NPASS Compound

Structure

NPC148055 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 -0.8660 1.5000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 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 2 3 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 5 7 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 17 1 0 0 0 0 9 1 1 1 0 0 0 9 22 1 0 0 0 0 11 18 1 0 0 0 0 12 8 1 6 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 1 0 0 0 14 15 1 0 0 0 0 14 20 1 6 0 0 0 15 16 1 0 0 0 0 15 21 1 1 0 0 0 16 22 1 6 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.15
Volume:	321.802
LogP:	0.345
LogD:	0.443
LogS:	-1.301
# Rotatable Bonds:	6
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	3.681
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.43
MDCK Permeability:	3.2790860132081434e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.088
Human Intestinal Absorption (HIA):	0.839
20% Bioavailability (F20%):	0.428
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.171
Plasma Protein Binding (PPB):	67.81047821044922%
Volume Distribution (VD):	0.822
Pgp-substrate:	22.25113296508789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.057
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.551
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.766
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.299
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	3.656
Half-life (T1/2):	0.84

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.41
Rat Oral Acute Toxicity:	0.247
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.752
Carcinogencity:	0.114
Eye Corrosion:	0.004
Eye Irritation:	0.362
Respiratory Toxicity:	0.021

Download Data

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

Natural Product: NPC148055

Natural Product ID:	NPC148055
*Common Name:**	(-)-Rhododendrin
IUPAC Name:	(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(2R)-4-(4-hydroxyphenyl)butan-2-yl]oxyoxane-3,4,5-triol
Synonyms:	(-)-Rhododendrin
Standard InCHIKey:	KLLYDTMVSVIJEH-YYMOATHLSA-N
Standard InCHI:	InChI=1S/C16H24O7/c1-9(2-3-10-4-6-11(18)7-5-10)22-16-15(21)14(20)13(19)12(8-17)23-16/h4-7,9,12-21H,2-3,8H2,1H3/t9-,12-,13-,14+,15-,16-/m1/s1
SMILES:	C[C@H](CCc1ccc(cc1)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:	CHEMBL1086682
PubChem CID:	442538
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	floral spikes	n.a.	n.a.	PMID[17346076]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20363129]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[9873651]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4138	Betula platyphylla	Species	Betulaceae	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	6

Activity Type	# Activity
Cell Line	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	25.0	%	PMID[511328]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	42.3	%	PMID[511328]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	4.7	%	PMID[511327]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	10.1	%	PMID[511327]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	4.9	%	PMID[511327]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	-0.8	%	PMID[511327]

