NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	208.07
Volume:	212.234
LogP:	1.675
LogD:	1.636
LogS:	-2.119
# Rotatable Bonds:	5
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.56
Synthetic Accessibility Score:	1.651
Fsp3:	0.273
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:	-4.584
MDCK Permeability:	3.591902714106254e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.378
30% Bioavailability (F30%):	0.251

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979
Plasma Protein Binding (PPB):	50.39250183105469%
Volume Distribution (VD):	0.492
Pgp-substrate:	71.05457305908203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.843
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.658
CYP2C19-substrate:	0.227
CYP2C9-inhibitor:	0.221
CYP2C9-substrate:	0.606
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.247
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	2.971
Half-life (T1/2):	0.867

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.777
AMES Toxicity:	0.286
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.052
Skin Sensitization:	0.812
Carcinogencity:	0.733
Eye Corrosion:	0.06
Eye Irritation:	0.956
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC291837

Natural Product ID:	NPC291837
*Common Name:**	(4-Acetyloxyphenyl)Methyl Acetate
IUPAC Name:	(4-acetyloxyphenyl)methyl acetate
Synonyms:	Acetic Acid 4-Acetoxymethyl-Phenyl Ester
Standard InCHIKey:	HUOJLQXKNCFOGC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H12O4/c1-8(12)14-7-10-3-5-11(6-4-10)15-9(2)13/h3-6H,7H2,1-2H3
SMILES:	CC(=O)OCc1ccc(cc1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL356415
PubChem CID:	470279
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
NPO11575	Artemisia japonica	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[11440075]
NPO11575	Artemisia japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11575	Artemisia japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11575	Artemisia japonica	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
MIC	2
Others	1

Activity Type	# Activity
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	8.0	ug.mL-1	PMID[543168]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	128.0	ug.mL-1	PMID[543168]
NPT35	Others	n.a.		LogP	=	2.03	n.a.	PMID[543168]

☑ 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 NPC291837 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	270
0.1-0.2	1661
0.2-0.3	5623
0.3-0.4	12473
0.4-0.5	5108
0.5-0.6	7685
0.6-0.7	8334
0.7-0.8	1434
0.8-0.85	77
0.85-0.9	17
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC231251
0.9804	High Similarity	NPC88868
0.9804	High Similarity	NPC25067
0.96	High Similarity	NPC283546
0.9505	High Similarity	NPC238115
0.9314	High Similarity	NPC473855
0.93	High Similarity	NPC107101
0.9252	High Similarity	NPC235250
0.9208	High Similarity	NPC307425
0.9126	High Similarity	NPC128730
0.9038	High Similarity	NPC176971
0.8952	High Similarity	NPC157473
0.8952	High Similarity	NPC151530
0.8942	High Similarity	NPC473393
0.8932	High Similarity	NPC179686
0.8919	High Similarity	NPC101503
0.885	High Similarity	NPC163200
0.885	High Similarity	NPC267064
0.8846	High Similarity	NPC109637
0.8839	High Similarity	NPC281356
0.8839	High Similarity	NPC298796
0.8785	High Similarity	NPC259554
0.8762	High Similarity	NPC8302
0.875	High Similarity	NPC152306
0.875	High Similarity	NPC96705
0.875	High Similarity	NPC265547
0.8684	High Similarity	NPC180006
0.8684	High Similarity	NPC235190
0.8679	High Similarity	NPC326447
0.8636	High Similarity	NPC303522
0.8624	High Similarity	NPC245552
0.8611	High Similarity	NPC149545
0.8596	High Similarity	NPC473290
0.8596	High Similarity	NPC471504
0.8571	High Similarity	NPC305205
0.8571	High Similarity	NPC128633
0.8505	High Similarity	NPC1065
0.8496	Intermediate Similarity	NPC471503
0.8496	Intermediate Similarity	NPC471498
0.8491	Intermediate Similarity	NPC108875
