NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	176.08
Volume:	194.654
LogP:	2.475
LogD:	2.24
LogS:	-3.069
# Rotatable Bonds:	4
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.401
Synthetic Accessibility Score:	1.877
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.387
MDCK Permeability:	2.9250391889945604e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.055
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.946
Plasma Protein Binding (PPB):	84.38555145263672%
Volume Distribution (VD):	0.559
Pgp-substrate:	13.721275329589844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.9
CYP1A2-substrate:	0.178
CYP2C19-inhibitor:	0.774
CYP2C19-substrate:	0.362
CYP2C9-inhibitor:	0.354
CYP2C9-substrate:	0.835
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.798
CYP3A4-inhibitor:	0.156
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	5.359
Half-life (T1/2):	0.745

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.016
Drug-inuced Liver Injury (DILI):	0.213
AMES Toxicity:	0.305
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.492
Skin Sensitization:	0.945
Carcinogencity:	0.824
Eye Corrosion:	0.179
Eye Irritation:	0.951
Respiratory Toxicity:	0.513

Download Data

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

Natural Product: NPC307425

Natural Product ID:	NPC307425
*Common Name:**	(4-Prop-2-Enylphenyl) Acetate
IUPAC Name:	(4-prop-2-enylphenyl) acetate
Synonyms:	Acetic Acid 4-Allyl-Phenyl Ester
Standard InCHIKey:	AXHHVVBUOKYKJO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H12O2/c1-3-4-10-5-7-11(8-6-10)13-9(2)12/h3,5-8H,1,4H2,2H3
SMILES:	C=CCc1ccc(cc1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL108937
PubChem CID:	523825
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
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30949	Eugenia caryopyhllata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	11.0	%	PMID[570134]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	65000.0	nM	PMID[570135]

☑ 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 NPC307425 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	266
0.1-0.2	2455
0.2-0.3	6991
0.3-0.4	11801
0.4-0.5	4476
0.5-0.6	9493
0.6-0.7	6314
0.7-0.8	811
0.8-0.85	48
0.85-0.9	27
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC107101
0.9588	High Similarity	NPC283546
0.949	High Similarity	NPC473855
0.949	High Similarity	NPC473393
0.9307	High Similarity	NPC259554
0.9293	High Similarity	NPC128730
0.9216	High Similarity	NPC88868
0.9216	High Similarity	NPC231251
0.9216	High Similarity	NPC25067
0.9208	High Similarity	NPC291837
0.92	High Similarity	NPC176971
0.9109	High Similarity	NPC157473
0.9109	High Similarity	NPC151530
0.9091	High Similarity	NPC179686
0.9	High Similarity	NPC109637
0.8952	High Similarity	NPC303522
0.8942	High Similarity	NPC245552
0.8911	High Similarity	NPC238115
0.8868	High Similarity	NPC235250
0.8842	High Similarity	NPC71853
0.8824	High Similarity	NPC1065
0.8824	High Similarity	NPC326447
0.8812	High Similarity	NPC2518
0.875	High Similarity	NPC321956
0.8737	High Similarity	NPC8002
0.8737	High Similarity	NPC259134
0.8737	High Similarity	NPC177844
0.8737	High Similarity	NPC99886
0.8725	High Similarity	NPC139891
0.8704	High Similarity	NPC470860
