NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	261.022
LogP:	2.28
LogD:	1.412
LogS:	-2.816
# Rotatable Bonds:	0
TPSA:	66.13
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.553
Synthetic Accessibility Score:	5.611
Fsp3:	0.6
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:	-5.044
MDCK Permeability:	8.692183655512054e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.977
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.304

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.702
Plasma Protein Binding (PPB):	85.7328109741211%
Volume Distribution (VD):	1.947
Pgp-substrate:	12.378125190734863%

ADMET: Metabolism

CYP1A2-inhibitor:	0.153
CYP1A2-substrate:	0.886
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.761
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.201
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.589
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	12.211
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.984
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.311
Rat Oral Acute Toxicity:	0.978
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.549
Carcinogencity:	0.371
Eye Corrosion:	0.007
Eye Irritation:	0.039
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC220221

Natural Product ID:	NPC220221
*Common Name:**	QKIQAUSGMKJYFS-CWFCOSEVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QKIQAUSGMKJYFS-CWFCOSEVSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-7-4-12(16)15-10(7)5-9-8(2)13(17)18-11(9)6-14(15,3)19-15/h4,10-12,16H,5-6H2,1-3H3/t10-,11-,12+,14+,15+/m0/s1
SMILES:	CC1=C[C@H]([C@]23[C@H]1CC1=C(C)C(=O)O[C@H]1C[C@@]2(C)O3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501119
PubChem CID:	11299991
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679319]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10449	Arctium lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10449	Arctium lappa	Species	Asteraceae	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	98200.0	nM	PMID[458469]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	>	100000.0	nM	PMID[458469]

☑ 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 NPC220221 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	224
0.1-0.2	1501
0.2-0.3	5061
0.3-0.4	12918
0.4-0.5	13187
0.5-0.6	6277
0.6-0.7	2999
0.7-0.8	481
0.8-0.85	46
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9032	High Similarity	NPC98165
0.8687	High Similarity	NPC243998
0.8571	High Similarity	NPC86077
0.85	High Similarity	NPC223450
0.8444	Intermediate Similarity	NPC154893
0.8444	Intermediate Similarity	NPC16887
0.8444	Intermediate Similarity	NPC37005
0.8444	Intermediate Similarity	NPC53011
0.8421	Intermediate Similarity	NPC323008
0.8421	Intermediate Similarity	NPC470010
0.8421	Intermediate Similarity	NPC262133
0.8421	Intermediate Similarity	NPC470013
0.8229	Intermediate Similarity	NPC198853
0.8229	Intermediate Similarity	NPC477131
0.8211	Intermediate Similarity	NPC131209
0.8211	Intermediate Similarity	NPC158061
0.8163	Intermediate Similarity	NPC205143
0.8144	Intermediate Similarity	NPC304886
0.8137	Intermediate Similarity	NPC54737
0.8132	Intermediate Similarity	NPC231601
0.8125	Intermediate Similarity	NPC32862
0.8125	Intermediate Similarity	NPC272293
0.8125	Intermediate Similarity	NPC40821
0.81	Intermediate Similarity	NPC150923
0.8081	Intermediate Similarity	NPC473326
0.8081	Intermediate Similarity	NPC221615
0.8043	Intermediate Similarity	NPC290052
0.8021	Intermediate Similarity	NPC475925
0.8021	Intermediate Similarity	NPC133698
0.802	Intermediate Similarity	NPC470972
