NPASS Compound

Structure

NPC2497 OpenBabel07101718182D 43 51 0 0 1 0 0 0 0 0999 V2000 0.8485 3.4291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0768 2.6404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0299 3.1096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6970 2.9392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1247 2.4096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8146 2.5231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4091 -0.8975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4403 -1.0436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3457 0.2028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1658 4.5117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7670 0.0145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8294 -0.2776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1423 2.2744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4021 0.9559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5978 4.0363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8916 4.3640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7217 -0.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0984 3.2532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3939 1.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3939 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0313 2.7539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8485 0.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6970 1.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1562 0.7805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3167 1.7470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5454 1.4696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2424 1.4696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8485 1.4696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5454 0.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1874 0.6344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0909 1.9595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2424 0.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4471 2.1983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4031 3.1770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8485 0.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8485 1.4696 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6153 3.2958 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6970 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.2287 3.7045 0.0000 N 0 0 3 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 5.7491 1.5107 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0909 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 4 24 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 25 2 0 0 0 0 12 31 2 0 0 0 0 13 18 1 0 0 0 0 13 26 1 0 0 0 0 14 37 1 0 0 0 0 15 38 1 0 0 0 0 16 40 1 0 0 0 0 17 41 1 0 0 0 0 18 40 1 0 0 0 0 19 27 2 0 0 0 0 19 28 1 0 0 0 0 20 30 2 0 0 0 0 20 33 1 0 0 0 0 21 29 1 0 0 0 0 21 37 1 0 0 0 0 22 32 1 0 0 0 0 22 38 1 0 0 0 0 23 37 1 0 0 0 0 23 41 1 0 0 0 0 24 27 1 0 0 0 0 24 29 2 0 0 0 0 25 26 1 0 0 0 0 25 31 1 0 0 0 0 26 34 2 0 0 0 0 27 30 1 0 0 0 0 28 33 2 0 0 0 0 29 36 1 0 0 0 0 30 39 1 0 0 0 0 31 42 1 0 0 0 0 32 28 1 6 0 0 0 32 42 1 0 0 0 0 33 43 1 0 0 0 0 34 35 1 0 0 0 0 34 42 1 0 0 0 0 35 38 1 1 0 0 0 35 40 1 0 0 0 0 36 39 2 0 0 0 0 36 41 1 0 0 0 0 37 5 1 1 0 0 0 38 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.35
Volume:	615.208
LogP:	8.227
LogD:	5.433
LogS:	-6.958
# Rotatable Bonds:	4
TPSA:	44.53
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.268
Synthetic Accessibility Score:	5.56
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.435
MDCK Permeability:	1.0120796105184127e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.924
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.872
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.512
Plasma Protein Binding (PPB):	98.30789184570312%
Volume Distribution (VD):	2.299
Pgp-substrate:	1.525539755821228%

ADMET: Metabolism

CYP1A2-inhibitor:	0.143
CYP1A2-substrate:	0.873
CYP2C19-inhibitor:	0.186
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.191
CYP2C9-substrate:	0.126
CYP2D6-inhibitor:	0.871
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	3.695
Half-life (T1/2):	0.012

ADMET: Toxicity

hERG Blockers:	0.827
Human Hepatotoxicity (H-HT):	0.997
Drug-inuced Liver Injury (DILI):	0.789
AMES Toxicity:	0.672
Rat Oral Acute Toxicity:	0.207
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.144
Carcinogencity:	0.41
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.26

Download Data

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

Natural Product: NPC2497

Natural Product ID:	NPC2497
*Common Name:**	Leucophyllidine
IUPAC Name:	n.a.
Synonyms:	Leucophyllidine
Standard InCHIKey:	ZEWZJFWYVWSQKO-LOCAODKASA-N
Standard InCHI:	InChI=1S/C38H44N4O/c1-4-24-27-19-28(33(43)20-30(27)39-36-29(24)21-37(5-2)14-9-17-41(36)23-37)32-22-38(6-3)15-10-16-40-18-13-26-25-11-7-8-12-31(25)42(32)34(26)35(38)40/h4,7-8,11-12,19-20,32,35,43H,1,5-6,9-10,13-18,21-23H2,2-3H3/t32-,35-,37+,38+/m0/s1
SMILES:	C=Cc1c2cc([C@@H]3C[C@@]4(CC)CCCN5CCc6c7ccccc7n3c6[C@@H]45)c(cc2nc2c1C[C@@]1(CC)CCCN2C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1269167
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002671] Eburnan-type alkaloids

