NPASS Compound

Structure

NPC36927 OpenBabel07101718292D 24 25 0 0 1 0 0 0 0 0999 V2000 -4.3301 -2.5000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -5.1962 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 -5.1962 -0.0000 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 -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 -3.4641 -1.0000 0.0000 N 0 0 0 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 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 -6.0622 0.5000 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 23 1 0 0 0 0 4 1 1 6 0 0 0 4 7 1 0 0 0 0 4 14 1 0 0 0 0 5 3 1 1 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 2 1 1 0 0 0 6 9 1 0 0 0 0 6 24 1 0 0 0 0 7 10 1 0 0 0 0 7 17 1 1 0 0 0 8 10 1 0 0 0 0 8 18 1 1 0 0 0 9 11 1 0 0 0 0 9 19 1 6 0 0 0 10 20 1 6 0 0 0 11 12 1 0 0 0 0 11 21 1 1 0 0 0 12 13 1 0 0 0 0 12 22 1 6 0 0 0 13 23 1 1 0 0 0 13 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.15
Volume:	315.19
LogP:	-3.04
LogD:	-2.725
LogS:	0.052
# Rotatable Bonds:	5
TPSA:	192.33
# H-Bond Aceptor:	11
# H-Bond Donor:	9
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.228
Synthetic Accessibility Score:	4.608
Fsp3:	1.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.048
MDCK Permeability:	0.00013116469199303538
Pgp-inhibitor:	0.001
Pgp-substrate:	0.88
Human Intestinal Absorption (HIA):	0.987
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202
Plasma Protein Binding (PPB):	14.67615795135498%
Volume Distribution (VD):	0.258
Pgp-substrate:	73.88752746582031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.019
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	1.073
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.175
Human Hepatotoxicity (H-HT):	0.382
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.115
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.305
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.034

Download Data

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

Natural Product: NPC36927

Natural Product ID:	NPC36927
*Common Name:**	7-O-B-D-Glucopyranosyl-A-Homonojirimycin
IUPAC Name:	(2R,3R,4S,5S,6R)-2-(hydroxymethyl)-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]piperidine-3,4,5-triol
Synonyms:
Standard InCHIKey:	VCIPQQCYKMORDY-KBYFLBCBSA-N
Standard InCHI:	InChI=1S/C13H25NO10/c15-1-4-7(17)10(20)8(18)5(14-4)3-23-13-12(22)11(21)9(19)6(2-16)24-13/h4-22H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11+,12-,13-/m1/s1
SMILES:	C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)N1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478209
PubChem CID:	457676
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:0002207] O-glycosyl compounds

*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
NPO25280	Suregada glomerulata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[18205316]
NPO25280	Suregada glomerulata	Species	Euphorbiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23993676]
NPO25280	Suregada glomerulata	Species	Euphorbiaceae	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	6
Others	10

Activity Type	# Activity
Individual Protein	6
Organism	8
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	IC50	=	600.0	nM	PMID[501036]
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	IC50	=	2600.0	nM	PMID[501036]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	IC50	=	18000.0	nM	PMID[501036]
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	Inhibition	<	50.0	%	PMID[501036]
NPT3906	Individual Protein	Glycogen debranching enzyme	Oryctolagus cuniculus	IC50	=	6100.0	nM	PMID[501036]
NPT671	Individual Protein	Acidic alpha-glucosidase	Rattus norvegicus	IC50	=	380.0	nM	PMID[501036]
NPT2	Others	Unspecified		Inhibition	<	50.0	%	PMID[501036]
NPT32	Organism	Mus musculus	Mus musculus	AUC	=	3408000.0	ng.hr.mL-1	PMID[501037]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	146.8	mg/dl	PMID[501037]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	204.1	mg/dl	PMID[501037]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	187.1	mg/dl	PMID[501037]
NPT32	Organism	Mus musculus	Mus musculus	AUC	=	2584000.0	ng.hr.mL-1	PMID[501037]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	133.3	mg/dl	PMID[501037]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	135.1	mg/dl	PMID[501037]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	130.8	mg/dl	PMID[501037]
NPT2	Others	Unspecified		IC50	=	4220.0	nM	PMID[501037]

