NPASS Compound

Structure

NPC278366 OpenBabel07101719252D 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 2.5000 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 3.0000 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 3 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 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 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:	2.423
LogD:	2.782
LogS:	-3.021
# 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:	4.216
Fsp3:	0.731
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.086
MDCK Permeability:	3.6218891182215884e-05
Pgp-inhibitor:	0.907
Pgp-substrate:	0.394
Human Intestinal Absorption (HIA):	0.735
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	90.65489959716797%
Volume Distribution (VD):	0.544
Pgp-substrate:	3.096013069152832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.259
CYP1A2-substrate:	0.513
CYP2C19-inhibitor:	0.567
CYP2C19-substrate:	0.297
CYP2C9-inhibitor:	0.634
CYP2C9-substrate:	0.853
CYP2D6-inhibitor:	0.591
CYP2D6-substrate:	0.196
CYP3A4-inhibitor:	0.877
CYP3A4-substrate:	0.118

ADMET: Excretion

Clearance (CL):	6.916
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.398
Human Hepatotoxicity (H-HT):	0.149
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.945
Carcinogencity:	0.06
Eye Corrosion:	0.008
Eye Irritation:	0.104
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC278366

Natural Product ID:	NPC278366
*Common Name:**	Amphimedoside B
IUPAC Name:	(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[methoxy(14-pyridin-3-yltetradec-9-ynyl)amino]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	VHFWMJKIAPMPHF-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,2-3,5,7-13,15,18,20H2,1H3/t22-,23-,24+,25-,26-/m1/s1
SMILES:	CON(CCCCCCCCC#CCCCCc1cccnc1)[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463397
PubChem CID:	16091666
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	=	11.0	ug.mL-1	PMID[505165]

☑ 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 NPC278366 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	247
0.1-0.2	1278
0.2-0.3	10272
0.3-0.4	21152
0.4-0.5	5995
0.5-0.6	2745
0.6-0.7	945
0.7-0.8	58
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
1.0	High Similarity	NPC127730
0.9934	High Similarity	NPC85918
0.9801	High Similarity	NPC71079
0.9737	High Similarity	NPC474217
0.8103	Intermediate Similarity	NPC62510
0.8049	Intermediate Similarity	NPC138018
0.7881	Intermediate Similarity	NPC169625
0.7881	Intermediate Similarity	NPC202957
0.7719	Intermediate Similarity	NPC319456
0.7712	Intermediate Similarity	NPC471311
0.7712	Intermediate Similarity	NPC471313
0.7682	Intermediate Similarity	NPC290094
0.7622	Intermediate Similarity	NPC149708
0.7548	Intermediate Similarity	NPC89490
0.7546	Intermediate Similarity	NPC471323
0.7514	Intermediate Similarity	NPC328798
0.75	Intermediate Similarity	NPC475105
0.75	Intermediate Similarity	NPC475090
0.75	Intermediate Similarity	NPC329896
0.7486	Intermediate Similarity	NPC325093
0.7442	Intermediate Similarity	NPC476446
0.7442	Intermediate Similarity	NPC78375
0.7442	Intermediate Similarity	NPC469813
0.7418	Intermediate Similarity	NPC325775
0.7403	Intermediate Similarity	NPC318020
0.7389	Intermediate Similarity	NPC327373
0.7389	Intermediate Similarity	NPC322043
0.7377	Intermediate Similarity	NPC182814
0.7366	Intermediate Similarity	NPC20593
0.7299	Intermediate Similarity	NPC477975
0.7297	Intermediate Similarity	NPC127647
