NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	190.1
Volume:	211.95
LogP:	3.373
LogD:	3.036
LogS:	-3.346
# 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:	0.539
Synthetic Accessibility Score:	2.054
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.419
MDCK Permeability:	2.5127033950411715e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.085

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.605
Plasma Protein Binding (PPB):	91.76187896728516%
Volume Distribution (VD):	2.493
Pgp-substrate:	7.2854084968566895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.758
CYP2C19-substrate:	0.336
CYP2C9-inhibitor:	0.333
CYP2C9-substrate:	0.744
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.551
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	10.779
Half-life (T1/2):	0.298

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.778
Drug-inuced Liver Injury (DILI):	0.105
AMES Toxicity:	0.16
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.613
Carcinogencity:	0.693
Eye Corrosion:	0.226
Eye Irritation:	0.987
Respiratory Toxicity:	0.743

Download Data

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

Natural Product: NPC252004

Natural Product ID:	NPC252004
*Common Name:**	P-Isopentenyloxybenzaldehyde
IUPAC Name:	4-(3-methylbut-2-enoxy)benzaldehyde
Synonyms:	P-Isopentenyloxybenzaldehyde
Standard InCHIKey:	ZCAMZJYDORGUOV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H14O2/c1-10(2)7-8-14-12-5-3-11(9-13)4-6-12/h3-7,9H,8H2,1-2H3
SMILES:	O=Cc1ccc(cc1)OCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2022665
PubChem CID:	10921323
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers

*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
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1080/10412905.1999.9701119]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1080/10412905.1999.9701119]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650093]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19459693]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	leaf oil	n.a.	n.a.	PMID[22472691]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	7

Activity Type	# Activity
Individual Protein	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.015	n.a.	PMID[478435]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.113	n.a.	PMID[478435]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.185	n.a.	PMID[478435]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.162	n.a.	PMID[478435]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.285	n.a.	PMID[478435]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.718	n.a.	PMID[478435]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	2.654	n.a.	PMID[478435]

