8053	Intermediate Similarity	NPC122117
0.8053	Intermediate Similarity	NPC160199
0.8051	Intermediate Similarity	NPC93219
0.8051	Intermediate Similarity	NPC244495
0.8039	Intermediate Similarity	NPC313650
0.8037	Intermediate Similarity	NPC271274
0.8037	Intermediate Similarity	NPC184658
0.8037	Intermediate Similarity	NPC6984
0.8037	Intermediate Similarity	NPC70843
0.8019	Intermediate Similarity	NPC261573
0.8019	Intermediate Similarity	NPC120693
0.8019	Intermediate Similarity	NPC79672
0.8019	Intermediate Similarity	NPC8931
0.8019	Intermediate Similarity	NPC119860
0.8	Intermediate Similarity	NPC47950
0.8	Intermediate Similarity	NPC226250
0.8	Intermediate Similarity	NPC300478
0.8	Intermediate Similarity	NPC470355
0.8	Intermediate Similarity	NPC192
0.7983	Intermediate Similarity	NPC473751
0.7982	Intermediate Similarity	NPC326187
0.7982	Intermediate Similarity	NPC98392
0.7981	Intermediate Similarity	NPC92730
0.7981	Intermediate Similarity	NPC132078
0.7981	Intermediate Similarity	NPC78119
0.7981	Intermediate Similarity	NPC51333
0.7981	Intermediate Similarity	NPC216468
0.798	Intermediate Similarity	NPC19680
0.798	Intermediate Similarity	NPC27974
0.7961	Intermediate Similarity	NPC292730
0.7961	Intermediate Similarity	NPC216520
0.7961	Intermediate Similarity	NPC312132
0.7961	Intermediate Similarity	NPC132271
0.7961	Intermediate Similarity	NPC259512
0.7961	Intermediate Similarity	NPC82664
0.7949	Intermediate Similarity	NPC475192
0.7944	Intermediate Similarity	NPC99557
0.7944	Intermediate Similarity	NPC474839
0.7944	Intermediate Similarity	NPC219286
0.7941	Intermediate Similarity	NPC245187
0.7931	Intermediate Similarity	NPC216216
0.7931	Intermediate Similarity	NPC131868
0.7931	Intermediate Similarity	NPC164852
0.7931	Intermediate Similarity	NPC241001
0.7928	Intermediate Similarity	NPC26615
0.7925	Intermediate Similarity	NPC269212
0.7921	Intermediate Similarity	NPC270547
0.7921	Intermediate Similarity	NPC231150
0.7917	Intermediate Similarity	NPC243688
0.7909	Intermediate Similarity	NPC222084
0.7909	Intermediate Similarity	NPC44732
0.7909	Intermediate Similarity	NPC222905
0.7909	Intermediate Similarity	NPC296683
0.7905	Intermediate Similarity	NPC48730
0.7905	Intermediate Similarity	NPC248396
0.7905	Intermediate Similarity	NPC129373
0.7905	Intermediate Similarity	NPC174911
0.7905	Intermediate Similarity	NPC72729
0.7905	Intermediate Similarity	NPC211885
0.7905	Intermediate Similarity	NPC213730
0.79	Intermediate Similarity	NPC98772

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 NPC470202 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	1028
0.2-0.3	1381
0.3-0.4	2862
0.4-0.5	1974
0.5-0.6	1142
0.6-0.7	438
0.7-0.8	65
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD1809	Phase 2
0.8384	Intermediate Similarity	NPD845	Approved
0.8218	Intermediate Similarity	NPD2859	Approved
0.8218	Intermediate Similarity	NPD2860	Approved
0.8173	Intermediate Similarity	NPD846	Approved
0.8173	Intermediate Similarity	NPD940	Approved
0.8131	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD111	Approved
0.8119	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8119	Intermediate Similarity	NPD2934	Approved
0.8119	Intermediate Similarity	NPD2933	Approved
0.8056	Intermediate Similarity	NPD9266	Approved
0.8056	Intermediate Similarity	NPD74	Approved
0.8051	Intermediate Similarity	NPD1164	Approved
0.8039	Intermediate Similarity	NPD844	Approved
0.8	Intermediate Similarity	NPD4626	Approved
0.7981	Intermediate Similarity	NPD3020	Approved
0.7963	Intermediate Similarity	NPD9263	Approved
0.7963	Intermediate Similarity	NPD9267	Approved
0.7963	Intermediate Similarity	NPD9264	Approved
0.7961	Intermediate Similarity	NPD288	Approved
0.7905	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD9493	Approved
0.7759	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD256	Approved
