NPASS Compound

Structure

NPC474468 OpenBabel07101719522D 27 27 0 0 1 0 0 0 0 0999 V2000 -4.7017 -5.2300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4449 -4.5609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2248 -1.3685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7507 -4.9210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2370 -3.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4328 -2.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9680 -0.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5917 -3.6338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7722 -1.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 2.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5428 -3.9428 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.3838 -2.6557 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.9801 -2.9136 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7601 0.2788 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5154 -1.2663 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6810 3.2614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2859 -3.2737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1270 -1.9865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9312 -3.2226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5032 0.9479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 11 1 0 0 0 0 5 13 1 0 0 0 0 6 12 1 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 10 1 6 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 15 25 1 1 0 0 0 16 15 1 1 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 1 0 0 0 18 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	395.25
Volume:	392.646
LogP:	-1.805
LogD:	-2.103
LogS:	-0.316
# Rotatable Bonds:	14
TPSA:	173.87
# H-Bond Aceptor:	9
# H-Bond Donor:	9
# Rings:	1
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.145
Synthetic Accessibility Score:	4.648
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.943
MDCK Permeability:	0.00019441121548879892
Pgp-inhibitor:	0.0
Pgp-substrate:	0.686
Human Intestinal Absorption (HIA):	0.886
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.196
Plasma Protein Binding (PPB):	15.78980541229248%
Volume Distribution (VD):	0.572
Pgp-substrate:	60.14103317260742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.317
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.014

ADMET: Excretion

Clearance (CL):	1.473
Half-life (T1/2):	0.764

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.524
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.617
Carcinogencity:	0.002
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.13

Download Data

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

Natural Product: NPC474468

Natural Product ID:	NPC474468
*Common Name:**	Alpha-1-C-(1,10,13-Trihydroxytridecyl)-1,4-Dideoxy-1,4-Imino-D-Arabinitol
IUPAC Name:	(13R)-13-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]tridecane-1,2,7,9,13-pentol
Synonyms:
Standard InCHIKey:	ABLRAGJKLQYRRX-LXHJOMHSSA-N
Standard InCHI:	InChI=1S/C18H37NO8/c20-9-13(24)5-2-1-4-11(22)8-12(23)6-3-7-15(25)16-18(27)17(26)14(10-21)19-16/h11-27H,1-10H2/t11?,12?,13?,14-,15-,16-,17-,18-/m1/s1
SMILES:	OCC(CCCCC(CC(CCC[C@H]([C@H]1N[C@@H]([C@H]([C@@H]1O)O)CO)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469435
PubChem CID:	11773821
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000218] Pyrrolidines

*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
NPO22662	Scilla peruviana	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165148]
NPO22662	Scilla peruviana	Species	Hyacinthaceae	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	8
Others	5

Activity Type	# Activity
Individual Protein	6
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	IC50	=	970000.0	nM	PMID[458326]
NPT509	Individual Protein	Beta-galactosidase	Bos taurus	IC50	=	90.0	nM	PMID[458326]
NPT506	Individual Protein	Beta-mannosidase	Rattus norvegicus	IC50	=	9300.0	nM	PMID[458326]
NPT496	Individual Protein	Alpha-L-fucosidase 1	Bos taurus	Inhibition	<	50.0	%	PMID[458326]
NPT1131	Individual Protein	Alpha-galactosidase	Coffea arabica	Inhibition	<	50.0	%	PMID[458326]
NPT2	Others	Unspecified		IC50	=	265000.0	nM	PMID[458326]
NPT2	Others	Unspecified		IC50	=	220000.0	nM	PMID[458326]
NPT671	Individual Protein	Acidic alpha-glucosidase	Rattus norvegicus	IC50	=	740000.0	nM	PMID[458326]
NPT2	Others	Unspecified		IC50	=	80.0	nM	PMID[458326]
NPT2	Others	Unspecified		IC50	=	6600.0	nM	PMID[458326]
NPT2	Others	Unspecified		Inhibition	<	50.0	%	PMID[458326]