0.8687	High Similarity	NPC175298
0.8679	High Similarity	NPC280760
0.8627	High Similarity	NPC108875
0.8627	High Similarity	NPC38079
0.8614	High Similarity	NPC51633
0.86	High Similarity	NPC471576
0.8585	High Similarity	NPC233238
0.8571	High Similarity	NPC234639
0.8571	High Similarity	NPC149545
0.8545	High Similarity	NPC96705
0.8544	High Similarity	NPC470393
0.8529	High Similarity	NPC298224
0.8529	High Similarity	NPC192596
0.8515	High Similarity	NPC13755
0.8491	Intermediate Similarity	NPC473809
0.8447	Intermediate Similarity	NPC38209
0.844	Intermediate Similarity	NPC51345
0.8416	Intermediate Similarity	NPC100870
0.8416	Intermediate Similarity	NPC171843
0.8384	Intermediate Similarity	NPC471581
0.8378	Intermediate Similarity	NPC293424
0.8378	Intermediate Similarity	NPC265547
0.8378	Intermediate Similarity	NPC124916
0.8378	Intermediate Similarity	NPC159916
0.8378	Intermediate Similarity	NPC152306
0.8365	Intermediate Similarity	NPC288760
0.8365	Intermediate Similarity	NPC227255
0.8349	Intermediate Similarity	NPC87563
0.8333	Intermediate Similarity	NPC199462
0.8319	Intermediate Similarity	NPC267064
0.8318	Intermediate Similarity	NPC141068
0.8317	Intermediate Similarity	NPC95755
0.8304	Intermediate Similarity	NPC298796
0.8304	Intermediate Similarity	NPC281356
0.8304	Intermediate Similarity	NPC264976
0.8288	Intermediate Similarity	NPC471498
0.8288	Intermediate Similarity	NPC183154
0.8288	Intermediate Similarity	NPC263754
0.8288	Intermediate Similarity	NPC471503
0.8273	Intermediate Similarity	NPC296526
0.8257	Intermediate Similarity	NPC109241
0.8252	Intermediate Similarity	NPC300166
0.8246	Intermediate Similarity	NPC52247
0.8235	Intermediate Similarity	NPC307039
0.8214	Intermediate Similarity	NPC101503
0.8208	Intermediate Similarity	NPC258171
0.8198	Intermediate Similarity	NPC33717
0.8198	Intermediate Similarity	NPC128633
0.819	Intermediate Similarity	NPC127676
0.819	Intermediate Similarity	NPC8302
0.8174	Intermediate Similarity	NPC248429
0.8174	Intermediate Similarity	NPC96286
0.8173	Intermediate Similarity	NPC304638
0.8165	Intermediate Similarity	NPC266116
0.8158	Intermediate Similarity	NPC180006
0.8158	Intermediate Similarity	NPC235190
0.8158	Intermediate Similarity	NPC163200
0.8155	Intermediate Similarity	NPC253746
0.8142	Intermediate Similarity	NPC37858
0.8142	Intermediate Similarity	NPC98748
0.8103	Intermediate Similarity	NPC470887
0.8103	Intermediate Similarity	NPC472518
0.8103	Intermediate Similarity	NPC315807
0.8095	Intermediate Similarity	NPC292792
0.8091	Intermediate Similarity	NPC90903
0.8087	Intermediate Similarity	NPC187868
0.8077	Intermediate Similarity	NPC84325
0.8077	Intermediate Similarity	NPC310905
0.8077	Intermediate Similarity	NPC12714
0.807	Intermediate Similarity	NPC474874
0.807	Intermediate Similarity	NPC473290
0.807	Intermediate Similarity	NPC471504
0.8034	Intermediate Similarity	NPC89630
0.8034	Intermediate Similarity	NPC201667
0.8034	Intermediate Similarity	NPC111347
0.8034	Intermediate Similarity	NPC73413
0.8018	Intermediate Similarity	NPC294941
0.8018	Intermediate Similarity	NPC252004
0.8017	Intermediate Similarity	NPC257188
0.8017	Intermediate Similarity	NPC13007
0.8	Intermediate Similarity	NPC322569
0.8	Intermediate Similarity	NPC305205