0.7296	Intermediate Similarity	NPC324611
0.7284	Intermediate Similarity	NPC471312
0.7278	Intermediate Similarity	NPC317010
0.7211	Intermediate Similarity	NPC50997
0.7211	Intermediate Similarity	NPC160127
0.7188	Intermediate Similarity	NPC256893
0.7152	Intermediate Similarity	NPC165370
0.7152	Intermediate Similarity	NPC212125
0.7143	Intermediate Similarity	NPC472752
0.7143	Intermediate Similarity	NPC40779
0.7127	Intermediate Similarity	NPC133261
0.7125	Intermediate Similarity	NPC315320
0.712	Intermediate Similarity	NPC474767
0.7111	Intermediate Similarity	NPC203754
0.7111	Intermediate Similarity	NPC150048
0.7111	Intermediate Similarity	NPC472122
0.7111	Intermediate Similarity	NPC24594
0.7102	Intermediate Similarity	NPC471178
0.7077	Intermediate Similarity	NPC309498
0.707	Intermediate Similarity	NPC476322
0.7062	Intermediate Similarity	NPC108469
0.7059	Intermediate Similarity	NPC297486
0.7059	Intermediate Similarity	NPC240136
0.7059	Intermediate Similarity	NPC471402
0.7045	Intermediate Similarity	NPC311276
0.7035	Intermediate Similarity	NPC292517
0.7033	Intermediate Similarity	NPC141377
0.7021	Intermediate Similarity	NPC473763
0.7021	Intermediate Similarity	NPC117244
0.7012	Intermediate Similarity	NPC29702
0.7011	Intermediate Similarity	NPC129721
0.6995	Remote Similarity	NPC187827
0.6995	Remote Similarity	NPC79223
0.6995	Remote Similarity	NPC472105
0.6979	Remote Similarity	NPC59033
0.6979	Remote Similarity	NPC470499
0.6978	Remote Similarity	NPC326575
0.6975	Remote Similarity	NPC471322
0.6963	Remote Similarity	NPC292361
0.6959	Remote Similarity	NPC32451
0.6959	Remote Similarity	NPC328559
0.6957	Remote Similarity	NPC470474
0.695	Remote Similarity	NPC476467
0.6949	Remote Similarity	NPC473057
0.6947	Remote Similarity	NPC289786
0.6944	Remote Similarity	NPC470498
0.6943	Remote Similarity	NPC329825
0.6939	Remote Similarity	NPC12944
0.6939	Remote Similarity	NPC25442
0.6937	Remote Similarity	NPC306397
0.6931	Remote Similarity	NPC30570
0.6927	Remote Similarity	NPC329024
0.6923	Remote Similarity	NPC476874
0.6919	Remote Similarity	NPC472110
0.6919	Remote Similarity	NPC472109
0.6919	Remote Similarity	NPC63041
0.6914	Remote Similarity	NPC69914
0.6914	Remote Similarity	NPC469762
0.6907	Remote Similarity	NPC470497
0.6906	Remote Similarity	NPC314603
0.6903	Remote Similarity	NPC91958
0.6897	Remote Similarity	NPC162812
0.6893	Remote Similarity	NPC471177
0.6893	Remote Similarity	NPC124542
0.6893	Remote Similarity	NPC59779
0.6891	Remote Similarity	NPC317672
0.6891	Remote Similarity	NPC320748
0.6891	Remote Similarity	NPC324245
0.6884	Remote Similarity	NPC48042
0.6884	Remote Similarity	NPC472550
0.6884	Remote Similarity	NPC304179
0.6881	Remote Similarity	NPC313640
0.6879	Remote Similarity	NPC153769
0.6872	Remote Similarity	NPC98187
0.6872	Remote Similarity	NPC54988
0.6872	Remote Similarity	NPC160105
0.6869	Remote Similarity	NPC156044
0.6866	Remote Similarity	NPC472553
0.6857	Remote Similarity	NPC469785
0.6852	Remote Similarity	NPC476131
0.6851	Remote Similarity	NPC89562
0.6847	Remote Similarity	NPC477910
0.6845	Remote Similarity	NPC188387
0.6845	Remote Similarity	NPC163421
0.6829	Remote Similarity	NPC472555
0.6829	Remote Similarity	NPC322488
0.6828	Remote Similarity	NPC139291
0.6828	Remote Similarity	NPC469358
0.6828	Remote Similarity	NPC472108
0.6821	Remote Similarity	NPC27802
0.6818	Remote Similarity	NPC132680
0.6818	Remote Similarity	NPC269919
0.6814	Remote Similarity	NPC475408
0.6814	Remote Similarity	NPC206343
