NPASS Compound

Structure

NPC470474 OpenBabel07101718192D 29 31 0 0 1 0 0 0 0 0999 V2000 -3.4641 0.0000 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 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 2.5981 -3.5000 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 1.7321 -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 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 1 7 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 19 2 0 0 0 0 14 25 1 0 0 0 0 15 2 1 6 0 0 0 16 3 1 6 0 0 0 16 21 1 0 0 0 0 17 4 1 6 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 19 23 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 15 1 1 0 0 0 21 29 1 0 0 0 0 22 20 1 1 0 0 0 22 29 1 0 0 0 0 23 27 1 0 0 0 0 24 25 2 0 0 0 0 24 28 1 0 0 0 0 25 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	399.24
Volume:	428.33
LogP:	5.772
LogD:	5.801
LogS:	-6.52
# Rotatable Bonds:	6
TPSA:	54.63
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.498
Synthetic Accessibility Score:	4.388
Fsp3:	0.542
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.623
MDCK Permeability:	2.1677253243979067e-05
Pgp-inhibitor:	0.128
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.468

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.668
Plasma Protein Binding (PPB):	96.70891571044922%
Volume Distribution (VD):	2.012
Pgp-substrate:	1.3973475694656372%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.166
CYP2C19-substrate:	0.946
CYP2C9-inhibitor:	0.141
CYP2C9-substrate:	0.143
CYP2D6-inhibitor:	0.13
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.353
CYP3A4-substrate:	0.823

ADMET: Excretion

Clearance (CL):	3.621
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.415
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.896
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.367
Carcinogencity:	0.064
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.046

Download Data

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

Natural Product: NPC470474

Natural Product ID:	NPC470474
*Common Name:**	3-[(2R,3R,5S,6R)-6-[(2R)-Butan-2-Yl]-3,5-Dimethyloxan-2-Yl]-2,4-Dimethoxy-1-Oxido-5-Phenylpyridin-1-Ium
IUPAC Name:	3-[(2R,3R,5S,6R)-6-[(2R)-butan-2-yl]-3,5-dimethyloxan-2-yl]-2,4-dimethoxy-1-oxido-5-phenylpyridin-1-ium
Synonyms:
Standard InCHIKey:	NLCQIWZNCQRSID-AMQPJZBWSA-N
Standard InCHI:	InChI=1S/C24H33NO4/c1-7-15(2)21-16(3)13-17(4)22(29-21)20-23(27-5)19(14-25(26)24(20)28-6)18-11-9-8-10-12-18/h8-12,14-17,21-22H,7,13H2,1-6H3/t15-,16+,17-,21-,22-/m1/s1
SMILES:	CCC(C)C1C(CC(C(O1)C2=C(C(=C[N+](=C2OC)[O-])C3=CC=CC=C3)OC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047185
PubChem CID:	70688332
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0002317] Phenylpyridines

*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
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20550123]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22530813]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	2
Others	2

Activity Type	# Activity
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6760.0	nM	PMID[505540]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6510.0	nM	PMID[505540]
NPT2	Others	Unspecified		Ratio IC50	>	1.1	n.a.	PMID[505540]
NPT2	Others	Unspecified		Ratio IC50	>	1.2	n.a.	PMID[505540]

