NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	188.08
Volume:	209.314
LogP:	2.939
LogD:	3.36
LogS:	-3.534
# Rotatable Bonds:	5
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.412
Synthetic Accessibility Score:	1.927
Fsp3:	0.083
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:	-4.412
MDCK Permeability:	2.891549411287997e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.899
Plasma Protein Binding (PPB):	86.57222747802734%
Volume Distribution (VD):	0.391
Pgp-substrate:	5.7780680656433105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.991
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.794
CYP2C19-substrate:	0.111
CYP2C9-inhibitor:	0.45
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.341
CYP2D6-substrate:	0.621
CYP3A4-inhibitor:	0.491
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	10.764
Half-life (T1/2):	0.749

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.022
Drug-inuced Liver Injury (DILI):	0.099
AMES Toxicity:	0.389
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.949
Carcinogencity:	0.372
Eye Corrosion:	0.894
Eye Irritation:	0.992
Respiratory Toxicity:	0.287

Download Data

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

Natural Product: NPC176228

Natural Product ID:	NPC176228
*Common Name:**	Allyl Cinnamate
IUPAC Name:	prop-2-enyl (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	KCMITHMNVLRGJU-CMDGGOBGSA-N
Standard InCHI:	InChI=1S/C12H12O2/c1-2-10-14-12(13)9-8-11-6-4-3-5-7-11/h2-9H,1,10H2/b9-8+
SMILES:	C=CCOC(=O)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2268886
PubChem CID:	641423
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0003480] Cinnamic acid esters

*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
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11291	Styrax benzoin	Species	Styracaceae	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
Others	11

Activity Type	# Activity
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	LC90	=	0.28	mg	PMID[521816]
NPT4939	Organism	Acyrthosiphon pisum	Acyrthosiphon pisum	LC90	=	0.18	mg/ml	PMID[521816]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Repellency	=	80.0	%	PMID[521816]
NPT4939	Organism	Acyrthosiphon pisum	Acyrthosiphon pisum	Repellency	=	34.0	%	PMID[521816]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	LT50	<	2.0	hr	PMID[521816]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	mortality	=	45.0	%	PMID[521816]
NPT4939	Organism	Acyrthosiphon pisum	Acyrthosiphon pisum	mortality	=	75.0	%	PMID[521816]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	LC50	=	0.2	mg	PMID[521816]
NPT4939	Organism	Acyrthosiphon pisum	Acyrthosiphon pisum	mortality	=	100.0	%	PMID[521816]
NPT4939	Organism	Acyrthosiphon pisum	Acyrthosiphon pisum	mortality	=	86.0	%	PMID[521816]
NPT4939	Organism	Acyrthosiphon pisum	Acyrthosiphon pisum	LC50	=	30.0	ug.mL-1	PMID[521816]

