NPASS Compound

Structure

NPC228907 OpenBabel07101718202D 30 32 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -5.1962 4.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 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 -5.1962 3.0000 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 -6.0622 2.5000 0.0000 C 0 0 2 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 -6.0622 1.5000 0.0000 C 0 0 1 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 -5.1962 1.0000 0.0000 C 0 0 2 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 -4.3301 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 -6.0622 4.5000 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 -6.9282 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 -6.9282 1.0000 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 -5.1962 -0.0000 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 -3.4641 1.0000 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 -4.3301 2.5000 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 7 2 0 0 0 0 4 8 2 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 8 1 0 0 0 0 7 27 1 0 0 0 0 8 28 1 0 0 0 0 9 5 1 1 0 0 0 9 11 1 0 0 0 0 9 29 1 0 0 0 0 10 6 1 6 0 0 0 10 12 1 0 0 0 0 10 30 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 6 0 0 0 12 14 1 0 0 0 0 12 22 1 1 0 0 0 13 15 1 0 0 0 0 13 23 1 1 0 0 0 14 16 1 0 0 0 0 14 24 1 6 0 0 0 15 17 1 0 0 0 0 15 25 1 6 0 0 0 16 18 1 0 0 0 0 16 26 1 1 0 0 0 17 27 1 1 0 0 0 17 29 1 0 0 0 0 18 28 1 6 0 0 0 18 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.14
Volume:	391.788
LogP:	-1.567
LogD:	-1.671
LogS:	-0.854
# Rotatable Bonds:	6
TPSA:	198.76
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.216
Synthetic Accessibility Score:	4.149
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.45
MDCK Permeability:	8.949993934947997e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.812
Human Intestinal Absorption (HIA):	0.903
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.192
Plasma Protein Binding (PPB):	28.691884994506836%
Volume Distribution (VD):	0.422
Pgp-substrate:	33.60203552246094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.019
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.197
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	1.015
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.283
Human Hepatotoxicity (H-HT):	0.023
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.155
Carcinogencity:	0.073
Eye Corrosion:	0.003
Eye Irritation:	0.039
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC228907

Natural Product ID:	NPC228907
*Common Name:**	Pyrocatechol-O-Beta-D-Diglucopyranoside
IUPAC Name:	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	QWZXKMQLRBUBMH-NNUBVHJDSA-N
Standard InCHI:	InChI=1S/C18H26O12/c19-5-9-11(21)13(23)15(25)17(29-9)27-7-3-1-2-4-8(7)28-18-16(26)14(24)12(22)10(6-20)30-18/h1-4,9-26H,5-6H2/t9-,10-,11-,12-,13+,14+,15-,16-,17-,18-/m1/s1
SMILES:	c1ccc(c(c1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512797
PubChem CID:	44577197
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
NPO9317	Itoa orientalis	Species	Salicaceae	Eukaryota	bark, twigs, and leaves	n.a.	n.a.	PMID[18412396]
NPO9317	Itoa orientalis	Species	Salicaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	54.3	%	PMID[469464]

☑ 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 NPC228907 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	365
0.1-0.2	2021
0.2-0.3	7076
0.3-0.4	11622
0.4-0.5	6605
0.5-0.6	9458
0.6-0.7	4538
0.7-0.8	899
0.8-0.85	83
0.85-0.9	20
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9402	High Similarity	NPC25817
0.9381	High Similarity	NPC9248
0.9316	High Similarity	NPC217854
0.9244	High Similarity	NPC298845
0.9167	High Similarity	NPC37074
0.9091	High Similarity	NPC247146
0.9083	High Similarity	NPC189589
0.9083	High Similarity	NPC469622
0.906	High Similarity	NPC276195
0.8983	High Similarity	NPC57751
0.8947	High Similarity	NPC142319
0.8943	High Similarity	NPC60756