*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
NPO32918	leuconotis eugenifolius	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20836516]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7100.0	nM	PMID[567429]

☑ 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 NPC2497 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	737
0.1-0.2	4043
0.2-0.3	13030
0.3-0.4	15276
0.4-0.5	5256
0.5-0.6	3095
0.6-0.7	1170
0.7-0.8	87
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8465	Intermediate Similarity	NPC162748
0.8102	Intermediate Similarity	NPC183407
0.7946	Intermediate Similarity	NPC253580
0.7743	Intermediate Similarity	NPC470126
0.7716	Intermediate Similarity	NPC477861
0.7702	Intermediate Similarity	NPC469734
0.7621	Intermediate Similarity	NPC103687
0.7621	Intermediate Similarity	NPC132631
0.7585	Intermediate Similarity	NPC94943
0.7536	Intermediate Similarity	NPC190007
0.7534	Intermediate Similarity	NPC470931
0.7488	Intermediate Similarity	NPC212535
0.7467	Intermediate Similarity	NPC214980
0.7421	Intermediate Similarity	NPC469589
0.7373	Intermediate Similarity	NPC249040
0.7345	Intermediate Similarity	NPC476041
0.7345	Intermediate Similarity	NPC304926
0.7321	Intermediate Similarity	NPC471603
0.7294	Intermediate Similarity	NPC11017
0.7273	Intermediate Similarity	NPC144114
0.7273	Intermediate Similarity	NPC53144
0.7265	Intermediate Similarity	NPC476116
0.7235	Intermediate Similarity	NPC243834
0.7235	Intermediate Similarity	NPC70956
0.7235	Intermediate Similarity	NPC153042
0.723	Intermediate Similarity	NPC472289
0.721	Intermediate Similarity	NPC473185
0.7205	Intermediate Similarity	NPC213530
0.7205	Intermediate Similarity	NPC193267
0.7195	Intermediate Similarity	NPC200836
0.719	Intermediate Similarity	NPC475666
0.7177	Intermediate Similarity	NPC72980
0.7174	Intermediate Similarity	NPC477533
0.7162	Intermediate Similarity	NPC475070
0.7155	Intermediate Similarity	NPC130570
0.7149	Intermediate Similarity	NPC330009
0.7149	Intermediate Similarity	NPC475112
0.7149	Intermediate Similarity	NPC475085
0.7149	Intermediate Similarity	NPC291535
0.7149	Intermediate Similarity	NPC81939
0.7143	Intermediate Similarity	NPC475910
0.7143	Intermediate Similarity	NPC477532
0.713	Intermediate Similarity	NPC472111
0.7112	Intermediate Similarity	NPC280272
0.711	Intermediate Similarity	NPC242209
0.711	Intermediate Similarity	NPC472193
0.7095	Intermediate Similarity	NPC133261
0.7093	Intermediate Similarity	NPC294620
0.708	Intermediate Similarity	NPC85273
0.708	Intermediate Similarity	NPC167860
0.708	Intermediate Similarity	NPC123976
0.7067	Intermediate Similarity	NPC208060