☑ 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 NPC176228 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	191
0.1-0.2	2577
0.2-0.3	6092
0.3-0.4	13922
0.4-0.5	14871
0.5-0.6	4171
0.6-0.7	681
0.7-0.8	152
0.8-0.85	19
0.85-0.9	7
0.9-0.95	4
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC78517
0.9863	High Similarity	NPC167577
0.96	High Similarity	NPC89950
0.96	High Similarity	NPC303245
0.9589	High Similarity	NPC287790
0.9589	High Similarity	NPC3672
0.9452	High Similarity	NPC175393
0.9351	High Similarity	NPC308619
0.9351	High Similarity	NPC127491
0.9351	High Similarity	NPC208183
0.9351	High Similarity	NPC243289
0.9351	High Similarity	NPC324835
0.9091	High Similarity	NPC71795
0.8974	High Similarity	NPC99240
0.88	High Similarity	NPC206800
0.88	High Similarity	NPC32203
0.8675	High Similarity	NPC173443
0.8659	High Similarity	NPC169050
0.8659	High Similarity	NPC286608
0.8642	High Similarity	NPC53299
0.8571	High Similarity	NPC240108
0.8571	High Similarity	NPC213156
0.8471	Intermediate Similarity	NPC119631
0.8471	Intermediate Similarity	NPC472319
0.8462	Intermediate Similarity	NPC50192
0.8434	Intermediate Similarity	NPC96625
0.8415	Intermediate Similarity	NPC58616
0.8378	Intermediate Similarity	NPC16190
0.8378	Intermediate Similarity	NPC169222
0.8378	Intermediate Similarity	NPC235059
0.8372	Intermediate Similarity	NPC77273
0.8214	Intermediate Similarity	NPC89377
0.8158	Intermediate Similarity	NPC326200
0.814	Intermediate Similarity	NPC185501
0.8125	Intermediate Similarity	NPC170484
0.8118	Intermediate Similarity	NPC304760
0.8068	Intermediate Similarity	NPC23453
0.8025	Intermediate Similarity	NPC121800
0.8023	Intermediate Similarity	NPC220893
0.8	Intermediate Similarity	NPC311343
0.8	Intermediate Similarity	NPC249912
0.8	Intermediate Similarity	NPC92754
0.8	Intermediate Similarity	NPC276775
0.7922	Intermediate Similarity	NPC155429
0.7912	Intermediate Similarity	NPC78701
0.7912	Intermediate Similarity	NPC35448
0.7912	Intermediate Similarity	NPC225060
0.7895	Intermediate Similarity	NPC98880
0.7889	Intermediate Similarity	NPC30361
0.7857	Intermediate Similarity	NPC44546
0.7831	Intermediate Similarity	NPC103387
0.7831	Intermediate Similarity	NPC323103
0.7826	Intermediate Similarity	NPC98911
0.7826	Intermediate Similarity	NPC146351
0.7826	Intermediate Similarity	NPC472318
0.7826	Intermediate Similarity	NPC118343
0.7802	Intermediate Similarity	NPC270654
0.7792	Intermediate Similarity	NPC95289
0.7778	Intermediate Similarity	NPC130398
0.7763	Intermediate Similarity	NPC239931
0.7763	Intermediate Similarity	NPC78954
0.7763	Intermediate Similarity	NPC82770
0.7742	Intermediate Similarity	NPC42211
0.7742	Intermediate Similarity	NPC70624
0.7738	Intermediate Similarity	NPC270507
0.7654	Intermediate Similarity	NPC329318
0.7579	Intermediate Similarity	NPC301943
0.7579	Intermediate Similarity	NPC82426
0.7579	Intermediate Similarity	NPC234305
0.7579	Intermediate Similarity	NPC179686
0.7579	Intermediate Similarity	NPC474365
0.7579	Intermediate Similarity	NPC91820
0.7579	Intermediate Similarity	NPC304638
0.7561	Intermediate Similarity	NPC137847
0.7561	Intermediate Similarity	NPC76455
0.7558	Intermediate Similarity	NPC294134
0.7558	Intermediate Similarity	NPC475710
0.7527	Intermediate Similarity	NPC135951
0.7527	Intermediate Similarity	NPC154517
0.75	Intermediate Similarity	NPC242913
0.75	Intermediate Similarity	NPC85977
0.75	Intermediate Similarity	NPC165212
0.75	Intermediate Similarity	NPC171831
0.75	Intermediate Similarity	NPC280616
0.7474	Intermediate Similarity	NPC188895
0.7447	Intermediate Similarity	NPC203925
0.7447	Intermediate Similarity	NPC325497
0.7447	Intermediate Similarity	NPC80115
0.7439	Intermediate Similarity	NPC179726
0.7423	Intermediate Similarity	NPC128730
0.7423	Intermediate Similarity	NPC269457
0.7419	Intermediate Similarity	NPC325499
0.7412	Intermediate Similarity	NPC106313
0.7396	Intermediate Similarity	NPC89886
0.7375	Intermediate Similarity	NPC271437
0.7368	Intermediate Similarity	NPC253746
0.7347	Intermediate Similarity	NPC37115
0.7347	Intermediate Similarity	NPC176971
0.7347	Intermediate Similarity	NPC474376
