NPASS Compound

Structure

NPC471386 OpenBabel07101719252D 43 52 0 0 1 0 0 0 0 0999 V2000 4.2544 -1.7344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.9168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5385 -1.0362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4123 1.7258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9625 0.9004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4542 -0.9723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9625 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2396 0.2104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3668 1.2443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5373 -1.7495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3668 -0.1314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1080 0.6159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1169 1.5380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7173 -0.9846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8671 1.8820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0520 -0.3456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3665 -2.5470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8086 1.5380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8600 -0.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9093 2.0715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4043 0.5565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1169 -0.6878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5759 -1.3071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5823 1.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7711 0.9004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1169 1.1129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3291 -2.2761 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8086 1.1129 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0585 0.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7126 -1.2443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4057 -1.3440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7711 0.2126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1911 -0.1613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6506 -1.8488 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0585 1.8820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7126 0.5565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5215 -1.0830 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3473 -1.9136 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8974 -0.8797 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.4628 2.0133 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1169 -0.0000 0.0000 N 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 0.4707 2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 23 2 0 0 0 0 4 24 2 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 25 2 0 0 0 0 10 31 2 0 0 0 0 11 32 2 0 0 0 0 12 33 2 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 15 40 1 0 0 0 0 16 39 1 0 0 0 0 17 34 1 0 0 0 0 18 35 1 0 0 0 0 19 23 1 0 0 0 0 19 39 1 0 0 0 0 20 24 1 0 0 0 0 20 40 1 0 0 0 0 21 29 2 0 0 0 0 21 42 1 0 0 0 0 22 30 2 0 0 0 0 22 41 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 26 1 0 0 0 0 25 32 1 0 0 0 0 26 36 2 0 0 0 0 27 17 1 6 0 0 0 27 30 1 0 0 0 0 28 18 1 1 0 0 0 28 29 1 0 0 0 0 29 36 1 0 0 0 0 30 37 1 0 0 0 0 31 33 1 0 0 0 0 31 38 1 0 0 0 0 32 41 1 0 0 0 0 33 42 1 0 0 0 0 34 38 1 1 0 0 0 34 39 1 0 0 0 0 35 40 1 0 0 0 0 35 43 2 0 0 0 0 36 41 1 0 0 0 0 37 38 1 1 0 0 0 37 42 1 0 0 0 0 38 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	566.3
Volume:	601.379
LogP:	5.757
LogD:	4.762
LogS:	-6.318
# Rotatable Bonds:	0
TPSA:	31.72
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	11
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	7.123
Fsp3:	0.395
Lipinski Rule-of-5:	Rejected
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:	-5.317
MDCK Permeability:	2.7621603294392116e-05
Pgp-inhibitor:	0.967
Pgp-substrate:	0.766
Human Intestinal Absorption (HIA):	0.877
20% Bioavailability (F20%):	0.837
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.604
Plasma Protein Binding (PPB):	88.66057586669922%
Volume Distribution (VD):	1.417
Pgp-substrate:	2.744694232940674%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.84
