NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.17
Volume:	243.025
LogP:	4.183
LogD:	3.695
LogS:	-3.973
# Rotatable Bonds:	2
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.623
Synthetic Accessibility Score:	2.908
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.648
MDCK Permeability:	1.5408297258545645e-05
Pgp-inhibitor:	0.946
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.885
30% Bioavailability (F30%):	0.189

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	93.34952545166016%
Volume Distribution (VD):	2.274
Pgp-substrate:	9.666082382202148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.792
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.718
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.396
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.859
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.416

ADMET: Excretion

Clearance (CL):	2.213
Half-life (T1/2):	0.456

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.105
Drug-inuced Liver Injury (DILI):	0.126
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.271
Maximum Recommended Daily Dose:	0.354
Skin Sensitization:	0.742
Carcinogencity:	0.382
Eye Corrosion:	0.762
Eye Irritation:	0.805
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC23117

Natural Product ID:	NPC23117
*Common Name:**	(E)-3-Methyl-4-(2,6,6-Trimethylcyclohex-2-En-1-Yl)But-3-En-2-One
IUPAC Name:	(E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
Synonyms:
Standard InCHIKey:	JRJBVWJSTHECJK-PKNBQFBNSA-N
Standard InCHI:	InChI=1S/C14H22O/c1-10-7-6-8-14(4,5)13(10)9-11(2)12(3)15/h7,9,13H,6,8H2,1-5H3/b11-9+
SMILES:	CC1=CCCC(C1/C=C(/C(=O)C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3183353
PubChem CID:	5372174
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[17628872]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19370929]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22080044]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[7779269]
NPO1918	Magnolia kobus	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1918	Magnolia kobus	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1918	Magnolia kobus	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15294	Magnolia salicifolia	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15064	Magnolia denudata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18811	Magnolia biondii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1918	Magnolia kobus	Species	Magnoliaceae	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	3
Potency	2

Activity Type	# Activity
Individual Protein	2
Others	1
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT603	Individual Protein	Olfactory receptor 5K1	Homo sapiens	Inhibition	>=	50.0	%	PMID[540511]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	1096.2	nM	PubChem BioAssay data set
NPT21312	SINGLE PROTEIN	Diacylglycerol O-acyltransferase 1	Bos taurus	Inhibition	=	21.0	%	PMID[540512]
NPT21313	SINGLE PROTEIN	Lecithin retinol acyltransferase	Bos taurus	Inhibition	=	38.0	%	PMID[540512]
NPT2	Others	Unspecified		Potency	n.a.	12299.8	nM	PubChem BioAssay data set