0.8	Intermediate Similarity	NPC257240
0.8	Intermediate Similarity	NPC4986
0.7961	Intermediate Similarity	NPC470980
0.7959	Intermediate Similarity	NPC14961
0.7959	Intermediate Similarity	NPC52044
0.7959	Intermediate Similarity	NPC270013
0.7957	Intermediate Similarity	NPC287015
0.7957	Intermediate Similarity	NPC146850
0.7941	Intermediate Similarity	NPC124881
0.7925	Intermediate Similarity	NPC71680
0.7917	Intermediate Similarity	NPC3952
0.7917	Intermediate Similarity	NPC473448
0.7905	Intermediate Similarity	NPC139838
0.7905	Intermediate Similarity	NPC59489
0.79	Intermediate Similarity	NPC222303
0.7895	Intermediate Similarity	NPC91248
0.7885	Intermediate Similarity	NPC26617
0.7879	Intermediate Similarity	NPC279621
0.787	Intermediate Similarity	NPC216665
0.7864	Intermediate Similarity	NPC100487
0.7857	Intermediate Similarity	NPC472467
0.7857	Intermediate Similarity	NPC474035
0.7857	Intermediate Similarity	NPC81386
0.785	Intermediate Similarity	NPC35069
0.785	Intermediate Similarity	NPC258711
0.7849	Intermediate Similarity	NPC186155
0.7849	Intermediate Similarity	NPC78673
0.7849	Intermediate Similarity	NPC160517
0.783	Intermediate Similarity	NPC15551
0.7822	Intermediate Similarity	NPC70865
0.7822	Intermediate Similarity	NPC471381
0.7822	Intermediate Similarity	NPC130792
0.781	Intermediate Similarity	NPC308191
0.78	Intermediate Similarity	NPC161493
0.78	Intermediate Similarity	NPC477949
0.7789	Intermediate Similarity	NPC471657
0.7789	Intermediate Similarity	NPC45957
0.7789	Intermediate Similarity	NPC191283
0.7788	Intermediate Similarity	NPC166115
0.7788	Intermediate Similarity	NPC179891
0.7778	Intermediate Similarity	NPC170120
0.7778	Intermediate Similarity	NPC46269
0.7778	Intermediate Similarity	NPC469873
0.7778	Intermediate Similarity	NPC67584
0.7778	Intermediate Similarity	NPC106395
0.7755	Intermediate Similarity	NPC258216
0.7755	Intermediate Similarity	NPC212486
0.7755	Intermediate Similarity	NPC228451
0.7755	Intermediate Similarity	NPC475838
0.7755	Intermediate Similarity	NPC135776
0.7755	Intermediate Similarity	NPC125674
0.7755	Intermediate Similarity	NPC475912
0.7736	Intermediate Similarity	NPC477102
0.7723	Intermediate Similarity	NPC45125
0.7723	Intermediate Similarity	NPC187268
0.7717	Intermediate Similarity	NPC474894
0.7706	Intermediate Similarity	NPC43213
0.7706	Intermediate Similarity	NPC67290
0.7706	Intermediate Similarity	NPC133677
0.7706	Intermediate Similarity	NPC121816
0.7706	Intermediate Similarity	NPC138303
0.77	Intermediate Similarity	NPC476315
0.77	Intermediate Similarity	NPC473333
0.77	Intermediate Similarity	NPC213078
0.7692	Intermediate Similarity	NPC203659
0.7692	Intermediate Similarity	NPC86971
0.7692	Intermediate Similarity	NPC474741
0.7685	Intermediate Similarity	NPC76550
0.7685	Intermediate Similarity	NPC241477
0.7685	Intermediate Similarity	NPC138757
0.7685	Intermediate Similarity	NPC95290
0.7685	Intermediate Similarity	NPC189338
0.7685	Intermediate Similarity	NPC123855
0.7684	Intermediate Similarity	NPC61527
0.7684	Intermediate Similarity	NPC204048
0.7684	Intermediate Similarity	NPC311163
0.7677	Intermediate Similarity	NPC474247
0.7677	Intermediate Similarity	NPC303942
0.7677	Intermediate Similarity	NPC57405
0.7667	Intermediate Similarity	NPC471454
0.7667	Intermediate Similarity	NPC84360
0.7664	Intermediate Similarity	NPC477103
0.7653	Intermediate Similarity	NPC472468
0.7653	Intermediate Similarity	NPC155215
0.7647	Intermediate Similarity	NPC186861
0.7647	Intermediate Similarity	NPC79631
0.7647	Intermediate Similarity	NPC288876
