NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	174.07
Volume:	192.018
LogP:	2.052
LogD:	1.67
LogS:	-3.181
# Rotatable Bonds:	3
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	2.009
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.783
MDCK Permeability:	1.348616660834523e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.191
30% Bioavailability (F30%):	0.575

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.363
Plasma Protein Binding (PPB):	85.52635192871094%
Volume Distribution (VD):	0.324
Pgp-substrate:	7.581260681152344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.27
CYP1A2-substrate:	0.065
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.16
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.156
CYP2D6-substrate:	0.676
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.091

ADMET: Excretion

Clearance (CL):	1.347
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.782
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.895
Carcinogencity:	0.055
Eye Corrosion:	0.91
Eye Irritation:	0.994
Respiratory Toxicity:	0.831

Download Data

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

Natural Product: NPC32203

Natural Product ID:	NPC32203
*Common Name:**	Juarezic Acid
IUPAC Name:	(2E,4E)-5-phenylpenta-2,4-dienoic acid
Synonyms:	(E,E)-Cinnamylideneacetic Acid
Standard InCHIKey:	FEIQOMCWGDNMHM-KBXRYBNXSA-N
Standard InCHI:	InChI=1S/C11H10O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-9H,(H,12,13)/b8-4+,9-5+
SMILES:	OC(=O)/C=C/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095566
PubChem CID:	1549512
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17548953]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20166702]
NPO40884	Mexican propolis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20307087]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21114277]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21171571]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24675423]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Bako, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Enemore, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Gedo, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Holleta, Ethiopia		PMID[24926420]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29094598]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	3
Potency	2

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	>	100.0	uM	PMID[484397]
NPT2	Others	Unspecified		Potency	=	7943.3	nM	PMID[484398]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	220.0	nM	PMID[484399]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	88.74	%	PMID[484400]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	102.26	%	PMID[484400]
NPT2	Others	Unspecified		Potency	n.a.	3981.1	nM	PMID[484398]

