NPASS Compound

Structure

NPC474217 OpenBabel07101718272D 33 34 0 0 1 0 0 0 0 0999 V2000 0.8660 3.5000 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 5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 0.0000 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 8.6603 0.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.7942 0.5000 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 8.6603 -1.0000 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 -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 19 1 0 0 0 0 2 32 1 0 0 0 0 3 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 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 20 1 0 0 0 0 15 26 2 0 0 0 0 16 20 2 0 0 0 0 16 26 1 0 0 0 0 17 19 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 21 18 1 1 0 0 0 21 22 1 0 0 0 0 21 33 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 6 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 27 1 1 0 0 0 25 33 1 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.32
Volume:	490.669
LogP:	3.301
LogD:	3.267
LogS:	-3.272
# Rotatable Bonds:	16
TPSA:	115.51
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.216
Synthetic Accessibility Score:	4.166
Fsp3:	0.8
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:	-5.174
MDCK Permeability:	3.731002288986929e-05
Pgp-inhibitor:	0.741
Pgp-substrate:	0.183
Human Intestinal Absorption (HIA):	0.143
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.578

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.19
Plasma Protein Binding (PPB):	88.9131088256836%
Volume Distribution (VD):	1.317
Pgp-substrate:	4.748123645782471%

ADMET: Metabolism

CYP1A2-inhibitor:	0.077
CYP1A2-substrate:	0.402
CYP2C19-inhibitor:	0.101
CYP2C19-substrate:	0.18
CYP2C9-inhibitor:	0.075
CYP2C9-substrate:	0.76
CYP2D6-inhibitor:	0.317
CYP2D6-substrate:	0.2
CYP3A4-inhibitor:	0.652
CYP3A4-substrate:	0.124

ADMET: Excretion

Clearance (CL):	7.496
Half-life (T1/2):	0.755

ADMET: Toxicity

hERG Blockers:	0.357
Human Hepatotoxicity (H-HT):	0.257
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.157
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.929
Carcinogencity:	0.043
Eye Corrosion:	0.009
Eye Irritation:	0.136
Respiratory Toxicity:	0.821

Download Data

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

Natural Product: NPC474217

Natural Product ID:	NPC474217
*Common Name:**	Amphimedoside D
IUPAC Name:	(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[methoxy-(2-methyl-12-pyridin-3-yldodecyl)amino]oxane-3,4,5-triol
Synonyms:	Amphimedoside D
Standard InCHIKey:	QTNAFZASVRWZNR-UXBITIETSA-N
Standard InCHI:	InChI=1S/C25H44N2O6/c1-19(17-27(32-2)25-24(31)23(30)22(29)21(18-28)33-25)12-9-7-5-3-4-6-8-10-13-20-14-11-15-26-16-20/h11,14-16,19,21-25,28-31H,3-10,12-13,17-18H2,1-2H3/t19?,21-,22-,23+,24-,25-/m1/s1
SMILES:	CC(CCCCCCCCCCC1=CN=CC=C1)CN(C2C(C(C(C(O2)CO)O)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463596
PubChem CID:	16091667
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	=	0.45	ug.mL-1	PMID[455649]

