NPASS Compound

Structure

NPC85918 OpenBabel07101718292D 34 35 0 0 1 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 3.0000 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 15.5885 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7224 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5885 4.0000 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 13.8564 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 3.0000 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 0.8660 -1.5000 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 1.7321 -0.0000 0.0000 C 0 0 2 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 14.7224 4.5000 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 -0.8660 -2.5000 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 2.5981 -1.5000 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 0.0000 2.0000 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 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 3 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 1 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 6 0 0 0 24 25 1 0 0 0 0 24 31 1 1 0 0 0 25 26 1 0 0 0 0 25 32 1 6 0 0 0 26 28 1 1 0 0 0 26 34 1 0 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.3
Volume:	502.692
LogP:	2.573
LogD:	2.918
LogS:	-3.093
# Rotatable Bonds:	15
TPSA:	115.51
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.172
Synthetic Accessibility Score:	4.235
Fsp3:	0.731
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.089
MDCK Permeability:	3.6231300327926874e-05
Pgp-inhibitor:	0.911
Pgp-substrate:	0.412
Human Intestinal Absorption (HIA):	0.726
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	92.33213806152344%
Volume Distribution (VD):	0.551
Pgp-substrate:	2.3114078044891357%

ADMET: Metabolism

CYP1A2-inhibitor:	0.267
CYP1A2-substrate:	0.476
CYP2C19-inhibitor:	0.577
CYP2C19-substrate:	0.282
CYP2C9-inhibitor:	0.649
CYP2C9-substrate:	0.843
CYP2D6-inhibitor:	0.524
CYP2D6-substrate:	0.252
CYP3A4-inhibitor:	0.87
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	7.041
Half-life (T1/2):	0.801

ADMET: Toxicity

hERG Blockers:	0.429
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.942
Carcinogencity:	0.059
Eye Corrosion:	0.008
Eye Irritation:	0.104
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC85918

Natural Product ID:	NPC85918
*Common Name:**	Amphimedoside C
IUPAC Name:	(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[methoxy(14-pyridin-3-yltetradec-11-ynyl)amino]oxane-3,4,5-triol
Synonyms:	Amphimedoside C
Standard InCHIKey:	MOBUBNOVPKQFNY-WSGIOKLISA-N
Standard InCHI:	InChI=1S/C26H42N2O6/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/h14,16-17,19,22-26,29-32H,2-7,9,11-13,15,18,20H2,1H3/t22-,23-,24+,25-,26-/m1/s1
SMILES:	CON(CCCCCCCCCCC#CCCc1cccnc1)[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463595
PubChem CID:	16091664
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	=	5.0	ug.mL-1	PMID[525330]

