NPASS Compound

Structure

NPC55239 OpenBabel07101718242D 29 31 0 0 1 0 0 0 0 0999 V2000 1.5902 -4.1695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5178 -3.8642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8072 0.7522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5924 1.4372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5015 1.8715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1193 2.3058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9045 -2.5895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8402 -1.3700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3700 -1.3700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4343 -2.5895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2195 -3.2745 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9045 -1.6208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4343 -1.6208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0910 -0.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6208 -0.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2195 -0.9357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2507 -0.9357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4702 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4060 0.2507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9357 0.2507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2507 -3.2745 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0267 -0.1835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7852 0.6850 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3772 -4.2350 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5565 -0.1835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6567 1.1865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1865 1.1865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3700 1.3700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 22 1 6 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 20 2 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 2 1 6 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.18
Volume:	409.112
LogP:	2.859
LogD:	2.795
LogS:	-3.204
# Rotatable Bonds:	4
TPSA:	97.61
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.719
Synthetic Accessibility Score:	3.618
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.879
MDCK Permeability:	1.4265213394537568e-05
Pgp-inhibitor:	0.24
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	87.46015167236328%
Volume Distribution (VD):	0.576
Pgp-substrate:	16.640579223632812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.201
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.771
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.711
CYP3A4-inhibitor:	0.473
CYP3A4-substrate:	0.571

ADMET: Excretion

Clearance (CL):	10.587
Half-life (T1/2):	0.293

ADMET: Toxicity

hERG Blockers:	0.26
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.227
Maximum Recommended Daily Dose:	0.174
Skin Sensitization:	0.512
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.194
Respiratory Toxicity:	0.64

Download Data

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

Natural Product: NPC55239

Natural Product ID:	NPC55239
*Common Name:**	Marlignan K
IUPAC Name:	n.a.
Synonyms:	Marlignan K
Standard InCHIKey:	TZFVHJQZGJSADS-SAHAZLINSA-N
Standard InCHI:	InChI=1S/C22H28O7/c1-11-7-12-8-14(23)19(27-4)18(24)16(12)17-13(10-22(11,2)25)9-15(26-3)20(28-5)21(17)29-6/h8-9,11,23-25H,7,10H2,1-6H3/t11-,22-/m0/s1
SMILES:	COc1c(OC)cc2c(c1OC)c1c(cc(c(c1O)OC)O)C[C@@H]([C@@](C2)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095178
PubChem CID:	46832526
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
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[19228000]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19228000]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20462233]
NPO2766	Schisandra wilsoniana	Species	Schisandraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23327759]
NPO2766	Schisandra wilsoniana	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	=	14.8	ug.mL-1	PMID[523708]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	1.9	ug.mL-1	PMID[523708]
NPT27	Others	Unspecified		TI	=	7.7	n.a.	PMID[523708]