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.869
CYP2C9-substrate:	0.595
CYP2D6-inhibitor:	0.944
CYP2D6-substrate:	0.816
CYP3A4-inhibitor:	0.901
CYP3A4-substrate:	0.915

ADMET: Excretion

Clearance (CL):	8.253
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.168
Human Hepatotoxicity (H-HT):	0.653
Drug-inuced Liver Injury (DILI):	0.325
AMES Toxicity:	0.152
Rat Oral Acute Toxicity:	0.985
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.669
Carcinogencity:	0.782
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC471386

Natural Product ID:	NPC471386
*Common Name:**	(15S,19E,2's,3's,7'r,15's,19'e)-Gardovatine
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OSKKNZHUYWQWKZ-SWNWXBJPSA-N
Standard InCHI:	InChI=1S/C38H38N4O/c1-3-23-19-39-16-14-38-31-10-6-8-12-33(31)42-21-29-28-18-35(43)40(20-24(28)4-2)15-13-26-25-9-5-7-11-32(25)41(36(26)29)22-30(37(38)42)27(23)17-34(38)39/h3-12,21-22,27-28,34,37H,13-20H2,1-2H3/b23-3-,24-4-,29-21-,30-22-/t27-,28-,34-,37-,38+/m0/s1
SMILES:	CC=C1CN2CCC34C2CC1C5=CN6C7=CC=CC=C7C8=C6C(=CN(C53)C9=CC=CC=C49)C1CC(=O)N(CC8)CC1=CC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2430444
PubChem CID:	72192891
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos 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
NPO32800	gardneria oveta	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24012119]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	16100.0	nM	PMID[559283]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	13900.0	nM	PMID[559283]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	14200.0	nM	PMID[559283]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	10500.0	nM	PMID[559283]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	9800.0	nM	PMID[559283]

☑ 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 NPC471386 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	598
0.1-0.2	3018
0.2-0.3	20882
0.3-0.4	11857
0.4-0.5	2575
0.5-0.6	2382
0.6-0.7	1220
0.7-0.8	162
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
0.8171	Intermediate Similarity	NPC194881
0.7857	Intermediate Similarity	NPC161861
0.7727	Intermediate Similarity	NPC200743
0.7637	Intermediate Similarity	NPC56233
0.7527	Intermediate Similarity	NPC271797
0.7527	Intermediate Similarity	NPC21174
0.75	Intermediate Similarity	NPC104483
0.75	Intermediate Similarity	NPC248462
0.7487	Intermediate Similarity	NPC308931
0.7487	Intermediate Similarity	NPC99939
0.7475	Intermediate Similarity	NPC477065
0.7471	Intermediate Similarity	NPC20144
0.7368	Intermediate Similarity	NPC477714
0.7363	Intermediate Similarity	NPC221786
0.7363	Intermediate Similarity	NPC474880
0.7363	Intermediate Similarity	NPC475990
0.7358	Intermediate Similarity	NPC478077
0.7354	Intermediate Similarity	NPC64436
0.7344	Intermediate Similarity	NPC472119
0.7322	Intermediate Similarity	NPC229173
0.7312	Intermediate Similarity	NPC475248
0.7312	Intermediate Similarity	NPC63047
0.7292	Intermediate Similarity	NPC470205
0.7292	Intermediate Similarity	NPC143533
0.7283	Intermediate Similarity	NPC469741
0.7277	Intermediate Similarity	NPC15840
0.7273	Intermediate Similarity	NPC474897
0.7273	Intermediate Similarity	NPC470731
0.7268	Intermediate Similarity	NPC141612
0.7268	Intermediate Similarity	NPC135601
0.7268	Intermediate Similarity	NPC17273
0.7268	Intermediate Similarity	NPC87755
0.7264	Intermediate Similarity	NPC474896
0.7254	Intermediate Similarity	NPC258480
0.7238	Intermediate Similarity	NPC477715
0.723	Intermediate Similarity	NPC253987
0.723	Intermediate Similarity	NPC31097
0.722	Intermediate Similarity	NPC54420
0.7216	Intermediate Similarity	NPC472107
0.7216	Intermediate Similarity	NPC133003
0.7216	Intermediate Similarity	NPC79062
0.7198	Intermediate Similarity	NPC475422
0.7198	Intermediate Similarity	NPC126066
0.7188	Intermediate Similarity	NPC91179
0.7179	Intermediate Similarity	NPC66210
0.7165	Intermediate Similarity	NPC472294
0.7163	Intermediate Similarity	NPC19170
0.7151	Intermediate Similarity	NPC478182
0.715	Intermediate Similarity	NPC327095
0.715	Intermediate Similarity	NPC162860
0.715	Intermediate Similarity	NPC312942
0.7143	Intermediate Similarity	NPC297862
0.7136	Intermediate Similarity	NPC272174
0.7135	Intermediate Similarity	NPC81229
0.7135	Intermediate Similarity	NPC255229
