NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	272.628
LogP:	3.941
LogD:	3.415
LogS:	-4.091
# Rotatable Bonds:	7
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.573
Synthetic Accessibility Score:	2.008
Fsp3:	0.4
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:	-4.448
MDCK Permeability:	2.7041820430895314e-05
Pgp-inhibitor:	0.347
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.366
30% Bioavailability (F30%):	0.871

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.458
Plasma Protein Binding (PPB):	92.92890167236328%
Volume Distribution (VD):	2.309
Pgp-substrate:	8.156064987182617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.142
CYP2C19-inhibitor:	0.934
CYP2C19-substrate:	0.176
CYP2C9-inhibitor:	0.835
CYP2C9-substrate:	0.738
CYP2D6-inhibitor:	0.554
CYP2D6-substrate:	0.641
CYP3A4-inhibitor:	0.274
CYP3A4-substrate:	0.449

ADMET: Excretion

Clearance (CL):	11.998
Half-life (T1/2):	0.338

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.87
Drug-inuced Liver Injury (DILI):	0.59
AMES Toxicity:	0.565
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.867
Carcinogencity:	0.462
Eye Corrosion:	0.005
Eye Irritation:	0.864
Respiratory Toxicity:	0.077

Download Data

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

Natural Product: NPC473855

Natural Product ID:	NPC473855
*Common Name:**	Etrogol Acetate
IUPAC Name:	2-[4-(3-methylbut-2-enoxy)phenyl]ethyl acetate
Synonyms:	Etrogol Acetate
Standard InCHIKey:	FBZRYCBQRHKYRY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-12(2)8-10-18-15-6-4-14(5-7-15)9-11-17-13(3)16/h4-8H,9-11H2,1-3H3
SMILES:	CC(=O)OCCc1ccc(cc1)OCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453556
PubChem CID:	11807011
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000139] Tyrosols 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
NPO7651	Citrus spp.	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22472691]
NPO7651	Citrus spp.	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	8

Activity Type	# Activity
Individual Protein	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1778	Individual Protein	Serotonin 2a (5-HT2a) receptor	Rattus norvegicus	Activity	=	11.0	%	PMID[545040]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.857	n.a.	PMID[545041]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.899	n.a.	PMID[545041]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.786	n.a.	PMID[545041]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.022	n.a.	PMID[545041]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.079	n.a.	PMID[545041]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.021	n.a.	PMID[545041]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.304	n.a.	PMID[545041]