0.7067	Intermediate Similarity	NPC474409
0.7064	Intermediate Similarity	NPC6215
0.7062	Intermediate Similarity	NPC187827
0.7062	Intermediate Similarity	NPC472105
0.7061	Intermediate Similarity	NPC469592
0.7061	Intermediate Similarity	NPC471080
0.7059	Intermediate Similarity	NPC329747
0.7051	Intermediate Similarity	NPC324149
0.7039	Intermediate Similarity	NPC220851
0.7028	Intermediate Similarity	NPC477891
0.7018	Intermediate Similarity	NPC264176
0.701	Intermediate Similarity	NPC255229
0.701	Intermediate Similarity	NPC81229
0.7009	Intermediate Similarity	NPC285558
0.7	Intermediate Similarity	NPC295228
0.6991	Remote Similarity	NPC246700
0.6986	Remote Similarity	NPC471294
0.6983	Remote Similarity	NPC473179
0.6978	Remote Similarity	NPC474145
0.6978	Remote Similarity	NPC475841
0.6975	Remote Similarity	NPC475253
0.6975	Remote Similarity	NPC476451
0.6971	Remote Similarity	NPC473183
0.6967	Remote Similarity	NPC326575
0.6964	Remote Similarity	NPC472066
0.6964	Remote Similarity	NPC472031
0.6964	Remote Similarity	NPC472067
0.6958	Remote Similarity	NPC473184
0.6957	Remote Similarity	NPC237740
0.6955	Remote Similarity	NPC70259
0.6947	Remote Similarity	NPC193777
0.6944	Remote Similarity	NPC46580
0.6944	Remote Similarity	NPC254762
0.6942	Remote Similarity	NPC30540
0.694	Remote Similarity	NPC469594
0.6938	Remote Similarity	NPC476686
0.6938	Remote Similarity	NPC476688
0.6938	Remote Similarity	NPC105758
0.6934	Remote Similarity	NPC88363
0.6933	Remote Similarity	NPC209174
0.693	Remote Similarity	NPC475422
0.6926	Remote Similarity	NPC39092
0.6923	Remote Similarity	NPC278874
0.6919	Remote Similarity	NPC472122
0.6919	Remote Similarity	NPC24594
0.6916	Remote Similarity	NPC87755
0.6909	Remote Similarity	NPC205934
0.6909	Remote Similarity	NPC43787
0.6904	Remote Similarity	NPC477531
0.6903	Remote Similarity	NPC476106
0.6898	Remote Similarity	NPC314573
0.6892	Remote Similarity	NPC72211
0.6891	Remote Similarity	NPC252251
0.6889	Remote Similarity	NPC223427
0.6881	Remote Similarity	NPC469497
0.6881	Remote Similarity	NPC106833
0.6875	Remote Similarity	NPC267423
0.687	Remote Similarity	NPC112206
0.687	Remote Similarity	NPC48353
0.687	Remote Similarity	NPC202605
0.6864	Remote Similarity	NPC329541
0.6858	Remote Similarity	NPC470500
0.6857	Remote Similarity	NPC158129
0.6856	Remote Similarity	NPC5145
0.6856	Remote Similarity	NPC11464
0.6851	Remote Similarity	NPC473317
0.6847	Remote Similarity	NPC474188
0.6844	Remote Similarity	NPC211813
0.6835	Remote Similarity	NPC128751
0.6827	Remote Similarity	NPC471178
0.6826	Remote Similarity	NPC23294
0.6825	Remote Similarity	NPC472123
0.682	Remote Similarity	NPC314954
