NPASS Compound

Structure

NPC476233 OpenBabel07101718182D 23 27 0 0 1 0 0 0 0 0999 V2000 -4.3779 -2.1184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2103 0.8106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2932 1.6698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4723 -0.1706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1953 1.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6930 0.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4831 -0.8906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8434 0.1801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6179 -1.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3780 -2.1334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4781 1.3309 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5963 0.1614 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2360 -0.9093 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9889 -0.9279 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8650 -1.2599 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2252 -0.1893 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9781 -0.2079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3781 -2.1483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1305 -1.4408 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 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 11 17 1 0 0 0 0 11 21 1 0 0 0 0 12 19 1 1 0 0 0 13 18 1 6 0 0 0 13 20 1 0 0 0 0 14 17 1 1 0 0 0 14 18 1 0 0 0 0 15 20 1 1 0 0 0 15 22 1 0 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 16 23 1 0 0 0 0 17 1 1 6 0 0 0 18 2 1 6 0 0 0 19 3 1 1 0 0 0 19 23 1 0 0 0 0 20 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	338.065
LogP:	2.666
LogD:	2.805
LogS:	-4.315
# Rotatable Bonds:	1
TPSA:	52.99
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	6.216
Fsp3:	1.0
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:	-4.835
MDCK Permeability:	3.096461659879424e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.79

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.47
Plasma Protein Binding (PPB):	81.49044036865234%
Volume Distribution (VD):	1.191
Pgp-substrate:	16.518136978149414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.544
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.222
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.31

ADMET: Excretion

Clearance (CL):	7.555
Half-life (T1/2):	0.556

ADMET: Toxicity

hERG Blockers:	0.161
Human Hepatotoxicity (H-HT):	0.802
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.936
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.907
Carcinogencity:	0.085
Eye Corrosion:	0.723
Eye Irritation:	0.48
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: NPC476233

Natural Product ID:	NPC476233
*Common Name:**	Sideroxol
IUPAC Name:	n.a.
Synonyms:	Sideroxol
Standard InCHIKey:	BDWKHKXSYDEDRO-PVACTHOZSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-17(11-21)7-4-8-18(2)13-6-5-12-10-20(13,15(22)9-14(17)18)16-19(12,3)23-16/h12-16,21-22H,4-11H2,1-3H3/t12-,13+,14+,15+,16+,17-,18+,19+,20-/m1/s1
SMILES:	OC[C@@]1(C)CCC[C@@]2([C@H]1C[C@H](O)[C@]13[C@H]2CC[C@H](C1)[C@]1([C@@H]3O1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL556939
PubChem CID:	45269664
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO6139	Sideritis arguta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19215141]
NPO6139	Sideritis arguta	Species	Lamiaceae	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	5
Others	2

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	2
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	14500.0	nM	PMID[529943]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	=	25000.0	nM	PMID[529943]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	200000.0	nM	PMID[529943]
NPT1	Others	Radical scavenging activity		IC50	>	200000.0	nM	PMID[529943]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	AFI	=	9.0	%	PMID[529944]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	AFI	=	54.0	%	PMID[529944]