☑ 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 NPC473855 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	1522
0.2-0.3	5141
0.3-0.4	12666
0.4-0.5	5400
0.5-0.6	8338
0.6-0.7	7879
0.7-0.8	1378
0.8-0.85	82
0.85-0.9	30
0.9-0.95	19
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC176971
0.9495	High Similarity	NPC283546
0.949	High Similarity	NPC307425
0.9406	High Similarity	NPC151530
0.9406	High Similarity	NPC157473
0.94	High Similarity	NPC128730
0.9388	High Similarity	NPC107101
0.932	High Similarity	NPC88868
0.932	High Similarity	NPC231251
0.932	High Similarity	NPC25067
0.9314	High Similarity	NPC291837
0.9208	High Similarity	NPC473393
0.9208	High Similarity	NPC238115
0.92	High Similarity	NPC179686
0.9118	High Similarity	NPC326447
0.9109	High Similarity	NPC108875
0.9109	High Similarity	NPC38079
0.9038	High Similarity	NPC259554
0.902	High Similarity	NPC470393
0.8972	High Similarity	NPC235250
0.8932	High Similarity	NPC1065
0.8922	High Similarity	NPC109637
0.8911	High Similarity	NPC51633
0.89	High Similarity	NPC471576
0.8879	High Similarity	NPC303522
0.8866	High Similarity	NPC321956
0.8824	High Similarity	NPC192596
0.8818	High Similarity	NPC293424
0.8774	High Similarity	NPC473809
0.8763	High Similarity	NPC71853
0.8738	High Similarity	NPC2518
0.8713	High Similarity	NPC100870
0.8692	High Similarity	NPC245552
0.8679	High Similarity	NPC149545
0.8679	High Similarity	NPC234639
0.866	High Similarity	NPC177844
0.866	High Similarity	NPC259134
0.866	High Similarity	NPC99886
0.866	High Similarity	NPC8002
0.8641	High Similarity	NPC298224
0.8627	High Similarity	NPC13755
0.8614	High Similarity	NPC95755
0.8614	High Similarity	NPC175298
0.8611	High Similarity	NPC280760
0.8611	High Similarity	NPC199462
0.8584	High Similarity	NPC267064
0.8558	High Similarity	NPC38209
0.8545	High Similarity	NPC51345
0.8529	High Similarity	NPC171843
0.85	High Similarity	NPC471581
0.8491	Intermediate Similarity	NPC258171
0.8482	Intermediate Similarity	NPC159916
0.8482	Intermediate Similarity	NPC96705
0.8482	Intermediate Similarity	NPC101503
0.8476	Intermediate Similarity	NPC8302
0.8476	Intermediate Similarity	NPC139891
0.8476	Intermediate Similarity	NPC227255
0.8421	Intermediate Similarity	NPC180006
0.8421	Intermediate Similarity	NPC163200
0.8421	Intermediate Similarity	NPC235190
0.8407	Intermediate Similarity	NPC37858
0.8407	Intermediate Similarity	NPC98748
0.8407	Intermediate Similarity	NPC281356
0.8393	Intermediate Similarity	NPC183154
0.8393	Intermediate Similarity	NPC263754
0.8378	Intermediate Similarity	NPC296526
0.8365	Intermediate Similarity	NPC84325
0.8365	Intermediate Similarity	NPC300166
0.8364	Intermediate Similarity	NPC90903
0.8364	Intermediate Similarity	NPC109241
0.8362	Intermediate Similarity	NPC279379
0.8349	Intermediate Similarity	NPC233238
0.8333	Intermediate Similarity	NPC473290
0.8333	Intermediate Similarity	NPC471504
0.8319	Intermediate Similarity	NPC265547
0.8304	Intermediate Similarity	NPC470860
0.8302	Intermediate Similarity	NPC288760
0.8288	Intermediate Similarity	NPC87563
0.8286	Intermediate Similarity	NPC304638
0.8286	Intermediate Similarity	NPC305205
0.8276	Intermediate Similarity	NPC248429
0.8276	Intermediate Similarity	NPC96286
0.8265	Intermediate Similarity	NPC304760
0.8261	Intermediate Similarity	NPC322569
0.8257	Intermediate Similarity	NPC46844
0.8252	Intermediate Similarity	NPC470161
0.8246	Intermediate Similarity	NPC264976
0.8246	Intermediate Similarity	NPC298796
0.8246	Intermediate Similarity	NPC234956
0.823	Intermediate Similarity	NPC471498
0.823	Intermediate Similarity	NPC471503
0.8224	Intermediate Similarity	NPC326801
0.8224	Intermediate Similarity	NPC113457
0.8208	Intermediate Similarity	NPC292792
0.8205	Intermediate Similarity	NPC470887
0.8205	Intermediate Similarity	NPC472518
0.8198	Intermediate Similarity	NPC26524
0.8182	Intermediate Similarity	NPC55300
0.8174	Intermediate Similarity	NPC31314
0.8174	Intermediate Similarity	NPC193193
0.8165	Intermediate Similarity	NPC474272
0.8158	Intermediate Similarity	NPC277460
