NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.09
Volume:	220.74
LogP:	1.958
LogD:	1.749
LogS:	-2.678
# Rotatable Bonds:	4
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.563
Synthetic Accessibility Score:	1.96
Fsp3:	0.25
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:	-4.589
MDCK Permeability:	1.9719076590263285e-05
Pgp-inhibitor:	0.255
Pgp-substrate:	0.924
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.422

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.989
Plasma Protein Binding (PPB):	84.06829833984375%
Volume Distribution (VD):	0.704
Pgp-substrate:	22.28005599975586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.824
CYP2C19-inhibitor:	0.733
CYP2C19-substrate:	0.759
CYP2C9-inhibitor:	0.241
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.082
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.205
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	6.673
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.02
Drug-inuced Liver Injury (DILI):	0.738
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.939
Carcinogencity:	0.542
Eye Corrosion:	0.68
Eye Irritation:	0.975
Respiratory Toxicity:	0.221

Download Data

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

Natural Product: NPC245552

Natural Product ID:	NPC245552
*Common Name:**	[2-Methoxy-4-[(E)-Prop-1-Enyl]Phenyl] Acetate
IUPAC Name:	[2-methoxy-4-[(E)-prop-1-enyl]phenyl] acetate
Synonyms:
Standard InCHIKey:	IUSBVFZKQJGVEP-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C12H14O3/c1-4-5-10-6-7-11(15-9(2)13)12(8-10)14-3/h4-8H,1-3H3/b5-4+
SMILES:	C/C=C/c1ccc(c(c1)OC)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1609480
PubChem CID:	876160
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002319] Phenol esters

*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
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94055-X]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.3390/70200245]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22870812]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23435948]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24617303]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18681	Artemisia scoparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18681	Artemisia scoparia	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
Potency	6

Activity Type	# Activity
Individual Protein	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	223.9	nM	PMID[457135]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[457135]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[457135]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[457135]
NPT2	Others	Unspecified		Potency	n.a.	12589.3	nM	PMID[457135]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	21192.3	nM	PMID[457135]

