NPASS Compound

Structure

NPC475865 OpenBabel07101718242D 30 34 0 0 1 0 0 0 0 0999 V2000 2.8913 -5.1509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2240 -5.1509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6832 1.1620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4322 1.1620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1100 -2.4216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0054 -2.4216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0482 -0.1477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9328 -0.1477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5299 -4.2783 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5855 -4.2783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1977 -2.6660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9176 -2.6660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3544 -1.5093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2391 -1.5093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5299 -1.9982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5855 -1.9982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1977 -3.6105 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9176 -3.6105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6866 -0.8415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4288 -0.8415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7744 -1.0859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3410 -1.0859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0703 -3.9719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0451 -3.9719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4387 0.2497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6767 0.2497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1959 -1.0806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0806 -1.0806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1154 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 11 2 0 0 0 0 5 13 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 27 1 0 0 0 0 7 29 1 0 0 0 0 8 28 1 0 0 0 0 8 30 1 0 0 0 0 9 1 1 6 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 2 1 6 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 13 27 1 0 0 0 0 14 20 2 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 21 2 0 0 0 0 16 22 2 0 0 0 0 17 23 1 1 0 0 0 18 24 2 0 0 0 0 19 21 1 0 0 0 0 19 29 1 0 0 0 0 20 22 1 0 0 0 0 20 30 1 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.13
Volume:	398.152
LogP:	2.588
LogD:	2.366
LogS:	-4.234
# Rotatable Bonds:	2
TPSA:	92.68
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.8
Synthetic Accessibility Score:	4.055
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.722
MDCK Permeability:	3.662936796899885e-05
Pgp-inhibitor:	0.624
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	93.4295883178711%
Volume Distribution (VD):	0.724
Pgp-substrate:	4.005927562713623%

ADMET: Metabolism

CYP1A2-inhibitor:	0.291
CYP1A2-substrate:	0.9
CYP2C19-inhibitor:	0.851
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.185
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.388
CYP2D6-substrate:	0.447
CYP3A4-inhibitor:	0.937
CYP3A4-substrate:	0.656

ADMET: Excretion

Clearance (CL):	8.537
Half-life (T1/2):	0.092

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.482
AMES Toxicity:	0.186
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.137
Skin Sensitization:	0.04
Carcinogencity:	0.894
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.468

Download Data

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

Natural Product: NPC475865

Natural Product ID:	NPC475865
*Common Name:**	Schisantherin Q
IUPAC Name:	n.a.
Synonyms:	Schisantherin Q
Standard InCHIKey:	SEBKCRYGYKNELU-KEYDSSBGSA-N
Standard InCHI:	InChI=1S/C22H22O8/c1-9-10(2)18(24)12-6-14-20(30-8-28-14)22(26-4)16(12)15-11(17(9)23)5-13-19(21(15)25-3)29-7-27-13/h5-6,9-10,17,23H,7-8H2,1-4H3/t9-,10+,17+/m1/s1
SMILES:	CC1C(C(=O)C2=CC3=C(C(=C2C4=C(C5=C(C=C4C1O)OCO5)OC)OC)OCO3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517629
PubChem CID:	44567620
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	211590.0	nM	PMID[527282]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	45890.0	nM	PMID[527282]
NPT2	Others	Unspecified		Ratio	=	6.41	n.a.	PMID[527282]

