NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	469.36
Volume:	514.112
LogP:	5.66
LogD:	5.143
LogS:	-4.32
# Rotatable Bonds:	1
TPSA:	66.4
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	4.831
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.441
MDCK Permeability:	9.842769941315055e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.809

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.141
Plasma Protein Binding (PPB):	98.21874237060547%
Volume Distribution (VD):	0.569
Pgp-substrate:	2.933835983276367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.886
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.885
CYP2C9-inhibitor:	0.171
CYP2C9-substrate:	0.246
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.541
CYP3A4-substrate:	0.503

ADMET: Excretion

Clearance (CL):	1.583
Half-life (T1/2):	0.161

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.348
Maximum Recommended Daily Dose:	0.224
Skin Sensitization:	0.049
Carcinogencity:	0.069
Eye Corrosion:	0.053
Eye Irritation:	0.03
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC477290

Natural Product ID:	NPC477290
*Common Name:**	4-aza-A-homo-3-oxo-ursolic acid
IUPAC Name:	(1R,2S,5S,8R,9S,10S,14R,15R,21R)-1,2,8,9,15,20,20-heptamethyl-18-oxo-19-azapentacyclo[12.9.0.02,11.05,10.015,21]tricos-11-ene-5-carboxylic acid
Synonyms:
Standard InCHIKey:	YRCGVDWNLBAYIE-OADIDDRXSA-N
Standard InCHI:	InChI=1S/C30H47NO3/c1-18-10-15-30(25(33)34)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(32)31-26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-22,24H,9-17H2,1-7H3,(H,31,32)(H,33,34)/t18-,19+,21+,22-,24+,27+,28-,29-,30+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CCC(=O)NC5(C)C)C)C)[C@@H]2[C@H]1C)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44562549
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000160] Lactams [CHEMONTID:0000163] Caprolactams

*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
NPO26571	Ilex paraguariensis	Species	Aquifoliaceae	Eukaryota	leaves	Mato Leitao, RS, Brazil	n.a.	PMID[18192087]
NPO26571	Ilex paraguariensis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25955847]
NPO26571	Ilex paraguariensis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26571	Ilex paraguariensis	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26571	Ilex paraguariensis	Species	Aquifoliaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	IC50	>	500000	nM	PMID[18192087]

☑ 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 NPC477290 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	96
0.1-0.2	831
0.2-0.3	7281
0.3-0.4	18190
0.4-0.5	8781
0.5-0.6	5981
0.6-0.7	1355
0.7-0.8	168
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8587	High Similarity	NPC474964
0.8587	High Similarity	NPC477288
0.8495	Intermediate Similarity	NPC476064
0.8161	Intermediate Similarity	NPC107039
0.8161	Intermediate Similarity	NPC471897
0.8161	Intermediate Similarity	NPC471899
0.8132	Intermediate Similarity	NPC477289
0.8068	Intermediate Similarity	NPC260385
0.8068	Intermediate Similarity	NPC280654
0.8068	Intermediate Similarity	NPC110094
0.8046	Intermediate Similarity	NPC89294
0.7978	Intermediate Similarity	NPC231431
0.7978	Intermediate Similarity	NPC199595
0.7978	Intermediate Similarity	NPC16394
0.7889	Intermediate Similarity	NPC37038
0.7889	Intermediate Similarity	NPC104545
0.7802	Intermediate Similarity	NPC162632
0.7802	Intermediate Similarity	NPC274050
0.7802	Intermediate Similarity	NPC471898
0.7802	Intermediate Similarity	NPC142244
0.7802	Intermediate Similarity	NPC221647
0.7802	Intermediate Similarity	NPC263272
0.7802	Intermediate Similarity	NPC267691
0.7742	Intermediate Similarity	NPC156981
0.7727	Intermediate Similarity	NPC192540
0.7727	Intermediate Similarity	NPC279666
0.7717	Intermediate Similarity	NPC251779
