NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	174.05
Volume:	159.75
LogP:	-1.541
LogD:	-1.129
LogS:	-0.307
# Rotatable Bonds:	1
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.462
Synthetic Accessibility Score:	3.683
Fsp3:	0.714
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:	-5.809
MDCK Permeability:	0.0014441669918596745
Pgp-inhibitor:	0.001
Pgp-substrate:	0.137
Human Intestinal Absorption (HIA):	0.267
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.845
Plasma Protein Binding (PPB):	19.435766220092773%
Volume Distribution (VD):	0.334
Pgp-substrate:	68.44634246826172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	3.591
Half-life (T1/2):	0.917

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.096
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.047
Carcinogencity:	0.019
Eye Corrosion:	0.006
Eye Irritation:	0.353
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC47844

Natural Product ID:	NPC47844
*Common Name:**	Shikimic Acid
IUPAC Name:	(3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
Synonyms:	Shicimic Acid; Shikimic Acid
Standard InCHIKey:	JXOHGGNKMLTUBP-HSUXUTPPSA-N
Standard InCHI:	InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1
SMILES:	C1=C(C[C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL290345
PubChem CID:	8742
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives [CHEMONTID:0002509] Cyclitols and derivatives [CHEMONTID:0002278] Shikimic acids and derivatves

*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

☑ 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
NPO2300	NPC47844	n.a.	Fruits	440	n.a.	n.a.	mg/100g of FW	PMID[23394984]

☑ 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	5
Others	10
Potency	3

Activity Type	# Activity
Individual Protein	14
ORGANISM	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3015	Individual Protein	5-enolpyruvylshikimate-3-phosphate synthase	Escherichia coli K-12	IC50	>	90000000.0	nM	PMID[540184]
NPT3016	Individual Protein	Selectin E	Homo sapiens	Inhibition	=	25.6	%	PMID[540185]
NPT3017	Individual Protein	P-selectin	Homo sapiens	Inhibition	=	-1.0	%	PMID[540185]
NPT3018	Individual Protein	Leukocyte adhesion molecule-1	Homo sapiens	Inhibition	=	12.2	%	PMID[540185]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	<	30.0	%	PMID[540186]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4610.9	nM	PMID[540188]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	366.3	nM	PMID[540188]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-8.33	%	PMID[540189]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	354.8	nM	PMID[540191]
NPT702	Individual Protein	UDP-glucuronosyltransferase 1-6	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[540187]
NPT703	Individual Protein	UDP-glucuronosyltransferase 1-9	Homo sapiens	Activity	=	0.0	pm/min/mg	PMID[540187]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-4.96	%	PMID[540189]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	81.49	%	PMID[540190]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	97.13	%	PMID[540190]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[540192]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[540192]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[540193]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[540193]