☑ 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 NPC85918 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	245
0.1-0.2	1353
0.2-0.3	11193
0.3-0.4	20451
0.4-0.5	5788
0.5-0.6	2734
0.6-0.7	873
0.7-0.8	55
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC127730
0.9934	High Similarity	NPC278366
0.9735	High Similarity	NPC71079
0.9671	High Similarity	NPC474217
0.8098	Intermediate Similarity	NPC138018
0.8046	Intermediate Similarity	NPC62510
0.7815	Intermediate Similarity	NPC169625
0.7815	Intermediate Similarity	NPC202957
0.7765	Intermediate Similarity	NPC319456
0.7763	Intermediate Similarity	NPC471313
0.7763	Intermediate Similarity	NPC471311
0.7616	Intermediate Similarity	NPC290094
0.7593	Intermediate Similarity	NPC471323
0.7568	Intermediate Similarity	NPC149708
0.7556	Intermediate Similarity	NPC328798
0.7528	Intermediate Similarity	NPC325093
0.7484	Intermediate Similarity	NPC89490
0.7459	Intermediate Similarity	NPC325775
0.7444	Intermediate Similarity	NPC318020
0.7436	Intermediate Similarity	NPC329896
0.7436	Intermediate Similarity	NPC475090
0.7436	Intermediate Similarity	NPC475105
0.743	Intermediate Similarity	NPC322043
0.743	Intermediate Similarity	NPC327373
0.7418	Intermediate Similarity	NPC182814
0.7405	Intermediate Similarity	NPC20593
0.7384	Intermediate Similarity	NPC469813
0.7384	Intermediate Similarity	NPC78375
0.7384	Intermediate Similarity	NPC476446
0.7342	Intermediate Similarity	NPC324611
0.7337	Intermediate Similarity	NPC127647
0.7329	Intermediate Similarity	NPC471312
0.7318	Intermediate Similarity	NPC317010
0.7249	Intermediate Similarity	NPC160127
0.7249	Intermediate Similarity	NPC50997
0.7241	Intermediate Similarity	NPC477975
0.7197	Intermediate Similarity	NPC165370
0.7197	Intermediate Similarity	NPC212125
0.717	Intermediate Similarity	NPC315320
0.7158	Intermediate Similarity	NPC474767
0.7125	Intermediate Similarity	NPC256893
0.7115	Intermediate Similarity	NPC476322
0.7113	Intermediate Similarity	NPC309498
0.7092	Intermediate Similarity	NPC472752
0.7086	Intermediate Similarity	NPC40779
0.7072	Intermediate Similarity	NPC133261
0.7056	Intermediate Similarity	NPC203754
0.7056	Intermediate Similarity	NPC472122
0.7056	Intermediate Similarity	NPC24594
0.7056	Intermediate Similarity	NPC150048
0.7055	Intermediate Similarity	NPC29702
0.7045	Intermediate Similarity	NPC471178
0.7031	Intermediate Similarity	NPC79223
0.7019	Intermediate Similarity	NPC471322
0.7016	Intermediate Similarity	NPC59033
0.7006	Intermediate Similarity	NPC108469
0.6995	Remote Similarity	NPC328559
0.6995	Remote Similarity	NPC32451
0.6993	Remote Similarity	NPC297486
0.6993	Remote Similarity	NPC471402
0.6993	Remote Similarity	NPC240136
0.6989	Remote Similarity	NPC311276
0.6985	Remote Similarity	NPC292517
0.6981	Remote Similarity	NPC306397
0.6978	Remote Similarity	NPC141377
0.6974	Remote Similarity	NPC25442
0.6974	Remote Similarity	NPC12944
0.6968	Remote Similarity	NPC473763
0.6968	Remote Similarity	NPC117244
0.6963	Remote Similarity	NPC329024
0.6954	Remote Similarity	NPC129721
0.694	Remote Similarity	NPC187827
0.694	Remote Similarity	NPC472105
0.6927	Remote Similarity	NPC317672
0.6927	Remote Similarity	NPC320748
0.6927	Remote Similarity	NPC324245
0.6927	Remote Similarity	NPC470499
0.6923	Remote Similarity	NPC326575
0.6919	Remote Similarity	NPC153769
0.6911	Remote Similarity	NPC292361
0.6904	Remote Similarity	NPC156044
0.6902	Remote Similarity	NPC470474
0.69	Remote Similarity	NPC476467
0.6895	Remote Similarity	NPC289786
0.6894	Remote Similarity	NPC476131
0.6893	Remote Similarity	NPC473057
0.6889	Remote Similarity	NPC470498
0.6881	Remote Similarity	NPC30570
0.6879	Remote Similarity	NPC329825
0.6872	Remote Similarity	NPC476874
0.6871	Remote Similarity	NPC322488
0.6869	Remote Similarity	NPC63041
