NPASS Compound

Structure

CID210478 OpenBabel06191716002D 26 27 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 9 1 0 0 0 0 5 18 2 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 11 2 0 0 0 0 8 19 1 0 0 0 0 10 16 2 0 0 0 0 10 23 1 0 0 0 0 11 16 1 0 0 0 0 11 24 1 0 0 0 0 12 8 1 6 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 1 0 0 0 14 15 1 0 0 0 0 14 21 1 6 0 0 0 15 17 1 0 0 0 0 15 22 1 1 0 0 0 16 26 1 0 0 0 0 17 25 1 0 0 0 0 17 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.13
Volume:	351.405
LogP:	-0.319
LogD:	-0.424
LogS:	-1.902
# Rotatable Bonds:	7
TPSA:	134.91
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.355
Synthetic Accessibility Score:	3.776
Fsp3:	0.471
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.395
MDCK Permeability:	4.6684814151376486e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.542
Human Intestinal Absorption (HIA):	0.722
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.812

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.613
Plasma Protein Binding (PPB):	39.697574615478516%
Volume Distribution (VD):	0.467
Pgp-substrate:	28.13548469543457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.433
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.578
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.496
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.401
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	2.627
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.216
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.34
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.604
Carcinogencity:	0.31
Eye Corrosion:	0.004
Eye Irritation:	0.037
Respiratory Toxicity:	0.195

Download Data

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

Natural Product: NPC210478

Natural Product ID:	NPC210478
*Common Name:**	Sinapaldehyde Glucoside
IUPAC Name:	(E)-3-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enal
Synonyms:	Sinapaldehyde Glucoside
Standard InCHIKey:	OYTCTPHTVUEGCL-GCPOEHJPSA-N
Standard InCHI:	InChI=1S/C17H22O9/c1-23-10-6-9(4-3-5-18)7-11(24-2)16(10)26-17-15(22)14(21)13(20)12(8-19)25-17/h3-7,12-15,17,19-22H,8H2,1-2H3/b4-3+/t12-,13-,14+,15-,17+/m1/s1
SMILES:	COc1cc(/C=C/C=O)cc(c1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251059
PubChem CID:	25791064
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21955940]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO14548	Ilex rotunda	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14548	Ilex rotunda	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14548	Ilex rotunda	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14548	Ilex rotunda	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	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	2
IC50	3

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[453603]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[453603]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[453603]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	100000.0	nM	PMID[453604]
NPT1	Others	Radical scavenging activity		EC50	>	100000.0	nM	PMID[453604]