☑ 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 NPC475865 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	378
0.1-0.2	1517
0.2-0.3	3392
0.3-0.4	8400
0.4-0.5	10449
0.5-0.6	3463
0.6-0.7	5744
0.7-0.8	7974
0.8-0.85	1244
0.85-0.9	119
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9551	High Similarity	NPC474770
0.9371	High Similarity	NPC469475
0.9371	High Similarity	NPC469518
0.9363	High Similarity	NPC325122
0.9351	High Similarity	NPC220577
0.9317	High Similarity	NPC471180
0.9264	High Similarity	NPC178737
0.9264	High Similarity	NPC469506
0.9187	High Similarity	NPC61141
0.9177	High Similarity	NPC474990
0.9146	High Similarity	NPC471181
0.9114	High Similarity	NPC477380
0.9108	High Similarity	NPC312763
0.9108	High Similarity	NPC348849
0.9108	High Similarity	NPC178195
0.9103	High Similarity	NPC104353
0.9091	High Similarity	NPC304821
0.908	High Similarity	NPC79322
0.9068	High Similarity	NPC469512
0.9057	High Similarity	NPC477885
0.9006	High Similarity	NPC191352
0.9006	High Similarity	NPC258322
0.8981	High Similarity	NPC272566
0.8976	High Similarity	NPC477881
0.8963	High Similarity	NPC311912
0.8961	High Similarity	NPC87295
0.8957	High Similarity	NPC477884
0.8924	High Similarity	NPC24562
0.8917	High Similarity	NPC303519
0.8909	High Similarity	NPC88557
0.8902	High Similarity	NPC118162
0.8902	High Similarity	NPC320471
0.8902	High Similarity	NPC83049
0.8896	High Similarity	NPC475868
0.8875	High Similarity	NPC469474
0.8868	High Similarity	NPC198461
0.8855	High Similarity	NPC477883
0.8854	High Similarity	NPC473989
0.8841	High Similarity	NPC475738
0.8834	High Similarity	NPC76687
0.8831	High Similarity	NPC172171
0.8831	High Similarity	NPC239254
0.882	High Similarity	NPC207584
0.882	High Similarity	NPC19947
0.8817	High Similarity	NPC477882
0.8817	High Similarity	NPC477880
0.8797	High Similarity	NPC62354
0.879	High Similarity	NPC85141
0.8788	High Similarity	NPC474042
0.8788	High Similarity	NPC174734
0.8773	High Similarity	NPC319749
0.8766	High Similarity	NPC324962
0.8758	High Similarity	NPC237946
0.8758	High Similarity	NPC32373
0.8758	High Similarity	NPC473323
0.875	High Similarity	NPC287504
0.8742	High Similarity	NPC151425
0.8726	High Similarity	NPC316676
0.8726	High Similarity	NPC325720
0.872	High Similarity	NPC280778
0.8712	High Similarity	NPC239818
0.8712	High Similarity	NPC218471
0.8704	High Similarity	NPC167595
0.8701	High Similarity	NPC229172
0.8701	High Similarity	NPC103637
0.8701	High Similarity	NPC230538
0.8701	High Similarity	NPC36531
0.8696	High Similarity	NPC238834
0.8696	High Similarity	NPC476065
0.869	High Similarity	NPC38438
0.8688	High Similarity	NPC77237
0.8688	High Similarity	NPC297271
0.8688	High Similarity	NPC308739
0.8688	High Similarity	NPC53669
0.8688	High Similarity	NPC474514
0.8688	High Similarity	NPC245948
0.8688	High Similarity	NPC16791
0.8688	High Similarity	NPC126405
0.8688	High Similarity	NPC217708
0.8683	High Similarity	NPC117911
0.8679	High Similarity	NPC234152
0.8659	High Similarity	NPC288149
0.8659	High Similarity	NPC209411
0.8659	High Similarity	NPC239890
0.865	High Similarity	NPC215375
0.865	High Similarity	NPC62518
0.8647	High Similarity	NPC473713
0.8647	High Similarity	NPC196771
0.8639	High Similarity	NPC474568
0.8634	High Similarity	NPC25127
0.8634	High Similarity	NPC57211
0.8634	High Similarity	NPC273578
0.8634	High Similarity	NPC473425
0.8631	High Similarity	NPC212748
0.8625	High Similarity	NPC56184
0.8623	High Similarity	NPC42230
0.8616	High Similarity	NPC316989
0.8614	High Similarity	NPC475953
0.8608	High Similarity	NPC252281
0.8608	High Similarity	NPC477375
0.8608	High Similarity	NPC198129