0.6867	Remote Similarity	NPC27802
0.6865	Remote Similarity	NPC472109
0.6865	Remote Similarity	NPC472110
0.6857	Remote Similarity	NPC269919
0.6857	Remote Similarity	NPC132680
0.6857	Remote Similarity	NPC469762
0.6856	Remote Similarity	NPC470497
0.6852	Remote Similarity	NPC69914
0.6851	Remote Similarity	NPC314603
0.6847	Remote Similarity	NPC162812
0.6839	Remote Similarity	NPC63562
0.6839	Remote Similarity	NPC91958
0.6836	Remote Similarity	NPC59779
0.6836	Remote Similarity	NPC124542
0.6836	Remote Similarity	NPC471177
0.6834	Remote Similarity	NPC304179
0.6834	Remote Similarity	NPC48042
0.6834	Remote Similarity	NPC472550
0.6832	Remote Similarity	NPC313640
0.6816	Remote Similarity	NPC54988
0.6816	Remote Similarity	NPC111732
0.6816	Remote Similarity	NPC472553
0.6816	Remote Similarity	NPC160105
0.6816	Remote Similarity	NPC98187
0.6815	Remote Similarity	NPC265605
0.6815	Remote Similarity	NPC48564
0.6815	Remote Similarity	NPC182570
0.68	Remote Similarity	NPC469785
0.6798	Remote Similarity	NPC477910
0.6798	Remote Similarity	NPC263439
0.6796	Remote Similarity	NPC89562
0.6791	Remote Similarity	NPC163421
0.6791	Remote Similarity	NPC188387
0.6784	Remote Similarity	NPC161292
0.678	Remote Similarity	NPC63338
0.678	Remote Similarity	NPC472555
0.678	Remote Similarity	NPC324203
0.678	Remote Similarity	NPC322976
0.6774	Remote Similarity	NPC472108
0.6774	Remote Similarity	NPC139291
0.6774	Remote Similarity	NPC469358
0.6765	Remote Similarity	NPC475408
0.6765	Remote Similarity	NPC471014
0.6765	Remote Similarity	NPC206343
0.6765	Remote Similarity	NPC477908
0.675	Remote Similarity	NPC245244
0.675	Remote Similarity	NPC166424
0.675	Remote Similarity	NPC146373
0.6744	Remote Similarity	NPC477974
0.6738	Remote Similarity	NPC207851
0.6738	Remote Similarity	NPC284559
0.6732	Remote Similarity	NPC294579
0.6732	Remote Similarity	NPC144779
0.6732	Remote Similarity	NPC314270
0.6731	Remote Similarity	NPC143603
0.6722	Remote Similarity	NPC49954
0.6722	Remote Similarity	NPC474561
0.6721	Remote Similarity	NPC469938
0.6716	Remote Similarity	NPC470306
0.6714	Remote Similarity	NPC476492
0.6704	Remote Similarity	NPC97367
0.6686	Remote Similarity	NPC469760
0.6686	Remote Similarity	NPC25008
0.6686	Remote Similarity	NPC73952
0.6686	Remote Similarity	NPC259644
0.6686	Remote Similarity	NPC469763
0.6686	Remote Similarity	NPC469765
0.6686	Remote Similarity	NPC469786
0.6684	Remote Similarity	NPC163055
0.6683	Remote Similarity	NPC6981
0.6683	Remote Similarity	NPC471016
0.6683	Remote Similarity	NPC477911
0.6667	Remote Similarity	NPC477976
0.6667	Remote Similarity	NPC319128
0.6667	Remote Similarity	NPC76540
0.6667	Remote Similarity	NPC278451
0.6667	Remote Similarity	NPC471997
0.6667	Remote Similarity	NPC228331
0.665	Remote Similarity	NPC62367
0.665	Remote Similarity	NPC475835
0.6649	Remote Similarity	NPC95783
0.6648	Remote Similarity	NPC211572
0.6648	Remote Similarity	NPC75540
0.6648	Remote Similarity	NPC80597
0.6648	Remote Similarity	NPC70922
0.6648	Remote Similarity	NPC282231
0.6648	Remote Similarity	NPC263455
0.6648	Remote Similarity	NPC212376
0.6635	Remote Similarity	NPC244536
0.6634	Remote Similarity	NPC42678
0.6634	Remote Similarity	NPC477907
0.6634	Remote Similarity	NPC477909
0.6633	Remote Similarity	NPC118832
0.6633	Remote Similarity	NPC165349
0.6633	Remote Similarity	NPC47059
0.6633	Remote Similarity	NPC274291
0.6633	Remote Similarity	NPC329708
0.6633	Remote Similarity	NPC264166
0.6632	Remote Similarity	NPC279401
0.6632	Remote Similarity	NPC79293
0.6631	Remote Similarity	NPC233936
0.6629	Remote Similarity	NPC230869
0.6619	Remote Similarity	NPC477902
0.6619	Remote Similarity	NPC475498
0.6619	Remote Similarity	NPC475137
0.6618	Remote Similarity	NPC165837
0.6618	Remote Similarity	NPC301368
0.6618	Remote Similarity	NPC216428

