NPASS Compound

Structure

NPC476353 OpenBabel07101719242D 22 22 0 0 1 0 0 0 0 0999 V2000 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 22 1 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 11 1 0 0 0 0 12 14 2 0 0 0 0 13 9 1 6 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 16 17 2 3 0 0 0 16 21 1 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	307.14
Volume:	315.865
LogP:	2.645
LogD:	2.856
LogS:	-3.166
# Rotatable Bonds:	8
TPSA:	95.86
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.701
Synthetic Accessibility Score:	2.749
Fsp3:	0.375
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:	-5.496
MDCK Permeability:	5.347048499970697e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.199
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.356
30% Bioavailability (F30%):	0.845

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.244
Plasma Protein Binding (PPB):	90.26538848876953%
Volume Distribution (VD):	0.312
Pgp-substrate:	7.078010559082031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.186
CYP2C19-inhibitor:	0.133
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.091
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.372
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.063

ADMET: Excretion

Clearance (CL):	9.27
Half-life (T1/2):	0.928

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.479
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.211
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.106
Carcinogencity:	0.097
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.034

Download Data

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

Natural Product: NPC476353

Natural Product ID:	NPC476353
*Common Name:**	(S)-3-(4-Hydroxy-3-(3-Methylbut-2-Enyl)Phenyl)-2-(Methoxycarbonylamino)Propanoic Acid
IUPAC Name:	(2S)-3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-2-(methoxycarbonylamino)propanoic acid
Synonyms:
Standard InCHIKey:	NOESBYUYAFDXBU-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C16H21NO5/c1-10(2)4-6-12-8-11(5-7-14(12)18)9-13(15(19)20)17-16(21)22-3/h4-5,7-8,13,18H,6,9H2,1-3H3,(H,17,21)(H,19,20)/t13-/m0/s1
SMILES:	CC(=CCC1=C(C=CC(=C1)CC(C(=O)O)NC(=O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL575617
PubChem CID:	45482327
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004319] Tyrosine 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
NPO32951	streptomyces sp. ifm 10937	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18847278]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	77.0	%	PMID[508235]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	67.0	%	PMID[508235]

