NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.18
Volume:	283.77
LogP:	3.439
LogD:	2.979
LogS:	-3.076
# Rotatable Bonds:	4
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.704
Synthetic Accessibility Score:	3.365
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.614
MDCK Permeability:	1.6455658624181524e-05
Pgp-inhibitor:	0.473
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.915
30% Bioavailability (F30%):	0.182

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.975
Plasma Protein Binding (PPB):	86.34337615966797%
Volume Distribution (VD):	1.595
Pgp-substrate:	11.839333534240723%

ADMET: Metabolism

CYP1A2-inhibitor:	0.142
CYP1A2-substrate:	0.253
CYP2C19-inhibitor:	0.529
CYP2C19-substrate:	0.773
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.322
CYP3A4-inhibitor:	0.074
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	11.531
Half-life (T1/2):	0.814

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.948
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.339
Rat Oral Acute Toxicity:	0.475
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.031
Carcinogencity:	0.476
Eye Corrosion:	0.034
Eye Irritation:	0.672
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC106613

Natural Product ID:	NPC106613
*Common Name:**	Comosone A
IUPAC Name:	(4R)-4-hydroxy-6,6-bis(3-methylbut-2-enyl)cyclohex-2-en-1-one
Synonyms:	Comosone A
Standard InCHIKey:	DHMJQJOXFBGZRW-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C16H24O2/c1-12(2)7-9-16(10-8-13(3)4)11-14(17)5-6-15(16)18/h5-8,14,17H,9-11H2,1-4H3/t14-/m0/s1
SMILES:	O[C@H]1C=CC(=O)C(C1)(CC=C(C)C)CC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773909
PubChem CID:	52952530
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:0004325] Cyclohexenones

*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
NPO16286	Sporochnus comosus	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348445]
NPO17827	Scutellaria przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5730	Lactuca canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5730	Lactuca canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17845	Rhynchotechum vestitum	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17827	Scutellaria przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17950	Siphonoglossa ramosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5730	Lactuca canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1266	Trigonella polycerata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14726	Alnus subcordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13576	Cordylanthus tenuis	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13944	Parkia speciosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17183	Chaetomium coarctatum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17845	Rhynchotechum vestitum	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17827	Scutellaria przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16286	Sporochnus comosus	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17714	Blepharispermum zanguebaricum	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
GI50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	13000.0	nM	PMID[491420]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	14000.0	nM	PMID[491420]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	19000.0	nM	PMID[491420]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	19000.0	nM	PMID[491420]
NPT913	Cell Line	CHO-K1	Cricetulus griseus	GI50	=	17000.0	nM	PMID[491420]

☑ 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 NPC106613 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	145
0.1-0.2	1475
0.2-0.3	8473
0.3-0.4	17347
0.4-0.5	8049
0.5-0.6	5533
0.6-0.7	1486
0.7-0.8	166
0.8-0.85	13
0.85-0.9	3
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC269737
0.8788	High Similarity	NPC269985
0.8696	High Similarity	NPC29542
0.8696	High Similarity	NPC201562