☑ 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 NPC245552 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	304
0.1-0.2	2141
0.2-0.3	7226
0.3-0.4	12307
0.4-0.5	3845
0.5-0.6	8230
0.6-0.7	6951
0.7-0.8	1496
0.8-0.85	134
0.85-0.9	53
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.981	High Similarity	NPC303522
0.9364	High Similarity	NPC124916
0.9364	High Similarity	NPC159916
0.9238	High Similarity	NPC258171
0.9126	High Similarity	NPC310905
0.9126	High Similarity	NPC12714
0.9115	High Similarity	NPC267064
0.9107	High Similarity	NPC37858
0.9029	High Similarity	NPC107101
0.9	High Similarity	NPC294941
0.8952	High Similarity	NPC292792
0.8952	High Similarity	NPC283546
0.8942	High Similarity	NPC307425
0.8899	High Similarity	NPC55300
0.8879	High Similarity	NPC470887
0.885	High Similarity	NPC277460
0.8818	High Similarity	NPC165646
0.8807	High Similarity	NPC179309
0.8761	High Similarity	NPC212643
0.8761	High Similarity	NPC199209
0.8718	High Similarity	NPC279379
0.8718	High Similarity	NPC21238
0.8716	High Similarity	NPC127326
0.8704	High Similarity	NPC227894
0.8696	High Similarity	NPC2058
0.8696	High Similarity	NPC202474
0.8692	High Similarity	NPC473855
0.8692	High Similarity	NPC128730
0.8692	High Similarity	NPC473393
0.8684	High Similarity	NPC137537
0.8684	High Similarity	NPC205502
0.8684	High Similarity	NPC70744
0.8684	High Similarity	NPC164706
0.8684	High Similarity	NPC272471
0.8684	High Similarity	NPC107588
0.8655	High Similarity	NPC127604
0.8624	High Similarity	NPC291837
0.8621	High Similarity	NPC204466
0.8611	High Similarity	NPC176971
0.8609	High Similarity	NPC69670
0.8583	High Similarity	NPC194841
0.8547	High Similarity	NPC114845
0.8547	High Similarity	NPC193484
0.8547	High Similarity	NPC70752
0.8545	High Similarity	NPC7097
0.8545	High Similarity	NPC233731
0.8545	High Similarity	NPC246358
0.8545	High Similarity	NPC36108
0.8534	High Similarity	NPC222175
0.8532	High Similarity	NPC157473
0.8532	High Similarity	NPC151530
0.8512	High Similarity	NPC474623
0.8512	High Similarity	NPC474651
0.8505	High Similarity	NPC179686
0.8475	Intermediate Similarity	NPC288238
0.8468	Intermediate Similarity	NPC88868
0.8468	Intermediate Similarity	NPC25067
0.8468	Intermediate Similarity	NPC231251
0.8468	Intermediate Similarity	NPC31279
0.8468	Intermediate Similarity	NPC137685
0.8462	Intermediate Similarity	NPC471877
0.8448	Intermediate Similarity	NPC57501
0.8426	Intermediate Similarity	NPC109637
0.8393	Intermediate Similarity	NPC173746
0.8393	Intermediate Similarity	NPC257124
0.8393	Intermediate Similarity	NPC139617
0.8393	Intermediate Similarity	NPC8547
0.8393	Intermediate Similarity	NPC203924
0.8393	Intermediate Similarity	NPC78918
0.8393	Intermediate Similarity	NPC156840
0.839	Intermediate Similarity	NPC177291
0.839	Intermediate Similarity	NPC310373
0.839	Intermediate Similarity	NPC194416
0.8378	Intermediate Similarity	NPC259554
0.8378	Intermediate Similarity	NPC165386
0.8374	Intermediate Similarity	NPC19242
0.8374	Intermediate Similarity	NPC244799
0.8374	Intermediate Similarity	NPC240722
0.8361	Intermediate Similarity	NPC210674
0.8349	Intermediate Similarity	NPC238115
0.8349	Intermediate Similarity	NPC288760
0.8348	Intermediate Similarity	NPC111225
0.8348	Intermediate Similarity	NPC268317
0.8333	Intermediate Similarity	NPC60517
0.8333	Intermediate Similarity	NPC246704
0.8333	Intermediate Similarity	NPC87563
0.8333	Intermediate Similarity	NPC20443
0.8333	Intermediate Similarity	NPC146886
0.8319	Intermediate Similarity	NPC280760
0.8305	Intermediate Similarity	NPC307253
0.8293	Intermediate Similarity	NPC27239
0.8293	Intermediate Similarity	NPC123127
0.8279	Intermediate Similarity	NPC474670
0.8276	Intermediate Similarity	NPC185738
0.8276	Intermediate Similarity	NPC280001
0.8276	Intermediate Similarity	NPC39793
0.8273	Intermediate Similarity	NPC326447
0.8264	Intermediate Similarity	NPC289459
0.8264	Intermediate Similarity	NPC27352
0.8264	Intermediate Similarity	NPC85830
0.8264	Intermediate Similarity	NPC280767