☑ 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 NPC252004 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	322
0.1-0.2	2369
0.2-0.3	6136
0.3-0.4	11636
0.4-0.5	4910
0.5-0.6	6584
0.6-0.7	8374
0.7-0.8	2250
0.8-0.85	88
0.85-0.9	20
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9717	High Similarity	NPC57879
0.9259	High Similarity	NPC183648
0.9174	High Similarity	NPC23332
0.9107	High Similarity	NPC470860
0.9	High Similarity	NPC54626
0.8983	High Similarity	NPC473626
0.8938	High Similarity	NPC316062
0.8889	High Similarity	NPC291189
0.8889	High Similarity	NPC69403
0.8879	High Similarity	NPC295317
0.885	High Similarity	NPC220540
0.8839	High Similarity	NPC53953
0.8814	High Similarity	NPC141252
0.8814	High Similarity	NPC11799
0.8774	High Similarity	NPC13755
0.8739	High Similarity	NPC221798
0.8696	High Similarity	NPC469954
0.8667	High Similarity	NPC470858
0.8624	High Similarity	NPC128730
0.8618	High Similarity	NPC298268
0.8595	High Similarity	NPC475236
0.8583	High Similarity	NPC255073
0.8547	High Similarity	NPC61779
0.8545	High Similarity	NPC176971
0.8532	High Similarity	NPC38209
0.8512	High Similarity	NPC165556
0.8468	Intermediate Similarity	NPC157473
0.8468	Intermediate Similarity	NPC151530
0.8462	Intermediate Similarity	NPC206007
0.8462	Intermediate Similarity	NPC293424
0.8455	Intermediate Similarity	NPC50583
0.844	Intermediate Similarity	NPC298224
0.844	Intermediate Similarity	NPC179686
0.8411	Intermediate Similarity	NPC175298
0.8403	Intermediate Similarity	NPC225245
0.839	Intermediate Similarity	NPC137710
0.8387	Intermediate Similarity	NPC170546
0.8387	Intermediate Similarity	NPC66246
0.8387	Intermediate Similarity	NPC939
0.8378	Intermediate Similarity	NPC1065
0.8376	Intermediate Similarity	NPC45104
0.8376	Intermediate Similarity	NPC217423
0.8374	Intermediate Similarity	NPC203719
0.8374	Intermediate Similarity	NPC117237
0.8362	Intermediate Similarity	NPC205523
0.8349	Intermediate Similarity	NPC84325
0.8348	Intermediate Similarity	NPC90903
0.832	Intermediate Similarity	NPC183348
0.832	Intermediate Similarity	NPC282230
0.8319	Intermediate Similarity	NPC230951
0.8319	Intermediate Similarity	NPC259554
0.8305	Intermediate Similarity	NPC27633
0.8305	Intermediate Similarity	NPC94298
0.8293	Intermediate Similarity	NPC237868
0.8288	Intermediate Similarity	NPC219913
0.8254	Intermediate Similarity	NPC15083
0.8254	Intermediate Similarity	NPC196979
0.8254	Intermediate Similarity	NPC470977
0.8254	Intermediate Similarity	NPC470976
0.824	Intermediate Similarity	NPC78662
0.824	Intermediate Similarity	NPC8005
0.8226	Intermediate Similarity	NPC37512
0.822	Intermediate Similarity	NPC312525
0.822	Intermediate Similarity	NPC217180
0.8214	Intermediate Similarity	NPC326447
0.8211	Intermediate Similarity	NPC2771
0.8211	Intermediate Similarity	NPC120066
0.8205	Intermediate Similarity	NPC188907
0.8203	Intermediate Similarity	NPC144662
0.8198	Intermediate Similarity	NPC283546
0.8197	Intermediate Similarity	NPC474691
0.819	Intermediate Similarity	NPC279916
0.8189	Intermediate Similarity	NPC470859
0.8182	Intermediate Similarity	NPC314329
0.8175	Intermediate Similarity	NPC245395
0.816	Intermediate Similarity	NPC2401
0.816	Intermediate Similarity	NPC304747
0.816	Intermediate Similarity	NPC2596
0.8158	Intermediate Similarity	NPC234639
0.8151	Intermediate Similarity	NPC32298
0.814	Intermediate Similarity	NPC212729
0.8136	Intermediate Similarity	NPC131192
0.8125	Intermediate Similarity	NPC473855
0.811	Intermediate Similarity	NPC104854
0.811	Intermediate Similarity	NPC279596
0.8091	Intermediate Similarity	NPC107101
0.8087	Intermediate Similarity	NPC179309
0.8083	Intermediate Similarity	NPC54243
0.8083	Intermediate Similarity	NPC35744
0.808	Intermediate Similarity	NPC49852
0.808	Intermediate Similarity	NPC475496
0.8067	Intermediate Similarity	NPC240664
0.8065	Intermediate Similarity	NPC65041
0.8053	Intermediate Similarity	NPC6984
0.8053	Intermediate Similarity	NPC42471
0.8047	Intermediate Similarity	NPC284424
0.8036	Intermediate Similarity	NPC109637
0.8036	Intermediate Similarity	NPC2518
0.8034	Intermediate Similarity	NPC11824