0.8917	High Similarity	NPC221090
0.8908	High Similarity	NPC152722
0.8871	High Similarity	NPC9912
0.8871	High Similarity	NPC287780
0.8852	High Similarity	NPC469621
0.8833	High Similarity	NPC192810
0.879	High Similarity	NPC208769
0.878	High Similarity	NPC302378
0.877	High Similarity	NPC171533
0.873	High Similarity	NPC60982
0.871	High Similarity	NPC248355
0.8661	High Similarity	NPC87696
0.864	High Similarity	NPC472024
0.864	High Similarity	NPC80600
0.8594	High Similarity	NPC470236
0.8583	High Similarity	NPC469412
0.8583	High Similarity	NPC198734
0.856	High Similarity	NPC26653
0.856	High Similarity	NPC270849
0.856	High Similarity	NPC166040
0.8527	High Similarity	NPC164857
0.8516	High Similarity	NPC187194
0.8516	High Similarity	NPC476411
0.8504	High Similarity	NPC162093
0.85	High Similarity	NPC469708
0.85	High Similarity	NPC60589
0.8455	Intermediate Similarity	NPC287429
0.8443	Intermediate Similarity	NPC476142
0.8438	Intermediate Similarity	NPC49074
0.8438	Intermediate Similarity	NPC25821
0.843	Intermediate Similarity	NPC269242
0.8425	Intermediate Similarity	NPC166168
0.8413	Intermediate Similarity	NPC307110
0.84	Intermediate Similarity	NPC140750
0.8387	Intermediate Similarity	NPC470510
0.8372	Intermediate Similarity	NPC35731
0.8361	Intermediate Similarity	NPC226712
0.8333	Intermediate Similarity	NPC202700
0.8333	Intermediate Similarity	NPC106944
0.8321	Intermediate Similarity	NPC65530
0.8321	Intermediate Similarity	NPC59324
0.8321	Intermediate Similarity	NPC470413
0.8321	Intermediate Similarity	NPC138738
0.832	Intermediate Similarity	NPC233559
0.8308	Intermediate Similarity	NPC55040
0.8295	Intermediate Similarity	NPC215833
0.8295	Intermediate Similarity	NPC69513
0.8281	Intermediate Similarity	NPC65942
0.8281	Intermediate Similarity	NPC248307
0.8268	Intermediate Similarity	NPC295970
0.8258	Intermediate Similarity	NPC212770
0.8258	Intermediate Similarity	NPC98777
0.8244	Intermediate Similarity	NPC104167
0.8244	Intermediate Similarity	NPC37468
0.8244	Intermediate Similarity	NPC242028
0.8244	Intermediate Similarity	NPC203230
0.8231	Intermediate Similarity	NPC48863
0.8231	Intermediate Similarity	NPC13745
0.8231	Intermediate Similarity	NPC251981
0.8217	Intermediate Similarity	NPC299144
0.8217	Intermediate Similarity	NPC252833
0.8203	Intermediate Similarity	NPC470079
0.8189	Intermediate Similarity	NPC198487
0.8182	Intermediate Similarity	NPC304152
0.8154	Intermediate Similarity	NPC132895
0.8154	Intermediate Similarity	NPC6836
0.8134	Intermediate Similarity	NPC76871
0.8134	Intermediate Similarity	NPC469661
0.8125	Intermediate Similarity	NPC218003
0.812	Intermediate Similarity	NPC100389
0.8106	Intermediate Similarity	NPC199459
0.8106	Intermediate Similarity	NPC186418
0.8106	Intermediate Similarity	NPC52277
0.8106	Intermediate Similarity	NPC177035
0.8092	Intermediate Similarity	NPC470881
0.8092	Intermediate Similarity	NPC188555
0.8092	Intermediate Similarity	NPC130496
0.8088	Intermediate Similarity	NPC471063
0.8077	Intermediate Similarity	NPC303422
0.8077	Intermediate Similarity	NPC165686
0.8077	Intermediate Similarity	NPC85799
0.8077	Intermediate Similarity	NPC26080
0.8074	Intermediate Similarity	NPC157816
0.8074	Intermediate Similarity	NPC60249
0.8074	Intermediate Similarity	NPC246947
0.8074	Intermediate Similarity	NPC189115
0.8074	Intermediate Similarity	NPC469559
0.8074	Intermediate Similarity	NPC475084
0.806	Intermediate Similarity	NPC210478
0.8047	Intermediate Similarity	NPC40377
0.8047	Intermediate Similarity	NPC146540
0.803	Intermediate Similarity	NPC238243
0.8029	Intermediate Similarity	NPC476864
0.8029	Intermediate Similarity	NPC476869
0.8029	Intermediate Similarity	NPC476868
0.8029	Intermediate Similarity	NPC476866
0.8015	Intermediate Similarity	NPC115022
0.8015	Intermediate Similarity	NPC46092
0.8015	Intermediate Similarity	NPC478239
0.8015	Intermediate Similarity	NPC470950
0.8015	Intermediate Similarity	NPC185307
0.8015	Intermediate Similarity	NPC294166
0.8015	Intermediate Similarity	NPC252169