0.8257	Intermediate Similarity	NPC2518
0.825	Intermediate Similarity	NPC108545
0.8246	Intermediate Similarity	NPC204120
0.8246	Intermediate Similarity	NPC165106
0.824	Intermediate Similarity	NPC245120
0.824	Intermediate Similarity	NPC5423
0.824	Intermediate Similarity	NPC137669
0.8226	Intermediate Similarity	NPC79184
0.8226	Intermediate Similarity	NPC307042
0.8226	Intermediate Similarity	NPC476399
0.8197	Intermediate Similarity	NPC213552
0.8197	Intermediate Similarity	NPC120225
0.8175	Intermediate Similarity	NPC233018
0.8175	Intermediate Similarity	NPC36437
0.8175	Intermediate Similarity	NPC241341
0.8174	Intermediate Similarity	NPC235250
0.8155	Intermediate Similarity	NPC99886
0.8155	Intermediate Similarity	NPC177844
0.8155	Intermediate Similarity	NPC8002
0.8155	Intermediate Similarity	NPC259134
0.8151	Intermediate Similarity	NPC472596
0.8151	Intermediate Similarity	NPC199023
0.8145	Intermediate Similarity	NPC241354
0.8136	Intermediate Similarity	NPC299406
0.8131	Intermediate Similarity	NPC175298
0.813	Intermediate Similarity	NPC223807
0.813	Intermediate Similarity	NPC474821
0.812	Intermediate Similarity	NPC33271
0.812	Intermediate Similarity	NPC86947
0.8115	Intermediate Similarity	NPC300326
0.8115	Intermediate Similarity	NPC58279
0.8115	Intermediate Similarity	NPC473626
0.811	Intermediate Similarity	NPC309953
0.811	Intermediate Similarity	NPC111635
0.811	Intermediate Similarity	NPC92830
0.811	Intermediate Similarity	NPC474600
0.8108	Intermediate Similarity	NPC1065
0.8103	Intermediate Similarity	NPC473264
0.8103	Intermediate Similarity	NPC475815
0.8103	Intermediate Similarity	NPC47194
0.8095	Intermediate Similarity	NPC319969
0.8095	Intermediate Similarity	NPC123954
0.8087	Intermediate Similarity	NPC95381
0.8077	Intermediate Similarity	NPC71853
0.8073	Intermediate Similarity	NPC51633
0.807	Intermediate Similarity	NPC226250
0.807	Intermediate Similarity	NPC195873
0.8065	Intermediate Similarity	NPC474616
0.8065	Intermediate Similarity	NPC109275
0.8065	Intermediate Similarity	NPC110313
0.8056	Intermediate Similarity	NPC471576
0.8053	Intermediate Similarity	NPC149545
0.8051	Intermediate Similarity	NPC101503
0.8049	Intermediate Similarity	NPC154275
0.8049	Intermediate Similarity	NPC474632
0.8047	Intermediate Similarity	NPC234865
0.8047	Intermediate Similarity	NPC311430
0.8047	Intermediate Similarity	NPC224941
0.8034	Intermediate Similarity	NPC221049
0.8034	Intermediate Similarity	NPC81067
0.8034	Intermediate Similarity	NPC9341
0.8034	Intermediate Similarity	NPC123948
0.8018	Intermediate Similarity	NPC139891
0.8017	Intermediate Similarity	NPC261661
0.8017	Intermediate Similarity	NPC217472
0.8017	Intermediate Similarity	NPC33749
0.8017	Intermediate Similarity	NPC71090
0.8017	Intermediate Similarity	NPC328593
0.8017	Intermediate Similarity	NPC194626
0.8017	Intermediate Similarity	NPC261453
0.8017	Intermediate Similarity	NPC256167
0.8	Intermediate Similarity	NPC321956
0.8	Intermediate Similarity	NPC83062
0.8	Intermediate Similarity	NPC225245
0.8	Intermediate Similarity	NPC476748
0.8	Intermediate Similarity	NPC269843
0.8	Intermediate Similarity	NPC192596
0.8	Intermediate Similarity	NPC48315
0.8	Intermediate Similarity	NPC109083
0.8	Intermediate Similarity	NPC189844
0.8	Intermediate Similarity	NPC131530
0.8	Intermediate Similarity	NPC60962
0.8	Intermediate Similarity	NPC14007
0.8	Intermediate Similarity	NPC158949
0.8	Intermediate Similarity	NPC224814
0.8	Intermediate Similarity	NPC295317
0.7984	Intermediate Similarity	NPC286843
0.7984	Intermediate Similarity	NPC281020
0.7984	Intermediate Similarity	NPC167517
0.7983	Intermediate Similarity	NPC98748
0.7983	Intermediate Similarity	NPC119949
0.7982	Intermediate Similarity	NPC13755
0.7969	Intermediate Similarity	NPC473054
0.7969	Intermediate Similarity	NPC309744
0.7967	Intermediate Similarity	NPC87113
0.7967	Intermediate Similarity	NPC173608
0.7966	Intermediate Similarity	NPC259638
0.7966	Intermediate Similarity	NPC52464
0.7966	Intermediate Similarity	NPC164386

