NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	281.418
LogP:	3.018
LogD:	1.822
LogS:	-3.418
# Rotatable Bonds:	6
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	3.034
Fsp3:	0.4
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:	-4.84
MDCK Permeability:	1.3848818525730167e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.804
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	58.70463943481445%
Volume Distribution (VD):	0.5
Pgp-substrate:	45.570831298828125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.535
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.092

ADMET: Excretion

Clearance (CL):	5.17
Half-life (T1/2):	0.88

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.434
Drug-inuced Liver Injury (DILI):	0.651
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.057
Carcinogencity:	0.046
Eye Corrosion:	0.01
Eye Irritation:	0.736
Respiratory Toxicity:	0.06

Download Data

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

Natural Product: NPC165197

Natural Product ID:	NPC165197
*Common Name:**	11-Dehydrosydonic Acid
IUPAC Name:	3-hydroxy-4-[(2S)-2-hydroxy-6-methylhept-6-en-2-yl]benzoic acid
Synonyms:
Standard InCHIKey:	CUAGAFVIRMPUAL-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-10(2)5-4-8-15(3,19)12-7-6-11(14(17)18)9-13(12)16/h6-7,9,16,19H,1,4-5,8H2,2-3H3,(H,17,18)/t15-/m0/s1
SMILES:	C=C(C)CCC[C@@](C)(c1ccc(cc1O)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094138
PubChem CID:	46831972
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15056914]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270557]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20415462]
NPO28107	Penicillium expansum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24024763]
NPO32607	penicillium aculeatum sd-321	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25763602]
NPO28107	Penicillium expansum	Species	Aspergillaceae	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
LD50	1
MIC	13

Activity Type	# Activity
Organism	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32.0	ug.mL-1	PMID[485718]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[485718]
NPT1843	Organism	Aeromonas hydrophila	Aeromonas hydrophila	MIC	>	32.0	ug.mL-1	PMID[485718]
NPT1844	Organism	Edwardsiella tarda	Edwardsiella tarda	MIC	>	32.0	ug.mL-1	PMID[485718]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	32.0	ug.mL-1	PMID[485718]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	32.0	ug.mL-1	PMID[485718]
NPT1845	Organism	Vibrio alginolyticus	Vibrio alginolyticus	MIC	>	32.0	ug.mL-1	PMID[485718]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	>	32.0	ug.mL-1	PMID[485718]
NPT1726	Organism	Vibrio harveyi	Vibrio harveyi	MIC	=	4.0	ug.mL-1	PMID[485718]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	=	32.0	ug.mL-1	PMID[485718]
NPT1846	Organism	Alternaria brassicae	Alternaria brassicae	MIC	>	32.0	ug.mL-1	PMID[485718]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	MIC	=	32.0	ug.mL-1	PMID[485718]
NPT1847	Organism	Gaeumannomyces graminis	Gaeumannomyces graminis	MIC	>	32.0	ug.mL-1	PMID[485718]
NPT176	Organism	Artemia salina	Artemia salina	LD50	>	10.0	ug ml-1	PMID[485718]

