NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	273.17
Volume:	306.79
LogP:	3.363
LogD:	3.585
LogS:	-3.46
# Rotatable Bonds:	8
TPSA:	38.33
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.773
Synthetic Accessibility Score:	2.285
Fsp3:	0.353
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:	-4.68
MDCK Permeability:	2.2521495338878594e-05
Pgp-inhibitor:	0.964
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.602
Plasma Protein Binding (PPB):	96.88191986083984%
Volume Distribution (VD):	0.969
Pgp-substrate:	3.1613872051239014%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.726
CYP2C19-inhibitor:	0.816
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.736
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.094
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.293
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	10.171
Half-life (T1/2):	0.756

ADMET: Toxicity

hERG Blockers:	0.658
Human Hepatotoxicity (H-HT):	0.6
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.861
Rat Oral Acute Toxicity:	0.407
Maximum Recommended Daily Dose:	0.746
Skin Sensitization:	0.964
Carcinogencity:	0.539
Eye Corrosion:	0.003
Eye Irritation:	0.156
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC166837

Natural Product ID:	NPC166837
*Common Name:**	Piperovatine
IUPAC Name:	(2E,4E)-6-(4-methoxyphenyl)-N-(2-methylpropyl)hexa-2,4-dienamide
Synonyms:	Piperovatine
Standard InCHIKey:	IHRWUVSXOBLEJV-DVBIZMGNSA-N
Standard InCHI:	InChI=1S/C17H23NO2/c1-14(2)13-18-17(19)8-6-4-5-7-15-9-11-16(20-3)12-10-15/h4-6,8-12,14H,7,13H2,1-3H3,(H,18,19)/b5-4+,8-6+
SMILES:	COc1ccc(cc1)C/C=C/C=C/C(=NCC(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL250442
PubChem CID:	5374352
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO7781	Piper scutifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18031016]
NPO33260	piper hoffmanseggianum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18031016]
NPO7781	Piper scutifolium	Species	Piperaceae	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

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT487	Organism	Cladosporium cladosporioides	Cladosporium cladosporioides	MIC	=	1.0	ug	PMID[485951]
NPT488	Organism	Cladosporium sphaerospermum	Cladosporium sphaerospermum	MIC	=	1.0	ug	PMID[485951]

☑ 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 NPC166837 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	119
0.1-0.2	1932
0.2-0.3	7537
0.3-0.4	10699
0.4-0.5	6712
0.5-0.6	10887
0.6-0.7	4198
0.7-0.8	529
0.8-0.85	62
0.85-0.9	20
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9266	High Similarity	NPC303370
0.9027	High Similarity	NPC263835
0.8938	High Similarity	NPC43275
0.8938	High Similarity	NPC256369
0.8839	High Similarity	NPC258992
0.8796	High Similarity	NPC146530
0.8718	High Similarity	NPC211218
0.8655	High Similarity	NPC156944
0.8644	High Similarity	NPC95733
0.8644	High Similarity	NPC62101
0.8624	High Similarity	NPC309982
0.8621	High Similarity	NPC83279
0.8583	High Similarity	NPC291449
0.8583	High Similarity	NPC99798
0.8583	High Similarity	NPC41331
0.8583	High Similarity	NPC157740
0.8571	High Similarity	NPC170583
0.8571	High Similarity	NPC152186
0.8571	High Similarity	NPC182147
0.8571	High Similarity	NPC207541
0.8571	High Similarity	NPC246133
0.8571	High Similarity	NPC71105
0.8532	High Similarity	NPC142297
0.8512	High Similarity	NPC246974
0.8512	High Similarity	NPC147247
0.85	High Similarity	NPC251466
0.85	High Similarity	NPC301713
0.8487	Intermediate Similarity	NPC300955
0.844	Intermediate Similarity	NPC231705
0.843	Intermediate Similarity	NPC251571
0.843	Intermediate Similarity	NPC153990
0.8417	Intermediate Similarity	NPC29477
0.8376	Intermediate Similarity	NPC471308
0.8376	Intermediate Similarity	NPC53596
0.8376	Intermediate Similarity	NPC289330
0.8376	Intermediate Similarity	NPC160120
0.8376	Intermediate Similarity	NPC17388
0.8361	Intermediate Similarity	NPC155838
0.8333	Intermediate Similarity	NPC192596