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 NPC245552 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	1134
0.2-0.3	1884
0.3-0.4	2628
0.4-0.5	1623
0.5-0.6	957
0.6-0.7	544
0.7-0.8	97
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8532	High Similarity	NPD1358	Approved
0.8393	Intermediate Similarity	NPD228	Approved
0.8276	Intermediate Similarity	NPD5536	Phase 2
0.8273	Intermediate Similarity	NPD3134	Approved
0.8246	Intermediate Similarity	NPD5283	Phase 1
0.8158	Intermediate Similarity	NPD5535	Approved
0.8018	Intermediate Similarity	NPD9697	Approved
0.7983	Intermediate Similarity	NPD1357	Approved
0.7969	Intermediate Similarity	NPD2653	Approved
0.7965	Intermediate Similarity	NPD2684	Approved
0.7833	Intermediate Similarity	NPD5691	Approved
0.7833	Intermediate Similarity	NPD5585	Approved
0.7805	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD3705	Approved
0.7769	Intermediate Similarity	NPD1778	Approved
0.7752	Intermediate Similarity	NPD447	Suspended
0.7719	Intermediate Similarity	NPD290	Approved
0.7705	Intermediate Similarity	NPD3496	Discontinued
0.7692	Intermediate Similarity	NPD7843	Approved
0.7647	Intermediate Similarity	NPD7157	Approved
0.7642	Intermediate Similarity	NPD1611	Approved
0.7638	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD1241	Discontinued
0.7623	Intermediate Similarity	NPD4626	Approved
0.7623	Intermediate Similarity	NPD17	Approved
0.7597	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD291	Approved
0.7581	Intermediate Similarity	NPD2981	Phase 2
0.7578	Intermediate Similarity	NPD7095	Approved
0.7559	Intermediate Similarity	NPD9494	Approved
0.7556	Intermediate Similarity	NPD4110	Phase 3
0.7556	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD987	Approved
0.7538	Intermediate Similarity	NPD4060	Phase 1
0.752	Intermediate Similarity	NPD4359	Approved
0.752	Intermediate Similarity	NPD2983	Phase 2
0.752	Intermediate Similarity	NPD2982	Phase 2
0.75	Intermediate Similarity	NPD1281	Approved
0.75	Intermediate Similarity	NPD422	Phase 1
0.7459	Intermediate Similarity	NPD1894	Discontinued
0.744	Intermediate Similarity	NPD1608	Approved
0.7407	Intermediate Similarity	NPD9365	Approved
0.7405	Intermediate Similarity	NPD4140	Approved
0.7395	Intermediate Similarity	NPD821	Approved
0.7364	Intermediate Similarity	NPD9296	Approved
0.7348	Intermediate Similarity	NPD1933	Approved
0.7338	Intermediate Similarity	NPD3146	Approved
0.7338	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD8032	Phase 2
0.7328	Intermediate Similarity	NPD968	Approved
0.7323	Intermediate Similarity	NPD1283	Approved
0.7317	Intermediate Similarity	NPD1182	Approved
0.7305	Intermediate Similarity	NPD3687	Approved
0.7305	Intermediate Similarity	NPD3686	Approved
0.7288	Intermediate Similarity	NPD556	Approved
0.7287	Intermediate Similarity	NPD3018	Phase 2
0.7287	Intermediate Similarity	NPD2237	Approved
0.7286	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1558	Phase 1
0.7258	Intermediate Similarity	NPD1651	Approved
0.7252	Intermediate Similarity	NPD6798	Discontinued
0.725	Intermediate Similarity	NPD769	Approved
0.7231	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1535	Discovery
0.7222	Intermediate Similarity	NPD776	Approved
0.7218	Intermediate Similarity	NPD6355	Discontinued
0.7213	Intermediate Similarity	NPD6671	Approved
0.7206	Intermediate Similarity	NPD1375	Discontinued
0.72	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4062	Phase 3
0.7197	Intermediate Similarity	NPD6233	Phase 2
0.7197	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2922	Phase 1
0.7185	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1653	Approved
0.7176	Intermediate Similarity	NPD3027	Phase 3
0.7165	Intermediate Similarity	NPD1481	Phase 2
0.7165	Intermediate Similarity	NPD9717	Approved
0.7164	Intermediate Similarity	NPD2492	Phase 1
0.7164	Intermediate Similarity	NPD6653	Approved
0.7154	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5451	Approved
0.7143	Intermediate Similarity	NPD3847	Discontinued
0.7132	Intermediate Similarity	NPD2161	Phase 2
0.7121	Intermediate Similarity	NPD5111	Phase 2
0.7121	Intermediate Similarity	NPD5109	Approved
0.7121	Intermediate Similarity	NPD3144	Approved
0.7121	Intermediate Similarity	NPD5718	Phase 2
0.7121	Intermediate Similarity	NPD5110	Phase 2
0.7121	Intermediate Similarity	NPD3145	Approved