☑ 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 NPC148055 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	244
0.1-0.2	1172
0.2-0.3	3263
0.3-0.4	9613
0.4-0.5	9827
0.5-0.6	8896
0.6-0.7	7380
0.7-0.8	2069
0.8-0.85	159
0.85-0.9	56
0.9-0.95	14
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9815	High Similarity	NPC157338
0.9643	High Similarity	NPC469702
0.9643	High Similarity	NPC282409
0.9558	High Similarity	NPC476445
0.9558	High Similarity	NPC476448
0.9558	High Similarity	NPC469548
0.9474	High Similarity	NPC55608
0.9459	High Similarity	NPC175771
0.9455	High Similarity	NPC313193
0.9386	High Similarity	NPC469703
0.9386	High Similarity	NPC201402
0.9386	High Similarity	NPC160854
0.9386	High Similarity	NPC469704
0.9304	High Similarity	NPC469686
0.9224	High Similarity	NPC471067
0.9145	High Similarity	NPC178449
0.9145	High Similarity	NPC232454
0.9145	High Similarity	NPC470907
0.9138	High Similarity	NPC266045
0.906	High Similarity	NPC476142
0.8992	High Similarity	NPC90318
0.8983	High Similarity	NPC212176
0.8898	High Similarity	NPC52097
0.8889	High Similarity	NPC198734
0.8889	High Similarity	NPC469412
0.8889	High Similarity	NPC269242
0.8852	High Similarity	NPC469549
0.8843	High Similarity	NPC79715
0.8843	High Similarity	NPC264900
0.8843	High Similarity	NPC288416
0.8843	High Similarity	NPC469687
0.8843	High Similarity	NPC231607
0.8843	High Similarity	NPC108659
0.8814	High Similarity	NPC11724
0.8803	High Similarity	NPC469708
0.8803	High Similarity	NPC60589
0.8783	High Similarity	NPC301651
0.8783	High Similarity	NPC473556
0.877	High Similarity	NPC148982
0.876	High Similarity	NPC94179
0.876	High Similarity	NPC471157
0.8729	High Similarity	NPC476872
0.871	High Similarity	NPC235294
0.871	High Similarity	NPC248307
0.871	High Similarity	NPC65942
0.871	High Similarity	NPC46137
0.8699	High Similarity	NPC184092
0.8689	High Similarity	NPC156692
0.8689	High Similarity	NPC471882
0.8689	High Similarity	NPC173150
0.8689	High Similarity	NPC45224
0.8689	High Similarity	NPC471881
0.8689	High Similarity	NPC106677
0.8689	High Similarity	NPC35288
0.8678	High Similarity	NPC83218
0.8678	High Similarity	NPC126991
0.8629	High Similarity	NPC470122
0.8629	High Similarity	NPC17968
0.8629	High Similarity	NPC469705
0.8618	High Similarity	NPC158673
0.8607	High Similarity	NPC61181
0.8607	High Similarity	NPC252114
0.8595	High Similarity	NPC287429
0.856	High Similarity	NPC225384
0.856	High Similarity	NPC246869
0.856	High Similarity	NPC138777
0.856	High Similarity	NPC478255
0.8559	High Similarity	NPC477803
0.8548	High Similarity	NPC97326
0.8548	High Similarity	NPC307110
0.8548	High Similarity	NPC270849
0.8548	High Similarity	NPC26653
0.8537	High Similarity	NPC103533
0.8525	High Similarity	NPC123704
0.8504	High Similarity	NPC470881
0.8504	High Similarity	NPC35731
0.8504	High Similarity	NPC169398
0.85	High Similarity	NPC226712
0.8492	Intermediate Similarity	NPC471095
0.8492	Intermediate Similarity	NPC471066
0.8492	Intermediate Similarity	NPC254275
0.848	Intermediate Similarity	NPC472024
0.848	Intermediate Similarity	NPC80600
0.8468	Intermediate Similarity	NPC37714
0.8468	Intermediate Similarity	NPC225307
0.8468	Intermediate Similarity	NPC152384
0.8438	Intermediate Similarity	NPC263829
0.8435	Intermediate Similarity	NPC42911
0.8435	Intermediate Similarity	NPC290353
0.8435	Intermediate Similarity	NPC153795
0.8426	Intermediate Similarity	NPC262826
0.8425	Intermediate Similarity	NPC6836
0.8425	Intermediate Similarity	NPC164172
0.8421	Intermediate Similarity	NPC30563
0.8413	Intermediate Similarity	NPC475824
0.8413	Intermediate Similarity	NPC281798
0.8413	Intermediate Similarity	NPC476407
0.84	Intermediate Similarity	NPC477293
0.84	Intermediate Similarity	NPC253595
0.84	Intermediate Similarity	NPC229784
0.84	Intermediate Similarity	NPC166040
0.84	Intermediate Similarity	NPC248355
0.84	Intermediate Similarity	NPC477294
0.8387	Intermediate Similarity	NPC198798
