NPASS Compound

Structure

NPC474543 OpenBabel07101718312D 22 22 0 0 1 0 0 0 0 0999 V2000 1.1942 4.0708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5289 -2.1002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5482 0.9142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2283 3.8120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6594 -1.1088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0306 2.8461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6766 2.1390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1248 0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4177 1.1730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 5 20 1 0 0 0 0 6 9 1 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 10 14 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 4 1 1 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 22 1 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.23
Volume:	341.216
LogP:	4.721
LogD:	4.814
LogS:	-4.796
# Rotatable Bonds:	10
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.355
Synthetic Accessibility Score:	4.397
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.545
MDCK Permeability:	2.058387326542288e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.048

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.424
Plasma Protein Binding (PPB):	91.87913513183594%
Volume Distribution (VD):	0.951
Pgp-substrate:	3.5711419582366943%

ADMET: Metabolism

CYP1A2-inhibitor:	0.234
CYP1A2-substrate:	0.773
CYP2C19-inhibitor:	0.586
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.648
CYP2C9-substrate:	0.279
CYP2D6-inhibitor:	0.107
CYP2D6-substrate:	0.293
CYP3A4-inhibitor:	0.872
CYP3A4-substrate:	0.45

ADMET: Excretion

Clearance (CL):	10.548
Half-life (T1/2):	0.375

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.287
Drug-inuced Liver Injury (DILI):	0.843
AMES Toxicity:	0.134
Rat Oral Acute Toxicity:	0.349
Maximum Recommended Daily Dose:	0.534
Skin Sensitization:	0.455
Carcinogencity:	0.873
Eye Corrosion:	0.1
Eye Irritation:	0.111
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC474543

Natural Product ID:	NPC474543
*Common Name:**	Methyl 2-[4,6-Diethyl-6-[(2S)-2-Methylhexyl]-3H-1,2-Dioxin-3-Yl]Acetate
IUPAC Name:	methyl 2-[4,6-diethyl-6-[(2S)-2-methylhexyl]-3H-1,2-dioxin-3-yl]acetate
Synonyms:
Standard InCHIKey:	NADAFJAMWAJIRR-NXVRBGIVSA-N
Standard InCHI:	InChI=1S/C18H32O4/c1-6-9-10-14(4)12-18(8-3)13-15(7-2)16(21-22-18)11-17(19)20-5/h13-14,16H,6-12H2,1-5H3/t14-,16?,18?/m0/s1
SMILES:	CCCCC(C)CC1(C=C(C(OO1)CC(=O)OC)CC)CC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471597
PubChem CID:	44575469
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0001238] Carboxylic acid esters [CHEMONTID:0003416] Methyl esters

*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
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[11720540]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738400]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	rock wall at 96 m depth, near Blue Hole, Orote Peninsula, Guam	n.a.	PMID[19618913]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20235550]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[23186727]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760075]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722495]

☑ 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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	LD50	=	70.0	mg/L	PMID[449398]