0.8158	Intermediate Similarity	NPC124916
0.8158	Intermediate Similarity	NPC152306
0.8151	Intermediate Similarity	NPC474476
0.8148	Intermediate Similarity	NPC194034
0.8148	Intermediate Similarity	NPC251306
0.8144	Intermediate Similarity	NPC58616
0.8142	Intermediate Similarity	NPC128633
0.8142	Intermediate Similarity	NPC33717
0.8136	Intermediate Similarity	NPC221798
0.8136	Intermediate Similarity	NPC73413
0.8136	Intermediate Similarity	NPC201667
0.8131	Intermediate Similarity	NPC127676
0.8125	Intermediate Similarity	NPC252004
0.812	Intermediate Similarity	NPC69403
0.812	Intermediate Similarity	NPC291189
0.8108	Intermediate Similarity	NPC115379
0.8108	Intermediate Similarity	NPC165646
0.8095	Intermediate Similarity	NPC253746
0.8091	Intermediate Similarity	NPC141068
0.8091	Intermediate Similarity	NPC183700
0.8091	Intermediate Similarity	NPC137685
0.8091	Intermediate Similarity	NPC106141
0.8073	Intermediate Similarity	NPC75440
0.8073	Intermediate Similarity	NPC206341
0.8073	Intermediate Similarity	NPC31274
0.8053	Intermediate Similarity	NPC220540
0.8051	Intermediate Similarity	NPC273772
0.8051	Intermediate Similarity	NPC315807
0.8051	Intermediate Similarity	NPC21238
0.8051	Intermediate Similarity	NPC109675
0.8037	Intermediate Similarity	NPC241224
0.8034	Intermediate Similarity	NPC52247
0.8019	Intermediate Similarity	NPC310905
0.8019	Intermediate Similarity	NPC12714
0.8018	Intermediate Similarity	NPC23332
0.8018	Intermediate Similarity	NPC139946
0.8017	Intermediate Similarity	NPC472519
0.8017	Intermediate Similarity	NPC474874
0.8017	Intermediate Similarity	NPC210674
0.8	Intermediate Similarity	NPC220893
0.8	Intermediate Similarity	NPC205502
0.8	Intermediate Similarity	NPC75272
0.8	Intermediate Similarity	NPC471954
0.8	Intermediate Similarity	NPC132725
0.8	Intermediate Similarity	NPC101894
0.8	Intermediate Similarity	NPC234109
0.8	Intermediate Similarity	NPC188327
0.7983	Intermediate Similarity	NPC60517
0.7983	Intermediate Similarity	NPC146886
0.7983	Intermediate Similarity	NPC89630
0.7983	Intermediate Similarity	NPC27671
0.7983	Intermediate Similarity	NPC20443
0.7982	Intermediate Similarity	NPC260952
0.798	Intermediate Similarity	NPC89377
0.7965	Intermediate Similarity	NPC294941
0.7965	Intermediate Similarity	NPC161696
0.7951	Intermediate Similarity	NPC170546
0.7951	Intermediate Similarity	NPC66246
0.7951	Intermediate Similarity	NPC168710
0.7949	Intermediate Similarity	NPC204466
0.7946	Intermediate Similarity	NPC266116
0.7944	Intermediate Similarity	NPC24327
0.7944	Intermediate Similarity	NPC12870
0.7934	Intermediate Similarity	NPC224774
0.7934	Intermediate Similarity	NPC121740
0.7934	Intermediate Similarity	NPC473993
0.7934	Intermediate Similarity	NPC258567
0.7931	Intermediate Similarity	NPC172253
0.7931	Intermediate Similarity	NPC59561
0.7928	Intermediate Similarity	NPC179309
0.7928	Intermediate Similarity	NPC63345
0.7928	Intermediate Similarity	NPC475852
0.7928	Intermediate Similarity	NPC183648
0.7917	Intermediate Similarity	NPC85830
0.7917	Intermediate Similarity	NPC170749
0.7917	Intermediate Similarity	NPC471827
0.7917	Intermediate Similarity	NPC280767
0.7917	Intermediate Similarity	NPC471828
0.7913	Intermediate Similarity	NPC217423
0.7913	Intermediate Similarity	NPC45104
0.7909	Intermediate Similarity	NPC201959
0.7899	Intermediate Similarity	NPC320287
0.7895	Intermediate Similarity	NPC322358
0.7886	Intermediate Similarity	NPC476399
0.7886	Intermediate Similarity	NPC307042
0.7886	Intermediate Similarity	NPC79184
0.7886	Intermediate Similarity	NPC80170
0.7886	Intermediate Similarity	NPC282230
0.7886	Intermediate Similarity	NPC183348
0.7881	Intermediate Similarity	NPC70752
0.7881	Intermediate Similarity	NPC187868
0.7881	Intermediate Similarity	NPC144418
0.7881	Intermediate Similarity	NPC114845
0.7876	Intermediate Similarity	NPC301735
0.787	Intermediate Similarity	NPC12987
0.787	Intermediate Similarity	NPC474603
0.7869	Intermediate Similarity	NPC199204
0.7869	Intermediate Similarity	NPC469453