☑ 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 NPC165197 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	262
0.1-0.2	1347
0.2-0.3	3249
0.3-0.4	8948
0.4-0.5	10633
0.5-0.6	5287
0.6-0.7	10335
0.7-0.8	2378
0.8-0.85	201
0.85-0.9	49
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC25168
0.9826	High Similarity	NPC297193
0.9658	High Similarity	NPC117794
0.9576	High Similarity	NPC472592
0.9474	High Similarity	NPC160199
0.8968	High Similarity	NPC472591
0.8926	High Similarity	NPC275145
0.8833	High Similarity	NPC26433
0.8833	High Similarity	NPC292665
0.8833	High Similarity	NPC159760
0.8833	High Similarity	NPC179092
0.8833	High Similarity	NPC222876
0.8833	High Similarity	NPC115188
0.8833	High Similarity	NPC35856
0.8833	High Similarity	NPC244994
0.8833	High Similarity	NPC178395
0.8833	High Similarity	NPC301987
0.8833	High Similarity	NPC272454
0.8824	High Similarity	NPC184579
0.8824	High Similarity	NPC233165
0.8814	High Similarity	NPC125252
0.8803	High Similarity	NPC161304
0.879	High Similarity	NPC209959
0.877	High Similarity	NPC477153
0.873	High Similarity	NPC31539
0.8729	High Similarity	NPC312800
0.8673	High Similarity	NPC187913
0.8667	High Similarity	NPC472593
0.8629	High Similarity	NPC167055
0.8629	High Similarity	NPC240744
0.8629	High Similarity	NPC287473
0.8621	High Similarity	NPC228609
0.8596	High Similarity	NPC34715
0.8583	High Similarity	NPC41567
0.8559	High Similarity	NPC81808
0.8548	High Similarity	NPC236189
0.8538	High Similarity	NPC161632
0.8537	High Similarity	NPC283514
0.8537	High Similarity	NPC46634
0.8537	High Similarity	NPC325301
0.8537	High Similarity	NPC244351
0.8537	High Similarity	NPC327070
0.85	High Similarity	NPC269414
0.8487	Intermediate Similarity	NPC240163
0.8475	Intermediate Similarity	NPC98543
0.8475	Intermediate Similarity	NPC211421
0.8455	Intermediate Similarity	NPC198336
0.8443	Intermediate Similarity	NPC260837
0.8417	Intermediate Similarity	NPC477453
0.8413	Intermediate Similarity	NPC306765
0.8407	Intermediate Similarity	NPC13426
0.8403	Intermediate Similarity	NPC41851
0.8403	Intermediate Similarity	NPC114918
0.8403	Intermediate Similarity	NPC197513
0.8387	Intermediate Similarity	NPC307174
0.8372	Intermediate Similarity	NPC7012
0.8362	Intermediate Similarity	NPC100551
0.8361	Intermediate Similarity	NPC160235
0.8346	Intermediate Similarity	NPC71525
0.8295	Intermediate Similarity	NPC17840
0.8295	Intermediate Similarity	NPC247477
0.8293	Intermediate Similarity	NPC328485
0.8293	Intermediate Similarity	NPC285829
0.8293	Intermediate Similarity	NPC206778
0.8281	Intermediate Similarity	NPC95537
0.8281	Intermediate Similarity	NPC48248
0.8279	Intermediate Similarity	NPC474890
0.8279	Intermediate Similarity	NPC161943
0.8279	Intermediate Similarity	NPC273282
0.8268	Intermediate Similarity	NPC227741
0.8268	Intermediate Similarity	NPC295202
0.8268	Intermediate Similarity	NPC49647
0.8268	Intermediate Similarity	NPC136342
0.8264	Intermediate Similarity	NPC128825
0.8258	Intermediate Similarity	NPC229638
0.8258	Intermediate Similarity	NPC71108
0.8258	Intermediate Similarity	NPC204257
0.8258	Intermediate Similarity	NPC254832
0.8258	Intermediate Similarity	NPC267539
0.8258	Intermediate Similarity	NPC29317
0.8258	Intermediate Similarity	NPC176102
0.8254	Intermediate Similarity	NPC265910
0.8254	Intermediate Similarity	NPC91475
0.8254	Intermediate Similarity	NPC310540
0.8244	Intermediate Similarity	NPC289572
0.8244	Intermediate Similarity	NPC180261
0.8244	Intermediate Similarity	NPC37299
0.8244	Intermediate Similarity	NPC157478
0.8244	Intermediate Similarity	NPC200422
0.8244	Intermediate Similarity	NPC295406
0.824	Intermediate Similarity	NPC217756
0.824	Intermediate Similarity	NPC282577
0.8226	Intermediate Similarity	NPC164852
0.8217	Intermediate Similarity	NPC109123
0.8211	Intermediate Similarity	NPC328459
0.8211	Intermediate Similarity	NPC90522
0.8209	Intermediate Similarity	NPC4214
0.8205	Intermediate Similarity	NPC224584
0.8197	Intermediate Similarity	NPC240664
0.8195	Intermediate Similarity	NPC118919