☑ 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 NPC476353 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	136
0.1-0.2	793
0.2-0.3	3521
0.3-0.4	11911
0.4-0.5	7726
0.5-0.6	12858
0.6-0.7	5365
0.7-0.8	359
0.8-0.85	19
0.85-0.9	5
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9256	High Similarity	NPC142577
0.912	High Similarity	NPC296712
0.9008	High Similarity	NPC319950
0.876	High Similarity	NPC45191
0.864	High Similarity	NPC27581
0.864	High Similarity	NPC474862
0.8605	High Similarity	NPC478147
0.8462	Intermediate Similarity	NPC325651
0.8455	Intermediate Similarity	NPC281686
0.8455	Intermediate Similarity	NPC106551
0.8455	Intermediate Similarity	NPC188867
0.8409	Intermediate Similarity	NPC244866
0.8409	Intermediate Similarity	NPC470392
0.8254	Intermediate Similarity	NPC239697
0.8222	Intermediate Similarity	NPC6570
0.8195	Intermediate Similarity	NPC326966
0.8134	Intermediate Similarity	NPC328070
0.8125	Intermediate Similarity	NPC56634
0.8116	Intermediate Similarity	NPC91953
0.8088	Intermediate Similarity	NPC6913
0.8043	Intermediate Similarity	NPC197921
0.8031	Intermediate Similarity	NPC317784
0.8031	Intermediate Similarity	NPC142638
0.8029	Intermediate Similarity	NPC473055
0.8029	Intermediate Similarity	NPC473052
0.8	Intermediate Similarity	NPC88667
0.7984	Intermediate Similarity	NPC326079
0.7971	Intermediate Similarity	NPC322526
0.7951	Intermediate Similarity	NPC31274
0.7937	Intermediate Similarity	NPC317254
0.7869	Intermediate Similarity	NPC228737
0.7857	Intermediate Similarity	NPC469360
0.7842	Intermediate Similarity	NPC471201
0.7836	Intermediate Similarity	NPC161593
0.7836	Intermediate Similarity	NPC145888
0.7836	Intermediate Similarity	NPC16031
0.7823	Intermediate Similarity	NPC474149
0.7801	Intermediate Similarity	NPC13696
0.7787	Intermediate Similarity	NPC231705
0.7778	Intermediate Similarity	NPC309808
0.7769	Intermediate Similarity	NPC478121
0.7769	Intermediate Similarity	NPC190663
0.7761	Intermediate Similarity	NPC321561
0.776	Intermediate Similarity	NPC227553
0.7752	Intermediate Similarity	NPC474890
0.7752	Intermediate Similarity	NPC273282
0.7752	Intermediate Similarity	NPC161943
0.7742	Intermediate Similarity	NPC75272
0.7742	Intermediate Similarity	NPC471954
0.7742	Intermediate Similarity	NPC258056
0.7731	Intermediate Similarity	NPC245561
0.7727	Intermediate Similarity	NPC121168
0.7724	Intermediate Similarity	NPC142297
0.7717	Intermediate Similarity	NPC118202
0.771	Intermediate Similarity	NPC164852
0.7705	Intermediate Similarity	NPC303141
0.7705	Intermediate Similarity	NPC243677
0.7692	Intermediate Similarity	NPC283760
0.7692	Intermediate Similarity	NPC81026
0.7686	Intermediate Similarity	NPC178902
0.7674	Intermediate Similarity	NPC311737
0.7674	Intermediate Similarity	NPC38458
0.7667	Intermediate Similarity	NPC52472
0.7664	Intermediate Similarity	NPC257390
0.7652	Intermediate Similarity	NPC160493
0.7634	Intermediate Similarity	NPC80150
0.7622	Intermediate Similarity	NPC266741
0.7612	Intermediate Similarity	NPC4974
0.7597	Intermediate Similarity	NPC83718
0.7597	Intermediate Similarity	NPC82963
0.7594	Intermediate Similarity	NPC67300
0.7589	Intermediate Similarity	NPC48202
0.7576	Intermediate Similarity	NPC241001
0.7568	Intermediate Similarity	NPC39431
0.7561	Intermediate Similarity	NPC13495
0.7559	Intermediate Similarity	NPC286222
0.7559	Intermediate Similarity	NPC48525
0.7556	Intermediate Similarity	NPC124776
0.7552	Intermediate Similarity	NPC66518
0.7541	Intermediate Similarity	NPC13426
0.7541	Intermediate Similarity	NPC470202
0.7536	Intermediate Similarity	NPC48909
0.7533	Intermediate Similarity	NPC56635
0.752	Intermediate Similarity	NPC96224
0.752	Intermediate Similarity	NPC317305
0.752	Intermediate Similarity	NPC470039
0.752	Intermediate Similarity	NPC24101
0.7518	Intermediate Similarity	NPC217431
0.75	Intermediate Similarity	NPC260000
0.75	Intermediate Similarity	NPC305717
0.75	Intermediate Similarity	NPC148969
0.75	Intermediate Similarity	NPC242136
0.75	Intermediate Similarity	NPC188677
0.7481	Intermediate Similarity	NPC184219
0.748	Intermediate Similarity	NPC8931
0.748	Intermediate Similarity	NPC261573
0.748	Intermediate Similarity	NPC120693
0.748	Intermediate Similarity	NPC163674