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 NPC473855 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	1054
0.2-0.3	1466
0.3-0.4	2569
0.4-0.5	1886
0.5-0.6	1140
0.6-0.7	620
0.7-0.8	185
0.8-0.85	9
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9118	High Similarity	NPD3134	Approved
0.9029	High Similarity	NPD1358	Approved
0.8962	High Similarity	NPD5535	Approved
0.8762	High Similarity	NPD2684	Approved
0.8532	High Similarity	NPD1241	Discontinued
0.8476	Intermediate Similarity	NPD9697	Approved
0.844	Intermediate Similarity	NPD821	Approved
0.844	Intermediate Similarity	NPD7843	Approved
0.8407	Intermediate Similarity	NPD5691	Approved
0.8319	Intermediate Similarity	NPD1894	Discontinued
0.8261	Intermediate Similarity	NPD3496	Discontinued
0.8246	Intermediate Similarity	NPD5585	Approved
0.8214	Intermediate Similarity	NPD7157	Approved
0.8174	Intermediate Similarity	NPD1778	Approved
0.8148	Intermediate Similarity	NPD290	Approved
0.8056	Intermediate Similarity	NPD968	Approved
0.8034	Intermediate Similarity	NPD422	Phase 1
0.8017	Intermediate Similarity	NPD4626	Approved
0.8	Intermediate Similarity	NPD5451	Approved
0.7982	Intermediate Similarity	NPD3596	Phase 2
0.7951	Intermediate Similarity	NPD5163	Phase 2
0.7951	Intermediate Similarity	NPD5746	Approved
0.7949	Intermediate Similarity	NPD3847	Discontinued
0.7899	Intermediate Similarity	NPD4359	Approved
0.7886	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD6798	Discontinued
0.7881	Intermediate Similarity	NPD1535	Discovery
0.7863	Intermediate Similarity	NPD17	Approved
0.7845	Intermediate Similarity	NPD6580	Approved
0.7845	Intermediate Similarity	NPD6581	Approved
0.7823	Intermediate Similarity	NPD6233	Phase 2
0.7823	Intermediate Similarity	NPD5745	Approved
0.7823	Intermediate Similarity	NPD4062	Phase 3
0.7815	Intermediate Similarity	NPD1481	Phase 2
0.7787	Intermediate Similarity	NPD454	Approved
0.7778	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD987	Approved
0.776	Intermediate Similarity	NPD4140	Approved
0.776	Intermediate Similarity	NPD4060	Phase 1
0.775	Intermediate Similarity	NPD3685	Discontinued
0.7739	Intermediate Similarity	NPD2557	Approved
0.7731	Intermediate Similarity	NPD1281	Approved
0.7731	Intermediate Similarity	NPD1611	Approved
0.7724	Intermediate Similarity	NPD6832	Phase 2
0.7719	Intermediate Similarity	NPD5283	Phase 1
0.7712	Intermediate Similarity	NPD5846	Approved
0.7712	Intermediate Similarity	NPD6516	Phase 2
0.7699	Intermediate Similarity	NPD228	Approved
0.7698	Intermediate Similarity	NPD6355	Discontinued
0.7692	Intermediate Similarity	NPD1548	Phase 1
0.767	Intermediate Similarity	NPD9365	Approved
0.7667	Intermediate Similarity	NPD1608	Approved
0.7661	Intermediate Similarity	NPD7095	Approved
0.7642	Intermediate Similarity	NPD2237	Approved
0.7627	Intermediate Similarity	NPD1651	Approved
0.7623	Intermediate Similarity	NPD2797	Approved
0.7623	Intermediate Similarity	NPD6362	Approved
0.7603	Intermediate Similarity	NPD6583	Phase 3
0.7603	Intermediate Similarity	NPD5327	Phase 3
0.7603	Intermediate Similarity	NPD6582	Phase 2