0.7982	Intermediate Similarity	NPC106141
0.7982	Intermediate Similarity	NPC46844
0.7982	Intermediate Similarity	NPC183648
0.7966	Intermediate Similarity	NPC244495
0.7966	Intermediate Similarity	NPC93219
0.7961	Intermediate Similarity	NPC470161
0.7959	Intermediate Similarity	NPC304760
0.7949	Intermediate Similarity	NPC273772
0.7949	Intermediate Similarity	NPC109675
0.7949	Intermediate Similarity	NPC279379
0.7946	Intermediate Similarity	NPC220540
0.7944	Intermediate Similarity	NPC113457
0.7931	Intermediate Similarity	NPC144418
0.7925	Intermediate Similarity	NPC474603
0.7925	Intermediate Similarity	NPC241224
0.7925	Intermediate Similarity	NPC12987
0.7913	Intermediate Similarity	NPC193193
0.7913	Intermediate Similarity	NPC230951
0.7913	Intermediate Similarity	NPC31314
0.7913	Intermediate Similarity	NPC14177
0.7913	Intermediate Similarity	NPC247553
0.7909	Intermediate Similarity	NPC23332
0.7909	Intermediate Similarity	NPC55300
0.7899	Intermediate Similarity	NPC188327
0.7899	Intermediate Similarity	NPC234109
0.7895	Intermediate Similarity	NPC205502
0.7895	Intermediate Similarity	NPC277460
0.789	Intermediate Similarity	NPC79543
0.7885	Intermediate Similarity	NPC132725
0.7881	Intermediate Similarity	NPC27671
0.7881	Intermediate Similarity	NPC291899
0.7876	Intermediate Similarity	NPC163398
0.787	Intermediate Similarity	NPC194034
0.787	Intermediate Similarity	NPC251306
0.7863	Intermediate Similarity	NPC291189
0.7863	Intermediate Similarity	NPC476332
0.7863	Intermediate Similarity	NPC69403
0.7863	Intermediate Similarity	NPC473464
0.785	Intermediate Similarity	NPC42383
0.785	Intermediate Similarity	NPC475269
0.7845	Intermediate Similarity	NPC319378
0.7845	Intermediate Similarity	NPC302107
0.7843	Intermediate Similarity	NPC81010
0.7843	Intermediate Similarity	NPC32977
0.7838	Intermediate Similarity	NPC115379
0.7838	Intermediate Similarity	NPC165646
0.7835	Intermediate Similarity	NPC58616
0.7835	Intermediate Similarity	NPC125306
0.7833	Intermediate Similarity	NPC243688
0.7826	Intermediate Similarity	NPC234956
0.7818	Intermediate Similarity	NPC179309
0.7815	Intermediate Similarity	NPC471827
0.7815	Intermediate Similarity	NPC168259
0.7815	Intermediate Similarity	NPC471828
0.7807	Intermediate Similarity	NPC212643
0.7807	Intermediate Similarity	NPC199209
0.7798	Intermediate Similarity	NPC206341
0.7798	Intermediate Similarity	NPC201959
0.7798	Intermediate Similarity	NPC75440
0.7797	Intermediate Similarity	NPC154176
0.7797	Intermediate Similarity	NPC173350
0.7797	Intermediate Similarity	NPC21238
0.7797	Intermediate Similarity	NPC290605
0.7788	Intermediate Similarity	NPC322358
0.7778	Intermediate Similarity	NPC326801
0.7769	Intermediate Similarity	NPC199204
0.7769	Intermediate Similarity	NPC185066
0.7769	Intermediate Similarity	NPC472519
0.7768	Intermediate Similarity	NPC26524
0.7759	Intermediate Similarity	NPC202474
0.7759	Intermediate Similarity	NPC2058
0.775	Intermediate Similarity	NPC471826
0.775	Intermediate Similarity	NPC474476
0.775	Intermediate Similarity	NPC127604
0.775	Intermediate Similarity	NPC101894
0.7748	Intermediate Similarity	NPC139946
0.7748	Intermediate Similarity	NPC266932
0.7748	Intermediate Similarity	NPC57879
0.7739	Intermediate Similarity	NPC70744