0.8	Intermediate Similarity	NPC473412
0.8	Intermediate Similarity	NPC121376
0.8	Intermediate Similarity	NPC469698
0.8	Intermediate Similarity	NPC186406
0.7985	Intermediate Similarity	NPC156376
0.7984	Intermediate Similarity	NPC97326
0.7971	Intermediate Similarity	NPC125755
0.7971	Intermediate Similarity	NPC476865
0.7971	Intermediate Similarity	NPC276753
0.7971	Intermediate Similarity	NPC205796
0.797	Intermediate Similarity	NPC40664
0.797	Intermediate Similarity	NPC157554
0.797	Intermediate Similarity	NPC469383
0.797	Intermediate Similarity	NPC138350
0.797	Intermediate Similarity	NPC3293
0.797	Intermediate Similarity	NPC197723
0.797	Intermediate Similarity	NPC165482
0.7969	Intermediate Similarity	NPC198798
0.7956	Intermediate Similarity	NPC76176
0.7956	Intermediate Similarity	NPC473045
0.7956	Intermediate Similarity	NPC470235
0.7956	Intermediate Similarity	NPC476867
0.7956	Intermediate Similarity	NPC79429
0.7956	Intermediate Similarity	NPC129417
0.7956	Intermediate Similarity	NPC232228
0.7956	Intermediate Similarity	NPC25292
0.7956	Intermediate Similarity	NPC469313
0.7956	Intermediate Similarity	NPC138227
0.7956	Intermediate Similarity	NPC217635
0.7956	Intermediate Similarity	NPC168579
0.7956	Intermediate Similarity	NPC283995
0.7956	Intermediate Similarity	NPC471667
0.7955	Intermediate Similarity	NPC107478
0.7953	Intermediate Similarity	NPC12308
0.7941	Intermediate Similarity	NPC476356
0.7939	Intermediate Similarity	NPC470270
0.7914	Intermediate Similarity	NPC52740
0.791	Intermediate Similarity	NPC195196
0.791	Intermediate Similarity	NPC87777
0.791	Intermediate Similarity	NPC262328
0.7907	Intermediate Similarity	NPC72529
0.7899	Intermediate Similarity	NPC161700
0.7899	Intermediate Similarity	NPC22150
0.7899	Intermediate Similarity	NPC43508
0.7899	Intermediate Similarity	NPC279298
0.7899	Intermediate Similarity	NPC475096
0.7899	Intermediate Similarity	NPC38041
0.7899	Intermediate Similarity	NPC469586
0.7899	Intermediate Similarity	NPC18979
0.7899	Intermediate Similarity	NPC476301
0.7899	Intermediate Similarity	NPC277867
0.7895	Intermediate Similarity	NPC79957
0.7895	Intermediate Similarity	NPC320259
0.7883	Intermediate Similarity	NPC473044
0.7883	Intermediate Similarity	NPC278961
0.7883	Intermediate Similarity	NPC37793
0.7883	Intermediate Similarity	NPC113680
0.7881	Intermediate Similarity	NPC276061
0.7881	Intermediate Similarity	NPC474148
0.7876	Intermediate Similarity	NPC314803
0.7869	Intermediate Similarity	NPC175771
0.7868	Intermediate Similarity	NPC472711
0.7868	Intermediate Similarity	NPC471908
0.7863	Intermediate Similarity	NPC475067
0.7857	Intermediate Similarity	NPC116229
0.7852	Intermediate Similarity	NPC226005
0.7851	Intermediate Similarity	NPC313193
0.7846	Intermediate Similarity	NPC5851
0.7846	Intermediate Similarity	NPC86030
0.7842	Intermediate Similarity	NPC112861
0.7842	Intermediate Similarity	NPC190714
0.7842	Intermediate Similarity	NPC199928
0.7842	Intermediate Similarity	NPC99515
0.784	Intermediate Similarity	NPC205850
0.7836	Intermediate Similarity	NPC172818
0.7836	Intermediate Similarity	NPC166180
0.7836	Intermediate Similarity	NPC25695
0.7826	Intermediate Similarity	NPC292443
0.7823	Intermediate Similarity	NPC214289
0.782	Intermediate Similarity	NPC471029
0.782	Intermediate Similarity	NPC34456
0.7815	Intermediate Similarity	NPC30563
0.781	Intermediate Similarity	NPC477800
0.781	Intermediate Similarity	NPC140502
0.781	Intermediate Similarity	NPC477794

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 NPC228907 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	955
0.2-0.3	2619
0.3-0.4	2746
0.4-0.5	1506
0.5-0.6	828
0.6-0.7	190
0.7-0.8	12
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8378	Intermediate Similarity	NPD291	Approved
0.8361	Intermediate Similarity	NPD1091	Approved
0.819	Intermediate Similarity	NPD556	Approved
0.7727	Intermediate Similarity	NPD9365	Approved
0.7552	Intermediate Similarity	NPD1653	Approved
0.7391	Intermediate Similarity	NPD3454	Phase 3