0.7586	Intermediate Similarity	NPD6671	Approved
0.7581	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD2614	Approved
0.7578	Intermediate Similarity	NPD7097	Phase 1
0.7565	Intermediate Similarity	NPD594	Approved
0.7565	Intermediate Similarity	NPD592	Approved
0.7561	Intermediate Similarity	NPD1019	Discontinued
0.7559	Intermediate Similarity	NPD4340	Discontinued
0.7544	Intermediate Similarity	NPD1137	Approved
0.7544	Intermediate Similarity	NPD1139	Approved
0.7542	Intermediate Similarity	NPD9545	Approved
0.7542	Intermediate Similarity	NPD1182	Approved
0.7541	Intermediate Similarity	NPD1283	Approved
0.754	Intermediate Similarity	NPD4870	Approved
0.754	Intermediate Similarity	NPD8032	Phase 2
0.7521	Intermediate Similarity	NPD9717	Approved
0.748	Intermediate Similarity	NPD2979	Phase 3
0.748	Intermediate Similarity	NPD1820	Approved
0.748	Intermediate Similarity	NPD1818	Approved
0.748	Intermediate Similarity	NPD3266	Approved
0.748	Intermediate Similarity	NPD1819	Approved
0.748	Intermediate Similarity	NPD3267	Approved
0.748	Intermediate Similarity	NPD1817	Approved
0.7479	Intermediate Similarity	NPD3445	Approved
0.7479	Intermediate Similarity	NPD3444	Approved
0.7479	Intermediate Similarity	NPD3443	Approved
0.7479	Intermediate Similarity	NPD3049	Approved
0.7478	Intermediate Similarity	NPD1138	Approved
0.7478	Intermediate Similarity	NPD769	Approved
0.7462	Intermediate Similarity	NPD2240	Approved
0.7462	Intermediate Similarity	NPD2239	Approved
0.7462	Intermediate Similarity	NPD4476	Approved
0.7462	Intermediate Similarity	NPD4477	Approved
0.746	Intermediate Similarity	NPD1048	Approved
0.7459	Intermediate Similarity	NPD6543	Approved
0.7459	Intermediate Similarity	NPD6540	Phase 3
0.7459	Intermediate Similarity	NPD2429	Approved
0.7459	Intermediate Similarity	NPD2428	Approved
0.7459	Intermediate Similarity	NPD6539	Approved
0.7459	Intermediate Similarity	NPD6542	Approved
0.7458	Intermediate Similarity	NPD5536	Phase 2
0.7453	Intermediate Similarity	NPD2934	Approved
0.7453	Intermediate Similarity	NPD2933	Approved
0.7438	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3705	Approved
0.7438	Intermediate Similarity	NPD1610	Phase 2
0.7422	Intermediate Similarity	NPD4622	Approved
0.7422	Intermediate Similarity	NPD4618	Approved
0.7419	Intermediate Similarity	NPD6584	Phase 3
0.7419	Intermediate Similarity	NPD3690	Phase 2
0.7419	Intermediate Similarity	NPD3691	Phase 2
0.7419	Intermediate Similarity	NPD5647	Approved
0.7417	Intermediate Similarity	NPD2556	Approved
0.7417	Intermediate Similarity	NPD2554	Approved
0.7405	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6541	Approved
0.7398	Intermediate Similarity	NPD6538	Approved
0.7398	Intermediate Similarity	NPD196	Phase 1
0.7383	Intermediate Similarity	NPD2860	Approved
0.7383	Intermediate Similarity	NPD2859	Approved
0.7377	Intermediate Similarity	NPD3972	Approved
0.7377	Intermediate Similarity	NPD1840	Phase 2
0.7364	Intermediate Similarity	NPD2653	Approved
0.7364	Intermediate Similarity	NPD6653	Approved
0.7348	Intermediate Similarity	NPD4534	Discontinued
0.7344	Intermediate Similarity	NPD3140	Approved