0.7347	Intermediate Similarity	NPC51174
0.7347	Intermediate Similarity	NPC326447
0.7347	Intermediate Similarity	NPC136962
0.7347	Intermediate Similarity	NPC119271
0.7347	Intermediate Similarity	NPC472316
0.7347	Intermediate Similarity	NPC475203
0.7347	Intermediate Similarity	NPC472315
0.7333	Intermediate Similarity	NPC26224
0.7326	Intermediate Similarity	NPC288903
0.7317	Intermediate Similarity	NPC78500
0.7294	Intermediate Similarity	NPC73978
0.7294	Intermediate Similarity	NPC100039
0.7292	Intermediate Similarity	NPC94343
0.7284	Intermediate Similarity	NPC208075
0.7273	Intermediate Similarity	NPC157473
0.7273	Intermediate Similarity	NPC318107
0.7273	Intermediate Similarity	NPC56493
0.7273	Intermediate Similarity	NPC260952
0.7273	Intermediate Similarity	NPC277788
0.7273	Intermediate Similarity	NPC47536
0.7273	Intermediate Similarity	NPC475465
0.7273	Intermediate Similarity	NPC20485
0.7273	Intermediate Similarity	NPC151530
0.7273	Intermediate Similarity	NPC472314
0.7263	Intermediate Similarity	NPC171843
0.7262	Intermediate Similarity	NPC300205
0.7253	Intermediate Similarity	NPC475023
0.7253	Intermediate Similarity	NPC475059
0.7245	Intermediate Similarity	NPC472919
0.7229	Intermediate Similarity	NPC245966
0.7222	Intermediate Similarity	NPC9822
0.7222	Intermediate Similarity	NPC149436
0.7216	Intermediate Similarity	NPC60679
0.7204	Intermediate Similarity	NPC5472
0.72	Intermediate Similarity	NPC83628
0.72	Intermediate Similarity	NPC17417
0.72	Intermediate Similarity	NPC184633
0.72	Intermediate Similarity	NPC114741
0.72	Intermediate Similarity	NPC40178
0.72	Intermediate Similarity	NPC182549
0.72	Intermediate Similarity	NPC474364
0.72	Intermediate Similarity	NPC10251
0.72	Intermediate Similarity	NPC206341
0.72	Intermediate Similarity	NPC265407
0.72	Intermediate Similarity	NPC469636
0.7176	Intermediate Similarity	NPC127343
0.7176	Intermediate Similarity	NPC164086
0.7174	Intermediate Similarity	NPC475057
0.7172	Intermediate Similarity	NPC477251
0.7158	Intermediate Similarity	NPC179411
0.7143	Intermediate Similarity	NPC109637
0.7143	Intermediate Similarity	NPC114594
0.7143	Intermediate Similarity	NPC31786
0.7143	Intermediate Similarity	NPC36342
0.7143	Intermediate Similarity	NPC2785
0.7143	Intermediate Similarity	NPC285470
0.7143	Intermediate Similarity	NPC2518
0.7129	Intermediate Similarity	NPC93084
0.7129	Intermediate Similarity	NPC214067
0.7129	Intermediate Similarity	NPC174099
0.7129	Intermediate Similarity	NPC251854
0.7129	Intermediate Similarity	NPC196246
0.7126	Intermediate Similarity	NPC39600
0.7126	Intermediate Similarity	NPC197581
0.7123	Intermediate Similarity	NPC198841
0.7123	Intermediate Similarity	NPC269586
0.7113	Intermediate Similarity	NPC45613
0.7097	Intermediate Similarity	NPC261181
0.7071	Intermediate Similarity	NPC209632
0.7071	Intermediate Similarity	NPC227255
0.7071	Intermediate Similarity	NPC288760
0.7071	Intermediate Similarity	NPC127676
0.7059	Intermediate Similarity	NPC167504
0.7059	Intermediate Similarity	NPC210089
0.7059	Intermediate Similarity	NPC323007
0.7059	Intermediate Similarity	NPC474157
0.7059	Intermediate Similarity	NPC260818
0.7059	Intermediate Similarity	NPC305912
0.7059	Intermediate Similarity	NPC139901
0.7059	Intermediate Similarity	NPC469894
0.7059	Intermediate Similarity	NPC476003
0.7059	Intermediate Similarity	NPC1082
0.7059	Intermediate Similarity	NPC151405
0.7059	Intermediate Similarity	NPC183700
0.7059	Intermediate Similarity	NPC43584
0.7037	Intermediate Similarity	NPC208302
0.7037	Intermediate Similarity	NPC74458
0.7027	Intermediate Similarity	NPC300345
0.7027	Intermediate Similarity	NPC65873
0.7027	Intermediate Similarity	NPC120441
0.7027	Intermediate Similarity	NPC212114
0.7024	Intermediate Similarity	NPC298023
0.7021	Intermediate Similarity	NPC32977
0.7021	Intermediate Similarity	NPC81010
0.701	Intermediate Similarity	NPC473325
0.701	Intermediate Similarity	NPC13755
0.7	Intermediate Similarity	NPC30594
0.7	Intermediate Similarity	NPC37622
0.7	Intermediate Similarity	NPC194326
0.699	Remote Similarity	NPC474314
0.699	Remote Similarity	NPC185840

