NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.17
Volume:	243.025
LogP:	4.836
LogD:	4.354
LogS:	-4.824
# Rotatable Bonds:	3
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.772
Synthetic Accessibility Score:	2.141
Fsp3:	0.571
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:	-4.613
MDCK Permeability:	1.6543266610824503e-05
Pgp-inhibitor:	0.537
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.174
20% Bioavailability (F20%):	0.326
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.363
Plasma Protein Binding (PPB):	95.11937713623047%
Volume Distribution (VD):	5.28
Pgp-substrate:	5.477334499359131%

ADMET: Metabolism

CYP1A2-inhibitor:	0.329
CYP1A2-substrate:	0.774
CYP2C19-inhibitor:	0.821
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.315
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.408
CYP2D6-substrate:	0.86
CYP3A4-inhibitor:	0.112
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	6.955
Half-life (T1/2):	0.342

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.241
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.794
Carcinogencity:	0.045
Eye Corrosion:	0.981
Eye Irritation:	0.982
Respiratory Toxicity:	0.618

Download Data

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

Natural Product: NPC152415

Natural Product ID:	NPC152415
*Common Name:**	2-(2,4,4-Trimethylpentan-2-Yl)Phenol
IUPAC Name:	2-(2,4,4-trimethylpentan-2-yl)phenol
Synonyms:
Standard InCHIKey:	XSXWOBXNYNULJG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H22O/c1-13(2,3)10-14(4,5)11-8-6-7-9-12(11)15/h6-9,15H,10H2,1-5H3
SMILES:	CC(C)(C)CC(C)(C)c1ccccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3182290
PubChem CID:	62530
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
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	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
Potency	54