☑ 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 NPC470474 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	460
0.1-0.2	1816
0.2-0.3	12282
0.3-0.4	5384
0.4-0.5	15919
0.5-0.6	5507
0.6-0.7	1182
0.7-0.8	135
0.8-0.85	4
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8556	High Similarity	NPC473053
0.8242	Intermediate Similarity	NPC289786
0.7796	Intermediate Similarity	NPC195268
0.7796	Intermediate Similarity	NPC133140
0.7759	Intermediate Similarity	NPC177404
0.7749	Intermediate Similarity	NPC31930
0.7714	Intermediate Similarity	NPC473057
0.7632	Intermediate Similarity	NPC224928
0.7629	Intermediate Similarity	NPC476581
0.7629	Intermediate Similarity	NPC16452
0.7629	Intermediate Similarity	NPC36229
0.7627	Intermediate Similarity	NPC108469
0.759	Intermediate Similarity	NPC470164
0.759	Intermediate Similarity	NPC323345
0.7582	Intermediate Similarity	NPC472168
0.7552	Intermediate Similarity	NPC476578
0.7552	Intermediate Similarity	NPC476582
0.7552	Intermediate Similarity	NPC4071
0.7527	Intermediate Similarity	NPC283152
0.7472	Intermediate Similarity	NPC471178
0.7449	Intermediate Similarity	NPC264166
0.7449	Intermediate Similarity	NPC274291
0.7449	Intermediate Similarity	NPC118832
0.7449	Intermediate Similarity	NPC47059
0.7449	Intermediate Similarity	NPC165349
0.7449	Intermediate Similarity	NPC329708
0.7437	Intermediate Similarity	NPC290689
0.7416	Intermediate Similarity	NPC97367
0.7414	Intermediate Similarity	NPC26872
0.7386	Intermediate Similarity	NPC26850
0.7368	Intermediate Similarity	NPC469390
0.7363	Intermediate Similarity	NPC112206
0.7363	Intermediate Similarity	NPC202768
0.7363	Intermediate Similarity	NPC296482
0.7363	Intermediate Similarity	NPC53069
0.7363	Intermediate Similarity	NPC202605
0.736	Intermediate Similarity	NPC285558
0.7358	Intermediate Similarity	NPC267928
0.7353	Intermediate Similarity	NPC473822
0.7348	Intermediate Similarity	NPC476518
0.734	Intermediate Similarity	NPC274982
0.7333	Intermediate Similarity	NPC477019
0.733	Intermediate Similarity	NPC56170
0.7323	Intermediate Similarity	NPC472111
0.731	Intermediate Similarity	NPC471323
0.7308	Intermediate Similarity	NPC121658
0.7308	Intermediate Similarity	NPC14651
0.7292	Intermediate Similarity	NPC279401
0.7292	Intermediate Similarity	NPC79293
0.7286	Intermediate Similarity	NPC313189
0.7283	Intermediate Similarity	NPC288943
0.7282	Intermediate Similarity	NPC287437
0.7273	Intermediate Similarity	NPC289086
0.7263	Intermediate Similarity	NPC471177
0.7263	Intermediate Similarity	NPC124542
0.7263	Intermediate Similarity	NPC59779
0.7258	Intermediate Similarity	NPC222592
0.7258	Intermediate Similarity	NPC168486
0.724	Intermediate Similarity	NPC141915
0.724	Intermediate Similarity	NPC280964
0.724	Intermediate Similarity	NPC114335
0.7234	Intermediate Similarity	NPC62069
0.7234	Intermediate Similarity	NPC320394
0.7225	Intermediate Similarity	NPC76748
0.7217	Intermediate Similarity	NPC201508
0.7208	Intermediate Similarity	NPC155792
0.7208	Intermediate Similarity	NPC232727
0.7202	Intermediate Similarity	NPC307963
0.7192	Intermediate Similarity	NPC96405
0.7192	Intermediate Similarity	NPC171409
0.7188	Intermediate Similarity	NPC92111
0.7178	Intermediate Similarity	NPC123976
0.7178	Intermediate Similarity	NPC167860
0.7173	Intermediate Similarity	NPC296527
0.717	Intermediate Similarity	NPC469792
0.7157	Intermediate Similarity	NPC234197
0.7157	Intermediate Similarity	NPC315957
0.715	Intermediate Similarity	NPC255800
0.715	Intermediate Similarity	NPC96584
0.7129	Intermediate Similarity	NPC174758
0.7129	Intermediate Similarity	NPC469589
0.7128	Intermediate Similarity	NPC251090
0.7127	Intermediate Similarity	NPC263439
0.7127	Intermediate Similarity	NPC474217
0.7122	Intermediate Similarity	NPC235076
0.712	Intermediate Similarity	NPC66083
0.7114	Intermediate Similarity	NPC135549
0.7113	Intermediate Similarity	NPC103230
0.7108	Intermediate Similarity	NPC26679
0.7101	Intermediate Similarity	NPC23614
0.7101	Intermediate Similarity	NPC100079
