NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	278.782
LogP:	3.326
LogD:	3.09
LogS:	-4.032
# Rotatable Bonds:	6
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.632
Synthetic Accessibility Score:	2.141
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.673
MDCK Permeability:	1.3111400221532676e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.196
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.784

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	89.43678283691406%
Volume Distribution (VD):	0.444
Pgp-substrate:	8.22513484954834%

ADMET: Metabolism

CYP1A2-inhibitor:	0.288
CYP1A2-substrate:	0.396
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.157
CYP2C9-substrate:	0.751
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.307
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	8.992
Half-life (T1/2):	0.819

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.918
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.881
Carcinogencity:	0.55
Eye Corrosion:	0.02
Eye Irritation:	0.795
Respiratory Toxicity:	0.095

Download Data

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

Natural Product: NPC37858

Natural Product ID:	NPC37858
*Common Name:**	Boropinic Acid
IUPAC Name:	(E)-3-[3-methoxy-4-(3-methylbut-2-enoxy)phenyl]prop-2-enoic acid
Synonyms:	Boropinic Acid
Standard InCHIKey:	DFEYQZMFSVQTGR-FNORWQNLSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-11(2)8-9-19-13-6-4-12(5-7-15(16)17)10-14(13)18-3/h4-8,10H,9H2,1-3H3,(H,16,17)/b7-5+
SMILES:	COc1cc(/C=C/C(=O)O)ccc1OCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL218105
PubChem CID:	10682896
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
NPO16098	Boronia pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076549]
NPO16098	Boronia pinnata	Species	Rutaceae	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	11
MIC	1
Others	26

Activity Type	# Activity
Cell Line	15
Individual Protein	8
NON-MOLECULAR	3
Organism	5
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1495	Individual Protein	Geranylgeranyl pyrophosphate synthetase	Homo sapiens	Inhibition	=	9.3	%	PMID[569996]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[569997]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[569997]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[570000]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[570000]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	100000.0	nM	PMID[570000]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	100000.0	nM	PMID[570000]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.725	n.a.	PMID[570002]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.796	n.a.	PMID[570002]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.095	n.a.	PMID[570002]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.253	n.a.	PMID[570002]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.222	n.a.	PMID[570002]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.661	n.a.	PMID[570002]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	2.203	n.a.	PMID[570002]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	200000.0	nM	PMID[570003]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	700.0	nM	PMID[570004]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	0.0008	nM	PMID[570004]
NPT457	Cell Line	BT-549	Homo sapiens	IC50	=	15000.0	nM	PMID[570004]
NPT83	Cell Line	MCF7	Homo sapiens	Efficacy	=	102.0	%	PMID[570004]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Efficacy	=	89.0	%	PMID[570004]
NPT457	Cell Line	BT-549	Homo sapiens	Efficacy	=	97.0	%	PMID[570004]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	1.62	ug.mL-1	PMID[569995]
NPT2	Others	Unspecified		Inhibition	=	31.0	%	PMID[569996]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[569997]
NPT2	Others	Unspecified		Activity	=	23.1	%	PMID[569997]
NPT2	Others	Unspecified		Activity	=	62.2	%	PMID[569997]
NPT2	Others	Unspecified		Activity	=	84.0	%	PMID[569997]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	36.0	%	PMID[569999]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.72	umol	PMID[569999]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	12.0	%	PMID[569999]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	55.0	%	PMID[569999]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[570000]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.78	ng	PMID[570001]
NPT2	Others	Unspecified		IC50	=	6100.0	nM	PMID[570004]
NPT2	Others	Unspecified		Efficacy	=	98.0	%	PMID[570004]