☑ 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 NPC474217 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	1208
0.2-0.3	8493
0.3-0.4	22048
0.4-0.5	6620
0.5-0.6	2910
0.6-0.7	1073
0.7-0.8	97
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	NPC71079
0.9737	High Similarity	NPC127730
0.9737	High Similarity	NPC278366
0.9671	High Similarity	NPC85918
0.8198	Intermediate Similarity	NPC62510
0.8148	Intermediate Similarity	NPC138018
0.7815	Intermediate Similarity	NPC471311
0.7815	Intermediate Similarity	NPC471313
0.7811	Intermediate Similarity	NPC319456
0.7785	Intermediate Similarity	NPC290094
0.7712	Intermediate Similarity	NPC329896
0.7712	Intermediate Similarity	NPC475105
0.7712	Intermediate Similarity	NPC475090
0.7705	Intermediate Similarity	NPC149708
0.7697	Intermediate Similarity	NPC328798
0.767	Intermediate Similarity	NPC325093
0.7647	Intermediate Similarity	NPC89490
0.764	Intermediate Similarity	NPC471323
0.7632	Intermediate Similarity	NPC202957
0.7632	Intermediate Similarity	NPC169625
0.7598	Intermediate Similarity	NPC325775
0.7584	Intermediate Similarity	NPC318020
0.7571	Intermediate Similarity	NPC327373
0.7571	Intermediate Similarity	NPC322043
0.7556	Intermediate Similarity	NPC182814
0.7541	Intermediate Similarity	NPC20593
0.7529	Intermediate Similarity	NPC78375
0.7529	Intermediate Similarity	NPC476446
0.7529	Intermediate Similarity	NPC469813
0.7485	Intermediate Similarity	NPC477975
0.7473	Intermediate Similarity	NPC127647
0.7389	Intermediate Similarity	NPC324611
0.738	Intermediate Similarity	NPC160127
0.738	Intermediate Similarity	NPC50997
0.7375	Intermediate Similarity	NPC471312
0.736	Intermediate Similarity	NPC317010
0.7306	Intermediate Similarity	NPC472752
0.7288	Intermediate Similarity	NPC203754
0.7288	Intermediate Similarity	NPC24594
0.7288	Intermediate Similarity	NPC472122
0.7288	Intermediate Similarity	NPC150048
0.7278	Intermediate Similarity	NPC256893
0.7244	Intermediate Similarity	NPC212125
0.7244	Intermediate Similarity	NPC165370
0.7241	Intermediate Similarity	NPC108469
0.7225	Intermediate Similarity	NPC40779
0.7215	Intermediate Similarity	NPC315320
0.7207	Intermediate Similarity	NPC141377
0.7207	Intermediate Similarity	NPC133261
0.7196	Intermediate Similarity	NPC474767
0.7194	Intermediate Similarity	NPC292517
0.7189	Intermediate Similarity	NPC473763
0.7189	Intermediate Similarity	NPC117244
0.7184	Intermediate Similarity	NPC471178
0.7167	Intermediate Similarity	NPC187827
0.7167	Intermediate Similarity	NPC472105
0.7161	Intermediate Similarity	NPC476322
0.7158	Intermediate Similarity	NPC79223
0.7152	Intermediate Similarity	NPC471402
0.7152	Intermediate Similarity	NPC240136
0.7152	Intermediate Similarity	NPC297486
0.7151	Intermediate Similarity	NPC326575
0.715	Intermediate Similarity	NPC309498
0.7143	Intermediate Similarity	NPC329825
0.7143	Intermediate Similarity	NPC59033
0.7127	Intermediate Similarity	NPC470474
0.7126	Intermediate Similarity	NPC473057
0.7126	Intermediate Similarity	NPC311276
0.712	Intermediate Similarity	NPC32451
0.712	Intermediate Similarity	NPC328559
0.7112	Intermediate Similarity	NPC289786
0.7107	Intermediate Similarity	NPC476467
0.7099	Intermediate Similarity	NPC29702
0.7098	Intermediate Similarity	NPC12944
0.7098	Intermediate Similarity	NPC25442
0.7093	Intermediate Similarity	NPC129721
0.709	Intermediate Similarity	NPC329024
0.7088	Intermediate Similarity	NPC472110
0.7088	Intermediate Similarity	NPC472109
0.7085	Intermediate Similarity	NPC30570
0.7079	Intermediate Similarity	NPC314603
0.7077	Intermediate Similarity	NPC63041
0.7063	Intermediate Similarity	NPC471322
0.7053	Intermediate Similarity	NPC324245
0.7053	Intermediate Similarity	NPC317672
0.7053	Intermediate Similarity	NPC470499
0.7053	Intermediate Similarity	NPC320748
0.705	Intermediate Similarity	NPC162812
0.7045	Intermediate Similarity	NPC160105
0.7045	Intermediate Similarity	NPC98187