0.8696	High Similarity	NPC323437
0.8429	Intermediate Similarity	NPC186042
0.8382	Intermediate Similarity	NPC117804
0.8286	Intermediate Similarity	NPC95863
0.8267	Intermediate Similarity	NPC474980
0.8261	Intermediate Similarity	NPC136473
0.8254	Intermediate Similarity	NPC71755
0.8254	Intermediate Similarity	NPC268185
0.8243	Intermediate Similarity	NPC19900
0.8169	Intermediate Similarity	NPC153660
0.8108	Intermediate Similarity	NPC475994
0.7973	Intermediate Similarity	NPC471061
0.7949	Intermediate Similarity	NPC219966
0.7922	Intermediate Similarity	NPC38796
0.7922	Intermediate Similarity	NPC158411
0.7887	Intermediate Similarity	NPC107848
0.7867	Intermediate Similarity	NPC231739
0.7808	Intermediate Similarity	NPC215050
0.7778	Intermediate Similarity	NPC319163
0.7778	Intermediate Similarity	NPC67076
0.7778	Intermediate Similarity	NPC474884
0.7761	Intermediate Similarity	NPC260573
0.7733	Intermediate Similarity	NPC82666
0.7733	Intermediate Similarity	NPC203403
0.7733	Intermediate Similarity	NPC97173
0.7692	Intermediate Similarity	NPC279186
0.7662	Intermediate Similarity	NPC471514
0.7639	Intermediate Similarity	NPC286154
0.7625	Intermediate Similarity	NPC476426
0.7619	Intermediate Similarity	NPC217188
0.7571	Intermediate Similarity	NPC472072
0.7571	Intermediate Similarity	NPC137163
0.7568	Intermediate Similarity	NPC144995
0.7568	Intermediate Similarity	NPC227814
0.7564	Intermediate Similarity	NPC6663
0.7538	Intermediate Similarity	NPC48891
0.7532	Intermediate Similarity	NPC308038
0.7531	Intermediate Similarity	NPC194417
0.75	Intermediate Similarity	NPC230527
0.75	Intermediate Similarity	NPC476007
0.75	Intermediate Similarity	NPC7927
0.747	Intermediate Similarity	NPC87306
0.7467	Intermediate Similarity	NPC166018
0.7467	Intermediate Similarity	NPC474011
0.7467	Intermediate Similarity	NPC169056
0.7467	Intermediate Similarity	NPC474885
0.7467	Intermediate Similarity	NPC225665
0.7465	Intermediate Similarity	NPC96962
0.746	Intermediate Similarity	NPC35756
0.7436	Intermediate Similarity	NPC172013
0.7436	Intermediate Similarity	NPC160582
0.7419	Intermediate Similarity	NPC225974
0.7419	Intermediate Similarity	NPC118788
0.7403	Intermediate Similarity	NPC478122
0.7403	Intermediate Similarity	NPC62336
0.7397	Intermediate Similarity	NPC203819
0.7397	Intermediate Similarity	NPC318766
0.7381	Intermediate Similarity	NPC473455
0.7375	Intermediate Similarity	NPC477785
0.7375	Intermediate Similarity	NPC477786
0.7375	Intermediate Similarity	NPC477784
0.7368	Intermediate Similarity	NPC469646
0.7368	Intermediate Similarity	NPC263582
0.7361	Intermediate Similarity	NPC469679
0.7361	Intermediate Similarity	NPC469688
0.7361	Intermediate Similarity	NPC45264
0.7344	Intermediate Similarity	NPC37644
0.7317	Intermediate Similarity	NPC472974
0.7308	Intermediate Similarity	NPC136033
0.7308	Intermediate Similarity	NPC281138
0.7284	Intermediate Similarity	NPC31086
0.7284	Intermediate Similarity	NPC474865
0.7284	Intermediate Similarity	NPC476412
0.7284	Intermediate Similarity	NPC472326
0.7273	Intermediate Similarity	NPC86917
0.7273	Intermediate Similarity	NPC74995
0.726	Intermediate Similarity	NPC250928
0.726	Intermediate Similarity	NPC236208
0.726	Intermediate Similarity	NPC10758
0.7258	Intermediate Similarity	NPC267110
0.725	Intermediate Similarity	NPC93590
0.7237	Intermediate Similarity	NPC114236
0.7231	Intermediate Similarity	NPC189677
0.7229	Intermediate Similarity	NPC287079
0.7229	Intermediate Similarity	NPC473248
0.7215	Intermediate Similarity	NPC74086
0.7215	Intermediate Similarity	NPC45495
0.72	Intermediate Similarity	NPC215745
0.72	Intermediate Similarity	NPC238948
0.72	Intermediate Similarity	NPC12815
0.72	Intermediate Similarity	NPC275098
0.7195	Intermediate Similarity	NPC179006
0.7195	Intermediate Similarity	NPC474853
0.7179	Intermediate Similarity	NPC279532
0.7179	Intermediate Similarity	NPC192006
0.7164	Intermediate Similarity	NPC283502
0.716	Intermediate Similarity	NPC52923
0.716	Intermediate Similarity	NPC105173
