NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	224.1
Volume:	232.167
LogP:	3.057
LogD:	2.627
LogS:	-3.248
# Rotatable Bonds:	5
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.595
Synthetic Accessibility Score:	2.138
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.622
MDCK Permeability:	2.08647961699171e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.361
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.15
Plasma Protein Binding (PPB):	89.57698822021484%
Volume Distribution (VD):	0.814
Pgp-substrate:	11.983651161193848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.881
CYP2C19-inhibitor:	0.385
CYP2C19-substrate:	0.325
CYP2C9-inhibitor:	0.505
CYP2C9-substrate:	0.863
CYP2D6-inhibitor:	0.529
CYP2D6-substrate:	0.802
CYP3A4-inhibitor:	0.179
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	12.91
Half-life (T1/2):	0.895

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.049
Drug-inuced Liver Injury (DILI):	0.173
AMES Toxicity:	0.127
Rat Oral Acute Toxicity:	0.213
Maximum Recommended Daily Dose:	0.338
Skin Sensitization:	0.848
Carcinogencity:	0.086
Eye Corrosion:	0.107
Eye Irritation:	0.951
Respiratory Toxicity:	0.317

Download Data

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

Natural Product: NPC473536

Natural Product ID:	NPC473536
*Common Name:**	2-Methoxy-5-(1-Hydroxypentyl)-1,4-Benzoquinone
IUPAC Name:	2-(1-hydroxypentyl)-6-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	QEYTVHCFIMCNLT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H16O4/c1-3-4-5-10(14)9-6-8(13)7-11(16-2)12(9)15/h6-7,10,14H,3-5H2,1-2H3
SMILES:	CCCCC(C1=CC(=O)C=C(C1=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444781
PubChem CID:	10656752
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0002495] Quinones [CHEMONTID:0002384] Benzoquinones [CHEMONTID:0002494] P-benzoquinones

*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
NPO25763	Miconia lepidota	Species	Melastomataceae	Eukaryota	n.a.	Suriname rainforest	n.a.	PMID[11170656]
NPO25763	Miconia lepidota	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170656]
NPO25763	Miconia lepidota	Species	Melastomataceae	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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	=	438.0	ug ml-1	PMID[559626]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	=	430.0	ug ml-1	PMID[559626]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	=	577.0	ug ml-1	PMID[559626]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	=	536.0	ug ml-1	PMID[559626]

