NPASS Compound

Structure

NPC474552 OpenBabel07101719252D 25 25 0 0 1 0 0 0 0 0999 V2000 -5.3473 2.2259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 1.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0544 -2.3741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7424 2.1566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6402 2.9331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5176 0.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 -1.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6742 2.6742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4154 1.7083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1907 0.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 -0.7412 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 -2.4495 1.4495 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2247 0.2247 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 4 9 1 0 0 0 0 6 10 1 0 0 0 0 7 17 1 0 0 0 0 10 11 1 0 0 0 0 11 16 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 5 1 6 0 0 0 18 8 1 1 0 0 0 18 19 1 0 0 0 0 19 13 1 1 0 0 0 19 24 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 21 9 1 1 0 0 0 21 25 1 0 0 0 0 24 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.29
Volume:	395.74
LogP:	6.398
LogD:	5.081
LogS:	-5.169
# Rotatable Bonds:	12
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	4.517
Fsp3:	0.952
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.663
MDCK Permeability:	2.8556669349200092e-05
Pgp-inhibitor:	0.905
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	95.79615783691406%
Volume Distribution (VD):	0.301
Pgp-substrate:	2.9458014965057373%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.787
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.935
CYP2C9-inhibitor:	0.459
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.772
CYP3A4-substrate:	0.122

ADMET: Excretion

Clearance (CL):	10.907
Half-life (T1/2):	0.291

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.469
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.931
Carcinogencity:	0.415
Eye Corrosion:	0.948
Eye Irritation:	0.786
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC474552

Natural Product ID:	NPC474552
*Common Name:**	2-[(3S,4S,6S)-4,6-Diethyl-6-[(4S)-2-Ethyl-4-Methyloctyl]Dioxan-3-Yl]Acetic Acid
IUPAC Name:	2-[(3S,4S,6S)-4,6-diethyl-6-[(4S)-2-ethyl-4-methyloctyl]dioxan-3-yl]acetic acid
Synonyms:
Standard InCHIKey:	ZZSLGVAAMWQFDX-UTTKFVPTSA-N
Standard InCHI:	InChI=1S/C21H40O4/c1-6-10-11-16(5)12-17(7-2)14-21(9-4)15-18(8-3)19(24-25-21)13-20(22)23/h16-19H,6-15H2,1-5H3,(H,22,23)/t16-,17?,18-,19-,21-/m0/s1
SMILES:	CCCC[C@@H](CC(C[C@]1(CC)OO[C@H]([C@H](C1)CC)CC(=O)O)CC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471804
PubChem CID:	44575471
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000368] Dioxanes [CHEMONTID:0001312] 1,2-dioxanes

*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	=	15.0	mg/L	PMID[474365]