0.7717	Intermediate Similarity	NPC69101
0.7692	Intermediate Similarity	NPC477057
0.764	Intermediate Similarity	NPC69143
0.7634	Intermediate Similarity	NPC200752
0.7634	Intermediate Similarity	NPC70834
0.7614	Intermediate Similarity	NPC161923
0.7614	Intermediate Similarity	NPC241854
0.7614	Intermediate Similarity	NPC476046
0.7614	Intermediate Similarity	NPC103958
0.7614	Intermediate Similarity	NPC251970
0.7614	Intermediate Similarity	NPC183503
0.7614	Intermediate Similarity	NPC283908
0.7596	Intermediate Similarity	NPC119329
0.7586	Intermediate Similarity	NPC160817
0.7553	Intermediate Similarity	NPC96095
0.75	Intermediate Similarity	NPC36310
0.7474	Intermediate Similarity	NPC474537
0.7444	Intermediate Similarity	NPC309399
0.7419	Intermediate Similarity	NPC278459
0.7419	Intermediate Similarity	NPC147066
0.7416	Intermediate Similarity	NPC255168
0.7396	Intermediate Similarity	NPC324063
0.7363	Intermediate Similarity	NPC165711
0.7333	Intermediate Similarity	NPC476844
0.7333	Intermediate Similarity	NPC201027
0.732	Intermediate Similarity	NPC98442
0.732	Intermediate Similarity	NPC130577
0.732	Intermediate Similarity	NPC88716
0.732	Intermediate Similarity	NPC142415
0.732	Intermediate Similarity	NPC18064
0.732	Intermediate Similarity	NPC173089
0.732	Intermediate Similarity	NPC307426
0.732	Intermediate Similarity	NPC68160
0.732	Intermediate Similarity	NPC51700
0.732	Intermediate Similarity	NPC293564
0.732	Intermediate Similarity	NPC71507
0.732	Intermediate Similarity	NPC242468
0.732	Intermediate Similarity	NPC171203
0.732	Intermediate Similarity	NPC158141
0.732	Intermediate Similarity	NPC102683
0.7312	Intermediate Similarity	NPC267517
0.7283	Intermediate Similarity	NPC179028
0.7283	Intermediate Similarity	NPC321514
0.7263	Intermediate Similarity	NPC167103
0.7245	Intermediate Similarity	NPC181225
0.7245	Intermediate Similarity	NPC17733
0.7245	Intermediate Similarity	NPC1753
0.7245	Intermediate Similarity	NPC474512
0.7245	Intermediate Similarity	NPC246708
0.7245	Intermediate Similarity	NPC474474
0.7245	Intermediate Similarity	NPC474511
0.7245	Intermediate Similarity	NPC470629
0.7245	Intermediate Similarity	NPC473242
0.7245	Intermediate Similarity	NPC290690
0.7245	Intermediate Similarity	NPC52169
0.7245	Intermediate Similarity	NPC40552
0.7245	Intermediate Similarity	NPC182797
0.7234	Intermediate Similarity	NPC201912
0.7234	Intermediate Similarity	NPC38350
0.7234	Intermediate Similarity	NPC3915
0.7222	Intermediate Similarity	NPC301065
0.7222	Intermediate Similarity	NPC3753
0.7222	Intermediate Similarity	NPC237591
0.7222	Intermediate Similarity	NPC166797
0.7216	Intermediate Similarity	NPC72638
0.7204	Intermediate Similarity	NPC477371
0.7204	Intermediate Similarity	NPC158846
0.7204	Intermediate Similarity	NPC327674
0.7174	Intermediate Similarity	NPC68828
0.7172	Intermediate Similarity	NPC225585
0.7172	Intermediate Similarity	NPC130520
0.7172	Intermediate Similarity	NPC95246
0.7172	Intermediate Similarity	NPC127689
0.7172	Intermediate Similarity	NPC274330
0.7172	Intermediate Similarity	NPC474700
0.7172	Intermediate Similarity	NPC270768
0.7172	Intermediate Similarity	NPC161751
0.7172	Intermediate Similarity	NPC281524
0.7172	Intermediate Similarity	NPC474972
0.7172	Intermediate Similarity	NPC234346
0.7172	Intermediate Similarity	NPC293048
0.7172	Intermediate Similarity	NPC25906
0.7172	Intermediate Similarity	NPC59263
0.7172	Intermediate Similarity	NPC290972
0.7172	Intermediate Similarity	NPC64872
0.7172	Intermediate Similarity	NPC61543
0.7172	Intermediate Similarity	NPC198664
0.7172	Intermediate Similarity	NPC121798
0.7172	Intermediate Similarity	NPC470588
0.7172	Intermediate Similarity	NPC263393
0.7172	Intermediate Similarity	NPC477973
0.7172	Intermediate Similarity	NPC143232
0.7158	Intermediate Similarity	NPC320514