☑ 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 NPC476233 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	446
0.1-0.2	4663
0.2-0.3	14993
0.3-0.4	9664
0.4-0.5	5020
0.5-0.6	4852
0.6-0.7	2305
0.7-0.8	615
0.8-0.85	87
0.85-0.9	47
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9324	High Similarity	NPC471769
0.9079	High Similarity	NPC16449
0.9054	High Similarity	NPC470145
0.9041	High Similarity	NPC304499
0.9028	High Similarity	NPC1340
0.9028	High Similarity	NPC470071
0.9028	High Similarity	NPC187471
0.9028	High Similarity	NPC252182
0.9014	High Similarity	NPC477820
0.8919	High Similarity	NPC317242
0.8889	High Similarity	NPC232925
0.8889	High Similarity	NPC63588
0.8889	High Similarity	NPC251201
0.8846	High Similarity	NPC475388
0.88	High Similarity	NPC163597
0.8784	High Similarity	NPC475458
0.8767	High Similarity	NPC195530
0.875	High Similarity	NPC66407
0.8701	High Similarity	NPC287452
0.8701	High Similarity	NPC476176
0.8684	High Similarity	NPC477227
0.8684	High Similarity	NPC185915
0.8684	High Similarity	NPC128951
0.8684	High Similarity	NPC192046
0.8684	High Similarity	NPC302578
0.8684	High Similarity	NPC105208
0.8649	High Similarity	NPC470610
0.8649	High Similarity	NPC153719
0.863	High Similarity	NPC282454
0.8625	High Similarity	NPC86238
0.8611	High Similarity	NPC474756
0.8592	High Similarity	NPC44122
0.8571	High Similarity	NPC471045
0.8571	High Similarity	NPC67657
0.8571	High Similarity	NPC18857
0.8533	High Similarity	NPC228994
0.8533	High Similarity	NPC477508
0.8533	High Similarity	NPC48795
0.8533	High Similarity	NPC192501
0.8533	High Similarity	NPC10476
0.8519	High Similarity	NPC266651
0.8514	High Similarity	NPC100586
0.8514	High Similarity	NPC127094
0.8514	High Similarity	NPC473279
0.8514	High Similarity	NPC109457
0.8514	High Similarity	NPC157422
0.8493	Intermediate Similarity	NPC254037
0.8493	Intermediate Similarity	NPC129829
0.8472	Intermediate Similarity	NPC475884
0.8472	Intermediate Similarity	NPC473230
0.8462	Intermediate Similarity	NPC81074
0.8462	Intermediate Similarity	NPC477282
0.8442	Intermediate Similarity	NPC64081
0.8442	Intermediate Similarity	NPC11907
0.8442	Intermediate Similarity	NPC133596
0.8442	Intermediate Similarity	NPC474574
0.8421	Intermediate Similarity	NPC472950
0.8421	Intermediate Similarity	NPC243027
0.8421	Intermediate Similarity	NPC196136
0.8421	Intermediate Similarity	NPC158208
0.8421	Intermediate Similarity	NPC472952
0.8421	Intermediate Similarity	NPC270306
0.8421	Intermediate Similarity	NPC91387
0.8421	Intermediate Similarity	NPC231680
0.8378	Intermediate Similarity	NPC192192
0.8375	Intermediate Similarity	NPC470611
0.8375	Intermediate Similarity	NPC296734
0.8356	Intermediate Similarity	NPC472741
0.8354	Intermediate Similarity	NPC248944
0.8354	Intermediate Similarity	NPC66766
0.8354	Intermediate Similarity	NPC7479
0.8354	Intermediate Similarity	NPC117137
0.8354	Intermediate Similarity	NPC474714
0.8354	Intermediate Similarity	NPC257296
0.8353	Intermediate Similarity	NPC59006
0.8333	Intermediate Similarity	NPC147993
0.8313	Intermediate Similarity	NPC210658
0.8313	Intermediate Similarity	NPC161928
0.831	Intermediate Similarity	NPC118937
0.831	Intermediate Similarity	NPC167995
0.831	Intermediate Similarity	NPC281540
0.831	Intermediate Similarity	NPC159654
0.8267	Intermediate Similarity	NPC8004
0.8267	Intermediate Similarity	NPC127283
0.825	Intermediate Similarity	NPC73515
0.825	Intermediate Similarity	NPC473257
0.8243	Intermediate Similarity	NPC107919
0.8243	Intermediate Similarity	NPC241085
0.8243	Intermediate Similarity	NPC299948
0.8243	Intermediate Similarity	NPC470830
0.8228	Intermediate Similarity	NPC269333
0.8219	Intermediate Similarity	NPC48079
0.8219	Intermediate Similarity	NPC63190
0.8214	Intermediate Similarity	NPC128475
0.8194	Intermediate Similarity	NPC473276
0.8194	Intermediate Similarity	NPC474380
0.8194	Intermediate Similarity	NPC41577
0.8193	Intermediate Similarity	NPC471240
0.8182	Intermediate Similarity	NPC186851
0.8171	Intermediate Similarity	NPC320824
0.8169	Intermediate Similarity	NPC249078
