NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	204.15
Volume:	240.388
LogP:	3.824
LogD:	3.798
LogS:	-4.223
# Rotatable Bonds:	4
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	2.49
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.52
MDCK Permeability:	1.6689527910784818e-05
Pgp-inhibitor:	0.5
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.252
30% Bioavailability (F30%):	0.145

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.826
Plasma Protein Binding (PPB):	68.85712432861328%
Volume Distribution (VD):	3.771
Pgp-substrate:	26.07027244567871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.681
CYP1A2-substrate:	0.871
CYP2C19-inhibitor:	0.727
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.379
CYP2C9-substrate:	0.685
CYP2D6-inhibitor:	0.868
CYP2D6-substrate:	0.784
CYP3A4-inhibitor:	0.365
CYP3A4-substrate:	0.643

ADMET: Excretion

Clearance (CL):	7.615
Half-life (T1/2):	0.273

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.03
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.118
Skin Sensitization:	0.967
Carcinogencity:	0.104
Eye Corrosion:	0.971
Eye Irritation:	0.992
Respiratory Toxicity:	0.129

Download Data

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

Natural Product: NPC230068

Natural Product ID:	NPC230068
*Common Name:**	3-(4-Tert-Butylphenyl)-2-Methylpropanal
IUPAC Name:	3-(4-tert-butylphenyl)-2-methylpropanal
Synonyms:
Standard InCHIKey:	SDQFDHOLCGWZPU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H20O/c1-11(10-15)9-12-5-7-13(8-6-12)14(2,3)4/h5-8,10-11H,9H2,1-4H3
SMILES:	O=CC(Cc1ccc(cc1)C(C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1496715
PubChem CID:	228987
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*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
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19048	Pinellia ternata	Species	Araceae	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	2
Potency	33