0.8374	Intermediate Similarity	NPC470510
0.8372	Intermediate Similarity	NPC52277
0.8372	Intermediate Similarity	NPC177035
0.8372	Intermediate Similarity	NPC199459
0.8359	Intermediate Similarity	NPC287597
0.8359	Intermediate Similarity	NPC107478
0.8359	Intermediate Similarity	NPC886
0.8359	Intermediate Similarity	NPC34293
0.8346	Intermediate Similarity	NPC473285
0.8346	Intermediate Similarity	NPC252833
0.8333	Intermediate Similarity	NPC276061
0.8333	Intermediate Similarity	NPC262606
0.8333	Intermediate Similarity	NPC474148
0.832	Intermediate Similarity	NPC232880
0.832	Intermediate Similarity	NPC302378
0.8308	Intermediate Similarity	NPC304152
0.8308	Intermediate Similarity	NPC65262
0.8308	Intermediate Similarity	NPC262328
0.8308	Intermediate Similarity	NPC87777
0.8308	Intermediate Similarity	NPC469364
0.8308	Intermediate Similarity	NPC470413
0.8308	Intermediate Similarity	NPC101686
0.8308	Intermediate Similarity	NPC138738
0.8295	Intermediate Similarity	NPC79957
0.8295	Intermediate Similarity	NPC123988
0.8281	Intermediate Similarity	NPC294166
0.8281	Intermediate Similarity	NPC115022
0.8281	Intermediate Similarity	NPC132895
0.8281	Intermediate Similarity	NPC25821
0.8281	Intermediate Similarity	NPC114116
0.8281	Intermediate Similarity	NPC254398
0.8268	Intermediate Similarity	NPC219677
0.8268	Intermediate Similarity	NPC254819
0.8268	Intermediate Similarity	NPC9912
0.8268	Intermediate Similarity	NPC121376
0.8268	Intermediate Similarity	NPC475067
0.8261	Intermediate Similarity	NPC63345
0.8261	Intermediate Similarity	NPC264784
0.8254	Intermediate Similarity	NPC295970
0.8244	Intermediate Similarity	NPC476383
0.8244	Intermediate Similarity	NPC64141
0.8244	Intermediate Similarity	NPC68092
0.8244	Intermediate Similarity	NPC89105
0.8244	Intermediate Similarity	NPC472350
0.8244	Intermediate Similarity	NPC197316
0.8244	Intermediate Similarity	NPC81515
0.8241	Intermediate Similarity	NPC313650
0.824	Intermediate Similarity	NPC476873
0.8235	Intermediate Similarity	NPC476266
0.8231	Intermediate Similarity	NPC471345
0.823	Intermediate Similarity	NPC135464
0.823	Intermediate Similarity	NPC92623
0.8226	Intermediate Similarity	NPC12308
0.8217	Intermediate Similarity	NPC48863
0.8217	Intermediate Similarity	NPC471883
0.8217	Intermediate Similarity	NPC13745
0.8217	Intermediate Similarity	NPC251981
0.8217	Intermediate Similarity	NPC187194
0.8214	Intermediate Similarity	NPC47286
0.8203	Intermediate Similarity	NPC26080
0.8203	Intermediate Similarity	NPC85799
0.8203	Intermediate Similarity	NPC473924
0.8203	Intermediate Similarity	NPC165686
0.8203	Intermediate Similarity	NPC470270
0.8203	Intermediate Similarity	NPC303422
0.8198	Intermediate Similarity	NPC91461
0.8198	Intermediate Similarity	NPC7686
0.8198	Intermediate Similarity	NPC40258
0.8189	Intermediate Similarity	NPC474491
0.8175	Intermediate Similarity	NPC40377
0.8168	Intermediate Similarity	NPC84789
0.8168	Intermediate Similarity	NPC302583
0.8168	Intermediate Similarity	NPC78363
0.8168	Intermediate Similarity	NPC260425
0.8168	Intermediate Similarity	NPC469696
0.8168	Intermediate Similarity	NPC310252
0.8168	Intermediate Similarity	NPC476376
0.8168	Intermediate Similarity	NPC100558
0.8154	Intermediate Similarity	NPC103398
0.8154	Intermediate Similarity	NPC158325
0.8154	Intermediate Similarity	NPC101624
0.8154	Intermediate Similarity	NPC180171
0.8154	Intermediate Similarity	NPC238243
0.8154	Intermediate Similarity	NPC184938
0.8142	Intermediate Similarity	NPC233396
0.8142	Intermediate Similarity	NPC154899
0.814	Intermediate Similarity	NPC28637
0.814	Intermediate Similarity	NPC215833
0.814	Intermediate Similarity	NPC69513
0.814	Intermediate Similarity	NPC49074
0.8136	Intermediate Similarity	NPC473137
0.8136	Intermediate Similarity	NPC12656
0.812	Intermediate Similarity	NPC134405
0.812	Intermediate Similarity	NPC210192
0.812	Intermediate Similarity	NPC476377
0.812	Intermediate Similarity	NPC472711