0.8031	Intermediate Similarity	NPC109778
0.8018	Intermediate Similarity	NPC307425
0.8018	Intermediate Similarity	NPC51633
0.8017	Intermediate Similarity	NPC233238
0.8016	Intermediate Similarity	NPC473907
0.8016	Intermediate Similarity	NPC125887
0.8	Intermediate Similarity	NPC471576
0.8	Intermediate Similarity	NPC177925
0.8	Intermediate Similarity	NPC125269
0.8	Intermediate Similarity	NPC187547
0.8	Intermediate Similarity	NPC141059
0.8	Intermediate Similarity	NPC154275
0.8	Intermediate Similarity	NPC171023
0.8	Intermediate Similarity	NPC152159
0.8	Intermediate Similarity	NPC21831
0.7984	Intermediate Similarity	NPC4012
0.7984	Intermediate Similarity	NPC229646
0.7984	Intermediate Similarity	NPC30216
0.7984	Intermediate Similarity	NPC107846
0.7984	Intermediate Similarity	NPC66158
0.7983	Intermediate Similarity	NPC19290
0.7982	Intermediate Similarity	NPC226699
0.7967	Intermediate Similarity	NPC311219
0.7965	Intermediate Similarity	NPC238115
0.7953	Intermediate Similarity	NPC473894
0.7951	Intermediate Similarity	NPC115859
0.7949	Intermediate Similarity	NPC22678
0.7946	Intermediate Similarity	NPC192596
0.7939	Intermediate Similarity	NPC294470
0.7937	Intermediate Similarity	NPC293387
0.7937	Intermediate Similarity	NPC16651
0.7937	Intermediate Similarity	NPC32163
0.7937	Intermediate Similarity	NPC286683
0.7934	Intermediate Similarity	NPC264976
0.7934	Intermediate Similarity	NPC201284
0.7928	Intermediate Similarity	NPC156768
0.7925	Intermediate Similarity	NPC259134
0.7925	Intermediate Similarity	NPC99886
0.7925	Intermediate Similarity	NPC177844
0.7925	Intermediate Similarity	NPC8002
0.7923	Intermediate Similarity	NPC247743
0.7923	Intermediate Similarity	NPC292998
0.7923	Intermediate Similarity	NPC209858
0.792	Intermediate Similarity	NPC83301
0.792	Intermediate Similarity	NPC224657
0.792	Intermediate Similarity	NPC52035
0.7913	Intermediate Similarity	NPC291837
0.7907	Intermediate Similarity	NPC175159
0.7907	Intermediate Similarity	NPC278556
0.7903	Intermediate Similarity	NPC118853
0.7903	Intermediate Similarity	NPC472888
0.7891	Intermediate Similarity	NPC327457
0.7891	Intermediate Similarity	NPC86774
0.7881	Intermediate Similarity	NPC109241
0.7879	Intermediate Similarity	NPC254741
0.7879	Intermediate Similarity	NPC240593
0.7876	Intermediate Similarity	NPC38079
0.7876	Intermediate Similarity	NPC108875
0.7874	Intermediate Similarity	NPC80694
0.7874	Intermediate Similarity	NPC186098
0.7874	Intermediate Similarity	NPC59502
0.7869	Intermediate Similarity	NPC246214
0.7863	Intermediate Similarity	NPC212718
0.7863	Intermediate Similarity	NPC114682
0.7857	Intermediate Similarity	NPC474264
0.7857	Intermediate Similarity	NPC474737
0.7857	Intermediate Similarity	NPC474476
0.7852	Intermediate Similarity	NPC27220
0.7851	Intermediate Similarity	NPC166591
0.7851	Intermediate Similarity	NPC243704
0.785	Intermediate Similarity	NPC71853
0.7846	Intermediate Similarity	NPC203817
0.7846	Intermediate Similarity	NPC473655
0.7846	Intermediate Similarity	NPC101294
0.7845	Intermediate Similarity	NPC95172
0.784	Intermediate Similarity	NPC473885
0.784	Intermediate Similarity	NPC184219
0.784	Intermediate Similarity	NPC471074
0.7833	Intermediate Similarity	NPC79202
0.7833	Intermediate Similarity	NPC59035
0.7829	Intermediate Similarity	NPC472517
0.7829	Intermediate Similarity	NPC301717
0.782	Intermediate Similarity	NPC188879
0.7818	Intermediate Similarity	NPC92754
0.7818	Intermediate Similarity	NPC276775
0.7818	Intermediate Similarity	NPC249912
0.7815	Intermediate Similarity	NPC292036
0.7812	Intermediate Similarity	NPC473019
0.7812	Intermediate Similarity	NPC238309
0.7812	Intermediate Similarity	NPC211120
0.7807	Intermediate Similarity	NPC470393
0.7807	Intermediate Similarity	NPC473393
0.7803	Intermediate Similarity	NPC99854
0.7795	Intermediate Similarity	NPC298884
0.7795	Intermediate Similarity	NPC22783
0.7795	Intermediate Similarity	NPC121104
0.7786	Intermediate Similarity	NPC237330
0.7786	Intermediate Similarity	NPC311339
0.7786	Intermediate Similarity	NPC223457
0.7778	Intermediate Similarity	NPC25067
0.7778	Intermediate Similarity	NPC49938