☑ 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 NPC474543 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	195
0.1-0.2	1348
0.2-0.3	6365
0.3-0.4	16726
0.4-0.5	8933
0.5-0.6	6780
0.6-0.7	2105
0.7-0.8	218
0.8-0.85	13
0.85-0.9	6
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC238425
1.0	High Similarity	NPC472018
0.9853	High Similarity	NPC474551
0.9701	High Similarity	NPC69462
0.9552	High Similarity	NPC107130
0.9429	High Similarity	NPC199445
0.9412	High Similarity	NPC472017
0.9296	High Similarity	NPC474447
0.8873	High Similarity	NPC167145
0.8784	High Similarity	NPC121200
0.875	High Similarity	NPC330016
0.8732	High Similarity	NPC126061
0.8684	High Similarity	NPC79277
0.8684	High Similarity	NPC475481
0.8649	High Similarity	NPC476325
0.8649	High Similarity	NPC281296
0.8649	High Similarity	NPC476264
0.8514	High Similarity	NPC239127
0.8378	Intermediate Similarity	NPC255060
0.8378	Intermediate Similarity	NPC60718
0.8267	Intermediate Similarity	NPC469514
0.8228	Intermediate Similarity	NPC69469
0.8205	Intermediate Similarity	NPC476988
0.8182	Intermediate Similarity	NPC308545
0.8182	Intermediate Similarity	NPC82488
0.8028	Intermediate Similarity	NPC284447
0.8026	Intermediate Similarity	NPC476987
0.8026	Intermediate Similarity	NPC266119
0.8026	Intermediate Similarity	NPC59602
0.8026	Intermediate Similarity	NPC152754
0.8	Intermediate Similarity	NPC475989
0.7975	Intermediate Similarity	NPC14044
0.7975	Intermediate Similarity	NPC117960
0.7975	Intermediate Similarity	NPC172309
0.7927	Intermediate Similarity	NPC476104
0.7927	Intermediate Similarity	NPC476982
0.7848	Intermediate Similarity	NPC469920
0.7838	Intermediate Similarity	NPC475310
0.7805	Intermediate Similarity	NPC471344
0.7792	Intermediate Similarity	NPC476985
0.7792	Intermediate Similarity	NPC474316
0.7792	Intermediate Similarity	NPC475744
0.7778	Intermediate Similarity	NPC475947
0.7778	Intermediate Similarity	NPC476983
0.7763	Intermediate Similarity	NPC474758
0.7722	Intermediate Similarity	NPC254996
0.7722	Intermediate Similarity	NPC268502
0.7692	Intermediate Similarity	NPC474760
0.7692	Intermediate Similarity	NPC122847
0.7654	Intermediate Similarity	NPC85772
0.7619	Intermediate Similarity	NPC86005
0.7595	Intermediate Similarity	NPC474341
0.7595	Intermediate Similarity	NPC127526
0.7561	Intermediate Similarity	NPC16488
0.7532	Intermediate Similarity	NPC140287
0.7531	Intermediate Similarity	NPC471325
0.7531	Intermediate Similarity	NPC141810
0.75	Intermediate Similarity	NPC477084
0.75	Intermediate Similarity	NPC113363
0.75	Intermediate Similarity	NPC262085
0.75	Intermediate Similarity	NPC471740
0.75	Intermediate Similarity	NPC34883
0.75	Intermediate Similarity	NPC469483
0.747	Intermediate Similarity	NPC295799
0.7468	Intermediate Similarity	NPC469867
0.7468	Intermediate Similarity	NPC107668
0.7468	Intermediate Similarity	NPC97516
0.7468	Intermediate Similarity	NPC145898
0.7467	Intermediate Similarity	NPC101622
0.7467	Intermediate Similarity	NPC477449
0.7467	Intermediate Similarity	NPC269841
0.7467	Intermediate Similarity	NPC477448
0.7442	Intermediate Similarity	NPC469866
0.7442	Intermediate Similarity	NPC471342
0.7439	Intermediate Similarity	NPC475936
0.7439	Intermediate Similarity	NPC476984
0.7439	Intermediate Similarity	NPC475395
0.7436	Intermediate Similarity	NPC244166
0.7436	Intermediate Similarity	NPC475861
0.7436	Intermediate Similarity	NPC324762
0.7432	Intermediate Similarity	NPC472266
0.7429	Intermediate Similarity	NPC472020
0.7429	Intermediate Similarity	NPC226602
0.7429	Intermediate Similarity	NPC472019
0.7412	Intermediate Similarity	NPC477959
0.7407	Intermediate Similarity	NPC274522
0.7407	Intermediate Similarity	NPC103634
0.7407	Intermediate Similarity	NPC476265
0.7403	Intermediate Similarity	NPC135703
0.7381	Intermediate Similarity	NPC261380
0.7381	Intermediate Similarity	NPC474369
0.7375	Intermediate Similarity	NPC470905
0.7375	Intermediate Similarity	NPC476986
0.7375	Intermediate Similarity	NPC128276
0.7375	Intermediate Similarity	NPC218817
0.7375	Intermediate Similarity	NPC11796
0.7368	Intermediate Similarity	NPC472955
0.7368	Intermediate Similarity	NPC4299