0.7647	Intermediate Similarity	NPC475053
0.7629	Intermediate Similarity	NPC133450
0.7629	Intermediate Similarity	NPC32922
0.7629	Intermediate Similarity	NPC212664
0.7629	Intermediate Similarity	NPC473564
0.7629	Intermediate Similarity	NPC215556
0.7624	Intermediate Similarity	NPC181151
0.7624	Intermediate Similarity	NPC2666
0.7624	Intermediate Similarity	NPC474313
0.7624	Intermediate Similarity	NPC182811
0.7615	Intermediate Similarity	NPC273242
0.7609	Intermediate Similarity	NPC474739
0.76	Intermediate Similarity	NPC240838
0.76	Intermediate Similarity	NPC37408
0.76	Intermediate Similarity	NPC472873
0.76	Intermediate Similarity	NPC213698
0.76	Intermediate Similarity	NPC36954
0.76	Intermediate Similarity	NPC329435
0.7596	Intermediate Similarity	NPC110989
0.7596	Intermediate Similarity	NPC475945
0.7596	Intermediate Similarity	NPC475871
0.7593	Intermediate Similarity	NPC287311
0.7579	Intermediate Similarity	NPC471494
0.7579	Intermediate Similarity	NPC471185
0.7576	Intermediate Similarity	NPC179746
0.7576	Intermediate Similarity	NPC81419
0.7576	Intermediate Similarity	NPC471483
0.7573	Intermediate Similarity	NPC20673
0.7573	Intermediate Similarity	NPC219038
0.7568	Intermediate Similarity	NPC475323
0.7556	Intermediate Similarity	NPC170148
0.7553	Intermediate Similarity	NPC471340
0.7551	Intermediate Similarity	NPC216284
0.7551	Intermediate Similarity	NPC471184
0.7551	Intermediate Similarity	NPC177668
0.7551	Intermediate Similarity	NPC129419
0.7551	Intermediate Similarity	NPC472466
0.7551	Intermediate Similarity	NPC301969
0.7551	Intermediate Similarity	NPC209816
0.7551	Intermediate Similarity	NPC474761
0.7551	Intermediate Similarity	NPC37607
0.7551	Intermediate Similarity	NPC476004
0.7549	Intermediate Similarity	NPC79449
0.7549	Intermediate Similarity	NPC274458
0.7549	Intermediate Similarity	NPC474213
0.7549	Intermediate Similarity	NPC474957
0.7547	Intermediate Similarity	NPC108682
0.7547	Intermediate Similarity	NPC469959
0.7547	Intermediate Similarity	NPC472263
0.7547	Intermediate Similarity	NPC469957
0.7526	Intermediate Similarity	NPC207114
0.7526	Intermediate Similarity	NPC281516
0.7526	Intermediate Similarity	NPC217983
0.7526	Intermediate Similarity	NPC153805
0.7526	Intermediate Similarity	NPC79549
0.7525	Intermediate Similarity	NPC230800
0.7525	Intermediate Similarity	NPC18019
0.7525	Intermediate Similarity	NPC24956
0.7525	Intermediate Similarity	NPC472995
0.75	Intermediate Similarity	NPC55304
0.75	Intermediate Similarity	NPC473316
0.75	Intermediate Similarity	NPC127019
0.75	Intermediate Similarity	NPC281775
0.75	Intermediate Similarity	NPC473330
0.75	Intermediate Similarity	NPC474747
0.75	Intermediate Similarity	NPC200672
0.75	Intermediate Similarity	NPC187661
0.75	Intermediate Similarity	NPC225353
0.75	Intermediate Similarity	NPC476701
0.75	Intermediate Similarity	NPC471599
0.75	Intermediate Similarity	NPC214714
0.75	Intermediate Similarity	NPC226226
0.7477	Intermediate Similarity	NPC117604
0.7477	Intermediate Similarity	NPC255450
0.7477	Intermediate Similarity	NPC181994
0.7477	Intermediate Similarity	NPC170692
0.7476	Intermediate Similarity	NPC38855
0.7476	Intermediate Similarity	NPC244878
0.7475	Intermediate Similarity	NPC208886
0.7475	Intermediate Similarity	NPC30515
0.7475	Intermediate Similarity	NPC184063
0.7475	Intermediate Similarity	NPC184463
0.7475	Intermediate Similarity	NPC12172

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 NPC220221 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	2044
0.2-0.3	3853
0.3-0.4	2197
0.4-0.5	643
0.5-0.6	157
0.6-0.7	30
0.7-0.8	4