Activity Type	# Activity
Individual Protein	13
Others	22

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	39810.7	nM	PMID[554333]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	10.0	nM	PMID[554333]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[554333]
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	562.3	nM	PMID[554333]
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	6.3	nM	PMID[554334]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	74978.0	nM	PMID[554333]
NPT103	Individual Protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	94391.8	nM	PMID[554333]
NPT603	Individual Protein	Olfactory receptor 5K1	Homo sapiens	Inhibition	>=	50.0	%	PMID[554335]
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	61622.2	nM	PubChem BioAssay data set
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	13802.2	nM	PubChem BioAssay data set
NPT98	Individual Protein	HERG	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[554333]
NPT813	Individual Protein	GABA transporter 1	Mus musculus	Activity	=	91.0	%	PMID[554336]
NPT2	Others	Unspecified		Potency	n.a.	61068.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	10963.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48918.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54427.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43277.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68519.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	109.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21864.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61622.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	13671.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48972.2	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 NPC230068 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	260
0.1-0.2	1479
0.2-0.3	4768
0.3-0.4	17195
0.4-0.5	15156
0.5-0.6	3157
0.6-0.7	520
0.7-0.8	138
0.8-0.85	10
0.85-0.9	11
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9737	High Similarity	NPC157055
0.9342	High Similarity	NPC298023
0.8974	High Similarity	NPC103488
0.8941	High Similarity	NPC125226
0.8902	High Similarity	NPC252067
0.8824	High Similarity	NPC58872
0.8816	High Similarity	NPC271437
0.875	High Similarity	NPC285716
0.875	High Similarity	NPC17408
0.8734	High Similarity	NPC137847
0.8734	High Similarity	NPC76455
0.8701	High Similarity	NPC208075
0.8659	High Similarity	NPC197581
0.8608	High Similarity	NPC329318
0.8415	Intermediate Similarity	NPC100039
0.8372	Intermediate Similarity	NPC153308
0.8353	Intermediate Similarity	NPC164526
0.8276	Intermediate Similarity	NPC298115
0.8214	Intermediate Similarity	NPC39600
0.8205	Intermediate Similarity	NPC74458
0.8101	Intermediate Similarity	NPC285679
0.8026	Intermediate Similarity	NPC178527
0.7976	Intermediate Similarity	NPC145053
0.7975	Intermediate Similarity	NPC326200
0.7927	Intermediate Similarity	NPC9796
0.7895	Intermediate Similarity	NPC198023
0.7889	Intermediate Similarity	NPC103346
0.7857	Intermediate Similarity	NPC477703
0.7857	Intermediate Similarity	NPC190567
0.7849	Intermediate Similarity	NPC226041
0.7805	Intermediate Similarity	NPC78500
0.7802	Intermediate Similarity	NPC323420
0.7778	Intermediate Similarity	NPC70940
0.7778	Intermediate Similarity	NPC274455
0.7778	Intermediate Similarity	NPC86670
0.7765	Intermediate Similarity	NPC73978
0.7763	Intermediate Similarity	NPC88566
0.7742	Intermediate Similarity	NPC185208
0.7742	Intermediate Similarity	NPC219573
0.7738	Intermediate Similarity	NPC272260
0.7727	Intermediate Similarity	NPC160339
0.7727	Intermediate Similarity	NPC307
0.7722	Intermediate Similarity	NPC16190
0.7722	Intermediate Similarity	NPC235059
0.7722	Intermediate Similarity	NPC169222
0.7692	Intermediate Similarity	NPC133461
0.7684	Intermediate Similarity	NPC221825
0.7667	Intermediate Similarity	NPC325709
0.766	Intermediate Similarity	NPC239185
0.764	Intermediate Similarity	NPC69057
0.7632	Intermediate Similarity	NPC29680
0.7619	Intermediate Similarity	NPC36342
0.7619	Intermediate Similarity	NPC2785
0.7619	Intermediate Similarity	NPC285470
0.7609	Intermediate Similarity	NPC59677
0.7609	Intermediate Similarity	NPC153885
0.76	Intermediate Similarity	NPC470252
0.7579	Intermediate Similarity	NPC75724
0.7579	Intermediate Similarity	NPC134882
0.7529	Intermediate Similarity	NPC151405
0.7529	Intermediate Similarity	NPC300205
0.7529	Intermediate Similarity	NPC139901
0.7527	Intermediate Similarity	NPC238219
0.75	Intermediate Similarity	NPC245966
0.75	Intermediate Similarity	NPC248705
0.75	Intermediate Similarity	NPC135924
0.75	Intermediate Similarity	NPC54368
0.7475	Intermediate Similarity	NPC471186
0.7474	Intermediate Similarity	NPC265220
0.7473	Intermediate Similarity	NPC231591
0.7447	Intermediate Similarity	NPC260233
0.7444	Intermediate Similarity	NPC322387
0.7442	Intermediate Similarity	NPC164086
0.7442	Intermediate Similarity	NPC95868