☑ 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 NPC47844 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	210
0.1-0.2	1894
0.2-0.3	6614
0.3-0.4	14618
0.4-0.5	11924
0.5-0.6	5620
0.6-0.7	1614
0.7-0.8	197
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC141195
0.9103	High Similarity	NPC316819
0.8256	Intermediate Similarity	NPC327620
0.7805	Intermediate Similarity	NPC221510
0.7805	Intermediate Similarity	NPC159714
0.7711	Intermediate Similarity	NPC253364
0.7647	Intermediate Similarity	NPC77971
0.76	Intermediate Similarity	NPC472072
0.7586	Intermediate Similarity	NPC473715
0.7558	Intermediate Similarity	NPC112685
0.7529	Intermediate Similarity	NPC469809
0.7528	Intermediate Similarity	NPC114345
0.7528	Intermediate Similarity	NPC303230
0.7528	Intermediate Similarity	NPC473321
0.7528	Intermediate Similarity	NPC6099
0.75	Intermediate Similarity	NPC20066
0.747	Intermediate Similarity	NPC470946
0.747	Intermediate Similarity	NPC470945
0.747	Intermediate Similarity	NPC470947
0.7468	Intermediate Similarity	NPC325627
0.7444	Intermediate Similarity	NPC162205
0.7444	Intermediate Similarity	NPC288240
0.7444	Intermediate Similarity	NPC273579
0.7444	Intermediate Similarity	NPC295204
0.7442	Intermediate Similarity	NPC21469
0.7442	Intermediate Similarity	NPC182383
0.7419	Intermediate Similarity	NPC300584
0.7416	Intermediate Similarity	NPC471399
0.7416	Intermediate Similarity	NPC473619
0.7356	Intermediate Similarity	NPC47937
0.7333	Intermediate Similarity	NPC142838
0.7333	Intermediate Similarity	NPC327760
0.7326	Intermediate Similarity	NPC474251
0.7303	Intermediate Similarity	NPC477011
0.7303	Intermediate Similarity	NPC280612
0.7294	Intermediate Similarity	NPC47450
0.7273	Intermediate Similarity	NPC178215
0.7253	Intermediate Similarity	NPC11456
0.7253	Intermediate Similarity	NPC475912
0.7241	Intermediate Similarity	NPC66346
0.7241	Intermediate Similarity	NPC283085
0.7241	Intermediate Similarity	NPC473478
0.7241	Intermediate Similarity	NPC473669
0.7241	Intermediate Similarity	NPC82795
0.7241	Intermediate Similarity	NPC110710
0.7241	Intermediate Similarity	NPC223871
0.7241	Intermediate Similarity	NPC231009
0.7241	Intermediate Similarity	NPC107986
0.7241	Intermediate Similarity	NPC473651
0.7241	Intermediate Similarity	NPC103284
0.7241	Intermediate Similarity	NPC1083
0.7241	Intermediate Similarity	NPC132496
0.7241	Intermediate Similarity	NPC286338
0.7222	Intermediate Similarity	NPC166554
0.7222	Intermediate Similarity	NPC265856
0.7215	Intermediate Similarity	NPC202011
0.7204	Intermediate Similarity	NPC477921
0.7191	Intermediate Similarity	NPC233551
0.7191	Intermediate Similarity	NPC21208
0.7191	Intermediate Similarity	NPC48338
0.7191	Intermediate Similarity	NPC89001
0.7191	Intermediate Similarity	NPC20339
0.7191	Intermediate Similarity	NPC40376
0.7191	Intermediate Similarity	NPC280621
0.7188	Intermediate Similarity	NPC39996
0.7176	Intermediate Similarity	NPC297440
0.7174	Intermediate Similarity	NPC196227
0.7159	Intermediate Similarity	NPC171174
0.7159	Intermediate Similarity	NPC134807
0.7159	Intermediate Similarity	NPC219498
0.7159	Intermediate Similarity	NPC134865
0.7159	Intermediate Similarity	NPC62118
0.7159	Intermediate Similarity	NPC69082
0.7159	Intermediate Similarity	NPC240695
0.7159	Intermediate Similarity	NPC134885
0.7159	Intermediate Similarity	NPC475581
0.7159	Intermediate Similarity	NPC232555
0.7159	Intermediate Similarity	NPC103523
0.7159	Intermediate Similarity	NPC210218
0.7159	Intermediate Similarity	NPC204686
0.7159	Intermediate Similarity	NPC107717
0.7159	Intermediate Similarity	NPC142117
0.7159	Intermediate Similarity	NPC279267
0.7159	Intermediate Similarity	NPC114694
0.7159	Intermediate Similarity	NPC473687
0.7159	Intermediate Similarity	NPC308412
0.7159	Intermediate Similarity	NPC231096
0.7126	Intermediate Similarity	NPC472326
0.7126	Intermediate Similarity	NPC163093
0.7126	Intermediate Similarity	NPC219966
0.7111	Intermediate Similarity	NPC477016
0.7111	Intermediate Similarity	NPC477017