0.7344	Intermediate Similarity	NPD3142	Approved
0.7333	Intermediate Similarity	NPD6382	Discontinued
0.7333	Intermediate Similarity	NPD1357	Approved
0.7323	Intermediate Similarity	NPD1296	Phase 2
0.7323	Intermediate Similarity	NPD3268	Approved
0.7308	Intermediate Similarity	NPD5688	Approved
0.7308	Intermediate Similarity	NPD5689	Approved
0.7302	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4908	Phase 1
0.7295	Intermediate Similarity	NPD1091	Approved
0.7293	Intermediate Similarity	NPD1652	Phase 2
0.7293	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5124	Phase 1
0.7282	Intermediate Similarity	NPD1282	Approved
0.728	Intermediate Similarity	NPD7018	Phase 2
0.7273	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2667	Approved
0.7273	Intermediate Similarity	NPD2668	Approved
0.7266	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8651	Approved
0.7258	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD3225	Approved
0.7255	Intermediate Similarity	NPD111	Approved
0.7252	Intermediate Similarity	NPD7033	Discontinued
0.7252	Intermediate Similarity	NPD2799	Discontinued
0.725	Intermediate Similarity	NPD2486	Discontinued
0.7244	Intermediate Similarity	NPD2598	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3165	Approved
0.7244	Intermediate Similarity	NPD3164	Approved
0.7244	Intermediate Similarity	NPD3167	Approved
0.7244	Intermediate Similarity	NPD3166	Approved
0.7239	Intermediate Similarity	NPD4110	Phase 3
0.7239	Intermediate Similarity	NPD4628	Phase 3
0.7239	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD2235	Phase 2
0.7236	Intermediate Similarity	NPD2231	Phase 2
0.7222	Intermediate Similarity	NPD2861	Phase 2
0.7218	Intermediate Similarity	NPD5958	Discontinued
0.7218	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD291	Approved
0.7203	Intermediate Similarity	NPD595	Approved
0.7203	Intermediate Similarity	NPD593	Approved
0.72	Intermediate Similarity	NPD1794	Approved
0.72	Intermediate Similarity	NPD1203	Approved
0.72	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4098	Discontinued
0.7197	Intermediate Similarity	NPD2438	Suspended
0.7197	Intermediate Similarity	NPD6032	Approved
0.7197	Intermediate Similarity	NPD2531	Phase 2
0.7193	Intermediate Similarity	NPD5373	Approved
0.7193	Intermediate Similarity	NPD5374	Approved
0.719	Intermediate Similarity	NPD2595	Approved
0.719	Intermediate Similarity	NPD2594	Approved
0.7188	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3887	Approved
0.7182	Intermediate Similarity	NPD3020	Approved
0.7177	Intermediate Similarity	NPD4129	Approved
0.7167	Intermediate Similarity	NPD7644	Approved
0.7164	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9295	Approved
0.7143	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD6387	Discontinued
0.7143	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD709	Approved
0.7132	Intermediate Similarity	NPD1423	Approved
0.7132	Intermediate Similarity	NPD2245	Discovery
0.7132	Intermediate Similarity	NPD6666	Approved
0.7132	Intermediate Similarity	NPD6667	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