NPASS Compound

Structure

NPC470413 OpenBabel07101719512D 38 40 0 0 1 0 0 0 0 0999 V2000 -12.9904 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 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 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 0.0000 C 0 0 3 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 -9.5263 1.5000 0.0000 C 0 0 3 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 0.0000 -2.0000 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 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 -12.9904 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 2.5000 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 0.0000 -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 -12.9904 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 1 34 1 0 0 0 0 2 35 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 14 1 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 36 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 29 1 0 0 0 0 17 19 2 0 0 0 0 17 37 1 0 0 0 0 18 34 1 0 0 0 0 19 35 1 0 0 0 0 20 22 1 0 0 0 0 20 37 1 0 0 0 0 21 13 1 6 0 0 0 21 23 1 0 0 0 0 21 38 1 0 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 23 31 1 1 0 0 0 24 25 1 0 0 0 0 24 32 1 6 0 0 0 25 26 1 0 0 0 0 25 33 1 1 0 0 0 26 36 1 6 0 0 0 26 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.21
Volume:	519.61
LogP:	-0.394
LogD:	0.342
LogS:	-2.171
# Rotatable Bonds:	12
TPSA:	187.76
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.187
Synthetic Accessibility Score:	4.26
Fsp3:	0.462
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.952
MDCK Permeability:	2.0136772945988923e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.943
Human Intestinal Absorption (HIA):	0.879
20% Bioavailability (F20%):	0.181
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.314
Plasma Protein Binding (PPB):	65.68988800048828%
Volume Distribution (VD):	0.361
Pgp-substrate:	19.675395965576172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.638
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.621
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.126

ADMET: Excretion

Clearance (CL):	2.656
Half-life (T1/2):	0.842

ADMET: Toxicity

hERG Blockers:	0.288
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.228
AMES Toxicity:	0.211
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.16
Carcinogencity:	0.253
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.006

Download Data

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

Natural Product: NPC470413

Natural Product ID:	NPC470413
*Common Name:**	2-((E)-3-{4-[2-Hydroxy-2-(4-Hydroxy-3-Methoxy-Phenyl)-1-Hydroxymethyl-Ethoxy]-3-Methoxy-Phenyl}-Allyloxy)-6-Hydroxymethyl-Tetrahydro-Pyran-3,4,5-Triol
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[(E)-3-[4-[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxyphenyl]prop-2-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	KMRNHQMTDWXUBS-DTFCWUHSSA-N
Standard InCHI:	InChI=1S/C26H34O12/c1-34-18-11-15(6-7-16(18)29)22(30)20(12-27)37-17-8-5-14(10-19(17)35-2)4-3-9-36-26-25(33)24(32)23(31)21(13-28)38-26/h3-8,10-11,20-33H,9,12-13H2,1-2H3/b4-3+/t20?,21-,22?,23-,24+,25-,26-/m1/s1
SMILES:	COC1=C(C=CC(=C1)C=CCOC2C(C(C(C(O2)CO)O)O)O)OC(CO)C(C3=CC(=C(C=C3)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2029018
PubChem CID:	11478224
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	roots	Miyazaki prefecture, Japan	n.a.	PMID[9873511]
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3509	Angelica furcijuga	Species	Apiaceae	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
IC50	2
Others	2

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	>	100000.0	nM	PMID[547025]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	-0.2	%	PMID[547025]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	100000.0	nM	PMID[547025]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	-26.0	%	PMID[547025]

