NPASS Compound

Structure

NPC71079 OpenBabel07101719142D 34 35 0 0 1 0 0 0 0 0999 V2000 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -5.5000 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 6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -5.5000 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 11.2583 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 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 9.5263 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 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 0.8660 -1.5000 0.0000 C 0 0 2 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 10.3923 -4.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 33 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 21 1 0 0 0 0 16 21 1 0 0 0 0 17 27 2 0 0 0 0 18 28 1 0 0 0 0 19 21 2 0 0 0 0 19 27 1 0 0 0 0 20 29 1 0 0 0 0 22 20 1 6 0 0 0 22 23 1 0 0 0 0 22 34 1 0 0 0 0 23 24 1 0 0 0 0 23 30 1 1 0 0 0 24 25 1 0 0 0 0 24 31 1 6 0 0 0 25 26 1 0 0 0 0 25 32 1 1 0 0 0 26 28 1 6 0 0 0 26 34 1 0 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.19
Volume:	391.582
LogP:	2.248
LogD:	2.749
LogS:	-3.592
# Rotatable Bonds:	11
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	2.629
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.486
MDCK Permeability:	5.249829700915143e-05
Pgp-inhibitor:	0.976
Pgp-substrate:	0.043
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.367
Plasma Protein Binding (PPB):	73.54145050048828%
Volume Distribution (VD):	0.58
Pgp-substrate:	7.584928035736084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.359
CYP1A2-substrate:	0.82
CYP2C19-inhibitor:	0.458
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.16
CYP2C9-substrate:	0.744
CYP2D6-inhibitor:	0.721
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.663

ADMET: Excretion

Clearance (CL):	9.212
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.273
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.391
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.349
Skin Sensitization:	0.713
Carcinogencity:	0.479
Eye Corrosion:	0.003
Eye Irritation:	0.046
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC71079

Natural Product ID:	NPC71079
*Common Name:**	Amphimedoside E
IUPAC Name:	(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[methoxy-[(Z)-14-pyridin-3-yltetradec-5-enyl]amino]oxane-3,4,5-triol
Synonyms:	Amphimedoside E
Standard InCHIKey:	YPJONPXFFNCTJJ-OGUBVRRVSA-N
Standard InCHI:	InChI=1S/C26H44N2O6/c1-33-28(26-25(32)24(31)23(30)22(20-29)34-26)18-13-11-9-7-5-3-2-4-6-8-10-12-15-21-16-14-17-27-19-21/h5,7,14,16-17,19,22-26,29-32H,2-4,6,8-13,15,18,20H2,1H3/b7-5-/t22-,23-,24+,25-,26-/m1/s1
SMILES:	CON([C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)CCCC/C=CCCCCCCCCc1cccnc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465624
PubChem CID:	16091665
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002203] Glycosylamines

*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
NPO33243	Amphimedon sp.	Species	Niphatidae	Eukaryota	n.a.	Iojima Island, the Satsunan Islands, southern Japan (3047 N; 13017 E)	n.a.	PMID[15497958]
NPO33243	Amphimedon sp.	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067172]
NPO33243	Amphimedon sp.	Species	Niphatidae	Eukaryota	n.a.	Republic of Palau	2006; 2007	PMID[20681583]
NPO33243	Amphimedon sp.	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28207259]
NPO33243	Amphimedon sp.	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7714542]
NPO33243	Amphimedon sp.	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599281]

☑ 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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	2.2	ug.mL-1	PMID[475113]

