NPASS Compound

Structure

NPC471822 OpenBabel07101718312D 39 43 0 0 1 0 0 0 0 0999 V2000 -3.6750 0.4785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3785 -2.8313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5146 1.4652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0262 0.6193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8779 1.8665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1520 1.2129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4008 2.2691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1255 -0.5905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0204 -1.5459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0490 -1.4438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0268 -1.1764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6784 2.1992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3732 -0.4505 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3340 -2.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4177 -0.6536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 1.4652 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9822 -0.9733 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6918 0.9768 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 2.5259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9768 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.2841 -0.0443 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5378 2.4420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5378 1.4652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0810 0.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 1.4652 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8459 -0.4884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9876 -3.3541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.5027 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 2.9304 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3837 2.9304 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6358 -1.6992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6784 2.1992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0100 0.6093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 8 31 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 31 1 0 0 0 0 13 32 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 24 1 0 0 0 0 16 30 1 0 0 0 0 17 1 1 1 0 0 0 17 19 1 0 0 0 0 18 33 2 0 0 0 0 18 37 1 0 0 0 0 19 20 2 0 0 0 0 20 31 1 0 0 0 0 21 15 1 6 0 0 0 21 25 1 0 0 0 0 21 38 1 0 0 0 0 22 14 1 6 0 0 0 22 37 1 0 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 34 2 0 0 0 0 24 38 1 0 0 0 0 25 30 1 0 0 0 0 25 32 1 0 0 0 0 26 22 1 1 0 0 0 26 29 1 0 0 0 0 26 39 1 0 0 0 0 27 28 1 0 0 0 0 27 35 2 0 0 0 0 27 36 1 0 0 0 0 29 39 1 0 0 0 0 30 7 1 6 0 0 0 31 32 1 1 0 0 0 32 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.34
Volume:	570.231
LogP:	5.745
LogD:	4.013
LogS:	-4.899
# Rotatable Bonds:	8
TPSA:	102.43
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.235
Synthetic Accessibility Score:	5.482
Fsp3:	0.844
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.346
MDCK Permeability:	2.16359749174444e-05
Pgp-inhibitor:	0.94
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.072
30% Bioavailability (F30%):	0.848

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	92.0037612915039%
Volume Distribution (VD):	0.716
Pgp-substrate:	4.329206943511963%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.14
CYP2C9-substrate:	0.094
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.346