☑ 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 NPC36927 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	263
0.1-0.2	8336
0.2-0.3	21764
0.3-0.4	9715
0.4-0.5	2035
0.5-0.6	398
0.6-0.7	104
0.7-0.8	71
0.8-0.85	1
0.85-0.9	4
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC271772
0.9733	High Similarity	NPC70574
0.96	High Similarity	NPC98750
0.9091	High Similarity	NPC150557
0.8902	High Similarity	NPC306838
0.8875	High Similarity	NPC165119
0.8861	High Similarity	NPC471420
0.8734	High Similarity	NPC83248
0.8734	High Similarity	NPC100204
0.8049	Intermediate Similarity	NPC318258
0.8026	Intermediate Similarity	NPC471418
0.7922	Intermediate Similarity	NPC268922
0.7867	Intermediate Similarity	NPC198341
0.7867	Intermediate Similarity	NPC223386
0.7867	Intermediate Similarity	NPC471892
0.7867	Intermediate Similarity	NPC142290
0.7867	Intermediate Similarity	NPC471780
0.7867	Intermediate Similarity	NPC75435
0.7766	Intermediate Similarity	NPC315036
0.7763	Intermediate Similarity	NPC303798
0.7763	Intermediate Similarity	NPC286851
0.7727	Intermediate Similarity	NPC470282
0.7722	Intermediate Similarity	NPC476694
0.7722	Intermediate Similarity	NPC476696
0.7722	Intermediate Similarity	NPC476695
0.7662	Intermediate Similarity	NPC129100
0.7662	Intermediate Similarity	NPC291650
0.7662	Intermediate Similarity	NPC322801
0.76	Intermediate Similarity	NPC306462
0.76	Intermediate Similarity	NPC150680
0.76	Intermediate Similarity	NPC69669
0.76	Intermediate Similarity	NPC22774
0.76	Intermediate Similarity	NPC218150
0.76	Intermediate Similarity	NPC2432
0.7579	Intermediate Similarity	NPC471628
0.7579	Intermediate Similarity	NPC56298
0.75	Intermediate Similarity	NPC316807
0.7442	Intermediate Similarity	NPC315969
0.7356	Intermediate Similarity	NPC263058
0.7333	Intermediate Similarity	NPC43850
0.7333	Intermediate Similarity	NPC477060
0.7333	Intermediate Similarity	NPC314007
0.7333	Intermediate Similarity	NPC123746
0.7333	Intermediate Similarity	NPC314408
0.7308	Intermediate Similarity	NPC315980
0.7284	Intermediate Similarity	NPC285014
0.7284	Intermediate Similarity	NPC299603
0.7284	Intermediate Similarity	NPC255535
0.7284	Intermediate Similarity	NPC137554
0.7284	Intermediate Similarity	NPC28959
0.7273	Intermediate Similarity	NPC471419
0.7273	Intermediate Similarity	NPC163134
0.7222	Intermediate Similarity	NPC313552
0.72	Intermediate Similarity	NPC143809
0.72	Intermediate Similarity	NPC76726
0.72	Intermediate Similarity	NPC290106
0.72	Intermediate Similarity	NPC193593
0.7191	Intermediate Similarity	NPC125253
0.7191	Intermediate Similarity	NPC192025
0.7191	Intermediate Similarity	NPC253975
0.7174	Intermediate Similarity	NPC176381
0.7174	Intermediate Similarity	NPC195969
0.7143	Intermediate Similarity	NPC214376
0.7115	Intermediate Similarity	NPC314306
0.7111	Intermediate Similarity	NPC83839
0.7065	Intermediate Similarity	NPC470284
0.7	Intermediate Similarity	NPC221148
0.6988	Remote Similarity	NPC474468
0.6979	Remote Similarity	NPC330590
0.6951	Remote Similarity	NPC473710
0.6951	Remote Similarity	NPC223174
0.6951	Remote Similarity	NPC475694
0.6951	Remote Similarity	NPC327753
0.6951	Remote Similarity	NPC327486
0.6947	Remote Similarity	NPC315334
0.6875	Remote Similarity	NPC116377
0.6875	Remote Similarity	NPC473952
0.6875	Remote Similarity	NPC101746
0.6875	Remote Similarity	NPC69798
0.6875	Remote Similarity	NPC77191
0.6842	Remote Similarity	NPC204709
0.6842	Remote Similarity	NPC328646
0.6813	Remote Similarity	NPC476523
0.6753	Remote Similarity	NPC233364
0.6753	Remote Similarity	NPC471421
0.6753	Remote Similarity	NPC170172
0.6707	Remote Similarity	NPC126664
0.6707	Remote Similarity	NPC171850
0.6707	Remote Similarity	NPC34291
0.6701	Remote Similarity	NPC470283
0.6606	Remote Similarity	NPC313813