0.8169	Intermediate Similarity	NPC114891
0.8169	Intermediate Similarity	NPC236099
0.8169	Intermediate Similarity	NPC209686
0.8161	Intermediate Similarity	NPC30687
0.8158	Intermediate Similarity	NPC473238
0.8158	Intermediate Similarity	NPC472341
0.8148	Intermediate Similarity	NPC154043
0.8148	Intermediate Similarity	NPC60018
0.8148	Intermediate Similarity	NPC202688
0.814	Intermediate Similarity	NPC473066
0.8118	Intermediate Similarity	NPC228059
0.8101	Intermediate Similarity	NPC477819
0.8101	Intermediate Similarity	NPC477817
0.8095	Intermediate Similarity	NPC5943
0.8082	Intermediate Similarity	NPC142712
0.8072	Intermediate Similarity	NPC273290
0.8072	Intermediate Similarity	NPC232044
0.8072	Intermediate Similarity	NPC290612
0.8056	Intermediate Similarity	NPC69149
0.8049	Intermediate Similarity	NPC478054
0.8049	Intermediate Similarity	NPC232023
0.8028	Intermediate Similarity	NPC71460
0.8028	Intermediate Similarity	NPC148174
0.8028	Intermediate Similarity	NPC218585
0.8026	Intermediate Similarity	NPC131506
0.8026	Intermediate Similarity	NPC157777
0.8025	Intermediate Similarity	NPC469745
0.8023	Intermediate Similarity	NPC10274
0.8023	Intermediate Similarity	NPC279329
0.8	Intermediate Similarity	NPC220379
0.8	Intermediate Similarity	NPC281004
0.8	Intermediate Similarity	NPC470833
0.7976	Intermediate Similarity	NPC131365
0.7976	Intermediate Similarity	NPC215968
0.7976	Intermediate Similarity	NPC155531
0.7975	Intermediate Similarity	NPC212453
0.7955	Intermediate Similarity	NPC175
0.7952	Intermediate Similarity	NPC227260
0.7952	Intermediate Similarity	NPC474156
0.7945	Intermediate Similarity	NPC475943
0.7945	Intermediate Similarity	NPC190827
0.7945	Intermediate Similarity	NPC243469
0.7931	Intermediate Similarity	NPC36372
0.7931	Intermediate Similarity	NPC293609
0.7922	Intermediate Similarity	NPC253805
0.7907	Intermediate Similarity	NPC102725
0.7907	Intermediate Similarity	NPC20822
0.7907	Intermediate Similarity	NPC473472
0.7901	Intermediate Similarity	NPC472943
0.7901	Intermediate Similarity	NPC472951
0.7901	Intermediate Similarity	NPC71535
0.7901	Intermediate Similarity	NPC78545
0.7895	Intermediate Similarity	NPC231945
0.7882	Intermediate Similarity	NPC202937
0.7882	Intermediate Similarity	NPC43912
0.7882	Intermediate Similarity	NPC140446
0.7875	Intermediate Similarity	NPC31828
0.7865	Intermediate Similarity	NPC473065
0.7865	Intermediate Similarity	NPC473064
0.7865	Intermediate Similarity	NPC473067
0.7841	Intermediate Similarity	NPC167644
0.7841	Intermediate Similarity	NPC256104
0.7841	Intermediate Similarity	NPC473726
0.7841	Intermediate Similarity	NPC277774
0.7841	Intermediate Similarity	NPC182740
0.7841	Intermediate Similarity	NPC122083
0.7841	Intermediate Similarity	NPC211845
0.7841	Intermediate Similarity	NPC311246
0.7831	Intermediate Similarity	NPC111582
0.7831	Intermediate Similarity	NPC477285
0.7831	Intermediate Similarity	NPC470070
0.7821	Intermediate Similarity	NPC478130
0.7816	Intermediate Similarity	NPC473542
0.7816	Intermediate Similarity	NPC65550
0.7816	Intermediate Similarity	NPC77756
0.7816	Intermediate Similarity	NPC223143
0.7792	Intermediate Similarity	NPC478103
0.7791	Intermediate Similarity	NPC226491
0.7791	Intermediate Similarity	NPC477614
0.7791	Intermediate Similarity	NPC473436
0.7778	Intermediate Similarity	NPC95804
0.7778	Intermediate Similarity	NPC476510
0.7778	Intermediate Similarity	NPC156377
0.7778	Intermediate Similarity	NPC185547
0.7778	Intermediate Similarity	NPC142264
0.7778	Intermediate Similarity	NPC24504
0.7778	Intermediate Similarity	NPC476316
0.7765	Intermediate Similarity	NPC477283
0.7765	Intermediate Similarity	NPC201273
0.7765	Intermediate Similarity	NPC6605
0.7765	Intermediate Similarity	NPC121981
0.7753	Intermediate Similarity	NPC45959
0.7753	Intermediate Similarity	NPC477224
0.7753	Intermediate Similarity	NPC473503
0.7753	Intermediate Similarity	NPC252253
0.7753	Intermediate Similarity	NPC113500
0.7753	Intermediate Similarity	NPC3538
0.7753	Intermediate Similarity	NPC309866
0.775	Intermediate Similarity	NPC171658