CYP3A4-substrate:	0.887

ADMET: Excretion

Clearance (CL):	1.675
Half-life (T1/2):	0.081

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.323
Drug-inuced Liver Injury (DILI):	0.745
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.559
Maximum Recommended Daily Dose:	0.696
Skin Sensitization:	0.074
Carcinogencity:	0.194
Eye Corrosion:	0.009
Eye Irritation:	0.018
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC471822

Natural Product ID:	NPC471822
*Common Name:**	GRDNOWYVDAPYNQ-HEIYMKIISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GRDNOWYVDAPYNQ-HEIYMKIISA-N
Standard InCHI:	InChI=1S/C32H48O7/c1-17(14-22(37-18(2)33)26-29(5,6)39-26)19-10-12-31(8)20(19)15-21-25-30(7,16-24(34)38-21)23(11-13-32(25,31)9)28(3,4)27(35)36/h17,21-23,25-26H,10-16H2,1-9H3,(H,35,36)/t17-,21+,22+,23?,25?,26-,30+,31+,32+/m1/s1
SMILES:	CC(CC(C1C(O1)(C)C)OC(=O)C)C2=C3CC4C5C(C3(CC2)C)(CCC(C5(CC(=O)O4)C)C(C)(C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL323538
PubChem CID:	44335289
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Others	5

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	10.3	%	PMID[528195]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	23.2	%	PMID[528195]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	38.2	%	PMID[528195]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	65.6	%	PMID[528195]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	90.7	%	PMID[528195]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	16000.0	nM	PMID[528195]

☑ 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 NPC471822 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	243
0.1-0.2	1596
0.2-0.3	5257
0.3-0.4	13566
0.4-0.5	8586
0.5-0.6	6123
0.6-0.7	5559
0.7-0.8	1717
0.8-0.85	29
0.85-0.9	3
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9663	High Similarity	NPC469315
0.9362	High Similarity	NPC469327
0.9348	High Similarity	NPC471777
0.9341	High Similarity	NPC240617
0.9032	High Similarity	NPC469329
0.9032	High Similarity	NPC473415
0.9032	High Similarity	NPC30677
0.9032	High Similarity	NPC180557
0.9032	High Similarity	NPC37787
0.8889	High Similarity	NPC9457
0.8889	High Similarity	NPC471783
0.8866	High Similarity	NPC469316
0.8817	High Similarity	NPC274046
0.8817	High Similarity	NPC198074
0.8788	High Similarity	NPC470587
0.871	High Similarity	NPC473166
0.8586	High Similarity	NPC324001
0.8529	High Similarity	NPC41405
0.828	Intermediate Similarity	NPC469317
0.828	Intermediate Similarity	NPC241875
0.828	Intermediate Similarity	NPC469314
0.828	Intermediate Similarity	NPC469322
0.8269	Intermediate Similarity	NPC5284
0.8218	Intermediate Similarity	NPC264048
0.8211	Intermediate Similarity	NPC20388
0.8211	Intermediate Similarity	NPC471896
0.8208	Intermediate Similarity	NPC255017
0.8182	Intermediate Similarity	NPC471582
0.8182	Intermediate Similarity	NPC303777
0.8182	Intermediate Similarity	NPC471784
0.8173	Intermediate Similarity	NPC218853
0.8163	Intermediate Similarity	NPC327788
0.8155	Intermediate Similarity	NPC473165
0.8155	Intermediate Similarity	NPC469318
0.8155	Intermediate Similarity	NPC473173
0.8144	Intermediate Similarity	NPC159410
0.8137	Intermediate Similarity	NPC471293
0.8125	Intermediate Similarity	NPC26888
0.8119	Intermediate Similarity	NPC473163
0.8113	Intermediate Similarity	NPC152117
0.8113	Intermediate Similarity	NPC234042
0.8105	Intermediate Similarity	NPC474889
0.8095	Intermediate Similarity	NPC250956
0.8061	Intermediate Similarity	NPC279974
0.8061	Intermediate Similarity	NPC473170
0.8058	Intermediate Similarity	NPC472655