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 NPC176228 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1158
0.2-0.3	1706
0.3-0.4	3392
0.4-0.5	1937
0.5-0.6	682
0.6-0.7	86
0.7-0.8	16
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.88	High Similarity	NPD9716	Approved
0.8659	High Similarity	NPD1282	Approved
0.8452	Intermediate Similarity	NPD689	Discontinued
0.7826	Intermediate Similarity	NPD1238	Approved
0.7738	Intermediate Similarity	NPD3971	Phase 1
0.7717	Intermediate Similarity	NPD5926	Approved
0.7558	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD227	Approved
0.7349	Intermediate Similarity	NPD225	Approved
0.7347	Intermediate Similarity	NPD3134	Approved
0.7273	Intermediate Similarity	NPD9259	Approved
0.7273	Intermediate Similarity	NPD1358	Approved
0.7273	Intermediate Similarity	NPD9257	Approved
0.7216	Intermediate Similarity	NPD6647	Phase 2
0.72	Intermediate Similarity	NPD2182	Approved
0.7143	Intermediate Similarity	NPD3672	Approved
0.7143	Intermediate Similarity	NPD3673	Approved
0.7143	Intermediate Similarity	NPD164	Approved
0.7097	Intermediate Similarity	NPD1202	Approved
0.7093	Intermediate Similarity	NPD226	Approved
0.7059	Intermediate Similarity	NPD9490	Approved
0.7059	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5909	Discontinued
0.6961	Remote Similarity	NPD2067	Discontinued
0.6957	Remote Similarity	NPD9256	Approved
0.6957	Remote Similarity	NPD9258	Approved
0.6932	Remote Similarity	NPD9491	Approved
0.69	Remote Similarity	NPD9697	Approved
0.6897	Remote Similarity	NPD942	Approved
0.6842	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6049	Phase 2
0.6827	Remote Similarity	NPD969	Suspended
0.6824	Remote Similarity	NPD9294	Approved
0.6782	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD1989	Approved
0.6667	Remote Similarity	NPD9260	Approved
0.6633	Remote Similarity	NPD9495	Approved
0.663	Remote Similarity	NPD650	Approved
0.663	Remote Similarity	NPD4793	Discontinued
0.663	Remote Similarity	NPD1087	Approved
0.6585	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD675	Discontinued
0.6566	Remote Similarity	NPD7798	Approved
0.6562	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1066	Discontinued
0.6545	Remote Similarity	NPD9545	Approved
0.6517	Remote Similarity	NPD9250	Approved
0.6514	Remote Similarity	NPD694	Clinical (unspecified phase)
0.65	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5346	Phase 2
0.6489	Remote Similarity	NPD800	Approved
0.6489	Remote Similarity	NPD5347	Phase 2
0.6481	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD2347	Approved
0.6452	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD1090	Approved
0.6421	Remote Similarity	NPD1089	Approved
0.6421	Remote Similarity	NPD1086	Approved
0.6408	Remote Similarity	NPD5048	Discontinued
0.64	Remote Similarity	NPD2066	Phase 3
0.6389	Remote Similarity	NPD1241	Discontinued
0.6389	Remote Similarity	NPD6010	Discontinued
0.6383	Remote Similarity	NPD531	Approved
0.6373	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD9493	Approved
0.6354	Remote Similarity	NPD1239	Approved
0.6354	Remote Similarity	NPD1007	Discontinued
0.6354	Remote Similarity	NPD7609	Phase 3
0.6339	Remote Similarity	NPD5691	Approved
0.6321	Remote Similarity	NPD5236	Approved
0.6321	Remote Similarity	NPD5235	Approved
0.6321	Remote Similarity	NPD5239	Approved
0.6321	Remote Similarity	NPD5237	Approved
0.6321	Remote Similarity	NPD5240	Approved
0.6311	Remote Similarity	NPD1237	Approved
0.6289	Remote Similarity	NPD1088	Approved
0.6289	Remote Similarity	NPD7631	Approved
0.6289	Remote Similarity	NPD1508	Approved
0.6275	Remote Similarity	NPD1932	Approved
0.6273	Remote Similarity	NPD4198	Discontinued
0.6262	Remote Similarity	NPD2201	Approved
0.6261	Remote Similarity	NPD6637	Approved
0.6238	Remote Similarity	NPD9712	Approved
0.6228	Remote Similarity	NPD3496	Discontinued
0.6226	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD1563	Approved
0.6216	Remote Similarity	NPD5292	Approved
0.6216	Remote Similarity	NPD5291	Approved
0.6214	Remote Similarity	NPD1930	Approved
0.6214	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD1929	Approved
0.6214	Remote Similarity	NPD9261	Approved
0.6204	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5705	Approved
0.619	Remote Similarity	NPD5704	Approved
0.619	Remote Similarity	NPD6685	Approved
0.619	Remote Similarity	NPD5706	Approved