0.8333	Intermediate Similarity	NPC178902
0.8304	Intermediate Similarity	NPC474149
0.8293	Intermediate Similarity	NPC35961
0.8293	Intermediate Similarity	NPC195749
0.8293	Intermediate Similarity	NPC52029
0.8288	Intermediate Similarity	NPC24101
0.8288	Intermediate Similarity	NPC201959
0.8288	Intermediate Similarity	NPC96224
0.8279	Intermediate Similarity	NPC191302
0.8279	Intermediate Similarity	NPC186898
0.8276	Intermediate Similarity	NPC323948
0.8273	Intermediate Similarity	NPC113457
0.8252	Intermediate Similarity	NPC71853
0.8241	Intermediate Similarity	NPC51633
0.8224	Intermediate Similarity	NPC100870
0.822	Intermediate Similarity	NPC321133
0.822	Intermediate Similarity	NPC41801
0.8214	Intermediate Similarity	NPC258056
0.819	Intermediate Similarity	NPC471581
0.8182	Intermediate Similarity	NPC470393
0.8182	Intermediate Similarity	NPC42383
0.8173	Intermediate Similarity	NPC321956
0.8167	Intermediate Similarity	NPC471314
0.8167	Intermediate Similarity	NPC471315
0.816	Intermediate Similarity	NPC214869
0.816	Intermediate Similarity	NPC471953
0.8155	Intermediate Similarity	NPC99886
0.8155	Intermediate Similarity	NPC177844
0.8155	Intermediate Similarity	NPC8002
0.8155	Intermediate Similarity	NPC259134
0.8103	Intermediate Similarity	NPC37302
0.8091	Intermediate Similarity	NPC38079
0.8091	Intermediate Similarity	NPC108875
0.808	Intermediate Similarity	NPC308885
0.808	Intermediate Similarity	NPC255550
0.808	Intermediate Similarity	NPC114102
0.8031	Intermediate Similarity	NPC218530
0.8016	Intermediate Similarity	NPC130595
0.8016	Intermediate Similarity	NPC93882
0.8	Intermediate Similarity	NPC470706
0.8	Intermediate Similarity	NPC305205
0.7965	Intermediate Similarity	NPC75440
0.7965	Intermediate Similarity	NPC97811
0.7953	Intermediate Similarity	NPC6854
0.7953	Intermediate Similarity	NPC313737
0.7953	Intermediate Similarity	NPC285078
0.7949	Intermediate Similarity	NPC317254
0.7928	Intermediate Similarity	NPC474603
0.7928	Intermediate Similarity	NPC12987
0.7928	Intermediate Similarity	NPC2518
0.792	Intermediate Similarity	NPC469977
0.7895	Intermediate Similarity	NPC474272
0.7891	Intermediate Similarity	NPC473463
0.7891	Intermediate Similarity	NPC282477
0.7891	Intermediate Similarity	NPC284855
0.789	Intermediate Similarity	NPC471576
0.7876	Intermediate Similarity	NPC251306
0.7874	Intermediate Similarity	NPC470392
0.7874	Intermediate Similarity	NPC274732
0.7863	Intermediate Similarity	NPC118202
0.7846	Intermediate Similarity	NPC312770
0.7846	Intermediate Similarity	NPC14600
0.7846	Intermediate Similarity	NPC204848
0.7846	Intermediate Similarity	NPC41473
0.7846	Intermediate Similarity	NPC160607
0.7812	Intermediate Similarity	NPC169766
0.7807	Intermediate Similarity	NPC153690
0.7803	Intermediate Similarity	NPC195814
0.7798	Intermediate Similarity	NPC107619
0.7798	Intermediate Similarity	NPC470161
0.7798	Intermediate Similarity	NPC175298
0.7788	Intermediate Similarity	NPC326447
0.7787	Intermediate Similarity	NPC474862
0.7786	Intermediate Similarity	NPC296898
0.7786	Intermediate Similarity	NPC299583
0.7778	Intermediate Similarity	NPC141003
0.7778	Intermediate Similarity	NPC35344
0.7778	Intermediate Similarity	NPC26524
0.776	Intermediate Similarity	NPC218323
0.7752	Intermediate Similarity	NPC303993
0.7748	Intermediate Similarity	NPC300166
0.7719	Intermediate Similarity	NPC227894
0.7719	Intermediate Similarity	NPC233320
0.7719	Intermediate Similarity	NPC186469
0.7705	Intermediate Similarity	NPC183262
0.7699	Intermediate Similarity	NPC473855
0.7699	Intermediate Similarity	NPC8302
0.7692	Intermediate Similarity	NPC165646
0.7692	Intermediate Similarity	NPC470471
0.7692	Intermediate Similarity	NPC199462
0.7686	Intermediate Similarity	NPC283760
0.7679	Intermediate Similarity	NPC298224
0.7672	Intermediate Similarity	NPC137685
0.7672	Intermediate Similarity	NPC46844
0.7667	Intermediate Similarity	NPC283468
0.7658	Intermediate Similarity	NPC289381