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 NPC85918 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	495
0.2-0.3	859
0.3-0.4	1731
0.4-0.5	3547
0.5-0.6	1926
0.6-0.7	406
0.7-0.8	33
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
0.7834	Intermediate Similarity	NPD1380	Discovery
0.7765	Intermediate Similarity	NPD2544	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD4239	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1383	Phase 3
0.7688	Intermediate Similarity	NPD1382	Phase 2
0.7557	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD9506	Approved
0.7374	Intermediate Similarity	NPD8408	Discontinued
0.7363	Intermediate Similarity	NPD8020	Approved
0.7363	Intermediate Similarity	NPD8021	Approved
0.7303	Intermediate Similarity	NPD8122	Approved
0.7303	Intermediate Similarity	NPD8123	Approved
0.7284	Intermediate Similarity	NPD2896	Discontinued
0.7283	Intermediate Similarity	NPD8063	Discontinued
0.7273	Intermediate Similarity	NPD1352	Discontinued
0.7273	Intermediate Similarity	NPD3813	Approved
0.7257	Intermediate Similarity	NPD5862	Discovery
0.7256	Intermediate Similarity	NPD4805	Approved
0.7246	Intermediate Similarity	NPD4702	Approved
0.7246	Intermediate Similarity	NPD4703	Approved
0.7235	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2809	Approved
0.7225	Intermediate Similarity	NPD8026	Phase 1
0.7212	Intermediate Similarity	NPD3717	Discontinued
0.7209	Intermediate Similarity	NPD5255	Approved
0.7197	Intermediate Similarity	NPD9284	Approved
0.7195	Intermediate Similarity	NPD1649	Discontinued
0.7193	Intermediate Similarity	NPD6026	Approved
0.717	Intermediate Similarity	NPD9207	Approved
0.717	Intermediate Similarity	NPD9206	Approved
0.7168	Intermediate Similarity	NPD2511	Approved
0.7152	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2582	Approved
0.7151	Intermediate Similarity	NPD2581	Approved
0.7134	Intermediate Similarity	NPD4804	Approved
0.7128	Intermediate Similarity	NPD4427	Phase 2
0.7111	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7913	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5088	Discontinued
0.6989	Remote Similarity	NPD6635	Approved
0.6981	Remote Similarity	NPD9080	Approved
0.6973	Remote Similarity	NPD3082	Discontinued
0.697	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7469	Discontinued
0.6878	Remote Similarity	NPD4699	Discontinued
0.6875	Remote Similarity	NPD2118	Approved
0.6875	Remote Similarity	NPD2119	Approved
0.6872	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD4021	Phase 2
0.6857	Remote Similarity	NPD9382	Approved
0.6857	Remote Similarity	NPD9383	Approved
0.6851	Remote Similarity	NPD2076	Approved
0.6851	Remote Similarity	NPD2077	Approved
0.6847	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8325	Phase 3
0.6847	Remote Similarity	NPD8326	Phase 3
0.6842	Remote Similarity	NPD1661	Suspended
0.6821	Remote Similarity	NPD3262	Approved
0.6815	Remote Similarity	NPD271	Approved
0.6815	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD268	Approved
0.6813	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4529	Approved
0.6806	Remote Similarity	NPD4528	Approved
0.6806	Remote Similarity	NPD4526	Approved
0.6802	Remote Similarity	NPD3576	Approved
0.6802	Remote Similarity	NPD7396	Approved
0.6802	Remote Similarity	NPD3575	Approved
0.6791	Remote Similarity	NPD6227	Discontinued
0.6786	Remote Similarity	NPD5486	Discontinued
0.678	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.678	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4824	Approved
0.6776	Remote Similarity	NPD4823	Approved
0.6748	Remote Similarity	NPD3476	Approved
0.6748	Remote Similarity	NPD3475	Approved
0.6739	Remote Similarity	NPD1032	Phase 2
0.6727	Remote Similarity	NPD3944	Approved
0.6727	Remote Similarity	NPD3942	Approved
0.6717	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8321	Discontinued
0.6707	Remote Similarity	NPD9726	Discontinued
0.6704	Remote Similarity	NPD8129	Discovery
0.6685	Remote Similarity	NPD4639	Approved