0.7368	Intermediate Similarity	NPC469660
0.7356	Intermediate Similarity	NPC51653
0.7349	Intermediate Similarity	NPC170286
0.7349	Intermediate Similarity	NPC53867
0.7349	Intermediate Similarity	NPC318468
0.7349	Intermediate Similarity	NPC170377
0.7349	Intermediate Similarity	NPC475842
0.7342	Intermediate Similarity	NPC301525
0.7342	Intermediate Similarity	NPC279537
0.7326	Intermediate Similarity	NPC469653
0.7326	Intermediate Similarity	NPC471047
0.7326	Intermediate Similarity	NPC469631
0.7326	Intermediate Similarity	NPC475906
0.7326	Intermediate Similarity	NPC469628
0.7324	Intermediate Similarity	NPC472021
0.7317	Intermediate Similarity	NPC47031
0.7317	Intermediate Similarity	NPC301477
0.7317	Intermediate Similarity	NPC286229
0.7317	Intermediate Similarity	NPC281949
0.7317	Intermediate Similarity	NPC25684
0.7308	Intermediate Similarity	NPC476355
0.7294	Intermediate Similarity	NPC315395
0.7294	Intermediate Similarity	NPC38576
0.7294	Intermediate Similarity	NPC279859
0.7294	Intermediate Similarity	NPC472009
0.7294	Intermediate Similarity	NPC316426
0.7284	Intermediate Similarity	NPC471299
0.7284	Intermediate Similarity	NPC201225
0.7284	Intermediate Similarity	NPC325869
0.7284	Intermediate Similarity	NPC28319
0.7284	Intermediate Similarity	NPC178277
0.7284	Intermediate Similarity	NPC617
0.7273	Intermediate Similarity	NPC129665
0.7273	Intermediate Similarity	NPC163003
0.7262	Intermediate Similarity	NPC475193
0.7262	Intermediate Similarity	NPC471343
0.7262	Intermediate Similarity	NPC243618
0.7262	Intermediate Similarity	NPC477576
0.7262	Intermediate Similarity	NPC477575
0.7262	Intermediate Similarity	NPC120158
0.7262	Intermediate Similarity	NPC9868
0.7262	Intermediate Similarity	NPC70424
0.7262	Intermediate Similarity	NPC474776
0.725	Intermediate Similarity	NPC40049
0.725	Intermediate Similarity	NPC470240
0.725	Intermediate Similarity	NPC57744
0.725	Intermediate Similarity	NPC476794
0.725	Intermediate Similarity	NPC187568
0.725	Intermediate Similarity	NPC476028
0.725	Intermediate Similarity	NPC171204
0.725	Intermediate Similarity	NPC141789
0.725	Intermediate Similarity	NPC41780
0.7241	Intermediate Similarity	NPC475971
0.7237	Intermediate Similarity	NPC144511
0.7237	Intermediate Similarity	NPC329656
0.7237	Intermediate Similarity	NPC199557
0.7237	Intermediate Similarity	NPC296522
0.7229	Intermediate Similarity	NPC475690
0.7229	Intermediate Similarity	NPC7414
0.7229	Intermediate Similarity	NPC123908
0.7229	Intermediate Similarity	NPC10080
0.7229	Intermediate Similarity	NPC35556
0.7215	Intermediate Similarity	NPC329852
0.7215	Intermediate Similarity	NPC329826
0.7215	Intermediate Similarity	NPC469414
0.7215	Intermediate Similarity	NPC228978
0.7209	Intermediate Similarity	NPC471739
0.7209	Intermediate Similarity	NPC472007
0.7209	Intermediate Similarity	NPC478145
0.7209	Intermediate Similarity	NPC478144
0.7209	Intermediate Similarity	NPC471738
0.7195	Intermediate Similarity	NPC233377
0.7191	Intermediate Similarity	NPC248193
0.7179	Intermediate Similarity	NPC470237
0.7176	Intermediate Similarity	NPC197903
0.7176	Intermediate Similarity	NPC99395
0.7176	Intermediate Similarity	NPC125290
0.7176	Intermediate Similarity	NPC137033
0.7164	Intermediate Similarity	NPC216407
0.7162	Intermediate Similarity	NPC326268
0.7162	Intermediate Similarity	NPC318420
0.716	Intermediate Similarity	NPC474005
0.716	Intermediate Similarity	NPC478122
0.716	Intermediate Similarity	NPC315765
0.716	Intermediate Similarity	NPC321514
0.716	Intermediate Similarity	NPC192006
0.716	Intermediate Similarity	NPC471220
0.7159	Intermediate Similarity	NPC313670
0.7143	Intermediate Similarity	NPC475622
0.7143	Intermediate Similarity	NPC108045
0.7143	Intermediate Similarity	NPC476100
0.7143	Intermediate Similarity	NPC474703
0.7143	Intermediate Similarity	NPC11620
0.7143	Intermediate Similarity	NPC222358
0.7126	Intermediate Similarity	NPC475902
0.7126	Intermediate Similarity	NPC472008
0.7125	Intermediate Similarity	NPC12740
0.7125	Intermediate Similarity	NPC469880
0.7125	Intermediate Similarity	NPC271070
0.7125	Intermediate Similarity	NPC123360
0.7125	Intermediate Similarity	NPC110461
0.7125	Intermediate Similarity	NPC235906