0.7143	Intermediate Similarity	NPC322457
0.7143	Intermediate Similarity	NPC250621
0.7143	Intermediate Similarity	NPC288381
0.7143	Intermediate Similarity	NPC153570
0.7143	Intermediate Similarity	NPC470525
0.7143	Intermediate Similarity	NPC20934
0.7126	Intermediate Similarity	NPC78159
0.7125	Intermediate Similarity	NPC470298
0.7125	Intermediate Similarity	NPC275507
0.7121	Intermediate Similarity	NPC317899
0.7121	Intermediate Similarity	NPC232247
0.7121	Intermediate Similarity	NPC251666
0.7108	Intermediate Similarity	NPC472985
0.7108	Intermediate Similarity	NPC472986
0.7108	Intermediate Similarity	NPC183736
0.7105	Intermediate Similarity	NPC476590
0.7105	Intermediate Similarity	NPC114727
0.7105	Intermediate Similarity	NPC122244
0.7089	Intermediate Similarity	NPC152061
0.7089	Intermediate Similarity	NPC7232
0.7059	Intermediate Similarity	NPC311852
0.7059	Intermediate Similarity	NPC471054
0.7059	Intermediate Similarity	NPC472983
0.7059	Intermediate Similarity	NPC472973
0.7059	Intermediate Similarity	NPC123912
0.7051	Intermediate Similarity	NPC320630
0.7051	Intermediate Similarity	NPC262747
0.7051	Intermediate Similarity	NPC197659
0.7051	Intermediate Similarity	NPC116177
0.7051	Intermediate Similarity	NPC7563
0.7045	Intermediate Similarity	NPC214694
0.7042	Intermediate Similarity	NPC150162
0.7037	Intermediate Similarity	NPC145963
0.7027	Intermediate Similarity	NPC471560
0.7027	Intermediate Similarity	NPC143396
0.7027	Intermediate Similarity	NPC475982
0.7027	Intermediate Similarity	NPC476059
0.7027	Intermediate Similarity	NPC473603
0.7024	Intermediate Similarity	NPC241054
0.7015	Intermediate Similarity	NPC472808
0.7015	Intermediate Similarity	NPC324224
0.7013	Intermediate Similarity	NPC476346
0.7011	Intermediate Similarity	NPC474736
0.7	Intermediate Similarity	NPC294304
0.7	Intermediate Similarity	NPC271104
0.7	Intermediate Similarity	NPC228574
0.7	Intermediate Similarity	NPC157895
0.7	Intermediate Similarity	NPC104120
0.7	Intermediate Similarity	NPC148685
0.7	Intermediate Similarity	NPC64985
0.7	Intermediate Similarity	NPC91332
0.7	Intermediate Similarity	NPC162741
0.6988	Remote Similarity	NPC187529
0.6988	Remote Similarity	NPC474860
0.6988	Remote Similarity	NPC15807
0.6988	Remote Similarity	NPC471300
0.6988	Remote Similarity	NPC255174
0.6988	Remote Similarity	NPC28887
0.6986	Remote Similarity	NPC254886
0.6974	Remote Similarity	NPC247586
0.697	Remote Similarity	NPC474127
0.6962	Remote Similarity	NPC108816
0.6962	Remote Similarity	NPC93763
0.6962	Remote Similarity	NPC275494
0.6962	Remote Similarity	NPC297996
0.6962	Remote Similarity	NPC471409
0.6962	Remote Similarity	NPC267231
0.6962	Remote Similarity	NPC474816
0.6962	Remote Similarity	NPC209135
0.6957	Remote Similarity	NPC278202
0.6957	Remote Similarity	NPC322002
0.6951	Remote Similarity	NPC161045
0.6951	Remote Similarity	NPC16488
0.6951	Remote Similarity	NPC251475
0.6951	Remote Similarity	NPC62214
0.6951	Remote Similarity	NPC169941
0.6944	Remote Similarity	NPC474329
0.6944	Remote Similarity	NPC474304
0.6941	Remote Similarity	NPC106051
0.6941	Remote Similarity	NPC471791
0.6941	Remote Similarity	NPC471793
0.6941	Remote Similarity	NPC472011
0.6941	Remote Similarity	NPC474854
0.6933	Remote Similarity	NPC173321
0.6923	Remote Similarity	NPC51391
0.6923	Remote Similarity	NPC16279
0.6923	Remote Similarity	NPC203277
0.6923	Remote Similarity	NPC27205
0.6923	Remote Similarity	NPC205615
0.6923	Remote Similarity	NPC4492
0.6923	Remote Similarity	NPC474197
0.6923	Remote Similarity	NPC256640
0.6914	Remote Similarity	NPC136150
0.6914	Remote Similarity	NPC116797
0.6905	Remote Similarity	NPC196381
0.6905	Remote Similarity	NPC316426
0.6905	Remote Similarity	NPC315395
0.6905	Remote Similarity	NPC94666

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 NPC106613 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	2049
0.2-0.3	4426
0.3-0.4	1911
0.4-0.5	351
0.5-0.6	237
0.6-0.7	39
0.7-0.8	2