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 NPC476233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	458
0.1-0.2	4437
0.2-0.3	3007
0.3-0.4	703
0.4-0.5	224
0.5-0.6	233
0.6-0.7	66
0.7-0.8	20
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
0.8354	Intermediate Similarity	NPD6928	Phase 2
0.8243	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD4787	Phase 1
0.7444	Intermediate Similarity	NPD8171	Discontinued
0.7439	Intermediate Similarity	NPD6697	Approved
0.7439	Intermediate Similarity	NPD6115	Approved
0.7439	Intermediate Similarity	NPD6118	Approved
0.7439	Intermediate Similarity	NPD6114	Approved
0.7342	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6116	Phase 1
0.7284	Intermediate Similarity	NPD3703	Phase 2
0.7262	Intermediate Similarity	NPD7525	Registered
0.7215	Intermediate Similarity	NPD4245	Approved
0.7215	Intermediate Similarity	NPD4244	Approved
0.7195	Intermediate Similarity	NPD6117	Approved
0.716	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3698	Phase 2
0.7089	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5360	Phase 3
0.6915	Remote Similarity	NPD7991	Discontinued
0.6883	Remote Similarity	NPD371	Approved
0.6867	Remote Similarity	NPD3702	Approved
0.679	Remote Similarity	NPD4789	Approved
0.6707	Remote Similarity	NPD5777	Approved
0.67	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4748	Discontinued
0.6593	Remote Similarity	NPD8308	Discontinued
0.6588	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7645	Phase 2
0.6531	Remote Similarity	NPD7638	Approved
0.6522	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4758	Discontinued
0.6489	Remote Similarity	NPD6700	Approved
0.6489	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7339	Approved
0.6471	Remote Similarity	NPD6942	Approved
0.6465	Remote Similarity	NPD7639	Approved
0.6465	Remote Similarity	NPD7640	Approved
0.6444	Remote Similarity	NPD4788	Approved
0.6444	Remote Similarity	NPD6695	Phase 3
0.6437	Remote Similarity	NPD3671	Phase 1
0.6421	Remote Similarity	NPD8035	Phase 2
0.6421	Remote Similarity	NPD6703	Approved
0.6421	Remote Similarity	NPD8034	Phase 2
0.6421	Remote Similarity	NPD6702	Approved
0.64	Remote Similarity	NPD1700	Approved
0.64	Remote Similarity	NPD4159	Approved
0.6354	Remote Similarity	NPD4202	Approved
0.6353	Remote Similarity	NPD1810	Approved
0.6353	Remote Similarity	NPD1811	Approved
0.6341	Remote Similarity	NPD6705	Phase 1
0.6337	Remote Similarity	NPD7632	Discontinued
0.6311	Remote Similarity	NPD6675	Approved
0.6311	Remote Similarity	NPD6402	Approved
0.6311	Remote Similarity	NPD5739	Approved
0.6311	Remote Similarity	NPD7128	Approved
0.631	Remote Similarity	NPD4243	Approved
0.6292	Remote Similarity	NPD6931	Approved
0.6292	Remote Similarity	NPD6930	Phase 2
0.6273	Remote Similarity	NPD7328	Approved
0.6273	Remote Similarity	NPD7327	Approved