0.7109	Intermediate Similarity	NPD5327	Phase 3
0.7099	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2614	Approved
0.709	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1019	Discontinued
0.7068	Intermediate Similarity	NPD4870	Approved
0.7068	Intermediate Similarity	NPD2674	Phase 3
0.7063	Intermediate Similarity	NPD5846	Approved
0.7063	Intermediate Similarity	NPD6516	Phase 2
0.7045	Intermediate Similarity	NPD5163	Phase 2
0.7045	Intermediate Similarity	NPD5746	Approved
0.7045	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1840	Phase 2
0.7029	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7153	Discontinued
0.7023	Intermediate Similarity	NPD454	Approved
0.7016	Intermediate Similarity	NPD3596	Phase 2
0.7015	Intermediate Similarity	NPD2979	Phase 3
0.7007	Intermediate Similarity	NPD6032	Approved
0.7007	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD3266	Approved
0.7	Intermediate Similarity	NPD3267	Approved
0.7	Intermediate Similarity	NPD2797	Approved
0.6992	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1048	Approved
0.6992	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD411	Approved
0.6985	Remote Similarity	NPD7097	Phase 1
0.6978	Remote Similarity	NPD4162	Approved
0.697	Remote Similarity	NPD6832	Phase 2
0.6963	Remote Similarity	NPD4340	Discontinued
0.696	Remote Similarity	NPD7644	Approved
0.6957	Remote Similarity	NPD3656	Approved
0.6957	Remote Similarity	NPD5762	Approved
0.6957	Remote Similarity	NPD5763	Approved
0.6947	Remote Similarity	NPD5647	Approved
0.6947	Remote Similarity	NPD6584	Phase 3
0.6944	Remote Similarity	NPD4210	Discontinued
0.694	Remote Similarity	NPD5745	Approved
0.6935	Remote Similarity	NPD709	Approved
0.6929	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6331	Phase 2
0.6923	Remote Similarity	NPD3225	Approved
0.6906	Remote Similarity	NPD4534	Discontinued
0.6905	Remote Similarity	NPD6580	Approved
0.6905	Remote Similarity	NPD6581	Approved
0.6905	Remote Similarity	NPD1548	Phase 1
0.6905	Remote Similarity	NPD9545	Approved
0.6897	Remote Similarity	NPD3111	Phase 1
0.6892	Remote Similarity	NPD3817	Phase 2
0.6889	Remote Similarity	NPD3620	Phase 2
0.6889	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2239	Approved
0.6884	Remote Similarity	NPD2240	Approved
0.6875	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1203	Approved
0.687	Remote Similarity	NPD1818	Approved
0.687	Remote Similarity	NPD1820	Approved
0.687	Remote Similarity	NPD1819	Approved
0.687	Remote Similarity	NPD1817	Approved
0.6867	Remote Similarity	NPD919	Approved
0.6866	Remote Similarity	NPD1296	Phase 2
0.6861	Remote Similarity	NPD6896	Approved
0.6861	Remote Similarity	NPD6895	Approved
0.686	Remote Similarity	NPD3022	Approved
0.686	Remote Similarity	NPD3021	Approved
0.6857	Remote Similarity	NPD1652	Phase 2
0.6853	Remote Similarity	NPD4739	Approved
0.6852	Remote Similarity	NPD111	Approved
0.685	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1420	Approved
0.6846	Remote Similarity	NPD1421	Approved
0.6846	Remote Similarity	NPD3685	Discontinued
0.6838	Remote Similarity	NPD230	Phase 1
0.6838	Remote Similarity	NPD3657	Discovery
0.6824	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1091	Approved
0.6822	Remote Similarity	NPD1610	Phase 2
0.6821	Remote Similarity	NPD5677	Discontinued
0.6815	Remote Similarity	NPD3532	Approved
0.6815	Remote Similarity	NPD3531	Approved
0.6815	Remote Similarity	NPD3530	Approved
0.6809	Remote Similarity	NPD4628	Phase 3
0.6806	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6386	Approved
0.6803	Remote Similarity	NPD6385	Approved
0.68	Remote Similarity	NPD2557	Approved
0.6797	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD196	Phase 1
0.6794	Remote Similarity	NPD8651	Approved
0.6788	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5958	Discontinued
0.6781	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD8127	Discontinued
0.6774	Remote Similarity	NPD594	Approved
0.6774	Remote Similarity	NPD592	Approved
0.6769	Remote Similarity	NPD2231	Phase 2
0.6769	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD2235	Phase 2
0.6767	Remote Similarity	NPD2861	Phase 2
0.6765	Remote Similarity	NPD4307	Phase 2
0.6763	Remote Similarity	NPD3539	Phase 1
0.6763	Remote Similarity	NPD2531	Phase 2
0.6763	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