☑ 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 NPC23117 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	217
0.1-0.2	4436
0.2-0.3	19698
0.3-0.4	10403
0.4-0.5	5823
0.5-0.6	1677
0.6-0.7	345
0.7-0.8	76
0.8-0.85	11
0.85-0.9	8
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC14002
0.9412	High Similarity	NPC5626
0.9074	High Similarity	NPC311852
0.8462	Intermediate Similarity	NPC64866
0.8421	Intermediate Similarity	NPC127582
0.8393	Intermediate Similarity	NPC308108
0.8393	Intermediate Similarity	NPC60772
0.8393	Intermediate Similarity	NPC170799
0.8305	Intermediate Similarity	NPC212210
0.8276	Intermediate Similarity	NPC213152
0.8269	Intermediate Similarity	NPC176819
0.8269	Intermediate Similarity	NPC228776
0.8269	Intermediate Similarity	NPC163984
0.8269	Intermediate Similarity	NPC58970
0.8269	Intermediate Similarity	NPC32351
0.8148	Intermediate Similarity	NPC69898
0.8148	Intermediate Similarity	NPC295777
0.8148	Intermediate Similarity	NPC268564
0.8148	Intermediate Similarity	NPC37644
0.8136	Intermediate Similarity	NPC288253
0.8	Intermediate Similarity	NPC285371
0.8	Intermediate Similarity	NPC475124
0.8	Intermediate Similarity	NPC6697
0.7931	Intermediate Similarity	NPC472304
0.7931	Intermediate Similarity	NPC276764
0.7925	Intermediate Similarity	NPC118788
0.7903	Intermediate Similarity	NPC475523
0.7869	Intermediate Similarity	NPC251118
0.7843	Intermediate Similarity	NPC166788
0.7833	Intermediate Similarity	NPC165695
0.78	Intermediate Similarity	NPC216921
0.7778	Intermediate Similarity	NPC188292
0.7778	Intermediate Similarity	NPC310992
0.7778	Intermediate Similarity	NPC87141
0.7778	Intermediate Similarity	NPC155198
0.7778	Intermediate Similarity	NPC260474
0.7759	Intermediate Similarity	NPC27610
0.7759	Intermediate Similarity	NPC56905
0.7742	Intermediate Similarity	NPC176171
0.7742	Intermediate Similarity	NPC92327
0.7719	Intermediate Similarity	NPC473733
0.7692	Intermediate Similarity	NPC8610
0.7692	Intermediate Similarity	NPC262558
0.7656	Intermediate Similarity	NPC256846
0.7627	Intermediate Similarity	NPC96551
0.7627	Intermediate Similarity	NPC285594
0.7619	Intermediate Similarity	NPC176107
0.7586	Intermediate Similarity	NPC115385
0.7581	Intermediate Similarity	NPC470329
0.7547	Intermediate Similarity	NPC91962
0.7541	Intermediate Similarity	NPC32285
0.7541	Intermediate Similarity	NPC202118
0.7541	Intermediate Similarity	NPC197238
0.7538	Intermediate Similarity	NPC2634
0.7538	Intermediate Similarity	NPC251929
0.7538	Intermediate Similarity	NPC265782
0.75	Intermediate Similarity	NPC25853
0.75	Intermediate Similarity	NPC117804
0.75	Intermediate Similarity	NPC191337
0.75	Intermediate Similarity	NPC296311
0.7458	Intermediate Similarity	NPC30215
0.7458	Intermediate Similarity	NPC94991
0.7458	Intermediate Similarity	NPC266295
0.7424	Intermediate Similarity	NPC54123
0.7424	Intermediate Similarity	NPC474562
0.7419	Intermediate Similarity	NPC52449
0.7419	Intermediate Similarity	NPC469662
0.7419	Intermediate Similarity	NPC169275
0.7385	Intermediate Similarity	NPC136473
0.7385	Intermediate Similarity	NPC139397
0.7377	Intermediate Similarity	NPC60565
0.7358	Intermediate Similarity	NPC236355
0.7358	Intermediate Similarity	NPC14917
0.7358	Intermediate Similarity	NPC4079
0.7344	Intermediate Similarity	NPC4370
0.7344	Intermediate Similarity	NPC290350
0.7333	Intermediate Similarity	NPC259261
0.7313	Intermediate Similarity	NPC276336
0.7313	Intermediate Similarity	NPC470044
0.7313	Intermediate Similarity	NPC474228
0.7313	Intermediate Similarity	NPC251705
0.7313	Intermediate Similarity	NPC470045
0.7313	Intermediate Similarity	NPC303613
0.7308	Intermediate Similarity	NPC25771
0.7308	Intermediate Similarity	NPC477686
0.7288	Intermediate Similarity	NPC321568
0.7288	Intermediate Similarity	NPC192427
0.7288	Intermediate Similarity	NPC281986
0.7288	Intermediate Similarity	NPC22019
0.7288	Intermediate Similarity	NPC208749
0.7273	Intermediate Similarity	NPC260040
0.7273	Intermediate Similarity	NPC307176