☑ 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 NPC474468 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	222
0.1-0.2	14325
0.2-0.3	19765
0.3-0.4	7041
0.4-0.5	1001
0.5-0.6	221
0.6-0.7	46
0.7-0.8	48
0.8-0.85	12
0.85-0.9	8
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9403	High Similarity	NPC475694
0.9403	High Similarity	NPC473710
0.9091	High Similarity	NPC101746
0.9091	High Similarity	NPC69798
0.9091	High Similarity	NPC77191
0.9091	High Similarity	NPC116377
0.9091	High Similarity	NPC473952
0.8657	High Similarity	NPC474928
0.8485	Intermediate Similarity	NPC8087
0.8485	Intermediate Similarity	NPC62507
0.8451	Intermediate Similarity	NPC476695
0.8451	Intermediate Similarity	NPC299603
0.8451	Intermediate Similarity	NPC285014
0.8451	Intermediate Similarity	NPC255535
0.8451	Intermediate Similarity	NPC476696
0.8451	Intermediate Similarity	NPC28959
0.8451	Intermediate Similarity	NPC137554
0.8451	Intermediate Similarity	NPC476694
0.8286	Intermediate Similarity	NPC471418
0.8209	Intermediate Similarity	NPC57846
0.8209	Intermediate Similarity	NPC30126
0.8209	Intermediate Similarity	NPC474014
0.8169	Intermediate Similarity	NPC268922
0.8056	Intermediate Similarity	NPC115800
0.8056	Intermediate Similarity	NPC163538
0.8025	Intermediate Similarity	NPC306838
0.7975	Intermediate Similarity	NPC165119
0.7887	Intermediate Similarity	NPC184150
0.7887	Intermediate Similarity	NPC141156
0.7879	Intermediate Similarity	NPC10262
0.7879	Intermediate Similarity	NPC311668
0.7879	Intermediate Similarity	NPC65832
0.7857	Intermediate Similarity	NPC471780
0.7857	Intermediate Similarity	NPC142290
0.7857	Intermediate Similarity	NPC75435
0.7857	Intermediate Similarity	NPC198341
0.7857	Intermediate Similarity	NPC471892
0.7857	Intermediate Similarity	NPC223386
0.7778	Intermediate Similarity	NPC306763
0.7778	Intermediate Similarity	NPC74555
0.7778	Intermediate Similarity	NPC266242
0.7778	Intermediate Similarity	NPC474469
0.7778	Intermediate Similarity	NPC126664
0.7778	Intermediate Similarity	NPC254617
0.7778	Intermediate Similarity	NPC34291
0.7746	Intermediate Similarity	NPC303798
0.7746	Intermediate Similarity	NPC315980
0.7746	Intermediate Similarity	NPC286851
0.7746	Intermediate Similarity	NPC294883
0.7746	Intermediate Similarity	NPC12514
0.7671	Intermediate Similarity	NPC473419
0.7671	Intermediate Similarity	NPC475715
0.7671	Intermediate Similarity	NPC475127
0.7639	Intermediate Similarity	NPC59221
0.7612	Intermediate Similarity	NPC8979
0.7595	Intermediate Similarity	NPC83248
0.7595	Intermediate Similarity	NPC100204
0.7571	Intermediate Similarity	NPC22774
0.7571	Intermediate Similarity	NPC218150
0.7571	Intermediate Similarity	NPC69669
0.7571	Intermediate Similarity	NPC2432
0.7571	Intermediate Similarity	NPC150680
0.7571	Intermediate Similarity	NPC306462
0.7424	Intermediate Similarity	NPC272396
0.7361	Intermediate Similarity	NPC233034
0.7324	Intermediate Similarity	NPC17455
0.7222	Intermediate Similarity	NPC163134
0.7222	Intermediate Similarity	NPC471419
0.7143	Intermediate Similarity	NPC193593
0.7143	Intermediate Similarity	NPC76726
0.7143	Intermediate Similarity	NPC290106
0.7143	Intermediate Similarity	NPC143809
0.7059	Intermediate Similarity	NPC275727
0.7015	Intermediate Similarity	NPC123814
0.6988	Remote Similarity	NPC271772
0.6988	Remote Similarity	NPC36927
0.6842	Remote Similarity	NPC171850
0.6829	Remote Similarity	NPC98750
0.6765	Remote Similarity	NPC474322
0.6761	Remote Similarity	NPC204709