0.7158	Intermediate Similarity	NPC310989
0.7158	Intermediate Similarity	NPC260956
0.7143	Intermediate Similarity	NPC476795
0.7113	Intermediate Similarity	NPC29447
0.7111	Intermediate Similarity	NPC161187
0.7111	Intermediate Similarity	NPC330659
0.7111	Intermediate Similarity	NPC244708
0.71	Intermediate Similarity	NPC126369
0.71	Intermediate Similarity	NPC111110
0.71	Intermediate Similarity	NPC470589
0.71	Intermediate Similarity	NPC18872
0.71	Intermediate Similarity	NPC130278
0.71	Intermediate Similarity	NPC290614
0.71	Intermediate Similarity	NPC227467
0.71	Intermediate Similarity	NPC120840
0.71	Intermediate Similarity	NPC193750
0.71	Intermediate Similarity	NPC7260
0.71	Intermediate Similarity	NPC46441
0.71	Intermediate Similarity	NPC210037
0.71	Intermediate Similarity	NPC477872
0.71	Intermediate Similarity	NPC86372
0.71	Intermediate Similarity	NPC291028
0.71	Intermediate Similarity	NPC113989
0.71	Intermediate Similarity	NPC198818
0.71	Intermediate Similarity	NPC474728
0.71	Intermediate Similarity	NPC172361
0.71	Intermediate Similarity	NPC120968
0.71	Intermediate Similarity	NPC273621
0.7097	Intermediate Similarity	NPC239098
0.7083	Intermediate Similarity	NPC307258
0.7083	Intermediate Similarity	NPC69279
0.7083	Intermediate Similarity	NPC83569
0.7083	Intermediate Similarity	NPC215893
0.7083	Intermediate Similarity	NPC53733
0.7065	Intermediate Similarity	NPC246445
0.7065	Intermediate Similarity	NPC899
0.7065	Intermediate Similarity	NPC180886
0.7053	Intermediate Similarity	NPC477372
0.7053	Intermediate Similarity	NPC327002
0.7045	Intermediate Similarity	NPC36616
0.7045	Intermediate Similarity	NPC290445
0.7041	Intermediate Similarity	NPC325594
0.7041	Intermediate Similarity	NPC73038
0.7041	Intermediate Similarity	NPC155011
0.7037	Intermediate Similarity	NPC258130
0.703	Intermediate Similarity	NPC71074
0.703	Intermediate Similarity	NPC300351
0.703	Intermediate Similarity	NPC6255
0.703	Intermediate Similarity	NPC235884
0.703	Intermediate Similarity	NPC77099
0.703	Intermediate Similarity	NPC282616
0.703	Intermediate Similarity	NPC145067
0.703	Intermediate Similarity	NPC324341
0.703	Intermediate Similarity	NPC65120
0.703	Intermediate Similarity	NPC52021
0.703	Intermediate Similarity	NPC470590
0.703	Intermediate Similarity	NPC285184
0.703	Intermediate Similarity	NPC187722
0.703	Intermediate Similarity	NPC233455
0.703	Intermediate Similarity	NPC472149
0.703	Intermediate Similarity	NPC301244
0.703	Intermediate Similarity	NPC84319
0.703	Intermediate Similarity	NPC60755
0.703	Intermediate Similarity	NPC288833
0.703	Intermediate Similarity	NPC228784
0.703	Intermediate Similarity	NPC4036
0.703	Intermediate Similarity	NPC230064
0.703	Intermediate Similarity	NPC155120
0.703	Intermediate Similarity	NPC38754
0.703	Intermediate Similarity	NPC158030
0.703	Intermediate Similarity	NPC471588
0.703	Intermediate Similarity	NPC474525
0.703	Intermediate Similarity	NPC25299
0.703	Intermediate Similarity	NPC966
0.703	Intermediate Similarity	NPC105189
0.703	Intermediate Similarity	NPC306541
0.7021	Intermediate Similarity	NPC215843
0.7021	Intermediate Similarity	NPC192744
0.701	Intermediate Similarity	NPC171789
0.701	Intermediate Similarity	NPC248758

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 NPC477290 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	98
0.1-0.2	700
0.2-0.3	3415
0.3-0.4	3588
0.4-0.5	992
0.5-0.6	283
0.6-0.7	71
0.7-0.8	3
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
0.79	Intermediate Similarity	NPD6404	Discontinued
0.7087	Intermediate Similarity	NPD7614	Phase 1
0.703	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7748	Approved
0.6789	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6635	Remote Similarity	NPD6399	Phase 3
0.6633	Remote Similarity	NPD3667	Approved