0.6685	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4638	Approved
0.6685	Remote Similarity	NPD4640	Approved
0.6685	Remote Similarity	NPD5100	Phase 3
0.6684	Remote Similarity	NPD7233	Approved
0.6684	Remote Similarity	NPD7944	Discontinued
0.6684	Remote Similarity	NPD7234	Approved
0.6683	Remote Similarity	NPD5458	Discontinued
0.6667	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6569	Phase 2
0.6667	Remote Similarity	NPD820	Phase 3
0.6667	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4375	Approved
0.6667	Remote Similarity	NPD1994	Approved
0.6667	Remote Similarity	NPD1995	Approved
0.6667	Remote Similarity	NPD6529	Discontinued
0.6667	Remote Similarity	NPD1993	Approved
0.6649	Remote Similarity	NPD4072	Approved
0.6649	Remote Similarity	NPD4071	Approved
0.6649	Remote Similarity	NPD3321	Discontinued
0.6647	Remote Similarity	NPD792	Discontinued
0.6647	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4086	Phase 1
0.6635	Remote Similarity	NPD6298	Discontinued
0.6633	Remote Similarity	NPD31	Approved
0.6633	Remote Similarity	NPD4122	Approved
0.6633	Remote Similarity	NPD4037	Approved
0.6633	Remote Similarity	NPD4039	Approved
0.6633	Remote Similarity	NPD4034	Approved
0.6633	Remote Similarity	NPD4036	Approved
0.6633	Remote Similarity	NPD4033	Approved
0.6633	Remote Similarity	NPD4038	Approved
0.6633	Remote Similarity	NPD32	Approved
0.6633	Remote Similarity	NPD4035	Approved
0.6632	Remote Similarity	NPD4551	Phase 2
0.6627	Remote Similarity	NPD4030	Approved
0.6627	Remote Similarity	NPD4029	Approved
0.6627	Remote Similarity	NPD4028	Approved
0.6618	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6626	Approved
0.6614	Remote Similarity	NPD6241	Phase 1
0.6613	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6555	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD2123	Phase 3
0.6612	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD3525	Discontinued
0.6605	Remote Similarity	NPD9583	Approved
0.66	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6068	Discontinued
0.6596	Remote Similarity	NPD5596	Phase 2
0.6593	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD9357	Approved
0.6579	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6595	Phase 3
0.6567	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD1598	Discontinued
0.6564	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD991	Phase 2
0.6561	Remote Similarity	NPD1096	Discontinued
0.6557	Remote Similarity	NPD2619	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD2620	Phase 2
0.6554	Remote Similarity	NPD2061	Approved
0.6545	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1034	Phase 3
0.6545	Remote Similarity	NPD715	Phase 3
0.6543	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3386	Phase 2
0.6543	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2928	Phase 2
0.6538	Remote Similarity	NPD5611	Phase 2
0.6534	Remote Similarity	NPD510	Phase 1
0.6534	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1622	Discontinued
0.6531	Remote Similarity	NPD1229	Phase 2
0.6531	Remote Similarity	NPD2952	Discontinued
0.6526	Remote Similarity	NPD5555	Phase 1
0.6522	Remote Similarity	NPD3116	Approved
0.6522	Remote Similarity	NPD3117	Approved
0.6519	Remote Similarity	NPD5925	Phase 1
0.6515	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6363	Clinical (unspecified phase)
0.651	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD201	Phase 2
0.6509	Remote Similarity	NPD200	Phase 2
0.6495	Remote Similarity	NPD6665	Discontinued
0.6488	Remote Similarity	NPD2141	Approved
0.6488	Remote Similarity	NPD2142	Approved
0.6488	Remote Similarity	NPD2140	Approved
0.6485	Remote Similarity	NPD1392	Approved
0.6484	Remote Similarity	NPD925	Approved
0.6484	Remote Similarity	NPD926	Approved
0.6481	Remote Similarity	NPD7558	Phase 2
0.648	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD8169	Discontinued
0.6467	Remote Similarity	NPD4973	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