0.6747	Remote Similarity	NPC70574
0.6667	Remote Similarity	NPC233364
0.6667	Remote Similarity	NPC170172
0.6667	Remote Similarity	NPC471421
0.6667	Remote Similarity	NPC469363
0.6622	Remote Similarity	NPC145627
0.662	Remote Similarity	NPC471443
0.662	Remote Similarity	NPC471605
0.6582	Remote Similarity	NPC306973
0.6575	Remote Similarity	NPC319131
0.6471	Remote Similarity	NPC471420
0.6458	Remote Similarity	NPC315036
0.6418	Remote Similarity	NPC29222
0.6418	Remote Similarity	NPC121062
0.6418	Remote Similarity	NPC96966
0.6353	Remote Similarity	NPC318258
0.6338	Remote Similarity	NPC471423
0.6338	Remote Similarity	NPC471442
0.6333	Remote Similarity	NPC470282
0.6316	Remote Similarity	NPC313821
0.6282	Remote Similarity	NPC135539
0.6282	Remote Similarity	NPC129100
0.6282	Remote Similarity	NPC221764
0.6282	Remote Similarity	NPC196359
0.6282	Remote Similarity	NPC291650
0.6282	Remote Similarity	NPC322801
0.6282	Remote Similarity	NPC78312
0.6265	Remote Similarity	NPC477002
0.6265	Remote Similarity	NPC3094
0.6264	Remote Similarity	NPC275715
0.6235	Remote Similarity	NPC150557
0.6222	Remote Similarity	NPC313552
0.6203	Remote Similarity	NPC195165
0.6197	Remote Similarity	NPC178263
0.6197	Remote Similarity	NPC277072
0.6197	Remote Similarity	NPC270041
0.6186	Remote Similarity	NPC315170
0.6154	Remote Similarity	NPC214376
0.6122	Remote Similarity	NPC471628
0.6122	Remote Similarity	NPC56298
0.6071	Remote Similarity	NPC212008
0.6071	Remote Similarity	NPC140327
0.6071	Remote Similarity	NPC244539
0.6071	Remote Similarity	NPC51055
0.6071	Remote Similarity	NPC62293
0.6022	Remote Similarity	NPC195969
0.6022	Remote Similarity	NPC176381
0.6	Remote Similarity	NPC216415
0.6	Remote Similarity	NPC313762
0.6	Remote Similarity	NPC192025
0.6	Remote Similarity	NPC476537
0.6	Remote Similarity	NPC125253
0.6	Remote Similarity	NPC253975
0.5976	Remote Similarity	NPC477200
0.5946	Remote Similarity	NPC293551
0.5934	Remote Similarity	NPC83839
0.5909	Remote Similarity	NPC79367
0.5909	Remote Similarity	NPC219340
0.5862	Remote Similarity	NPC473971
0.5862	Remote Similarity	NPC475363
0.5862	Remote Similarity	NPC473972
0.5833	Remote Similarity	NPC315334
0.5816	Remote Similarity	NPC160066
0.5806	Remote Similarity	NPC314408
0.5806	Remote Similarity	NPC43850
0.5806	Remote Similarity	NPC123746
0.5806	Remote Similarity	NPC477060
0.5806	Remote Similarity	NPC314007
0.5802	Remote Similarity	NPC107224
0.5769	Remote Similarity	NPC313272
0.5769	Remote Similarity	NPC319537
0.5755	Remote Similarity	NPC57436
0.5755	Remote Similarity	NPC121479
0.5745	Remote Similarity	NPC470284
0.573	Remote Similarity	NPC207657
0.5714	Remote Similarity	NPC55274
0.5714	Remote Similarity	NPC474627
0.5714	Remote Similarity	NPC320936
0.5714	Remote Similarity	NPC328786
0.5714	Remote Similarity	NPC201338
0.5698	Remote Similarity	NPC264417
0.5698	Remote Similarity	NPC217095
0.5686	Remote Similarity	NPC314387
0.5682	Remote Similarity	NPC316807
0.5679	Remote Similarity	NPC113224
0.5667	Remote Similarity	NPC315969
0.5663	Remote Similarity	NPC327753
0.5663	Remote Similarity	NPC327486
0.5663	Remote Similarity	NPC223174
0.5658	Remote Similarity	NPC302569
0.5658	Remote Similarity	NPC168308
0.5652	Remote Similarity	NPC476523
0.5647	Remote Similarity	NPC208657
0.5647	Remote Similarity	NPC315806
0.5641	Remote Similarity	NPC314510
0.5638	Remote Similarity	NPC52533
0.5631	Remote Similarity	NPC314413
0.5631	Remote Similarity	NPC314398
0.5631	Remote Similarity	NPC239705
0.5604	Remote Similarity	NPC263058