0.7463	Intermediate Similarity	NPC475192
0.746	Intermediate Similarity	NPC326187
0.7447	Intermediate Similarity	NPC109580
0.7445	Intermediate Similarity	NPC17374
0.7442	Intermediate Similarity	NPC114918
0.7438	Intermediate Similarity	NPC280869
0.7438	Intermediate Similarity	NPC128723
0.7438	Intermediate Similarity	NPC12730
0.7429	Intermediate Similarity	NPC243404
0.7424	Intermediate Similarity	NPC182240
0.7422	Intermediate Similarity	NPC17693
0.7415	Intermediate Similarity	NPC132771
0.7413	Intermediate Similarity	NPC241086
0.7413	Intermediate Similarity	NPC282087
0.7413	Intermediate Similarity	NPC328137
0.7413	Intermediate Similarity	NPC318028
0.7413	Intermediate Similarity	NPC259800
0.7413	Intermediate Similarity	NPC317741
0.7413	Intermediate Similarity	NPC318984
0.7407	Intermediate Similarity	NPC174991
0.7402	Intermediate Similarity	NPC63345
0.7397	Intermediate Similarity	NPC16188
0.7394	Intermediate Similarity	NPC313694
0.7394	Intermediate Similarity	NPC242159
0.7391	Intermediate Similarity	NPC473744
0.7388	Intermediate Similarity	NPC162935
0.7388	Intermediate Similarity	NPC249340
0.7385	Intermediate Similarity	NPC23402
0.7381	Intermediate Similarity	NPC153690
0.7377	Intermediate Similarity	NPC155847
0.7377	Intermediate Similarity	NPC289381
0.7372	Intermediate Similarity	NPC210950
0.7372	Intermediate Similarity	NPC473751
0.7372	Intermediate Similarity	NPC199738
0.7368	Intermediate Similarity	NPC473136
0.7361	Intermediate Similarity	NPC251439
0.736	Intermediate Similarity	NPC70843
0.7353	Intermediate Similarity	NPC474803
0.7353	Intermediate Similarity	NPC89630
0.7348	Intermediate Similarity	NPC310467
0.7344	Intermediate Similarity	NPC177576
0.7344	Intermediate Similarity	NPC228609
0.7333	Intermediate Similarity	NPC469927
0.7328	Intermediate Similarity	NPC128249
0.7323	Intermediate Similarity	NPC234639
0.7323	Intermediate Similarity	NPC88141
0.732	Intermediate Similarity	NPC476194
0.7319	Intermediate Similarity	NPC121104
0.7308	Intermediate Similarity	NPC197513
0.7305	Intermediate Similarity	NPC173034
0.7305	Intermediate Similarity	NPC302844
0.7299	Intermediate Similarity	NPC137416
0.7293	Intermediate Similarity	NPC42657
0.7293	Intermediate Similarity	NPC43275
0.7293	Intermediate Similarity	NPC473767
0.7292	Intermediate Similarity	NPC326860
0.7292	Intermediate Similarity	NPC197239
0.7292	Intermediate Similarity	NPC150712
0.7287	Intermediate Similarity	NPC199462
0.7286	Intermediate Similarity	NPC275538
0.7285	Intermediate Similarity	NPC473580
0.7279	Intermediate Similarity	NPC14141
0.7279	Intermediate Similarity	NPC307020
0.7279	Intermediate Similarity	NPC236981
0.7273	Intermediate Similarity	NPC169328
0.7273	Intermediate Similarity	NPC325295
0.7273	Intermediate Similarity	NPC76308
0.7266	Intermediate Similarity	NPC252544
0.7266	Intermediate Similarity	NPC321252
0.7266	Intermediate Similarity	NPC222084
0.7259	Intermediate Similarity	NPC31936
0.7254	Intermediate Similarity	NPC470441
0.7254	Intermediate Similarity	NPC202743
0.7248	Intermediate Similarity	NPC324081
0.7246	Intermediate Similarity	NPC474944
0.7246	Intermediate Similarity	NPC476022
0.7246	Intermediate Similarity	NPC474945
0.7236	Intermediate Similarity	NPC225506
0.7234	Intermediate Similarity	NPC473777
0.7231	Intermediate Similarity	NPC109241
0.7231	Intermediate Similarity	NPC211421
0.7231	Intermediate Similarity	NPC190212
0.723	Intermediate Similarity	NPC17760
0.7227	Intermediate Similarity	NPC204210
0.7222	Intermediate Similarity	NPC69332
0.7222	Intermediate Similarity	NPC95178
0.7222	Intermediate Similarity	NPC29989
0.7218	Intermediate Similarity	NPC328694
0.7213	Intermediate Similarity	NPC77492
0.7208	Intermediate Similarity	NPC469243
0.72	Intermediate Similarity	NPC233702
0.7197	Intermediate Similarity	NPC471924
0.7197	Intermediate Similarity	NPC325646
0.7197	Intermediate Similarity	NPC471925
0.7197	Intermediate Similarity	NPC471928
0.7197	Intermediate Similarity	NPC28951
0.719	Intermediate Similarity	NPC8392
0.719	Intermediate Similarity	NPC212699
0.719	Intermediate Similarity	NPC207675
0.7188	Intermediate Similarity	NPC145638
0.7188	Intermediate Similarity	NPC290566
0.7188	Intermediate Similarity	NPC95172