☑ 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 NPC71079 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	242
0.1-0.2	1244
0.2-0.3	9375
0.3-0.4	21367
0.4-0.5	6428
0.5-0.6	2878
0.6-0.7	1072
0.7-0.8	85
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC474217
0.9801	High Similarity	NPC278366
0.9801	High Similarity	NPC127730
0.9735	High Similarity	NPC85918
0.8246	Intermediate Similarity	NPC62510
0.8199	Intermediate Similarity	NPC138018
0.7867	Intermediate Similarity	NPC471311
0.7867	Intermediate Similarity	NPC471313
0.7857	Intermediate Similarity	NPC319456
0.7838	Intermediate Similarity	NPC290094
0.7747	Intermediate Similarity	NPC149708
0.7697	Intermediate Similarity	NPC89490
0.7688	Intermediate Similarity	NPC471323
0.7682	Intermediate Similarity	NPC202957
0.7682	Intermediate Similarity	NPC169625
0.7647	Intermediate Similarity	NPC329896
0.7647	Intermediate Similarity	NPC475090
0.7647	Intermediate Similarity	NPC475105
0.764	Intermediate Similarity	NPC328798
0.7614	Intermediate Similarity	NPC325093
0.7574	Intermediate Similarity	NPC476446
0.7574	Intermediate Similarity	NPC78375
0.7574	Intermediate Similarity	NPC469813
0.7542	Intermediate Similarity	NPC325775
0.7528	Intermediate Similarity	NPC318020
0.7514	Intermediate Similarity	NPC327373
0.7514	Intermediate Similarity	NPC322043
0.75	Intermediate Similarity	NPC182814
0.7486	Intermediate Similarity	NPC20593
0.7436	Intermediate Similarity	NPC324611
0.7427	Intermediate Similarity	NPC477975
0.7421	Intermediate Similarity	NPC471312
0.7418	Intermediate Similarity	NPC127647
0.7401	Intermediate Similarity	NPC317010
0.7326	Intermediate Similarity	NPC160127
0.7326	Intermediate Similarity	NPC50997
0.7325	Intermediate Similarity	NPC256893
0.729	Intermediate Similarity	NPC212125
0.729	Intermediate Similarity	NPC165370
0.7267	Intermediate Similarity	NPC40779
0.7261	Intermediate Similarity	NPC315320
0.7254	Intermediate Similarity	NPC472752
0.7247	Intermediate Similarity	NPC133261
0.7234	Intermediate Similarity	NPC474767
0.7232	Intermediate Similarity	NPC203754
0.7232	Intermediate Similarity	NPC472122
0.7232	Intermediate Similarity	NPC24594
0.7232	Intermediate Similarity	NPC150048
0.7225	Intermediate Similarity	NPC471178
0.7208	Intermediate Similarity	NPC476322
0.72	Intermediate Similarity	NPC471402
0.72	Intermediate Similarity	NPC297486
0.72	Intermediate Similarity	NPC240136
0.7188	Intermediate Similarity	NPC309498
0.7184	Intermediate Similarity	NPC108469
0.7168	Intermediate Similarity	NPC311276
0.7151	Intermediate Similarity	NPC141377
0.7143	Intermediate Similarity	NPC29702
0.7143	Intermediate Similarity	NPC292517
0.7135	Intermediate Similarity	NPC473763
0.7135	Intermediate Similarity	NPC129721
0.7135	Intermediate Similarity	NPC117244
0.7111	Intermediate Similarity	NPC472105
0.7111	Intermediate Similarity	NPC187827
0.7107	Intermediate Similarity	NPC471322
0.7105	Intermediate Similarity	NPC79223
0.7095	Intermediate Similarity	NPC326575
0.709	Intermediate Similarity	NPC470499
0.709	Intermediate Similarity	NPC59033
0.7078	Intermediate Similarity	NPC329825
0.7074	Intermediate Similarity	NPC292361
0.7072	Intermediate Similarity	NPC470474
0.707	Intermediate Similarity	NPC306397
0.7069	Intermediate Similarity	NPC473057
0.7068	Intermediate Similarity	NPC328559
0.7068	Intermediate Similarity	NPC32451
0.7062	Intermediate Similarity	NPC470498
0.7059	Intermediate Similarity	NPC289786
0.7056	Intermediate Similarity	NPC476467
0.7047	Intermediate Similarity	NPC25442
0.7047	Intermediate Similarity	NPC12944
0.7044	Intermediate Similarity	NPC69914
0.7039	Intermediate Similarity	NPC91958
0.7037	Intermediate Similarity	NPC329024
0.7035	Intermediate Similarity	NPC469762
0.7035	Intermediate Similarity	NPC30570
0.7033	Intermediate Similarity	NPC472110
0.7033	Intermediate Similarity	NPC472109
0.7031	Intermediate Similarity	NPC476874
0.7026	Intermediate Similarity	NPC63041