0.7436	Intermediate Similarity	NPC155172
0.7436	Intermediate Similarity	NPC32312
0.7423	Intermediate Similarity	NPC133809
0.7423	Intermediate Similarity	NPC136810
0.7423	Intermediate Similarity	NPC128248
0.7423	Intermediate Similarity	NPC476993
0.7423	Intermediate Similarity	NPC473325
0.7423	Intermediate Similarity	NPC225079
0.7423	Intermediate Similarity	NPC109514
0.7419	Intermediate Similarity	NPC1682
0.7419	Intermediate Similarity	NPC188844
0.7419	Intermediate Similarity	NPC155232
0.7416	Intermediate Similarity	NPC294134
0.7407	Intermediate Similarity	NPC95289
0.74	Intermediate Similarity	NPC94751
0.74	Intermediate Similarity	NPC142326
0.7391	Intermediate Similarity	NPC67585
0.7391	Intermediate Similarity	NPC277277
0.7391	Intermediate Similarity	NPC110420
0.7391	Intermediate Similarity	NPC303967
0.7391	Intermediate Similarity	NPC173413
0.7386	Intermediate Similarity	NPC270507
0.7386	Intermediate Similarity	NPC288903
0.7386	Intermediate Similarity	NPC44830
0.7363	Intermediate Similarity	NPC157778
0.7356	Intermediate Similarity	NPC273033
0.7356	Intermediate Similarity	NPC12936
0.7312	Intermediate Similarity	NPC284475
0.7312	Intermediate Similarity	NPC86987
0.7308	Intermediate Similarity	NPC45756
0.7303	Intermediate Similarity	NPC267704
0.7294	Intermediate Similarity	NPC249018
0.7294	Intermediate Similarity	NPC3190
0.7284	Intermediate Similarity	NPC98880
0.7273	Intermediate Similarity	NPC323103
0.7273	Intermediate Similarity	NPC103387
0.7273	Intermediate Similarity	NPC210849
0.7253	Intermediate Similarity	NPC43945
0.725	Intermediate Similarity	NPC267443
0.725	Intermediate Similarity	NPC6107
0.7245	Intermediate Similarity	NPC264728
0.7241	Intermediate Similarity	NPC71664
0.7241	Intermediate Similarity	NPC127343
0.7237	Intermediate Similarity	NPC8235
0.7229	Intermediate Similarity	NPC54269
0.7216	Intermediate Similarity	NPC49994
0.7216	Intermediate Similarity	NPC120393
0.7209	Intermediate Similarity	NPC224544
0.7204	Intermediate Similarity	NPC84288
0.7191	Intermediate Similarity	NPC149263
0.7191	Intermediate Similarity	NPC273758
0.7188	Intermediate Similarity	NPC469893
0.7174	Intermediate Similarity	NPC267262
0.716	Intermediate Similarity	NPC311343
0.7158	Intermediate Similarity	NPC289883
0.7128	Intermediate Similarity	NPC475059
0.7128	Intermediate Similarity	NPC220596
0.7128	Intermediate Similarity	NPC187725
0.7128	Intermediate Similarity	NPC141607
0.7128	Intermediate Similarity	NPC475023
0.7126	Intermediate Similarity	NPC159661
0.7125	Intermediate Similarity	NPC113837
0.7125	Intermediate Similarity	NPC289915
0.7115	Intermediate Similarity	NPC265513
0.7113	Intermediate Similarity	NPC469891
0.7113	Intermediate Similarity	NPC469892
0.7113	Intermediate Similarity	NPC469890
0.7105	Intermediate Similarity	NPC212114
0.7105	Intermediate Similarity	NPC120441
0.7105	Intermediate Similarity	NPC65873
0.7105	Intermediate Similarity	NPC300345
0.71	Intermediate Similarity	NPC474866
0.71	Intermediate Similarity	NPC472691
0.71	Intermediate Similarity	NPC475939
0.71	Intermediate Similarity	NPC471829
0.7097	Intermediate Similarity	NPC9822
0.7053	Intermediate Similarity	NPC475057
0.7051	Intermediate Similarity	NPC150196
0.7051	Intermediate Similarity	NPC310758
0.7051	Intermediate Similarity	NPC238023
0.7048	Intermediate Similarity	NPC471189
0.7048	Intermediate Similarity	NPC471188
0.7045	Intermediate Similarity	NPC121800
0.7041	Intermediate Similarity	NPC317280
0.7041	Intermediate Similarity	NPC145052
0.7041	Intermediate Similarity	NPC329387
0.7033	Intermediate Similarity	NPC123476
0.7021	Intermediate Similarity	NPC19256
0.7	Intermediate Similarity	NPC285773
0.7	Intermediate Similarity	NPC215008
0.699	Remote Similarity	NPC112903
0.699	Remote Similarity	NPC470007
0.6989	Remote Similarity	NPC329064
0.6981	Remote Similarity	NPC470253
0.6977	Remote Similarity	NPC175393
0.6974	Remote Similarity	NPC198841
0.6974	Remote Similarity	NPC269586
0.697	Remote Similarity	NPC476042
0.697	Remote Similarity	NPC7435
0.6966	Remote Similarity	NPC303245
0.6966	Remote Similarity	NPC242628
0.6957	Remote Similarity	NPC93843
0.6957	Remote Similarity	NPC243166
0.6951	Remote Similarity	NPC82770
0.6951	Remote Similarity	NPC78954
0.6951	Remote Similarity	NPC239931
0.6947	Remote Similarity	NPC79917
0.6932	Remote Similarity	NPC170484
0.6931	Remote Similarity	NPC247976
0.6923	Remote Similarity	NPC147062
0.6915	Remote Similarity	NPC418308
0.6915	Remote Similarity	NPC113307
0.6907	Remote Similarity	NPC206764
0.6905	Remote Similarity	NPC193578
0.6905	Remote Similarity	NPC208302
0.6905	Remote Similarity	NPC87099
0.6905	Remote Similarity	NPC135433
0.6905	Remote Similarity	NPC280135
0.6905	Remote Similarity	NPC1008
0.6905	Remote Similarity	NPC226999
0.6905	Remote Similarity	NPC155429
0.6905	Remote Similarity	NPC39799
0.6905	Remote Similarity	NPC158028
0.6897	Remote Similarity	NPC179726
0.6893	Remote Similarity	NPC185763
0.6893	Remote Similarity	NPC83409