☑ 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 NPC32203 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	157
0.1-0.2	2868
0.2-0.3	6966
0.3-0.4	15356
0.4-0.5	13239
0.5-0.6	3167
0.6-0.7	765
0.7-0.8	148
0.8-0.85	17
0.85-0.9	10
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC206800
0.9583	High Similarity	NPC50192
0.8919	High Similarity	NPC287790
0.8919	High Similarity	NPC3672
0.8846	High Similarity	NPC44546
0.88	High Similarity	NPC176228
0.875	High Similarity	NPC155429
0.8684	High Similarity	NPC78517
0.8684	High Similarity	NPC167577
0.8462	Intermediate Similarity	NPC71795
0.8462	Intermediate Similarity	NPC303245
0.8462	Intermediate Similarity	NPC89950
0.8333	Intermediate Similarity	NPC78954
0.8333	Intermediate Similarity	NPC82770
0.8333	Intermediate Similarity	NPC311343
0.8333	Intermediate Similarity	NPC239931
0.8289	Intermediate Similarity	NPC175393
0.825	Intermediate Similarity	NPC324835
0.825	Intermediate Similarity	NPC243289
0.825	Intermediate Similarity	NPC208183
0.825	Intermediate Similarity	NPC127491
0.825	Intermediate Similarity	NPC308619
0.8219	Intermediate Similarity	NPC16190
0.8219	Intermediate Similarity	NPC169222
0.8219	Intermediate Similarity	NPC235059
0.8219	Intermediate Similarity	NPC98880
0.8214	Intermediate Similarity	NPC26224
0.8125	Intermediate Similarity	NPC99240
0.8118	Intermediate Similarity	NPC472319
0.8108	Intermediate Similarity	NPC95289
0.8	Intermediate Similarity	NPC326200
0.7875	Intermediate Similarity	NPC127343
0.7857	Intermediate Similarity	NPC194326
0.7841	Intermediate Similarity	NPC32977
0.7841	Intermediate Similarity	NPC81010
0.7831	Intermediate Similarity	NPC123476
0.7831	Intermediate Similarity	NPC53299
0.7791	Intermediate Similarity	NPC62765
0.7753	Intermediate Similarity	NPC257182
0.7753	Intermediate Similarity	NPC246679
0.7722	Intermediate Similarity	NPC179726
0.7674	Intermediate Similarity	NPC173443
0.7667	Intermediate Similarity	NPC133135
0.7667	Intermediate Similarity	NPC253423
0.7667	Intermediate Similarity	NPC251579
0.7647	Intermediate Similarity	NPC286608
0.7647	Intermediate Similarity	NPC169050
0.7647	Intermediate Similarity	NPC96625
0.759	Intermediate Similarity	NPC285773
0.759	Intermediate Similarity	NPC44830
0.7586	Intermediate Similarity	NPC213156
0.7586	Intermediate Similarity	NPC240108
0.7582	Intermediate Similarity	NPC140619
0.7582	Intermediate Similarity	NPC179411
0.7582	Intermediate Similarity	NPC229242
0.7556	Intermediate Similarity	NPC61944
0.7556	Intermediate Similarity	NPC30361
0.7536	Intermediate Similarity	NPC149436
0.7531	Intermediate Similarity	NPC469894
0.7531	Intermediate Similarity	NPC170484
0.7531	Intermediate Similarity	NPC300205
0.7529	Intermediate Similarity	NPC318107
0.75	Intermediate Similarity	NPC267704
0.75	Intermediate Similarity	NPC245966
0.75	Intermediate Similarity	NPC217621
0.75	Intermediate Similarity	NPC119631
0.75	Intermediate Similarity	NPC329318
0.75	Intermediate Similarity	NPC475023
0.75	Intermediate Similarity	NPC475059
0.7439	Intermediate Similarity	NPC121800
0.7439	Intermediate Similarity	NPC164086
0.7429	Intermediate Similarity	NPC269586
0.7429	Intermediate Similarity	NPC198841
0.7419	Intermediate Similarity	NPC253746
0.7416	Intermediate Similarity	NPC77273
0.7416	Intermediate Similarity	NPC475057
0.7412	Intermediate Similarity	NPC95965
0.7412	Intermediate Similarity	NPC58616
0.7407	Intermediate Similarity	NPC2785
0.7407	Intermediate Similarity	NPC137847
0.7407	Intermediate Similarity	NPC36342
0.7407	Intermediate Similarity	NPC285470
0.7407	Intermediate Similarity	NPC76455
0.7391	Intermediate Similarity	NPC135951
0.7391	Intermediate Similarity	NPC154517
0.7349	Intermediate Similarity	NPC242628
0.734	Intermediate Similarity	NPC284477
0.734	Intermediate Similarity	NPC25458
0.734	Intermediate Similarity	NPC94343
0.734	Intermediate Similarity	NPC304873
0.7333	Intermediate Similarity	NPC261181
0.7333	Intermediate Similarity	NPC181709
0.7324	Intermediate Similarity	NPC65873
0.7324	Intermediate Similarity	NPC300345
0.7324	Intermediate Similarity	NPC212114
0.7324	Intermediate Similarity	NPC120441
0.7317	Intermediate Similarity	NPC151405
0.7317	Intermediate Similarity	NPC139901