☑ 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 NPC37858 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	256
0.1-0.2	1570
0.2-0.3	5088
0.3-0.4	11793
0.4-0.5	5908
0.5-0.6	5187
0.6-0.7	9914
0.7-0.8	2623
0.8-0.85	244
0.85-0.9	86
0.9-0.95	25
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9732	High Similarity	NPC124916
0.955	High Similarity	NPC294941
0.9478	High Similarity	NPC204466
0.9397	High Similarity	NPC70752
0.9391	High Similarity	NPC202474
0.9217	High Similarity	NPC70744
0.9217	High Similarity	NPC107588
0.9217	High Similarity	NPC277460
0.9217	High Similarity	NPC272471
0.9217	High Similarity	NPC164706
0.9217	High Similarity	NPC137537
0.916	High Similarity	NPC60517
0.916	High Similarity	NPC146886
0.916	High Similarity	NPC246704
0.916	High Similarity	NPC20443
0.9107	High Similarity	NPC245552
0.9107	High Similarity	NPC55300
0.9083	High Similarity	NPC289459
0.906	High Similarity	NPC2058
0.9052	High Similarity	NPC159916
0.9027	High Similarity	NPC165646
0.9008	High Similarity	NPC120225
0.9008	High Similarity	NPC213552
0.8974	High Similarity	NPC57501
0.8966	High Similarity	NPC280001
0.8947	High Similarity	NPC303522
0.8926	High Similarity	NPC27352
0.8919	High Similarity	NPC258171
0.8917	High Similarity	NPC21238
0.8908	High Similarity	NPC310373
0.8908	High Similarity	NPC114845
0.888	High Similarity	NPC5423
0.887	High Similarity	NPC261453
0.887	High Similarity	NPC328593
0.887	High Similarity	NPC33749
0.8862	High Similarity	NPC109275
0.8862	High Similarity	NPC110313
0.8852	High Similarity	NPC127604
0.885	High Similarity	NPC179309
0.8833	High Similarity	NPC288238
0.8829	High Similarity	NPC176971
0.8824	High Similarity	NPC267064
0.8814	High Similarity	NPC69670
0.8803	High Similarity	NPC212643
0.8803	High Similarity	NPC199209
0.8803	High Similarity	NPC39793
0.8793	High Similarity	NPC233669
0.8793	High Similarity	NPC474967
0.879	High Similarity	NPC48315
0.879	High Similarity	NPC83062
0.8783	High Similarity	NPC95381
0.875	High Similarity	NPC151530
0.875	High Similarity	NPC227894
0.875	High Similarity	NPC157473
0.8739	High Similarity	NPC128730
0.8739	High Similarity	NPC222175
0.8739	High Similarity	NPC288760
0.873	High Similarity	NPC245120
0.8718	High Similarity	NPC281277
0.8707	High Similarity	NPC217472
0.8667	High Similarity	NPC14007
0.8667	High Similarity	NPC269843
0.8667	High Similarity	NPC60962
0.8667	High Similarity	NPC471877
0.8667	High Similarity	NPC224814
0.8667	High Similarity	NPC109083
0.8667	High Similarity	NPC189844
0.8649	High Similarity	NPC2518
0.8644	High Similarity	NPC65791
0.8629	High Similarity	NPC194841
0.8618	High Similarity	NPC58279
0.8618	High Similarity	NPC300326
0.8618	High Similarity	NPC280767
0.8618	High Similarity	NPC87113
0.8609	High Similarity	NPC226250
0.8607	High Similarity	NPC279379
0.8607	High Similarity	NPC108545
0.8605	High Similarity	NPC37468
0.8595	High Similarity	NPC193484
0.8594	High Similarity	NPC111635
0.8571	High Similarity	NPC19242
0.8571	High Similarity	NPC203124
0.8571	High Similarity	NPC205502
0.8571	High Similarity	NPC309434
0.856	High Similarity	NPC478215
0.8559	High Similarity	NPC268317
0.8559	High Similarity	NPC179686
0.8538	High Similarity	NPC126206
0.8525	High Similarity	NPC286573
0.8522	High Similarity	NPC137685
0.8516	High Similarity	NPC475468
0.8512	High Similarity	NPC158949
0.8512	High Similarity	NPC199023
0.8512	High Similarity	NPC307253
0.8496	Intermediate Similarity	NPC326447
0.8492	Intermediate Similarity	NPC241354
0.8487	Intermediate Similarity	NPC185738
0.8482	Intermediate Similarity	NPC283546
0.8473	Intermediate Similarity	NPC164148
0.8473	Intermediate Similarity	NPC100389
0.8473	Intermediate Similarity	NPC43500
0.8468	Intermediate Similarity	NPC85830
0.8468	Intermediate Similarity	NPC310905
0.8468	Intermediate Similarity	NPC12714
0.8462	Intermediate Similarity	NPC471664
0.8462	Intermediate Similarity	NPC471665