0.6814	Remote Similarity	NPC477908
0.6814	Remote Similarity	NPC471014
0.6813	Remote Similarity	NPC166424
0.6813	Remote Similarity	NPC146373
0.6813	Remote Similarity	NPC245244
0.6802	Remote Similarity	NPC477974
0.68	Remote Similarity	NPC63562
0.6791	Remote Similarity	NPC207851
0.6782	Remote Similarity	NPC111732
0.678	Remote Similarity	NPC314270
0.678	Remote Similarity	NPC144779
0.678	Remote Similarity	NPC294579
0.6778	Remote Similarity	NPC49954
0.6778	Remote Similarity	NPC474561
0.6772	Remote Similarity	NPC265605
0.6772	Remote Similarity	NPC182570
0.6772	Remote Similarity	NPC48564
0.6765	Remote Similarity	NPC470306
0.6762	Remote Similarity	NPC476492
0.676	Remote Similarity	NPC263439
0.676	Remote Similarity	NPC97367
0.6744	Remote Similarity	NPC161292
0.6743	Remote Similarity	NPC259644
0.6743	Remote Similarity	NPC469760
0.6743	Remote Similarity	NPC469786
0.6743	Remote Similarity	NPC469765
0.6743	Remote Similarity	NPC73952
0.6743	Remote Similarity	NPC469763
0.6743	Remote Similarity	NPC25008
0.6742	Remote Similarity	NPC63338
0.6742	Remote Similarity	NPC322976
0.6742	Remote Similarity	NPC324203
0.6738	Remote Similarity	NPC163055
0.6732	Remote Similarity	NPC6981
0.6732	Remote Similarity	NPC471016
0.6731	Remote Similarity	NPC477911
0.6728	Remote Similarity	NPC278451
0.6721	Remote Similarity	NPC477976
0.672	Remote Similarity	NPC471997
0.6716	Remote Similarity	NPC319128
0.6716	Remote Similarity	NPC228331
0.6705	Remote Similarity	NPC80597
0.6705	Remote Similarity	NPC211572
0.6705	Remote Similarity	NPC70922
0.6705	Remote Similarity	NPC212376
0.6705	Remote Similarity	NPC75540
0.6704	Remote Similarity	NPC282231
0.6702	Remote Similarity	NPC284559
0.6702	Remote Similarity	NPC95783
0.67	Remote Similarity	NPC475835
0.6699	Remote Similarity	NPC62367
0.6688	Remote Similarity	NPC143603
0.6685	Remote Similarity	NPC230869
0.6685	Remote Similarity	NPC469938
0.6684	Remote Similarity	NPC279401
0.6684	Remote Similarity	NPC79293
0.6684	Remote Similarity	NPC233936
0.6683	Remote Similarity	NPC42678
0.6683	Remote Similarity	NPC118832
0.6683	Remote Similarity	NPC329708
0.6683	Remote Similarity	NPC264166
0.6683	Remote Similarity	NPC274291
0.6683	Remote Similarity	NPC477907
0.6683	Remote Similarity	NPC165349
0.6683	Remote Similarity	NPC477909
0.6683	Remote Similarity	NPC47059
0.6682	Remote Similarity	NPC244536
0.6667	Remote Similarity	NPC216428
0.6667	Remote Similarity	NPC477902
0.6667	Remote Similarity	NPC158129
0.6667	Remote Similarity	NPC194640
0.6667	Remote Similarity	NPC193761
0.6667	Remote Similarity	NPC84815
0.6667	Remote Similarity	NPC301368
0.6667	Remote Similarity	NPC165837

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 NPC278366 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	490
0.2-0.3	837
0.3-0.4	1705
0.4-0.5	3546
0.5-0.6	1956
0.6-0.7	426
0.7-0.8	36
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
0.7785	Intermediate Similarity	NPD1380	Discovery
0.7722	Intermediate Similarity	NPD2544	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4239	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1383	Phase 3
0.764	Intermediate Similarity	NPD1382	Phase 2
0.7514	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8408	Discontinued
0.7418	Intermediate Similarity	NPD8021	Approved
0.7418	Intermediate Similarity	NPD8020	Approved
0.7391	Intermediate Similarity	NPD9506	Approved
0.736	Intermediate Similarity	NPD8123	Approved
0.736	Intermediate Similarity	NPD8122	Approved
0.7346	Intermediate Similarity	NPD2896	Discontinued