☑ 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 NPC55239 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	449
0.1-0.2	1673
0.2-0.3	4645
0.3-0.4	12637
0.4-0.5	5561
0.5-0.6	4072
0.6-0.7	7564
0.7-0.8	4614
0.8-0.85	792
0.85-0.9	503
0.9-0.95	164
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC180602
1.0	High Similarity	NPC214853
1.0	High Similarity	NPC240279
0.9922	High Similarity	NPC7515
0.9922	High Similarity	NPC276026
0.9922	High Similarity	NPC469659
0.9922	High Similarity	NPC555
0.9922	High Similarity	NPC188378
0.9922	High Similarity	NPC56764
0.9922	High Similarity	NPC206737
0.9922	High Similarity	NPC289258
0.9769	High Similarity	NPC133025
0.9695	High Similarity	NPC46277
0.9695	High Similarity	NPC3072
0.9695	High Similarity	NPC301765
0.9695	High Similarity	NPC156948
0.9695	High Similarity	NPC86605
0.9621	High Similarity	NPC471183
0.9612	High Similarity	NPC102256
0.9457	High Similarity	NPC126836
0.9407	High Similarity	NPC184641
0.9407	High Similarity	NPC133934
0.9407	High Similarity	NPC184684
0.9407	High Similarity	NPC470917
0.9389	High Similarity	NPC32778
0.9338	High Similarity	NPC469630
0.9323	High Similarity	NPC143139
0.9323	High Similarity	NPC202846
0.9318	High Similarity	NPC209199
0.9318	High Similarity	NPC125649
0.9313	High Similarity	NPC6451
0.9302	High Similarity	NPC283114
0.9302	High Similarity	NPC207702
0.9302	High Similarity	NPC154866
0.9302	High Similarity	NPC149008
0.9297	High Similarity	NPC76451
0.927	High Similarity	NPC73467
0.927	High Similarity	NPC87883
0.927	High Similarity	NPC121661
0.9248	High Similarity	NPC10314
0.9248	High Similarity	NPC294884
0.9248	High Similarity	NPC158142
0.9248	High Similarity	NPC108198
0.9248	High Similarity	NPC69029
0.9248	High Similarity	NPC200557
0.9248	High Similarity	NPC313081
0.9237	High Similarity	NPC474356
0.9237	High Similarity	NPC232275
0.9237	High Similarity	NPC45715
0.9237	High Similarity	NPC12275
0.9225	High Similarity	NPC236791
0.9225	High Similarity	NPC293054
0.9225	High Similarity	NPC127587
0.9225	High Similarity	NPC324112
0.9225	High Similarity	NPC169474
0.9225	High Similarity	NPC266555
0.9225	High Similarity	NPC246620
0.9225	High Similarity	NPC74817
0.9225	High Similarity	NPC82679
0.9225	High Similarity	NPC124452
0.9225	High Similarity	NPC282000
0.9225	High Similarity	NPC159968
0.9203	High Similarity	NPC197352
0.9203	High Similarity	NPC189239
0.9203	High Similarity	NPC166506
0.9203	High Similarity	NPC110763
0.9185	High Similarity	NPC212942
0.9185	High Similarity	NPC114171
0.9185	High Similarity	NPC184613
0.9185	High Similarity	NPC79622
0.9185	High Similarity	NPC230124
0.9185	High Similarity	NPC29868
0.9185	High Similarity	NPC201404
0.9185	High Similarity	NPC6300
0.9185	High Similarity	NPC53722
0.9185	High Similarity	NPC290714
0.9173	High Similarity	NPC160697
0.9167	High Similarity	NPC161958
0.9167	High Similarity	NPC14224
0.916	High Similarity	NPC234488
0.916	High Similarity	NPC224157
0.916	High Similarity	NPC311680
0.916	High Similarity	NPC192687
0.916	High Similarity	NPC51840
0.916	High Similarity	NPC299221
0.9154	High Similarity	NPC28765
0.9147	High Similarity	NPC44748
0.9147	High Similarity	NPC18924
0.9147	High Similarity	NPC223136
0.9147	High Similarity	NPC28730
0.9147	High Similarity	NPC78974
0.9147	High Similarity	NPC214406
0.9147	High Similarity	NPC103823
0.9147	High Similarity	NPC223953
0.9137	High Similarity	NPC154971
0.9137	High Similarity	NPC474054