0.7097	Intermediate Similarity	NPC194724
0.7094	Intermediate Similarity	NPC11464
0.7094	Intermediate Similarity	NPC188420
0.7073	Intermediate Similarity	NPC149471
0.7073	Intermediate Similarity	NPC236668
0.7073	Intermediate Similarity	NPC271215
0.7072	Intermediate Similarity	NPC71079
0.7071	Intermediate Similarity	NPC176538
0.7068	Intermediate Similarity	NPC61350
0.7056	Intermediate Similarity	NPC127085
0.705	Intermediate Similarity	NPC475774
0.7048	Intermediate Similarity	NPC122463
0.7044	Intermediate Similarity	NPC174672
0.7043	Intermediate Similarity	NPC312872
0.7041	Intermediate Similarity	NPC13880
0.7039	Intermediate Similarity	NPC146976
0.7037	Intermediate Similarity	NPC266551
0.7033	Intermediate Similarity	NPC174049
0.7024	Intermediate Similarity	NPC251160
0.7024	Intermediate Similarity	NPC264176
0.7015	Intermediate Similarity	NPC164374
0.7015	Intermediate Similarity	NPC137929
0.7011	Intermediate Similarity	NPC471598
0.701	Intermediate Similarity	NPC470020
0.6995	Remote Similarity	NPC475910
0.6995	Remote Similarity	NPC82548
0.6995	Remote Similarity	NPC44354
0.6989	Remote Similarity	NPC111624
0.6986	Remote Similarity	NPC46451
0.6986	Remote Similarity	NPC193267
0.6986	Remote Similarity	NPC213530
0.6985	Remote Similarity	NPC19872
0.6985	Remote Similarity	NPC329747
0.6976	Remote Similarity	NPC208284
0.6965	Remote Similarity	NPC469440
0.6963	Remote Similarity	NPC284559
0.6961	Remote Similarity	NPC185782
0.6959	Remote Similarity	NPC3715
0.6957	Remote Similarity	NPC278366
0.6957	Remote Similarity	NPC127730
0.6947	Remote Similarity	NPC219963
0.6946	Remote Similarity	NPC475835
0.6942	Remote Similarity	NPC472098
0.6942	Remote Similarity	NPC292517
0.6936	Remote Similarity	NPC245657
0.6927	Remote Similarity	NPC42591
0.6927	Remote Similarity	NPC20249
0.6923	Remote Similarity	NPC170114
0.6919	Remote Similarity	NPC310118
0.6916	Remote Similarity	NPC110151
0.6915	Remote Similarity	NPC150048
0.6915	Remote Similarity	NPC203754
0.6912	Remote Similarity	NPC287208
0.6908	Remote Similarity	NPC162530
0.6906	Remote Similarity	NPC132680
0.6906	Remote Similarity	NPC269919
0.6902	Remote Similarity	NPC85918
0.69	Remote Similarity	NPC329793
0.6895	Remote Similarity	NPC271792
0.6891	Remote Similarity	NPC204385
0.689	Remote Similarity	NPC473513
0.6887	Remote Similarity	NPC118121
0.6881	Remote Similarity	NPC245816
0.6881	Remote Similarity	NPC476138
0.6879	Remote Similarity	NPC280853
0.6875	Remote Similarity	NPC470549
0.6875	Remote Similarity	NPC84478
0.6866	Remote Similarity	NPC469554
0.6859	Remote Similarity	NPC161887
0.6857	Remote Similarity	NPC314270
0.6857	Remote Similarity	NPC204446
0.6856	Remote Similarity	NPC74382
0.6856	Remote Similarity	NPC206251
0.6854	Remote Similarity	NPC322482
0.6848	Remote Similarity	NPC118511
0.6842	Remote Similarity	NPC30570
0.6839	Remote Similarity	NPC285016
0.6832	Remote Similarity	NPC66815
0.6828	Remote Similarity	NPC44161
0.6827	Remote Similarity	NPC471080
0.6827	Remote Similarity	NPC469592
0.6827	Remote Similarity	NPC266931
0.6821	Remote Similarity	NPC471596
0.6821	Remote Similarity	NPC471594
0.6816	Remote Similarity	NPC11017
0.681	Remote Similarity	NPC162812
0.6802	Remote Similarity	NPC471448
0.6802	Remote Similarity	NPC99891
0.6796	Remote Similarity	NPC304179
0.6796	Remote Similarity	NPC48042
0.6796	Remote Similarity	NPC63562
0.6796	Remote Similarity	NPC472550
0.678	Remote Similarity	NPC193238
0.6779	Remote Similarity	NPC280473
0.6779	Remote Similarity	NPC323551
0.6777	Remote Similarity	NPC173080
0.6777	Remote Similarity	NPC469594
0.6773	Remote Similarity	NPC470017
0.6765	Remote Similarity	NPC210256
0.6763	Remote Similarity	NPC219664
0.6762	Remote Similarity	NPC288349
0.6762	Remote Similarity	NPC148183
0.6762	Remote Similarity	NPC152768
0.6762	Remote Similarity	NPC470799
0.6762	Remote Similarity	NPC8022
0.6761	Remote Similarity	NPC253314
0.6753	Remote Similarity	NPC62510
0.6749	Remote Similarity	NPC295898
0.6748	Remote Similarity	NPC476465