0.8041	Intermediate Similarity	NPC477435
0.8041	Intermediate Similarity	NPC79117
0.8041	Intermediate Similarity	NPC477436
0.8021	Intermediate Similarity	NPC111585
0.8021	Intermediate Similarity	NPC148414
0.8021	Intermediate Similarity	NPC175628
0.802	Intermediate Similarity	NPC476897
0.8	Intermediate Similarity	NPC161065
0.8	Intermediate Similarity	NPC119036
0.8	Intermediate Similarity	NPC470068
0.8	Intermediate Similarity	NPC475876
0.798	Intermediate Similarity	NPC120708
0.798	Intermediate Similarity	NPC471039
0.7979	Intermediate Similarity	NPC325594
0.7979	Intermediate Similarity	NPC73038
0.7963	Intermediate Similarity	NPC284915
0.7961	Intermediate Similarity	NPC65523
0.7959	Intermediate Similarity	NPC296164
0.7959	Intermediate Similarity	NPC471040
0.7959	Intermediate Similarity	NPC477439
0.7941	Intermediate Similarity	NPC475558
0.7941	Intermediate Similarity	NPC473788
0.7941	Intermediate Similarity	NPC296879
0.7941	Intermediate Similarity	NPC473928
0.7941	Intermediate Similarity	NPC471119
0.7938	Intermediate Similarity	NPC285184
0.7938	Intermediate Similarity	NPC470590
0.7938	Intermediate Similarity	NPC77099
0.7938	Intermediate Similarity	NPC60755
0.7928	Intermediate Similarity	NPC241192
0.7925	Intermediate Similarity	NPC472214
0.7925	Intermediate Similarity	NPC472215
0.7917	Intermediate Similarity	NPC475921
0.7917	Intermediate Similarity	NPC474704
0.7917	Intermediate Similarity	NPC471342
0.7917	Intermediate Similarity	NPC30522
0.7917	Intermediate Similarity	NPC469866
0.79	Intermediate Similarity	NPC158347
0.789	Intermediate Similarity	NPC298278
0.789	Intermediate Similarity	NPC270929
0.7885	Intermediate Similarity	NPC475414
0.7885	Intermediate Similarity	NPC173172
0.7879	Intermediate Similarity	NPC473648
0.7879	Intermediate Similarity	NPC317586
0.7879	Intermediate Similarity	NPC477437
0.7879	Intermediate Similarity	NPC470016
0.7879	Intermediate Similarity	NPC477438
0.7879	Intermediate Similarity	NPC195715
0.7864	Intermediate Similarity	NPC218513
0.7864	Intermediate Similarity	NPC55954
0.7857	Intermediate Similarity	NPC86368
0.7857	Intermediate Similarity	NPC141497
0.7857	Intermediate Similarity	NPC170220
0.7857	Intermediate Similarity	NPC107674
0.785	Intermediate Similarity	NPC474846
0.785	Intermediate Similarity	NPC469655
0.785	Intermediate Similarity	NPC469656
0.7849	Intermediate Similarity	NPC86370
0.7843	Intermediate Similarity	NPC470054
0.7843	Intermediate Similarity	NPC233012
0.7843	Intermediate Similarity	NPC54909
0.7835	Intermediate Similarity	NPC473269
0.7835	Intermediate Similarity	NPC474728
0.7835	Intermediate Similarity	NPC113989
0.7835	Intermediate Similarity	NPC120840
0.783	Intermediate Similarity	NPC472216
0.783	Intermediate Similarity	NPC5475
0.783	Intermediate Similarity	NPC284828
0.783	Intermediate Similarity	NPC173905
0.783	Intermediate Similarity	NPC477069
0.783	Intermediate Similarity	NPC477070
0.7822	Intermediate Similarity	NPC472028
0.7822	Intermediate Similarity	NPC260149
0.7822	Intermediate Similarity	NPC470067
0.7822	Intermediate Similarity	NPC470066
0.7822	Intermediate Similarity	NPC477854
0.7822	Intermediate Similarity	NPC58942
0.7812	Intermediate Similarity	NPC255176
0.7812	Intermediate Similarity	NPC242864
0.7812	Intermediate Similarity	NPC4309
0.781	Intermediate Similarity	NPC59530
0.781	Intermediate Similarity	NPC475176
0.78	Intermediate Similarity	NPC327179
0.78	Intermediate Similarity	NPC230151
0.7798	Intermediate Similarity	NPC472274
0.7788	Intermediate Similarity	NPC75531
0.7788	Intermediate Similarity	NPC473175