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 NPC230068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	1053
0.2-0.3	1817
0.3-0.4	3377
0.4-0.5	1868
0.5-0.6	641
0.6-0.7	134
0.7-0.8	27
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
0.8046	Intermediate Similarity	NPD1087	Approved
0.8	Intermediate Similarity	NPD1088	Approved
0.7778	Intermediate Similarity	NPD1086	Approved
0.7778	Intermediate Similarity	NPD3673	Approved
0.7778	Intermediate Similarity	NPD1089	Approved
0.7778	Intermediate Similarity	NPD3672	Approved
0.7778	Intermediate Similarity	NPD1090	Approved
0.7667	Intermediate Similarity	NPD800	Approved
0.766	Intermediate Similarity	NPD3495	Discontinued
0.7553	Intermediate Similarity	NPD1989	Approved
0.7447	Intermediate Similarity	NPD1693	Approved
0.7442	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7631	Approved
0.7412	Intermediate Similarity	NPD225	Approved
0.7412	Intermediate Similarity	NPD227	Approved
0.7356	Intermediate Similarity	NPD942	Approved
0.734	Intermediate Similarity	NPD1563	Approved
0.7312	Intermediate Similarity	NPD7609	Phase 3
0.7283	Intermediate Similarity	NPD5347	Phase 2
0.7283	Intermediate Similarity	NPD5346	Phase 2
0.7263	Intermediate Similarity	NPD4094	Approved
0.7253	Intermediate Similarity	NPD650	Approved
0.7159	Intermediate Similarity	NPD226	Approved
0.7158	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2066	Phase 3
0.7128	Intermediate Similarity	NPD1239	Approved
0.7126	Intermediate Similarity	NPD9490	Approved
0.7113	Intermediate Similarity	NPD1566	Phase 3
0.7113	Intermediate Similarity	NPD1565	Approved
0.7113	Intermediate Similarity	NPD4655	Approved
0.7113	Intermediate Similarity	NPD1564	Approved
0.7113	Intermediate Similarity	NPD4657	Approved
0.7065	Intermediate Similarity	NPD4793	Discontinued
0.7033	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9491	Approved
0.6907	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6049	Phase 2
0.6882	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD675	Discontinued
0.6875	Remote Similarity	NPD1508	Approved
0.6832	Remote Similarity	NPD6024	Approved
0.6832	Remote Similarity	NPD2648	Phase 3
0.6832	Remote Similarity	NPD6027	Approved
0.6832	Remote Similarity	NPD2193	Phase 2
0.6832	Remote Similarity	NPD4803	Discontinued
0.6832	Remote Similarity	NPD2196	Discontinued
0.6822	Remote Similarity	NPD7094	Approved
0.6822	Remote Similarity	NPD6858	Approved
0.68	Remote Similarity	NPD742	Approved
0.6796	Remote Similarity	NPD1766	Approved
0.6796	Remote Similarity	NPD1767	Approved
0.6796	Remote Similarity	NPD1765	Approved
0.6796	Remote Similarity	NPD1763	Approved
0.6796	Remote Similarity	NPD1761	Approved
0.6792	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.67	Remote Similarity	NPD466	Approved
0.67	Remote Similarity	NPD4813	Approved
0.67	Remote Similarity	NPD4263	Approved
0.6698	Remote Similarity	NPD1756	Approved
0.6698	Remote Similarity	NPD4233	Approved
0.6698	Remote Similarity	NPD1752	Approved
0.6698	Remote Similarity	NPD4234	Approved
0.6667	Remote Similarity	NPD1673	Approved
0.6667	Remote Similarity	NPD1843	Approved
0.6635	Remote Similarity	NPD1677	Discontinued
0.6632	Remote Similarity	NPD1101	Approved
0.663	Remote Similarity	NPD3971	Phase 1
0.6606	Remote Similarity	NPD7077	Approved
0.6606	Remote Similarity	NPD7076	Approved
0.6566	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4814	Discontinued
0.6545	Remote Similarity	NPD4766	Approved
0.6542	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5909	Discontinued
0.6535	Remote Similarity	NPD253	Approved
0.6514	Remote Similarity	NPD2607	Approved
0.6505	Remote Similarity	NPD1932	Approved
0.6486	Remote Similarity	NPD3317	Approved
0.6477	Remote Similarity	NPD9716	Approved
0.6476	Remote Similarity	NPD2197	Approved
0.6476	Remote Similarity	NPD1018	Approved
0.6476	Remote Similarity	NPD2192	Approved
0.6471	Remote Similarity	NPD7798	Approved
0.6471	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD1066	Discontinued
0.6449	Remote Similarity	NPD2329	Discontinued
0.6442	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6647	Phase 2
0.6442	Remote Similarity	NPD1929	Approved
0.6442	Remote Similarity	NPD1930	Approved
0.6442	Remote Similarity	NPD5765	Approved
0.6436	Remote Similarity	NPD1099	Approved
0.6436	Remote Similarity	NPD1100	Approved
0.6435	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD2124	Approved