0.6604	Remote Similarity	NPC121479
0.6604	Remote Similarity	NPC57436
0.66	Remote Similarity	NPC315170
0.6591	Remote Similarity	NPC314772
0.6591	Remote Similarity	NPC314968
0.6543	Remote Similarity	NPC474928
0.6533	Remote Similarity	NPC145112
0.6533	Remote Similarity	NPC242073
0.6533	Remote Similarity	NPC157514
0.6533	Remote Similarity	NPC269166
0.6533	Remote Similarity	NPC165198
0.6533	Remote Similarity	NPC107914
0.6533	Remote Similarity	NPC58629
0.6533	Remote Similarity	NPC246558
0.6533	Remote Similarity	NPC67660
0.6533	Remote Similarity	NPC89145
0.6495	Remote Similarity	NPC270005
0.6495	Remote Similarity	NPC208537
0.6447	Remote Similarity	NPC303727
0.641	Remote Similarity	NPC472025
0.6383	Remote Similarity	NPC469363
0.6375	Remote Similarity	NPC477763
0.6375	Remote Similarity	NPC477750
0.6375	Remote Similarity	NPC477757
0.6375	Remote Similarity	NPC62507
0.6375	Remote Similarity	NPC477755
0.6375	Remote Similarity	NPC8087
0.6375	Remote Similarity	NPC477762
0.6375	Remote Similarity	NPC477753
0.6341	Remote Similarity	NPC233034
0.6327	Remote Similarity	NPC475603
0.6327	Remote Similarity	NPC61894
0.6321	Remote Similarity	NPC317534
0.6311	Remote Similarity	NPC188453
0.6311	Remote Similarity	NPC42320
0.6296	Remote Similarity	NPC17455
0.6273	Remote Similarity	NPC241597
0.6267	Remote Similarity	NPC326533
0.6261	Remote Similarity	NPC20035
0.625	Remote Similarity	NPC227622
0.6196	Remote Similarity	NPC219340
0.6173	Remote Similarity	NPC57846
0.6173	Remote Similarity	NPC30126
0.6173	Remote Similarity	NPC474014
0.6125	Remote Similarity	NPC34877
0.6125	Remote Similarity	NPC317023
0.6125	Remote Similarity	NPC290179
0.6104	Remote Similarity	NPC130683
0.6104	Remote Similarity	NPC323361
0.6092	Remote Similarity	NPC306973
0.6076	Remote Similarity	NPC8979
0.6076	Remote Similarity	NPC311668
0.6076	Remote Similarity	NPC10262
0.6076	Remote Similarity	NPC148424
0.6076	Remote Similarity	NPC65832
0.6071	Remote Similarity	NPC471760
0.6071	Remote Similarity	NPC471761
0.6071	Remote Similarity	NPC190418
0.6066	Remote Similarity	NPC262050
0.6053	Remote Similarity	NPC124963
0.6053	Remote Similarity	NPC233726
0.6053	Remote Similarity	NPC23134
0.6049	Remote Similarity	NPC143326
0.6038	Remote Similarity	NPC314413
0.6038	Remote Similarity	NPC314398
0.6038	Remote Similarity	NPC239705
0.602	Remote Similarity	NPC292345
0.6019	Remote Similarity	NPC137453
0.6	Remote Similarity	NPC477002
0.6	Remote Similarity	NPC477751
0.6	Remote Similarity	NPC477752
0.6	Remote Similarity	NPC477756
0.6	Remote Similarity	NPC477764
0.5983	Remote Similarity	NPC94319
0.5981	Remote Similarity	NPC62845
0.5981	Remote Similarity	NPC322449
0.5981	Remote Similarity	NPC166242
0.5981	Remote Similarity	NPC189854
0.5981	Remote Similarity	NPC92874
0.5977	Remote Similarity	NPC163538
0.5977	Remote Similarity	NPC115800
0.5955	Remote Similarity	NPC208657
0.593	Remote Similarity	NPC477761
0.593	Remote Similarity	NPC107224
0.593	Remote Similarity	NPC477759
0.593	Remote Similarity	NPC474469
0.593	Remote Similarity	NPC477760
0.593	Remote Similarity	NPC477758
0.593	Remote Similarity	NPC477754
0.5926	Remote Similarity	NPC10897
0.5926	Remote Similarity	NPC325900
0.5922	Remote Similarity	NPC189629
0.592	Remote Similarity	NPC297058
0.5905	Remote Similarity	NPC271207
0.5905	Remote Similarity	NPC206711
0.5905	Remote Similarity	NPC225978
0.5905	Remote Similarity	NPC255175
0.59	Remote Similarity	NPC209047
0.59	Remote Similarity	NPC139782
0.59	Remote Similarity	NPC43074
0.59	Remote Similarity	NPC74672
0.59	Remote Similarity	NPC242503
0.5888	Remote Similarity	NPC55336
0.5882	Remote Similarity	NPC68327
0.5882	Remote Similarity	NPC296686
0.5872	Remote Similarity	NPC59589
0.5862	Remote Similarity	NPC475715
0.5862	Remote Similarity	NPC97736
0.5862	Remote Similarity	NPC67099