0.6633	Remote Similarity	NPD4221	Approved
0.6633	Remote Similarity	NPD4223	Phase 3
0.6604	Remote Similarity	NPD7732	Phase 3
0.66	Remote Similarity	NPD5329	Approved
0.66	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4695	Discontinued
0.6571	Remote Similarity	NPD5771	Approved
0.6571	Remote Similarity	NPD5707	Approved
0.6535	Remote Similarity	NPD7521	Approved
0.6535	Remote Similarity	NPD5330	Approved
0.6535	Remote Similarity	NPD6684	Approved
0.6535	Remote Similarity	NPD7334	Approved
0.6535	Remote Similarity	NPD6409	Approved
0.6535	Remote Similarity	NPD6098	Approved
0.6535	Remote Similarity	NPD7146	Approved
0.65	Remote Similarity	NPD3133	Approved
0.65	Remote Similarity	NPD3666	Approved
0.65	Remote Similarity	NPD3665	Phase 1
0.65	Remote Similarity	NPD4197	Approved
0.6471	Remote Similarity	NPD3573	Approved
0.6449	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD3644	Approved
0.6435	Remote Similarity	NPD3643	Approved
0.6435	Remote Similarity	NPD3642	Approved
0.6415	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7900	Approved
0.6415	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5737	Approved
0.6408	Remote Similarity	NPD6672	Approved
0.6408	Remote Similarity	NPD4723	Approved
0.6408	Remote Similarity	NPD4722	Approved
0.6408	Remote Similarity	NPD6903	Approved
0.6392	Remote Similarity	NPD3617	Approved
0.6389	Remote Similarity	NPD6083	Phase 2
0.6389	Remote Similarity	NPD6084	Phase 2
0.6381	Remote Similarity	NPD5281	Approved
0.6381	Remote Similarity	NPD5284	Approved
0.6373	Remote Similarity	NPD4690	Approved
0.6373	Remote Similarity	NPD4688	Approved
0.6373	Remote Similarity	NPD5205	Approved
0.6373	Remote Similarity	NPD4693	Phase 3
0.6373	Remote Similarity	NPD4138	Approved
0.6373	Remote Similarity	NPD3618	Phase 1
0.6373	Remote Similarity	NPD4689	Approved
0.6373	Remote Similarity	NPD4519	Discontinued
0.6373	Remote Similarity	NPD4623	Approved
0.6364	Remote Similarity	NPD857	Phase 3
0.6346	Remote Similarity	NPD5328	Approved
0.6346	Remote Similarity	NPD6904	Approved
0.6346	Remote Similarity	NPD6673	Approved
0.6346	Remote Similarity	NPD6080	Approved
0.6286	Remote Similarity	NPD4096	Approved
0.6273	Remote Similarity	NPD8418	Phase 2
0.625	Remote Similarity	NPD5208	Approved
0.6226	Remote Similarity	NPD8035	Phase 2
0.6226	Remote Similarity	NPD6079	Approved
0.6226	Remote Similarity	NPD8034	Phase 2
0.6214	Remote Similarity	NPD5690	Phase 2
0.6214	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4694	Approved
0.6214	Remote Similarity	NPD5280	Approved
0.6207	Remote Similarity	NPD6420	Discontinued
0.6204	Remote Similarity	NPD5695	Phase 3
0.62	Remote Similarity	NPD8028	Phase 2
0.619	Remote Similarity	NPD4753	Phase 2
0.6186	Remote Similarity	NPD1346	Approved
0.6182	Remote Similarity	NPD5696	Approved
0.6176	Remote Similarity	NPD3668	Phase 3
0.6168	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7645	Phase 2
0.6139	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4243	Approved
0.6087	Remote Similarity	NPD4224	Phase 2
0.6078	Remote Similarity	NPD4788	Approved
0.6075	Remote Similarity	NPD5693	Phase 1
0.6075	Remote Similarity	NPD6411	Approved
0.6075	Remote Similarity	NPD6050	Approved
0.6068	Remote Similarity	NPD6421	Discontinued
0.6064	Remote Similarity	NPD4137	Phase 3
0.6064	Remote Similarity	NPD15	Approved
0.6064	Remote Similarity	NPD791	Approved
0.6061	Remote Similarity	NPD3732	Approved
0.6058	Remote Similarity	NPD5279	Phase 3
0.6055	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4692	Approved
0.604	Remote Similarity	NPD4139	Approved
0.6036	Remote Similarity	NPD7638	Approved
0.6019	Remote Similarity	NPD4202	Approved
0.6015	Remote Similarity	NPD6333	Approved
0.6015	Remote Similarity	NPD6334	Approved
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD4691	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD4747	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6939	Phase 2