☑ 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 NPC210478 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	319
0.1-0.2	1581
0.2-0.3	4661
0.3-0.4	10766
0.4-0.5	7447
0.5-0.6	5022
0.6-0.7	7483
0.7-0.8	4831
0.8-0.85	439
0.85-0.9	121
0.9-0.95	24
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC55040
0.947	High Similarity	NPC162093
0.9398	High Similarity	NPC49074
0.9333	High Similarity	NPC37468
0.9259	High Similarity	NPC470236
0.9254	High Similarity	NPC69513
0.9254	High Similarity	NPC215833
0.9197	High Similarity	NPC100389
0.9191	High Similarity	NPC164857
0.9185	High Similarity	NPC13745
0.9185	High Similarity	NPC251981
0.9185	High Similarity	NPC48863
0.9179	High Similarity	NPC299144
0.9167	High Similarity	NPC302378
0.9155	High Similarity	NPC93924
0.9155	High Similarity	NPC96294
0.9155	High Similarity	NPC478237
0.9143	High Similarity	NPC297342
0.9118	High Similarity	NPC185778
0.9111	High Similarity	NPC132895
0.9098	High Similarity	NPC248355
0.9091	High Similarity	NPC106138
0.9085	High Similarity	NPC52740
0.9058	High Similarity	NPC212770
0.9058	High Similarity	NPC98777
0.9051	High Similarity	NPC186418
0.9051	High Similarity	NPC157554
0.903	High Similarity	NPC472024
0.903	High Similarity	NPC80600
0.9028	High Similarity	NPC114740
0.9	High Similarity	NPC157816
0.9	High Similarity	NPC278469
0.9	High Similarity	NPC193722
0.8993	High Similarity	NPC267291
0.8993	High Similarity	NPC202700
0.8986	High Similarity	NPC59324
0.8986	High Similarity	NPC65530
0.8966	High Similarity	NPC213197
0.8955	High Similarity	NPC166040
0.8955	High Similarity	NPC26653
0.8955	High Similarity	NPC270849
0.8951	High Similarity	NPC41844
0.8936	High Similarity	NPC478239
0.8929	High Similarity	NPC83375
0.8929	High Similarity	NPC224876
0.8921	High Similarity	NPC226005
0.8913	High Similarity	NPC242028
0.8913	High Similarity	NPC104167
0.8913	High Similarity	NPC203230
0.8905	High Similarity	NPC107478
0.8904	High Similarity	NPC215060
0.8904	High Similarity	NPC476352
0.8897	High Similarity	NPC470270
0.8881	High Similarity	NPC199928
0.8865	High Similarity	NPC475084
0.8865	High Similarity	NPC469559
0.8865	High Similarity	NPC189115
0.8849	High Similarity	NPC195196
0.8849	High Similarity	NPC124149
0.8832	High Similarity	NPC115022
0.8832	High Similarity	NPC294166
0.8832	High Similarity	NPC25821
0.8828	High Similarity	NPC90896
0.8828	High Similarity	NPC212670
0.8828	High Similarity	NPC283839
0.8828	High Similarity	NPC206264
0.8828	High Similarity	NPC313334
0.8824	High Similarity	NPC9912
0.8824	High Similarity	NPC469698
0.8824	High Similarity	NPC473412
0.8815	High Similarity	NPC307110
0.8794	High Similarity	NPC469661
0.8794	High Similarity	NPC186406
0.8788	High Similarity	NPC108545
0.8777	High Similarity	NPC25695
0.8777	High Similarity	NPC172818
0.8776	High Similarity	NPC470264
0.8768	High Similarity	NPC187194
0.8767	High Similarity	NPC227980
0.8759	High Similarity	NPC165686
0.8759	High Similarity	NPC85799
0.8759	High Similarity	NPC26080
0.8759	High Similarity	NPC303422
0.875	High Similarity	NPC476865
0.8741	High Similarity	NPC232228
0.8741	High Similarity	NPC473045
0.8741	High Similarity	NPC25292
0.8741	High Similarity	NPC292443
0.8732	High Similarity	NPC140502
0.8716	High Similarity	NPC150442
0.8716	High Similarity	NPC246893
0.8705	High Similarity	NPC238243
0.8696	High Similarity	NPC36490
0.8686	High Similarity	NPC248307
0.8686	High Similarity	NPC65942
0.8686	High Similarity	NPC121376