0.8491	Intermediate Similarity	NPC2518
0.8491	Intermediate Similarity	NPC38079
0.8476	Intermediate Similarity	NPC51633
0.8462	Intermediate Similarity	NPC109675
0.8462	Intermediate Similarity	NPC273772
0.8462	Intermediate Similarity	NPC279379
0.8462	Intermediate Similarity	NPC315807
0.8462	Intermediate Similarity	NPC471576
0.8462	Intermediate Similarity	NPC472518
0.8448	Intermediate Similarity	NPC144418
0.8421	Intermediate Similarity	NPC293424
0.8421	Intermediate Similarity	NPC159916
0.8416	Intermediate Similarity	NPC321956
0.8411	Intermediate Similarity	NPC470393
0.8411	Intermediate Similarity	NPC139891
0.84	Intermediate Similarity	NPC8002
0.84	Intermediate Similarity	NPC177844
0.84	Intermediate Similarity	NPC259134
0.84	Intermediate Similarity	NPC99886
0.8396	Intermediate Similarity	NPC192596
0.839	Intermediate Similarity	NPC27671
0.839	Intermediate Similarity	NPC201667
0.839	Intermediate Similarity	NPC73413
0.8381	Intermediate Similarity	NPC13755
0.8378	Intermediate Similarity	NPC115379
0.8376	Intermediate Similarity	NPC69403
0.8376	Intermediate Similarity	NPC248429
0.8376	Intermediate Similarity	NPC291189
0.8376	Intermediate Similarity	NPC96286
0.8365	Intermediate Similarity	NPC175298
0.8364	Intermediate Similarity	NPC106141
0.8333	Intermediate Similarity	NPC121740
0.8333	Intermediate Similarity	NPC224774
0.8333	Intermediate Similarity	NPC258567
0.8319	Intermediate Similarity	NPC220540
0.8317	Intermediate Similarity	NPC71853
0.8305	Intermediate Similarity	NPC154176
0.8305	Intermediate Similarity	NPC173350
0.8305	Intermediate Similarity	NPC290605
0.8291	Intermediate Similarity	NPC187868
0.8291	Intermediate Similarity	NPC52247
0.8286	Intermediate Similarity	NPC100870
0.8286	Intermediate Similarity	NPC171843
0.8273	Intermediate Similarity	NPC234639
0.8264	Intermediate Similarity	NPC199204
0.8264	Intermediate Similarity	NPC472519
0.8264	Intermediate Similarity	NPC469453
0.8261	Intermediate Similarity	NPC124916
0.8257	Intermediate Similarity	NPC251306
0.825	Intermediate Similarity	NPC127604
0.825	Intermediate Similarity	NPC188327
0.825	Intermediate Similarity	NPC475236
0.825	Intermediate Similarity	NPC101894
0.825	Intermediate Similarity	NPC234109
0.8241	Intermediate Similarity	NPC227255
0.8235	Intermediate Similarity	NPC221798
0.823	Intermediate Similarity	NPC87563
0.823	Intermediate Similarity	NPC161696
0.8224	Intermediate Similarity	NPC298224
0.822	Intermediate Similarity	NPC13007
0.822	Intermediate Similarity	NPC257188
0.8214	Intermediate Similarity	NPC280760
0.8205	Intermediate Similarity	NPC302107
0.8205	Intermediate Similarity	NPC319378
0.8198	Intermediate Similarity	NPC473809
0.8197	Intermediate Similarity	NPC168710
0.819	Intermediate Similarity	NPC98748
0.819	Intermediate Similarity	NPC95755
0.819	Intermediate Similarity	NPC37858
0.8167	Intermediate Similarity	NPC471827
0.8167	Intermediate Similarity	NPC471828
0.8158	Intermediate Similarity	NPC51345
0.8158	Intermediate Similarity	NPC296526
0.8148	Intermediate Similarity	NPC38209
0.8142	Intermediate Similarity	NPC90903
0.8142	Intermediate Similarity	NPC301735
0.8131	Intermediate Similarity	NPC84325
0.813	Intermediate Similarity	NPC113098
0.813	Intermediate Similarity	NPC19242
0.813	Intermediate Similarity	NPC80170
0.8125	Intermediate Similarity	NPC233238
0.812	Intermediate Similarity	NPC31314
0.812	Intermediate Similarity	NPC247553
0.812	Intermediate Similarity	NPC193193
0.8115	Intermediate Similarity	NPC474651
0.8115	Intermediate Similarity	NPC474623
0.8115	Intermediate Similarity	NPC210674
0.8115	Intermediate Similarity	NPC185066
0.8099	Intermediate Similarity	NPC471826
0.8091	Intermediate Similarity	NPC258171
0.8087	Intermediate Similarity	NPC470860
0.8083	Intermediate Similarity	NPC111347
0.8077	Intermediate Similarity	NPC471581
0.8073	Intermediate Similarity	NPC127676
0.8073	Intermediate Similarity	NPC288760
0.8067	Intermediate Similarity	NPC288238