0.8462	Intermediate Similarity	NPC186418
0.8455	Intermediate Similarity	NPC106659
0.8455	Intermediate Similarity	NPC229084
0.8455	Intermediate Similarity	NPC160900
0.8455	Intermediate Similarity	NPC470887
0.8455	Intermediate Similarity	NPC18984
0.845	Intermediate Similarity	NPC135127
0.845	Intermediate Similarity	NPC471110
0.845	Intermediate Similarity	NPC92830
0.8448	Intermediate Similarity	NPC139617
0.8448	Intermediate Similarity	NPC78918
0.8443	Intermediate Similarity	NPC177291
0.8443	Intermediate Similarity	NPC194416
0.8438	Intermediate Similarity	NPC137669
0.8435	Intermediate Similarity	NPC7097
0.8435	Intermediate Similarity	NPC246358
0.8435	Intermediate Similarity	NPC36108
0.8435	Intermediate Similarity	NPC233731
0.8417	Intermediate Similarity	NPC212743
0.8417	Intermediate Similarity	NPC275519
0.8407	Intermediate Similarity	NPC473855
0.8403	Intermediate Similarity	NPC111225
0.8376	Intermediate Similarity	NPC131530
0.8374	Intermediate Similarity	NPC114298
0.8372	Intermediate Similarity	NPC241341
0.8372	Intermediate Similarity	NPC36437
0.8372	Intermediate Similarity	NPC233018
0.8361	Intermediate Similarity	NPC470849
0.8361	Intermediate Similarity	NPC470848
0.8347	Intermediate Similarity	NPC141791
0.8347	Intermediate Similarity	NPC263386
0.8333	Intermediate Similarity	NPC13067
0.8321	Intermediate Similarity	NPC157554
0.8321	Intermediate Similarity	NPC90431
0.8321	Intermediate Similarity	NPC120852
0.832	Intermediate Similarity	NPC271985
0.832	Intermediate Similarity	NPC473626
0.8319	Intermediate Similarity	NPC292792
0.8319	Intermediate Similarity	NPC109637
0.8308	Intermediate Similarity	NPC237594
0.8308	Intermediate Similarity	NPC119060
0.8308	Intermediate Similarity	NPC249791
0.8308	Intermediate Similarity	NPC309744
0.8308	Intermediate Similarity	NPC476387
0.8306	Intermediate Similarity	NPC4181
0.8306	Intermediate Similarity	NPC164778
0.8306	Intermediate Similarity	NPC238810
0.8306	Intermediate Similarity	NPC257976
0.8306	Intermediate Similarity	NPC242372
0.8304	Intermediate Similarity	NPC51633
0.8295	Intermediate Similarity	NPC2190
0.8291	Intermediate Similarity	NPC257124
0.8291	Intermediate Similarity	NPC156840
0.8291	Intermediate Similarity	NPC8547
0.8291	Intermediate Similarity	NPC173746
0.8284	Intermediate Similarity	NPC157816
0.8281	Intermediate Similarity	NPC285776
0.8281	Intermediate Similarity	NPC244799
0.8281	Intermediate Similarity	NPC298268
0.8281	Intermediate Similarity	NPC240722
0.8271	Intermediate Similarity	NPC202700
0.8268	Intermediate Similarity	NPC210674
0.8258	Intermediate Similarity	NPC95162
0.8258	Intermediate Similarity	NPC76336
0.8258	Intermediate Similarity	NPC20511
0.8258	Intermediate Similarity	NPC52086
0.8258	Intermediate Similarity	NPC139548
0.8258	Intermediate Similarity	NPC148835
0.8254	Intermediate Similarity	NPC276014
0.8246	Intermediate Similarity	NPC227255
0.8244	Intermediate Similarity	NPC55040
0.824	Intermediate Similarity	NPC293701
0.824	Intermediate Similarity	NPC312404
0.824	Intermediate Similarity	NPC273686
0.824	Intermediate Similarity	NPC48990
0.824	Intermediate Similarity	NPC74478
0.824	Intermediate Similarity	NPC109822
0.824	Intermediate Similarity	NPC114901
0.824	Intermediate Similarity	NPC94276
0.8231	Intermediate Similarity	NPC36490
0.823	Intermediate Similarity	NPC304638
0.823	Intermediate Similarity	NPC192596
0.8226	Intermediate Similarity	NPC256167
0.8226	Intermediate Similarity	NPC71090
0.8222	Intermediate Similarity	NPC478239
0.822	Intermediate Similarity	NPC199462
0.8217	Intermediate Similarity	NPC73738
0.8214	Intermediate Similarity	NPC107101
0.8209	Intermediate Similarity	NPC300611
0.8205	Intermediate Similarity	NPC46844
0.8203	Intermediate Similarity	NPC27239
0.8203	Intermediate Similarity	NPC123127
0.8197	Intermediate Similarity	NPC135961
0.8197	Intermediate Similarity	NPC98748