☑ 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 NPC473536 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	176
0.1-0.2	1477
0.2-0.3	6654
0.3-0.4	14637
0.4-0.5	12967
0.5-0.6	5112
0.6-0.7	1488
0.7-0.8	168
0.8-0.85	16
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8608	High Similarity	NPC47450
0.8493	Intermediate Similarity	NPC262673
0.8493	Intermediate Similarity	NPC94488
0.8472	Intermediate Similarity	NPC243272
0.8378	Intermediate Similarity	NPC291062
0.8378	Intermediate Similarity	NPC94743
0.8356	Intermediate Similarity	NPC146376
0.8356	Intermediate Similarity	NPC263382
0.8356	Intermediate Similarity	NPC125578
0.8169	Intermediate Similarity	NPC151728
0.8169	Intermediate Similarity	NPC57463
0.8056	Intermediate Similarity	NPC474400
0.8056	Intermediate Similarity	NPC34622
0.8052	Intermediate Similarity	NPC264178
0.8	Intermediate Similarity	NPC53454
0.7976	Intermediate Similarity	NPC472009
0.7973	Intermediate Similarity	NPC474619
0.7952	Intermediate Similarity	NPC469809
0.7945	Intermediate Similarity	NPC98897
0.7917	Intermediate Similarity	NPC143168
0.7917	Intermediate Similarity	NPC53109
0.7917	Intermediate Similarity	NPC477830
0.7882	Intermediate Similarity	NPC472007
0.7875	Intermediate Similarity	NPC478122
0.7857	Intermediate Similarity	NPC77971
0.7848	Intermediate Similarity	NPC477708
0.7838	Intermediate Similarity	NPC16119
0.7831	Intermediate Similarity	NPC477784
0.7831	Intermediate Similarity	NPC477786
0.7831	Intermediate Similarity	NPC477785
0.7808	Intermediate Similarity	NPC7029
0.7791	Intermediate Similarity	NPC472008
0.7746	Intermediate Similarity	NPC473494
0.7733	Intermediate Similarity	NPC251429
0.7674	Intermediate Similarity	NPC471738
0.7654	Intermediate Similarity	NPC231739
0.7647	Intermediate Similarity	NPC187529
0.7632	Intermediate Similarity	NPC134385
0.7614	Intermediate Similarity	NPC471399
0.7606	Intermediate Similarity	NPC320421
0.76	Intermediate Similarity	NPC472072
0.759	Intermediate Similarity	NPC221510
0.759	Intermediate Similarity	NPC159714
0.7531	Intermediate Similarity	NPC471061
0.7531	Intermediate Similarity	NPC272267
0.75	Intermediate Similarity	NPC253364
0.7468	Intermediate Similarity	NPC275098
0.7442	Intermediate Similarity	NPC255174
0.7439	Intermediate Similarity	NPC475994
0.7436	Intermediate Similarity	NPC477455
0.7412	Intermediate Similarity	NPC185256
0.7407	Intermediate Similarity	NPC16279
0.7407	Intermediate Similarity	NPC205615
0.7407	Intermediate Similarity	NPC256640
0.7356	Intermediate Similarity	NPC261721
0.7312	Intermediate Similarity	NPC471916
0.7312	Intermediate Similarity	NPC20066
0.7308	Intermediate Similarity	NPC143396
0.7283	Intermediate Similarity	NPC91408
0.7262	Intermediate Similarity	NPC162741
0.7262	Intermediate Similarity	NPC91332
0.7241	Intermediate Similarity	NPC68303
0.7241	Intermediate Similarity	NPC307126
0.7234	Intermediate Similarity	NPC300584
0.7229	Intermediate Similarity	NPC248624
0.7222	Intermediate Similarity	NPC166554
0.7222	Intermediate Similarity	NPC477684
0.7222	Intermediate Similarity	NPC265856
0.7188	Intermediate Similarity	NPC39996
0.7179	Intermediate Similarity	NPC477452
0.7176	Intermediate Similarity	NPC275766
0.7174	Intermediate Similarity	NPC121825
0.716	Intermediate Similarity	NPC122244
0.716	Intermediate Similarity	NPC227396
0.716	Intermediate Similarity	NPC215050
0.7143	Intermediate Similarity	NPC114345
0.7143	Intermediate Similarity	NPC32552
0.7143	Intermediate Similarity	NPC19900
0.7143	Intermediate Similarity	NPC303230
0.7143	Intermediate Similarity	NPC172101
0.7143	Intermediate Similarity	NPC6099
0.7128	Intermediate Similarity	NPC471694
0.7126	Intermediate Similarity	NPC474251
0.7123	Intermediate Similarity	NPC139056
0.7113	Intermediate Similarity	NPC131366
0.7108	Intermediate Similarity	NPC82666
0.7108	Intermediate Similarity	NPC97173
0.7093	Intermediate Similarity	NPC158411
0.7093	Intermediate Similarity	NPC38796
0.7083	Intermediate Similarity	NPC469851
0.7083	Intermediate Similarity	NPC207885