0.6176	Remote Similarity	NPD2553	Approved
0.6176	Remote Similarity	NPD2555	Approved
0.6176	Remote Similarity	NPD2550	Approved
0.6176	Remote Similarity	NPD2549	Approved
0.6176	Remote Similarity	NPD2552	Approved
0.6176	Remote Similarity	NPD2558	Approved
0.6174	Remote Similarity	NPD6287	Discontinued
0.6162	Remote Similarity	NPD1693	Approved
0.6162	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2199	Approved
0.6154	Remote Similarity	NPD2198	Approved
0.6147	Remote Similarity	NPD5535	Approved
0.6147	Remote Similarity	NPD6858	Approved
0.6147	Remote Similarity	NPD7094	Approved
0.6139	Remote Similarity	NPD9711	Approved
0.6139	Remote Similarity	NPD9710	Approved
0.6132	Remote Similarity	NPD5979	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4189	Approved
0.6117	Remote Similarity	NPD4188	Approved
0.6106	Remote Similarity	NPD1894	Discontinued
0.6102	Remote Similarity	NPD553	Approved
0.6102	Remote Similarity	NPD9567	Approved
0.6102	Remote Similarity	NPD552	Approved
0.61	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.61	Remote Similarity	NPD1843	Approved
0.6095	Remote Similarity	NPD794	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD1576	Approved
0.6071	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5765	Approved
0.6055	Remote Similarity	NPD9508	Approved
0.6053	Remote Similarity	NPD5585	Approved
0.605	Remote Similarity	NPD1019	Discontinued
0.6047	Remote Similarity	NPD292	Approved
0.6047	Remote Similarity	NPD294	Approved
0.604	Remote Similarity	NPD1564	Approved
0.604	Remote Similarity	NPD1565	Approved
0.604	Remote Similarity	NPD3495	Discontinued
0.604	Remote Similarity	NPD1566	Phase 3
0.604	Remote Similarity	NPD9566	Approved
0.6038	Remote Similarity	NPD968	Approved
0.6036	Remote Similarity	NPD2629	Approved
0.6034	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD1756	Approved
0.6019	Remote Similarity	NPD1752	Approved
0.6019	Remote Similarity	NPD4233	Approved
0.6019	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4234	Approved
0.6	Remote Similarity	NPD3047	Approved
0.6	Remote Similarity	NPD4626	Approved
0.6	Remote Similarity	NPD1778	Approved
0.6	Remote Similarity	NPD3048	Approved
0.6	Remote Similarity	NPD5277	Phase 2
0.6	Remote Similarity	NPD3046	Approved
0.5983	Remote Similarity	NPD9717	Approved
0.5981	Remote Similarity	NPD9264	Approved
0.5981	Remote Similarity	NPD9263	Approved
0.5981	Remote Similarity	NPD290	Approved
0.5981	Remote Similarity	NPD9267	Approved
0.5981	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.598	Remote Similarity	NPD253	Approved
0.5979	Remote Similarity	NPD9249	Phase 1
0.5977	Remote Similarity	NPD9728	Phase 1
0.5976	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6832	Phase 2
0.5926	Remote Similarity	NPD2329	Discontinued
0.5926	Remote Similarity	NPD74	Approved
0.5926	Remote Similarity	NPD9266	Approved
0.5926	Remote Similarity	NPD2684	Approved
0.5922	Remote Similarity	NPD1067	Discontinued
0.5922	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD3535	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6912	Phase 3
0.5909	Remote Similarity	NPD505	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD9591	Approved
0.5909	Remote Similarity	NPD9594	Approved
0.5909	Remote Similarity	NPD9590	Approved
0.5909	Remote Similarity	NPD9588	Approved
0.5909	Remote Similarity	NPD80	Approved
0.5909	Remote Similarity	NPD9593	Approved
0.5909	Remote Similarity	NPD9592	Approved
0.5909	Remote Similarity	NPD9589	Approved
0.5902	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.59	Remote Similarity	NPD1080	Approved
0.5897	Remote Similarity	NPD4480	Approved
0.5897	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD422	Phase 1
0.5895	Remote Similarity	NPD111	Approved
0.5893	Remote Similarity	NPD5951	Approved
0.5888	Remote Similarity	NPD812	Approved
0.5888	Remote Similarity	NPD2559	Approved
0.5888	Remote Similarity	NPD3524	Approved
0.5888	Remote Similarity	NPD810	Approved
0.5888	Remote Similarity	NPD811	Approved
0.5888	Remote Similarity	NPD3526	Approved
0.5888	Remote Similarity	NPD467	Phase 1
0.5888	Remote Similarity	NPD2551	Approved
0.5882	Remote Similarity	NPD1076	Approved
0.5882	Remote Similarity	NPD1099	Approved
0.5882	Remote Similarity	NPD1100	Approved
0.5877	Remote Similarity	NPD5536	Phase 2
0.5872	Remote Similarity	NPD1317	Discontinued
0.5856	Remote Similarity	NPD2607	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