Activity Type	# Activity
Individual Protein	7
Others	47

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	39104.7	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	43497.3	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	61441.5	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	55236.9	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	49229.9	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	49229.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21990.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43876.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1375.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	34852.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	39104.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30793.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61976.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	19429.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2180	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	55236.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21800.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61441.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68938.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	49229.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24460.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	19598.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43497.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48804.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54759.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27444.9	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	24673.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	31062	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 NPC152415 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	278
0.1-0.2	1813
0.2-0.3	4386
0.3-0.4	13405
0.4-0.5	7475
0.5-0.6	10172
0.6-0.7	4002
0.7-0.8	861
0.8-0.85	192
0.85-0.9	70
0.9-0.95	36
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC306074
0.9565	High Similarity	NPC299762
0.9565	High Similarity	NPC122005
0.9565	High Similarity	NPC33675
0.9565	High Similarity	NPC252821
0.9556	High Similarity	NPC289769
0.9556	High Similarity	NPC27323
0.9556	High Similarity	NPC316301
0.9462	High Similarity	NPC225506
0.9444	High Similarity	NPC55903
0.9362	High Similarity	NPC252105
0.9333	High Similarity	NPC155908
0.9318	High Similarity	NPC407
0.9318	High Similarity	NPC307235
0.9247	High Similarity	NPC225464
0.9247	High Similarity	NPC77492
0.9247	High Similarity	NPC79241
0.9247	High Similarity	NPC6597
0.9239	High Similarity	NPC144682
0.9239	High Similarity	NPC222146
0.9205	High Similarity	NPC155393
0.9149	High Similarity	NPC92730
0.914	High Similarity	NPC312132
0.914	High Similarity	NPC259512
0.913	High Similarity	NPC245187
0.9121	High Similarity	NPC304541
0.9111	High Similarity	NPC123273
0.9111	High Similarity	NPC318325
0.9111	High Similarity	NPC242240
0.9091	High Similarity	NPC286904
0.9072	High Similarity	NPC47284
0.9062	High Similarity	NPC269212
0.9053	High Similarity	NPC72729
0.9032	High Similarity	NPC8392
0.9022	High Similarity	NPC271440
0.9022	High Similarity	NPC210497
0.9022	High Similarity	NPC147284
0.9022	High Similarity	NPC162314
0.9022	High Similarity	NPC3358
0.9022	High Similarity	NPC94139
0.9022	High Similarity	NPC306884
0.9011	High Similarity	NPC192
0.9	High Similarity	NPC113460
0.9	High Similarity	NPC27974
0.9	High Similarity	NPC25493
0.898	High Similarity	NPC310456
0.898	High Similarity	NPC53740
0.8913	High Similarity	NPC231150
0.8913	High Similarity	NPC204210
0.8901	High Similarity	NPC177420
0.8901	High Similarity	NPC280347
0.8901	High Similarity	NPC258219
0.8901	High Similarity	NPC98772
0.8889	High Similarity	NPC320439
0.8889	High Similarity	NPC184169
0.8889	High Similarity	NPC23167
0.8854	High Similarity	NPC48730
0.8854	High Similarity	NPC211885
0.8854	High Similarity	NPC248396
0.8854	High Similarity	NPC129373
0.8842	High Similarity	NPC152097
0.8804	High Similarity	NPC55561
0.88	High Similarity	NPC306295
0.88	High Similarity	NPC64586
0.8788	High Similarity	NPC155072
0.8778	High Similarity	NPC197783
0.8776	High Similarity	NPC475225
0.875	High Similarity	NPC260775
0.875	High Similarity	NPC128723
0.8723	High Similarity	NPC128062
0.8723	High Similarity	NPC76938
0.871	High Similarity	NPC270547
0.8696	High Similarity	NPC70436
0.8687	High Similarity	NPC138942
0.8673	High Similarity	NPC235762
0.8673	High Similarity	NPC108497
0.8673	High Similarity	NPC168829
0.8673	High Similarity	NPC471228
0.8667	High Similarity	NPC248817