0.6818	Remote Similarity	NPC99666
0.6818	Remote Similarity	NPC280964
0.6818	Remote Similarity	NPC141915
0.6818	Remote Similarity	NPC114335
0.6815	Remote Similarity	NPC472068
0.6812	Remote Similarity	NPC124542
0.6812	Remote Similarity	NPC59779
0.6812	Remote Similarity	NPC471177
0.6812	Remote Similarity	NPC174758
0.681	Remote Similarity	NPC470549
0.681	Remote Similarity	NPC164664
0.6806	Remote Similarity	NPC472294
0.6803	Remote Similarity	NPC41679
0.68	Remote Similarity	NPC476044
0.68	Remote Similarity	NPC232727
0.6798	Remote Similarity	NPC53344
0.6787	Remote Similarity	NPC473178
0.6783	Remote Similarity	NPC303951
0.6781	Remote Similarity	NPC469928
0.6781	Remote Similarity	NPC170114
0.6776	Remote Similarity	NPC232340
0.6769	Remote Similarity	NPC477111
0.6765	Remote Similarity	NPC125597
0.6762	Remote Similarity	NPC285343
0.6762	Remote Similarity	NPC28945
0.6759	Remote Similarity	NPC472104
0.6759	Remote Similarity	NPC472110
0.6759	Remote Similarity	NPC133306
0.6759	Remote Similarity	NPC472109
0.6757	Remote Similarity	NPC131017
0.675	Remote Similarity	NPC471762
0.6748	Remote Similarity	NPC81175
0.6744	Remote Similarity	NPC478032
0.6741	Remote Similarity	NPC306376
0.674	Remote Similarity	NPC162484
0.674	Remote Similarity	NPC469440
0.6739	Remote Similarity	NPC174672
0.6739	Remote Similarity	NPC209769
0.6737	Remote Similarity	NPC132642
0.6736	Remote Similarity	NPC202503
0.6732	Remote Similarity	NPC63109
0.6731	Remote Similarity	NPC224632
0.6729	Remote Similarity	NPC96890
0.6723	Remote Similarity	NPC473041
0.6722	Remote Similarity	NPC326363
0.6721	Remote Similarity	NPC473312
0.6721	Remote Similarity	NPC295452
0.6721	Remote Similarity	NPC171393
0.6715	Remote Similarity	NPC84508
0.6711	Remote Similarity	NPC16452
0.6711	Remote Similarity	NPC476167
0.6711	Remote Similarity	NPC36229
0.6711	Remote Similarity	NPC476581
0.6708	Remote Similarity	NPC220852
0.6696	Remote Similarity	NPC210828
0.6696	Remote Similarity	NPC86834
0.6696	Remote Similarity	NPC295898
0.6682	Remote Similarity	NPC19679
0.6682	Remote Similarity	NPC203754
0.6682	Remote Similarity	NPC150048
0.6682	Remote Similarity	NPC134586
0.6681	Remote Similarity	NPC476121
0.6681	Remote Similarity	NPC305984
0.6681	Remote Similarity	NPC329793
0.6681	Remote Similarity	NPC476124
0.6681	Remote Similarity	NPC477113
0.6681	Remote Similarity	NPC242923
0.668	Remote Similarity	NPC325976
0.668	Remote Similarity	NPC17437
0.6667	Remote Similarity	NPC192315
0.6667	Remote Similarity	NPC15840
0.6667	Remote Similarity	NPC201697
0.6667	Remote Similarity	NPC265576
0.6667	Remote Similarity	NPC474183
0.6667	Remote Similarity	NPC24370