0.9137	High Similarity	NPC252286
0.9118	High Similarity	NPC308768
0.9118	High Similarity	NPC12668
0.9111	High Similarity	NPC22902
0.9111	High Similarity	NPC242715
0.9111	High Similarity	NPC56329
0.9104	High Similarity	NPC256262
0.9104	High Similarity	NPC241241
0.9091	High Similarity	NPC184928
0.9091	High Similarity	NPC15543
0.9091	High Similarity	NPC474017
0.9091	High Similarity	NPC141493
0.9084	High Similarity	NPC58164
0.9084	High Similarity	NPC10225
0.9084	High Similarity	NPC190144
0.9077	High Similarity	NPC252131
0.907	High Similarity	NPC472093
0.907	High Similarity	NPC251855
0.907	High Similarity	NPC17943
0.907	High Similarity	NPC60885
0.907	High Similarity	NPC299584
0.907	High Similarity	NPC221077
0.907	High Similarity	NPC475169
0.907	High Similarity	NPC234400
0.907	High Similarity	NPC57490
0.907	High Similarity	NPC203133
0.907	High Similarity	NPC265483
0.907	High Similarity	NPC116907
0.907	High Similarity	NPC105925
0.907	High Similarity	NPC208950
0.907	High Similarity	NPC193544
0.907	High Similarity	NPC298757
0.907	High Similarity	NPC82483
0.907	High Similarity	NPC117214
0.907	High Similarity	NPC233410
0.9044	High Similarity	NPC105847
0.9044	High Similarity	NPC220344
0.9044	High Similarity	NPC243996
0.9044	High Similarity	NPC243759
0.9044	High Similarity	NPC218131
0.9044	High Similarity	NPC275061
0.9044	High Similarity	NPC132804
0.9037	High Similarity	NPC30632
0.9037	High Similarity	NPC270456
0.9037	High Similarity	NPC162659
0.9037	High Similarity	NPC248727
0.9037	High Similarity	NPC205442
0.9037	High Similarity	NPC265433
0.9023	High Similarity	NPC204215
0.9023	High Similarity	NPC127624
0.9023	High Similarity	NPC175067
0.9014	High Similarity	NPC470916
0.9008	High Similarity	NPC266691
0.8992	High Similarity	NPC5796
0.8992	High Similarity	NPC206487
0.8986	High Similarity	NPC175838
0.8986	High Similarity	NPC229172
0.8986	High Similarity	NPC103637
0.8986	High Similarity	NPC230538
0.8986	High Similarity	NPC36531
0.8978	High Similarity	NPC109240
0.8971	High Similarity	NPC151656
0.8971	High Similarity	NPC201145
0.8971	High Similarity	NPC266006
0.8971	High Similarity	NPC230919
0.8971	High Similarity	NPC266453
0.8971	High Similarity	NPC90615
0.8971	High Similarity	NPC200935
0.8971	High Similarity	NPC73535
0.8971	High Similarity	NPC272157
0.8971	High Similarity	NPC25111
0.8971	High Similarity	NPC6262
0.8955	High Similarity	NPC158331
0.8947	High Similarity	NPC469907
0.8944	High Similarity	NPC474347
0.8944	High Similarity	NPC474393
0.8939	High Similarity	NPC212015
0.8939	High Similarity	NPC170844
0.8939	High Similarity	NPC476968
0.8931	High Similarity	NPC236760
0.8931	High Similarity	NPC21563
0.8931	High Similarity	NPC5428
0.8921	High Similarity	NPC324962
0.8915	High Similarity	NPC136319
0.8915	High Similarity	NPC95168
0.8915	High Similarity	NPC197757
0.8915	High Similarity	NPC228922
0.8915	High Similarity	NPC84086
0.8915	High Similarity	NPC121115
0.8915	High Similarity	NPC282496
0.8915	High Similarity	NPC233526
0.8905	High Similarity	NPC260741
0.8905	High Similarity	NPC127218
0.8905	High Similarity	NPC6369
0.8905	High Similarity	NPC30951
0.8905	High Similarity	NPC319647
0.8905	High Similarity	NPC70682
0.8905	High Similarity	NPC25966
0.8905	High Similarity	NPC245207
0.8897	High Similarity	NPC227503
0.8897	High Similarity	NPC300846
0.8897	High Similarity	NPC476639
0.8897	High Similarity	NPC230734
0.8897	High Similarity	NPC474639