0.8667	High Similarity	NPC175313
0.8667	High Similarity	NPC150837
0.866	High Similarity	NPC174911
0.866	High Similarity	NPC130756
0.866	High Similarity	NPC12931
0.866	High Similarity	NPC70677
0.8646	High Similarity	NPC156313
0.8646	High Similarity	NPC474073
0.8646	High Similarity	NPC475078
0.8632	High Similarity	NPC26244
0.8632	High Similarity	NPC32714
0.8627	High Similarity	NPC13482
0.8617	High Similarity	NPC29373
0.86	High Similarity	NPC477814
0.86	High Similarity	NPC271274
0.8587	High Similarity	NPC19680
0.8586	High Similarity	NPC475580
0.8586	High Similarity	NPC288411
0.8586	High Similarity	NPC120719
0.8571	High Similarity	NPC477685
0.8571	High Similarity	NPC51015
0.8571	High Similarity	NPC12221
0.8556	High Similarity	NPC265146
0.8556	High Similarity	NPC124436
0.8544	High Similarity	NPC77772
0.8544	High Similarity	NPC275627
0.8544	High Similarity	NPC266937
0.8544	High Similarity	NPC470770
0.8542	High Similarity	NPC216520
0.8542	High Similarity	NPC132271
0.8542	High Similarity	NPC292730
0.8542	High Similarity	NPC82664
0.8542	High Similarity	NPC473388
0.8526	High Similarity	NPC151715
0.8515	High Similarity	NPC66834
0.8511	High Similarity	NPC45040
0.85	High Similarity	NPC219286
0.85	High Similarity	NPC99557
0.85	High Similarity	NPC117115
0.8462	Intermediate Similarity	NPC250323
0.8462	Intermediate Similarity	NPC228425
0.8462	Intermediate Similarity	NPC62867
0.8462	Intermediate Similarity	NPC177962
0.8447	Intermediate Similarity	NPC141782
0.8438	Intermediate Similarity	NPC274678
0.8431	Intermediate Similarity	NPC470039
0.8421	Intermediate Similarity	NPC138117
0.8421	Intermediate Similarity	NPC325292
0.8416	Intermediate Similarity	NPC21594
0.8404	Intermediate Similarity	NPC47950
0.8404	Intermediate Similarity	NPC300017
0.84	Intermediate Similarity	NPC238696
0.84	Intermediate Similarity	NPC272029
0.84	Intermediate Similarity	NPC227458
0.84	Intermediate Similarity	NPC218879
0.84	Intermediate Similarity	NPC244513
0.8384	Intermediate Similarity	NPC471578
0.8384	Intermediate Similarity	NPC80800
0.8384	Intermediate Similarity	NPC101025
0.8367	Intermediate Similarity	NPC80027
0.8365	Intermediate Similarity	NPC176279
0.8365	Intermediate Similarity	NPC260323
0.8352	Intermediate Similarity	NPC474354
0.8351	Intermediate Similarity	NPC202986
0.835	Intermediate Similarity	NPC58865
0.8333	Intermediate Similarity	NPC151477
0.8333	Intermediate Similarity	NPC228737
0.8333	Intermediate Similarity	NPC158253
0.8333	Intermediate Similarity	NPC232523
0.8333	Intermediate Similarity	NPC204901
0.8317	Intermediate Similarity	NPC471350
0.8317	Intermediate Similarity	NPC303141
0.8317	Intermediate Similarity	NPC37802
0.8315	Intermediate Similarity	NPC133050
0.8302	Intermediate Similarity	NPC195922
0.83	Intermediate Similarity	NPC24404
0.83	Intermediate Similarity	NPC302219
0.83	Intermediate Similarity	NPC222522
0.83	Intermediate Similarity	NPC94351
0.83	Intermediate Similarity	NPC71002
0.83	Intermediate Similarity	NPC168303
0.83	Intermediate Similarity	NPC313030
0.83	Intermediate Similarity	NPC53051
0.83	Intermediate Similarity	NPC168393
0.83	Intermediate Similarity	NPC242342
0.83	Intermediate Similarity	NPC85479
0.83	Intermediate Similarity	NPC62351
0.83	Intermediate Similarity	NPC233827
0.83	Intermediate Similarity	NPC106396
0.83	Intermediate Similarity	NPC146798
0.83	Intermediate Similarity	NPC249828
0.8286	Intermediate Similarity	NPC98372
0.8283	Intermediate Similarity	NPC10588
0.8283	Intermediate Similarity	NPC166761
0.8283	Intermediate Similarity	NPC130103
0.8283	Intermediate Similarity	NPC294741
0.8269	Intermediate Similarity	NPC296683
0.8265	Intermediate Similarity	NPC32674
0.8261	Intermediate Similarity	NPC474211
0.8252	Intermediate Similarity	NPC174981
0.8252	Intermediate Similarity	NPC262365
0.8247	Intermediate Similarity	NPC313650
0.8247	Intermediate Similarity	NPC246679
0.8242	Intermediate Similarity	NPC168855
0.8235	Intermediate Similarity	NPC248904
0.8235	Intermediate Similarity	NPC469913
0.8235	Intermediate Similarity	NPC99836
0.8235	Intermediate Similarity	NPC54765
0.8235	Intermediate Similarity	NPC12640
0.8235	Intermediate Similarity	NPC201662
0.8218	Intermediate Similarity	NPC323810
0.8218	Intermediate Similarity	NPC119860
0.8218	Intermediate Similarity	NPC102216
0.8211	Intermediate Similarity	NPC312304
0.82	Intermediate Similarity	NPC192032
0.82	Intermediate Similarity	NPC11280
0.82	Intermediate Similarity	NPC137415
0.82	Intermediate Similarity	NPC472585
0.82	Intermediate Similarity	NPC147310
0.82	Intermediate Similarity	NPC294186
0.82	Intermediate Similarity	NPC24407