0.8681	High Similarity	NPC476864
0.8681	High Similarity	NPC476869
0.8681	High Similarity	NPC476866
0.8681	High Similarity	NPC476868
0.8681	High Similarity	NPC475096
0.8681	High Similarity	NPC476450
0.8676	High Similarity	NPC295970
0.8671	High Similarity	NPC252169
0.8671	High Similarity	NPC473044
0.8667	High Similarity	NPC284810
0.8662	High Similarity	NPC300611
0.8657	High Similarity	NPC12308
0.8657	High Similarity	NPC27352
0.8649	High Similarity	NPC176186
0.8649	High Similarity	NPC169404
0.8649	High Similarity	NPC289967
0.8649	High Similarity	NPC53587
0.8649	High Similarity	NPC472612
0.8649	High Similarity	NPC472611
0.8643	High Similarity	NPC138350
0.8643	High Similarity	NPC471719
0.8643	High Similarity	NPC103409
0.8643	High Similarity	NPC3293
0.8643	High Similarity	NPC40664
0.8643	High Similarity	NPC197723
0.8643	High Similarity	NPC165482
0.8633	High Similarity	NPC237594
0.8633	High Similarity	NPC249791
0.8633	High Similarity	NPC476387
0.8633	High Similarity	NPC119060
0.8633	High Similarity	NPC476411
0.8633	High Similarity	NPC188555
0.8633	High Similarity	NPC130496
0.8623	High Similarity	NPC5423
0.8623	High Similarity	NPC252833
0.8621	High Similarity	NPC99515
0.8621	High Similarity	NPC125755
0.8621	High Similarity	NPC190714
0.8611	High Similarity	NPC476867
0.8611	High Similarity	NPC110063
0.8591	High Similarity	NPC310661
0.8591	High Similarity	NPC105827
0.8582	High Similarity	NPC470413
0.8582	High Similarity	NPC138738
0.8571	High Similarity	NPC214729
0.8571	High Similarity	NPC111785
0.8562	High Similarity	NPC39657
0.8562	High Similarity	NPC15577
0.8562	High Similarity	NPC227902
0.8561	High Similarity	NPC6836
0.8553	High Similarity	NPC289811
0.8553	High Similarity	NPC160780
0.8552	High Similarity	NPC277867
0.8552	High Similarity	NPC34927
0.8552	High Similarity	NPC34587
0.8552	High Similarity	NPC476382
0.8552	High Similarity	NPC85624
0.8552	High Similarity	NPC252292
0.8552	High Similarity	NPC216819
0.8552	High Similarity	NPC83743
0.8552	High Similarity	NPC287615
0.8552	High Similarity	NPC100998
0.8552	High Similarity	NPC161700
0.8552	High Similarity	NPC262182
0.8551	High Similarity	NPC166168
0.8551	High Similarity	NPC30043
0.8551	High Similarity	NPC469613
0.8551	High Similarity	NPC469625
0.8542	High Similarity	NPC138212
0.854	High Similarity	NPC470258
0.854	High Similarity	NPC273295
0.854	High Similarity	NPC202582
0.854	High Similarity	NPC285339
0.854	High Similarity	NPC48315
0.854	High Similarity	NPC477294
0.854	High Similarity	NPC3439
0.854	High Similarity	NPC222004
0.854	High Similarity	NPC229784
0.854	High Similarity	NPC226788
0.854	High Similarity	NPC190629
0.854	High Similarity	NPC218856
0.854	High Similarity	NPC218003
0.854	High Similarity	NPC477293
0.854	High Similarity	NPC210623
0.8531	High Similarity	NPC476442
0.8531	High Similarity	NPC215512
0.8529	High Similarity	NPC474119
0.8523	High Similarity	NPC302610
0.8523	High Similarity	NPC289438
0.8521	High Similarity	NPC43500
0.8521	High Similarity	NPC164148
0.8519	High Similarity	NPC271985
0.8503	High Similarity	NPC175976
0.8503	High Similarity	NPC270751
0.8503	High Similarity	NPC476348
0.8503	High Similarity	NPC187398
0.85	High Similarity	NPC87696
0.85	High Similarity	NPC111635
0.85	High Similarity	NPC309744
0.85	High Similarity	NPC470881
0.85	High Similarity	NPC35731
0.85	High Similarity	NPC170694
0.8497	Intermediate Similarity	NPC203020
0.8497	Intermediate Similarity	NPC239966