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 NPC2497 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	594
0.2-0.3	905
0.3-0.4	1788
0.4-0.5	2548
0.5-0.6	2125
0.6-0.7	807
0.7-0.8	34
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8531	High Similarity	NPD7112	Discontinued
0.7665	Intermediate Similarity	NPD6327	Phase 1
0.7653	Intermediate Similarity	NPD3814	Phase 1
0.7588	Intermediate Similarity	NPD6326	Phase 2
0.75	Intermediate Similarity	NPD6307	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD7726	Phase 1
0.743	Intermediate Similarity	NPD7935	Phase 2
0.7424	Intermediate Similarity	NPD4401	Phase 2
0.7424	Intermediate Similarity	NPD4403	Phase 3
0.7416	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4511	Phase 1
0.7311	Intermediate Similarity	NPD3872	Phase 3
0.7302	Intermediate Similarity	NPD4999	Phase 3
0.7302	Intermediate Similarity	NPD4998	Phase 3
0.7295	Intermediate Similarity	NPD7111	Discontinued
0.7269	Intermediate Similarity	NPD7423	Phase 2
0.7252	Intermediate Similarity	NPD1197	Approved
0.7244	Intermediate Similarity	NPD2794	Discontinued
0.7202	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5413	Phase 2
0.7178	Intermediate Similarity	NPD6573	Phase 3
0.7178	Intermediate Similarity	NPD6572	Phase 2
0.7175	Intermediate Similarity	NPD7222	Phase 2
0.7174	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7948	Phase 1
0.7143	Intermediate Similarity	NPD2916	Discontinued
0.7143	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6501	Approved
0.713	Intermediate Similarity	NPD6500	Approved
0.713	Intermediate Similarity	NPD5530	Phase 1
0.713	Intermediate Similarity	NPD7568	Phase 1
0.7107	Intermediate Similarity	NPD7067	Approved
0.7107	Intermediate Similarity	NPD7068	Approved
0.7105	Intermediate Similarity	NPD7188	Phase 3
0.7089	Intermediate Similarity	NPD2762	Phase 2
0.7072	Intermediate Similarity	NPD6975	Discontinued
0.707	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6490	Phase 2
0.705	Intermediate Similarity	NPD2882	Phase 1
0.7035	Intermediate Similarity	NPD7409	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6592	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3403	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5428	Discontinued
0.7009	Intermediate Similarity	NPD5425	Phase 1
0.7004	Intermediate Similarity	NPD8321	Discontinued
0.6996	Remote Similarity	NPD6132	Phase 1
0.6986	Remote Similarity	NPD3224	Phase 2
0.6983	Remote Similarity	NPD4858	Phase 2
0.6968	Remote Similarity	NPD5885	Approved
0.6967	Remote Similarity	NPD7620	Phase 2
0.6967	Remote Similarity	NPD6159	Phase 2
0.6966	Remote Similarity	NPD1954	Phase 1
0.6947	Remote Similarity	NPD7452	Approved
0.6947	Remote Similarity	NPD7453	Approved
0.6934	Remote Similarity	NPD8386	Phase 2
0.6933	Remote Similarity	NPD6969	Phase 2
0.6933	Remote Similarity	NPD6968	Phase 2
0.6903	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4945	Discontinued
0.6891	Remote Similarity	NPD7767	Approved
0.6888	Remote Similarity	NPD2757	Phase 2
0.6883	Remote Similarity	NPD7996	Phase 2
0.6881	Remote Similarity	NPD6158	Phase 2
0.6881	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6856	Discontinued
0.6878	Remote Similarity	NPD6352	Phase 2
0.6877	Remote Similarity	NPD7923	Phase 2
0.6867	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2383	Phase 1
0.6857	Remote Similarity	NPD6473	Phase 1
0.6853	Remote Similarity	NPD6957	Approved
0.6853	Remote Similarity	NPD6958	Approved
0.6842	Remote Similarity	NPD4612	Discontinued
0.6842	Remote Similarity	NPD5658	Approved
0.684	Remote Similarity	NPD6742	Phase 2
0.684	Remote Similarity	NPD6743	Phase 2
0.6838	Remote Similarity	NPD7168	Phase 3
0.6835	Remote Similarity	NPD6363	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD8049	Phase 2
0.6824	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3234	Phase 3
0.6822	Remote Similarity	NPD3233	Phase 2
0.6816	Remote Similarity	NPD7419	Discontinued
0.6814	Remote Similarity	NPD4886	Phase 2
0.681	Remote Similarity	NPD1325	Approved
0.681	Remote Similarity	NPD1326	Approved
0.6804	Remote Similarity	NPD2410	Phase 2
0.6803	Remote Similarity	NPD6750	Phase 2
0.6803	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6594	Discontinued
0.6802	Remote Similarity	NPD6230	Discontinued
0.6798	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5874	Phase 3