0.7739	Intermediate Similarity	NPC272471
0.7739	Intermediate Similarity	NPC107588
0.7739	Intermediate Similarity	NPC137537
0.7739	Intermediate Similarity	NPC164706
0.7736	Intermediate Similarity	NPC94343
0.7731	Intermediate Similarity	NPC140521
0.7731	Intermediate Similarity	NPC221798
0.7727	Intermediate Similarity	NPC471954
0.7727	Intermediate Similarity	NPC474272

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 NPC307425 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	1124
0.2-0.3	1537
0.3-0.4	2669
0.4-0.5	1843
0.5-0.6	1062
0.6-0.7	514
0.7-0.8	124
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9038	High Similarity	NPD5535	Approved
0.8824	High Similarity	NPD3134	Approved
0.8738	High Similarity	NPD1358	Approved
0.8725	High Similarity	NPD9697	Approved
0.8302	Intermediate Similarity	NPD2684	Approved
0.8257	Intermediate Similarity	NPD1241	Discontinued
0.8246	Intermediate Similarity	NPD422	Phase 1
0.8053	Intermediate Similarity	NPD1894	Discontinued
0.8	Intermediate Similarity	NPD821	Approved
0.8	Intermediate Similarity	NPD7843	Approved
0.7982	Intermediate Similarity	NPD5691	Approved
0.7931	Intermediate Similarity	NPD1611	Approved
0.7931	Intermediate Similarity	NPD1535	Discovery
0.7913	Intermediate Similarity	NPD17	Approved
0.787	Intermediate Similarity	NPD290	Approved
0.7863	Intermediate Similarity	NPD1481	Phase 2
0.7845	Intermediate Similarity	NPD3496	Discontinued
0.7826	Intermediate Similarity	NPD5585	Approved
0.7815	Intermediate Similarity	NPD987	Approved
0.7788	Intermediate Similarity	NPD7157	Approved
0.7778	Intermediate Similarity	NPD968	Approved
0.7769	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD1778	Approved
0.7759	Intermediate Similarity	NPD4626	Approved
0.7727	Intermediate Similarity	NPD5451	Approved
0.7712	Intermediate Similarity	NPD9717	Approved
0.7712	Intermediate Similarity	NPD1608	Approved
0.7692	Intermediate Similarity	NPD3847	Discontinued
0.7667	Intermediate Similarity	NPD3267	Approved
0.7667	Intermediate Similarity	NPD2797	Approved
0.7667	Intermediate Similarity	NPD3266	Approved
0.7627	Intermediate Similarity	NPD1281	Approved
0.7623	Intermediate Similarity	NPD2614	Approved
0.7589	Intermediate Similarity	NPD228	Approved
0.7581	Intermediate Similarity	NPD8032	Phase 2
0.7565	Intermediate Similarity	NPD3596	Phase 2
0.7561	Intermediate Similarity	NPD5746	Approved
0.7561	Intermediate Similarity	NPD7095	Approved
0.7561	Intermediate Similarity	NPD5163	Phase 2
0.7549	Intermediate Similarity	NPD9365	Approved
0.7541	Intermediate Similarity	NPD454	Approved
0.752	Intermediate Similarity	NPD4140	Approved
0.75	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4359	Approved
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1296	Phase 2
0.75	Intermediate Similarity	NPD6798	Discontinued
0.748	Intermediate Similarity	NPD6832	Phase 2
0.7478	Intermediate Similarity	NPD6671	Approved
0.7475	Intermediate Similarity	NPD111	Approved
0.7459	Intermediate Similarity	NPD1019	Discontinued
0.7456	Intermediate Similarity	NPD5283	Phase 1
0.744	Intermediate Similarity	NPD5745	Approved
0.744	Intermediate Similarity	NPD4062	Phase 3
0.744	Intermediate Similarity	NPD6233	Phase 2
0.7438	Intermediate Similarity	NPD1283	Approved