0.7312	Intermediate Similarity	NPC80115
0.7312	Intermediate Similarity	NPC228435
0.7308	Intermediate Similarity	NPC74458
0.7308	Intermediate Similarity	NPC208302
0.7303	Intermediate Similarity	NPC110704
0.7286	Intermediate Similarity	NPC277704
0.7284	Intermediate Similarity	NPC66655
0.7263	Intermediate Similarity	NPC91820
0.7263	Intermediate Similarity	NPC470202
0.7263	Intermediate Similarity	NPC304638
0.7263	Intermediate Similarity	NPC82426
0.7263	Intermediate Similarity	NPC255676
0.7262	Intermediate Similarity	NPC323103
0.7262	Intermediate Similarity	NPC103387
0.7253	Intermediate Similarity	NPC130398
0.7253	Intermediate Similarity	NPC473347
0.7241	Intermediate Similarity	NPC322387
0.7241	Intermediate Similarity	NPC89377
0.7234	Intermediate Similarity	NPC282895
0.7229	Intermediate Similarity	NPC190567
0.7229	Intermediate Similarity	NPC71664
0.7222	Intermediate Similarity	NPC36357
0.7222	Intermediate Similarity	NPC8235
0.7222	Intermediate Similarity	NPC114327
0.7215	Intermediate Similarity	NPC271437
0.7215	Intermediate Similarity	NPC285679
0.7191	Intermediate Similarity	NPC185501
0.7188	Intermediate Similarity	NPC472222
0.7188	Intermediate Similarity	NPC472221
0.7188	Intermediate Similarity	NPC93831
0.7188	Intermediate Similarity	NPC242913
0.7188	Intermediate Similarity	NPC171831
0.7188	Intermediate Similarity	NPC280616
0.7188	Intermediate Similarity	NPC2518
0.7176	Intermediate Similarity	NPC288903
0.7176	Intermediate Similarity	NPC270507
0.7176	Intermediate Similarity	NPC273758
0.7174	Intermediate Similarity	NPC286006
0.7174	Intermediate Similarity	NPC3371
0.716	Intermediate Similarity	NPC78500
0.7159	Intermediate Similarity	NPC304760
0.7159	Intermediate Similarity	NPC329064
0.7159	Intermediate Similarity	NPC325441
0.7143	Intermediate Similarity	NPC100039
0.7143	Intermediate Similarity	NPC145053
0.7143	Intermediate Similarity	NPC23453
0.7143	Intermediate Similarity	NPC12936
0.7143	Intermediate Similarity	NPC273033
0.7143	Intermediate Similarity	NPC117180
0.7143	Intermediate Similarity	NPC73978
0.7143	Intermediate Similarity	NPC133050
0.7125	Intermediate Similarity	NPC108218
0.7125	Intermediate Similarity	NPC208075
0.7123	Intermediate Similarity	NPC147062
0.7123	Intermediate Similarity	NPC169110
0.7113	Intermediate Similarity	NPC105899
0.7113	Intermediate Similarity	NPC227255
0.7113	Intermediate Similarity	NPC288760
0.7113	Intermediate Similarity	NPC243677
0.7113	Intermediate Similarity	NPC303141
0.7097	Intermediate Similarity	NPC249912
0.7097	Intermediate Similarity	NPC283711
0.7097	Intermediate Similarity	NPC289201
0.7097	Intermediate Similarity	NPC278228
0.7097	Intermediate Similarity	NPC92754
0.7097	Intermediate Similarity	NPC276775
0.7079	Intermediate Similarity	NPC220893
0.7059	Intermediate Similarity	NPC87299
0.7059	Intermediate Similarity	NPC14326
0.7059	Intermediate Similarity	NPC329319
0.7059	Intermediate Similarity	NPC283012
0.7059	Intermediate Similarity	NPC103326
0.7059	Intermediate Similarity	NPC475199
0.7059	Intermediate Similarity	NPC99394
0.7041	Intermediate Similarity	NPC1075
0.7041	Intermediate Similarity	NPC136962
0.7041	Intermediate Similarity	NPC37115
0.7041	Intermediate Similarity	NPC51174
0.7041	Intermediate Similarity	NPC1786
0.7041	Intermediate Similarity	NPC294902
0.7037	Intermediate Similarity	NPC189371
0.7027	Intermediate Similarity	NPC246588
0.7027	Intermediate Similarity	NPC238023
0.7027	Intermediate Similarity	NPC310758
0.7027	Intermediate Similarity	NPC248705
0.7027	Intermediate Similarity	NPC135924
0.7027	Intermediate Similarity	NPC54368
0.7027	Intermediate Similarity	NPC150196
0.7027	Intermediate Similarity	NPC210849
0.7024	Intermediate Similarity	NPC17408
0.7024	Intermediate Similarity	NPC285716
0.7024	Intermediate Similarity	NPC95868
0.7024	Intermediate Similarity	NPC309279
0.7024	Intermediate Similarity	NPC328178
0.7021	Intermediate Similarity	NPC35448
0.7021	Intermediate Similarity	NPC317280
0.7021	Intermediate Similarity	NPC160548
0.7021	Intermediate Similarity	NPC225060
0.7021	Intermediate Similarity	NPC175852
0.7021	Intermediate Similarity	NPC329387
0.7021	Intermediate Similarity	NPC476120
0.7021	Intermediate Similarity	NPC78701