0.7788	Intermediate Similarity	NPC149124
0.7778	Intermediate Similarity	NPC23621
0.7778	Intermediate Similarity	NPC280782
0.7778	Intermediate Similarity	NPC67831
0.7778	Intermediate Similarity	NPC174051
0.7778	Intermediate Similarity	NPC184006
0.7778	Intermediate Similarity	NPC470063
0.7778	Intermediate Similarity	NPC476163
0.7778	Intermediate Similarity	NPC78580
0.7778	Intermediate Similarity	NPC166906
0.7767	Intermediate Similarity	NPC470053
0.7757	Intermediate Similarity	NPC470065
0.7757	Intermediate Similarity	NPC239097
0.7755	Intermediate Similarity	NPC86266
0.7755	Intermediate Similarity	NPC262870
0.7755	Intermediate Similarity	NPC110657
0.7755	Intermediate Similarity	NPC235704
0.7755	Intermediate Similarity	NPC471901
0.7755	Intermediate Similarity	NPC189520
0.7755	Intermediate Similarity	NPC473167
0.7755	Intermediate Similarity	NPC212301
0.7748	Intermediate Similarity	NPC329736
0.7745	Intermediate Similarity	NPC167974
0.7745	Intermediate Similarity	NPC316964
0.7745	Intermediate Similarity	NPC473176
0.7745	Intermediate Similarity	NPC83709
0.7745	Intermediate Similarity	NPC94906
0.7745	Intermediate Similarity	NPC471041
0.7736	Intermediate Similarity	NPC472218
0.7736	Intermediate Similarity	NPC318363
0.7736	Intermediate Similarity	NPC472219
0.7736	Intermediate Similarity	NPC473482
0.7736	Intermediate Similarity	NPC472217
0.7736	Intermediate Similarity	NPC94942
0.7736	Intermediate Similarity	NPC258323
0.7736	Intermediate Similarity	NPC475418
0.7736	Intermediate Similarity	NPC153587
0.7732	Intermediate Similarity	NPC128496
0.7732	Intermediate Similarity	NPC469319
0.7732	Intermediate Similarity	NPC469323
0.7732	Intermediate Similarity	NPC229871
0.7727	Intermediate Similarity	NPC302471
0.7727	Intermediate Similarity	NPC243981
0.7723	Intermediate Similarity	NPC473456
0.7723	Intermediate Similarity	NPC292133
0.7723	Intermediate Similarity	NPC470425
0.7714	Intermediate Similarity	NPC278628
0.7714	Intermediate Similarity	NPC231530
0.7714	Intermediate Similarity	NPC475494
0.7708	Intermediate Similarity	NPC474684
0.7708	Intermediate Similarity	NPC142361
0.77	Intermediate Similarity	NPC23241
0.77	Intermediate Similarity	NPC84383
0.77	Intermediate Similarity	NPC184848
0.77	Intermediate Similarity	NPC469599
0.77	Intermediate Similarity	NPC69548
0.77	Intermediate Similarity	NPC470031
0.77	Intermediate Similarity	NPC134067
0.77	Intermediate Similarity	NPC48330
0.7692	Intermediate Similarity	NPC222153
0.7692	Intermediate Similarity	NPC470310
0.7692	Intermediate Similarity	NPC180204
0.7692	Intermediate Similarity	NPC471005
0.7685	Intermediate Similarity	NPC474229
0.7685	Intermediate Similarity	NPC477073
0.7679	Intermediate Similarity	NPC42673
0.7679	Intermediate Similarity	NPC61520

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 NPC471822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1977
0.2-0.3	3908
0.3-0.4	2040
0.4-0.5	581
0.5-0.6	219
0.6-0.7	191
0.7-0.8	27
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
0.7778	Intermediate Similarity	NPD8297	Approved
0.7714	Intermediate Similarity	NPD7128	Approved
0.7714	Intermediate Similarity	NPD5739	Approved
0.7714	Intermediate Similarity	NPD6675	Approved
0.7714	Intermediate Similarity	NPD6402	Approved
0.7677	Intermediate Similarity	NPD6399	Phase 3
0.76	Intermediate Similarity	NPD7748	Approved
0.7576	Intermediate Similarity	NPD8034	Phase 2
0.7576	Intermediate Similarity	NPD8035	Phase 2
0.757	Intermediate Similarity	NPD6881	Approved
0.757	Intermediate Similarity	NPD6899	Approved
0.757	Intermediate Similarity	NPD7320	Approved