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 NPC210478 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	891
0.2-0.3	1983
0.3-0.4	2892
0.4-0.5	1671
0.5-0.6	924
0.6-0.7	453
0.7-0.8	63
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8828	High Similarity	NPD1653	Approved
0.8143	Intermediate Similarity	NPD3027	Phase 3
0.8138	Intermediate Similarity	NPD7266	Discontinued
0.8088	Intermediate Similarity	NPD1091	Approved
0.8012	Intermediate Similarity	NPD7054	Approved
0.7972	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1613	Approved
0.7963	Intermediate Similarity	NPD7472	Approved
0.7963	Intermediate Similarity	NPD7074	Phase 3
0.795	Intermediate Similarity	NPD3818	Discontinued
0.7818	Intermediate Similarity	NPD7808	Phase 3
0.7805	Intermediate Similarity	NPD6797	Phase 2
0.7785	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6559	Discontinued
0.7758	Intermediate Similarity	NPD7251	Discontinued
0.7737	Intermediate Similarity	NPD1357	Approved
0.7714	Intermediate Similarity	NPD2982	Phase 2
0.7714	Intermediate Similarity	NPD2983	Phase 2
0.7711	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD3705	Approved
0.7692	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6674	Discontinued
0.7667	Intermediate Similarity	NPD1652	Phase 2
0.7643	Intermediate Similarity	NPD37	Approved
0.7643	Intermediate Similarity	NPD2981	Phase 2
0.7643	Intermediate Similarity	NPD1934	Approved
0.764	Intermediate Similarity	NPD7199	Phase 2
0.7622	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD4965	Approved
0.761	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD4967	Phase 2
0.761	Intermediate Similarity	NPD4966	Approved
0.7589	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6841	Approved
0.7588	Intermediate Similarity	NPD6843	Phase 3
0.7588	Intermediate Similarity	NPD6842	Approved
0.7548	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD3817	Phase 2
0.7516	Intermediate Similarity	NPD6234	Discontinued
0.7515	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3018	Phase 2
0.7484	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD5536	Phase 2
0.7439	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3882	Suspended
0.7375	Intermediate Similarity	NPD2801	Approved
0.7365	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5844	Phase 1
0.7355	Intermediate Similarity	NPD4357	Discontinued
0.7355	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7685	Pre-registration
0.7337	Intermediate Similarity	NPD7240	Approved
0.7324	Intermediate Similarity	NPD422	Phase 1
0.7315	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5124	Phase 1
0.7315	Intermediate Similarity	NPD230	Phase 1
0.726	Intermediate Similarity	NPD9494	Approved
0.7239	Intermediate Similarity	NPD1358	Approved
0.723	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7843	Approved
0.7226	Intermediate Similarity	NPD6190	Approved
0.7211	Intermediate Similarity	NPD4908	Phase 1
0.7194	Intermediate Similarity	NPD7157	Approved
0.7188	Intermediate Similarity	NPD4380	Phase 2
0.7185	Intermediate Similarity	NPD2684	Approved
0.7179	Intermediate Similarity	NPD5058	Phase 3
0.7176	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4628	Phase 3
0.716	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD8455	Phase 2
0.7153	Intermediate Similarity	NPD228	Approved
0.7152	Intermediate Similarity	NPD5494	Approved
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7134	Intermediate Similarity	NPD5297	Approved
0.7134	Intermediate Similarity	NPD1511	Approved
0.7134	Intermediate Similarity	NPD7075	Discontinued
0.7134	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6799	Approved
0.7121	Intermediate Similarity	NPD291	Approved
0.7117	Intermediate Similarity	NPD5402	Approved
0.7117	Intermediate Similarity	NPD5353	Approved
0.7114	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD290	Approved
0.7101	Intermediate Similarity	NPD3751	Discontinued
0.7086	Intermediate Similarity	NPD1933	Approved
0.7086	Intermediate Similarity	NPD447	Suspended
0.7083	Intermediate Similarity	NPD1610	Phase 2
0.7081	Intermediate Similarity	NPD4675	Approved
0.7081	Intermediate Similarity	NPD4678	Approved
0.7078	Intermediate Similarity	NPD1375	Discontinued