0.7041	Intermediate Similarity	NPC48042
0.7041	Intermediate Similarity	NPC304179
0.7041	Intermediate Similarity	NPC472550
0.7037	Intermediate Similarity	NPC292361
0.7035	Intermediate Similarity	NPC313640
0.7026	Intermediate Similarity	NPC156044
0.7025	Intermediate Similarity	NPC306397
0.7022	Intermediate Similarity	NPC470498
0.702	Intermediate Similarity	NPC472553
0.7011	Intermediate Similarity	NPC163421
0.7011	Intermediate Similarity	NPC188387
0.7	Intermediate Similarity	NPC69914
0.7	Intermediate Similarity	NPC477910
0.6995	Remote Similarity	NPC476874
0.6995	Remote Similarity	NPC139291
0.6995	Remote Similarity	NPC472108
0.6994	Remote Similarity	NPC469762
0.6993	Remote Similarity	NPC91958
0.6982	Remote Similarity	NPC477974
0.698	Remote Similarity	NPC472555
0.6979	Remote Similarity	NPC470497
0.6971	Remote Similarity	NPC124542
0.6971	Remote Similarity	NPC471177
0.6971	Remote Similarity	NPC59779
0.6965	Remote Similarity	NPC471014
0.6965	Remote Similarity	NPC206343
0.6965	Remote Similarity	NPC477908
0.6965	Remote Similarity	NPC475408
0.6959	Remote Similarity	NPC153769
0.6949	Remote Similarity	NPC474561
0.6949	Remote Similarity	NPC49954
0.6949	Remote Similarity	NPC54988
0.6937	Remote Similarity	NPC476131
0.6936	Remote Similarity	NPC469785
0.6935	Remote Similarity	NPC111732
0.6931	Remote Similarity	NPC314270
0.6931	Remote Similarity	NPC144779
0.6931	Remote Similarity	NPC294579
0.6927	Remote Similarity	NPC89562
0.6918	Remote Similarity	NPC278451
0.6915	Remote Similarity	NPC470306
0.6914	Remote Similarity	NPC322488
0.6913	Remote Similarity	NPC27802
0.6908	Remote Similarity	NPC476492
0.6902	Remote Similarity	NPC469358
0.6899	Remote Similarity	NPC166424
0.6899	Remote Similarity	NPC245244
0.6899	Remote Similarity	NPC146373
0.6897	Remote Similarity	NPC269919
0.6897	Remote Similarity	NPC132680
0.6889	Remote Similarity	NPC477976
0.6885	Remote Similarity	NPC471997
0.6881	Remote Similarity	NPC471016
0.6881	Remote Similarity	NPC6981
0.6879	Remote Similarity	NPC63562
0.6878	Remote Similarity	NPC477911
0.6866	Remote Similarity	NPC228331
0.6866	Remote Similarity	NPC319128
0.6865	Remote Similarity	NPC207851
0.6862	Remote Similarity	NPC95783
0.6859	Remote Similarity	NPC182570
0.6859	Remote Similarity	NPC48564
0.6859	Remote Similarity	NPC265605
0.6853	Remote Similarity	NPC475835
0.6851	Remote Similarity	NPC469938
0.6848	Remote Similarity	NPC233936
0.6847	Remote Similarity	NPC62367
0.6837	Remote Similarity	NPC329708
0.6837	Remote Similarity	NPC264166
0.6837	Remote Similarity	NPC274291
0.6837	Remote Similarity	NPC165349
0.6837	Remote Similarity	NPC47059
0.6837	Remote Similarity	NPC118832
0.6836	Remote Similarity	NPC263439
0.6836	Remote Similarity	NPC97367
0.6832	Remote Similarity	NPC477909
0.6832	Remote Similarity	NPC42678
0.6832	Remote Similarity	NPC477907
0.6827	Remote Similarity	NPC244536
0.6824	Remote Similarity	NPC161292
0.6821	Remote Similarity	NPC259644
0.6821	Remote Similarity	NPC73952
0.6821	Remote Similarity	NPC469765
0.6821	Remote Similarity	NPC25008
0.6821	Remote Similarity	NPC469760
0.6821	Remote Similarity	NPC469763
0.6821	Remote Similarity	NPC469786
0.6818	Remote Similarity	NPC322976
0.6818	Remote Similarity	NPC324203
0.6818	Remote Similarity	NPC63338
0.6816	Remote Similarity	NPC201700
0.6816	Remote Similarity	NPC165837
0.6814	Remote Similarity	NPC84815
0.6814	Remote Similarity	NPC216428
0.6814	Remote Similarity	NPC301368
0.6812	Remote Similarity	NPC475137
0.6812	Remote Similarity	NPC475498
0.6812	Remote Similarity	NPC477902
0.6811	Remote Similarity	NPC163055
0.6811	Remote Similarity	NPC472104
0.6791	Remote Similarity	NPC474707
0.6784	Remote Similarity	NPC470111
0.6782	Remote Similarity	NPC211572
0.6782	Remote Similarity	NPC80597
0.6782	Remote Similarity	NPC75540
0.6782	Remote Similarity	NPC212376
0.6782	Remote Similarity	NPC70922
0.678	Remote Similarity	NPC282231
0.6779	Remote Similarity	NPC473506
0.6774	Remote Similarity	NPC143603