0.6263	Remote Similarity	NPD4755	Approved
0.625	Remote Similarity	NPD5364	Discontinued
0.6216	Remote Similarity	NPD7516	Approved
0.619	Remote Similarity	NPD7320	Approved
0.619	Remote Similarity	NPD6881	Approved
0.619	Remote Similarity	NPD6899	Approved
0.618	Remote Similarity	NPD6929	Approved
0.617	Remote Similarity	NPD7524	Approved
0.617	Remote Similarity	NPD7750	Discontinued
0.6163	Remote Similarity	NPD4785	Approved
0.6163	Remote Similarity	NPD6926	Approved
0.6163	Remote Similarity	NPD4784	Approved
0.6163	Remote Similarity	NPD6924	Approved
0.6161	Remote Similarity	NPD8294	Approved
0.6161	Remote Similarity	NPD8377	Approved
0.6154	Remote Similarity	NPD6008	Approved
0.6139	Remote Similarity	NPD5285	Approved
0.6139	Remote Similarity	NPD4700	Approved
0.6139	Remote Similarity	NPD5286	Approved
0.6139	Remote Similarity	NPD4696	Approved
0.6136	Remote Similarity	NPD6932	Approved
0.6132	Remote Similarity	NPD6372	Approved
0.6132	Remote Similarity	NPD6373	Approved
0.6118	Remote Similarity	NPD6081	Approved
0.6106	Remote Similarity	NPD8378	Approved
0.6106	Remote Similarity	NPD8033	Approved
0.6106	Remote Similarity	NPD8335	Approved
0.6106	Remote Similarity	NPD8296	Approved
0.6106	Remote Similarity	NPD8380	Approved
0.6106	Remote Similarity	NPD8379	Approved
0.6098	Remote Similarity	NPD4224	Phase 2
0.6095	Remote Similarity	NPD5697	Approved
0.6095	Remote Similarity	NPD5701	Approved
0.6075	Remote Similarity	NPD6883	Approved
0.6075	Remote Similarity	NPD7290	Approved
0.6075	Remote Similarity	NPD7102	Approved
0.6056	Remote Similarity	NPD384	Approved
0.6056	Remote Similarity	NPD385	Approved
0.6055	Remote Similarity	NPD8133	Approved
0.6042	Remote Similarity	NPD5328	Approved
0.6023	Remote Similarity	NPD6933	Approved
0.6022	Remote Similarity	NPD4786	Approved
0.6019	Remote Similarity	NPD6650	Approved
0.6019	Remote Similarity	NPD5225	Approved
0.6019	Remote Similarity	NPD5226	Approved
0.6019	Remote Similarity	NPD4633	Approved
0.6019	Remote Similarity	NPD5211	Phase 2
0.6019	Remote Similarity	NPD8130	Phase 1
0.6019	Remote Similarity	NPD5224	Approved
0.6019	Remote Similarity	NPD6847	Approved
0.6019	Remote Similarity	NPD6649	Approved
0.6019	Remote Similarity	NPD6869	Approved
0.6019	Remote Similarity	NPD6617	Approved
0.6018	Remote Similarity	NPD6059	Approved
0.6018	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD2687	Approved
0.6	Remote Similarity	NPD2686	Approved
0.6	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6683	Phase 2
0.6	Remote Similarity	NPD2254	Approved
0.5981	Remote Similarity	NPD6014	Approved
0.5981	Remote Similarity	NPD6012	Approved
0.5981	Remote Similarity	NPD6013	Approved
0.5981	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.598	Remote Similarity	NPD8418	Phase 2
0.5963	Remote Similarity	NPD8297	Approved
0.5963	Remote Similarity	NPD6882	Approved