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 NPC476353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	114
0.1-0.2	498
0.2-0.3	1004
0.3-0.4	2080
0.4-0.5	2543
0.5-0.6	1942
0.6-0.7	863
0.7-0.8	97
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8467	Intermediate Similarity	NPD3400	Discontinued
0.8455	Intermediate Similarity	NPD9568	Approved
0.8397	Intermediate Similarity	NPD3136	Phase 2
0.8374	Intermediate Similarity	NPD256	Approved
0.8374	Intermediate Similarity	NPD255	Approved
0.832	Intermediate Similarity	NPD1759	Phase 1
0.824	Intermediate Similarity	NPD1758	Phase 1
0.8134	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD259	Phase 1
0.7883	Intermediate Similarity	NPD555	Phase 2
0.7879	Intermediate Similarity	NPD196	Phase 1
0.7836	Intermediate Similarity	NPD9569	Approved
0.781	Intermediate Similarity	NPD825	Approved
0.781	Intermediate Similarity	NPD826	Approved
0.7761	Intermediate Similarity	NPD257	Approved
0.7761	Intermediate Similarity	NPD258	Approved
0.773	Intermediate Similarity	NPD7978	Discontinued
0.7714	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7450	Phase 2
0.7655	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD5304	Approved
0.7615	Intermediate Similarity	NPD5303	Approved
0.7591	Intermediate Similarity	NPD9537	Phase 1
0.7591	Intermediate Similarity	NPD9536	Phase 1
0.7584	Intermediate Similarity	NPD6502	Phase 2
0.7551	Intermediate Similarity	NPD6390	Discontinued
0.75	Intermediate Similarity	NPD7523	Phase 3
0.7483	Intermediate Similarity	NPD8019	Approved
0.748	Intermediate Similarity	NPD9610	Approved
0.748	Intermediate Similarity	NPD9608	Approved
0.7463	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2203	Discontinued
0.7426	Intermediate Similarity	NPD1135	Approved
0.7426	Intermediate Similarity	NPD1134	Approved
0.7426	Intermediate Similarity	NPD1131	Approved
0.7426	Intermediate Similarity	NPD1129	Approved
0.7426	Intermediate Similarity	NPD1133	Approved
0.7413	Intermediate Similarity	NPD9570	Approved
0.7413	Intermediate Similarity	NPD1537	Approved
0.7413	Intermediate Similarity	NPD4477	Approved
0.7413	Intermediate Similarity	NPD4476	Approved
0.7413	Intermediate Similarity	NPD1519	Approved
0.7413	Intermediate Similarity	NPD1538	Phase 1
0.7407	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD274	Approved
0.7376	Intermediate Similarity	NPD275	Approved
0.7368	Intermediate Similarity	NPD7495	Discontinued
0.7364	Intermediate Similarity	NPD2234	Approved
0.7364	Intermediate Similarity	NPD2229	Approved
0.7364	Intermediate Similarity	NPD2228	Approved
0.7357	Intermediate Similarity	NPD5745	Approved
0.7338	Intermediate Similarity	NPD9718	Approved
0.7313	Intermediate Similarity	NPD3847	Discontinued
0.7292	Intermediate Similarity	NPD1523	Approved
0.7292	Intermediate Similarity	NPD1522	Approved
0.7285	Intermediate Similarity	NPD3455	Phase 2
0.7279	Intermediate Similarity	NPD4659	Approved
0.7273	Intermediate Similarity	NPD3554	Approved
0.7273	Intermediate Similarity	NPD3555	Approved
0.7273	Intermediate Similarity	NPD317	Approved
0.7273	Intermediate Similarity	NPD1536	Approved
0.7273	Intermediate Similarity	NPD3552	Approved
0.7273	Intermediate Similarity	NPD318	Approved
0.7273	Intermediate Similarity	NPD3553	Approved
0.7266	Intermediate Similarity	NPD3643	Approved
0.7266	Intermediate Similarity	NPD3642	Approved
0.7266	Intermediate Similarity	NPD3644	Approved
0.7266	Intermediate Similarity	NPD2614	Approved
0.726	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7451	Discontinued
0.7234	Intermediate Similarity	NPD6405	Approved
0.7234	Intermediate Similarity	NPD6407	Approved
0.723	Intermediate Similarity	NPD6666	Approved
0.723	Intermediate Similarity	NPD6667	Approved
0.7214	Intermediate Similarity	NPD5746	Approved
0.7208	Intermediate Similarity	NPD7972	Discontinued
0.7206	Intermediate Similarity	NPD2562	Approved
0.7206	Intermediate Similarity	NPD2561	Approved
0.7197	Intermediate Similarity	NPD3123	Discovery
0.7197	Intermediate Similarity	NPD6746	Phase 2
0.7188	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6346	Approved
0.7174	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4103	Phase 2
0.7172	Intermediate Similarity	NPD2240	Approved
0.7172	Intermediate Similarity	NPD2239	Approved
0.7153	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1755	Approved
0.7153	Intermediate Similarity	NPD1521	Approved
0.7153	Intermediate Similarity	NPD1520	Approved
0.7153	Intermediate Similarity	NPD3685	Discontinued
0.7152	Intermediate Similarity	NPD7131	Phase 3