0.7658	Intermediate Similarity	NPC155847
0.7658	Intermediate Similarity	NPC13755
0.7647	Intermediate Similarity	NPC464
0.7647	Intermediate Similarity	NPC185541
0.7642	Intermediate Similarity	NPC177420
0.7642	Intermediate Similarity	NPC280347
0.7611	Intermediate Similarity	NPC292792
0.7611	Intermediate Similarity	NPC38209
0.7607	Intermediate Similarity	NPC156840
0.7607	Intermediate Similarity	NPC8547
0.7607	Intermediate Similarity	NPC55300
0.7607	Intermediate Similarity	NPC257124
0.7607	Intermediate Similarity	NPC173746
0.7603	Intermediate Similarity	NPC122009
0.7597	Intermediate Similarity	NPC97870
0.7597	Intermediate Similarity	NPC247018
0.7597	Intermediate Similarity	NPC307123
0.7594	Intermediate Similarity	NPC189724
0.7594	Intermediate Similarity	NPC212850
0.7594	Intermediate Similarity	NPC83289
0.7589	Intermediate Similarity	NPC12714
0.7589	Intermediate Similarity	NPC310905
0.7589	Intermediate Similarity	NPC307425
0.7586	Intermediate Similarity	NPC7097
0.7586	Intermediate Similarity	NPC246358
0.7586	Intermediate Similarity	NPC234639
0.7586	Intermediate Similarity	NPC36108
0.7586	Intermediate Similarity	NPC233731
0.7583	Intermediate Similarity	NPC19290
0.7583	Intermediate Similarity	NPC54507
0.7583	Intermediate Similarity	NPC85292
0.7583	Intermediate Similarity	NPC82963
0.7583	Intermediate Similarity	NPC229147
0.7576	Intermediate Similarity	NPC213471
0.7576	Intermediate Similarity	NPC470470
0.757	Intermediate Similarity	NPC55561
0.7565	Intermediate Similarity	NPC151530
0.7565	Intermediate Similarity	NPC157473
0.7563	Intermediate Similarity	NPC228287
0.7563	Intermediate Similarity	NPC142599
0.7563	Intermediate Similarity	NPC180508
0.7559	Intermediate Similarity	NPC296712
0.7556	Intermediate Similarity	NPC78530
0.7556	Intermediate Similarity	NPC63628
0.7556	Intermediate Similarity	NPC178466
0.7547	Intermediate Similarity	NPC25493
0.7547	Intermediate Similarity	NPC113460
0.7545	Intermediate Similarity	NPC473388
0.7544	Intermediate Similarity	NPC473393
0.7544	Intermediate Similarity	NPC227255
0.7544	Intermediate Similarity	NPC288760
0.7544	Intermediate Similarity	NPC233396
0.7544	Intermediate Similarity	NPC154899
0.7541	Intermediate Similarity	NPC310338
0.7541	Intermediate Similarity	NPC281298
0.754	Intermediate Similarity	NPC320242
0.7537	Intermediate Similarity	NPC275150
0.7537	Intermediate Similarity	NPC474128
0.7524	Intermediate Similarity	NPC197783
0.7522	Intermediate Similarity	NPC12870
0.7522	Intermediate Similarity	NPC24327
0.7522	Intermediate Similarity	NPC179686
0.7521	Intermediate Similarity	NPC164386
0.7521	Intermediate Similarity	NPC474933
0.7521	Intermediate Similarity	NPC475852

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 NPC166837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	109
0.1-0.2	790
0.2-0.3	1130
0.3-0.4	2245
0.4-0.5	2480
0.5-0.6	1550
0.6-0.7	678
0.7-0.8	161
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8559	High Similarity	NPD3676	Clinical (unspecified phase)
0.8482	Intermediate Similarity	NPD821	Approved
0.825	Intermediate Similarity	NPD3685	Discontinued
0.825	Intermediate Similarity	NPD1669	Approved
0.822	Intermediate Similarity	NPD2668	Approved
0.822	Intermediate Similarity	NPD2667	Approved
0.813	Intermediate Similarity	NPD4993	Discontinued
0.808	Intermediate Similarity	NPD3145	Approved
0.808	Intermediate Similarity	NPD3144	Approved
0.8016	Intermediate Similarity	NPD2674	Phase 3
0.7965	Intermediate Similarity	NPD2684	Approved
0.7951	Intermediate Similarity	NPD6582	Phase 2
0.7951	Intermediate Similarity	NPD6583	Phase 3
0.7881	Intermediate Similarity	NPD3596	Phase 2
0.7869	Intermediate Similarity	NPD2232	Approved
0.7869	Intermediate Similarity	NPD2233	Approved
0.7869	Intermediate Similarity	NPD2230	Approved
0.784	Intermediate Similarity	NPD1712	Approved
0.7829	Intermediate Similarity	NPD2157	Approved
0.7788	Intermediate Similarity	NPD3134	Approved
0.776	Intermediate Similarity	NPD6584	Phase 3
0.775	Intermediate Similarity	NPD6581	Approved