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 NPC55239 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	950
0.2-0.3	1860
0.3-0.4	2815
0.4-0.5	1549
0.5-0.6	902
0.6-0.7	585
0.7-0.8	100
0.8-0.85	7
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8939	High Similarity	NPD3027	Phase 3
0.8647	High Similarity	NPD1530	Clinical (unspecified phase)
0.8582	High Similarity	NPD1529	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1613	Approved
0.8116	Intermediate Similarity	NPD4625	Phase 3
0.8102	Intermediate Similarity	NPD3018	Phase 2
0.8062	Intermediate Similarity	NPD5283	Phase 1
0.8043	Intermediate Similarity	NPD4908	Phase 1
0.7941	Intermediate Similarity	NPD4749	Approved
0.7941	Intermediate Similarity	NPD2983	Phase 2
0.7941	Intermediate Similarity	NPD2982	Phase 2
0.7935	Intermediate Similarity	NPD6234	Discontinued
0.7929	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD1610	Phase 2
0.7907	Intermediate Similarity	NPD228	Approved
0.7868	Intermediate Similarity	NPD2981	Phase 2
0.7843	Intermediate Similarity	NPD37	Approved
0.7817	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD3620	Phase 2
0.781	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD3021	Approved
0.7752	Intermediate Similarity	NPD3022	Approved
0.7727	Intermediate Similarity	NPD1934	Approved
0.7692	Intermediate Similarity	NPD4966	Approved
0.7692	Intermediate Similarity	NPD4060	Phase 1
0.7692	Intermediate Similarity	NPD4967	Phase 2
0.7692	Intermediate Similarity	NPD4965	Approved
0.7681	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2801	Approved
0.7676	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6232	Discontinued
0.7664	Intermediate Similarity	NPD3705	Approved
0.764	Intermediate Similarity	NPD7473	Discontinued
0.763	Intermediate Similarity	NPD1548	Phase 1
0.7593	Intermediate Similarity	NPD7228	Approved
0.7589	Intermediate Similarity	NPD2861	Phase 2
0.7564	Intermediate Similarity	NPD1465	Phase 2
0.7564	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4005	Discontinued
0.7517	Intermediate Similarity	NPD6674	Discontinued
0.75	Intermediate Similarity	NPD3540	Phase 1
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7481	Intermediate Similarity	NPD4750	Phase 3
0.7468	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3882	Suspended
0.7451	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1511	Approved
0.7432	Intermediate Similarity	NPD6100	Approved
0.7432	Intermediate Similarity	NPD6099	Approved
0.7432	Intermediate Similarity	NPD3539	Phase 1
0.7421	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4055	Discovery
0.7417	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7124	Phase 2
0.7362	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6166	Phase 2
0.7362	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1653	Approved
0.7338	Intermediate Similarity	NPD1512	Approved
0.7333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5844	Phase 1
0.7329	Intermediate Similarity	NPD1558	Phase 1
0.7329	Intermediate Similarity	NPD2238	Phase 2
0.731	Intermediate Similarity	NPD5110	Phase 2
0.731	Intermediate Similarity	NPD5109	Approved
0.731	Intermediate Similarity	NPD5111	Phase 2
0.7297	Intermediate Similarity	NPD6111	Discontinued
0.7279	Intermediate Similarity	NPD6671	Approved
0.7254	Intermediate Similarity	NPD6696	Suspended
0.7237	Intermediate Similarity	NPD3892	Phase 2
0.7234	Intermediate Similarity	NPD2232	Approved
0.7234	Intermediate Similarity	NPD2233	Approved
0.7234	Intermediate Similarity	NPD2230	Approved
0.7215	Intermediate Similarity	NPD5089	Approved
0.7215	Intermediate Similarity	NPD5090	Approved
0.7209	Intermediate Similarity	NPD940	Approved
0.7209	Intermediate Similarity	NPD846	Approved
0.7208	Intermediate Similarity	NPD4357	Discontinued
0.7192	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2219	Phase 1
0.7188	Intermediate Similarity	NPD3817	Phase 2
0.7186	Intermediate Similarity	NPD7074	Phase 3
0.7176	Intermediate Similarity	NPD8053	Approved
0.7176	Intermediate Similarity	NPD8054	Approved
0.7174	Intermediate Similarity	NPD5536	Phase 2
0.7171	Intermediate Similarity	NPD5177	Phase 3
0.7169	Intermediate Similarity	NPD3818	Discontinued
0.7163	Intermediate Similarity	NPD422	Phase 1
0.7152	Intermediate Similarity	NPD4678	Approved
0.7152	Intermediate Similarity	NPD4675	Approved
0.7143	Intermediate Similarity	NPD4626	Approved