0.7273	Intermediate Similarity	NPC282593
0.7273	Intermediate Similarity	NPC159577
0.7273	Intermediate Similarity	NPC35734
0.7273	Intermediate Similarity	NPC116906
0.7241	Intermediate Similarity	NPC200258
0.7206	Intermediate Similarity	NPC309852
0.72	Intermediate Similarity	NPC111474
0.717	Intermediate Similarity	NPC13991
0.717	Intermediate Similarity	NPC114239
0.717	Intermediate Similarity	NPC86683
0.717	Intermediate Similarity	NPC241784
0.7164	Intermediate Similarity	NPC95863
0.7164	Intermediate Similarity	NPC5701
0.7164	Intermediate Similarity	NPC190035
0.7164	Intermediate Similarity	NPC21944
0.7164	Intermediate Similarity	NPC225467
0.7164	Intermediate Similarity	NPC234707
0.7164	Intermediate Similarity	NPC115023
0.7143	Intermediate Similarity	NPC236623
0.7143	Intermediate Similarity	NPC4638
0.7143	Intermediate Similarity	NPC27438
0.7115	Intermediate Similarity	NPC301972
0.7115	Intermediate Similarity	NPC292463
0.7101	Intermediate Similarity	NPC476346
0.7101	Intermediate Similarity	NPC293803
0.7097	Intermediate Similarity	NPC475795
0.7097	Intermediate Similarity	NPC97322
0.7069	Intermediate Similarity	NPC209431
0.7069	Intermediate Similarity	NPC100809
0.7059	Intermediate Similarity	NPC180015
0.7059	Intermediate Similarity	NPC109576
0.7059	Intermediate Similarity	NPC153660
0.7059	Intermediate Similarity	NPC186042
0.7059	Intermediate Similarity	NPC130016
0.7059	Intermediate Similarity	NPC56747
0.7018	Intermediate Similarity	NPC471751
0.7015	Intermediate Similarity	NPC246722
0.7015	Intermediate Similarity	NPC151045
0.7	Intermediate Similarity	NPC55004
0.7	Intermediate Similarity	NPC217923
0.7	Intermediate Similarity	NPC267626
0.7	Intermediate Similarity	NPC474463
0.7	Intermediate Similarity	NPC193695
0.7	Intermediate Similarity	NPC49575
0.7	Intermediate Similarity	NPC470525
0.7	Intermediate Similarity	NPC230823
0.7	Intermediate Similarity	NPC69408
0.7	Intermediate Similarity	NPC26504
0.7	Intermediate Similarity	NPC1254
0.6984	Remote Similarity	NPC167256
0.6984	Remote Similarity	NPC472306
0.697	Remote Similarity	NPC296697
0.697	Remote Similarity	NPC39157
0.697	Remote Similarity	NPC142754
0.697	Remote Similarity	NPC20610
0.697	Remote Similarity	NPC82477
0.6964	Remote Similarity	NPC15325
0.6957	Remote Similarity	NPC474796
0.6957	Remote Similarity	NPC329866
0.6957	Remote Similarity	NPC255021
0.6957	Remote Similarity	NPC474797
0.6957	Remote Similarity	NPC20025
0.6957	Remote Similarity	NPC215050
0.6949	Remote Similarity	NPC275472
0.6923	Remote Similarity	NPC242945
0.6923	Remote Similarity	NPC323005
0.6923	Remote Similarity	NPC259156
0.6912	Remote Similarity	NPC133253
0.6912	Remote Similarity	NPC304983
0.6912	Remote Similarity	NPC305501
0.6912	Remote Similarity	NPC474539
0.6912	Remote Similarity	NPC181204
0.6901	Remote Similarity	NPC97377
0.6897	Remote Similarity	NPC474141
0.6897	Remote Similarity	NPC45283
0.6875	Remote Similarity	NPC473902
0.6875	Remote Similarity	NPC150162
0.6866	Remote Similarity	NPC182815
0.6866	Remote Similarity	NPC286814
0.6857	Remote Similarity	NPC114236
0.6857	Remote Similarity	NPC65650
0.6857	Remote Similarity	NPC473171
0.6852	Remote Similarity	NPC296337
0.6833	Remote Similarity	NPC20603
0.6825	Remote Similarity	NPC294304
0.6825	Remote Similarity	NPC228574
0.6818	Remote Similarity	NPC20181
0.6818	Remote Similarity	NPC220210
0.6812	Remote Similarity	NPC29542
0.6812	Remote Similarity	NPC323437
0.6812	Remote Similarity	NPC201562
0.6806	Remote Similarity	NPC189485
0.6806	Remote Similarity	NPC74410
0.6806	Remote Similarity	NPC62336
0.6806	Remote Similarity	NPC115515
0.6806	Remote Similarity	NPC475994
0.6786	Remote Similarity	NPC145311
0.6786	Remote Similarity	NPC17518
0.678	Remote Similarity	NPC63396
0.678	Remote Similarity	NPC202850
0.678	Remote Similarity	NPC250539
0.6774	Remote Similarity	NPC143834
0.6769	Remote Similarity	NPC107258
0.6761	Remote Similarity	NPC469796
0.6761	Remote Similarity	NPC250621
0.6761	Remote Similarity	NPC263582
0.6761	Remote Similarity	NPC469793
0.6761	Remote Similarity	NPC180886