0.7438	Intermediate Similarity	NPD3225	Approved
0.7436	Intermediate Similarity	NPD1548	Phase 1
0.7436	Intermediate Similarity	NPD6580	Approved
0.7436	Intermediate Similarity	NPD6581	Approved
0.7402	Intermediate Similarity	NPD2653	Approved
0.7398	Intermediate Similarity	NPD2237	Approved
0.7381	Intermediate Similarity	NPD4060	Phase 1
0.7377	Intermediate Similarity	NPD1203	Approved
0.7373	Intermediate Similarity	NPD1651	Approved
0.7373	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD769	Approved
0.736	Intermediate Similarity	NPD3268	Approved
0.7355	Intermediate Similarity	NPD3685	Discontinued
0.735	Intermediate Similarity	NPD5536	Phase 2
0.7333	Intermediate Similarity	NPD2933	Approved
0.7333	Intermediate Similarity	NPD2934	Approved
0.7328	Intermediate Similarity	NPD2557	Approved
0.7323	Intermediate Similarity	NPD6355	Discontinued
0.7311	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5846	Approved
0.7311	Intermediate Similarity	NPD6516	Phase 2
0.7295	Intermediate Similarity	NPD196	Phase 1
0.7288	Intermediate Similarity	NPD1182	Approved
0.7288	Intermediate Similarity	NPD9545	Approved
0.7281	Intermediate Similarity	NPD1137	Approved
0.7281	Intermediate Similarity	NPD1139	Approved
0.7264	Intermediate Similarity	NPD2860	Approved
0.7264	Intermediate Similarity	NPD2859	Approved
0.7244	Intermediate Similarity	NPD4307	Phase 2
0.7236	Intermediate Similarity	NPD6362	Approved
0.7217	Intermediate Similarity	NPD1138	Approved
0.7213	Intermediate Similarity	NPD5327	Phase 3
0.7213	Intermediate Similarity	NPD6583	Phase 3
0.7213	Intermediate Similarity	NPD6582	Phase 2
0.7209	Intermediate Similarity	NPD7097	Phase 1
0.7203	Intermediate Similarity	NPD7644	Approved
0.719	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1610	Phase 2
0.7188	Intermediate Similarity	NPD4340	Discontinued
0.7184	Intermediate Similarity	NPD9295	Approved
0.7179	Intermediate Similarity	NPD709	Approved
0.7177	Intermediate Similarity	NPD5647	Approved
0.717	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4870	Approved
0.7157	Intermediate Similarity	NPD1282	Approved
0.7155	Intermediate Similarity	NPD594	Approved
0.7155	Intermediate Similarity	NPD592	Approved
0.7154	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD2486	Discontinued
0.7131	Intermediate Similarity	NPD3972	Approved
0.7131	Intermediate Similarity	NPD1840	Phase 2
0.7109	Intermediate Similarity	NPD2979	Phase 3
0.7099	Intermediate Similarity	NPD4476	Approved
0.7099	Intermediate Similarity	NPD2240	Approved
0.7099	Intermediate Similarity	NPD4477	Approved
0.7099	Intermediate Similarity	NPD2239	Approved
0.7097	Intermediate Similarity	NPD1817	Approved
0.7097	Intermediate Similarity	NPD1820	Approved
0.7097	Intermediate Similarity	NPD1819	Approved
0.7097	Intermediate Similarity	NPD1818	Approved
0.7091	Intermediate Similarity	NPD291	Approved
0.7087	Intermediate Similarity	NPD411	Approved
0.7087	Intermediate Similarity	NPD1048	Approved
0.7083	Intermediate Similarity	NPD3444	Approved
0.7083	Intermediate Similarity	NPD3049	Approved
0.7083	Intermediate Similarity	NPD1357	Approved
0.7083	Intermediate Similarity	NPD3443	Approved
0.7083	Intermediate Similarity	NPD3445	Approved
0.7077	Intermediate Similarity	NPD1536	Approved
0.7073	Intermediate Similarity	NPD1421	Approved