0.7368	Intermediate Similarity	NPD9296	Approved
0.7357	Intermediate Similarity	NPD6674	Discontinued
0.7338	Intermediate Similarity	NPD7266	Discontinued
0.7279	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1613	Approved
0.7273	Intermediate Similarity	NPD9552	Approved
0.7273	Intermediate Similarity	NPD290	Approved
0.7266	Intermediate Similarity	NPD1357	Approved
0.7244	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD3705	Approved
0.7222	Intermediate Similarity	NPD191	Approved
0.7214	Intermediate Similarity	NPD521	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3027	Phase 3
0.712	Intermediate Similarity	NPD7843	Approved
0.7111	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5058	Phase 3
0.7073	Intermediate Similarity	NPD2684	Approved
0.7067	Intermediate Similarity	NPD8455	Phase 2
0.7054	Intermediate Similarity	NPD7534	Approved
0.7054	Intermediate Similarity	NPD7533	Approved
0.7025	Intermediate Similarity	NPD9501	Approved
0.7	Intermediate Similarity	NPD1798	Approved
0.7	Intermediate Similarity	NPD1797	Approved
0.6985	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7054	Approved
0.6953	Remote Similarity	NPD7157	Approved
0.6918	Remote Similarity	NPD7472	Approved
0.6918	Remote Similarity	NPD7074	Phase 3
0.6912	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4538	Approved
0.6879	Remote Similarity	NPD4536	Approved
0.6879	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1102	Approved
0.6846	Remote Similarity	NPD1103	Approved
0.6831	Remote Similarity	NPD5588	Approved
0.6831	Remote Similarity	NPD5960	Phase 3
0.6818	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3818	Discontinued
0.679	Remote Similarity	NPD7808	Phase 3
0.6788	Remote Similarity	NPD2250	Discontinued
0.6783	Remote Similarity	NPD9295	Approved
0.6774	Remote Similarity	NPD968	Approved
0.677	Remote Similarity	NPD6797	Phase 2
0.6765	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7097	Phase 1
0.6759	Remote Similarity	NPD1652	Phase 2
0.6741	Remote Similarity	NPD2983	Phase 2
0.6741	Remote Similarity	NPD2982	Phase 2
0.6728	Remote Similarity	NPD7251	Discontinued
0.6714	Remote Similarity	NPD6233	Phase 2
0.6692	Remote Similarity	NPD5126	Approved
0.6692	Remote Similarity	NPD5125	Phase 3
0.6692	Remote Similarity	NPD5846	Approved
0.6692	Remote Similarity	NPD6516	Phase 2
0.6691	Remote Similarity	NPD8651	Approved
0.6688	Remote Similarity	NPD7199	Phase 2
0.6687	Remote Similarity	NPD7228	Approved
0.6687	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2981	Phase 2
0.6667	Remote Similarity	NPD1548	Phase 1
0.6667	Remote Similarity	NPD2861	Phase 2
0.6667	Remote Similarity	NPD37	Approved
0.6645	Remote Similarity	NPD4965	Approved
0.6645	Remote Similarity	NPD4966	Approved
0.6645	Remote Similarity	NPD4967	Phase 2
0.6644	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD228	Approved
0.6621	Remote Similarity	NPD1375	Discontinued
0.662	Remote Similarity	NPD1933	Approved
0.6619	Remote Similarity	NPD4908	Phase 1
0.6618	Remote Similarity	NPD3685	Discontinued
0.6594	Remote Similarity	NPD5647	Approved
0.6593	Remote Similarity	NPD1610	Phase 2
0.6577	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1774	Approved
0.6571	Remote Similarity	NPD3179	Approved
0.6571	Remote Similarity	NPD3180	Approved
0.6562	Remote Similarity	NPD2673	Approved
0.6562	Remote Similarity	NPD2671	Approved
0.6561	Remote Similarity	NPD6234	Discontinued
0.6547	Remote Similarity	NPD3018	Phase 2
0.6547	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5283	Phase 1
0.6525	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6798	Discontinued
0.6524	Remote Similarity	NPD7685	Pre-registration
0.6524	Remote Similarity	NPD7240	Approved
0.6522	Remote Similarity	NPD2082	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6362	Approved
0.6519	Remote Similarity	NPD155	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4340	Discontinued
0.65	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD9299	Approved
0.6483	Remote Similarity	NPD7033	Discontinued