0.6789	Remote Similarity	NPD5873	Phase 3
0.6787	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7706	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3013	Phase 3
0.6783	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6711	Approved
0.6777	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7415	Suspended
0.6777	Remote Similarity	NPD7558	Phase 2
0.6773	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7194	Discontinued
0.6766	Remote Similarity	NPD4312	Approved
0.6765	Remote Similarity	NPD6246	Approved
0.6761	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7221	Approved
0.6751	Remote Similarity	NPD7219	Approved
0.6744	Remote Similarity	NPD2599	Approved
0.6744	Remote Similarity	NPD2601	Approved
0.6744	Remote Similarity	NPD2600	Approved
0.6742	Remote Similarity	NPD6887	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4615	Phase 2
0.6736	Remote Similarity	NPD7675	Phase 3
0.6736	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7674	Phase 3
0.6729	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD3439	Approved
0.6724	Remote Similarity	NPD3330	Phase 1
0.6724	Remote Similarity	NPD6202	Discontinued
0.6719	Remote Similarity	NPD8442	Discontinued
0.6712	Remote Similarity	NPD6350	Phase 1
0.6711	Remote Similarity	NPD5828	Phase 2
0.6708	Remote Similarity	NPD6164	Phase 2
0.6708	Remote Similarity	NPD6186	Approved
0.6708	Remote Similarity	NPD6165	Phase 2
0.6708	Remote Similarity	NPD4306	Phase 1
0.6707	Remote Similarity	NPD8016	Phase 3
0.6707	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7081	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4673	Phase 2
0.6695	Remote Similarity	NPD4457	Phase 2
0.6695	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5802	Phase 2
0.6694	Remote Similarity	NPD7592	Phase 2
0.6694	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD2536	Discontinued
0.6681	Remote Similarity	NPD1838	Clinical (unspecified phase)
0.668	Remote Similarity	NPD6970	Phase 2
0.668	Remote Similarity	NPD8358	Approved
0.668	Remote Similarity	NPD6760	Discontinued
0.6667	Remote Similarity	NPD6619	Phase 3
0.6667	Remote Similarity	NPD7051	Phase 3
0.6667	Remote Similarity	NPD1599	Approved
0.6667	Remote Similarity	NPD6605	Phase 3
0.6667	Remote Similarity	NPD4350	Approved
0.6667	Remote Similarity	NPD7705	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2917	Approved
0.6667	Remote Similarity	NPD6452	Discontinued
0.6667	Remote Similarity	NPD7603	Discontinued
0.6667	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6469	Phase 3
0.6667	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4349	Approved
0.6667	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD8525	Approved
0.6653	Remote Similarity	NPD7857	Phase 3
0.6653	Remote Similarity	NPD7856	Phase 2
0.6652	Remote Similarity	NPD3816	Phase 1
0.6652	Remote Similarity	NPD3815	Phase 1
0.6652	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.664	Remote Similarity	NPD5905	Phase 1
0.6639	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6643	Discontinued
0.6637	Remote Similarity	NPD8395	Approved
0.6637	Remote Similarity	NPD802	Phase 2
0.6637	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD8396	Approved
0.6636	Remote Similarity	NPD7867	Phase 1
0.6636	Remote Similarity	NPD6492	Phase 2
0.6636	Remote Similarity	NPD4203	Approved
0.6636	Remote Similarity	NPD4204	Approved
0.6636	Remote Similarity	NPD8408	Discontinued
0.6636	Remote Similarity	NPD7394	Phase 2
0.6635	Remote Similarity	NPD6794	Approved
0.6627	Remote Similarity	NPD6244	Phase 3
0.6627	Remote Similarity	NPD6243	Phase 3
0.6626	Remote Similarity	NPD8004	Discontinued
0.6625	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7506	Discontinued
0.6623	Remote Similarity	NPD7665	Phase 2
0.6623	Remote Similarity	NPD7666	Phase 3
0.6623	Remote Similarity	NPD7672	Approved
0.6623	Remote Similarity	NPD7671	Approved
0.6621	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6227	Discontinued
0.6618	Remote Similarity	NPD2469	Approved
0.6618	Remote Similarity	NPD2468	Approved
0.6614	Remote Similarity	NPD5876	Phase 3
0.6614	Remote Similarity	NPD5877	Phase 3
0.6612	Remote Similarity	NPD7555	Discontinued
0.6612	Remote Similarity	NPD3838	Phase 3
0.6609	Remote Similarity	NPD6150	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data