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
0.7215	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6110	Phase 1
0.6962	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7331	Phase 2
0.6786	Remote Similarity	NPD1696	Phase 3
0.6786	Remote Similarity	NPD5363	Approved
0.6782	Remote Similarity	NPD5785	Approved
0.6765	Remote Similarity	NPD4219	Approved
0.6761	Remote Similarity	NPD4194	Approved
0.6761	Remote Similarity	NPD368	Approved
0.6761	Remote Similarity	NPD4193	Approved
0.6761	Remote Similarity	NPD4192	Approved
0.6761	Remote Similarity	NPD4191	Approved
0.6706	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD3666	Approved
0.6618	Remote Similarity	NPD342	Phase 1
0.6585	Remote Similarity	NPD4252	Approved
0.6582	Remote Similarity	NPD8264	Approved
0.6538	Remote Similarity	NPD4732	Discontinued
0.6517	Remote Similarity	NPD6079	Approved
0.6512	Remote Similarity	NPD4623	Approved
0.6512	Remote Similarity	NPD4519	Discontinued
0.6512	Remote Similarity	NPD5279	Phase 3
0.6508	Remote Similarity	NPD4265	Approved
0.6471	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3667	Approved
0.6429	Remote Similarity	NPD4269	Approved
0.6429	Remote Similarity	NPD5209	Approved
0.6429	Remote Similarity	NPD4270	Approved
0.642	Remote Similarity	NPD4756	Discovery
0.6395	Remote Similarity	NPD1694	Approved
0.6386	Remote Similarity	NPD4695	Discontinued
0.6377	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4268	Approved
0.6341	Remote Similarity	NPD4271	Approved
0.6316	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4629	Approved
0.6304	Remote Similarity	NPD5210	Approved
0.6292	Remote Similarity	NPD5328	Approved
0.6279	Remote Similarity	NPD4786	Approved
0.6267	Remote Similarity	NPD7341	Phase 2
0.625	Remote Similarity	NPD5211	Phase 2
0.6237	Remote Similarity	NPD5222	Approved
0.6237	Remote Similarity	NPD5221	Approved
0.6237	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4819	Approved
0.619	Remote Similarity	NPD4822	Approved
0.619	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4820	Approved
0.619	Remote Similarity	NPD4821	Approved
0.6184	Remote Similarity	NPD3704	Approved
0.6184	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD8039	Approved
0.617	Remote Similarity	NPD5173	Approved
0.6163	Remote Similarity	NPD5331	Approved
0.6163	Remote Similarity	NPD7154	Phase 3
0.6163	Remote Similarity	NPD5332	Approved
0.6163	Remote Similarity	NPD5362	Discontinued
0.6154	Remote Similarity	NPD7515	Phase 2
0.6145	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5690	Phase 2
0.6136	Remote Similarity	NPD5786	Approved
0.6129	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5141	Approved
0.6118	Remote Similarity	NPD4790	Discontinued
0.6111	Remote Similarity	NPD4753	Phase 2
0.6111	Remote Similarity	NPD287	Approved
0.6105	Remote Similarity	NPD4225	Approved
0.6087	Remote Similarity	NPD4202	Approved
0.6076	Remote Similarity	NPD4691	Approved
0.6071	Remote Similarity	NPD4195	Approved
0.6064	Remote Similarity	NPD4697	Phase 3
0.6053	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD4058	Approved
0.6047	Remote Similarity	NPD4221	Approved
0.6047	Remote Similarity	NPD4223	Phase 3
0.6042	Remote Similarity	NPD5285	Approved
0.6042	Remote Similarity	NPD4696	Approved
0.6042	Remote Similarity	NPD5286	Approved
0.6022	Remote Similarity	NPD5282	Discontinued
0.6	Remote Similarity	NPD4222	Approved
0.6	Remote Similarity	NPD7332	Phase 2
0.6	Remote Similarity	NPD7514	Phase 3
0.5979	Remote Similarity	NPD5223	Approved
0.5978	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD7637	Suspended
0.5972	Remote Similarity	NPD8779	Phase 3
0.597	Remote Similarity	NPD4220	Pre-registration
0.597	Remote Similarity	NPD3173	Approved
0.5955	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7145	Approved
0.5949	Remote Similarity	NPD4137	Phase 3
0.5938	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5370	Suspended
0.593	Remote Similarity	NPD6902	Approved
0.593	Remote Similarity	NPD5369	Approved
0.5921	Remote Similarity	NPD3197	Phase 1