0.646	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6166	Phase 2
0.646	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD2224	Approved
0.6458	Remote Similarity	NPD2223	Approved
0.6458	Remote Similarity	NPD6653	Approved
0.6457	Remote Similarity	NPD1358	Approved
0.6452	Remote Similarity	NPD3382	Approved
0.6452	Remote Similarity	NPD3383	Approved
0.6452	Remote Similarity	NPD1934	Approved
0.6452	Remote Similarity	NPD3384	Approved
0.6447	Remote Similarity	NPD2122	Discontinued
0.6443	Remote Similarity	NPD2677	Approved
0.6439	Remote Similarity	NPD6671	Approved
0.6438	Remote Similarity	NPD3787	Discontinued
0.6433	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD2235	Phase 2
0.6423	Remote Similarity	NPD2231	Phase 2
0.6419	Remote Similarity	NPD4237	Approved
0.6419	Remote Similarity	NPD4236	Phase 3
0.6414	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.641	Remote Similarity	NPD9094	Approved
0.641	Remote Similarity	NPD2978	Approved
0.641	Remote Similarity	NPD2977	Approved
0.6408	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD3687	Approved
0.6405	Remote Similarity	NPD3686	Approved
0.6403	Remote Similarity	NPD9549	Phase 2
0.6403	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5756	Phase 2
0.6397	Remote Similarity	NPD915	Approved
0.6395	Remote Similarity	NPD5763	Approved
0.6395	Remote Similarity	NPD5762	Approved
0.6389	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5124	Phase 1
0.6385	Remote Similarity	NPD969	Suspended
0.6377	Remote Similarity	NPD4749	Approved
0.6376	Remote Similarity	NPD4535	Phase 3
0.6376	Remote Similarity	NPD4628	Phase 3
0.6369	Remote Similarity	NPD3817	Phase 2
0.6364	Remote Similarity	NPD3530	Approved
0.6364	Remote Similarity	NPD4062	Phase 3
0.6364	Remote Similarity	NPD3532	Approved
0.6364	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3531	Approved
0.6351	Remote Similarity	NPD2424	Discontinued
0.6347	Remote Similarity	NPD8312	Approved
0.6347	Remote Similarity	NPD8313	Approved
0.6343	Remote Similarity	NPD5536	Phase 2
0.634	Remote Similarity	NPD5403	Approved
0.6336	Remote Similarity	NPD821	Approved
0.6336	Remote Similarity	NPD5535	Approved
0.6333	Remote Similarity	NPD6190	Approved
0.6331	Remote Similarity	NPD3225	Approved
0.6325	Remote Similarity	NPD6559	Discontinued
0.6324	Remote Similarity	NPD1778	Approved
0.6319	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD1558	Phase 1
0.6319	Remote Similarity	NPD3620	Phase 2
0.6316	Remote Similarity	NPD4123	Phase 3
0.6316	Remote Similarity	NPD5401	Approved
0.6309	Remote Similarity	NPD5177	Phase 3
0.6309	Remote Similarity	NPD4162	Approved
0.6309	Remote Similarity	NPD5061	Approved
0.6309	Remote Similarity	NPD5062	Approved
0.6306	Remote Similarity	NPD5772	Approved
0.6306	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5773	Approved
0.6294	Remote Similarity	NPD6843	Phase 3
0.6294	Remote Similarity	NPD6841	Approved
0.6294	Remote Similarity	NPD6842	Approved
0.6291	Remote Similarity	NPD3122	Phase 3
0.6289	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD3496	Discontinued
0.6276	Remote Similarity	NPD5735	Approved
0.6276	Remote Similarity	NPD6355	Discontinued
0.6267	Remote Similarity	NPD4110	Phase 3
0.6267	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD4108	Discontinued
0.625	Remote Similarity	NPD6382	Discontinued
0.625	Remote Similarity	NPD3134	Approved
0.6241	Remote Similarity	NPD558	Phase 2
0.6234	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD776	Approved
0.6232	Remote Similarity	NPD422	Phase 1
0.6224	Remote Similarity	NPD4625	Phase 3
0.6224	Remote Similarity	NPD7095	Approved
0.6218	Remote Similarity	NPD4380	Phase 2
0.6218	Remote Similarity	NPD4675	Approved
0.6218	Remote Similarity	NPD4678	Approved
0.6212	Remote Similarity	NPD769	Approved
0.6209	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4060	Phase 1
0.6207	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD2801	Approved
0.6202	Remote Similarity	NPD5374	Approved
0.6202	Remote Similarity	NPD5373	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