☑ 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 NPC474552 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	352
0.1-0.2	3570
0.2-0.3	12454
0.3-0.4	12461
0.4-0.5	8512
0.5-0.6	4908
0.6-0.7	354
0.7-0.8	68
0.8-0.85	5
0.85-0.9	2
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9483	High Similarity	NPC475821
0.9322	High Similarity	NPC472021
0.9153	High Similarity	NPC472019
0.9153	High Similarity	NPC226602
0.9153	High Similarity	NPC472020
0.873	High Similarity	NPC306805
0.873	High Similarity	NPC215987
0.873	High Similarity	NPC476330
0.8286	Intermediate Similarity	NPC469514
0.8226	Intermediate Similarity	NPC469924
0.8169	Intermediate Similarity	NPC122847
0.8154	Intermediate Similarity	NPC469926
0.8056	Intermediate Similarity	NPC476986
0.8056	Intermediate Similarity	NPC470905
0.8	Intermediate Similarity	NPC314103
0.7969	Intermediate Similarity	NPC469923
0.7945	Intermediate Similarity	NPC82488
0.7945	Intermediate Similarity	NPC308545
0.7917	Intermediate Similarity	NPC281296
0.7917	Intermediate Similarity	NPC474003
0.791	Intermediate Similarity	NPC469925
0.7812	Intermediate Similarity	NPC469921
0.7808	Intermediate Similarity	NPC121200
0.7746	Intermediate Similarity	NPC330016
0.7733	Intermediate Similarity	NPC14044
0.7733	Intermediate Similarity	NPC172309
0.7733	Intermediate Similarity	NPC117960
0.7671	Intermediate Similarity	NPC469867
0.7656	Intermediate Similarity	NPC470363
0.7632	Intermediate Similarity	NPC476292
0.7632	Intermediate Similarity	NPC476984
0.7632	Intermediate Similarity	NPC475395
0.7632	Intermediate Similarity	NPC474605
0.7627	Intermediate Similarity	NPC90904
0.7606	Intermediate Similarity	NPC167145
0.7586	Intermediate Similarity	NPC324793
0.7586	Intermediate Similarity	NPC477878
0.7576	Intermediate Similarity	NPC235788
0.7541	Intermediate Similarity	NPC72722
0.7536	Intermediate Similarity	NPC319007
0.7534	Intermediate Similarity	NPC476985
0.7534	Intermediate Similarity	NPC474316
0.7534	Intermediate Similarity	NPC152754
0.7534	Intermediate Similarity	NPC475744
0.7534	Intermediate Similarity	NPC59602
0.7534	Intermediate Similarity	NPC476987
0.7532	Intermediate Similarity	NPC476983
0.7532	Intermediate Similarity	NPC476100
0.75	Intermediate Similarity	NPC241949
0.7467	Intermediate Similarity	NPC113363
0.7436	Intermediate Similarity	NPC471343
0.7432	Intermediate Similarity	NPC476264
0.7432	Intermediate Similarity	NPC476325
0.7424	Intermediate Similarity	NPC469922
0.7414	Intermediate Similarity	NPC21844
0.7397	Intermediate Similarity	NPC199445
0.7397	Intermediate Similarity	NPC60718
0.7342	Intermediate Similarity	NPC471344
0.7297	Intermediate Similarity	NPC474447
0.7297	Intermediate Similarity	NPC474020
0.7288	Intermediate Similarity	NPC131770
0.7288	Intermediate Similarity	NPC200618
0.725	Intermediate Similarity	NPC262085
0.725	Intermediate Similarity	NPC476982
0.725	Intermediate Similarity	NPC475181
0.725	Intermediate Similarity	NPC476104
0.7241	Intermediate Similarity	NPC314679
0.7237	Intermediate Similarity	NPC268502
0.7237	Intermediate Similarity	NPC254996
0.7143	Intermediate Similarity	NPC476265
0.7143	Intermediate Similarity	NPC274522
0.7143	Intermediate Similarity	NPC286842
0.7119	Intermediate Similarity	NPC328497
0.7119	Intermediate Similarity	NPC324004
0.7089	Intermediate Similarity	NPC69469
0.7069	Intermediate Similarity	NPC55023
0.7067	Intermediate Similarity	NPC239127
0.7051	Intermediate Similarity	NPC476988
0.7027	Intermediate Similarity	NPC477930
0.7027	Intermediate Similarity	NPC477867
0.7	Intermediate Similarity	NPC106872
0.7	Intermediate Similarity	NPC135043
0.7	Intermediate Similarity	NPC315525
0.6988	Remote Similarity	NPC471342
0.6988	Remote Similarity	NPC469866
0.6986	Remote Similarity	NPC96322
0.6986	Remote Similarity	NPC478227
0.6974	Remote Similarity	NPC83108
0.6974	Remote Similarity	NPC214030
0.6974	Remote Similarity	NPC477918