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 NPC36927 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	87
0.1-0.2	2760
0.2-0.3	4538
0.3-0.4	1371
0.4-0.5	216
0.5-0.6	81
0.6-0.7	65
0.7-0.8	32
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7662	Intermediate Similarity	NPD9031	Approved
0.7662	Intermediate Similarity	NPD9033	Approved
0.7662	Intermediate Similarity	NPD9032	Approved
0.7662	Intermediate Similarity	NPD9030	Approved
0.76	Intermediate Similarity	NPD9026	Phase 2
0.76	Intermediate Similarity	NPD9029	Phase 3
0.76	Intermediate Similarity	NPD9027	Phase 3
0.76	Intermediate Similarity	NPD9028	Phase 2
0.7579	Intermediate Similarity	NPD4835	Approved
0.7579	Intermediate Similarity	NPD4837	Approved
0.7579	Intermediate Similarity	NPD4838	Approved
0.7579	Intermediate Similarity	NPD4836	Approved
0.7416	Intermediate Similarity	NPD3200	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4282	Approved
0.7347	Intermediate Similarity	NPD8045	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3207	Approved
0.7333	Intermediate Similarity	NPD3208	Approved
0.7333	Intermediate Similarity	NPD3201	Approved
0.7333	Intermediate Similarity	NPD3203	Approved
0.7333	Intermediate Similarity	NPD3202	Approved
0.7333	Intermediate Similarity	NPD3209	Approved
0.7317	Intermediate Similarity	NPD67	Phase 2
0.7317	Intermediate Similarity	NPD9034	Approved
0.7174	Intermediate Similarity	NPD5794	Approved
0.7174	Intermediate Similarity	NPD5798	Approved
0.7174	Intermediate Similarity	NPD5795	Approved
0.7174	Intermediate Similarity	NPD5797	Approved
0.7174	Intermediate Similarity	NPD5796	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2698	Approved
0.7115	Intermediate Similarity	NPD6430	Approved
0.7115	Intermediate Similarity	NPD6429	Approved
0.7105	Intermediate Similarity	NPD9455	Approved
0.71	Intermediate Similarity	NPD2700	Approved
0.7059	Intermediate Similarity	NPD372	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5376	Approved
0.7013	Intermediate Similarity	NPD393	Approved
0.7	Intermediate Similarity	NPD1449	Approved
0.7	Intermediate Similarity	NPD1450	Approved
0.6979	Remote Similarity	NPD5377	Approved
0.6979	Remote Similarity	NPD5378	Approved
0.6979	Remote Similarity	NPD5381	Approved
0.6966	Remote Similarity	NPD882	Phase 2
0.6966	Remote Similarity	NPD883	Phase 2
0.6951	Remote Similarity	NPD9445	Approved
0.6907	Remote Similarity	NPD6428	Approved
0.6857	Remote Similarity	NPD2690	Discontinued
0.6818	Remote Similarity	NPD8347	Approved
0.6818	Remote Similarity	NPD8346	Approved
0.6818	Remote Similarity	NPD8345	Approved
0.6762	Remote Similarity	NPD8087	Discontinued
0.6707	Remote Similarity	NPD9443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3204	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9239	Approved
0.6667	Remote Similarity	NPD9240	Approved
0.6667	Remote Similarity	NPD881	Approved
0.6604	Remote Similarity	NPD4833	Approved
0.6604	Remote Similarity	NPD35	Approved
0.6591	Remote Similarity	NPD9435	Approved
0.6591	Remote Similarity	NPD9434	Approved
0.6588	Remote Similarity	NPD6704	Discontinued
0.6543	Remote Similarity	NPD1457	Discontinued