0.7022	Intermediate Similarity	NPC314603
0.7016	Intermediate Similarity	NPC470497
0.7011	Intermediate Similarity	NPC124542
0.7011	Intermediate Similarity	NPC59779
0.7011	Intermediate Similarity	NPC471177
0.7	Intermediate Similarity	NPC162812
0.7	Intermediate Similarity	NPC317672
0.7	Intermediate Similarity	NPC324245
0.7	Intermediate Similarity	NPC320748
0.7	Intermediate Similarity	NPC153769
0.699	Remote Similarity	NPC48042
0.699	Remote Similarity	NPC304179
0.699	Remote Similarity	NPC472550
0.6989	Remote Similarity	NPC160105
0.6989	Remote Similarity	NPC98187
0.6989	Remote Similarity	NPC54988
0.6985	Remote Similarity	NPC313640
0.6981	Remote Similarity	NPC476131
0.6977	Remote Similarity	NPC469785
0.6974	Remote Similarity	NPC156044
0.697	Remote Similarity	NPC472553
0.6966	Remote Similarity	NPC89562
0.6959	Remote Similarity	NPC27802
0.6957	Remote Similarity	NPC188387
0.6957	Remote Similarity	NPC322488
0.6957	Remote Similarity	NPC163421
0.695	Remote Similarity	NPC477910
0.6943	Remote Similarity	NPC146373
0.6943	Remote Similarity	NPC245244
0.6943	Remote Similarity	NPC166424
0.694	Remote Similarity	NPC139291
0.694	Remote Similarity	NPC472108
0.694	Remote Similarity	NPC469358
0.6936	Remote Similarity	NPC132680
0.6936	Remote Similarity	NPC269919
0.6931	Remote Similarity	NPC472555
0.6923	Remote Similarity	NPC477974
0.6919	Remote Similarity	NPC63562
0.6915	Remote Similarity	NPC471014
0.6915	Remote Similarity	NPC475408
0.6915	Remote Similarity	NPC206343
0.6915	Remote Similarity	NPC477908
0.6903	Remote Similarity	NPC48564
0.6903	Remote Similarity	NPC182570
0.6903	Remote Similarity	NPC265605
0.6902	Remote Similarity	NPC207851
0.6893	Remote Similarity	NPC474561
0.6893	Remote Similarity	NPC49954
0.6884	Remote Similarity	NPC111732
0.6881	Remote Similarity	NPC314270
0.6881	Remote Similarity	NPC294579
0.6881	Remote Similarity	NPC144779
0.6875	Remote Similarity	NPC263439
0.6875	Remote Similarity	NPC97367
0.6866	Remote Similarity	NPC470306
0.6864	Remote Similarity	NPC161292
0.686	Remote Similarity	NPC73952
0.686	Remote Similarity	NPC469763
0.686	Remote Similarity	NPC25008
0.686	Remote Similarity	NPC469765
0.686	Remote Similarity	NPC476492
0.686	Remote Similarity	NPC469760
0.686	Remote Similarity	NPC259644
0.686	Remote Similarity	NPC469786
0.6857	Remote Similarity	NPC63338
0.6857	Remote Similarity	NPC324203
0.6857	Remote Similarity	NPC322976
0.6855	Remote Similarity	NPC278451
0.6848	Remote Similarity	NPC163055
0.6833	Remote Similarity	NPC477976
0.6832	Remote Similarity	NPC471016
0.6832	Remote Similarity	NPC6981
0.6831	Remote Similarity	NPC471997
0.6829	Remote Similarity	NPC477911
0.6821	Remote Similarity	NPC211572
0.6821	Remote Similarity	NPC80597
0.6821	Remote Similarity	NPC70922
0.6821	Remote Similarity	NPC212376
0.6821	Remote Similarity	NPC75540
0.6818	Remote Similarity	NPC282231
0.6818	Remote Similarity	NPC143603
0.6816	Remote Similarity	NPC228331
0.6816	Remote Similarity	NPC319128
0.6811	Remote Similarity	NPC284559
0.6809	Remote Similarity	NPC95783
0.6802	Remote Similarity	NPC475835
0.68	Remote Similarity	NPC230869
0.6798	Remote Similarity	NPC62367
0.6796	Remote Similarity	NPC469938
0.6793	Remote Similarity	NPC233936
0.6789	Remote Similarity	NPC279401
0.6789	Remote Similarity	NPC79293
0.6786	Remote Similarity	NPC118832
0.6786	Remote Similarity	NPC165349
0.6786	Remote Similarity	NPC329708
0.6786	Remote Similarity	NPC274291
0.6786	Remote Similarity	NPC264166
0.6786	Remote Similarity	NPC47059
0.6782	Remote Similarity	NPC477909
0.6782	Remote Similarity	NPC42678
0.6782	Remote Similarity	NPC477907
0.678	Remote Similarity	NPC194640
0.6779	Remote Similarity	NPC244536
0.6778	Remote Similarity	NPC158129
0.6769	Remote Similarity	NPC193761
0.6766	Remote Similarity	NPC165837
0.6765	Remote Similarity	NPC301368
0.6765	Remote Similarity	NPC84815
0.6765	Remote Similarity	NPC216428
0.6763	Remote Similarity	NPC475498