0.775	Intermediate Similarity	NPD6580	Approved
0.771	Intermediate Similarity	NPD4108	Discontinued
0.7692	Intermediate Similarity	NPD7843	Approved
0.7692	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD2161	Phase 2
0.7647	Intermediate Similarity	NPD709	Approved
0.7647	Intermediate Similarity	NPD2557	Approved
0.7607	Intermediate Similarity	NPD228	Approved
0.76	Intermediate Similarity	NPD2922	Phase 1
0.76	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD7477	Discontinued
0.7597	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD839	Approved
0.7597	Intermediate Similarity	NPD840	Approved
0.7597	Intermediate Similarity	NPD1423	Approved
0.7586	Intermediate Similarity	NPD5451	Approved
0.7581	Intermediate Similarity	NPD2231	Phase 2
0.7581	Intermediate Similarity	NPD2235	Phase 2
0.7578	Intermediate Similarity	NPD3165	Approved
0.7578	Intermediate Similarity	NPD3167	Approved
0.7578	Intermediate Similarity	NPD3166	Approved
0.7578	Intermediate Similarity	NPD3164	Approved
0.7578	Intermediate Similarity	NPD1024	Discontinued
0.7563	Intermediate Similarity	NPD595	Approved
0.7563	Intermediate Similarity	NPD593	Approved
0.7561	Intermediate Similarity	NPD3421	Phase 3
0.7561	Intermediate Similarity	NPD3847	Discontinued
0.754	Intermediate Similarity	NPD1818	Approved
0.754	Intermediate Similarity	NPD1817	Approved
0.754	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD1820	Approved
0.754	Intermediate Similarity	NPD1819	Approved
0.7523	Intermediate Similarity	NPD2933	Approved
0.7523	Intermediate Similarity	NPD2934	Approved
0.7519	Intermediate Similarity	NPD1048	Approved
0.75	Intermediate Similarity	NPD7157	Approved
0.7479	Intermediate Similarity	NPD2229	Approved
0.7479	Intermediate Similarity	NPD2228	Approved
0.7479	Intermediate Similarity	NPD5283	Phase 1
0.7479	Intermediate Similarity	NPD2234	Approved
0.7455	Intermediate Similarity	NPD2860	Approved
0.7455	Intermediate Similarity	NPD2859	Approved
0.7442	Intermediate Similarity	NPD5163	Phase 2
0.7426	Intermediate Similarity	NPD6331	Phase 2
0.7426	Intermediate Similarity	NPD5481	Discontinued
0.7424	Intermediate Similarity	NPD4097	Suspended
0.7422	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD1358	Approved
0.7411	Intermediate Similarity	NPD3020	Approved
0.7407	Intermediate Similarity	NPD7153	Discontinued
0.7405	Intermediate Similarity	NPD2238	Phase 2
0.7398	Intermediate Similarity	NPD3443	Approved
0.7398	Intermediate Similarity	NPD3049	Approved
0.7398	Intermediate Similarity	NPD3444	Approved
0.7398	Intermediate Similarity	NPD3445	Approved
0.7385	Intermediate Similarity	NPD5111	Phase 2
0.7385	Intermediate Similarity	NPD5110	Phase 2
0.7385	Intermediate Similarity	NPD5109	Approved
0.7385	Intermediate Similarity	NPD1039	Discontinued
0.7381	Intermediate Similarity	NPD6539	Approved
0.7381	Intermediate Similarity	NPD2428	Approved
0.7381	Intermediate Similarity	NPD6543	Approved
0.7381	Intermediate Similarity	NPD6542	Approved
0.7381	Intermediate Similarity	NPD2429	Approved
0.7381	Intermediate Similarity	NPD6540	Phase 3
0.736	Intermediate Similarity	NPD776	Approved
0.7339	Intermediate Similarity	NPD2554	Approved
0.7339	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4626	Approved
0.7339	Intermediate Similarity	NPD2556	Approved
0.7333	Intermediate Similarity	NPD111	Approved
0.7328	Intermediate Similarity	NPD1444	Approved
0.7328	Intermediate Similarity	NPD7265	Discontinued
0.7328	Intermediate Similarity	NPD968	Approved
0.7328	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1445	Approved
0.7328	Intermediate Similarity	NPD5745	Approved
0.7323	Intermediate Similarity	NPD6541	Approved
0.7323	Intermediate Similarity	NPD6538	Approved
0.7317	Intermediate Similarity	NPD2486	Discontinued
0.7308	Intermediate Similarity	NPD3179	Approved
0.7308	Intermediate Similarity	NPD6179	Discontinued
0.7308	Intermediate Similarity	NPD3180	Approved
0.7304	Intermediate Similarity	NPD9610	Approved