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 NPC252004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	1082
0.2-0.3	1505
0.3-0.4	2715
0.4-0.5	1831
0.5-0.6	1143
0.6-0.7	466
0.7-0.8	93
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9009	High Similarity	NPD1241	Discontinued
0.8374	Intermediate Similarity	NPD9494	Approved
0.8305	Intermediate Similarity	NPD9545	Approved
0.8264	Intermediate Similarity	NPD3972	Approved
0.8214	Intermediate Similarity	NPD3134	Approved
0.8189	Intermediate Similarity	NPD3142	Approved
0.8189	Intermediate Similarity	NPD3140	Approved
0.8182	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8142	Intermediate Similarity	NPD1358	Approved
0.8	Intermediate Similarity	NPD1019	Discontinued
0.7967	Intermediate Similarity	NPD9717	Approved
0.7879	Intermediate Similarity	NPD2796	Approved
0.7874	Intermediate Similarity	NPD6832	Phase 2
0.784	Intermediate Similarity	NPD1876	Approved
0.7724	Intermediate Similarity	NPD17	Approved
0.7705	Intermediate Similarity	NPD1894	Discontinued
0.7704	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD9697	Approved
0.7647	Intermediate Similarity	NPD4628	Phase 3
0.7638	Intermediate Similarity	NPD1203	Approved
0.7634	Intermediate Similarity	NPD1240	Approved
0.763	Intermediate Similarity	NPD1549	Phase 2
0.7607	Intermediate Similarity	NPD2684	Approved
0.7591	Intermediate Similarity	NPD3887	Approved
0.7576	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD2344	Approved
0.7556	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD2353	Approved
0.7556	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD9493	Approved
0.754	Intermediate Similarity	NPD1608	Approved
0.7536	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD1238	Approved
0.7521	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD1607	Approved
0.7482	Intermediate Similarity	NPD6799	Approved
0.7481	Intermediate Similarity	NPD1551	Phase 2
0.7481	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD5536	Phase 2
0.7463	Intermediate Similarity	NPD743	Approved
0.7447	Intermediate Similarity	NPD920	Approved
0.7444	Intermediate Similarity	NPD1933	Approved
0.744	Intermediate Similarity	NPD1778	Approved
0.7429	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2799	Discontinued
0.7407	Intermediate Similarity	NPD1510	Phase 2
0.7402	Intermediate Similarity	NPD1481	Phase 2
0.7385	Intermediate Similarity	NPD454	Approved
0.7376	Intermediate Similarity	NPD2186	Approved
0.7373	Intermediate Similarity	NPD290	Approved
0.7368	Intermediate Similarity	NPD4307	Phase 2
0.7364	Intermediate Similarity	NPD3266	Approved
0.7364	Intermediate Similarity	NPD3267	Approved
0.736	Intermediate Similarity	NPD1651	Approved
0.736	Intermediate Similarity	NPD5585	Approved
0.7355	Intermediate Similarity	NPD821	Approved
0.7355	Intermediate Similarity	NPD7843	Approved
0.7355	Intermediate Similarity	NPD5535	Approved
0.7348	Intermediate Similarity	NPD411	Approved
0.7338	Intermediate Similarity	NPD2354	Approved
0.7338	Intermediate Similarity	NPD2309	Approved
0.7324	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD1281	Approved
0.7323	Intermediate Similarity	NPD1535	Discovery
0.7319	Intermediate Similarity	NPD1243	Approved
0.7313	Intermediate Similarity	NPD447	Suspended
0.7308	Intermediate Similarity	NPD2798	Approved
0.7299	Intermediate Similarity	NPD1471	Phase 3
0.7288	Intermediate Similarity	NPD968	Approved
0.7279	Intermediate Similarity	NPD3748	Approved
0.7273	Intermediate Similarity	NPD957	Approved
0.7231	Intermediate Similarity	NPD2797	Approved
0.7222	Intermediate Similarity	NPD5691	Approved
0.7218	Intermediate Similarity	NPD2313	Discontinued
0.7218	Intermediate Similarity	NPD6798	Discontinued
0.719	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD230	Phase 1
0.7183	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD9261	Approved
0.7177	Intermediate Similarity	NPD7157	Approved
0.7172	Intermediate Similarity	NPD6599	Discontinued
0.7167	Intermediate Similarity	NPD2182	Approved
0.7164	Intermediate Similarity	NPD4062	Phase 3
0.7164	Intermediate Similarity	NPD6233	Phase 2
0.7163	Intermediate Similarity	NPD7440	Discontinued
0.7154	Intermediate Similarity	NPD1283	Approved
0.7153	Intermediate Similarity	NPD4308	Phase 3
0.7133	Intermediate Similarity	NPD6273	Approved
0.7123	Intermediate Similarity	NPD7411	Suspended
0.7123	Intermediate Similarity	NPD958	Approved
0.7122	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD164	Approved