☑ 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 NPC470413 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	381
0.1-0.2	1488
0.2-0.3	4159
0.3-0.4	10607
0.4-0.5	7834
0.5-0.6	5008
0.6-0.7	7661
0.7-0.8	4118
0.8-0.85	912
0.85-0.9	366
0.9-0.95	144
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC138738
0.9771	High Similarity	NPC177035
0.9771	High Similarity	NPC52277
0.9771	High Similarity	NPC199459
0.9769	High Similarity	NPC187194
0.9701	High Similarity	NPC469559
0.9699	High Similarity	NPC106944
0.963	High Similarity	NPC46092
0.963	High Similarity	NPC185307
0.963	High Similarity	NPC470950
0.9618	High Similarity	NPC35731
0.9618	High Similarity	NPC476411
0.9559	High Similarity	NPC129417
0.9559	High Similarity	NPC283995
0.9559	High Similarity	NPC470235
0.9556	High Similarity	NPC476356
0.9556	High Similarity	NPC189115
0.9538	High Similarity	NPC65942
0.9538	High Similarity	NPC248307
0.9489	High Similarity	NPC279298
0.9489	High Similarity	NPC22150
0.9489	High Similarity	NPC18979
0.9489	High Similarity	NPC475096
0.9489	High Similarity	NPC38041
0.9481	High Similarity	NPC472711
0.9481	High Similarity	NPC469661
0.9478	High Similarity	NPC98777
0.9478	High Similarity	NPC212770
0.9462	High Similarity	NPC80600
0.9462	High Similarity	NPC472024
0.942	High Similarity	NPC112861
0.9416	High Similarity	NPC473045
0.9416	High Similarity	NPC25292
0.9412	High Similarity	NPC475084
0.9403	High Similarity	NPC59324
0.9403	High Similarity	NPC304152
0.9403	High Similarity	NPC65530
0.9389	High Similarity	NPC9912
0.9385	High Similarity	NPC307110
0.9385	High Similarity	NPC248355
0.9385	High Similarity	NPC5851
0.9385	High Similarity	NPC166040
0.9385	High Similarity	NPC270849
0.9385	High Similarity	NPC86030
0.9385	High Similarity	NPC26653
0.9353	High Similarity	NPC224674
0.9353	High Similarity	NPC114505
0.9353	High Similarity	NPC227902
0.9353	High Similarity	NPC193473
0.9353	High Similarity	NPC275284
0.9353	High Similarity	NPC39657
0.9353	High Similarity	NPC31325
0.9353	High Similarity	NPC15956
0.9353	High Similarity	NPC213074
0.9343	High Similarity	NPC113680
0.9343	High Similarity	NPC477898
0.9343	High Similarity	NPC278961
0.9343	High Similarity	NPC473044
0.9343	High Similarity	NPC478239
0.9328	High Similarity	NPC242028
0.9328	High Similarity	NPC203230
0.9323	High Similarity	NPC470881
0.9308	High Similarity	NPC302378
0.9308	High Similarity	NPC72529
0.9281	High Similarity	NPC190714
0.9281	High Similarity	NPC99515
0.9281	High Similarity	NPC125755
0.9275	High Similarity	NPC84181
0.927	High Similarity	NPC246947
0.927	High Similarity	NPC48309
0.927	High Similarity	NPC140502
0.927	High Similarity	NPC60249
0.927	High Similarity	NPC5262
0.927	High Similarity	NPC157816
0.927	High Similarity	NPC472714
0.9248	High Similarity	NPC25821
0.9248	High Similarity	NPC6836
0.9231	High Similarity	NPC292056
0.9231	High Similarity	NPC118787
0.9231	High Similarity	NPC319625
0.9231	High Similarity	NPC163332
0.9231	High Similarity	NPC147821
0.9231	High Similarity	NPC41706
0.9231	High Similarity	NPC111247
0.9231	High Similarity	NPC183181
0.922	High Similarity	NPC286235
0.922	High Similarity	NPC106138
0.922	High Similarity	NPC44452
0.922	High Similarity	NPC51328
0.922	High Similarity	NPC55158
0.9209	High Similarity	NPC286245
0.9209	High Similarity	NPC34587
0.9209	High Similarity	NPC277867
0.9209	High Similarity	NPC43508
0.9209	High Similarity	NPC476382
0.9209	High Similarity	NPC100998