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 NPC474468 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	80
0.1-0.2	3442
0.2-0.3	4086
0.3-0.4	1155
0.4-0.5	277
0.5-0.6	83
0.6-0.7	18
0.7-0.8	8
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
0.8028	Intermediate Similarity	NPD9444	Discontinued
0.7778	Intermediate Similarity	NPD9443	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD9028	Phase 2
0.7571	Intermediate Similarity	NPD9026	Phase 2
0.7571	Intermediate Similarity	NPD9027	Phase 3
0.7571	Intermediate Similarity	NPD9029	Phase 3
0.7536	Intermediate Similarity	NPD9240	Approved
0.7536	Intermediate Similarity	NPD9239	Approved
0.7361	Intermediate Similarity	NPD9440	Discontinued
0.7042	Intermediate Similarity	NPD9455	Approved
0.7015	Intermediate Similarity	NPD3215	Phase 1
0.6944	Remote Similarity	NPD393	Approved
0.686	Remote Similarity	NPD394	Phase 3
0.6716	Remote Similarity	NPD3214	Discontinued
0.6706	Remote Similarity	NPD883	Phase 2
0.6706	Remote Similarity	NPD882	Phase 2
0.6552	Remote Similarity	NPD9401	Discovery
0.6316	Remote Similarity	NPD3189	Approved
0.6316	Remote Similarity	NPD3190	Approved
0.6316	Remote Similarity	NPD3191	Approved
0.6282	Remote Similarity	NPD9031	Approved
0.6282	Remote Similarity	NPD8868	Approved
0.6282	Remote Similarity	NPD9030	Approved
0.6282	Remote Similarity	NPD9032	Approved
0.6282	Remote Similarity	NPD9033	Approved
0.6267	Remote Similarity	NPD9024	Phase 2
0.6267	Remote Similarity	NPD9022	Phase 2
0.6154	Remote Similarity	NPD2698	Approved
0.6122	Remote Similarity	NPD4837	Approved
0.6122	Remote Similarity	NPD4838	Approved
0.6122	Remote Similarity	NPD4835	Approved
0.6122	Remote Similarity	NPD4836	Approved
0.6024	Remote Similarity	NPD9034	Approved
0.6024	Remote Similarity	NPD67	Phase 2
0.6022	Remote Similarity	NPD5795	Approved
0.6022	Remote Similarity	NPD5794	Approved
0.6022	Remote Similarity	NPD5796	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5797	Approved
0.6022	Remote Similarity	NPD5798	Approved
0.5941	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4282	Approved
0.5882	Remote Similarity	NPD2700	Approved
0.587	Remote Similarity	NPD3200	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD2704	Phase 3
0.5854	Remote Similarity	NPD2702	Phase 1
0.5806	Remote Similarity	NPD3208	Approved
0.5806	Remote Similarity	NPD3202	Approved
0.5806	Remote Similarity	NPD3201	Approved
0.5806	Remote Similarity	NPD3203	Approved
0.5806	Remote Similarity	NPD3207	Approved
0.5806	Remote Similarity	NPD3209	Approved
0.5755	Remote Similarity	NPD4833	Approved
0.5755	Remote Similarity	NPD35	Approved
0.5755	Remote Similarity	NPD8087	Discontinued
0.5714	Remote Similarity	NPD3187	Discontinued
0.5714	Remote Similarity	NPD6704	Discontinued
0.5714	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD3182	Approved
0.5686	Remote Similarity	NPD3183	Approved
0.5686	Remote Similarity	NPD3185	Approved
0.5686	Remote Similarity	NPD3184	Approved
0.5673	Remote Similarity	NPD5376	Approved
0.5663	Remote Similarity	NPD9445	Approved
0.5647	Remote Similarity	NPD9653	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD3192	Approved
0.5641	Remote Similarity	NPD3193	Approved
0.5632	Remote Similarity	NPD372	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD1457	Discontinued
0.5625	Remote Similarity	NPD4261	Phase 1
0.5618	Remote Similarity	NPD9429	Discontinued
0.5612	Remote Similarity	NPD8394	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