0.7109	Intermediate Similarity	NPD3496	Discontinued
0.7101	Intermediate Similarity	NPD2935	Discontinued
0.7099	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3268	Approved
0.709	Intermediate Similarity	NPD1296	Phase 2
0.7077	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4359	Approved
0.7075	Intermediate Similarity	NPD6279	Approved
0.7075	Intermediate Similarity	NPD7577	Discontinued
0.7075	Intermediate Similarity	NPD6280	Approved
0.7067	Intermediate Similarity	NPD919	Approved
0.7063	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9092	Discovery
0.7059	Intermediate Similarity	NPD6355	Discontinued
0.7055	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD9365	Approved
0.7054	Intermediate Similarity	NPD422	Phase 1
0.7027	Intermediate Similarity	NPD7819	Suspended
0.7027	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD3225	Approved
0.7021	Intermediate Similarity	NPD3750	Approved
0.6993	Remote Similarity	NPD1511	Approved
0.6985	Remote Similarity	NPD2979	Phase 3
0.6984	Remote Similarity	NPD3596	Phase 2
0.6978	Remote Similarity	NPD4476	Approved
0.6978	Remote Similarity	NPD4477	Approved
0.6977	Remote Similarity	NPD3847	Discontinued
0.6974	Remote Similarity	NPD1247	Approved
0.6967	Remote Similarity	NPD5451	Approved
0.6959	Remote Similarity	NPD1934	Approved
0.6959	Remote Similarity	NPD6801	Discontinued
0.6953	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.695	Remote Similarity	NPD2654	Approved
0.6944	Remote Similarity	NPD4661	Approved
0.6944	Remote Similarity	NPD4662	Approved
0.6942	Remote Similarity	NPD9264	Approved
0.6942	Remote Similarity	NPD9267	Approved
0.6942	Remote Similarity	NPD9263	Approved
0.694	Remote Similarity	NPD2614	Approved
0.6934	Remote Similarity	NPD4622	Approved
0.6934	Remote Similarity	NPD4618	Approved
0.6933	Remote Similarity	NPD3882	Suspended
0.6929	Remote Similarity	NPD2346	Discontinued
0.6917	Remote Similarity	NPD5647	Approved
0.6913	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD8032	Phase 2
0.6909	Remote Similarity	NPD9259	Approved
0.6909	Remote Similarity	NPD9257	Approved
0.6901	Remote Similarity	NPD7003	Approved
0.6899	Remote Similarity	NPD4626	Approved
0.6897	Remote Similarity	NPD1512	Approved
0.6894	Remote Similarity	NPD196	Phase 1
0.6892	Remote Similarity	NPD6385	Approved
0.6892	Remote Similarity	NPD6386	Approved
0.6887	Remote Similarity	NPD7075	Discontinued
0.6885	Remote Similarity	NPD9266	Approved
0.6885	Remote Similarity	NPD74	Approved
0.6875	Remote Similarity	NPD6580	Approved
0.6875	Remote Similarity	NPD1548	Phase 1
0.6875	Remote Similarity	NPD6581	Approved
0.6875	Remote Similarity	NPD1182	Approved
0.6871	Remote Similarity	NPD7458	Discontinued
0.6867	Remote Similarity	NPD3817	Phase 2
0.6867	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2239	Approved
0.6857	Remote Similarity	NPD2240	Approved
0.6855	Remote Similarity	NPD228	Approved
0.6849	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1670	Discontinued
0.6842	Remote Similarity	NPD6862	Phase 2
0.6838	Remote Similarity	NPD3764	Approved
0.6835	Remote Similarity	NPD5688	Approved
0.6835	Remote Similarity	NPD5689	Approved
0.6828	Remote Similarity	NPD5401	Approved
0.6828	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3146	Approved
0.6824	Remote Similarity	NPD4380	Phase 2
0.6822	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2801	Approved
0.6797	Remote Similarity	NPD5494	Approved
0.6786	Remote Similarity	NPD7033	Discontinued
0.6783	Remote Similarity	NPD1202	Approved
0.6783	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5049	Phase 3
0.6776	Remote Similarity	NPD1307	Phase 2
0.6776	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1309	Phase 2
0.6772	Remote Similarity	NPD2557	Approved
0.6769	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5846	Approved
0.6769	Remote Similarity	NPD6516	Phase 2
0.6765	Remote Similarity	NPD5163	Phase 2
0.6761	Remote Similarity	NPD4534	Discontinued
0.6759	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2649	Approved
0.6757	Remote Similarity	NPD2651	Approved
0.6757	Remote Similarity	NPD824	Approved
0.6755	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2296	Approved
0.6753	Remote Similarity	NPD2249	Approved
0.6753	Remote Similarity	NPD2247	Approved
0.6746	Remote Similarity	NPD594	Approved
0.6746	Remote Similarity	NPD5283	Phase 1
0.6746	Remote Similarity	NPD592	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