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 NPC71079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	477
0.2-0.3	783
0.3-0.4	1612
0.4-0.5	3458
0.5-0.6	2119
0.6-0.7	502
0.7-0.8	47
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7935	Intermediate Similarity	NPD1380	Discovery
0.7853	Intermediate Similarity	NPD2544	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD4239	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1383	Phase 3
0.7785	Intermediate Similarity	NPD1382	Phase 2
0.7644	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8408	Discontinued
0.7542	Intermediate Similarity	NPD8021	Approved
0.7542	Intermediate Similarity	NPD8020	Approved
0.7532	Intermediate Similarity	NPD9506	Approved
0.7486	Intermediate Similarity	NPD8123	Approved
0.7486	Intermediate Similarity	NPD8122	Approved
0.7484	Intermediate Similarity	NPD2896	Discontinued
0.7469	Intermediate Similarity	NPD3813	Approved
0.7459	Intermediate Similarity	NPD8063	Discontinued
0.7442	Intermediate Similarity	NPD5862	Discovery
0.7439	Intermediate Similarity	NPD4702	Approved
0.7439	Intermediate Similarity	NPD4703	Approved
0.7425	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2809	Approved
0.7407	Intermediate Similarity	NPD3717	Discontinued
0.7396	Intermediate Similarity	NPD5255	Approved
0.7381	Intermediate Similarity	NPD6026	Approved
0.7362	Intermediate Similarity	NPD1352	Discontinued
0.7353	Intermediate Similarity	NPD2511	Approved
0.7346	Intermediate Similarity	NPD4805	Approved
0.7337	Intermediate Similarity	NPD2582	Approved
0.7337	Intermediate Similarity	NPD2581	Approved
0.731	Intermediate Similarity	NPD8026	Phase 1
0.7297	Intermediate Similarity	NPD4427	Phase 2
0.729	Intermediate Similarity	NPD9284	Approved
0.7288	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1649	Discontinued
0.7262	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD9207	Approved
0.7261	Intermediate Similarity	NPD9206	Approved
0.7244	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4804	Approved
0.7184	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6635	Approved
0.7168	Intermediate Similarity	NPD5088	Discontinued
0.7152	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7913	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2119	Approved
0.707	Intermediate Similarity	NPD9080	Approved
0.707	Intermediate Similarity	NPD2118	Approved
0.7066	Intermediate Similarity	NPD7469	Discontinued
0.7063	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3082	Discontinued
0.7045	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD2076	Approved
0.7022	Intermediate Similarity	NPD2077	Approved
0.7	Intermediate Similarity	NPD3262	Approved
0.7	Intermediate Similarity	NPD8325	Phase 3
0.7	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8326	Phase 3
0.697	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4529	Approved
0.6968	Remote Similarity	NPD4528	Approved
0.6968	Remote Similarity	NPD4526	Approved
0.6957	Remote Similarity	NPD6227	Discontinued
0.6952	Remote Similarity	NPD4699	Discontinued
0.6943	Remote Similarity	NPD5486	Discontinued
0.6937	Remote Similarity	NPD3475	Approved
0.6937	Remote Similarity	NPD3476	Approved
0.6936	Remote Similarity	NPD9383	Approved
0.6936	Remote Similarity	NPD9382	Approved
0.6935	Remote Similarity	NPD4021	Phase 2
0.6923	Remote Similarity	NPD1661	Suspended
0.6914	Remote Similarity	NPD3944	Approved
0.6914	Remote Similarity	NPD3942	Approved
0.6906	Remote Similarity	NPD1032	Phase 2
0.6903	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD268	Approved
0.6903	Remote Similarity	NPD271	Approved
0.6889	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3575	Approved
0.6882	Remote Similarity	NPD3576	Approved
0.6875	Remote Similarity	NPD8129	Discovery
0.6872	Remote Similarity	NPD7396	Approved
0.6869	Remote Similarity	NPD8321	Discontinued
0.6867	Remote Similarity	NPD4824	Approved
0.6867	Remote Similarity	NPD4823	Approved
0.6857	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4640	Approved