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
0.8	Intermediate Similarity	NPD6371	Approved
0.8	Intermediate Similarity	NPD1695	Approved
0.7917	Intermediate Similarity	NPD7838	Discovery
0.7885	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD6698	Approved
0.7732	Intermediate Similarity	NPD46	Approved
0.7573	Intermediate Similarity	NPD5344	Discontinued
0.7143	Intermediate Similarity	NPD6648	Approved
0.7143	Intermediate Similarity	NPD4249	Approved
0.7087	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4250	Approved
0.7071	Intermediate Similarity	NPD4251	Approved
0.7054	Intermediate Similarity	NPD6053	Discontinued
0.7041	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5362	Discontinued
0.6897	Remote Similarity	NPD7327	Approved
0.6897	Remote Similarity	NPD7328	Approved
0.6887	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4225	Approved
0.6875	Remote Similarity	NPD4821	Approved
0.6875	Remote Similarity	NPD4819	Approved
0.6875	Remote Similarity	NPD4822	Approved
0.6875	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4820	Approved
0.6869	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8033	Approved
0.6847	Remote Similarity	NPD6686	Approved
0.6838	Remote Similarity	NPD7516	Approved
0.6837	Remote Similarity	NPD7154	Phase 3
0.6822	Remote Similarity	NPD7640	Approved
0.6822	Remote Similarity	NPD7639	Approved
0.6796	Remote Similarity	NPD7983	Approved
0.6786	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8294	Approved
0.678	Remote Similarity	NPD8377	Approved
0.6729	Remote Similarity	NPD7638	Approved
0.6723	Remote Similarity	NPD8379	Approved
0.6723	Remote Similarity	NPD8378	Approved
0.6723	Remote Similarity	NPD8296	Approved
0.6723	Remote Similarity	NPD8380	Approved
0.6723	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6639	Remote Similarity	NPD7507	Approved
0.6633	Remote Similarity	NPD4790	Discontinued
0.6629	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7524	Approved
0.6538	Remote Similarity	NPD5785	Approved
0.6522	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7319	Approved
0.6476	Remote Similarity	NPD7637	Suspended
0.6446	Remote Similarity	NPD7503	Approved
0.6436	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5363	Approved
0.6355	Remote Similarity	NPD5282	Discontinued
0.6337	Remote Similarity	NPD6695	Phase 3
0.6262	Remote Similarity	NPD5778	Approved
0.6262	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD7632	Discontinued
0.624	Remote Similarity	NPD8273	Phase 1
0.6239	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4270	Approved
0.6238	Remote Similarity	NPD4269	Approved
0.6238	Remote Similarity	NPD6435	Approved
0.6228	Remote Similarity	NPD6008	Approved
0.6174	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6412	Phase 2
0.6162	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5786	Approved
0.6139	Remote Similarity	NPD5369	Approved
0.6134	Remote Similarity	NPD4632	Approved
0.6116	Remote Similarity	NPD7505	Discontinued
0.6098	Remote Similarity	NPD6319	Approved
0.6095	Remote Similarity	NPD7750	Discontinued
0.6078	Remote Similarity	NPD5209	Approved
0.6078	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8516	Approved
0.6048	Remote Similarity	NPD8517	Approved
0.6048	Remote Similarity	NPD8515	Approved
0.6048	Remote Similarity	NPD8513	Phase 3
0.604	Remote Similarity	NPD5368	Approved
0.604	Remote Similarity	NPD6930	Phase 2
0.604	Remote Similarity	NPD6931	Approved
0.604	Remote Similarity	NPD4252	Approved
0.604	Remote Similarity	NPD7332	Phase 2
0.6036	Remote Similarity	NPD6084	Phase 2
0.6036	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD6110	Phase 1