0.7523	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6372	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.7477	Intermediate Similarity	NPD5701	Approved
0.7477	Intermediate Similarity	NPD5697	Approved
0.7431	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6883	Approved
0.7431	Intermediate Similarity	NPD7290	Approved
0.7431	Intermediate Similarity	NPD7102	Approved
0.74	Intermediate Similarity	NPD6411	Approved
0.7383	Intermediate Similarity	NPD6008	Approved
0.7379	Intermediate Similarity	NPD7902	Approved
0.7374	Intermediate Similarity	NPD5328	Approved
0.7364	Intermediate Similarity	NPD6649	Approved
0.7364	Intermediate Similarity	NPD6847	Approved
0.7364	Intermediate Similarity	NPD6617	Approved
0.7364	Intermediate Similarity	NPD6650	Approved
0.7364	Intermediate Similarity	NPD6869	Approved
0.7345	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD6013	Approved
0.7339	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6012	Approved
0.732	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6882	Approved
0.7248	Intermediate Similarity	NPD6011	Approved
0.7228	Intermediate Similarity	NPD7515	Phase 2
0.7228	Intermediate Similarity	NPD6079	Approved
0.7216	Intermediate Similarity	NPD4786	Approved
0.7212	Intermediate Similarity	NPD6083	Phase 2
0.7212	Intermediate Similarity	NPD6084	Phase 2
0.7212	Intermediate Similarity	NPD4755	Approved
0.7207	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6101	Approved
0.72	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3667	Approved
0.7172	Intermediate Similarity	NPD3573	Approved
0.7156	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7638	Approved
0.7097	Intermediate Similarity	NPD6117	Approved
0.7091	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7900	Approved
0.7087	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4632	Approved
0.7075	Intermediate Similarity	NPD7639	Approved
0.7075	Intermediate Similarity	NPD4700	Approved
0.7075	Intermediate Similarity	NPD5286	Approved
0.7075	Intermediate Similarity	NPD4696	Approved
0.7075	Intermediate Similarity	NPD5285	Approved
0.7075	Intermediate Similarity	NPD7640	Approved
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD3618	Phase 1
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7071	Intermediate Similarity	NPD7521	Approved
0.7021	Intermediate Similarity	NPD6116	Phase 1
0.7019	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5695	Phase 3
0.7009	Intermediate Similarity	NPD6319	Approved
0.7	Intermediate Similarity	NPD7507	Approved
0.6989	Remote Similarity	NPD3702	Approved
0.6981	Remote Similarity	NPD5696	Approved
0.6981	Remote Similarity	NPD4225	Approved
0.6975	Remote Similarity	NPD7604	Phase 2
0.6957	Remote Similarity	NPD6274	Approved
0.6952	Remote Similarity	NPD5221	Approved
0.6952	Remote Similarity	NPD4697	Phase 3
0.6952	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5222	Approved
0.6947	Remote Similarity	NPD6115	Approved
0.6947	Remote Similarity	NPD6114	Approved
0.6947	Remote Similarity	NPD6697	Approved
0.6947	Remote Similarity	NPD6118	Approved
0.6944	Remote Similarity	NPD5226	Approved
0.6944	Remote Similarity	NPD5225	Approved
0.6944	Remote Similarity	NPD4633	Approved
0.6944	Remote Similarity	NPD5211	Phase 2
0.6944	Remote Similarity	NPD7632	Discontinued
0.6944	Remote Similarity	NPD5224	Approved
0.6942	Remote Similarity	NPD8293	Discontinued
0.6931	Remote Similarity	NPD6672	Approved
0.6931	Remote Similarity	NPD6903	Approved
0.6931	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5737	Approved