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 NPC470474 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	626
0.2-0.3	849
0.3-0.4	1127
0.4-0.5	2963
0.5-0.6	2602
0.6-0.7	649
0.7-0.8	81
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
0.7989	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD3386	Phase 2
0.7857	Intermediate Similarity	NPD4889	Approved
0.7849	Intermediate Similarity	NPD6361	Phase 2
0.7814	Intermediate Similarity	NPD4921	Phase 3
0.7814	Intermediate Similarity	NPD4919	Phase 3
0.7814	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD3921	Approved
0.7796	Intermediate Similarity	NPD6569	Phase 2
0.7796	Intermediate Similarity	NPD3924	Approved
0.7796	Intermediate Similarity	NPD3922	Approved
0.7796	Intermediate Similarity	NPD3923	Approved
0.7722	Intermediate Similarity	NPD1032	Phase 2
0.7672	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD3477	Phase 2
0.7647	Intermediate Similarity	NPD2334	Discontinued
0.7634	Intermediate Similarity	NPD4021	Phase 2
0.7622	Intermediate Similarity	NPD4375	Approved
0.7598	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6298	Discontinued
0.7579	Intermediate Similarity	NPD2482	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7069	Discontinued
0.7527	Intermediate Similarity	NPD5256	Discontinued
0.7513	Intermediate Similarity	NPD6219	Discontinued
0.7513	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD4437	Phase 3
0.7474	Intermediate Similarity	NPD4551	Phase 2
0.7449	Intermediate Similarity	NPD4033	Approved
0.7449	Intermediate Similarity	NPD4035	Approved
0.7449	Intermediate Similarity	NPD4122	Approved
0.7449	Intermediate Similarity	NPD4038	Approved
0.7449	Intermediate Similarity	NPD32	Approved
0.7449	Intermediate Similarity	NPD4037	Approved
0.7449	Intermediate Similarity	NPD4039	Approved
0.7449	Intermediate Similarity	NPD31	Approved
0.7449	Intermediate Similarity	NPD4036	Approved
0.7449	Intermediate Similarity	NPD4034	Approved
0.7448	Intermediate Similarity	NPD1622	Discontinued
0.7436	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1034	Phase 3
0.7386	Intermediate Similarity	NPD2581	Approved
0.7386	Intermediate Similarity	NPD2582	Approved
0.7374	Intermediate Similarity	NPD2780	Approved
0.7374	Intermediate Similarity	NPD2782	Approved
0.7363	Intermediate Similarity	NPD3815	Phase 1
0.7363	Intermediate Similarity	NPD3816	Phase 1
0.736	Intermediate Similarity	NPD4795	Phase 2
0.7358	Intermediate Similarity	NPD1229	Phase 2
0.7358	Intermediate Similarity	NPD4899	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2600	Approved
0.7351	Intermediate Similarity	NPD2601	Approved
0.7351	Intermediate Similarity	NPD2599	Approved
0.7344	Intermediate Similarity	NPD3395	Approved
0.7344	Intermediate Similarity	NPD3396	Approved
0.7337	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4072	Approved
0.7337	Intermediate Similarity	NPD4071	Approved
0.733	Intermediate Similarity	NPD4372	Phase 1
0.7316	Intermediate Similarity	NPD8063	Discontinued
0.7293	Intermediate Similarity	NPD2781	Approved
0.7268	Intermediate Similarity	NPD2952	Discontinued
0.7254	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD3039	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7134	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD3920	Phase 2
0.7202	Intermediate Similarity	NPD1038	Approved
0.7202	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD1739	Approved
0.7157	Intermediate Similarity	NPD1740	Approved
0.7128	Intermediate Similarity	NPD4204	Approved
0.7128	Intermediate Similarity	NPD4203	Approved
0.7111	Intermediate Similarity	NPD1418	Phase 2
0.7107	Intermediate Similarity	NPD4052	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2332	Discontinued
0.7068	Intermediate Similarity	NPD7758	Approved
0.7068	Intermediate Similarity	NPD7757	Approved
0.7062	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6550	Discontinued
0.7039	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7426	Phase 1
0.7028	Intermediate Similarity	NPD7674	Phase 3
0.7028	Intermediate Similarity	NPD7675	Phase 3
0.7021	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD687	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3397	Phase 2
0.7011	Intermediate Similarity	NPD3813	Approved
0.701	Intermediate Similarity	NPD6262	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4148	Approved