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 NPC474217 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	471
0.2-0.3	764
0.3-0.4	1638
0.4-0.5	3488
0.5-0.6	2102
0.6-0.7	492
0.7-0.8	45
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
0.7892	Intermediate Similarity	NPD4239	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1380	Discovery
0.7809	Intermediate Similarity	NPD2544	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1382	Phase 2
0.7736	Intermediate Similarity	NPD1383	Phase 3
0.7614	Intermediate Similarity	NPD8408	Discontinued
0.76	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD8020	Approved
0.7598	Intermediate Similarity	NPD8021	Approved
0.7514	Intermediate Similarity	NPD8063	Discontinued
0.7485	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD9506	Approved
0.7469	Intermediate Similarity	NPD3717	Discontinued
0.7443	Intermediate Similarity	NPD8122	Approved
0.7443	Intermediate Similarity	NPD8123	Approved
0.744	Intermediate Similarity	NPD6026	Approved
0.7438	Intermediate Similarity	NPD2896	Discontinued
0.7423	Intermediate Similarity	NPD3813	Approved
0.7412	Intermediate Similarity	NPD2511	Approved
0.7399	Intermediate Similarity	NPD5862	Discovery
0.7394	Intermediate Similarity	NPD4703	Approved
0.7394	Intermediate Similarity	NPD4702	Approved
0.7381	Intermediate Similarity	NPD2809	Approved
0.7353	Intermediate Similarity	NPD5255	Approved
0.7351	Intermediate Similarity	NPD4427	Phase 2
0.7317	Intermediate Similarity	NPD1352	Discontinued
0.7301	Intermediate Similarity	NPD4805	Approved
0.7294	Intermediate Similarity	NPD2581	Approved
0.7294	Intermediate Similarity	NPD2582	Approved
0.7267	Intermediate Similarity	NPD8026	Phase 1
0.7247	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD9284	Approved
0.7239	Intermediate Similarity	NPD1649	Discontinued
0.7225	Intermediate Similarity	NPD6635	Approved
0.7219	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD9207	Approved
0.7215	Intermediate Similarity	NPD9206	Approved
0.7197	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4804	Approved
0.7159	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2118	Approved
0.7134	Intermediate Similarity	NPD2119	Approved
0.7126	Intermediate Similarity	NPD5088	Discontinued
0.7126	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7913	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD8326	Phase 3
0.705	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD8325	Phase 3
0.7025	Intermediate Similarity	NPD9080	Approved
0.7024	Intermediate Similarity	NPD7469	Discontinued
0.7019	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3082	Discontinued
0.7006	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4021	Phase 2
0.6983	Remote Similarity	NPD2077	Approved
0.6983	Remote Similarity	NPD2076	Approved
0.6981	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1032	Phase 2
0.6959	Remote Similarity	NPD3262	Approved
0.6944	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3576	Approved
0.6941	Remote Similarity	NPD3575	Approved
0.6931	Remote Similarity	NPD4529	Approved
0.6931	Remote Similarity	NPD4528	Approved
0.6931	Remote Similarity	NPD4526	Approved
0.6928	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8321	Discontinued
0.6919	Remote Similarity	NPD6227	Discontinued
0.6915	Remote Similarity	NPD4699	Discontinued
0.691	Remote Similarity	NPD4640	Approved
0.691	Remote Similarity	NPD4638	Approved
0.691	Remote Similarity	NPD4639	Approved
0.6907	Remote Similarity	NPD5486	Discontinued
0.6906	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7234	Approved
0.6898	Remote Similarity	NPD7233	Approved
0.6897	Remote Similarity	NPD9382	Approved
0.6897	Remote Similarity	NPD9383	Approved
0.6897	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3475	Approved
0.6894	Remote Similarity	NPD3476	Approved
0.6882	Remote Similarity	NPD1661	Suspended
0.6871	Remote Similarity	NPD3942	Approved