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 NPC37858 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	983
0.2-0.3	1714
0.3-0.4	2691
0.4-0.5	1749
0.5-0.6	996
0.6-0.7	677
0.7-0.8	113
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8919	High Similarity	NPD1358	Approved
0.8496	Intermediate Similarity	NPD3134	Approved
0.8487	Intermediate Similarity	NPD5536	Phase 2
0.8455	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8361	Intermediate Similarity	NPD3496	Discontinued
0.8291	Intermediate Similarity	NPD228	Approved
0.8197	Intermediate Similarity	NPD1357	Approved
0.8092	Intermediate Similarity	NPD447	Suspended
0.8047	Intermediate Similarity	NPD9494	Approved
0.8034	Intermediate Similarity	NPD2684	Approved
0.8	Intermediate Similarity	NPD5283	Phase 1
0.7984	Intermediate Similarity	NPD4626	Approved
0.7917	Intermediate Similarity	NPD7843	Approved
0.7903	Intermediate Similarity	NPD5691	Approved
0.7879	Intermediate Similarity	NPD4060	Phase 1
0.7869	Intermediate Similarity	NPD7157	Approved
0.784	Intermediate Similarity	NPD1778	Approved
0.7803	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD9697	Approved
0.7769	Intermediate Similarity	NPD5535	Approved
0.7754	Intermediate Similarity	NPD4110	Phase 3
0.7754	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1653	Approved
0.7717	Intermediate Similarity	NPD3705	Approved
0.7705	Intermediate Similarity	NPD1241	Discontinued
0.7672	Intermediate Similarity	NPD291	Approved
0.7652	Intermediate Similarity	NPD7095	Approved
0.7647	Intermediate Similarity	NPD290	Approved
0.763	Intermediate Similarity	NPD2653	Approved
0.7619	Intermediate Similarity	NPD5585	Approved
0.7589	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD422	Phase 1
0.7556	Intermediate Similarity	NPD4340	Discontinued
0.7519	Intermediate Similarity	NPD3027	Phase 3
0.7519	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD3686	Approved
0.75	Intermediate Similarity	NPD3687	Approved
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD6653	Approved
0.748	Intermediate Similarity	NPD821	Approved
0.7463	Intermediate Similarity	NPD6798	Discontinued
0.7462	Intermediate Similarity	NPD2982	Phase 2
0.7462	Intermediate Similarity	NPD2983	Phase 2
0.7444	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD1933	Approved
0.7426	Intermediate Similarity	NPD230	Phase 1
0.7426	Intermediate Similarity	NPD6355	Discontinued
0.7417	Intermediate Similarity	NPD968	Approved
0.741	Intermediate Similarity	NPD7266	Discontinued
0.741	Intermediate Similarity	NPD1375	Discontinued
0.7407	Intermediate Similarity	NPD6233	Phase 2
0.7407	Intermediate Similarity	NPD4062	Phase 3
0.7402	Intermediate Similarity	NPD1894	Discontinued
0.7402	Intermediate Similarity	NPD9545	Approved
0.7385	Intermediate Similarity	NPD2981	Phase 2
0.7377	Intermediate Similarity	NPD556	Approved
0.7365	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4140	Approved
0.7353	Intermediate Similarity	NPD1613	Approved