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 NPC23117 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	3817
0.2-0.3	3921
0.3-0.4	800
0.4-0.5	304
0.5-0.6	75
0.6-0.7	14
0.7-0.8	1
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
0.8393	Intermediate Similarity	NPD287	Approved
0.7538	Intermediate Similarity	NPD4691	Approved
0.7385	Intermediate Similarity	NPD4137	Phase 3
0.7273	Intermediate Similarity	NPD4747	Approved
0.7206	Intermediate Similarity	NPD4058	Approved
0.7164	Intermediate Similarity	NPD5276	Approved
0.697	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5733	Approved
0.6957	Remote Similarity	NPD4687	Approved
0.6622	Remote Similarity	NPD4695	Discontinued
0.66	Remote Similarity	NPD319	Phase 1
0.6562	Remote Similarity	NPD4193	Approved
0.6562	Remote Similarity	NPD4192	Approved
0.6562	Remote Similarity	NPD4191	Approved
0.6562	Remote Similarity	NPD4194	Approved
0.6486	Remote Similarity	NPD4195	Approved
0.6364	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5783	Phase 3
0.6316	Remote Similarity	NPD8028	Phase 2
0.6296	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD4223	Phase 3
0.6234	Remote Similarity	NPD4221	Approved
0.6176	Remote Similarity	NPD7331	Phase 2
0.6125	Remote Similarity	NPD5690	Phase 2
0.6076	Remote Similarity	NPD3133	Approved
0.6076	Remote Similarity	NPD3666	Approved
0.6076	Remote Similarity	NPD4197	Approved
0.6076	Remote Similarity	NPD3665	Phase 1
0.6049	Remote Similarity	NPD3573	Approved
0.6032	Remote Similarity	NPD4219	Approved
0.6	Remote Similarity	NPD5329	Approved
0.5932	Remote Similarity	NPD8262	Approved
0.5926	Remote Similarity	NPD3618	Phase 1
0.5926	Remote Similarity	NPD5205	Approved
0.5926	Remote Similarity	NPD4688	Approved
0.5926	Remote Similarity	NPD5279	Phase 3
0.5926	Remote Similarity	NPD5280	Approved
0.5926	Remote Similarity	NPD7521	Approved
0.5926	Remote Similarity	NPD6684	Approved
0.5926	Remote Similarity	NPD4138	Approved
0.5926	Remote Similarity	NPD7334	Approved
0.5926	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4623	Approved
0.5926	Remote Similarity	NPD7146	Approved
0.5926	Remote Similarity	NPD4693	Phase 3
0.5926	Remote Similarity	NPD5330	Approved
0.5926	Remote Similarity	NPD4689	Approved
0.5926	Remote Similarity	NPD4690	Approved
0.5926	Remote Similarity	NPD6409	Approved
0.5926	Remote Similarity	NPD4694	Approved
0.5926	Remote Similarity	NPD4519	Discontinued
0.5921	Remote Similarity	NPD3617	Approved
0.5882	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD3667	Approved
0.5823	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD1696	Phase 3
0.5797	Remote Similarity	NPD7341	Phase 2
0.5783	Remote Similarity	NPD5737	Approved
0.5783	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD6903	Approved
0.5783	Remote Similarity	NPD6672	Approved
0.5783	Remote Similarity	NPD5208	Approved
0.5769	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD6079	Approved
0.5753	Remote Similarity	NPD4243	Approved
0.5735	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5328	Approved
0.5714	Remote Similarity	NPD6904	Approved
0.5714	Remote Similarity	NPD6673	Approved
0.5714	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6080	Approved
0.5714	Remote Similarity	NPD4753	Phase 2
0.5692	Remote Similarity	NPD8779	Phase 3
0.5679	Remote Similarity	NPD4786	Approved
0.5679	Remote Similarity	NPD3668	Phase 3
0.5647	Remote Similarity	NPD5692	Phase 3
0.5647	Remote Similarity	NPD4096	Approved
0.5647	Remote Similarity	NPD5207	Approved
0.5634	Remote Similarity	NPD3709	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5209	Approved
0.5625	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD342	Phase 1
0.561	Remote Similarity	NPD1694	Approved
0.56	Remote Similarity	NPD4785	Approved
0.56	Remote Similarity	NPD4784	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