0.7143	Intermediate Similarity	NPD856	Approved
0.7143	Intermediate Similarity	NPD16	Approved
0.7143	Intermediate Similarity	NPD4207	Discontinued
0.7133	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5618	Discontinued
0.7121	Intermediate Similarity	NPD1348	Approved
0.7113	Intermediate Similarity	NPD520	Approved
0.7107	Intermediate Similarity	NPD7608	Discontinued
0.709	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4479	Discontinued
0.7087	Intermediate Similarity	NPD1445	Approved
0.7087	Intermediate Similarity	NPD1444	Approved
0.7078	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4208	Discontinued
0.7068	Intermediate Similarity	NPD9493	Approved
0.7059	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2935	Discontinued
0.7049	Intermediate Similarity	NPD2860	Approved
0.7049	Intermediate Similarity	NPD2859	Approved
0.7049	Intermediate Similarity	NPD1809	Phase 2
0.7045	Intermediate Similarity	NPD9618	Approved
0.7045	Intermediate Similarity	NPD9614	Approved
0.7039	Intermediate Similarity	NPD7427	Discontinued
0.7037	Intermediate Similarity	NPD4093	Discontinued
0.7037	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5688	Approved
0.7034	Intermediate Similarity	NPD5689	Approved
0.7032	Intermediate Similarity	NPD5355	Approved
0.7032	Intermediate Similarity	NPD5356	Approved
0.7029	Intermediate Similarity	NPD1669	Approved
0.7025	Intermediate Similarity	NPD845	Approved
0.7021	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5822	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6747	Phase 1
0.6992	Remote Similarity	NPD9566	Approved
0.6985	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD2667	Approved
0.6985	Remote Similarity	NPD2668	Approved
0.6985	Remote Similarity	NPD4626	Approved
0.6974	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2934	Approved
0.6967	Remote Similarity	NPD2933	Approved
0.6966	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD9545	Approved
0.6944	Remote Similarity	NPD468	Phase 1
0.6943	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4106	Approved
0.6934	Remote Similarity	NPD3143	Discontinued
0.6934	Remote Similarity	NPD4136	Approved
0.6934	Remote Similarity	NPD4135	Approved
0.6929	Remote Similarity	NPD2625	Approved
0.6929	Remote Similarity	NPD2627	Approved
0.6929	Remote Similarity	NPD2628	Approved
0.6929	Remote Similarity	NPD2626	Approved
0.6929	Remote Similarity	NPD2159	Approved
0.6929	Remote Similarity	NPD2160	Approved
0.6929	Remote Similarity	NPD1164	Approved
0.6923	Remote Similarity	NPD1792	Phase 2
0.6923	Remote Similarity	NPD4621	Approved
0.6923	Remote Similarity	NPD4619	Approved
0.6923	Remote Similarity	NPD6798	Discontinued
0.6923	Remote Similarity	NPD1048	Approved
0.6918	Remote Similarity	NPD5709	Phase 3
0.6912	Remote Similarity	NPD4105	Approved
0.6912	Remote Similarity	NPD4102	Approved
0.6912	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5981	Approved
0.6908	Remote Similarity	NPD3536	Discontinued
0.6905	Remote Similarity	NPD846	Approved
0.6905	Remote Similarity	NPD940	Approved
0.6899	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4622	Approved
0.6897	Remote Similarity	NPD4618	Approved
0.6884	Remote Similarity	NPD4806	Approved
0.6884	Remote Similarity	NPD4807	Approved
0.688	Remote Similarity	NPD3020	Approved
0.6879	Remote Similarity	NPD3691	Phase 2
0.6879	Remote Similarity	NPD3690	Phase 2
0.6875	Remote Similarity	NPD4666	Phase 3
0.6875	Remote Similarity	NPD1040	Phase 2
0.6875	Remote Similarity	NPD6663	Approved
0.6875	Remote Similarity	NPD7477	Discontinued
0.6861	Remote Similarity	NPD3019	Approved
0.6861	Remote Similarity	NPD5306	Approved
0.6861	Remote Similarity	NPD2932	Approved
0.6861	Remote Similarity	NPD5305	Approved
0.6857	Remote Similarity	NPD1283	Approved
0.6853	Remote Similarity	NPD4738	Phase 2
0.6849	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD2157	Approved
0.6849	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9266	Approved
0.6846	Remote Similarity	NPD74	Approved
0.6838	Remote Similarity	NPD2218	Phase 2
0.6838	Remote Similarity	NPD2217	Approved
0.6835	Remote Similarity	NPD6624	Discontinued
0.6831	Remote Similarity	NPD3637	Approved
0.6831	Remote Similarity	NPD3636	Approved
0.6831	Remote Similarity	NPD3635	Approved
0.6831	Remote Similarity	NPD5736	Approved
0.6829	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6032	Approved
0.6821	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6124	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data