0.6854	Remote Similarity	NPD4638	Approved
0.6854	Remote Similarity	NPD4639	Approved
0.6852	Remote Similarity	NPD1993	Approved
0.6852	Remote Similarity	NPD1995	Approved
0.6852	Remote Similarity	NPD1994	Approved
0.6851	Remote Similarity	NPD5100	Phase 3
0.6851	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7234	Approved
0.6845	Remote Similarity	NPD7233	Approved
0.6842	Remote Similarity	NPD7944	Discontinued
0.6839	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5458	Discontinued
0.6829	Remote Similarity	NPD792	Discontinued
0.6828	Remote Similarity	NPD4375	Approved
0.6825	Remote Similarity	NPD6569	Phase 2
0.6818	Remote Similarity	NPD6529	Discontinued
0.681	Remote Similarity	NPD4029	Approved
0.681	Remote Similarity	NPD4030	Approved
0.681	Remote Similarity	NPD4028	Approved
0.6809	Remote Similarity	NPD3321	Discontinued
0.6792	Remote Similarity	NPD9583	Approved
0.679	Remote Similarity	NPD9726	Discontinued
0.6786	Remote Similarity	NPD4035	Approved
0.6786	Remote Similarity	NPD31	Approved
0.6786	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4122	Approved
0.6786	Remote Similarity	NPD4039	Approved
0.6786	Remote Similarity	NPD4036	Approved
0.6786	Remote Similarity	NPD4037	Approved
0.6786	Remote Similarity	NPD4038	Approved
0.6786	Remote Similarity	NPD4034	Approved
0.6786	Remote Similarity	NPD3525	Discontinued
0.6786	Remote Similarity	NPD4033	Approved
0.6786	Remote Similarity	NPD32	Approved
0.678	Remote Similarity	NPD6298	Discontinued
0.6779	Remote Similarity	NPD4086	Phase 1
0.6778	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6241	Phase 1
0.6772	Remote Similarity	NPD6626	Approved
0.6765	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6068	Discontinued
0.6751	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.675	Remote Similarity	NPD992	Clinical (unspecified phase)
0.675	Remote Similarity	NPD991	Phase 2
0.6743	Remote Similarity	NPD820	Phase 3
0.6739	Remote Similarity	NPD6595	Phase 3
0.6732	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD715	Phase 3
0.6725	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD4072	Approved
0.6721	Remote Similarity	NPD4071	Approved
0.6717	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD5611	Phase 2
0.6703	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3386	Phase 2
0.6702	Remote Similarity	NPD1034	Phase 3
0.6702	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4551	Phase 2
0.6699	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2123	Phase 3
0.6684	Remote Similarity	NPD5555	Phase 1
0.6684	Remote Similarity	NPD1229	Phase 2
0.6682	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9357	Approved
0.6667	Remote Similarity	NPD6363	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5596	Phase 2
0.6667	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD925	Approved
0.6648	Remote Similarity	NPD926	Approved
0.6646	Remote Similarity	NPD1598	Discontinued
0.6632	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD1096	Discontinued
0.663	Remote Similarity	NPD2620	Phase 2
0.663	Remote Similarity	NPD4973	Approved
0.663	Remote Similarity	NPD2619	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD2061	Approved
0.6628	Remote Similarity	NPD1270	Approved
0.662	Remote Similarity	NPD7558	Phase 2
0.6616	Remote Similarity	NPD8169	Discontinued
0.6615	Remote Similarity	NPD6361	Phase 2
0.6615	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD2928	Phase 2
0.661	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD510	Phase 1
0.6609	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2075	Approved
0.6607	Remote Similarity	NPD2071	Approved
0.6607	Remote Similarity	NPD2073	Approved
0.6607	Remote Similarity	NPD2069	Approved
0.6607	Remote Similarity	NPD2068	Approved
0.6607	Remote Similarity	NPD2072	Approved
0.6607	Remote Similarity	NPD2070	Approved
0.6607	Remote Similarity	NPD2074	Approved
0.6599	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD2952	Discontinued

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