0.6951	Remote Similarity	NPC51662
0.6951	Remote Similarity	NPC314364
0.6944	Remote Similarity	NPC98711
0.6935	Remote Similarity	NPC314084
0.6933	Remote Similarity	NPC228411
0.6933	Remote Similarity	NPC179922
0.6933	Remote Similarity	NPC477934
0.6933	Remote Similarity	NPC255060
0.6901	Remote Similarity	NPC41542
0.6892	Remote Similarity	NPC474543
0.6892	Remote Similarity	NPC238425
0.6892	Remote Similarity	NPC472018
0.6875	Remote Similarity	NPC469937
0.6875	Remote Similarity	NPC53463
0.6875	Remote Similarity	NPC320588
0.6875	Remote Similarity	NPC23155
0.6857	Remote Similarity	NPC230047
0.6857	Remote Similarity	NPC19311
0.6849	Remote Similarity	NPC470268
0.6842	Remote Similarity	NPC477933
0.6842	Remote Similarity	NPC477932
0.6842	Remote Similarity	NPC266119
0.6835	Remote Similarity	NPC79277
0.6835	Remote Similarity	NPC475481
0.6833	Remote Similarity	NPC249754
0.6829	Remote Similarity	NPC476717
0.6806	Remote Similarity	NPC82315
0.68	Remote Similarity	NPC317212
0.68	Remote Similarity	NPC474551
0.6795	Remote Similarity	NPC19841
0.679	Remote Similarity	NPC477434
0.679	Remote Similarity	NPC475193
0.679	Remote Similarity	NPC120158
0.6757	Remote Similarity	NPC126061
0.6757	Remote Similarity	NPC470243
0.6757	Remote Similarity	NPC474590
0.6753	Remote Similarity	NPC317913
0.6753	Remote Similarity	NPC307865
0.6753	Remote Similarity	NPC207010
0.675	Remote Similarity	NPC477936
0.675	Remote Similarity	NPC477935
0.6721	Remote Similarity	NPC13105
0.6712	Remote Similarity	NPC475062
0.6709	Remote Similarity	NPC469920
0.6709	Remote Similarity	NPC103634
0.6707	Remote Similarity	NPC131350
0.6707	Remote Similarity	NPC477205
0.6667	Remote Similarity	NPC12438
0.6667	Remote Similarity	NPC308301
0.6667	Remote Similarity	NPC474755
0.6667	Remote Similarity	NPC30195
0.6667	Remote Similarity	NPC472608
0.6667	Remote Similarity	NPC471221
0.6627	Remote Similarity	NPC477993
0.6627	Remote Similarity	NPC477994
0.6623	Remote Similarity	NPC4209
0.6622	Remote Similarity	NPC69462
0.662	Remote Similarity	NPC469791
0.6618	Remote Similarity	NPC17935
0.6613	Remote Similarity	NPC304162
0.661	Remote Similarity	NPC74845
0.6588	Remote Similarity	NPC477443
0.6588	Remote Similarity	NPC477440
0.6585	Remote Similarity	NPC319909
0.6582	Remote Similarity	NPC474754
0.6579	Remote Similarity	NPC167702
0.6579	Remote Similarity	NPC280026
0.6579	Remote Similarity	NPC215030
0.6552	Remote Similarity	NPC209970
0.6552	Remote Similarity	NPC307783
0.6552	Remote Similarity	NPC171736
0.6552	Remote Similarity	NPC248763
0.6552	Remote Similarity	NPC216630
0.6552	Remote Similarity	NPC325452
0.6552	Remote Similarity	NPC196924
0.6552	Remote Similarity	NPC149184
0.6548	Remote Similarity	NPC197333
0.6538	Remote Similarity	NPC169389
0.6538	Remote Similarity	NPC70996
0.6538	Remote Similarity	NPC474433
0.6538	Remote Similarity	NPC477919
0.6538	Remote Similarity	NPC471151
0.6538	Remote Similarity	NPC120776
0.6538	Remote Similarity	NPC180199
0.6538	Remote Similarity	NPC240170
0.6538	Remote Similarity	NPC108014
0.6533	Remote Similarity	NPC469940
0.6533	Remote Similarity	NPC185419
0.6533	Remote Similarity	NPC184550
0.6528	Remote Similarity	NPC473899
0.6512	Remote Similarity	NPC477444
0.6512	Remote Similarity	NPC477442
0.6512	Remote Similarity	NPC477433
0.6508	Remote Similarity	NPC305182
0.6508	Remote Similarity	NPC55678
0.6506	Remote Similarity	NPC476715
0.65	Remote Similarity	NPC469781
0.65	Remote Similarity	NPC287231
0.65	Remote Similarity	NPC47363
0.6494	Remote Similarity	NPC212733
0.6494	Remote Similarity	NPC68565
0.6494	Remote Similarity	NPC132064
0.6494	Remote Similarity	NPC179858
0.6494	Remote Similarity	NPC35871
0.6486	Remote Similarity	NPC469941
0.6486	Remote Similarity	NPC319671
0.6486	Remote Similarity	NPC28526
0.6486	Remote Similarity	NPC252032
0.6486	Remote Similarity	NPC476734
0.6486	Remote Similarity	NPC107130