0.9209	High Similarity	NPC272619
0.9209	High Similarity	NPC161700
0.9209	High Similarity	NPC469586
0.9209	High Similarity	NPC252292
0.9209	High Similarity	NPC34927
0.9209	High Similarity	NPC476301
0.9203	High Similarity	NPC252169
0.9197	High Similarity	NPC186406
0.9197	High Similarity	NPC76871
0.9185	High Similarity	NPC164857
0.9179	High Similarity	NPC13745
0.9179	High Similarity	NPC251981
0.9179	High Similarity	NPC48863
0.9179	High Similarity	NPC87696
0.9179	High Similarity	NPC107478
0.9179	High Similarity	NPC170694
0.9173	High Similarity	NPC252833
0.9173	High Similarity	NPC254275
0.916	High Similarity	NPC245826
0.916	High Similarity	NPC252307
0.916	High Similarity	NPC474178
0.9155	High Similarity	NPC98624
0.9155	High Similarity	NPC475224
0.9154	High Similarity	NPC58607
0.9154	High Similarity	NPC178284
0.9154	High Similarity	NPC191037
0.9149	High Similarity	NPC175976
0.9149	High Similarity	NPC130449
0.9149	High Similarity	NPC116229
0.9149	High Similarity	NPC248132
0.9143	High Similarity	NPC199928
0.9143	High Similarity	NPC476865
0.9137	High Similarity	NPC472713
0.9137	High Similarity	NPC217635
0.9137	High Similarity	NPC253015
0.9137	High Similarity	NPC473046
0.9137	High Similarity	NPC232228
0.9137	High Similarity	NPC472712
0.9137	High Similarity	NPC168579
0.9137	High Similarity	NPC471065
0.9137	High Similarity	NPC79429
0.9137	High Similarity	NPC76176
0.9137	High Similarity	NPC187774
0.9137	High Similarity	NPC469313
0.9137	High Similarity	NPC471667
0.9137	High Similarity	NPC138227
0.9137	High Similarity	NPC471063
0.9137	High Similarity	NPC118385
0.913	High Similarity	NPC477794
0.913	High Similarity	NPC477799
0.913	High Similarity	NPC477800
0.9118	High Similarity	NPC477798
0.9118	High Similarity	NPC477797
0.9111	High Similarity	NPC101624
0.9111	High Similarity	NPC184938
0.9111	High Similarity	NPC470236
0.9104	High Similarity	NPC132895
0.9104	High Similarity	NPC115022
0.9104	High Similarity	NPC69513
0.9104	High Similarity	NPC294166
0.9104	High Similarity	NPC215833
0.9104	High Similarity	NPC49074
0.9098	High Similarity	NPC166168
0.9084	High Similarity	NPC79715
0.9084	High Similarity	NPC108659
0.9084	High Similarity	NPC264900
0.9084	High Similarity	NPC231607
0.9078	High Similarity	NPC473480
0.9078	High Similarity	NPC15538
0.9078	High Similarity	NPC232992
0.9077	High Similarity	NPC194519
0.9071	High Similarity	NPC476866
0.9071	High Similarity	NPC476869
0.9071	High Similarity	NPC476864
0.9071	High Similarity	NPC476868
0.9065	High Similarity	NPC37793
0.9051	High Similarity	NPC100389
0.9051	High Similarity	NPC156376
0.9044	High Similarity	NPC138350
0.9044	High Similarity	NPC165482
0.9044	High Similarity	NPC172818
0.9044	High Similarity	NPC3293
0.9044	High Similarity	NPC197723
0.9044	High Similarity	NPC25695
0.9044	High Similarity	NPC40664
0.903	High Similarity	NPC85799
0.903	High Similarity	NPC184447
0.903	High Similarity	NPC160991
0.903	High Similarity	NPC165686
0.903	High Similarity	NPC35932
0.903	High Similarity	NPC303422
0.903	High Similarity	NPC26080
0.903	High Similarity	NPC162093
0.903	High Similarity	NPC470270
0.903	High Similarity	NPC16208
0.903	High Similarity	NPC7903
0.903	High Similarity	NPC299144
0.9021	High Similarity	NPC472710
0.9021	High Similarity	NPC472709
0.9014	High Similarity	NPC280945
0.9008	High Similarity	NPC94179
0.9007	High Similarity	NPC276753
0.9007	High Similarity	NPC205796
0.9	High Similarity	NPC110063