0.7111	Intermediate Similarity	NPC139418
0.7108	Intermediate Similarity	NPC471061
0.7108	Intermediate Similarity	NPC272267
0.7108	Intermediate Similarity	NPC475711
0.7097	Intermediate Similarity	NPC14961
0.7097	Intermediate Similarity	NPC36954
0.7097	Intermediate Similarity	NPC270013
0.7097	Intermediate Similarity	NPC477922
0.7097	Intermediate Similarity	NPC471142
0.7051	Intermediate Similarity	NPC26500
0.7051	Intermediate Similarity	NPC99619
0.7045	Intermediate Similarity	NPC477018
0.7045	Intermediate Similarity	NPC100921
0.7045	Intermediate Similarity	NPC120398
0.7045	Intermediate Similarity	NPC137033
0.7045	Intermediate Similarity	NPC477013
0.7045	Intermediate Similarity	NPC187529
0.7045	Intermediate Similarity	NPC471567
0.7045	Intermediate Similarity	NPC477014
0.7033	Intermediate Similarity	NPC473904
0.7033	Intermediate Similarity	NPC239517
0.7013	Intermediate Similarity	NPC323477
0.7011	Intermediate Similarity	NPC169575
0.7011	Intermediate Similarity	NPC40746
0.7011	Intermediate Similarity	NPC116543
0.7	Intermediate Similarity	NPC172821
0.7	Intermediate Similarity	NPC169511
0.7	Intermediate Similarity	NPC171135
0.7	Intermediate Similarity	NPC151403
0.7	Intermediate Similarity	NPC234077
0.7	Intermediate Similarity	NPC133730
0.7	Intermediate Similarity	NPC61257
0.7	Intermediate Similarity	NPC320569
0.7	Intermediate Similarity	NPC39754
0.7	Intermediate Similarity	NPC81045
0.7	Intermediate Similarity	NPC107848
0.7	Intermediate Similarity	NPC274446
0.7	Intermediate Similarity	NPC136879
0.7	Intermediate Similarity	NPC191929
0.7	Intermediate Similarity	NPC242364
0.7	Intermediate Similarity	NPC472008
0.7	Intermediate Similarity	NPC202672
0.7	Intermediate Similarity	NPC100454
0.7	Intermediate Similarity	NPC261952
0.7	Intermediate Similarity	NPC287164
0.6989	Remote Similarity	NPC303942
0.6989	Remote Similarity	NPC71589
0.6989	Remote Similarity	NPC470957
0.6989	Remote Similarity	NPC57405
0.6989	Remote Similarity	NPC470958
0.6989	Remote Similarity	NPC474035
0.6989	Remote Similarity	NPC81386
0.6977	Remote Similarity	NPC24417
0.6966	Remote Similarity	NPC469910
0.6966	Remote Similarity	NPC309211
0.6966	Remote Similarity	NPC477010
0.6966	Remote Similarity	NPC164393
0.6966	Remote Similarity	NPC477015
0.6957	Remote Similarity	NPC116726
0.6957	Remote Similarity	NPC30515
0.6957	Remote Similarity	NPC184463
0.6947	Remote Similarity	NPC40812
0.6941	Remote Similarity	NPC246458
0.6939	Remote Similarity	NPC469980
0.6939	Remote Similarity	NPC118902
0.6939	Remote Similarity	NPC104161
0.6932	Remote Similarity	NPC156804
0.6932	Remote Similarity	NPC243618
0.6932	Remote Similarity	NPC472958
0.6932	Remote Similarity	NPC70424
0.6932	Remote Similarity	NPC472957
0.6923	Remote Similarity	NPC295312
0.6923	Remote Similarity	NPC318963
0.6923	Remote Similarity	NPC473100
0.6923	Remote Similarity	NPC14901
0.6923	Remote Similarity	NPC40066
0.6923	Remote Similarity	NPC218927
0.6923	Remote Similarity	NPC473504
0.6923	Remote Similarity	NPC206001
0.6923	Remote Similarity	NPC81778
0.6923	Remote Similarity	NPC130359
0.6923	Remote Similarity	NPC91067
0.6923	Remote Similarity	NPC20621
0.6923	Remote Similarity	NPC474032
0.6923	Remote Similarity	NPC328653
0.6923	Remote Similarity	NPC93794
0.6923	Remote Similarity	NPC42598
0.6905	Remote Similarity	NPC473536
0.6897	Remote Similarity	NPC11332
0.6897	Remote Similarity	NPC73310
0.6897	Remote Similarity	NPC94875
0.6897	Remote Similarity	NPC475159
0.6897	Remote Similarity	NPC180363
0.6897	Remote Similarity	NPC65930
0.6897	Remote Similarity	NPC329829
0.6897	Remote Similarity	NPC229825
0.6897	Remote Similarity	NPC473780
0.6897	Remote Similarity	NPC131002
0.6897	Remote Similarity	NPC473712
0.6897	Remote Similarity	NPC145914
0.6897	Remote Similarity	NPC473529
0.6889	Remote Similarity	NPC179659
0.6889	Remote Similarity	NPC473649
0.6889	Remote Similarity	NPC159750
0.6889	Remote Similarity	NPC154097
0.6889	Remote Similarity	NPC470401
0.6889	Remote Similarity	NPC472007
0.6882	Remote Similarity	NPC476300