0.7066	Intermediate Similarity	NPD3787	Discontinued
0.7063	Intermediate Similarity	NPD3686	Approved
0.7063	Intermediate Similarity	NPD3687	Approved
0.7055	Intermediate Similarity	NPD7819	Suspended
0.7055	Intermediate Similarity	NPD1465	Phase 2
0.705	Intermediate Similarity	NPD5283	Phase 1
0.7044	Intermediate Similarity	NPD1512	Approved
0.7042	Intermediate Similarity	NPD1548	Phase 1
0.7039	Intermediate Similarity	NPD2492	Phase 1
0.7037	Intermediate Similarity	NPD3134	Approved
0.7014	Intermediate Similarity	NPD3496	Discontinued
0.7013	Intermediate Similarity	NPD1551	Phase 2
0.7012	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD556	Approved
0.7006	Intermediate Similarity	NPD8127	Discontinued
0.7006	Intermediate Similarity	NPD2219	Phase 1
0.7	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6801	Discontinued
0.6994	Remote Similarity	NPD7549	Discontinued
0.6993	Remote Similarity	NPD4536	Approved
0.6993	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4538	Approved
0.6993	Remote Similarity	NPD7097	Phase 1
0.6988	Remote Similarity	NPD919	Approved
0.6987	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4749	Approved
0.6981	Remote Similarity	NPD5401	Approved
0.6971	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3540	Phase 1
0.6954	Remote Similarity	NPD6233	Phase 2
0.6943	Remote Similarity	NPD4110	Phase 3
0.6943	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6653	Approved
0.6923	Remote Similarity	NPD1549	Phase 2
0.6914	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2861	Phase 2
0.6908	Remote Similarity	NPD4060	Phase 1
0.6905	Remote Similarity	NPD1247	Approved
0.6903	Remote Similarity	NPD2796	Approved
0.6903	Remote Similarity	NPD3539	Phase 1
0.6899	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4237	Approved
0.6879	Remote Similarity	NPD4236	Phase 3
0.6871	Remote Similarity	NPD6599	Discontinued
0.6864	Remote Similarity	NPD6232	Discontinued
0.6863	Remote Similarity	NPD4340	Discontinued
0.6859	Remote Similarity	NPD5762	Approved
0.6859	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5763	Approved
0.6848	Remote Similarity	NPD2978	Approved
0.6848	Remote Similarity	NPD2977	Approved
0.6842	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5588	Approved
0.6839	Remote Similarity	NPD5960	Phase 3
0.6829	Remote Similarity	NPD7411	Suspended
0.6828	Remote Similarity	NPD1778	Approved
0.6824	Remote Similarity	NPD8651	Approved
0.6821	Remote Similarity	NPD4625	Phase 3
0.6821	Remote Similarity	NPD7095	Approved
0.6813	Remote Similarity	NPD1774	Approved
0.6797	Remote Similarity	NPD1558	Phase 1
0.6792	Remote Similarity	NPD2677	Approved
0.6776	Remote Similarity	NPD6798	Discontinued
0.6772	Remote Similarity	NPD4162	Approved
0.677	Remote Similarity	NPD4123	Phase 3
0.677	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD8313	Approved
0.6761	Remote Similarity	NPD8312	Approved
0.6757	Remote Similarity	NPD3685	Discontinued
0.6755	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6355	Discontinued
0.6747	Remote Similarity	NPD5772	Approved
0.6747	Remote Similarity	NPD5773	Approved
0.6746	Remote Similarity	NPD5677	Discontinued
0.6744	Remote Similarity	NPD7473	Discontinued
0.6739	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4062	Phase 3
0.673	Remote Similarity	NPD3750	Approved
0.6727	Remote Similarity	NPD5089	Approved
0.6727	Remote Similarity	NPD5090	Approved
0.6725	Remote Similarity	NPD3926	Phase 2
0.6725	Remote Similarity	NPD5242	Approved
0.6713	Remote Similarity	NPD6671	Approved
0.6711	Remote Similarity	NPD3179	Approved
0.6711	Remote Similarity	NPD3180	Approved
0.6709	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4005	Discontinued
0.6707	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1241	Discontinued
0.6688	Remote Similarity	NPD3454	Phase 3
0.6688	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4140	Approved
0.6688	Remote Similarity	NPD3620	Phase 2
0.6685	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7680	Approved
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD3060	Approved
0.6667	Remote Similarity	NPD1049	Clinical (unspecified phase)

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