0.7353	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD987	Approved
0.7345	Intermediate Similarity	NPD9365	Approved
0.7333	Intermediate Similarity	NPD1048	Approved
0.7333	Intermediate Similarity	NPD411	Approved
0.7329	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD4359	Approved
0.7315	Intermediate Similarity	NPD3817	Phase 2
0.7313	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1535	Discovery
0.7304	Intermediate Similarity	NPD9296	Approved
0.7302	Intermediate Similarity	NPD6671	Approved
0.7293	Intermediate Similarity	NPD5647	Approved
0.7292	Intermediate Similarity	NPD3146	Approved
0.7292	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD1608	Approved
0.7252	Intermediate Similarity	NPD1481	Phase 2
0.7246	Intermediate Similarity	NPD2492	Phase 1
0.7239	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3018	Phase 2
0.7231	Intermediate Similarity	NPD3847	Discontinued
0.7226	Intermediate Similarity	NPD1558	Phase 1
0.7222	Intermediate Similarity	NPD4357	Discontinued
0.7218	Intermediate Similarity	NPD1203	Approved
0.7218	Intermediate Similarity	NPD2797	Approved
0.7214	Intermediate Similarity	NPD6032	Approved
0.7214	Intermediate Similarity	NPD2161	Phase 2
0.7214	Intermediate Similarity	NPD2935	Discontinued
0.7211	Intermediate Similarity	NPD3111	Phase 1
0.7206	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3144	Approved
0.7206	Intermediate Similarity	NPD3145	Approved
0.7194	Intermediate Similarity	NPD7097	Phase 1
0.719	Intermediate Similarity	NPD8127	Discontinued
0.7185	Intermediate Similarity	NPD6832	Phase 2
0.7183	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4162	Approved
0.7183	Intermediate Similarity	NPD1652	Phase 2
0.7176	Intermediate Similarity	NPD776	Approved
0.7176	Intermediate Similarity	NPD1611	Approved
0.7176	Intermediate Similarity	NPD1091	Approved
0.7174	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD1019	Discontinued
0.7164	Intermediate Similarity	NPD6584	Phase 3
0.7163	Intermediate Similarity	NPD3656	Approved
0.7163	Intermediate Similarity	NPD5763	Approved
0.7163	Intermediate Similarity	NPD5762	Approved
0.7154	Intermediate Similarity	NPD5846	Approved
0.7154	Intermediate Similarity	NPD6516	Phase 2
0.7154	Intermediate Similarity	NPD17	Approved
0.7153	Intermediate Similarity	NPD2674	Phase 3
0.7153	Intermediate Similarity	NPD5745	Approved
0.7152	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD1283	Approved
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD3225	Approved
0.7133	Intermediate Similarity	NPD8166	Discontinued
0.7132	Intermediate Similarity	NPD5163	Phase 2
0.7132	Intermediate Similarity	NPD1182	Approved
0.7123	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6386	Approved
0.7114	Intermediate Similarity	NPD6385	Approved
0.7113	Intermediate Similarity	NPD7153	Discontinued
0.7103	Intermediate Similarity	NPD6799	Approved
0.7101	Intermediate Similarity	NPD3620	Phase 2
0.7101	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3021	Approved