0.8065	Intermediate Similarity	NPC272650
0.8065	Intermediate Similarity	NPC29734
0.8065	Intermediate Similarity	NPC267336
0.8056	Intermediate Similarity	NPC304638
0.8053	Intermediate Similarity	NPC199462
0.8051	Intermediate Similarity	NPC322569
0.8036	Intermediate Similarity	NPC141068
0.8036	Intermediate Similarity	NPC46844
0.8034	Intermediate Similarity	NPC264976
0.8034	Intermediate Similarity	NPC59561
0.8034	Intermediate Similarity	NPC61779
0.8034	Intermediate Similarity	NPC172253
0.8033	Intermediate Similarity	NPC194841
0.8017	Intermediate Similarity	NPC244495
0.8017	Intermediate Similarity	NPC165556
0.8017	Intermediate Similarity	NPC93219
0.8017	Intermediate Similarity	NPC168259
0.8	Intermediate Similarity	NPC50720
0.8	Intermediate Similarity	NPC470887
0.8	Intermediate Similarity	NPC194277
0.8	Intermediate Similarity	NPC322358
0.8	Intermediate Similarity	NPC14248
0.8	Intermediate Similarity	NPC137669
0.8	Intermediate Similarity	NPC175159
0.7984	Intermediate Similarity	NPC244799
0.7984	Intermediate Similarity	NPC476399
0.7984	Intermediate Similarity	NPC240722
0.7984	Intermediate Similarity	NPC307042
0.7984	Intermediate Similarity	NPC79184
0.7982	Intermediate Similarity	NPC109241
0.7966	Intermediate Similarity	NPC230951
0.7966	Intermediate Similarity	NPC222175
0.7963	Intermediate Similarity	NPC300166
0.7949	Intermediate Similarity	NPC277460
0.7937	Intermediate Similarity	NPC469449
0.7937	Intermediate Similarity	NPC471910
0.7937	Intermediate Similarity	NPC318400
0.7937	Intermediate Similarity	NPC133956
0.7937	Intermediate Similarity	NPC36437
0.7937	Intermediate Similarity	NPC233018
0.7937	Intermediate Similarity	NPC296624
0.7937	Intermediate Similarity	NPC7526
0.7937	Intermediate Similarity	NPC207002
0.7937	Intermediate Similarity	NPC163557
0.7937	Intermediate Similarity	NPC167111
0.7937	Intermediate Similarity	NPC31849
0.7937	Intermediate Similarity	NPC2363
0.7937	Intermediate Similarity	NPC241341
0.7937	Intermediate Similarity	NPC222036
0.7934	Intermediate Similarity	NPC140521
0.7934	Intermediate Similarity	NPC291899
0.7931	Intermediate Similarity	NPC33717
0.7928	Intermediate Similarity	NPC194034
0.792	Intermediate Similarity	NPC472517
0.792	Intermediate Similarity	NPC250727
0.7917	Intermediate Similarity	NPC150214
0.7913	Intermediate Similarity	NPC252004
0.7913	Intermediate Similarity	NPC294941
0.7903	Intermediate Similarity	NPC123127
0.7903	Intermediate Similarity	NPC27239
0.7903	Intermediate Similarity	NPC295970
0.7903	Intermediate Similarity	NPC474289
0.79	Intermediate Similarity	NPC58616
0.7899	Intermediate Similarity	NPC269242

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 NPC291837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	1033
0.2-0.3	1730
0.3-0.4	2622
0.4-0.5	1743
0.5-0.6	1093
0.6-0.7	572
0.7-0.8	118
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
0.8774	High Similarity	NPD1358	Approved
0.8716	High Similarity	NPD5535	Approved
0.8679	High Similarity	NPD3134	Approved
0.8411	Intermediate Similarity	NPD9697	Approved
0.8291	Intermediate Similarity	NPD422	Phase 1
0.8182	Intermediate Similarity	NPD2684	Approved
0.8142	Intermediate Similarity	NPD1241	Discontinued
0.812	Intermediate Similarity	NPD1778	Approved
0.8053	Intermediate Similarity	NPD7843	Approved
0.7984	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD17	Approved
0.7949	Intermediate Similarity	NPD1894	Discontinued
0.7928	Intermediate Similarity	NPD290	Approved
0.7899	Intermediate Similarity	NPD3496	Discontinued
0.7895	Intermediate Similarity	NPD821	Approved
0.7881	Intermediate Similarity	NPD5691	Approved
0.7881	Intermediate Similarity	NPD5585	Approved
0.7845	Intermediate Similarity	NPD7157	Approved
0.7838	Intermediate Similarity	NPD968	Approved
0.7797	Intermediate Similarity	NPD1548	Phase 1
0.7797	Intermediate Similarity	NPD9545	Approved
0.7769	Intermediate Similarity	NPD1608	Approved
0.7698	Intermediate Similarity	NPD1296	Phase 2