0.7132	Intermediate Similarity	NPD1242	Phase 1
0.7126	Intermediate Similarity	NPD7054	Approved
0.7124	Intermediate Similarity	NPD3750	Approved
0.7124	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4097	Suspended
0.7101	Intermediate Similarity	NPD7240	Approved
0.7095	Intermediate Similarity	NPD1240	Approved
0.7083	Intermediate Similarity	NPD7472	Approved
0.7078	Intermediate Similarity	NPD2677	Approved
0.7076	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3060	Approved
0.7059	Intermediate Similarity	NPD7549	Discontinued
0.7059	Intermediate Similarity	NPD7635	Approved
0.7054	Intermediate Similarity	NPD3020	Approved
0.7051	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3657	Discovery
0.7047	Intermediate Similarity	NPD230	Phase 1
0.7044	Intermediate Similarity	NPD4380	Phase 2
0.7042	Intermediate Similarity	NPD1091	Approved
0.7039	Intermediate Similarity	NPD7266	Discontinued
0.7039	Intermediate Similarity	NPD5762	Approved
0.7039	Intermediate Similarity	NPD5763	Approved
0.7034	Intermediate Similarity	NPD4624	Approved
0.7029	Intermediate Similarity	NPD7157	Approved
0.7029	Intermediate Similarity	NPD709	Approved
0.7027	Intermediate Similarity	NPD2674	Phase 3
0.702	Intermediate Similarity	NPD1510	Phase 2
0.7015	Intermediate Similarity	NPD2684	Approved
0.7014	Intermediate Similarity	NPD8651	Approved
0.7014	Intermediate Similarity	NPD1283	Approved
0.7012	Intermediate Similarity	NPD5494	Approved
0.7007	Intermediate Similarity	NPD7095	Approved
0.7006	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1607	Approved
0.6987	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.698	Remote Similarity	NPD943	Approved
0.6978	Remote Similarity	NPD7340	Approved
0.6975	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2935	Discontinued
0.697	Remote Similarity	NPD6959	Discontinued
0.6966	Remote Similarity	NPD3094	Phase 2
0.6962	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3144	Approved
0.6959	Remote Similarity	NPD3145	Approved
0.695	Remote Similarity	NPD1651	Approved
0.695	Remote Similarity	NPD1357	Approved
0.6944	Remote Similarity	NPD1669	Approved
0.6943	Remote Similarity	NPD7447	Phase 1
0.6943	Remote Similarity	NPD2532	Approved
0.6943	Remote Similarity	NPD2533	Approved
0.6943	Remote Similarity	NPD2534	Approved
0.6941	Remote Similarity	NPD6797	Phase 2
0.6941	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7843	Approved
0.6933	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5735	Approved
0.6933	Remote Similarity	NPD5124	Phase 1
0.6933	Remote Similarity	NPD6355	Discontinued
0.6928	Remote Similarity	NPD7229	Phase 3
0.6928	Remote Similarity	NPD3787	Discontinued
0.6928	Remote Similarity	NPD1375	Discontinued
0.6919	Remote Similarity	NPD7310	Approved
0.6919	Remote Similarity	NPD7311	Approved
0.6919	Remote Similarity	NPD7312	Approved
0.6919	Remote Similarity	NPD4578	Approved
0.6919	Remote Similarity	NPD7313	Approved
0.6919	Remote Similarity	NPD4577	Approved
0.6914	Remote Similarity	NPD7819	Suspended
0.6914	Remote Similarity	NPD4585	Approved
0.6908	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7251	Discontinued
0.6901	Remote Similarity	NPD2667	Approved
0.6901	Remote Similarity	NPD2668	Approved
0.6897	Remote Similarity	NPD2922	Phase 1
0.6897	Remote Similarity	NPD4663	Approved
0.6884	Remote Similarity	NPD1398	Phase 1
0.6879	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7309	Approved
0.6879	Remote Similarity	NPD7213	Phase 3
0.6879	Remote Similarity	NPD7041	Phase 2
0.6879	Remote Similarity	NPD7212	Phase 2
0.6875	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2560	Approved
0.6871	Remote Similarity	NPD2563	Approved
0.686	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7808	Phase 3
0.6859	Remote Similarity	NPD6190	Approved
0.6859	Remote Similarity	NPD5241	Discontinued
0.6857	Remote Similarity	NPD7906	Approved
0.6845	Remote Similarity	NPD27	Approved
0.6845	Remote Similarity	NPD2489	Approved
0.6842	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4536	Approved
0.6842	Remote Similarity	NPD4538	Approved
0.6842	Remote Similarity	NPD6895	Approved
0.6842	Remote Similarity	NPD6896	Approved
0.6839	Remote Similarity	NPD4236	Phase 3
0.6839	Remote Similarity	NPD4237	Approved
0.6839	Remote Similarity	NPD1652	Phase 2
0.6835	Remote Similarity	NPD4123	Phase 3

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