0.8608	High Similarity	NPC327352
0.8606	High Similarity	NPC125991
0.8606	High Similarity	NPC469575
0.8606	High Similarity	NPC249070
0.8605	High Similarity	NPC170203
0.8599	High Similarity	NPC252286
0.8599	High Similarity	NPC154971
0.8598	High Similarity	NPC268718
0.8598	High Similarity	NPC91634
0.8598	High Similarity	NPC96593
0.8598	High Similarity	NPC150943
0.8598	High Similarity	NPC24627
0.8598	High Similarity	NPC119910
0.8589	High Similarity	NPC475592
0.8571	High Similarity	NPC104728
0.8571	High Similarity	NPC35544
0.8571	High Similarity	NPC211309
0.8571	High Similarity	NPC52623
0.8571	High Similarity	NPC308555
0.8571	High Similarity	NPC474606
0.8562	High Similarity	NPC32079
0.8562	High Similarity	NPC477700
0.8562	High Similarity	NPC475756
0.8562	High Similarity	NPC224472
0.8553	High Similarity	NPC477374
0.8553	High Similarity	NPC477698
0.8553	High Similarity	NPC322426
0.8553	High Similarity	NPC477376
0.8545	High Similarity	NPC260640
0.8545	High Similarity	NPC295009
0.8538	High Similarity	NPC472723
0.8537	High Similarity	NPC474043
0.8537	High Similarity	NPC125713
0.8535	High Similarity	NPC197352
0.8535	High Similarity	NPC166506
0.8535	High Similarity	NPC110763
0.8535	High Similarity	NPC189239
0.8529	High Similarity	NPC166674
0.8529	High Similarity	NPC263119
0.8529	High Similarity	NPC46640
0.8529	High Similarity	NPC219600
0.8529	High Similarity	NPC34436
0.8528	High Similarity	NPC301897
0.8528	High Similarity	NPC261090
0.8519	High Similarity	NPC136757
0.8519	High Similarity	NPC303950
0.8519	High Similarity	NPC478213
0.8514	High Similarity	NPC475360
0.8512	High Similarity	NPC474948
0.8509	High Similarity	NPC228662
0.8509	High Similarity	NPC471154
0.8509	High Similarity	NPC279061
0.8503	High Similarity	NPC165720
0.8503	High Similarity	NPC474647
0.8494	Intermediate Similarity	NPC473445
0.8494	Intermediate Similarity	NPC22130
0.8494	Intermediate Similarity	NPC42797
0.8494	Intermediate Similarity	NPC116838
0.8494	Intermediate Similarity	NPC148273
0.8485	Intermediate Similarity	NPC225624
0.8485	Intermediate Similarity	NPC285973
0.8481	Intermediate Similarity	NPC321958
0.8481	Intermediate Similarity	NPC30890
0.8481	Intermediate Similarity	NPC224687
0.8481	Intermediate Similarity	NPC321696
0.8481	Intermediate Similarity	NPC296575
0.848	Intermediate Similarity	NPC146803
0.848	Intermediate Similarity	NPC290304
0.848	Intermediate Similarity	NPC236327
0.8476	Intermediate Similarity	NPC190020
0.8476	Intermediate Similarity	NPC163527
0.8476	Intermediate Similarity	NPC472860
0.8476	Intermediate Similarity	NPC220462
0.8476	Intermediate Similarity	NPC115281
0.8476	Intermediate Similarity	NPC84935
0.8476	Intermediate Similarity	NPC181168
0.8476	Intermediate Similarity	NPC77679
0.8471	Intermediate Similarity	NPC18211
0.8471	Intermediate Similarity	NPC475000
0.8471	Intermediate Similarity	NPC157522
0.8471	Intermediate Similarity	NPC121661
0.8471	Intermediate Similarity	NPC73467
0.8471	Intermediate Similarity	NPC143092
0.8471	Intermediate Similarity	NPC235575
0.8466	Intermediate Similarity	NPC254163
0.8466	Intermediate Similarity	NPC478238
0.8466	Intermediate Similarity	NPC79998
0.8462	Intermediate Similarity	NPC229687
0.8457	Intermediate Similarity	NPC153008
0.8457	Intermediate Similarity	NPC148497
0.8452	Intermediate Similarity	NPC119589
0.8447	Intermediate Similarity	NPC225854
0.8447	Intermediate Similarity	NPC210642
0.8447	Intermediate Similarity	NPC13985
0.8447	Intermediate Similarity	NPC164082
0.8443	Intermediate Similarity	NPC471286
0.8443	Intermediate Similarity	NPC88043
0.8443	Intermediate Similarity	NPC116759
0.8443	Intermediate Similarity	NPC291977