0.7686	Intermediate Similarity	NPD1535	Discovery
0.7686	Intermediate Similarity	NPD1611	Approved
0.7661	Intermediate Similarity	NPD1019	Discontinued
0.7656	Intermediate Similarity	NPD4340	Discontinued
0.7642	Intermediate Similarity	NPD3225	Approved
0.7623	Intermediate Similarity	NPD9717	Approved
0.7623	Intermediate Similarity	NPD1481	Phase 2
0.7619	Intermediate Similarity	NPD5746	Approved
0.7603	Intermediate Similarity	NPD3847	Discontinued
0.7561	Intermediate Similarity	NPD4359	Approved
0.7559	Intermediate Similarity	NPD6798	Discontinued
0.7541	Intermediate Similarity	NPD3705	Approved
0.7541	Intermediate Similarity	NPD1610	Phase 2
0.7541	Intermediate Similarity	NPD1091	Approved
0.754	Intermediate Similarity	NPD6832	Phase 2
0.7521	Intermediate Similarity	NPD4626	Approved
0.7519	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5124	Phase 1
0.7519	Intermediate Similarity	NPD1652	Phase 2
0.75	Intermediate Similarity	NPD5745	Approved
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD4062	Phase 3
0.748	Intermediate Similarity	NPD5163	Phase 2
0.7479	Intermediate Similarity	NPD3596	Phase 2
0.7478	Intermediate Similarity	NPD5451	Approved
0.746	Intermediate Similarity	NPD454	Approved
0.7453	Intermediate Similarity	NPD9365	Approved
0.7442	Intermediate Similarity	NPD4140	Approved
0.7442	Intermediate Similarity	NPD4060	Phase 1
0.744	Intermediate Similarity	NPD987	Approved
0.744	Intermediate Similarity	NPD3267	Approved
0.744	Intermediate Similarity	NPD3266	Approved
0.7422	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3685	Discontinued
0.7402	Intermediate Similarity	NPD4908	Phase 1
0.7402	Intermediate Similarity	NPD2614	Approved
0.7398	Intermediate Similarity	NPD1281	Approved
0.7388	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD6355	Discontinued
0.7373	Intermediate Similarity	NPD5283	Phase 1
0.736	Intermediate Similarity	NPD8651	Approved
0.7355	Intermediate Similarity	NPD6580	Approved
0.7355	Intermediate Similarity	NPD1182	Approved
0.7355	Intermediate Similarity	NPD6581	Approved
0.735	Intermediate Similarity	NPD228	Approved
0.7348	Intermediate Similarity	NPD7033	Discontinued
0.7344	Intermediate Similarity	NPD7095	Approved
0.7344	Intermediate Similarity	NPD3179	Approved
0.7344	Intermediate Similarity	NPD3180	Approved
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7323	Intermediate Similarity	NPD2237	Approved
0.7302	Intermediate Similarity	NPD6362	Approved
0.7302	Intermediate Similarity	NPD1203	Approved
0.7302	Intermediate Similarity	NPD2797	Approved
0.7295	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD769	Approved
0.7287	Intermediate Similarity	NPD1048	Approved
0.7287	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5536	Phase 2
0.7273	Intermediate Similarity	NPD7097	Phase 1
0.7252	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2557	Approved
0.7236	Intermediate Similarity	NPD6516	Phase 2
0.7236	Intermediate Similarity	NPD5846	Approved
0.7231	Intermediate Similarity	NPD8032	Phase 2
0.7227	Intermediate Similarity	NPD594	Approved
0.7227	Intermediate Similarity	NPD592	Approved
0.7226	Intermediate Similarity	NPD6666	Approved
0.7226	Intermediate Similarity	NPD6667	Approved
0.7222	Intermediate Similarity	NPD1283	Approved
0.7218	Intermediate Similarity	NPD3748	Approved
0.7203	Intermediate Similarity	NPD1139	Approved
0.7203	Intermediate Similarity	NPD1137	Approved
0.7197	Intermediate Similarity	NPD2653	Approved
0.7194	Intermediate Similarity	NPD2186	Approved
0.7188	Intermediate Similarity	NPD2861	Phase 2
0.7176	Intermediate Similarity	NPD2979	Phase 3
0.7174	Intermediate Similarity	NPD6799	Approved
0.7168	Intermediate Similarity	NPD291	Approved
0.7164	Intermediate Similarity	NPD2239	Approved
0.7164	Intermediate Similarity	NPD2240	Approved
0.7164	Intermediate Similarity	NPD1551	Phase 2
0.7154	Intermediate Similarity	NPD1651	Approved
0.7154	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD5327	Phase 3