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 NPC152415 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	1062
0.2-0.3	1276
0.3-0.4	2917
0.4-0.5	1936
0.5-0.6	1153
0.6-0.7	439
0.7-0.8	67
0.8-0.85	8
0.85-0.9	3
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9556	High Similarity	NPD1432	Clinical (unspecified phase)
0.9255	High Similarity	NPD289	Clinical (unspecified phase)
0.9239	High Similarity	NPD1809	Phase 2
0.9239	High Similarity	NPD844	Approved
0.9231	High Similarity	NPD845	Approved
0.914	High Similarity	NPD288	Approved
0.875	High Similarity	NPD3020	Approved
0.8632	High Similarity	NPD2859	Approved
0.8632	High Similarity	NPD2860	Approved
0.8571	High Similarity	NPD846	Approved
0.8571	High Similarity	NPD940	Approved
0.8556	High Similarity	NPD111	Approved
0.8526	High Similarity	NPD2933	Approved
0.8526	High Similarity	NPD2934	Approved
0.8235	Intermediate Similarity	NPD1445	Approved
0.8235	Intermediate Similarity	NPD1444	Approved
0.8173	Intermediate Similarity	NPD4750	Phase 3
0.8019	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3021	Approved
0.8	Intermediate Similarity	NPD1792	Phase 2
0.8	Intermediate Similarity	NPD3022	Approved
0.7981	Intermediate Similarity	NPD2342	Discontinued
0.7963	Intermediate Similarity	NPD1793	Approved
0.7963	Intermediate Similarity	NPD1791	Approved
0.7944	Intermediate Similarity	NPD7635	Approved
0.787	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4589	Approved
0.7727	Intermediate Similarity	NPD9087	Approved
0.7727	Intermediate Similarity	NPD6671	Approved
0.7723	Intermediate Similarity	NPD9273	Approved
0.7706	Intermediate Similarity	NPD2229	Approved
0.7706	Intermediate Similarity	NPD2234	Approved
0.7706	Intermediate Similarity	NPD2228	Approved
0.7692	Intermediate Similarity	NPD9608	Approved
0.7692	Intermediate Similarity	NPD9610	Approved
0.7679	Intermediate Similarity	NPD3091	Approved
0.7596	Intermediate Similarity	NPD9500	Approved
0.7573	Intermediate Similarity	NPD1242	Phase 1
0.7544	Intermediate Similarity	NPD1751	Approved
0.7544	Intermediate Similarity	NPD3019	Approved
0.7544	Intermediate Similarity	NPD4059	Approved
0.7544	Intermediate Similarity	NPD2932	Approved
0.7522	Intermediate Similarity	NPD5304	Approved
0.7522	Intermediate Similarity	NPD5303	Approved
0.7522	Intermediate Similarity	NPD7330	Discontinued
0.7522	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD9294	Approved
0.7456	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3092	Approved
0.7414	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7157	Approved
0.7404	Intermediate Similarity	NPD3028	Approved
0.7391	Intermediate Similarity	NPD9088	Approved
0.7364	Intermediate Similarity	NPD228	Approved
0.7345	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7636	Approved
0.7328	Intermediate Similarity	NPD3143	Discontinued
0.7328	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD290	Approved
0.7304	Intermediate Similarity	NPD4093	Discontinued
0.7288	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD1755	Approved
0.7248	Intermediate Similarity	NPD2684	Approved
0.7241	Intermediate Similarity	NPD4626	Approved
0.7241	Intermediate Similarity	NPD3095	Discontinued
0.7227	Intermediate Similarity	NPD6696	Suspended
0.7222	Intermediate Similarity	NPD968	Approved
0.7203	Intermediate Similarity	NPD3070	Discontinued
0.7193	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD9614	Approved
0.7168	Intermediate Similarity	NPD497	Approved
0.7168	Intermediate Similarity	NPD475	Phase 2
0.7168	Intermediate Similarity	NPD9618	Approved
0.7167	Intermediate Similarity	NPD3094	Phase 2
0.7143	Intermediate Similarity	NPD9379	Approved
0.7143	Intermediate Similarity	NPD1138	Approved
0.7143	Intermediate Similarity	NPD9377	Approved
0.7143	Intermediate Similarity	NPD4749	Approved
0.7119	Intermediate Similarity	NPD1201	Approved
0.7119	Intermediate Similarity	NPD1610	Phase 2
0.7107	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2194	Approved
0.7107	Intermediate Similarity	NPD2195	Approved
0.7105	Intermediate Similarity	NPD255	Approved
0.7105	Intermediate Similarity	NPD709	Approved
0.7105	Intermediate Similarity	NPD256	Approved
0.7103	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD1778	Approved
0.7091	Intermediate Similarity	NPD74	Approved
0.7091	Intermediate Similarity	NPD9266	Approved
0.7083	Intermediate Similarity	NPD9089	Approved
0.708	Intermediate Similarity	NPD498	Approved
0.708	Intermediate Similarity	NPD495	Approved