0.7719	Intermediate Similarity	NPD255	Approved
0.7712	Intermediate Similarity	NPD422	Phase 1
0.7672	Intermediate Similarity	NPD9545	Approved
0.7615	Intermediate Similarity	NPD9697	Approved
0.7607	Intermediate Similarity	NPD5691	Approved
0.7593	Intermediate Similarity	NPD9261	Approved
0.7545	Intermediate Similarity	NPD3134	Approved
0.7522	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9568	Approved
0.7478	Intermediate Similarity	NPD9281	Approved
0.7477	Intermediate Similarity	NPD1358	Approved
0.7477	Intermediate Similarity	NPD2342	Discontinued
0.7407	Intermediate Similarity	NPD1242	Phase 1
0.7391	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD9273	Approved
0.7379	Intermediate Similarity	NPD9256	Approved
0.7379	Intermediate Similarity	NPD9258	Approved
0.7373	Intermediate Similarity	NPD1759	Phase 1
0.7364	Intermediate Similarity	NPD9608	Approved
0.7364	Intermediate Similarity	NPD9610	Approved
0.735	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD3021	Approved
0.7345	Intermediate Similarity	NPD3022	Approved
0.7308	Intermediate Similarity	NPD2935	Discontinued
0.7304	Intermediate Similarity	NPD7635	Approved
0.7288	Intermediate Similarity	NPD1758	Phase 1
0.7273	Intermediate Similarity	NPD1201	Approved
0.7263	Intermediate Similarity	NPD9716	Approved
0.7257	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5304	Approved
0.7227	Intermediate Similarity	NPD5303	Approved
0.7213	Intermediate Similarity	NPD9717	Approved
0.72	Intermediate Similarity	NPD4208	Discontinued
0.72	Intermediate Similarity	NPD4212	Discontinued
0.7193	Intermediate Similarity	NPD4750	Phase 3
0.7193	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3496	Discontinued
0.7188	Intermediate Similarity	NPD4060	Phase 1
0.7177	Intermediate Similarity	NPD1203	Approved
0.7177	Intermediate Similarity	NPD2797	Approved
0.7177	Intermediate Similarity	NPD1470	Approved
0.7176	Intermediate Similarity	NPD5408	Approved
0.7176	Intermediate Similarity	NPD5406	Approved
0.7176	Intermediate Similarity	NPD5404	Approved
0.7176	Intermediate Similarity	NPD5405	Approved
0.7165	Intermediate Similarity	NPD3764	Approved
0.7158	Intermediate Similarity	NPD9087	Approved
0.7155	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD4207	Discontinued
0.7131	Intermediate Similarity	NPD1535	Discovery
0.7117	Intermediate Similarity	NPD9500	Approved
0.7107	Intermediate Similarity	NPD4589	Approved
0.7107	Intermediate Similarity	NPD2932	Approved
0.7107	Intermediate Similarity	NPD3019	Approved
0.7099	Intermediate Similarity	NPD2799	Discontinued
0.7097	Intermediate Similarity	NPD1283	Approved
0.7094	Intermediate Similarity	NPD2234	Approved
0.7094	Intermediate Similarity	NPD2228	Approved
0.7094	Intermediate Similarity	NPD2229	Approved
0.7091	Intermediate Similarity	NPD3028	Approved
0.708	Intermediate Similarity	NPD1445	Approved
0.708	Intermediate Similarity	NPD1444	Approved
0.7073	Intermediate Similarity	NPD1481	Phase 2
0.7069	Intermediate Similarity	NPD228	Approved
0.7064	Intermediate Similarity	NPD9495	Approved
0.7063	Intermediate Similarity	NPD5736	Approved
0.7059	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3847	Discontinued
0.7041	Intermediate Similarity	NPD9088	Approved
0.7034	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2313	Discontinued
0.703	Intermediate Similarity	NPD9491	Approved
0.7025	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD9377	Approved
0.7009	Intermediate Similarity	NPD9379	Approved
0.699	Remote Similarity	NPD9257	Approved
0.699	Remote Similarity	NPD9259	Approved
0.6984	Remote Similarity	NPD257	Approved
0.6984	Remote Similarity	NPD258	Approved
0.6975	Remote Similarity	NPD6671	Approved
0.6967	Remote Similarity	NPD2286	Discontinued
0.6964	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1929	Approved