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 NPC475865 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	919
0.2-0.3	1782
0.3-0.4	2684
0.4-0.5	1911
0.5-0.6	967
0.6-0.7	406
0.7-0.8	136
0.8-0.85	14
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8758	High Similarity	NPD4967	Phase 2
0.8758	High Similarity	NPD4965	Approved
0.8758	High Similarity	NPD4966	Approved
0.8688	High Similarity	NPD37	Approved
0.8623	High Similarity	NPD3818	Discontinued
0.8537	High Similarity	NPD6234	Discontinued
0.8375	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7199	Phase 2
0.8294	Intermediate Similarity	NPD7228	Approved
0.8235	Intermediate Similarity	NPD7473	Discontinued
0.8198	Intermediate Similarity	NPD7074	Phase 3
0.8166	Intermediate Similarity	NPD6232	Discontinued
0.814	Intermediate Similarity	NPD5844	Phase 1
0.814	Intermediate Similarity	NPD7054	Approved
0.8118	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7472	Approved
0.8084	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD3882	Suspended
0.8047	Intermediate Similarity	NPD5494	Approved
0.8036	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD7240	Approved
0.7964	Intermediate Similarity	NPD1465	Phase 2
0.7963	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7808	Phase 3
0.7943	Intermediate Similarity	NPD6797	Phase 2
0.7921	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7251	Discontinued
0.7898	Intermediate Similarity	NPD6559	Discontinued
0.7861	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6166	Phase 2
0.7857	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2801	Approved
0.7811	Intermediate Similarity	NPD3817	Phase 2
0.7784	Intermediate Similarity	NPD4380	Phase 2
0.7751	Intermediate Similarity	NPD7819	Suspended
0.774	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD3926	Phase 2
0.7697	Intermediate Similarity	NPD7685	Pre-registration
0.7697	Intermediate Similarity	NPD2533	Approved
0.7697	Intermediate Similarity	NPD2534	Approved
0.7697	Intermediate Similarity	NPD2532	Approved
0.7654	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6959	Discontinued
0.7578	Intermediate Similarity	NPD1510	Phase 2
0.7571	Intermediate Similarity	NPD3751	Discontinued
0.7547	Intermediate Similarity	NPD1240	Approved
0.753	Intermediate Similarity	NPD1511	Approved
0.7514	Intermediate Similarity	NPD7075	Discontinued
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD230	Phase 1
0.7486	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD6801	Discontinued
0.7473	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD919	Approved
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.746	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4628	Phase 3
0.7455	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3750	Approved
0.7453	Intermediate Similarity	NPD1607	Approved
0.7443	Intermediate Similarity	NPD3787	Discontinued
0.7442	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1512	Approved
0.7439	Intermediate Similarity	NPD1549	Phase 2
0.7425	Intermediate Similarity	NPD6799	Approved
0.7423	Intermediate Similarity	NPD2796	Approved
0.7414	Intermediate Similarity	NPD3749	Approved
0.7412	Intermediate Similarity	NPD7458	Discontinued
0.7399	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5402	Approved
0.7391	Intermediate Similarity	NPD8434	Phase 2
0.7385	Intermediate Similarity	NPD8151	Discontinued
0.7381	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6599	Discontinued
0.7353	Intermediate Similarity	NPD1653	Approved
0.7329	Intermediate Similarity	NPD943	Approved
0.7326	Intermediate Similarity	NPD7411	Suspended
0.7322	Intermediate Similarity	NPD8312	Approved
0.7322	Intermediate Similarity	NPD8313	Approved
0.7306	Intermediate Similarity	NPD7680	Approved
0.7303	Intermediate Similarity	NPD5242	Approved
0.7299	Intermediate Similarity	NPD5353	Approved
0.729	Intermediate Similarity	NPD3705	Approved
0.7267	Intermediate Similarity	NPD7028	Phase 2
0.7256	Intermediate Similarity	NPD3748	Approved
0.7254	Intermediate Similarity	NPD5005	Approved
0.7254	Intermediate Similarity	NPD5006	Approved
0.7247	Intermediate Similarity	NPD7229	Phase 3
0.724	Intermediate Similarity	NPD6782	Approved