0.8189	Intermediate Similarity	NPC262671
0.8189	Intermediate Similarity	NPC131799
0.8189	Intermediate Similarity	NPC201728
0.8189	Intermediate Similarity	NPC123506
0.8182	Intermediate Similarity	NPC474394
0.8182	Intermediate Similarity	NPC288089
0.8175	Intermediate Similarity	NPC375356
0.8174	Intermediate Similarity	NPC93831
0.8167	Intermediate Similarity	NPC242136
0.8167	Intermediate Similarity	NPC190212
0.8162	Intermediate Similarity	NPC257003
0.8158	Intermediate Similarity	NPC304873
0.8158	Intermediate Similarity	NPC25458
0.8154	Intermediate Similarity	NPC108129
0.8145	Intermediate Similarity	NPC72977
0.8142	Intermediate Similarity	NPC217621
0.814	Intermediate Similarity	NPC282923
0.8136	Intermediate Similarity	NPC95172
0.813	Intermediate Similarity	NPC94637
0.8125	Intermediate Similarity	NPC473751
0.8125	Intermediate Similarity	NPC3224
0.8125	Intermediate Similarity	NPC231774
0.8125	Intermediate Similarity	NPC160499
0.8125	Intermediate Similarity	NPC96915
0.812	Intermediate Similarity	NPC290803
0.812	Intermediate Similarity	NPC66834
0.812	Intermediate Similarity	NPC141523
0.8115	Intermediate Similarity	NPC108288
0.8115	Intermediate Similarity	NPC83718
0.811	Intermediate Similarity	NPC152525
0.811	Intermediate Similarity	NPC142956
0.811	Intermediate Similarity	NPC234890
0.811	Intermediate Similarity	NPC68756
0.811	Intermediate Similarity	NPC74507
0.8106	Intermediate Similarity	NPC263817
0.8106	Intermediate Similarity	NPC43627
0.8106	Intermediate Similarity	NPC48036
0.8099	Intermediate Similarity	NPC186933
0.8095	Intermediate Similarity	NPC477151
0.8095	Intermediate Similarity	NPC475192
0.8095	Intermediate Similarity	NPC300274
0.8095	Intermediate Similarity	NPC132518
0.8092	Intermediate Similarity	NPC205992
0.8092	Intermediate Similarity	NPC93015
0.8088	Intermediate Similarity	NPC183345
0.8083	Intermediate Similarity	NPC26615
0.8083	Intermediate Similarity	NPC231717
0.808	Intermediate Similarity	NPC241001
0.808	Intermediate Similarity	NPC190971
0.8077	Intermediate Similarity	NPC34414
0.8077	Intermediate Similarity	NPC146647
0.8077	Intermediate Similarity	NPC303910
0.807	Intermediate Similarity	NPC72729
0.8065	Intermediate Similarity	NPC232178
0.8065	Intermediate Similarity	NPC473767
0.8062	Intermediate Similarity	NPC181715
0.8062	Intermediate Similarity	NPC471530
0.806	Intermediate Similarity	NPC474726
0.806	Intermediate Similarity	NPC472308
0.806	Intermediate Similarity	NPC475955
0.8049	Intermediate Similarity	NPC121259
0.8047	Intermediate Similarity	NPC103540
0.8045	Intermediate Similarity	NPC474097
0.8045	Intermediate Similarity	NPC202225
0.8045	Intermediate Similarity	NPC204582
0.8034	Intermediate Similarity	NPC317592
0.8031	Intermediate Similarity	NPC477152
0.8031	Intermediate Similarity	NPC273683
0.8031	Intermediate Similarity	NPC135062
0.803	Intermediate Similarity	NPC110609
0.803	Intermediate Similarity	NPC242358
0.803	Intermediate Similarity	NPC246693
0.803	Intermediate Similarity	NPC470160
0.8017	Intermediate Similarity	NPC223004
0.8015	Intermediate Similarity	NPC471602
0.8015	Intermediate Similarity	NPC256463
0.8015	Intermediate Similarity	NPC199253
0.8015	Intermediate Similarity	NPC55949
0.8015	Intermediate Similarity	NPC111422
0.8015	Intermediate Similarity	NPC299405
0.8015	Intermediate Similarity	NPC136588
0.8015	Intermediate Similarity	NPC476477
0.8015	Intermediate Similarity	NPC31799
0.8015	Intermediate Similarity	NPC306835
0.8015	Intermediate Similarity	NPC29771
0.8015	Intermediate Similarity	NPC216312
0.8015	Intermediate Similarity	NPC198305
0.8015	Intermediate Similarity	NPC295339
0.8	Intermediate Similarity	NPC96024
0.8	Intermediate Similarity	NPC216297
0.8	Intermediate Similarity	NPC7151
0.8	Intermediate Similarity	NPC473662
0.8	Intermediate Similarity	NPC471452
0.8	Intermediate Similarity	NPC62272
0.8	Intermediate Similarity	NPC294964
0.8	Intermediate Similarity	NPC41263
0.8	Intermediate Similarity	NPC478121
0.8	Intermediate Similarity	NPC473744
0.8	Intermediate Similarity	NPC237225
0.7985	Intermediate Similarity	NPC142027