0.7143	Intermediate Similarity	NPD6583	Phase 3
0.7143	Intermediate Similarity	NPD1138	Approved
0.7143	Intermediate Similarity	NPD6582	Phase 2
0.7122	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3146	Approved
0.712	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5762	Approved
0.7111	Intermediate Similarity	NPD6002	Phase 3
0.7111	Intermediate Similarity	NPD5763	Approved
0.7111	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6004	Phase 3
0.7111	Intermediate Similarity	NPD6005	Phase 3
0.7111	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD5647	Approved
0.7107	Intermediate Similarity	NPD6671	Approved
0.7099	Intermediate Similarity	NPD4870	Approved
0.7092	Intermediate Similarity	NPD3687	Approved
0.7092	Intermediate Similarity	NPD3686	Approved
0.7087	Intermediate Similarity	NPD196	Phase 1
0.7075	Intermediate Similarity	NPD1282	Approved
0.7071	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6653	Approved
0.7063	Intermediate Similarity	NPD1840	Phase 2
0.7063	Intermediate Similarity	NPD2981	Phase 2
0.7048	Intermediate Similarity	NPD111	Approved
0.7045	Intermediate Similarity	NPD1613	Approved
0.7045	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4307	Phase 2
0.7042	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4476	Approved
0.7037	Intermediate Similarity	NPD4477	Approved
0.7037	Intermediate Similarity	NPD2796	Approved
0.7031	Intermediate Similarity	NPD3567	Approved
0.7031	Intermediate Similarity	NPD1819	Approved
0.7031	Intermediate Similarity	NPD3568	Approved
0.7031	Intermediate Similarity	NPD1820	Approved
0.7031	Intermediate Similarity	NPD1817	Approved
0.7031	Intermediate Similarity	NPD1818	Approved
0.7023	Intermediate Similarity	NPD411	Approved
0.7021	Intermediate Similarity	NPD920	Approved
0.7016	Intermediate Similarity	NPD3049	Approved
0.7016	Intermediate Similarity	NPD3444	Approved
0.7016	Intermediate Similarity	NPD6382	Discontinued
0.7016	Intermediate Similarity	NPD1357	Approved
0.7016	Intermediate Similarity	NPD3443	Approved
0.7016	Intermediate Similarity	NPD3445	Approved
0.7008	Intermediate Similarity	NPD2982	Phase 2
0.7008	Intermediate Similarity	NPD6543	Approved
0.7008	Intermediate Similarity	NPD6540	Phase 3
0.7008	Intermediate Similarity	NPD6542	Approved
0.7008	Intermediate Similarity	NPD2983	Phase 2
0.7008	Intermediate Similarity	NPD2428	Approved
0.7008	Intermediate Similarity	NPD6539	Approved
0.7008	Intermediate Similarity	NPD2429	Approved
0.7007	Intermediate Similarity	NPD1243	Approved
0.7	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3536	Discontinued
0.6992	Remote Similarity	NPD4618	Approved
0.6992	Remote Similarity	NPD1933	Approved
0.6992	Remote Similarity	NPD447	Suspended
0.6992	Remote Similarity	NPD4622	Approved
0.6985	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1375	Discontinued
0.6985	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6584	Phase 3
0.6977	Remote Similarity	NPD3690	Phase 2
0.6977	Remote Similarity	NPD3691	Phase 2
0.6972	Remote Similarity	NPD1653	Approved
0.697	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2799	Discontinued
0.696	Remote Similarity	NPD2554	Approved
0.696	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.696	Remote Similarity	NPD2556	Approved
0.6957	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4110	Phase 3
0.6957	Remote Similarity	NPD3750	Approved
0.6953	Remote Similarity	NPD6541	Approved
0.6953	Remote Similarity	NPD6538	Approved
0.695	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3027	Phase 3
0.6947	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD9295	Approved
0.6937	Remote Similarity	NPD2933	Approved
0.6937	Remote Similarity	NPD2934	Approved
0.6934	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1549	Phase 2
0.6934	Remote Similarity	NPD4534	Discontinued
0.6929	Remote Similarity	NPD3972	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