0.7337	Intermediate Similarity	NPD8063	Discontinued
0.7333	Intermediate Similarity	NPD3813	Approved
0.7314	Intermediate Similarity	NPD5862	Discovery
0.7305	Intermediate Similarity	NPD4703	Approved
0.7305	Intermediate Similarity	NPD4702	Approved
0.7294	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD2809	Approved
0.7273	Intermediate Similarity	NPD3717	Discontinued
0.7267	Intermediate Similarity	NPD5255	Approved
0.7251	Intermediate Similarity	NPD6026	Approved
0.7229	Intermediate Similarity	NPD1352	Discontinued
0.7225	Intermediate Similarity	NPD2511	Approved
0.7212	Intermediate Similarity	NPD4805	Approved
0.7209	Intermediate Similarity	NPD2581	Approved
0.7209	Intermediate Similarity	NPD2582	Approved
0.7184	Intermediate Similarity	NPD8026	Phase 1
0.7181	Intermediate Similarity	NPD4427	Phase 2
0.7167	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1649	Discontinued
0.7152	Intermediate Similarity	NPD9284	Approved
0.7135	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD9207	Approved
0.7125	Intermediate Similarity	NPD9206	Approved
0.7107	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4804	Approved
0.7062	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6635	Approved
0.7045	Intermediate Similarity	NPD5088	Discontinued
0.7041	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7913	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7469	Discontinued
0.6937	Remote Similarity	NPD2118	Approved
0.6937	Remote Similarity	NPD9080	Approved
0.6937	Remote Similarity	NPD2119	Approved
0.6935	Remote Similarity	NPD3082	Discontinued
0.6933	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2077	Approved
0.6906	Remote Similarity	NPD2076	Approved
0.6897	Remote Similarity	NPD8325	Phase 3
0.6897	Remote Similarity	NPD8326	Phase 3
0.6897	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3262	Approved
0.6859	Remote Similarity	NPD4528	Approved
0.6859	Remote Similarity	NPD4526	Approved
0.6859	Remote Similarity	NPD4529	Approved
0.6845	Remote Similarity	NPD6227	Discontinued
0.6845	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4699	Discontinued
0.6837	Remote Similarity	NPD5486	Discontinued
0.6825	Remote Similarity	NPD4021	Phase 2
0.6818	Remote Similarity	NPD9382	Approved
0.6818	Remote Similarity	NPD9383	Approved
0.681	Remote Similarity	NPD3476	Approved
0.681	Remote Similarity	NPD3475	Approved
0.6802	Remote Similarity	NPD1661	Suspended
0.6793	Remote Similarity	NPD1032	Phase 2
0.6788	Remote Similarity	NPD3942	Approved
0.6788	Remote Similarity	NPD3944	Approved
0.6776	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD271	Approved
0.6772	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD268	Approved
0.6768	Remote Similarity	NPD7396	Approved
0.6766	Remote Similarity	NPD8321	Discontinued
0.6763	Remote Similarity	NPD3576	Approved
0.6763	Remote Similarity	NPD3575	Approved
0.676	Remote Similarity	NPD8129	Discovery
0.6742	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.674	Remote Similarity	NPD4640	Approved
0.674	Remote Similarity	NPD4639	Approved
0.674	Remote Similarity	NPD4638	Approved
0.6739	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5100	Phase 3
0.6737	Remote Similarity	NPD7234	Approved
0.6737	Remote Similarity	NPD7233	Approved
0.6736	Remote Similarity	NPD7944	Discontinued
0.6734	Remote Similarity	NPD5458	Discontinued
0.6732	Remote Similarity	NPD4823	Approved
0.6732	Remote Similarity	NPD4824	Approved
0.673	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD1994	Approved