0.5962	Remote Similarity	NPD5175	Approved
0.5962	Remote Similarity	NPD5174	Approved
0.5957	Remote Similarity	NPD6893	Approved
0.5955	Remote Similarity	NPD6925	Approved
0.5955	Remote Similarity	NPD5776	Phase 2
0.5943	Remote Similarity	NPD6412	Phase 2
0.5941	Remote Similarity	NPD6084	Phase 2
0.5941	Remote Similarity	NPD6083	Phase 2
0.5934	Remote Similarity	NPD7514	Phase 3
0.5934	Remote Similarity	NPD7509	Discontinued
0.5926	Remote Similarity	NPD4634	Approved
0.5922	Remote Similarity	NPD5223	Approved
0.5918	Remote Similarity	NPD6079	Approved
0.5918	Remote Similarity	NPD7087	Discontinued
0.5915	Remote Similarity	NPD386	Approved
0.5915	Remote Similarity	NPD388	Approved
0.5913	Remote Similarity	NPD6370	Approved
0.5909	Remote Similarity	NPD4632	Approved
0.5909	Remote Similarity	NPD5275	Approved
0.5909	Remote Similarity	NPD4190	Phase 3
0.5905	Remote Similarity	NPD5141	Approved
0.5897	Remote Similarity	NPD7507	Approved
0.5895	Remote Similarity	NPD3618	Phase 1
0.5889	Remote Similarity	NPD7145	Approved
0.5888	Remote Similarity	NPD6011	Approved
0.5877	Remote Similarity	NPD6319	Approved
0.5876	Remote Similarity	NPD4753	Phase 2
0.5872	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6902	Approved
0.5862	Remote Similarity	NPD7604	Phase 2
0.5859	Remote Similarity	NPD6399	Phase 3
0.5851	Remote Similarity	NPD3665	Phase 1
0.5851	Remote Similarity	NPD3133	Approved
0.5851	Remote Similarity	NPD3666	Approved
0.5849	Remote Similarity	NPD4767	Approved
0.5849	Remote Similarity	NPD4768	Approved
0.5826	Remote Similarity	NPD6015	Approved
0.5826	Remote Similarity	NPD6016	Approved
0.5826	Remote Similarity	NPD7503	Approved
0.5824	Remote Similarity	NPD4195	Approved
0.5812	Remote Similarity	NPD7492	Approved
0.581	Remote Similarity	NPD4754	Approved
0.5806	Remote Similarity	NPD3667	Approved
0.5804	Remote Similarity	NPD6940	Discontinued
0.5798	Remote Similarity	NPD7736	Approved
0.5784	Remote Similarity	NPD7919	Phase 3
0.5784	Remote Similarity	NPD7920	Phase 3
0.578	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD5988	Approved
0.5763	Remote Similarity	NPD6616	Approved
0.5761	Remote Similarity	NPD7332	Phase 2
0.5752	Remote Similarity	NPD6009	Approved
0.575	Remote Similarity	NPD7319	Approved
0.5747	Remote Similarity	NPD7152	Approved
0.5747	Remote Similarity	NPD7151	Approved
0.5747	Remote Similarity	NPD7150	Approved
0.5745	Remote Similarity	NPD3669	Approved
0.5745	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD4729	Approved
0.5741	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5128	Approved
0.5741	Remote Similarity	NPD4730	Approved
0.5741	Remote Similarity	NPD8174	Phase 2
0.5728	Remote Similarity	NPD8088	Phase 1
0.5714	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD8293	Discontinued

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