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 NPC474552 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	467
0.1-0.2	3713
0.2-0.3	3162
0.3-0.4	1036
0.4-0.5	538
0.5-0.6	200
0.6-0.7	31
0.7-0.8	3
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
0.7705	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7909	Approved
0.7385	Intermediate Similarity	NPD3198	Approved
0.7241	Intermediate Similarity	NPD634	Phase 3
0.7143	Intermediate Similarity	NPD615	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4802	Phase 2
0.7105	Intermediate Similarity	NPD4238	Approved
0.7097	Intermediate Similarity	NPD3186	Phase 1
0.6875	Remote Similarity	NPD3728	Approved
0.6875	Remote Similarity	NPD3730	Approved
0.6753	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD9638	Phase 2
0.6623	Remote Similarity	NPD6117	Approved
0.6579	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2270	Approved
0.65	Remote Similarity	NPD2699	Approved
0.6494	Remote Similarity	NPD3702	Approved
0.6456	Remote Similarity	NPD6114	Approved
0.6456	Remote Similarity	NPD6118	Approved
0.6456	Remote Similarity	NPD6697	Approved
0.6456	Remote Similarity	NPD6115	Approved
0.6452	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2266	Phase 2
0.642	Remote Similarity	NPD5369	Approved
0.6395	Remote Similarity	NPD6101	Approved
0.6395	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD229	Approved
0.6316	Remote Similarity	NPD6081	Approved
0.6301	Remote Similarity	NPD4224	Phase 2
0.6296	Remote Similarity	NPD5368	Approved
0.625	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.623	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD77	Approved
0.6207	Remote Similarity	NPD9448	Phase 2
0.6207	Remote Similarity	NPD9655	Approved
0.6207	Remote Similarity	NPD633	Phase 3
0.6207	Remote Similarity	NPD9450	Approved
0.6184	Remote Similarity	NPD4244	Approved
0.6184	Remote Similarity	NPD4245	Approved
0.6167	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD7341	Phase 2
0.6145	Remote Similarity	NPD4269	Approved
0.6145	Remote Similarity	NPD7345	Approved
0.6145	Remote Similarity	NPD4270	Approved
0.6145	Remote Similarity	NPD6435	Approved
0.6104	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD5777	Approved
0.6098	Remote Similarity	NPD4820	Approved
0.6098	Remote Similarity	NPD4822	Approved
0.6098	Remote Similarity	NPD4819	Approved
0.6098	Remote Similarity	NPD4821	Approved
0.6053	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3698	Phase 2
0.6034	Remote Similarity	NPD3206	Approved
0.6	Remote Similarity	NPD8084	Approved
0.6	Remote Similarity	NPD8085	Approved
0.6	Remote Similarity	NPD8082	Approved
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD8086	Approved
0.6	Remote Similarity	NPD5778	Approved
0.6	Remote Similarity	NPD8138	Approved
0.6	Remote Similarity	NPD8139	Approved
0.6	Remote Similarity	NPD8083	Approved
0.5974	Remote Similarity	NPD4789	Approved
0.5955	Remote Similarity	NPD46	Approved
0.5955	Remote Similarity	NPD6698	Approved
0.5942	Remote Similarity	NPD73	Approved
0.5938	Remote Similarity	NPD8275	Approved
0.5938	Remote Similarity	NPD8276	Approved
0.593	Remote Similarity	NPD5363	Approved
0.5921	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD5360	Phase 3
0.5904	Remote Similarity	NPD4252	Approved
0.5889	Remote Similarity	NPD7983	Approved
0.5882	Remote Similarity	NPD7154	Phase 3
0.5882	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3669	Approved
0.5876	Remote Similarity	NPD8081	Approved
0.5875	Remote Similarity	NPD2257	Approved
0.5862	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5786	Approved
0.5854	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4271	Approved
0.5854	Remote Similarity	NPD4268	Approved
0.5833	Remote Similarity	NPD1780	Approved
0.5833	Remote Similarity	NPD1779	Approved
0.5816	Remote Similarity	NPD8393	Approved
0.5806	Remote Similarity	NPD7839	Suspended
0.5781	Remote Similarity	NPD385	Approved
0.5781	Remote Similarity	NPD384	Approved
0.5769	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD5282	Discontinued
0.5758	Remote Similarity	NPD8140	Approved
0.5758	Remote Similarity	NPD8307	Discontinued
0.5753	Remote Similarity	NPD9676	Phase 3
0.5747	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.573	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8034	Phase 2
0.5714	Remote Similarity	NPD8035	Phase 2
0.5714	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD5362	Discontinued
0.5679	Remote Similarity	NPD3703	Phase 2
0.5663	Remote Similarity	NPD3732	Approved
0.5658	Remote Similarity	NPD7331	Phase 2
0.5652	Remote Similarity	NPD6399	Phase 3
0.5645	Remote Similarity	NPD1462	Approved
0.5644	Remote Similarity	NPD8306	Approved
0.5644	Remote Similarity	NPD8305	Approved
0.5641	Remote Similarity	NPD3725	Approved
0.5641	Remote Similarity	NPD3726	Approved
0.5634	Remote Similarity	NPD9438	Approved
0.5634	Remote Similarity	NPD9439	Approved
0.5634	Remote Similarity	NPD8959	Approved
0.5625	Remote Similarity	NPD386	Approved
0.5625	Remote Similarity	NPD388	Approved
0.5616	Remote Similarity	NPD9656	Approved
0.5604	Remote Similarity	NPD5785	Approved
0.56	Remote Similarity	NPD3197	Phase 1
0.56	Remote Similarity	NPD371	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