0.724	Intermediate Similarity	NPD6781	Approved
0.724	Intermediate Similarity	NPD6777	Approved
0.724	Intermediate Similarity	NPD6778	Approved
0.724	Intermediate Similarity	NPD6779	Approved
0.724	Intermediate Similarity	NPD6780	Approved
0.724	Intermediate Similarity	NPD6776	Approved
0.7212	Intermediate Similarity	NPD2935	Discontinued
0.7205	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6190	Approved
0.7193	Intermediate Similarity	NPD5403	Approved
0.7193	Intermediate Similarity	NPD920	Approved
0.7186	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2800	Approved
0.7176	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5710	Approved
0.7151	Intermediate Similarity	NPD5711	Approved
0.7135	Intermediate Similarity	NPD4420	Approved
0.7128	Intermediate Similarity	NPD7696	Phase 3
0.7128	Intermediate Similarity	NPD7697	Approved
0.7128	Intermediate Similarity	NPD7698	Approved
0.7128	Intermediate Similarity	NPD7435	Discontinued
0.7125	Intermediate Similarity	NPD9494	Approved
0.7118	Intermediate Similarity	NPD7390	Discontinued
0.7117	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1613	Approved
0.711	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3226	Approved
0.7108	Intermediate Similarity	NPD6100	Approved
0.7108	Intermediate Similarity	NPD6099	Approved
0.7095	Intermediate Similarity	NPD8127	Discontinued
0.7092	Intermediate Similarity	NPD7870	Phase 2
0.7092	Intermediate Similarity	NPD7871	Phase 2
0.7083	Intermediate Similarity	NPD1243	Approved
0.7083	Intermediate Similarity	NPD6674	Discontinued
0.7076	Intermediate Similarity	NPD5401	Approved
0.7076	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD447	Suspended
0.7066	Intermediate Similarity	NPD7266	Discontinued
0.7066	Intermediate Similarity	NPD2344	Approved
0.7063	Intermediate Similarity	NPD2798	Approved
0.7062	Intermediate Similarity	NPD7768	Phase 2
0.7062	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8455	Phase 2
0.703	Intermediate Similarity	NPD6651	Approved
0.7029	Intermediate Similarity	NPD6386	Approved
0.7029	Intermediate Similarity	NPD6385	Approved
0.7018	Intermediate Similarity	NPD4357	Discontinued
0.6994	Remote Similarity	NPD3764	Approved
0.699	Remote Similarity	NPD6823	Phase 2
0.6987	Remote Similarity	NPD9268	Approved
0.6985	Remote Similarity	NPD7701	Phase 2
0.6984	Remote Similarity	NPD6842	Approved
0.6984	Remote Similarity	NPD6841	Approved
0.6984	Remote Similarity	NPD6843	Phase 3
0.6981	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6535	Approved
0.6979	Remote Similarity	NPD6534	Approved
0.6977	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1933	Approved
0.6965	Remote Similarity	NPD7801	Approved
0.6964	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2799	Discontinued
0.6946	Remote Similarity	NPD7930	Approved
0.6941	Remote Similarity	NPD7003	Approved
0.6941	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1876	Approved
0.6936	Remote Similarity	NPD6273	Approved
0.6931	Remote Similarity	NPD8150	Discontinued
0.6927	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD9269	Phase 2
0.6915	Remote Similarity	NPD7874	Approved
0.6915	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3018	Phase 2
0.691	Remote Similarity	NPD5978	Approved
0.691	Remote Similarity	NPD5977	Approved
0.6905	Remote Similarity	NPD2438	Suspended
0.6905	Remote Similarity	NPD1551	Phase 2
0.6901	Remote Similarity	NPD2309	Approved
0.6898	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5953	Discontinued
0.6881	Remote Similarity	NPD7783	Phase 2
0.6881	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1357	Approved
0.6872	Remote Similarity	NPD7700	Phase 2
0.6872	Remote Similarity	NPD7699	Phase 2
0.6871	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6355	Discontinued
0.6864	Remote Similarity	NPD2346	Discontinued
0.6859	Remote Similarity	NPD5536	Phase 2
0.6854	Remote Similarity	NPD5761	Phase 2
0.6854	Remote Similarity	NPD5760	Phase 2
0.6845	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4110	Phase 3
0.6834	Remote Similarity	NPD8320	Phase 1
0.6834	Remote Similarity	NPD8319	Approved
0.6832	Remote Similarity	NPD1283	Approved
0.6813	Remote Similarity	NPD3972	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