0.6964	Remote Similarity	NPD1930	Approved
0.6963	Remote Similarity	NPD7003	Approved
0.696	Remote Similarity	NPD3225	Approved
0.6957	Remote Similarity	NPD2684	Approved
0.6949	Remote Similarity	NPD1241	Discontinued
0.6942	Remote Similarity	NPD1548	Phase 1
0.6942	Remote Similarity	NPD1894	Discontinued
0.6942	Remote Similarity	NPD3091	Approved
0.6939	Remote Similarity	NPD9294	Approved
0.6935	Remote Similarity	NPD9269	Phase 2
0.693	Remote Similarity	NPD968	Approved
0.6923	Remote Similarity	NPD1240	Approved
0.6923	Remote Similarity	NPD943	Approved
0.6911	Remote Similarity	NPD3143	Discontinued
0.6905	Remote Similarity	NPD1133	Approved
0.6905	Remote Similarity	NPD1131	Approved
0.6905	Remote Similarity	NPD1129	Approved
0.6905	Remote Similarity	NPD1135	Approved
0.6905	Remote Similarity	NPD1134	Approved
0.6903	Remote Similarity	NPD1237	Approved
0.6899	Remote Similarity	NPD3268	Approved
0.6897	Remote Similarity	NPD1792	Phase 2
0.6891	Remote Similarity	NPD5951	Approved
0.6885	Remote Similarity	NPD9268	Approved
0.687	Remote Similarity	NPD290	Approved
0.687	Remote Similarity	NPD5124	Phase 1
0.687	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1138	Approved
0.6855	Remote Similarity	NPD1610	Phase 2
0.6855	Remote Similarity	NPD1281	Approved
0.6855	Remote Similarity	NPD1611	Approved
0.6852	Remote Similarity	NPD1202	Approved
0.6847	Remote Similarity	NPD2066	Phase 3
0.6846	Remote Similarity	NPD520	Approved
0.6846	Remote Similarity	NPD6663	Approved
0.6842	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD3750	Approved
0.6832	Remote Similarity	NPD226	Approved
0.6829	Remote Similarity	NPD4059	Approved
0.6829	Remote Similarity	NPD1778	Approved
0.6818	Remote Similarity	NPD1607	Approved
0.6803	Remote Similarity	NPD7330	Discontinued
0.68	Remote Similarity	NPD3070	Discontinued
0.6797	Remote Similarity	NPD9569	Approved
0.6792	Remote Similarity	NPD800	Approved
0.6789	Remote Similarity	NPD688	Clinical (unspecified phase)
0.678	Remote Similarity	NPD1137	Approved
0.678	Remote Similarity	NPD1139	Approved
0.6777	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD987	Approved
0.6769	Remote Similarity	NPD6798	Discontinued
0.6765	Remote Similarity	NPD9089	Approved
0.6759	Remote Similarity	NPD159	Clinical (unspecified phase)
0.675	Remote Similarity	NPD690	Clinical (unspecified phase)
0.675	Remote Similarity	NPD475	Phase 2
0.675	Remote Similarity	NPD497	Approved
0.6748	Remote Similarity	NPD4093	Discontinued
0.6746	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD1089	Approved
0.6729	Remote Similarity	NPD1086	Approved
0.6729	Remote Similarity	NPD1090	Approved
0.6723	Remote Similarity	NPD7843	Approved
0.6723	Remote Similarity	NPD821	Approved
0.6721	Remote Similarity	NPD856	Approved
0.6721	Remote Similarity	NPD16	Approved
0.6721	Remote Similarity	NPD318	Approved
0.6721	Remote Similarity	NPD317	Approved
0.672	Remote Similarity	NPD3092	Approved
0.6719	Remote Similarity	NPD2798	Approved
0.6718	Remote Similarity	NPD4248	Discontinued
0.6716	Remote Similarity	NPD4308	Phase 3
0.6716	Remote Similarity	NPD1510	Phase 2
0.6715	Remote Similarity	NPD3400	Discontinued
0.6715	Remote Similarity	NPD8166	Discontinued
0.6699	Remote Similarity	NPD3971	Phase 1
0.6697	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD9712	Approved
0.6695	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1751	Approved
0.6694	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD196	Phase 1
0.6692	Remote Similarity	NPD3136	Phase 2
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD6647	Phase 2
0.6667	Remote Similarity	NPD826	Approved
0.6667	Remote Similarity	NPD4477	Approved
0.6667	Remote Similarity	NPD496	Approved
0.6667	Remote Similarity	NPD825	Approved
0.6667	Remote Similarity	NPD4476	Approved

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