0.6	Remote Similarity	NPD5695	Phase 3
0.5983	Remote Similarity	NPD7320	Approved
0.5981	Remote Similarity	NPD6051	Approved
0.5948	Remote Similarity	NPD6402	Approved
0.5948	Remote Similarity	NPD5739	Approved
0.5948	Remote Similarity	NPD6675	Approved
0.5948	Remote Similarity	NPD7128	Approved
0.5948	Remote Similarity	NPD6640	Phase 3
0.5941	Remote Similarity	NPD6929	Approved
0.5926	Remote Similarity	NPD3168	Discontinued
0.5917	Remote Similarity	NPD8297	Approved
0.5906	Remote Similarity	NPD7492	Approved
0.5897	Remote Similarity	NPD5697	Approved
0.5897	Remote Similarity	NPD5701	Approved
0.5882	Remote Similarity	NPD7514	Phase 3
0.5872	Remote Similarity	NPD7087	Discontinued
0.5868	Remote Similarity	NPD8133	Approved
0.5859	Remote Similarity	NPD6616	Approved
0.5854	Remote Similarity	NPD6009	Approved
0.5847	Remote Similarity	NPD6899	Approved
0.5847	Remote Similarity	NPD6881	Approved
0.5841	Remote Similarity	NPD5696	Approved
0.584	Remote Similarity	NPD6059	Approved
0.584	Remote Similarity	NPD6054	Approved
0.5833	Remote Similarity	NPD2204	Approved
0.5827	Remote Similarity	NPD7829	Approved
0.5827	Remote Similarity	NPD7642	Approved
0.5827	Remote Similarity	NPD7830	Approved
0.5827	Remote Similarity	NPD7604	Phase 2
0.5825	Remote Similarity	NPD6898	Phase 1
0.5825	Remote Similarity	NPD6902	Approved
0.5818	Remote Similarity	NPD6399	Phase 3
0.5814	Remote Similarity	NPD8074	Phase 3
0.5814	Remote Similarity	NPD7078	Approved
0.5814	Remote Similarity	NPD8293	Discontinued
0.5804	Remote Similarity	NPD7839	Suspended
0.58	Remote Similarity	NPD6933	Approved
0.5798	Remote Similarity	NPD6013	Approved
0.5798	Remote Similarity	NPD6014	Approved
0.5798	Remote Similarity	NPD6373	Approved
0.5798	Remote Similarity	NPD6012	Approved
0.5798	Remote Similarity	NPD6372	Approved
0.5794	Remote Similarity	NPD6015	Approved
0.5794	Remote Similarity	NPD5983	Phase 2
0.5794	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6016	Approved
0.5769	Remote Similarity	NPD7736	Approved
0.5761	Remote Similarity	NPD368	Approved
0.5755	Remote Similarity	NPD6893	Approved
0.5755	Remote Similarity	NPD1694	Approved
0.575	Remote Similarity	NPD6883	Approved
0.575	Remote Similarity	NPD7102	Approved
0.575	Remote Similarity	NPD7290	Approved
0.5748	Remote Similarity	NPD6370	Approved
0.5748	Remote Similarity	NPD5988	Approved
0.5743	Remote Similarity	NPD6925	Approved
0.5743	Remote Similarity	NPD5776	Phase 2
0.5727	Remote Similarity	NPD5693	Phase 1
0.5714	Remote Similarity	NPD6011	Approved
0.5702	Remote Similarity	NPD6847	Approved
0.5702	Remote Similarity	NPD6649	Approved
0.5702	Remote Similarity	NPD6617	Approved
0.5702	Remote Similarity	NPD8130	Phase 1
0.5702	Remote Similarity	NPD6650	Approved
0.5702	Remote Similarity	NPD6869	Approved
0.569	Remote Similarity	NPD5211	Phase 2
0.569	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD6101	Approved
0.5688	Remote Similarity	NPD4753	Phase 2
0.5686	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD7145	Approved
0.5656	Remote Similarity	NPD6882	Approved
0.563	Remote Similarity	NPD6685	Approved
0.562	Remote Similarity	NPD4634	Approved
0.562	Remote Similarity	NPD6421	Discontinued
0.5615	Remote Similarity	NPD6336	Discontinued
0.5614	Remote Similarity	NPD4755	Approved
0.5607	Remote Similarity	NPD1696	Phase 3
0.5604	Remote Similarity	NPD9119	Approved
0.5604	Remote Similarity	NPD69	Approved
0.5604	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD4159	Approved
0.56	Remote Similarity	NPD6926	Approved
0.56	Remote Similarity	NPD6924	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