0.6727	Remote Similarity	NPD1995	Approved
0.6727	Remote Similarity	NPD1993	Approved
0.6723	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4375	Approved
0.6719	Remote Similarity	NPD6569	Phase 2
0.6716	Remote Similarity	NPD6529	Discontinued
0.6707	Remote Similarity	NPD792	Discontinued
0.6702	Remote Similarity	NPD3321	Discontinued
0.6687	Remote Similarity	NPD4028	Approved
0.6687	Remote Similarity	NPD4029	Approved
0.6687	Remote Similarity	NPD4030	Approved
0.6683	Remote Similarity	NPD4035	Approved
0.6683	Remote Similarity	NPD4037	Approved
0.6683	Remote Similarity	NPD4033	Approved
0.6683	Remote Similarity	NPD4039	Approved
0.6683	Remote Similarity	NPD4122	Approved
0.6683	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4034	Approved
0.6683	Remote Similarity	NPD32	Approved
0.6683	Remote Similarity	NPD6298	Discontinued
0.6683	Remote Similarity	NPD31	Approved
0.6683	Remote Similarity	NPD4038	Approved
0.6683	Remote Similarity	NPD4036	Approved
0.6682	Remote Similarity	NPD4086	Phase 1
0.6667	Remote Similarity	NPD9583	Approved
0.6667	Remote Similarity	NPD6241	Phase 1
0.6667	Remote Similarity	NPD9726	Discontinued
0.6667	Remote Similarity	NPD3525	Discontinued
0.6667	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6555	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6626	Approved
0.6667	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6068	Discontinued
0.6648	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD6595	Phase 3
0.6629	Remote Similarity	NPD820	Phase 3
0.6626	Remote Similarity	NPD991	Phase 2
0.6626	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD4072	Approved
0.6613	Remote Similarity	NPD4071	Approved
0.6609	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD715	Phase 3
0.6604	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4551	Phase 2
0.6597	Remote Similarity	NPD1034	Phase 3
0.6597	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3386	Phase 2
0.6596	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5611	Phase 2
0.6589	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1229	Phase 2
0.6579	Remote Similarity	NPD5555	Phase 1
0.6576	Remote Similarity	NPD2123	Phase 3
0.6566	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6363	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5596	Phase 2
0.6545	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD9357	Approved
0.6538	Remote Similarity	NPD925	Approved
0.6538	Remote Similarity	NPD926	Approved
0.6531	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7558	Phase 2
0.6526	Remote Similarity	NPD1096	Discontinued
0.6524	Remote Similarity	NPD1598	Discontinued
0.6522	Remote Similarity	NPD2619	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4973	Approved
0.6522	Remote Similarity	NPD2620	Phase 2
0.6517	Remote Similarity	NPD8169	Discontinued
0.6517	Remote Similarity	NPD2061	Approved
0.6515	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD1270	Approved
0.6513	Remote Similarity	NPD6361	Phase 2
0.651	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD2928	Phase 2
0.65	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2952	Discontinued
0.6497	Remote Similarity	NPD1622	Discontinued
0.6497	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD510	Phase 1
0.6491	Remote Similarity	NPD2072	Approved
0.6491	Remote Similarity	NPD2073	Approved
0.6491	Remote Similarity	NPD2070	Approved
0.6491	Remote Similarity	NPD2069	Approved
0.6491	Remote Similarity	NPD2074	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