0.7127	Intermediate Similarity	NPC40070
0.7121	Intermediate Similarity	NPC473763
0.7121	Intermediate Similarity	NPC117244
0.7116	Intermediate Similarity	NPC40455
0.7095	Intermediate Similarity	NPC469735
0.7095	Intermediate Similarity	NPC470440
0.7083	Intermediate Similarity	NPC234987
0.7079	Intermediate Similarity	NPC171317
0.7064	Intermediate Similarity	NPC56109
0.7064	Intermediate Similarity	NPC191382
0.7062	Intermediate Similarity	NPC2949
0.7056	Intermediate Similarity	NPC472323
0.705	Intermediate Similarity	NPC304203
0.7037	Intermediate Similarity	NPC476817
0.7035	Intermediate Similarity	NPC472097
0.7033	Intermediate Similarity	NPC33421
0.7033	Intermediate Similarity	NPC206592
0.7031	Intermediate Similarity	NPC280852
0.7028	Intermediate Similarity	NPC470732
0.702	Intermediate Similarity	NPC473666
0.701	Intermediate Similarity	NPC286994
0.7005	Intermediate Similarity	NPC94752
0.6995	Remote Similarity	NPC34837
0.699	Remote Similarity	NPC228835
0.699	Remote Similarity	NPC317701
0.699	Remote Similarity	NPC21429
0.6989	Remote Similarity	NPC293487
0.6989	Remote Similarity	NPC65408
0.6974	Remote Similarity	NPC113626
0.697	Remote Similarity	NPC17059
0.6968	Remote Similarity	NPC478184
0.6966	Remote Similarity	NPC238499
0.6961	Remote Similarity	NPC153123
0.6961	Remote Similarity	NPC469740
0.6961	Remote Similarity	NPC201266
0.6961	Remote Similarity	NPC475914
0.6961	Remote Similarity	NPC220797
0.6961	Remote Similarity	NPC478186
0.6961	Remote Similarity	NPC474318
0.6961	Remote Similarity	NPC268744
0.6959	Remote Similarity	NPC11126
0.6957	Remote Similarity	NPC281094
0.695	Remote Similarity	NPC476460
0.6939	Remote Similarity	NPC159125
0.6935	Remote Similarity	NPC216643
0.6931	Remote Similarity	NPC57994
0.6931	Remote Similarity	NPC289299
0.6927	Remote Similarity	NPC77241
0.6927	Remote Similarity	NPC242269
0.6927	Remote Similarity	NPC13456
0.6927	Remote Similarity	NPC269203
0.6927	Remote Similarity	NPC166209
0.6923	Remote Similarity	NPC21605
0.6907	Remote Similarity	NPC14325
0.6907	Remote Similarity	NPC28848
0.6907	Remote Similarity	NPC237188
0.6904	Remote Similarity	NPC467063
0.69	Remote Similarity	NPC324091
0.69	Remote Similarity	NPC329858
0.69	Remote Similarity	NPC472112
0.6897	Remote Similarity	NPC472116
0.6897	Remote Similarity	NPC245916
0.6895	Remote Similarity	NPC114637
0.6895	Remote Similarity	NPC475338
0.6895	Remote Similarity	NPC478183
0.6895	Remote Similarity	NPC909
0.6893	Remote Similarity	NPC314102
0.6893	Remote Similarity	NPC251722
0.6891	Remote Similarity	NPC469938
0.6884	Remote Similarity	NPC473310
0.6882	Remote Similarity	NPC51054
0.6878	Remote Similarity	NPC470730
0.6878	Remote Similarity	NPC477175
0.6875	Remote Similarity	NPC471123
0.6875	Remote Similarity	NPC126492
0.6875	Remote Similarity	NPC201634
0.6872	Remote Similarity	NPC59084
0.6864	Remote Similarity	NPC476491
0.6864	Remote Similarity	NPC475258
0.686	Remote Similarity	NPC162730
0.6854	Remote Similarity	NPC473757
0.685	Remote Similarity	NPC196251
0.685	Remote Similarity	NPC175474
0.685	Remote Similarity	NPC111602
0.685	Remote Similarity	NPC63199
0.685	Remote Similarity	NPC102338
0.685	Remote Similarity	NPC213629
0.6847	Remote Similarity	NPC475859
0.6847	Remote Similarity	NPC475969
0.6845	Remote Similarity	NPC104345
0.6845	Remote Similarity	NPC129721
0.6842	Remote Similarity	NPC2165
0.6842	Remote Similarity	NPC195507
0.6835	Remote Similarity	NPC155444
0.6833	Remote Similarity	NPC473868
0.6833	Remote Similarity	NPC63157
0.6832	Remote Similarity	NPC472113
0.6829	Remote Similarity	NPC52557
0.6828	Remote Similarity	NPC476219
0.6825	Remote Similarity	NPC478158
0.6825	Remote Similarity	NPC478185
0.6823	Remote Similarity	NPC91895
0.6822	Remote Similarity	NPC478157
0.6821	Remote Similarity	NPC157583
0.6818	Remote Similarity	NPC477003
0.6816	Remote Similarity	NPC88097
0.6816	Remote Similarity	NPC165743
0.6816	Remote Similarity	NPC314333
0.6814	Remote Similarity	NPC128244
0.6812	Remote Similarity	NPC300183
0.681	Remote Similarity	NPC166492
0.681	Remote Similarity	NPC473362
0.6809	Remote Similarity	NPC6436
0.6809	Remote Similarity	NPC41257
0.6809	Remote Similarity	NPC56765
0.6808	Remote Similarity	NPC75634
0.6804	Remote Similarity	NPC469529
0.6791	Remote Similarity	NPC472027
0.6779	Remote Similarity	NPC474116
0.6768	Remote Similarity	NPC117027
0.6768	Remote Similarity	NPC472104