0.7079	Intermediate Similarity	NPC272039
0.7079	Intermediate Similarity	NPC220930
0.7073	Intermediate Similarity	NPC260396
0.7073	Intermediate Similarity	NPC60718
0.7073	Intermediate Similarity	NPC474885
0.7071	Intermediate Similarity	NPC469853
0.7065	Intermediate Similarity	NPC469692
0.7065	Intermediate Similarity	NPC469645
0.7059	Intermediate Similarity	NPC470947
0.7059	Intermediate Similarity	NPC470945
0.7059	Intermediate Similarity	NPC45495
0.7059	Intermediate Similarity	NPC470946
0.7051	Intermediate Similarity	NPC122627
0.7045	Intermediate Similarity	NPC470755
0.7045	Intermediate Similarity	NPC241512
0.7045	Intermediate Similarity	NPC132228
0.7045	Intermediate Similarity	NPC8518
0.7045	Intermediate Similarity	NPC263997
0.7045	Intermediate Similarity	NPC32037
0.7045	Intermediate Similarity	NPC28887
0.7045	Intermediate Similarity	NPC6185
0.7045	Intermediate Similarity	NPC15807
0.7045	Intermediate Similarity	NPC474853
0.7045	Intermediate Similarity	NPC261380
0.7045	Intermediate Similarity	NPC179006
0.7042	Intermediate Similarity	NPC317796
0.7037	Intermediate Similarity	NPC186042
0.7033	Intermediate Similarity	NPC145666
0.7033	Intermediate Similarity	NPC131864
0.7033	Intermediate Similarity	NPC469464
0.7021	Intermediate Similarity	NPC184065
0.7011	Intermediate Similarity	NPC62214
0.7	Intermediate Similarity	NPC475819
0.7	Intermediate Similarity	NPC107848
0.7	Intermediate Similarity	NPC173321
0.6989	Remote Similarity	NPC469632
0.6986	Remote Similarity	NPC268185
0.6974	Remote Similarity	NPC477707
0.697	Remote Similarity	NPC469852
0.6966	Remote Similarity	NPC194417
0.6966	Remote Similarity	NPC315395
0.6966	Remote Similarity	NPC316426
0.6966	Remote Similarity	NPC196381
0.6966	Remote Similarity	NPC202394
0.6957	Remote Similarity	NPC146852
0.6957	Remote Similarity	NPC193396
0.6957	Remote Similarity	NPC32944
0.6957	Remote Similarity	NPC327760
0.6951	Remote Similarity	NPC147438
0.6941	Remote Similarity	NPC281138
0.6941	Remote Similarity	NPC291260
0.6941	Remote Similarity	NPC7232
0.6941	Remote Similarity	NPC308038
0.6941	Remote Similarity	NPC113363
0.6939	Remote Similarity	NPC104161
0.6939	Remote Similarity	NPC118902
0.6939	Remote Similarity	NPC469980
0.6932	Remote Similarity	NPC158756
0.6932	Remote Similarity	NPC141193
0.6932	Remote Similarity	NPC472326
0.6932	Remote Similarity	NPC96259
0.6932	Remote Similarity	NPC469884
0.6932	Remote Similarity	NPC219966
0.6931	Remote Similarity	NPC20192
0.6923	Remote Similarity	NPC95364
0.6923	Remote Similarity	NPC14901
0.6923	Remote Similarity	NPC142159
0.6923	Remote Similarity	NPC280833
0.6923	Remote Similarity	NPC130359
0.6923	Remote Similarity	NPC307092
0.6915	Remote Similarity	NPC279313
0.6907	Remote Similarity	NPC46998
0.6907	Remote Similarity	NPC112613
0.6907	Remote Similarity	NPC133907
0.6907	Remote Similarity	NPC128733
0.6907	Remote Similarity	NPC470184
0.6907	Remote Similarity	NPC185141
0.6907	Remote Similarity	NPC110443
0.6905	Remote Similarity	NPC47844
0.6905	Remote Similarity	NPC141195
0.6905	Remote Similarity	NPC211279
0.6901	Remote Similarity	NPC474805
0.6897	Remote Similarity	NPC103486
0.6897	Remote Similarity	NPC279186
0.6897	Remote Similarity	NPC85772
0.6889	Remote Similarity	NPC23622
0.6882	Remote Similarity	NPC475302
0.6882	Remote Similarity	NPC61275
0.6882	Remote Similarity	NPC327620
0.6875	Remote Similarity	NPC35717
0.6875	Remote Similarity	NPC250928
0.6875	Remote Similarity	NPC306908
0.6875	Remote Similarity	NPC236208
0.6875	Remote Similarity	NPC10758
0.686	Remote Similarity	NPC104120
0.686	Remote Similarity	NPC157895
0.686	Remote Similarity	NPC148685
0.686	Remote Similarity	NPC47653
0.686	Remote Similarity	NPC271104
0.6854	Remote Similarity	NPC307112
0.6854	Remote Similarity	NPC70685
0.6854	Remote Similarity	NPC165162
0.6854	Remote Similarity	NPC67081
0.6854	Remote Similarity	NPC182383
0.6854	Remote Similarity	NPC471223
0.6854	Remote Similarity	NPC79573
0.6854	Remote Similarity	NPC476426
0.6849	Remote Similarity	NPC40148
0.6842	Remote Similarity	NPC94337