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 NPC32203 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1162
0.2-0.3	1790
0.3-0.4	3388
0.4-0.5	1875
0.5-0.6	652
0.6-0.7	109
0.7-0.8	21
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD9716	Approved
0.8718	High Similarity	NPD3971	Phase 1
0.85	High Similarity	NPD5734	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD689	Discontinued
0.7791	Intermediate Similarity	NPD9258	Approved
0.7791	Intermediate Similarity	NPD9256	Approved
0.7778	Intermediate Similarity	NPD226	Approved
0.7647	Intermediate Similarity	NPD1282	Approved
0.764	Intermediate Similarity	NPD6049	Phase 2
0.764	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD227	Approved
0.7625	Intermediate Similarity	NPD225	Approved
0.759	Intermediate Similarity	NPD9491	Approved
0.7529	Intermediate Similarity	NPD9257	Approved
0.7529	Intermediate Similarity	NPD9259	Approved
0.7333	Intermediate Similarity	NPD1202	Approved
0.7317	Intermediate Similarity	NPD9490	Approved
0.7284	Intermediate Similarity	NPD9294	Approved
0.7263	Intermediate Similarity	NPD6647	Phase 2
0.7241	Intermediate Similarity	NPD4793	Discontinued
0.7143	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD942	Approved
0.7079	Intermediate Similarity	NPD5346	Phase 2
0.7079	Intermediate Similarity	NPD800	Approved
0.7079	Intermediate Similarity	NPD5347	Phase 2
0.7051	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD9495	Approved
0.701	Intermediate Similarity	NPD5909	Discontinued
0.7	Intermediate Similarity	NPD1089	Approved
0.7	Intermediate Similarity	NPD1086	Approved
0.7	Intermediate Similarity	NPD1090	Approved
0.6947	Remote Similarity	NPD2066	Phase 3
0.6947	Remote Similarity	NPD9712	Approved
0.6947	Remote Similarity	NPD1238	Approved
0.6923	Remote Similarity	NPD1239	Approved
0.69	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD9260	Approved
0.6854	Remote Similarity	NPD650	Approved
0.6854	Remote Similarity	NPD1087	Approved
0.6848	Remote Similarity	NPD1088	Approved
0.6842	Remote Similarity	NPD9711	Approved
0.6842	Remote Similarity	NPD675	Discontinued
0.6842	Remote Similarity	NPD9710	Approved
0.6842	Remote Similarity	NPD5926	Approved
0.6804	Remote Similarity	NPD1932	Approved
0.6774	Remote Similarity	NPD1066	Discontinued
0.6753	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1930	Approved
0.6735	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1929	Approved
0.6702	Remote Similarity	NPD1693	Approved
0.6702	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD9508	Approved
0.6667	Remote Similarity	NPD164	Approved
0.6667	Remote Similarity	NPD1237	Approved
0.6667	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5277	Phase 2
0.6634	Remote Similarity	NPD9263	Approved
0.6634	Remote Similarity	NPD9264	Approved
0.6634	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD9267	Approved
0.6632	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3672	Approved
0.663	Remote Similarity	NPD3673	Approved
0.6629	Remote Similarity	NPD111	Approved
0.66	Remote Similarity	NPD5048	Discontinued
0.66	Remote Similarity	NPD1576	Approved
0.6569	Remote Similarity	NPD74	Approved
0.6569	Remote Similarity	NPD9266	Approved
0.6562	Remote Similarity	NPD1565	Approved
0.6562	Remote Similarity	NPD1564	Approved
0.6562	Remote Similarity	NPD9566	Approved
0.6562	Remote Similarity	NPD1566	Phase 3
0.6559	Remote Similarity	NPD1007	Discontinued
0.6559	Remote Similarity	NPD7609	Phase 3
0.6552	Remote Similarity	NPD9250	Approved
0.6535	Remote Similarity	NPD3134	Approved
0.6509	Remote Similarity	NPD5951	Approved
0.6509	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD253	Approved
0.6489	Remote Similarity	NPD7631	Approved
0.6489	Remote Similarity	NPD1508	Approved
0.6489	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1358	Approved
0.6436	Remote Similarity	NPD9697	Approved
0.6429	Remote Similarity	NPD1067	Discontinued
0.6429	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD1563	Approved
0.6413	Remote Similarity	NPD531	Approved
0.6408	Remote Similarity	NPD2329	Discontinued
0.6408	Remote Similarity	NPD2182	Approved
0.64	Remote Similarity	NPD9261	Approved
0.6389	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD9493	Approved
0.6381	Remote Similarity	NPD969	Suspended
0.6354	Remote Similarity	NPD2934	Approved
0.6354	Remote Similarity	NPD2933	Approved