0.6871	Remote Similarity	NPD4028	Approved
0.6871	Remote Similarity	NPD3944	Approved
0.6871	Remote Similarity	NPD4029	Approved
0.6871	Remote Similarity	NPD4030	Approved
0.6869	Remote Similarity	NPD6529	Discontinued
0.6859	Remote Similarity	NPD268	Approved
0.6859	Remote Similarity	NPD271	Approved
0.6859	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4036	Approved
0.6837	Remote Similarity	NPD4034	Approved
0.6837	Remote Similarity	NPD4122	Approved
0.6837	Remote Similarity	NPD4038	Approved
0.6837	Remote Similarity	NPD32	Approved
0.6837	Remote Similarity	NPD4033	Approved
0.6837	Remote Similarity	NPD4035	Approved
0.6837	Remote Similarity	NPD7396	Approved
0.6837	Remote Similarity	NPD4037	Approved
0.6837	Remote Similarity	NPD4039	Approved
0.6837	Remote Similarity	NPD31	Approved
0.6836	Remote Similarity	NPD8129	Discovery
0.6829	Remote Similarity	NPD6298	Discontinued
0.6828	Remote Similarity	NPD6241	Phase 1
0.6827	Remote Similarity	NPD4086	Phase 1
0.6821	Remote Similarity	NPD4824	Approved
0.6821	Remote Similarity	NPD4823	Approved
0.6818	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5100	Phase 3
0.681	Remote Similarity	NPD1993	Approved
0.681	Remote Similarity	NPD1994	Approved
0.681	Remote Similarity	NPD1995	Approved
0.6809	Remote Similarity	NPD6068	Discontinued
0.6806	Remote Similarity	NPD7944	Discontinued
0.6802	Remote Similarity	NPD5458	Discontinued
0.6791	Remote Similarity	NPD4375	Approved
0.6789	Remote Similarity	NPD6569	Phase 2
0.6788	Remote Similarity	NPD792	Discontinued
0.6772	Remote Similarity	NPD3321	Discontinued
0.6768	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.675	Remote Similarity	NPD9583	Approved
0.6748	Remote Similarity	NPD9726	Discontinued
0.6746	Remote Similarity	NPD3525	Discontinued
0.6746	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6626	Approved
0.6732	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.673	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6363	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD991	Phase 2
0.6708	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD820	Phase 3
0.6703	Remote Similarity	NPD6595	Phase 3
0.6702	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD715	Phase 3
0.6686	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2620	Phase 2
0.6685	Remote Similarity	NPD2619	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4071	Approved
0.6685	Remote Similarity	NPD4072	Approved
0.6684	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2072	Approved
0.6667	Remote Similarity	NPD5611	Phase 2
0.6667	Remote Similarity	NPD2074	Approved
0.6667	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3386	Phase 2
0.6667	Remote Similarity	NPD2073	Approved
0.6667	Remote Similarity	NPD1034	Phase 3
0.6667	Remote Similarity	NPD2075	Approved
0.6667	Remote Similarity	NPD4551	Phase 2
0.6667	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2069	Approved
0.6667	Remote Similarity	NPD2068	Approved
0.6667	Remote Similarity	NPD8169	Discontinued
0.6667	Remote Similarity	NPD2071	Approved
0.6667	Remote Similarity	NPD6361	Phase 2
0.6667	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2070	Approved
0.6649	Remote Similarity	NPD4079	Approved
0.6649	Remote Similarity	NPD4076	Approved
0.6649	Remote Similarity	NPD5555	Phase 1
0.6649	Remote Similarity	NPD1229	Phase 2
0.6648	Remote Similarity	NPD2123	Phase 3
0.6633	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD5596	Phase 2
0.6625	Remote Similarity	NPD9357	Approved
0.6615	Remote Similarity	NPD6665	Discontinued
0.6611	Remote Similarity	NPD925	Approved
0.6611	Remote Similarity	NPD926	Approved
0.6605	Remote Similarity	NPD1598	Discontinued
0.6598	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3477	Phase 2
0.6596	Remote Similarity	NPD1096	Discontinued
0.6595	Remote Similarity	NPD6642	Approved
0.6595	Remote Similarity	NPD3505	Approved
0.6595	Remote Similarity	NPD6641	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