0.5921	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5226	Approved
0.5918	Remote Similarity	NPD4633	Approved
0.5918	Remote Similarity	NPD5224	Approved
0.5918	Remote Similarity	NPD5225	Approved
0.5914	Remote Similarity	NPD5778	Approved
0.5914	Remote Similarity	NPD5779	Approved
0.5909	Remote Similarity	NPD4197	Approved
0.5876	Remote Similarity	NPD7639	Approved
0.5876	Remote Similarity	NPD7640	Approved
0.5875	Remote Similarity	NPD7144	Approved
0.5875	Remote Similarity	NPD4747	Approved
0.5875	Remote Similarity	NPD7143	Approved
0.587	Remote Similarity	NPD6698	Approved
0.587	Remote Similarity	NPD46	Approved
0.5862	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5175	Approved
0.5859	Remote Similarity	NPD5174	Approved
0.5859	Remote Similarity	NPD6647	Phase 2
0.5854	Remote Similarity	NPD4687	Approved
0.5851	Remote Similarity	NPD7748	Approved
0.5843	Remote Similarity	NPD5329	Approved
0.5833	Remote Similarity	NPD6925	Approved
0.5833	Remote Similarity	NPD4755	Approved
0.5833	Remote Similarity	NPD7902	Approved
0.5833	Remote Similarity	NPD5776	Phase 2
0.5824	Remote Similarity	NPD4518	Approved
0.5814	Remote Similarity	NPD5368	Approved
0.5806	Remote Similarity	NPD5281	Approved
0.5806	Remote Similarity	NPD6411	Approved
0.5806	Remote Similarity	NPD5284	Approved
0.5802	Remote Similarity	NPD5276	Approved
0.5802	Remote Similarity	NPD7152	Approved
0.5802	Remote Similarity	NPD7151	Approved
0.5802	Remote Similarity	NPD7150	Approved
0.5794	Remote Similarity	NPD7115	Discovery
0.5778	Remote Similarity	NPD5280	Approved
0.5778	Remote Similarity	NPD4689	Approved
0.5778	Remote Similarity	NPD4688	Approved
0.5778	Remote Similarity	NPD7521	Approved
0.5778	Remote Similarity	NPD4693	Phase 3
0.5778	Remote Similarity	NPD6684	Approved
0.5778	Remote Similarity	NPD4690	Approved
0.5778	Remote Similarity	NPD4249	Approved
0.5778	Remote Similarity	NPD5205	Approved
0.5778	Remote Similarity	NPD4138	Approved
0.5778	Remote Similarity	NPD7146	Approved
0.5778	Remote Similarity	NPD7334	Approved
0.5778	Remote Similarity	NPD4694	Approved
0.5778	Remote Similarity	NPD6409	Approved
0.5778	Remote Similarity	NPD5330	Approved
0.5773	Remote Similarity	NPD7638	Approved
0.5765	Remote Similarity	NPD3617	Approved
0.5758	Remote Similarity	NPD39	Approved
0.575	Remote Similarity	NPD6922	Approved
0.575	Remote Similarity	NPD6923	Approved
0.5745	Remote Similarity	NPD6399	Phase 3
0.573	Remote Similarity	NPD3668	Phase 3
0.5714	Remote Similarity	NPD4251	Approved
0.5714	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4700	Approved
0.5714	Remote Similarity	NPD4250	Approved
0.5699	Remote Similarity	NPD7838	Discovery
0.5698	Remote Similarity	NPD6929	Approved
0.5686	Remote Similarity	NPD5697	Approved
0.5682	Remote Similarity	NPD6435	Approved
0.5676	Remote Similarity	NPD6109	Phase 1
0.5673	Remote Similarity	NPD6371	Approved
0.567	Remote Similarity	NPD6084	Phase 2
0.567	Remote Similarity	NPD6083	Phase 2
0.5667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD5733	Approved
0.5663	Remote Similarity	NPD6926	Approved
0.5663	Remote Similarity	NPD6924	Approved
0.5652	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6903	Approved
0.5647	Remote Similarity	NPD6932	Approved
0.5638	Remote Similarity	NPD7983	Approved
0.5634	Remote Similarity	NPD3172	Approved
0.5632	Remote Similarity	NPD6931	Approved
0.5632	Remote Similarity	NPD6930	Phase 2
0.5631	Remote Similarity	NPD6899	Approved
0.5631	Remote Similarity	NPD6011	Approved
0.5631	Remote Similarity	NPD4729	Approved
0.5631	Remote Similarity	NPD4730	Approved
0.5631	Remote Similarity	NPD6881	Approved
0.5631	Remote Similarity	NPD5168	Approved
0.5625	Remote Similarity	NPD5695	Phase 3
0.5619	Remote Similarity	NPD6650	Approved
0.5619	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6649	Approved
0.5618	Remote Similarity	NPD4788	Approved
0.5612	Remote Similarity	NPD5696	Approved
0.5612	Remote Similarity	NPD5290	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