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 NPC148055 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	758
0.2-0.3	1520
0.3-0.4	3033
0.4-0.5	1934
0.5-0.6	1217
0.6-0.7	432
0.7-0.8	37
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
0.85	High Similarity	NPD1091	Approved
0.8244	Intermediate Similarity	NPD7266	Discontinued
0.7818	Intermediate Similarity	NPD2934	Approved
0.7818	Intermediate Similarity	NPD2933	Approved
0.7748	Intermediate Similarity	NPD2859	Approved
0.7748	Intermediate Similarity	NPD2860	Approved
0.7692	Intermediate Similarity	NPD3027	Phase 3
0.7627	Intermediate Similarity	NPD2684	Approved
0.76	Intermediate Similarity	NPD5126	Approved
0.76	Intermediate Similarity	NPD5125	Phase 3
0.7565	Intermediate Similarity	NPD940	Approved
0.7565	Intermediate Similarity	NPD846	Approved
0.7544	Intermediate Similarity	NPD3020	Approved
0.7521	Intermediate Similarity	NPD7843	Approved
0.748	Intermediate Similarity	NPD3705	Approved
0.7429	Intermediate Similarity	NPD5058	Phase 3
0.7417	Intermediate Similarity	NPD3022	Approved
0.7417	Intermediate Similarity	NPD3021	Approved
0.7395	Intermediate Similarity	NPD290	Approved
0.7388	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1613	Approved
0.7385	Intermediate Similarity	NPD3094	Phase 2
0.7381	Intermediate Similarity	NPD1357	Approved
0.7353	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7157	Approved
0.7323	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD111	Approved
0.7292	Intermediate Similarity	NPD1653	Approved
0.7273	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4538	Approved
0.7226	Intermediate Similarity	NPD4536	Approved
0.7226	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD4908	Phase 1
0.7214	Intermediate Similarity	NPD6674	Discontinued
0.7209	Intermediate Similarity	NPD3092	Approved
0.7179	Intermediate Similarity	NPD1242	Phase 1
0.7165	Intermediate Similarity	NPD1548	Phase 1
0.7154	Intermediate Similarity	NPD228	Approved
0.7154	Intermediate Similarity	NPD969	Suspended
0.7143	Intermediate Similarity	NPD2861	Phase 2
0.7133	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4659	Approved
0.7099	Intermediate Similarity	NPD3685	Discontinued
0.7092	Intermediate Similarity	NPD1652	Phase 2
0.709	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD856	Approved
0.7087	Intermediate Similarity	NPD16	Approved
0.7077	Intermediate Similarity	NPD1610	Phase 2
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7054	Intermediate Similarity	NPD9384	Approved
0.7054	Intermediate Similarity	NPD9381	Approved
0.705	Intermediate Similarity	NPD5960	Phase 3
0.705	Intermediate Similarity	NPD5588	Approved
0.7047	Intermediate Similarity	NPD8455	Phase 2
0.7045	Intermediate Similarity	NPD8651	Approved
0.7034	Intermediate Similarity	NPD3028	Approved
0.7031	Intermediate Similarity	NPD9545	Approved
0.7031	Intermediate Similarity	NPD3091	Approved
0.7025	Intermediate Similarity	NPD968	Approved
0.7023	Intermediate Similarity	NPD2562	Approved
0.7023	Intermediate Similarity	NPD2561	Approved
0.7015	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6190	Approved
0.6992	Remote Similarity	NPD4750	Phase 3
0.6992	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4103	Phase 2
0.6983	Remote Similarity	NPD1809	Phase 2
0.6983	Remote Similarity	NPD844	Approved
0.6978	Remote Similarity	NPD7097	Phase 1
0.6972	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.697	Remote Similarity	NPD9622	Approved
0.6967	Remote Similarity	NPD1358	Approved
0.6957	Remote Similarity	NPD845	Approved
0.6953	Remote Similarity	NPD318	Approved
0.6953	Remote Similarity	NPD317	Approved
0.6947	Remote Similarity	NPD422	Phase 1
0.6934	Remote Similarity	NPD6407	Approved
0.6934	Remote Similarity	NPD6405	Approved
0.6929	Remote Similarity	NPD6671	Approved
0.6923	Remote Similarity	NPD4628	Phase 3
0.6923	Remote Similarity	NPD5846	Approved
0.6923	Remote Similarity	NPD6516	Phase 2
0.6912	Remote Similarity	NPD3179	Approved
0.6912	Remote Similarity	NPD3180	Approved
0.6905	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4060	Phase 1
0.6884	Remote Similarity	NPD3062	Approved
0.6884	Remote Similarity	NPD3059	Approved
0.6884	Remote Similarity	NPD3061	Approved
0.688	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6798	Discontinued
0.6861	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5124	Phase 1