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 NPC470413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	843
0.2-0.3	1808
0.3-0.4	2783
0.4-0.5	1699
0.5-0.6	958
0.6-0.7	621
0.7-0.8	120
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
0.8777	High Similarity	NPD7266	Discontinued
0.8667	High Similarity	NPD3027	Phase 3
0.8613	High Similarity	NPD1612	Clinical (unspecified phase)
0.8613	High Similarity	NPD1613	Approved
0.8435	Intermediate Similarity	NPD1653	Approved
0.8392	Intermediate Similarity	NPD6674	Discontinued
0.8346	Intermediate Similarity	NPD1091	Approved
0.8321	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD7054	Approved
0.8176	Intermediate Similarity	NPD7074	Phase 3
0.8176	Intermediate Similarity	NPD7472	Approved
0.8074	Intermediate Similarity	NPD3705	Approved
0.7985	Intermediate Similarity	NPD1357	Approved
0.7963	Intermediate Similarity	NPD7251	Discontinued
0.7937	Intermediate Similarity	NPD7228	Approved
0.7937	Intermediate Similarity	NPD3818	Discontinued
0.7923	Intermediate Similarity	NPD228	Approved
0.7914	Intermediate Similarity	NPD7808	Phase 3
0.7901	Intermediate Similarity	NPD6797	Phase 2
0.7857	Intermediate Similarity	NPD2861	Phase 2
0.7852	Intermediate Similarity	NPD5058	Phase 3
0.7834	Intermediate Similarity	NPD6234	Discontinued
0.7805	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7685	Pre-registration
0.7742	Intermediate Similarity	NPD37	Approved
0.7742	Intermediate Similarity	NPD1934	Approved
0.7727	Intermediate Similarity	NPD7843	Approved
0.7708	Intermediate Similarity	NPD1558	Phase 1
0.7707	Intermediate Similarity	NPD4966	Approved
0.7707	Intermediate Similarity	NPD4967	Phase 2
0.7707	Intermediate Similarity	NPD4965	Approved
0.7698	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2977	Approved
0.7692	Intermediate Similarity	NPD2978	Approved
0.7692	Intermediate Similarity	NPD8455	Phase 2
0.7687	Intermediate Similarity	NPD7157	Approved
0.7682	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD4908	Phase 1
0.7671	Intermediate Similarity	NPD4538	Approved
0.7671	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4536	Approved
0.7669	Intermediate Similarity	NPD5283	Phase 1
0.7658	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7199	Phase 2
0.7595	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6166	Phase 2
0.7593	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3620	Phase 2
0.7586	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD2982	Phase 2
0.7571	Intermediate Similarity	NPD2983	Phase 2
0.7569	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD2684	Approved
0.7554	Intermediate Similarity	NPD1610	Phase 2
0.7518	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD2981	Phase 2
0.75	Intermediate Similarity	NPD5588	Approved
0.75	Intermediate Similarity	NPD5960	Phase 3
0.7483	Intermediate Similarity	NPD3018	Phase 2
0.7468	Intermediate Similarity	NPD2801	Approved
0.7466	Intermediate Similarity	NPD4060	Phase 1
0.7455	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6190	Approved
0.7432	Intermediate Similarity	NPD7097	Phase 1
0.7426	Intermediate Similarity	NPD6671	Approved
0.7425	Intermediate Similarity	NPD6559	Discontinued
0.7425	Intermediate Similarity	NPD7240	Approved
0.7423	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3060	Approved
0.74	Intermediate Similarity	NPD1375	Discontinued
0.7397	Intermediate Similarity	NPD6233	Phase 2
0.7394	Intermediate Similarity	NPD8651	Approved
0.7379	Intermediate Similarity	NPD7095	Approved
0.7368	Intermediate Similarity	NPD3022	Approved
0.7368	Intermediate Similarity	NPD3021	Approved
0.7353	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD290	Approved
0.7329	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3817	Phase 2
0.731	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4237	Approved
0.7303	Intermediate Similarity	NPD4236	Phase 3
0.7303	Intermediate Similarity	NPD4162	Approved
0.7297	Intermediate Similarity	NPD5735	Approved
0.7292	Intermediate Similarity	NPD6584	Phase 3
0.729	Intermediate Similarity	NPD4123	Phase 3
0.7286	Intermediate Similarity	NPD5125	Phase 3
0.7286	Intermediate Similarity	NPD5126	Approved
0.7286	Intermediate Similarity	NPD5846	Approved