0.7304	Intermediate Similarity	NPD9608	Approved
0.7293	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3054	Approved
0.7293	Intermediate Similarity	NPD3052	Approved
0.7279	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4149	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1232	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4098	Discontinued
0.7266	Intermediate Similarity	NPD1794	Approved
0.7265	Intermediate Similarity	NPD290	Approved
0.7265	Intermediate Similarity	NPD5374	Approved
0.7265	Intermediate Similarity	NPD5373	Approved
0.7259	Intermediate Similarity	NPD1725	Approved
0.7259	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6382	Discontinued
0.7258	Intermediate Similarity	NPD2595	Approved
0.7258	Intermediate Similarity	NPD2594	Approved
0.7252	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5535	Approved
0.7244	Intermediate Similarity	NPD4129	Approved
0.7244	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD2614	Approved
0.7231	Intermediate Similarity	NPD682	Discontinued
0.7231	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9295	Approved
0.7213	Intermediate Similarity	NPD6387	Discontinued
0.7213	Intermediate Similarity	NPD6671	Approved
0.7209	Intermediate Similarity	NPD7018	Phase 2
0.7209	Intermediate Similarity	NPD3691	Phase 2
0.7209	Intermediate Similarity	NPD3690	Phase 2
0.7207	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3162	Approved
0.7197	Intermediate Similarity	NPD3163	Approved
0.719	Intermediate Similarity	NPD594	Approved
0.719	Intermediate Similarity	NPD592	Approved
0.7188	Intermediate Similarity	NPD196	Phase 1
0.7185	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5746	Approved
0.7176	Intermediate Similarity	NPD3136	Phase 2
0.7174	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1662	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7526	Approved
0.7163	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6390	Discontinued
0.7163	Intermediate Similarity	NPD52	Approved
0.7154	Intermediate Similarity	NPD2407	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3294	Phase 2
0.7143	Intermediate Similarity	NPD1792	Phase 2
0.7143	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3568	Approved
0.7132	Intermediate Similarity	NPD3567	Approved
0.7122	Intermediate Similarity	NPD2219	Phase 1
0.7122	Intermediate Similarity	NPD3692	Discontinued
0.7121	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7294	Phase 1
0.7121	Intermediate Similarity	NPD5718	Phase 2
0.712	Intermediate Similarity	NPD1357	Approved
0.7113	Intermediate Similarity	NPD7131	Phase 3
0.7107	Intermediate Similarity	NPD1138	Approved
0.7101	Intermediate Similarity	NPD44	Approved
0.7101	Intermediate Similarity	NPD2460	Phase 3
0.7101	Intermediate Similarity	NPD6364	Approved
0.7101	Intermediate Similarity	NPD2459	Approved
0.7101	Intermediate Similarity	NPD2458	Approved
0.7099	Intermediate Similarity	NPD596	Approved
0.7099	Intermediate Similarity	NPD600	Approved
0.7097	Intermediate Similarity	NPD856	Approved
0.7097	Intermediate Similarity	NPD1758	Phase 1
0.7097	Intermediate Similarity	NPD16	Approved
0.7092	Intermediate Similarity	NPD3985	Discontinued
0.7092	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4739	Approved
0.7092	Intermediate Similarity	NPD4123	Phase 3
0.7083	Intermediate Similarity	NPD6502	Phase 2
0.708	Intermediate Similarity	NPD1803	Phase 3
0.708	Intermediate Similarity	NPD1375	Discontinued
0.708	Intermediate Similarity	NPD3656	Approved
0.7077	Intermediate Similarity	NPD7905	Discontinued
0.7077	Intermediate Similarity	NPD7451	Discontinued
0.7068	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5846	Approved
0.7063	Intermediate Similarity	NPD6516	Phase 2
0.7059	Intermediate Similarity	NPD6380	Phase 1
0.7059	Intermediate Similarity	NPD3693	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1241	Discontinued
0.7045	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5303	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