0.6835	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7054	Approved
0.6835	Remote Similarity	NPD4340	Discontinued
0.6831	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD821	Approved
0.6821	Remote Similarity	NPD2978	Approved
0.6821	Remote Similarity	NPD2977	Approved
0.6815	Remote Similarity	NPD9619	Approved
0.6815	Remote Similarity	NPD9620	Approved
0.6815	Remote Similarity	NPD9621	Approved
0.6812	Remote Similarity	NPD4062	Phase 3
0.6809	Remote Similarity	NPD4108	Discontinued
0.68	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3095	Discontinued
0.6792	Remote Similarity	NPD7074	Phase 3
0.6792	Remote Similarity	NPD7472	Approved
0.6786	Remote Similarity	NPD5314	Approved
0.6786	Remote Similarity	NPD6653	Approved
0.6786	Remote Similarity	NPD2568	Approved
0.6783	Remote Similarity	NPD2424	Discontinued
0.6781	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.678	Remote Similarity	NPD288	Approved
0.6772	Remote Similarity	NPD2228	Approved
0.6772	Remote Similarity	NPD2234	Approved
0.6772	Remote Similarity	NPD7228	Approved
0.6772	Remote Similarity	NPD2229	Approved
0.6772	Remote Similarity	NPD5283	Phase 1
0.6765	Remote Similarity	NPD5736	Approved
0.6755	Remote Similarity	NPD37	Approved
0.6753	Remote Similarity	NPD6234	Discontinued
0.675	Remote Similarity	NPD6797	Phase 2
0.6748	Remote Similarity	NPD3134	Approved
0.6741	Remote Similarity	NPD1135	Approved
0.6741	Remote Similarity	NPD1131	Approved
0.6741	Remote Similarity	NPD1133	Approved
0.6741	Remote Similarity	NPD1134	Approved
0.6741	Remote Similarity	NPD1129	Approved
0.6739	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD598	Approved
0.6739	Remote Similarity	NPD601	Approved
0.6739	Remote Similarity	NPD597	Approved
0.6735	Remote Similarity	NPD3536	Discontinued
0.6733	Remote Similarity	NPD4380	Phase 2
0.6732	Remote Similarity	NPD4965	Approved
0.6732	Remote Similarity	NPD4966	Approved
0.6732	Remote Similarity	NPD4967	Phase 2
0.6721	Remote Similarity	NPD9610	Approved
0.6721	Remote Similarity	NPD9608	Approved
0.6719	Remote Similarity	NPD2629	Approved
0.6719	Remote Similarity	NPD9614	Approved
0.6719	Remote Similarity	NPD9618	Approved
0.6716	Remote Similarity	NPD6582	Phase 2
0.6716	Remote Similarity	NPD6583	Phase 3
0.6716	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD4749	Approved
0.6714	Remote Similarity	NPD230	Phase 1
0.6714	Remote Similarity	NPD6355	Discontinued
0.6708	Remote Similarity	NPD6559	Discontinued
0.6708	Remote Similarity	NPD7251	Discontinued
0.6694	Remote Similarity	NPD9532	Phase 3
0.6694	Remote Similarity	NPD291	Approved
0.6693	Remote Similarity	NPD5535	Approved
0.6692	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1136	Approved
0.6691	Remote Similarity	NPD1130	Approved
0.6691	Remote Similarity	NPD1132	Approved
0.669	Remote Similarity	NPD4535	Phase 3
0.669	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD823	Approved
0.6667	Remote Similarity	NPD5048	Discontinued
0.6667	Remote Similarity	NPD817	Approved
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD3052	Approved
0.6667	Remote Similarity	NPD7808	Phase 3
0.6667	Remote Similarity	NPD3054	Approved
0.6644	Remote Similarity	NPD2677	Approved
0.6643	Remote Similarity	NPD3620	Phase 2
0.6643	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2238	Phase 2
0.6642	Remote Similarity	NPD2231	Phase 2
0.6642	Remote Similarity	NPD2235	Phase 2
0.6641	Remote Similarity	NPD7741	Discontinued
0.6621	Remote Similarity	NPD3060	Approved
0.6621	Remote Similarity	NPD4236	Phase 3
0.6621	Remote Similarity	NPD4237	Approved
0.6618	Remote Similarity	NPD1817	Approved
0.6618	Remote Similarity	NPD1820	Approved
0.6618	Remote Similarity	NPD1818	Approved
0.6618	Remote Similarity	NPD1819	Approved
0.6617	Remote Similarity	NPD3496	Discontinued
0.6617	Remote Similarity	NPD3847	Discontinued
0.6615	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7685	Pre-registration
0.6597	Remote Similarity	NPD5763	Approved
0.6597	Remote Similarity	NPD1375	Discontinued
0.6597	Remote Similarity	NPD5762	Approved
0.6596	Remote Similarity	NPD5735	Approved
0.6593	Remote Similarity	NPD2983	Phase 2
0.6593	Remote Similarity	NPD2982	Phase 2
0.6593	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD556	Approved
0.6587	Remote Similarity	NPD5451	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