0.7073	Intermediate Similarity	NPD6539	Approved
0.7073	Intermediate Similarity	NPD2429	Approved
0.7073	Intermediate Similarity	NPD1420	Approved
0.7073	Intermediate Similarity	NPD6542	Approved
0.7073	Intermediate Similarity	NPD6543	Approved
0.7073	Intermediate Similarity	NPD2428	Approved
0.7073	Intermediate Similarity	NPD6540	Phase 3
0.7068	Intermediate Similarity	NPD1652	Phase 2
0.7064	Intermediate Similarity	NPD3020	Approved
0.7054	Intermediate Similarity	NPD4622	Approved
0.7054	Intermediate Similarity	NPD5124	Phase 1
0.7054	Intermediate Similarity	NPD4618	Approved
0.7054	Intermediate Similarity	NPD447	Suspended
0.7054	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3705	Approved
0.7045	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2353	Approved
0.7045	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6584	Phase 3
0.704	Intermediate Similarity	NPD3690	Phase 2
0.704	Intermediate Similarity	NPD3691	Phase 2
0.7034	Intermediate Similarity	NPD6387	Discontinued
0.7025	Intermediate Similarity	NPD2554	Approved
0.7025	Intermediate Similarity	NPD2667	Approved
0.7025	Intermediate Similarity	NPD2556	Approved
0.7025	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2668	Approved
0.7023	Intermediate Similarity	NPD4308	Phase 3
0.7023	Intermediate Similarity	NPD3748	Approved
0.7016	Intermediate Similarity	NPD6538	Approved
0.7016	Intermediate Similarity	NPD6541	Approved
0.7016	Intermediate Similarity	NPD1876	Approved
0.7	Intermediate Similarity	NPD6653	Approved
0.7	Intermediate Similarity	NPD3028	Approved
0.6992	Remote Similarity	NPD4534	Discontinued
0.6992	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3142	Approved
0.6977	Remote Similarity	NPD3140	Approved
0.6975	Remote Similarity	NPD9493	Approved
0.697	Remote Similarity	NPD1537	Approved
0.697	Remote Similarity	NPD1519	Approved
0.697	Remote Similarity	NPD2862	Discontinued
0.697	Remote Similarity	NPD1538	Phase 1
0.6967	Remote Similarity	NPD3294	Phase 2
0.6967	Remote Similarity	NPD3447	Discontinued
0.6953	Remote Similarity	NPD2313	Discontinued
0.6949	Remote Similarity	NPD595	Approved
0.6949	Remote Similarity	NPD593	Approved
0.6947	Remote Similarity	NPD1520	Approved
0.6947	Remote Similarity	NPD5689	Approved
0.6947	Remote Similarity	NPD5688	Approved
0.6947	Remote Similarity	NPD1521	Approved
0.6942	Remote Similarity	NPD6382	Discontinued
0.6942	Remote Similarity	NPD2595	Approved
0.6942	Remote Similarity	NPD2594	Approved
0.694	Remote Similarity	NPD1243	Approved
0.694	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD846	Approved
0.6937	Remote Similarity	NPD940	Approved
0.6935	Remote Similarity	NPD4129	Approved
0.6935	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5373	Approved
0.693	Remote Similarity	NPD5374	Approved
0.6929	Remote Similarity	NPD4908	Phase 1
0.6929	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1933	Approved
0.6923	Remote Similarity	NPD1184	Approved
0.6912	Remote Similarity	NPD6666	Approved
0.6912	Remote Similarity	NPD6667	Approved
0.6911	Remote Similarity	NPD1091	Approved
0.6911	Remote Similarity	NPD776	Approved
0.6905	Remote Similarity	NPD7018	Phase 2
0.6899	Remote Similarity	NPD3058	Clinical (unspecified phase)

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