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 NPC47844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	2675
0.2-0.3	3703
0.3-0.4	1808
0.4-0.5	571
0.5-0.6	185
0.6-0.7	26
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6848	Remote Similarity	NPD6698	Approved
0.6848	Remote Similarity	NPD46	Approved
0.6835	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7983	Approved
0.6706	Remote Similarity	NPD4756	Discovery
0.6702	Remote Similarity	NPD5779	Approved
0.6702	Remote Similarity	NPD5778	Approved
0.6304	Remote Similarity	NPD5363	Approved
0.6264	Remote Similarity	NPD6110	Phase 1
0.625	Remote Similarity	NPD3197	Phase 1
0.6224	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4225	Approved
0.6184	Remote Similarity	NPD73	Approved
0.6162	Remote Similarity	NPD7839	Suspended
0.6146	Remote Similarity	NPD7838	Discovery
0.6129	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7154	Phase 3
0.6078	Remote Similarity	NPD5344	Discontinued
0.6076	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6371	Approved
0.6067	Remote Similarity	NPD4268	Approved
0.6067	Remote Similarity	NPD4271	Approved
0.6064	Remote Similarity	NPD5786	Approved
0.6042	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6101	Approved
0.604	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5785	Approved
0.5978	Remote Similarity	NPD4269	Approved
0.5978	Remote Similarity	NPD4270	Approved
0.5965	Remote Similarity	NPD8517	Approved
0.5965	Remote Similarity	NPD8513	Phase 3
0.5965	Remote Similarity	NPD8515	Approved
0.5965	Remote Similarity	NPD8516	Approved
0.5943	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD4819	Approved
0.5934	Remote Similarity	NPD4252	Approved
0.5934	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5368	Approved
0.5934	Remote Similarity	NPD4821	Approved
0.5934	Remote Similarity	NPD4820	Approved
0.5934	Remote Similarity	NPD4822	Approved
0.5918	Remote Similarity	NPD6411	Approved
0.5914	Remote Similarity	NPD5362	Discontinued
0.5909	Remote Similarity	NPD4632	Approved
0.5904	Remote Similarity	NPD7331	Phase 2
0.5904	Remote Similarity	NPD3704	Approved
0.5895	Remote Similarity	NPD4249	Approved
0.5893	Remote Similarity	NPD7115	Discovery
0.5888	Remote Similarity	NPD6686	Approved
0.5867	Remote Similarity	NPD66	Approved
0.5867	Remote Similarity	NPD9009	Approved
0.5867	Remote Similarity	NPD9008	Approved
0.5867	Remote Similarity	NPD9007	Approved
0.5867	Remote Similarity	NPD8960	Approved
0.5867	Remote Similarity	NPD64	Approved
0.5867	Remote Similarity	NPD72	Approved
0.5867	Remote Similarity	NPD9011	Approved
0.5867	Remote Similarity	NPD65	Approved
0.5867	Remote Similarity	NPD9010	Approved
0.5865	Remote Similarity	NPD5211	Phase 2
0.5833	Remote Similarity	NPD4250	Approved
0.5833	Remote Similarity	NPD4251	Approved
0.5818	Remote Similarity	NPD6053	Discontinued
0.5806	Remote Similarity	NPD6435	Approved
0.5794	Remote Similarity	NPD5697	Approved
0.5789	Remote Similarity	NPD1696	Phase 3
0.578	Remote Similarity	NPD4634	Approved
0.5758	Remote Similarity	NPD7515	Phase 2
0.5755	Remote Similarity	NPD5141	Approved
0.5741	Remote Similarity	NPD6881	Approved
0.5741	Remote Similarity	NPD6899	Approved
0.5739	Remote Similarity	NPD6319	Approved
0.5727	Remote Similarity	NPD6649	Approved
0.5727	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD8074	Phase 3
0.5714	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7641	Discontinued
0.5701	Remote Similarity	NPD6402	Approved
0.5701	Remote Similarity	NPD7128	Approved
0.5701	Remote Similarity	NPD6675	Approved
0.5701	Remote Similarity	NPD5739	Approved
0.5699	Remote Similarity	NPD4790	Discontinued
0.5696	Remote Similarity	NPD8959	Approved
0.5688	Remote Similarity	NPD6014	Approved
0.5688	Remote Similarity	NPD6373	Approved
0.5688	Remote Similarity	NPD6013	Approved
0.5688	Remote Similarity	NPD6372	Approved
0.5688	Remote Similarity	NPD6012	Approved
0.5688	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD8297	Approved
0.5673	Remote Similarity	NPD7639	Approved
0.5673	Remote Similarity	NPD6648	Approved
0.5673	Remote Similarity	NPD5285	Approved
0.5673	Remote Similarity	NPD5286	Approved
0.5673	Remote Similarity	NPD7640	Approved
0.5673	Remote Similarity	NPD4696	Approved
0.5648	Remote Similarity	NPD5701	Approved
0.5636	Remote Similarity	NPD7102	Approved
0.5636	Remote Similarity	NPD6883	Approved
0.5636	Remote Similarity	NPD7290	Approved
0.5631	Remote Similarity	NPD7902	Approved
0.5631	Remote Similarity	NPD4755	Approved
0.5625	Remote Similarity	NPD1694	Approved
0.5614	Remote Similarity	NPD6009	Approved
0.56	Remote Similarity	NPD6079	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