0.6766	Remote Similarity	NPC321708
0.6763	Remote Similarity	NPC252338
0.6757	Remote Similarity	NPC53947
0.6757	Remote Similarity	NPC66936
0.6755	Remote Similarity	NPC222029
0.6753	Remote Similarity	NPC473743
0.6749	Remote Similarity	NPC47190
0.6749	Remote Similarity	NPC272458
0.6736	Remote Similarity	NPC32534
0.6736	Remote Similarity	NPC471943
0.6735	Remote Similarity	NPC326575
0.6735	Remote Similarity	NPC284775
0.6721	Remote Similarity	NPC469525
0.672	Remote Similarity	NPC276085
0.672	Remote Similarity	NPC470233
0.6716	Remote Similarity	NPC473178
0.6714	Remote Similarity	NPC473376
0.671	Remote Similarity	NPC469734
0.6704	Remote Similarity	NPC150259
0.6701	Remote Similarity	NPC213468
0.6701	Remote Similarity	NPC6982
0.6701	Remote Similarity	NPC133261
0.6699	Remote Similarity	NPC232130
0.6699	Remote Similarity	NPC162440

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 NPC471386 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	565
0.2-0.3	1099
0.3-0.4	2205
0.4-0.5	2371
0.5-0.6	1930
0.6-0.7	637
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
0.7709	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7564	Discontinued
0.7462	Intermediate Similarity	NPD6664	Approved
0.7449	Intermediate Similarity	NPD7619	Phase 3
0.7449	Intermediate Similarity	NPD7618	Phase 3
0.7438	Intermediate Similarity	NPD7666	Phase 3
0.7438	Intermediate Similarity	NPD7665	Phase 2
0.7412	Intermediate Similarity	NPD3385	Approved
0.732	Intermediate Similarity	NPD6507	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD6999	Discontinued
0.7273	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5809	Phase 3
0.7188	Intermediate Similarity	NPD5473	Discontinued
0.7186	Intermediate Similarity	NPD7944	Discontinued
0.7179	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7789	Approved
0.7169	Intermediate Similarity	NPD7790	Approved
0.7169	Intermediate Similarity	NPD7953	Approved
0.7169	Intermediate Similarity	NPD7951	Approved
0.7169	Intermediate Similarity	NPD7952	Approved
0.7169	Intermediate Similarity	NPD7791	Approved
0.7169	Intermediate Similarity	NPD7950	Approved
0.715	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7394	Phase 2
0.7136	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4075	Phase 2
0.7111	Intermediate Similarity	NPD4547	Phase 3
0.7076	Intermediate Similarity	NPD3654	Approved
0.7064	Intermediate Similarity	NPD7781	Approved
0.7064	Intermediate Similarity	NPD7780	Approved
0.7059	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7454	Approved
0.7048	Intermediate Similarity	NPD7455	Approved
0.7035	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7824	Approved
0.7031	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4326	Phase 2
0.7026	Intermediate Similarity	NPD3318	Approved
0.7026	Intermediate Similarity	NPD3319	Phase 1
0.7026	Intermediate Similarity	NPD3320	Approved
0.7021	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6771	Discontinued
0.6995	Remote Similarity	NPD8401	Approved
0.6995	Remote Similarity	NPD8402	Approved
0.6995	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8400	Approved
0.6989	Remote Similarity	NPD200	Phase 2
0.6989	Remote Similarity	NPD45	Approved
0.6989	Remote Similarity	NPD6554	Approved
0.6989	Remote Similarity	NPD201	Phase 2
0.6971	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3323	Discontinued
0.6957	Remote Similarity	NPD8115	Approved
0.6957	Remote Similarity	NPD5426	Phase 3
0.6957	Remote Similarity	NPD8114	Approved
0.6951	Remote Similarity	NPD6986	Phase 1
0.695	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2880	Discontinued
0.6941	Remote Similarity	NPD7730	Approved
0.6941	Remote Similarity	NPD7731	Approved
0.6931	Remote Similarity	NPD5904	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4602	Approved
0.6927	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6217	Discontinued
0.6919	Remote Similarity	NPD6285	Phase 2
0.6915	Remote Similarity	NPD5315	Discontinued
0.6915	Remote Similarity	NPD5400	Approved
0.6912	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7482	Phase 2
0.6904	Remote Similarity	NPD7483	Phase 2
0.6897	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7308	Discontinued
0.6878	Remote Similarity	NPD3583	Phase 2
0.6875	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3077	Approved