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 NPC473536 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	2213
0.2-0.3	3862
0.3-0.4	2130
0.4-0.5	543
0.5-0.6	214
0.6-0.7	25
0.7-0.8	3
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
0.8442	Intermediate Similarity	NPD4756	Discovery
0.8333	Intermediate Similarity	NPD3704	Approved
0.7917	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6110	Phase 1
0.6854	Remote Similarity	NPD5363	Approved
0.6809	Remote Similarity	NPD5282	Discontinued
0.6757	Remote Similarity	NPD8779	Phase 3
0.6667	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.6629	Remote Similarity	NPD7154	Phase 3
0.6517	Remote Similarity	NPD4269	Approved
0.6517	Remote Similarity	NPD4270	Approved
0.65	Remote Similarity	NPD7331	Phase 2
0.6484	Remote Similarity	NPD1696	Phase 3
0.6477	Remote Similarity	NPD4252	Approved
0.6477	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3197	Phase 1
0.6413	Remote Similarity	NPD5786	Approved
0.6392	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5778	Approved
0.6354	Remote Similarity	NPD5779	Approved
0.6316	Remote Similarity	NPD46	Approved
0.6316	Remote Similarity	NPD6698	Approved
0.6267	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5362	Discontinued
0.625	Remote Similarity	NPD7983	Approved
0.6237	Remote Similarity	NPD5279	Phase 3
0.6222	Remote Similarity	NPD5369	Approved
0.6176	Remote Similarity	NPD5211	Phase 2
0.6111	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4268	Approved
0.6067	Remote Similarity	NPD4271	Approved
0.6067	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4249	Approved
0.6058	Remote Similarity	NPD5141	Approved
0.6042	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4753	Phase 2
0.6042	Remote Similarity	NPD6101	Approved
0.6042	Remote Similarity	NPD5370	Suspended
0.6024	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3665	Phase 1
0.6022	Remote Similarity	NPD3666	Approved
0.6022	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD368	Approved
0.6	Remote Similarity	NPD7839	Suspended
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4250	Approved
0.6	Remote Similarity	NPD4251	Approved
0.6	Remote Similarity	NPD5221	Approved
0.598	Remote Similarity	NPD5285	Approved
0.598	Remote Similarity	NPD4696	Approved
0.598	Remote Similarity	NPD5286	Approved
0.5978	Remote Similarity	NPD3667	Approved
0.5978	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD7341	Phase 2
0.5943	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5697	Approved
0.5941	Remote Similarity	NPD4755	Approved
0.5941	Remote Similarity	NPD6084	Phase 2
0.5941	Remote Similarity	NPD6083	Phase 2
0.5941	Remote Similarity	NPD5173	Approved
0.5934	Remote Similarity	NPD4819	Approved
0.5934	Remote Similarity	NPD4821	Approved
0.5934	Remote Similarity	NPD4820	Approved
0.5934	Remote Similarity	NPD4822	Approved
0.5926	Remote Similarity	NPD6371	Approved
0.5922	Remote Similarity	NPD5223	Approved
0.5918	Remote Similarity	NPD6411	Approved
0.59	Remote Similarity	NPD5210	Approved
0.59	Remote Similarity	NPD4629	Approved
0.59	Remote Similarity	NPD5695	Phase 3
0.5895	Remote Similarity	NPD3618	Phase 1
0.5888	Remote Similarity	NPD6881	Approved
0.5888	Remote Similarity	NPD6899	Approved
0.5888	Remote Similarity	NPD6011	Approved
0.5882	Remote Similarity	NPD4225	Approved