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 NPC165197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	906
0.2-0.3	1448
0.3-0.4	2498
0.4-0.5	2250
0.5-0.6	1193
0.6-0.7	498
0.7-0.8	95
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8362	Intermediate Similarity	NPD9266	Approved
0.8362	Intermediate Similarity	NPD74	Approved
0.8276	Intermediate Similarity	NPD9263	Approved
0.8276	Intermediate Similarity	NPD9267	Approved
0.8276	Intermediate Similarity	NPD9264	Approved
0.8264	Intermediate Similarity	NPD9493	Approved
0.8115	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD1470	Approved
0.8047	Intermediate Similarity	NPD1164	Approved
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD5408	Approved
0.8	Intermediate Similarity	NPD5405	Approved
0.8	Intermediate Similarity	NPD5404	Approved
0.8	Intermediate Similarity	NPD5406	Approved
0.7951	Intermediate Similarity	NPD9281	Approved
0.7931	Intermediate Similarity	NPD9261	Approved
0.7879	Intermediate Similarity	NPD411	Approved
0.7876	Intermediate Similarity	NPD844	Approved
0.7874	Intermediate Similarity	NPD1201	Approved
0.7836	Intermediate Similarity	NPD447	Suspended
0.7815	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD9269	Phase 2
0.7812	Intermediate Similarity	NPD9717	Approved
0.7807	Intermediate Similarity	NPD288	Approved
0.7794	Intermediate Similarity	NPD4308	Phase 3
0.7794	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD9268	Approved
0.7681	Intermediate Similarity	NPD2346	Discontinued
0.7643	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD1203	Approved
0.763	Intermediate Similarity	NPD943	Approved
0.7612	Intermediate Similarity	NPD3764	Approved
0.7607	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD230	Phase 1
0.7559	Intermediate Similarity	NPD1759	Phase 1
0.7559	Intermediate Similarity	NPD9545	Approved
0.7541	Intermediate Similarity	NPD4750	Phase 3
0.7536	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD5951	Approved
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD4307	Phase 2
0.748	Intermediate Similarity	NPD1758	Phase 1
0.7459	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4626	Approved
0.7434	Intermediate Similarity	NPD9256	Approved
0.7434	Intermediate Similarity	NPD9258	Approved
0.7431	Intermediate Similarity	NPD2534	Approved
0.7431	Intermediate Similarity	NPD2533	Approved
0.7431	Intermediate Similarity	NPD2532	Approved
0.741	Intermediate Similarity	NPD2799	Discontinued
0.741	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD2066	Phase 3
0.7361	Intermediate Similarity	NPD7390	Discontinued
0.7357	Intermediate Similarity	NPD1551	Phase 2
0.7353	Intermediate Similarity	NPD2313	Discontinued
0.7353	Intermediate Similarity	NPD3268	Approved
0.7347	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3226	Approved
0.7313	Intermediate Similarity	NPD2798	Approved
0.7308	Intermediate Similarity	NPD3019	Approved
0.7308	Intermediate Similarity	NPD2932	Approved
0.7299	Intermediate Similarity	NPD520	Approved
0.7293	Intermediate Similarity	NPD1283	Approved
0.7281	Intermediate Similarity	NPD1089	Approved
0.7281	Intermediate Similarity	NPD1086	Approved
0.7281	Intermediate Similarity	NPD1090	Approved
0.7273	Intermediate Similarity	NPD7003	Approved
0.7273	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD164	Approved
0.7273	Intermediate Similarity	NPD3750	Approved
0.7266	Intermediate Similarity	NPD1607	Approved
0.725	Intermediate Similarity	NPD846	Approved
0.725	Intermediate Similarity	NPD1932	Approved
0.725	Intermediate Similarity	NPD940	Approved
0.7241	Intermediate Similarity	NPD845	Approved
0.7222	Intermediate Similarity	NPD7635	Approved
0.7206	Intermediate Similarity	NPD6832	Phase 2
0.7194	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD800	Approved
0.719	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1930	Approved
0.719	Intermediate Similarity	NPD1929	Approved
0.7188	Intermediate Similarity	NPD256	Approved
0.7188	Intermediate Similarity	NPD255	Approved
0.7185	Intermediate Similarity	NPD1019	Discontinued
0.7179	Intermediate Similarity	NPD1693	Approved
0.7179	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD2182	Approved
0.7176	Intermediate Similarity	NPD1778	Approved
0.7176	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3300	Phase 2
0.7161	Intermediate Similarity	NPD6232	Discontinued
0.7155	Intermediate Similarity	NPD1088	Approved