0.6872	Remote Similarity	NPD3079	Approved
0.6872	Remote Similarity	NPD3076	Approved
0.6872	Remote Similarity	NPD3078	Approved
0.6868	Remote Similarity	NPD7469	Discontinued
0.6868	Remote Similarity	NPD1683	Approved
0.686	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6044	Discontinued
0.6856	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD5104	Approved
0.6854	Remote Similarity	NPD8094	Discontinued
0.6849	Remote Similarity	NPD7271	Approved
0.6847	Remote Similarity	NPD7406	Phase 2
0.6842	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5505	Discontinued
0.6818	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4499	Approved
0.6808	Remote Similarity	NPD8093	Discontinued
0.6792	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8016	Phase 3
0.6784	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7434	Approved
0.6777	Remote Similarity	NPD2442	Approved
0.6777	Remote Similarity	NPD2443	Approved
0.6774	Remote Similarity	NPD2837	Discontinued
0.6771	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7001	Phase 3
0.6751	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD4922	Phase 2
0.6742	Remote Similarity	NPD1254	Approved
0.6742	Remote Similarity	NPD1253	Approved
0.6742	Remote Similarity	NPD1255	Approved
0.6742	Remote Similarity	NPD1256	Approved
0.6733	Remote Similarity	NPD6281	Approved
0.6731	Remote Similarity	NPD5017	Discontinued
0.673	Remote Similarity	NPD3905	Phase 3
0.6729	Remote Similarity	NPD4852	Phase 2
0.6719	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6446	Discontinued
0.6717	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3961	Discontinued
0.6706	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD2916	Discontinued
0.6698	Remote Similarity	NPD6787	Phase 2
0.6684	Remote Similarity	NPD4640	Approved
0.6684	Remote Similarity	NPD4639	Approved
0.6684	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4638	Approved
0.6683	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5464	Approved
0.6683	Remote Similarity	NPD7175	Phase 1
0.6683	Remote Similarity	NPD7233	Approved
0.6683	Remote Similarity	NPD7234	Approved
0.6683	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4600	Approved
0.6683	Remote Similarity	NPD4601	Approved
0.6682	Remote Similarity	NPD7470	Discontinued
0.6682	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4397	Phase 1
0.6667	Remote Similarity	NPD8630	Approved
0.6667	Remote Similarity	NPD3431	Approved
0.6667	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD750	Phase 2
0.6667	Remote Similarity	NPD3430	Approved
0.6667	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2915	Discontinued
0.6667	Remote Similarity	NPD5254	Discontinued
0.6667	Remote Similarity	NPD7026	Phase 2
0.6652	Remote Similarity	NPD7716	Approved
0.6652	Remote Similarity	NPD7717	Approved
0.6651	Remote Similarity	NPD8322	Phase 2
0.6651	Remote Similarity	NPD6470	Phase 3
0.6651	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6178	Phase 3
0.665	Remote Similarity	NPD4181	Approved
0.665	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4848	Phase 1
0.665	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7111	Discontinued
0.6648	Remote Similarity	NPD3476	Approved
0.6648	Remote Similarity	NPD3475	Approved
0.6637	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7209	Approved
0.6635	Remote Similarity	NPD7208	Approved
0.6635	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7207	Approved
0.6631	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD6158	Phase 2
0.662	Remote Similarity	NPD6521	Phase 3
0.662	Remote Similarity	NPD6520	Phase 3
0.6619	Remote Similarity	NPD2881	Approved
0.6619	Remote Similarity	NPD2879	Approved
0.6617	Remote Similarity	NPD5075	Discontinued
0.6617	Remote Similarity	NPD5555	Phase 1
0.6615	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD2150	Discontinued
0.6613	Remote Similarity	NPD2430	Phase 2
0.6612	Remote Similarity	NPD2006	Phase 2
0.6612	Remote Similarity	NPD4047	Discontinued
0.6606	Remote Similarity	NPD6995	Phase 1
0.6604	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4500	Approved
0.6603	Remote Similarity	NPD4501	Approved
0.6598	Remote Similarity	NPD5021	Discontinued
0.6593	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD2408	Discontinued
0.6585	Remote Similarity	NPD7098	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