0.708	Intermediate Similarity	NPD496	Approved
0.7075	Intermediate Similarity	NPD1616	Discontinued
0.7069	Intermediate Similarity	NPD1759	Phase 1
0.7059	Intermediate Similarity	NPD2233	Approved
0.7059	Intermediate Similarity	NPD2232	Approved
0.7059	Intermediate Similarity	NPD2230	Approved
0.7054	Intermediate Similarity	NPD1137	Approved
0.7054	Intermediate Similarity	NPD1139	Approved
0.7049	Intermediate Similarity	NPD3637	Approved
0.7049	Intermediate Similarity	NPD3635	Approved
0.7049	Intermediate Similarity	NPD5736	Approved
0.7049	Intermediate Similarity	NPD3636	Approved
0.7043	Intermediate Similarity	NPD9493	Approved
0.7034	Intermediate Similarity	NPD3496	Discontinued
0.7016	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4817	Approved
0.7009	Intermediate Similarity	NPD4818	Approved
0.7	Intermediate Similarity	NPD9267	Approved
0.7	Intermediate Similarity	NPD9264	Approved
0.7	Intermediate Similarity	NPD9263	Approved
0.6992	Remote Similarity	NPD2606	Approved
0.6992	Remote Similarity	NPD4908	Phase 1
0.6992	Remote Similarity	NPD2605	Approved
0.6991	Remote Similarity	NPD7843	Approved
0.6991	Remote Similarity	NPD821	Approved
0.6983	Remote Similarity	NPD9616	Approved
0.6983	Remote Similarity	NPD16	Approved
0.6983	Remote Similarity	NPD1758	Phase 1
0.6983	Remote Similarity	NPD9613	Approved
0.6983	Remote Similarity	NPD9615	Approved
0.6983	Remote Similarity	NPD856	Approved
0.6979	Remote Similarity	NPD9093	Approved
0.6949	Remote Similarity	NPD2286	Discontinued
0.6949	Remote Similarity	NPD2667	Approved
0.6949	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2668	Approved
0.6935	Remote Similarity	NPD5155	Approved
0.6935	Remote Similarity	NPD4625	Phase 3
0.6935	Remote Similarity	NPD5156	Approved
0.6931	Remote Similarity	NPD9295	Approved
0.693	Remote Similarity	NPD1398	Phase 1
0.693	Remote Similarity	NPD5283	Phase 1
0.6923	Remote Similarity	NPD1548	Phase 1
0.6923	Remote Similarity	NPD316	Approved
0.6911	Remote Similarity	NPD4208	Discontinued
0.6911	Remote Similarity	NPD2861	Phase 2
0.6911	Remote Similarity	NPD4212	Discontinued
0.6893	Remote Similarity	NPD1088	Approved
0.6891	Remote Similarity	NPD1981	Approved
0.6891	Remote Similarity	NPD1980	Approved
0.6891	Remote Similarity	NPD1983	Approved
0.6891	Remote Similarity	NPD3026	Approved
0.6891	Remote Similarity	NPD3023	Approved
0.6885	Remote Similarity	NPD1134	Approved
0.6885	Remote Similarity	NPD1129	Approved
0.6885	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1133	Approved
0.6885	Remote Similarity	NPD1164	Approved
0.6885	Remote Similarity	NPD2797	Approved
0.6885	Remote Similarity	NPD1135	Approved
0.6885	Remote Similarity	NPD1131	Approved
0.6885	Remote Similarity	NPD1470	Approved
0.688	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5451	Approved
0.6869	Remote Similarity	NPD9073	Approved
0.6864	Remote Similarity	NPD3024	Approved
0.6864	Remote Similarity	NPD3444	Approved
0.6864	Remote Similarity	NPD3025	Approved
0.6864	Remote Similarity	NPD1357	Approved
0.6864	Remote Similarity	NPD3443	Approved
0.6864	Remote Similarity	NPD5691	Approved
0.6864	Remote Similarity	NPD3445	Approved
0.6855	Remote Similarity	NPD3594	Approved
0.6855	Remote Similarity	NPD3595	Approved
0.6855	Remote Similarity	NPD4207	Discontinued
0.6847	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD317	Approved
0.6838	Remote Similarity	NPD318	Approved
0.6833	Remote Similarity	NPD422	Phase 1
0.6832	Remote Similarity	NPD1101	Approved
0.6829	Remote Similarity	NPD4624	Approved
0.6825	Remote Similarity	NPD6663	Approved
0.6814	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2557	Approved
0.681	Remote Similarity	NPD6387	Discontinued
0.6803	Remote Similarity	NPD8651	Approved
0.6797	Remote Similarity	NPD4097	Suspended
0.6789	Remote Similarity	NPD3682	Approved
0.6789	Remote Similarity	NPD3681	Approved
0.6789	Remote Similarity	NPD4656	Approved
0.6789	Remote Similarity	NPD4658	Approved
0.6789	Remote Similarity	NPD3683	Approved
0.6789	Remote Similarity	NPD4231	Approved
0.6789	Remote Similarity	NPD4229	Approved
0.6789	Remote Similarity	NPD3680	Approved
0.6774	Remote Similarity	NPD1712	Approved
0.6772	Remote Similarity	NPD4060	Phase 1
0.6772	Remote Similarity	NPD6346	Approved
0.6752	Remote Similarity	NPD7340	Approved
0.6752	Remote Similarity	NPD9568	Approved
0.6748	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4103	Phase 2
0.6731	Remote Similarity	NPD752	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