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 NPC474543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1952
0.2-0.3	4025
0.3-0.4	2047
0.4-0.5	668
0.5-0.6	225
0.6-0.7	56
0.7-0.8	5
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
0.7349	Intermediate Similarity	NPD7154	Phase 3
0.7317	Intermediate Similarity	NPD5369	Approved
0.7229	Intermediate Similarity	NPD4270	Approved
0.7229	Intermediate Similarity	NPD4269	Approved
0.7215	Intermediate Similarity	NPD8039	Approved
0.7195	Intermediate Similarity	NPD4822	Approved
0.7195	Intermediate Similarity	NPD4819	Approved
0.7195	Intermediate Similarity	NPD4821	Approved
0.7195	Intermediate Similarity	NPD4820	Approved
0.7191	Intermediate Similarity	NPD5779	Approved
0.7191	Intermediate Similarity	NPD5778	Approved
0.7162	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5362	Discontinued
0.7093	Intermediate Similarity	NPD5786	Approved
0.7079	Intermediate Similarity	NPD7983	Approved
0.7045	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6101	Approved
0.6988	Remote Similarity	NPD4252	Approved
0.6988	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5363	Approved
0.6966	Remote Similarity	NPD6698	Approved
0.6966	Remote Similarity	NPD46	Approved
0.6957	Remote Similarity	NPD7839	Suspended
0.6951	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4271	Approved
0.6951	Remote Similarity	NPD4268	Approved
0.6889	Remote Similarity	NPD6411	Approved
0.6824	Remote Similarity	NPD5209	Approved
0.6824	Remote Similarity	NPD6435	Approved
0.6824	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5368	Approved
0.6778	Remote Similarity	NPD5785	Approved
0.6744	Remote Similarity	NPD5332	Approved
0.6744	Remote Similarity	NPD5331	Approved
0.6706	Remote Similarity	NPD4790	Discontinued
0.6703	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD5370	Suspended
0.6623	Remote Similarity	NPD7331	Phase 2
0.6591	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD29	Approved
0.6522	Remote Similarity	NPD28	Approved
0.6517	Remote Similarity	NPD6409	Approved
0.6517	Remote Similarity	NPD7334	Approved
0.6517	Remote Similarity	NPD7146	Approved
0.6517	Remote Similarity	NPD5330	Approved
0.6517	Remote Similarity	NPD6684	Approved
0.6517	Remote Similarity	NPD6422	Discontinued
0.6517	Remote Similarity	NPD7521	Approved
0.6444	Remote Similarity	NPD4251	Approved
0.6444	Remote Similarity	NPD4250	Approved
0.6404	Remote Similarity	NPD1694	Approved
0.64	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6672	Approved
0.6374	Remote Similarity	NPD5737	Approved
0.6374	Remote Similarity	NPD6903	Approved
0.6364	Remote Similarity	NPD3197	Phase 1
0.6364	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3732	Approved
0.6337	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4249	Approved
0.6316	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD1695	Approved
0.6304	Remote Similarity	NPD6051	Approved
0.6292	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4225	Approved
0.6286	Remote Similarity	NPD6927	Phase 3
0.6282	Remote Similarity	NPD7341	Phase 2
0.6277	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD3196	Approved
0.625	Remote Similarity	NPD3194	Approved
0.625	Remote Similarity	NPD3195	Phase 2
0.625	Remote Similarity	NPD4266	Approved
0.6237	Remote Similarity	NPD7838	Discovery
0.6235	Remote Similarity	NPD4756	Discovery
0.6211	Remote Similarity	NPD7900	Approved
0.6211	Remote Similarity	NPD5282	Discontinued
0.6211	Remote Similarity	NPD7748	Approved
0.6211	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6083	Phase 2
0.6186	Remote Similarity	NPD6084	Phase 2
0.617	Remote Similarity	NPD7515	Phase 2
0.6154	Remote Similarity	NPD6371	Approved
0.6154	Remote Similarity	NPD6098	Approved
0.6146	Remote Similarity	NPD5695	Phase 3
0.6129	Remote Similarity	NPD6673	Approved
0.6129	Remote Similarity	NPD6904	Approved
0.6129	Remote Similarity	NPD6080	Approved
0.6125	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7638	Approved
0.6111	Remote Similarity	NPD3172	Approved
0.6111	Remote Similarity	NPD7115	Discovery
0.6104	Remote Similarity	NPD368	Approved
0.6095	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5343	Approved