0.5877	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD5224	Approved
0.5865	Remote Similarity	NPD4633	Approved
0.5865	Remote Similarity	NPD5225	Approved
0.5865	Remote Similarity	NPD5226	Approved
0.5851	Remote Similarity	NPD4786	Approved
0.5849	Remote Similarity	NPD5739	Approved
0.5849	Remote Similarity	NPD6402	Approved
0.5849	Remote Similarity	NPD7128	Approved
0.5849	Remote Similarity	NPD6675	Approved
0.5844	Remote Similarity	NPD342	Phase 1
0.5842	Remote Similarity	NPD4697	Phase 3
0.5833	Remote Similarity	NPD6013	Approved
0.5833	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD6014	Approved
0.5825	Remote Similarity	NPD4700	Approved
0.581	Remote Similarity	NPD5175	Approved
0.581	Remote Similarity	NPD5174	Approved
0.5806	Remote Similarity	NPD5209	Approved
0.5806	Remote Similarity	NPD6435	Approved
0.5794	Remote Similarity	NPD5701	Approved
0.5789	Remote Similarity	NPD1694	Approved
0.5789	Remote Similarity	NPD3172	Approved
0.578	Remote Similarity	NPD7102	Approved
0.578	Remote Similarity	NPD7290	Approved
0.578	Remote Similarity	NPD4634	Approved
0.578	Remote Similarity	NPD6883	Approved
0.5773	Remote Similarity	NPD5737	Approved
0.5773	Remote Similarity	NPD6672	Approved
0.5761	Remote Similarity	NPD5368	Approved
0.5758	Remote Similarity	NPD6079	Approved
0.5758	Remote Similarity	NPD7515	Phase 2
0.5752	Remote Similarity	NPD7500	Approved
0.5752	Remote Similarity	NPD7115	Discovery
0.5745	Remote Similarity	NPD5331	Approved
0.5745	Remote Similarity	NPD5332	Approved
0.5741	Remote Similarity	NPD7320	Approved
0.5729	Remote Similarity	NPD4623	Approved
0.5729	Remote Similarity	NPD4519	Discontinued
0.5729	Remote Similarity	NPD5690	Phase 2
0.5729	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5696	Approved
0.5727	Remote Similarity	NPD6649	Approved
0.5727	Remote Similarity	NPD6617	Approved
0.5727	Remote Similarity	NPD8130	Phase 1
0.5727	Remote Similarity	NPD6869	Approved
0.5727	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6847	Approved
0.5727	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD3196	Approved
0.5714	Remote Similarity	NPD3195	Phase 2
0.5714	Remote Similarity	NPD3617	Approved
0.5714	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4266	Approved
0.5714	Remote Similarity	NPD5328	Approved
0.5714	Remote Similarity	NPD3194	Approved
0.57	Remote Similarity	NPD6399	Phase 3
0.57	Remote Similarity	NPD4202	Approved
0.5699	Remote Similarity	NPD4790	Discontinued
0.5688	Remote Similarity	NPD6373	Approved
0.5688	Remote Similarity	NPD6372	Approved
0.5684	Remote Similarity	NPD4197	Approved
0.5684	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6882	Approved
0.5676	Remote Similarity	NPD6053	Discontinued
0.5676	Remote Similarity	NPD8297	Approved
0.5667	Remote Similarity	NPD819	Approved
0.5667	Remote Similarity	NPD818	Approved
0.566	Remote Similarity	NPD4754	Approved
0.5657	Remote Similarity	NPD7838	Discovery
0.5644	Remote Similarity	NPD7748	Approved
0.5638	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD7902	Approved
0.5625	Remote Similarity	NPD5329	Approved
0.5607	Remote Similarity	NPD1237	Approved
0.5603	Remote Similarity	NPD6054	Approved
0.5603	Remote Similarity	NPD6319	Approved
0.56	Remote Similarity	NPD7637	Suspended

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