0.6346	Remote Similarity	NPD1317	Discontinued
0.6304	Remote Similarity	NPD9538	Approved
0.6289	Remote Similarity	NPD2860	Approved
0.6289	Remote Similarity	NPD1989	Approved
0.6289	Remote Similarity	NPD1843	Approved
0.6289	Remote Similarity	NPD2859	Approved
0.6286	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD9545	Approved
0.6265	Remote Similarity	NPD292	Approved
0.6265	Remote Similarity	NPD294	Approved
0.625	Remote Similarity	NPD845	Approved
0.6239	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5765	Approved
0.6237	Remote Similarity	NPD1101	Approved
0.6224	Remote Similarity	NPD3495	Discontinued
0.6204	Remote Similarity	NPD9281	Approved
0.619	Remote Similarity	NPD2067	Discontinued
0.619	Remote Similarity	NPD9728	Phase 1
0.6186	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.617	Remote Similarity	NPD1628	Approved
0.617	Remote Similarity	NPD1629	Approved
0.6161	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD1104	Approved
0.6161	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4194	Approved
0.6154	Remote Similarity	NPD4192	Approved
0.6154	Remote Similarity	NPD4191	Approved
0.6154	Remote Similarity	NPD4193	Approved
0.6129	Remote Similarity	NPD187	Approved
0.6122	Remote Similarity	NPD844	Approved
0.6118	Remote Similarity	NPD9590	Approved
0.6118	Remote Similarity	NPD9594	Approved
0.6118	Remote Similarity	NPD9589	Approved
0.6118	Remote Similarity	NPD9588	Approved
0.6118	Remote Similarity	NPD80	Approved
0.6118	Remote Similarity	NPD9591	Approved
0.6118	Remote Similarity	NPD9593	Approved
0.6118	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD9592	Approved
0.6117	Remote Similarity	NPD1040	Phase 2
0.61	Remote Similarity	NPD3020	Approved
0.61	Remote Similarity	NPD7798	Approved
0.6082	Remote Similarity	NPD719	Approved
0.6082	Remote Similarity	NPD720	Approved
0.6061	Remote Similarity	NPD288	Approved
0.6061	Remote Similarity	NPD1099	Approved
0.6061	Remote Similarity	NPD1100	Approved
0.6058	Remote Similarity	NPD6685	Approved
0.6058	Remote Similarity	NPD467	Phase 1
0.6055	Remote Similarity	NPD2629	Approved
0.6055	Remote Similarity	NPD1246	Approved
0.6042	Remote Similarity	NPD530	Approved
0.604	Remote Similarity	NPD289	Clinical (unspecified phase)
0.604	Remote Similarity	NPD1242	Phase 1
0.6024	Remote Similarity	NPD1673	Approved
0.602	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD4626	Approved
0.6	Remote Similarity	NPD9612	Approved
0.6	Remote Similarity	NPD9717	Approved
0.6	Remote Similarity	NPD9609	Approved
0.6	Remote Similarity	NPD9249	Phase 1
0.6	Remote Similarity	NPD5979	Clinical (unspecified phase)
0.6	Remote Similarity	NPD255	Approved
0.6	Remote Similarity	NPD9611	Approved
0.6	Remote Similarity	NPD256	Approved
0.598	Remote Similarity	NPD940	Approved
0.598	Remote Similarity	NPD846	Approved
0.5979	Remote Similarity	NPD9251	Approved
0.5979	Remote Similarity	NPD752	Approved
0.5965	Remote Similarity	NPD3496	Discontinued
0.5963	Remote Similarity	NPD6010	Discontinued
0.596	Remote Similarity	NPD1809	Phase 2
0.5948	Remote Similarity	NPD182	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD9568	Approved
0.593	Remote Similarity	NPD9087	Approved
0.5918	Remote Similarity	NPD1409	Phase 3
0.5918	Remote Similarity	NPD3719	Approved
0.5918	Remote Similarity	NPD1080	Approved
0.5918	Remote Similarity	NPD3718	Approved
0.5913	Remote Similarity	NPD422	Phase 1
0.5909	Remote Similarity	NPD4144	Approved
0.5909	Remote Similarity	NPD4147	Approved
0.5909	Remote Similarity	NPD603	Approved
0.59	Remote Similarity	NPD1875	Phase 1
0.59	Remote Similarity	NPD1076	Approved
0.5897	Remote Similarity	NPD1888	Phase 1
0.5893	Remote Similarity	NPD1758	Phase 1
0.5888	Remote Similarity	NPD5236	Approved
0.5888	Remote Similarity	NPD5235	Approved
0.5888	Remote Similarity	NPD5278	Discontinued
0.5888	Remote Similarity	NPD5239	Approved
0.5888	Remote Similarity	NPD5240	Approved
0.5888	Remote Similarity	NPD664	Approved
0.5888	Remote Similarity	NPD5237	Approved
0.5882	Remote Similarity	NPD1616	Discontinued
0.5877	Remote Similarity	NPD9272	Approved
0.5862	Remote Similarity	NPD1877	Discontinued
0.5859	Remote Similarity	NPD4814	Discontinued
0.5856	Remote Similarity	NPD4198	Discontinued
0.5849	Remote Similarity	NPD9532	Phase 3
0.5847	Remote Similarity	NPD1164	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