0.6061	Remote Similarity	NPD7639	Approved
0.6061	Remote Similarity	NPD7640	Approved
0.6038	Remote Similarity	NPD6053	Discontinued
0.6029	Remote Similarity	NPD3174	Discontinued
0.602	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5693	Phase 1
0.5979	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6686	Approved
0.596	Remote Similarity	NPD5696	Approved
0.5934	Remote Similarity	NPD3668	Phase 3
0.5934	Remote Similarity	NPD4786	Approved
0.5922	Remote Similarity	NPD5739	Approved
0.5922	Remote Similarity	NPD6675	Approved
0.5922	Remote Similarity	NPD5048	Discontinued
0.5922	Remote Similarity	NPD7128	Approved
0.5922	Remote Similarity	NPD6402	Approved
0.5914	Remote Similarity	NPD3573	Approved
0.59	Remote Similarity	NPD6648	Approved
0.5895	Remote Similarity	NPD5692	Phase 3
0.5893	Remote Similarity	NPD8513	Phase 3
0.5889	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD3667	Approved
0.5851	Remote Similarity	NPD5208	Approved
0.5843	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5344	Discontinued
0.5833	Remote Similarity	NPD5694	Approved
0.5824	Remote Similarity	NPD6695	Phase 3
0.5824	Remote Similarity	NPD6110	Phase 1
0.5811	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7320	Approved
0.581	Remote Similarity	NPD6899	Approved
0.581	Remote Similarity	NPD6881	Approved
0.5789	Remote Similarity	NPD4753	Phase 2
0.5775	Remote Similarity	NPD3173	Approved
0.5761	Remote Similarity	NPD3666	Approved
0.5761	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD3665	Phase 1
0.5761	Remote Similarity	NPD3133	Approved
0.5758	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD6373	Approved
0.5755	Remote Similarity	NPD6372	Approved
0.5752	Remote Similarity	NPD8516	Approved
0.5752	Remote Similarity	NPD8517	Approved
0.5752	Remote Similarity	NPD8515	Approved
0.5733	Remote Similarity	NPD342	Phase 1
0.5729	Remote Similarity	NPD3672	Approved
0.5729	Remote Similarity	NPD3673	Approved
0.5729	Remote Similarity	NPD5207	Approved
0.5728	Remote Similarity	NPD6647	Phase 2
0.5714	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD5701	Approved
0.5701	Remote Similarity	NPD6883	Approved
0.5701	Remote Similarity	NPD7290	Approved
0.5701	Remote Similarity	NPD7102	Approved
0.5699	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD6924	Approved
0.5698	Remote Similarity	NPD6926	Approved
0.5696	Remote Similarity	NPD4191	Approved
0.5696	Remote Similarity	NPD4194	Approved
0.5696	Remote Similarity	NPD4193	Approved
0.5696	Remote Similarity	NPD4192	Approved
0.567	Remote Similarity	NPD8034	Phase 2
0.567	Remote Similarity	NPD5281	Approved
0.567	Remote Similarity	NPD5284	Approved
0.567	Remote Similarity	NPD8035	Phase 2
0.5667	Remote Similarity	NPD4695	Discontinued
0.5667	Remote Similarity	NPD7332	Phase 2
0.5667	Remote Similarity	NPD6931	Approved
0.5667	Remote Similarity	NPD7514	Phase 3
0.5667	Remote Similarity	NPD6930	Phase 2
0.5652	Remote Similarity	NPD6096	Approved
0.5652	Remote Similarity	NPD2699	Approved
0.5652	Remote Similarity	NPD6097	Approved
0.5648	Remote Similarity	NPD6869	Approved
0.5648	Remote Similarity	NPD6617	Approved
0.5648	Remote Similarity	NPD6847	Approved
0.5648	Remote Similarity	NPD8130	Phase 1
0.5648	Remote Similarity	NPD6649	Approved
0.5648	Remote Similarity	NPD6650	Approved
0.5641	Remote Similarity	NPD3198	Approved
0.5638	Remote Similarity	NPD3618	Phase 1
0.5638	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD4623	Approved
0.5638	Remote Similarity	NPD4519	Discontinued
0.5638	Remote Similarity	NPD5279	Phase 3
0.5634	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD8264	Approved
0.5625	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5328	Approved
0.5625	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6008	Approved
0.5618	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.561	Remote Similarity	NPD3704	Approved
0.5607	Remote Similarity	NPD6014	Approved
0.5607	Remote Similarity	NPD6013	Approved
0.5607	Remote Similarity	NPD6012	Approved
0.5607	Remote Similarity	NPD6413	Approved
0.56	Remote Similarity	NPD4228	Discovery
0.56	Remote Similarity	NPD7732	Phase 3

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