0.7097	Intermediate Similarity	NPD3022	Approved
0.7092	Intermediate Similarity	NPD2240	Approved
0.7092	Intermediate Similarity	NPD2239	Approved
0.7083	Intermediate Similarity	NPD6190	Approved
0.708	Intermediate Similarity	NPD3268	Approved
0.7075	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3685	Discontinued
0.7067	Intermediate Similarity	NPD1934	Approved
0.7059	Intermediate Similarity	NPD2614	Approved
0.7055	Intermediate Similarity	NPD4123	Phase 3
0.705	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5124	Phase 1
0.7045	Intermediate Similarity	NPD1281	Approved
0.7025	Intermediate Similarity	NPD5844	Phase 1
0.7023	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2801	Approved
0.7015	Intermediate Similarity	NPD2922	Phase 1
0.7015	Intermediate Similarity	NPD8651	Approved
0.7014	Intermediate Similarity	NPD6331	Phase 2
0.7007	Intermediate Similarity	NPD6273	Approved
0.7007	Intermediate Similarity	NPD5746	Approved
0.7007	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1548	Phase 1
0.6993	Remote Similarity	NPD2424	Discontinued
0.6993	Remote Similarity	NPD4534	Discontinued
0.6992	Remote Similarity	NPD2231	Phase 2
0.6992	Remote Similarity	NPD2235	Phase 2
0.6985	Remote Similarity	NPD2861	Phase 2
0.6985	Remote Similarity	NPD2237	Approved
0.6985	Remote Similarity	NPD454	Approved
0.698	Remote Similarity	NPD3455	Phase 2
0.6978	Remote Similarity	NPD825	Approved
0.6978	Remote Similarity	NPD826	Approved
0.6978	Remote Similarity	NPD2979	Phase 3
0.6977	Remote Similarity	NPD9493	Approved
0.6972	Remote Similarity	NPD2438	Suspended
0.6972	Remote Similarity	NPD1551	Phase 2
0.6966	Remote Similarity	NPD3887	Approved
0.6963	Remote Similarity	NPD6362	Approved
0.6963	Remote Similarity	NPD1818	Approved
0.6963	Remote Similarity	NPD1820	Approved
0.6963	Remote Similarity	NPD1819	Approved
0.6963	Remote Similarity	NPD1817	Approved
0.6957	Remote Similarity	NPD5109	Approved
0.6957	Remote Similarity	NPD5110	Phase 2
0.6957	Remote Similarity	NPD5111	Phase 2
0.6948	Remote Similarity	NPD919	Approved
0.6947	Remote Similarity	NPD1651	Approved
0.6944	Remote Similarity	NPD3060	Approved
0.6944	Remote Similarity	NPD4236	Phase 3
0.6944	Remote Similarity	NPD4237	Approved
0.694	Remote Similarity	NPD5327	Phase 3
0.694	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6583	Phase 3
0.694	Remote Similarity	NPD6582	Phase 2
0.6939	Remote Similarity	NPD4739	Approved
0.6934	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4908	Phase 1
0.6929	Remote Similarity	NPD769	Approved
0.6918	Remote Similarity	NPD7440	Discontinued
0.6917	Remote Similarity	NPD1610	Phase 2
0.6913	Remote Similarity	NPD4210	Discontinued
0.6908	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4870	Approved
0.6906	Remote Similarity	NPD8032	Phase 2
0.6901	Remote Similarity	NPD4308	Phase 3
0.6897	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7039	Approved
0.6894	Remote Similarity	NPD7038	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