0.7286	Intermediate Similarity	NPD6516	Phase 2
0.7285	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD968	Approved
0.7267	Intermediate Similarity	NPD4108	Discontinued
0.7267	Intermediate Similarity	NPD3882	Suspended
0.7261	Intermediate Similarity	NPD3687	Approved
0.7261	Intermediate Similarity	NPD3686	Approved
0.726	Intermediate Similarity	NPD4625	Phase 3
0.7255	Intermediate Similarity	NPD4628	Phase 3
0.725	Intermediate Similarity	NPD5773	Approved
0.725	Intermediate Similarity	NPD5772	Approved
0.7248	Intermediate Similarity	NPD6653	Approved
0.7231	Intermediate Similarity	NPD291	Approved
0.7226	Intermediate Similarity	NPD1511	Approved
0.7211	Intermediate Similarity	NPD6798	Discontinued
0.7211	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2677	Approved
0.7205	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4749	Approved
0.7197	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5536	Phase 2
0.719	Intermediate Similarity	NPD5177	Phase 3
0.719	Intermediate Similarity	NPD1652	Phase 2
0.7188	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6355	Discontinued
0.7181	Intermediate Similarity	NPD4340	Discontinued
0.7171	Intermediate Similarity	NPD5762	Approved
0.7171	Intermediate Similarity	NPD5763	Approved
0.717	Intermediate Similarity	NPD4678	Approved
0.717	Intermediate Similarity	NPD4675	Approved
0.7162	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6331	Phase 2
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD4535	Phase 3
0.7135	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD8313	Approved
0.7134	Intermediate Similarity	NPD1512	Approved
0.7133	Intermediate Similarity	NPD2231	Phase 2
0.7133	Intermediate Similarity	NPD2235	Phase 2
0.7117	Intermediate Similarity	NPD7075	Discontinued
0.7115	Intermediate Similarity	NPD1774	Approved
0.7111	Intermediate Similarity	NPD556	Approved
0.7107	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD8127	Discontinued
0.7083	Intermediate Similarity	NPD6582	Phase 2
0.7083	Intermediate Similarity	NPD3685	Discontinued
0.7083	Intermediate Similarity	NPD6583	Phase 3
0.708	Intermediate Similarity	NPD5535	Approved
0.7069	Intermediate Similarity	NPD6842	Approved
0.7069	Intermediate Similarity	NPD6841	Approved
0.7069	Intermediate Similarity	NPD6843	Phase 3
0.7063	Intermediate Similarity	NPD4380	Phase 2
0.7051	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2674	Phase 3
0.7047	Intermediate Similarity	NPD4062	Phase 3
0.7039	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7033	Discontinued
0.7037	Intermediate Similarity	NPD1465	Phase 2
0.7033	Intermediate Similarity	NPD7680	Approved
0.7032	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7526	Approved
0.7025	Intermediate Similarity	NPD52	Approved
0.7025	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4140	Approved
0.7	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3496	Discontinued
0.6987	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5241	Discontinued
0.6982	Remote Similarity	NPD3751	Discontinued
0.6981	Remote Similarity	NPD2122	Discontinued
0.698	Remote Similarity	NPD5718	Phase 2
0.6974	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7906	Approved
0.6966	Remote Similarity	NPD5327	Phase 3
0.6966	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD27	Approved
0.6964	Remote Similarity	NPD2489	Approved
0.6962	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3536	Discontinued
0.6962	Remote Similarity	NPD7447	Phase 1
0.6954	Remote Similarity	NPD5124	Phase 1
0.6954	Remote Similarity	NPD1933	Approved
0.6954	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3540	Phase 1
0.6946	Remote Similarity	NPD6071	Discontinued
0.6944	Remote Similarity	NPD422	Phase 1
0.6936	Remote Similarity	NPD7312	Approved
0.6936	Remote Similarity	NPD7313	Approved
0.6936	Remote Similarity	NPD7311	Approved
0.6936	Remote Similarity	NPD7310	Approved
0.6933	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3179	Approved
0.6913	Remote Similarity	NPD3180	Approved
0.6909	Remote Similarity	NPD5604	Discontinued
0.6908	Remote Similarity	NPD3054	Approved
0.6908	Remote Similarity	NPD3052	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