0.6	Remote Similarity	NPD6402	Approved
0.5982	Remote Similarity	NPD7639	Approved
0.5982	Remote Similarity	NPD7640	Approved
0.5981	Remote Similarity	NPD790	Approved
0.5981	Remote Similarity	NPD5692	Phase 3
0.5981	Remote Similarity	NPD5207	Approved
0.5979	Remote Similarity	NPD4784	Approved
0.5979	Remote Similarity	NPD4785	Approved
0.5963	Remote Similarity	NPD6001	Approved
0.5957	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6081	Approved
0.5926	Remote Similarity	NPD5694	Approved
0.5918	Remote Similarity	NPD7339	Approved
0.5918	Remote Similarity	NPD6942	Approved
0.5909	Remote Similarity	NPD5210	Approved
0.5909	Remote Similarity	NPD4629	Approved
0.5897	Remote Similarity	NPD7320	Approved
0.5897	Remote Similarity	NPD6899	Approved
0.5897	Remote Similarity	NPD6881	Approved
0.5895	Remote Similarity	NPD1082	Approved
0.5888	Remote Similarity	NPD6101	Approved
0.5888	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5221	Approved
0.5856	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4697	Phase 3
0.5856	Remote Similarity	NPD5222	Approved
0.5847	Remote Similarity	NPD6372	Approved
0.5847	Remote Similarity	NPD6373	Approved
0.5846	Remote Similarity	NPD6914	Discontinued
0.584	Remote Similarity	NPD6909	Approved
0.584	Remote Similarity	NPD5981	Approved
0.584	Remote Similarity	NPD6908	Approved
0.5816	Remote Similarity	NPD5733	Approved
0.5816	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4058	Approved
0.5812	Remote Similarity	NPD6412	Phase 2
0.5812	Remote Similarity	NPD5697	Approved
0.5812	Remote Similarity	NPD5701	Approved
0.5804	Remote Similarity	NPD5173	Approved
0.5804	Remote Similarity	NPD4755	Approved
0.5798	Remote Similarity	NPD7290	Approved
0.5798	Remote Similarity	NPD6883	Approved
0.5798	Remote Similarity	NPD7102	Approved
0.5784	Remote Similarity	NPD7525	Registered
0.5769	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD6011	Approved
0.5758	Remote Similarity	NPD4190	Phase 3
0.5758	Remote Similarity	NPD5275	Approved
0.5758	Remote Similarity	NPD8039	Approved
0.575	Remote Similarity	NPD6847	Approved
0.575	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.575	Remote Similarity	NPD6650	Approved
0.575	Remote Similarity	NPD8130	Phase 1
0.575	Remote Similarity	NPD6869	Approved
0.575	Remote Similarity	NPD6649	Approved
0.575	Remote Similarity	NPD6617	Approved
0.575	Remote Similarity	NPD1719	Phase 1
0.5745	Remote Similarity	NPD7331	Phase 2
0.5727	Remote Similarity	NPD5133	Approved
0.5726	Remote Similarity	NPD1018	Approved
0.5726	Remote Similarity	NPD7333	Discontinued
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD6013	Approved
0.5702	Remote Similarity	NPD5286	Approved
0.5702	Remote Similarity	NPD4696	Approved
0.5702	Remote Similarity	NPD5285	Approved
0.5702	Remote Similarity	NPD4700	Approved
0.5702	Remote Similarity	NPD6882	Approved
0.5702	Remote Similarity	NPD8297	Approved
0.57	Remote Similarity	NPD6117	Approved
0.569	Remote Similarity	NPD6052	Approved
0.5688	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4687	Approved
0.5656	Remote Similarity	NPD8298	Phase 2
0.5652	Remote Similarity	NPD5223	Approved
0.5648	Remote Similarity	NPD4518	Approved
0.5645	Remote Similarity	NPD7115	Discovery
0.5644	Remote Similarity	NPD6116	Phase 1
0.5638	Remote Similarity	NPD7341	Phase 2
0.563	Remote Similarity	NPD6686	Approved
0.5625	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5360	Phase 3
0.5625	Remote Similarity	NPD7604	Phase 2
0.5625	Remote Similarity	NPD5654	Approved
0.5612	Remote Similarity	NPD5276	Approved
0.5603	Remote Similarity	NPD5211	Phase 2
0.5603	Remote Similarity	NPD5226	Approved
0.5603	Remote Similarity	NPD4633	Approved
0.5603	Remote Similarity	NPD5225	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