0.6533	Remote Similarity	NPD891	Phase 3
0.6533	Remote Similarity	NPD892	Phase 3
0.6533	Remote Similarity	NPD893	Approved
0.6533	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD888	Phase 3
0.6509	Remote Similarity	NPD6941	Approved
0.6476	Remote Similarity	NPD8140	Approved
0.6429	Remote Similarity	NPD1446	Phase 3
0.6429	Remote Similarity	NPD1447	Phase 3
0.6346	Remote Similarity	NPD8276	Approved
0.6346	Remote Similarity	NPD8275	Approved
0.6341	Remote Similarity	NPD9440	Discontinued
0.6321	Remote Similarity	NPD8307	Discontinued
0.6306	Remote Similarity	NPD4830	Approved
0.6306	Remote Similarity	NPD4831	Approved
0.6306	Remote Similarity	NPD4832	Approved
0.6289	Remote Similarity	NPD3716	Discontinued
0.6277	Remote Similarity	NPD361	Discontinued
0.6273	Remote Similarity	NPD3731	Phase 3
0.6267	Remote Similarity	NPD905	Approved
0.6267	Remote Similarity	NPD904	Phase 3
0.625	Remote Similarity	NPD8086	Approved
0.625	Remote Similarity	NPD8139	Approved
0.625	Remote Similarity	NPD8138	Approved
0.625	Remote Similarity	NPD8084	Approved
0.625	Remote Similarity	NPD8082	Approved
0.625	Remote Similarity	NPD8085	Approved
0.625	Remote Similarity	NPD8083	Approved
0.6226	Remote Similarity	NPD8393	Approved
0.6211	Remote Similarity	NPD394	Phase 3
0.6173	Remote Similarity	NPD9022	Phase 2
0.6173	Remote Similarity	NPD9024	Phase 2
0.6132	Remote Similarity	NPD8081	Approved
0.6121	Remote Similarity	NPD6436	Phase 3
0.6117	Remote Similarity	NPD2255	Approved
0.6105	Remote Similarity	NPD9401	Discovery
0.6104	Remote Similarity	NPD887	Approved
0.6104	Remote Similarity	NPD895	Approved
0.6104	Remote Similarity	NPD889	Approved
0.6104	Remote Similarity	NPD894	Approved
0.6082	Remote Similarity	NPD4759	Clinical (unspecified phase)
0.602	Remote Similarity	NPD618	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4828	Approved
0.5983	Remote Similarity	NPD4827	Approved
0.5983	Remote Similarity	NPD4826	Approved
0.5976	Remote Similarity	NPD6123	Approved
0.5974	Remote Similarity	NPD2269	Approved
0.5955	Remote Similarity	NPD389	Phase 3
0.5943	Remote Similarity	NPD7140	Approved
0.5943	Remote Similarity	NPD7139	Approved
0.5943	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.593	Remote Similarity	NPD9444	Discontinued
0.5909	Remote Similarity	NPD8306	Approved
0.5909	Remote Similarity	NPD8305	Approved
0.59	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD577	Phase 3
0.5882	Remote Similarity	NPD591	Approved
0.569	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD2267	Suspended
0.5648	Remote Similarity	NPD8301	Approved
0.5648	Remote Similarity	NPD8300	Approved
0.5632	Remote Similarity	NPD374	Approved
0.5632	Remote Similarity	NPD373	Approved
0.5619	Remote Similarity	NPD3190	Approved
0.5619	Remote Similarity	NPD3189	Approved
0.5619	Remote Similarity	NPD3191	Approved
0.561	Remote Similarity	NPD369	Approved
0.56	Remote Similarity	NPD8998	Phase 2
0.56	Remote Similarity	NPD8999	Phase 3
0.56	Remote Similarity	NPD8997	Approved
0.56	Remote Similarity	NPD8993	Phase 1
0.56	Remote Similarity	NPD9000	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