0.7153	Intermediate Similarity	NPD4628	Phase 3
0.7143	Intermediate Similarity	NPD1608	Approved
0.7122	Intermediate Similarity	NPD1240	Approved
0.7121	Intermediate Similarity	NPD3496	Discontinued
0.712	Intermediate Similarity	NPD1317	Discontinued
0.7109	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5691	Approved
0.7094	Intermediate Similarity	NPD1202	Approved
0.709	Intermediate Similarity	NPD1755	Approved
0.7083	Intermediate Similarity	NPD3020	Approved
0.708	Intermediate Similarity	NPD9259	Approved
0.708	Intermediate Similarity	NPD9257	Approved
0.7075	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1281	Approved
0.7063	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD257	Approved
0.7059	Intermediate Similarity	NPD258	Approved
0.705	Intermediate Similarity	NPD6663	Approved
0.7042	Intermediate Similarity	NPD1510	Phase 2
0.704	Intermediate Similarity	NPD2329	Discontinued
0.7034	Intermediate Similarity	NPD8166	Discontinued
0.7025	Intermediate Similarity	NPD7473	Discontinued
0.7018	Intermediate Similarity	NPD1087	Approved
0.7015	Intermediate Similarity	NPD3972	Approved
0.7008	Intermediate Similarity	NPD9508	Approved
0.7007	Intermediate Similarity	NPD5736	Approved
0.7007	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD7458	Discontinued
0.6993	Remote Similarity	NPD6100	Approved
0.6993	Remote Similarity	NPD6099	Approved
0.6992	Remote Similarity	NPD1237	Approved
0.6985	Remote Similarity	NPD3266	Approved
0.6985	Remote Similarity	NPD3267	Approved
0.6984	Remote Similarity	NPD3022	Approved
0.6984	Remote Similarity	NPD3021	Approved
0.6975	Remote Similarity	NPD2859	Approved
0.6975	Remote Similarity	NPD1809	Phase 2
0.6975	Remote Similarity	NPD2860	Approved
0.6966	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD182	Clinical (unspecified phase)
0.696	Remote Similarity	NPD2342	Discontinued
0.6959	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2344	Approved
0.6934	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7819	Suspended
0.6923	Remote Similarity	NPD6671	Approved
0.6923	Remote Similarity	NPD1239	Approved
0.6923	Remote Similarity	NPD3748	Approved
0.6917	Remote Similarity	NPD17	Approved
0.6906	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2933	Approved
0.6891	Remote Similarity	NPD2934	Approved
0.6889	Remote Similarity	NPD1481	Phase 2
0.6883	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1445	Approved
0.688	Remote Similarity	NPD1444	Approved
0.6879	Remote Similarity	NPD825	Approved
0.6879	Remote Similarity	NPD826	Approved
0.6879	Remote Similarity	NPD2979	Phase 3
0.6875	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6190	Approved
0.687	Remote Similarity	NPD9568	Approved
0.6866	Remote Similarity	NPD3026	Approved
0.6866	Remote Similarity	NPD3023	Approved
0.686	Remote Similarity	NPD9495	Approved
0.6846	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3025	Approved
0.6842	Remote Similarity	NPD1651	Approved
0.6842	Remote Similarity	NPD3024	Approved
0.6842	Remote Similarity	NPD6599	Discontinued
0.6839	Remote Similarity	NPD7768	Phase 2
0.6838	Remote Similarity	NPD4749	Approved
0.6832	Remote Similarity	NPD5844	Phase 1
0.6824	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5277	Phase 2
0.6818	Remote Similarity	NPD1465	Phase 2
0.6815	Remote Similarity	NPD422	Phase 1
0.6815	Remote Similarity	NPD1611	Approved
0.6815	Remote Similarity	NPD1535	Discovery
0.6814	Remote Similarity	NPD9491	Approved
0.6807	Remote Similarity	NPD8150	Discontinued
0.6803	Remote Similarity	NPD1196	Approved
0.68	Remote Similarity	NPD6273	Approved
0.6797	Remote Similarity	NPD2672	Discontinued
0.6797	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3749	Approved
0.6791	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3225	Approved
0.6786	Remote Similarity	NPD7008	Discontinued
0.6781	Remote Similarity	NPD1549	Phase 2
0.6779	Remote Similarity	NPD1511	Approved
0.6779	Remote Similarity	NPD1543	Discontinued
0.6777	Remote Similarity	NPD1566	Phase 3
0.6777	Remote Similarity	NPD1565	Approved
0.6777	Remote Similarity	NPD1564	Approved
0.6774	Remote Similarity	NPD5402	Approved
0.6763	Remote Similarity	NPD9569	Approved
0.6757	Remote Similarity	NPD2309	Approved
0.6748	Remote Similarity	NPD1242	Phase 1
0.6738	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD9279	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