0.7005	Intermediate Similarity	NPD6772	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2076	Approved
0.6989	Remote Similarity	NPD2077	Approved
0.6986	Remote Similarity	NPD6500	Approved
0.6986	Remote Similarity	NPD3763	Approved
0.6986	Remote Similarity	NPD6501	Approved
0.6979	Remote Similarity	NPD2917	Approved
0.6959	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6528	Phase 1
0.6946	Remote Similarity	NPD7222	Phase 2
0.6946	Remote Similarity	NPD1392	Approved
0.694	Remote Similarity	NPD6635	Approved
0.6935	Remote Similarity	NPD2958	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3825	Phase 3
0.6935	Remote Similarity	NPD5999	Phase 2
0.6931	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2959	Phase 3
0.6912	Remote Similarity	NPD7558	Phase 2
0.6912	Remote Similarity	NPD7467	Discontinued
0.6906	Remote Similarity	NPD9382	Approved
0.6906	Remote Similarity	NPD9383	Approved
0.6904	Remote Similarity	NPD4418	Discontinued
0.6904	Remote Similarity	NPD6590	Discontinued
0.6902	Remote Similarity	NPD926	Approved
0.6902	Remote Similarity	NPD925	Approved
0.6897	Remote Similarity	NPD5601	Phase 2
0.6893	Remote Similarity	NPD5067	Phase 2
0.6893	Remote Similarity	NPD5066	Phase 2
0.6893	Remote Similarity	NPD4131	Phase 3
0.689	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5513	Phase 2
0.6881	Remote Similarity	NPD2757	Phase 2
0.6878	Remote Similarity	NPD6529	Discontinued
0.6872	Remote Similarity	NPD8479	Phase 2
0.6868	Remote Similarity	NPD5255	Approved
0.6866	Remote Similarity	NPD5437	Clinical (unspecified phase)
0.685	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.685	Remote Similarity	NPD4548	Discontinued
0.6847	Remote Similarity	NPD2831	Approved
0.6844	Remote Similarity	NPD4369	Phase 2
0.6842	Remote Similarity	NPD5612	Discontinued
0.684	Remote Similarity	NPD5147	Discontinued
0.6839	Remote Similarity	NPD6227	Discontinued
0.6839	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6494	Phase 2
0.6834	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7886	Phase 2
0.6833	Remote Similarity	NPD6357	Discontinued
0.6833	Remote Similarity	NPD7885	Phase 2
0.6831	Remote Similarity	NPD9705	Discontinued
0.6831	Remote Similarity	NPD112	Approved
0.6829	Remote Similarity	NPD5529	Phase 1
0.6829	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6728	Phase 3
0.6791	Remote Similarity	NPD5319	Approved
0.6791	Remote Similarity	NPD5320	Approved
0.6789	Remote Similarity	NPD6642	Approved
0.6789	Remote Similarity	NPD6641	Approved
0.6788	Remote Similarity	NPD3569	Discontinued
0.6787	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2885	Approved
0.678	Remote Similarity	NPD7452	Approved
0.678	Remote Similarity	NPD2886	Approved
0.678	Remote Similarity	NPD7453	Approved
0.6777	Remote Similarity	NPD6568	Discontinued
0.6776	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD8020	Approved
0.6769	Remote Similarity	NPD8021	Approved
0.6763	Remote Similarity	NPD9506	Approved
0.6758	Remote Similarity	NPD6026	Approved
0.6755	Remote Similarity	NPD2123	Phase 3
0.675	Remote Similarity	NPD4673	Phase 2
0.6748	Remote Similarity	NPD5658	Approved
0.6748	Remote Similarity	NPD2189	Approved
0.6748	Remote Similarity	NPD2187	Approved
0.6745	Remote Similarity	NPD3402	Phase 1
0.674	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5862	Discovery
0.6737	Remote Similarity	NPD5100	Phase 3
0.6735	Remote Similarity	NPD4681	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3003	Approved
0.673	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1352	Discontinued
0.6716	Remote Similarity	NPD6991	Approved
0.6713	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD7051	Phase 3
0.6701	Remote Similarity	NPD1213	Phase 3
0.6701	Remote Similarity	NPD6281	Approved
0.67	Remote Similarity	NPD5512	Phase 3
0.67	Remote Similarity	NPD5259	Phase 3
0.6698	Remote Similarity	NPD3354	Phase 2
0.6697	Remote Similarity	NPD7567	Approved
0.6684	Remote Similarity	NPD425	Approved
0.6684	Remote Similarity	NPD424	Approved
0.6683	Remote Similarity	NPD4528	Approved
0.6683	Remote Similarity	NPD4526	Approved
0.6683	Remote Similarity	NPD4529	Approved
0.6682	Remote Similarity	NPD4923	Phase 1
0.6667	Remote Similarity	NPD5944	Phase 1
0.6667	Remote Similarity	NPD5998	Clinical (unspecified phase)

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