0.6415	Remote Similarity	NPD6685	Approved
0.6396	Remote Similarity	NPD5951	Approved
0.6396	Remote Similarity	NPD2629	Approved
0.6389	Remote Similarity	NPD1317	Discontinued
0.6386	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4544	Approved
0.6373	Remote Similarity	NPD9495	Approved
0.6373	Remote Similarity	NPD5926	Approved
0.6372	Remote Similarity	NPD5990	Approved
0.6372	Remote Similarity	NPD7610	Discontinued
0.6372	Remote Similarity	NPD5991	Approved
0.6364	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2171	Approved
0.6337	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3642	Approved
0.633	Remote Similarity	NPD3644	Approved
0.633	Remote Similarity	NPD3643	Approved
0.633	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD292	Approved
0.6322	Remote Similarity	NPD294	Approved
0.6321	Remote Similarity	NPD5048	Discontinued
0.6316	Remote Similarity	NPD7009	Phase 2
0.6316	Remote Similarity	NPD2205	Approved
0.6316	Remote Similarity	NPD2208	Approved
0.6311	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD2652	Approved
0.6306	Remote Similarity	NPD2650	Approved
0.6306	Remote Similarity	NPD6010	Discontinued
0.6304	Remote Similarity	NPD260	Discontinued
0.63	Remote Similarity	NPD3719	Approved
0.63	Remote Similarity	NPD1409	Phase 3
0.63	Remote Similarity	NPD3718	Approved
0.6296	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2182	Approved
0.6289	Remote Similarity	NPD531	Approved
0.6286	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD3357	Discontinued
0.6277	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5981	Approved
0.625	Remote Similarity	NPD9259	Approved
0.625	Remote Similarity	NPD9257	Approved
0.625	Remote Similarity	NPD3867	Phase 2
0.6239	Remote Similarity	NPD2067	Discontinued
0.6239	Remote Similarity	NPD5278	Discontinued
0.6237	Remote Similarity	NPD3035	Approved
0.6226	Remote Similarity	NPD1237	Approved
0.6226	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD164	Approved
0.6224	Remote Similarity	NPD771	Phase 3
0.619	Remote Similarity	NPD813	Approved
0.6186	Remote Similarity	NPD1282	Approved
0.6174	Remote Similarity	NPD6343	Approved
0.6174	Remote Similarity	NPD6345	Approved
0.617	Remote Similarity	NPD4170	Approved
0.617	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4169	Approved
0.6161	Remote Similarity	NPD1371	Approved
0.6161	Remote Similarity	NPD1374	Approved
0.6161	Remote Similarity	NPD1373	Approved
0.6161	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD1370	Approved
0.6154	Remote Similarity	NPD1238	Approved
0.6154	Remote Similarity	NPD9294	Approved
0.614	Remote Similarity	NPD4574	Approved
0.614	Remote Similarity	NPD4576	Approved
0.6139	Remote Similarity	NPD719	Approved
0.6139	Remote Similarity	NPD720	Approved
0.6139	Remote Similarity	NPD1202	Approved
0.6132	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3979	Approved
0.6129	Remote Similarity	NPD3904	Approved
0.6129	Remote Similarity	NPD3903	Approved
0.6129	Remote Similarity	NPD3981	Approved
0.6122	Remote Similarity	NPD5675	Discontinued
0.6121	Remote Similarity	NPD3024	Approved
0.6121	Remote Similarity	NPD3025	Approved
0.6117	Remote Similarity	NPD9566	Approved
0.6111	Remote Similarity	NPD5704	Approved
0.6111	Remote Similarity	NPD467	Phase 1
0.6111	Remote Similarity	NPD5705	Approved
0.6111	Remote Similarity	NPD5706	Approved
0.6106	Remote Similarity	NPD2508	Discontinued
0.6106	Remote Similarity	NPD1711	Phase 2
0.6105	Remote Similarity	NPD4635	Approved
0.6105	Remote Similarity	NPD2001	Discontinued
0.6095	Remote Similarity	NPD5630	Phase 1
0.6091	Remote Similarity	NPD3581	Discontinued
0.6087	Remote Similarity	NPD6065	Approved
0.6087	Remote Similarity	NPD9563	Approved
0.6087	Remote Similarity	NPD9564	Approved
0.6087	Remote Similarity	NPD79	Approved
0.6082	Remote Similarity	NPD4636	Approved
0.6078	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD4199	Phase 3
0.6068	Remote Similarity	NPD4164	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD3019	Approved
0.6068	Remote Similarity	NPD2932	Approved
0.6068	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7084	Phase 3
0.6053	Remote Similarity	NPD4198	Discontinued
0.605	Remote Similarity	NPD3972	Approved
0.604	Remote Similarity	NPD752	Approved
0.6038	Remote Similarity	NPD4719	Phase 2

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