0.6923	Remote Similarity	NPD7101	Approved
0.6923	Remote Similarity	NPD7100	Approved
0.6917	Remote Similarity	NPD7492	Approved
0.6897	Remote Similarity	NPD6009	Approved
0.6887	Remote Similarity	NPD5173	Approved
0.6885	Remote Similarity	NPD7736	Approved
0.6882	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5175	Approved
0.6881	Remote Similarity	NPD5174	Approved
0.6869	Remote Similarity	NPD3668	Phase 3
0.6864	Remote Similarity	NPD6054	Approved
0.6864	Remote Similarity	NPD6059	Approved
0.686	Remote Similarity	NPD6616	Approved
0.6852	Remote Similarity	NPD5223	Approved
0.6847	Remote Similarity	NPD6412	Phase 2
0.6838	Remote Similarity	NPD6335	Approved
0.6833	Remote Similarity	NPD8328	Phase 3
0.6829	Remote Similarity	NPD7319	Approved
0.6827	Remote Similarity	NPD4202	Approved
0.6818	Remote Similarity	NPD5141	Approved
0.681	Remote Similarity	NPD6868	Approved
0.6807	Remote Similarity	NPD5983	Phase 2
0.6807	Remote Similarity	NPD6908	Approved
0.6807	Remote Similarity	NPD6909	Approved
0.6804	Remote Similarity	NPD7525	Registered
0.6803	Remote Similarity	NPD7078	Approved
0.6786	Remote Similarity	NPD6686	Approved
0.6783	Remote Similarity	NPD8133	Approved
0.6757	Remote Similarity	NPD4768	Approved
0.6757	Remote Similarity	NPD4767	Approved
0.6752	Remote Similarity	NPD6317	Approved
0.675	Remote Similarity	NPD6370	Approved
0.6733	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6098	Approved
0.6727	Remote Similarity	NPD4754	Approved
0.6721	Remote Similarity	NPD6336	Discontinued
0.67	Remote Similarity	NPD3666	Approved
0.67	Remote Similarity	NPD3665	Phase 1
0.67	Remote Similarity	NPD3133	Approved
0.6699	Remote Similarity	NPD6673	Approved
0.6699	Remote Similarity	NPD6080	Approved
0.6699	Remote Similarity	NPD6904	Approved
0.6699	Remote Similarity	NPD4753	Phase 2
0.6695	Remote Similarity	NPD6313	Approved
0.6695	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6637	Remote Similarity	NPD5128	Approved
0.6637	Remote Similarity	NPD4729	Approved
0.6637	Remote Similarity	NPD4730	Approved
0.6632	Remote Similarity	NPD3703	Phase 2
0.6612	Remote Similarity	NPD5988	Approved
0.6604	Remote Similarity	NPD6001	Approved
0.6598	Remote Similarity	NPD3617	Approved
0.6545	Remote Similarity	NPD4159	Approved
0.6538	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7645	Phase 2
0.6529	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD8033	Approved
0.6522	Remote Similarity	NPD5247	Approved
0.6522	Remote Similarity	NPD5249	Phase 3
0.6522	Remote Similarity	NPD5248	Approved
0.6522	Remote Similarity	NPD5250	Approved
0.6522	Remote Similarity	NPD5251	Approved
0.65	Remote Similarity	NPD6435	Approved
0.65	Remote Similarity	NPD4221	Approved
0.65	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4223	Phase 3
0.6489	Remote Similarity	NPD5777	Approved
0.6489	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6698	Approved
0.6476	Remote Similarity	NPD46	Approved
0.6471	Remote Similarity	NPD5329	Approved
0.6466	Remote Similarity	NPD5215	Approved
0.6466	Remote Similarity	NPD5216	Approved
0.6466	Remote Similarity	NPD5217	Approved
0.6458	Remote Similarity	NPD7339	Approved
0.6458	Remote Similarity	NPD6942	Approved
0.6452	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD8377	Approved
0.6446	Remote Similarity	NPD8294	Approved
0.6442	Remote Similarity	NPD5208	Approved
0.6436	Remote Similarity	NPD4788	Approved
0.6436	Remote Similarity	NPD7154	Phase 3
0.6417	Remote Similarity	NPD7327	Approved
0.6417	Remote Similarity	NPD7328	Approved
0.6415	Remote Similarity	NPD6050	Approved
0.6415	Remote Similarity	NPD7637	Suspended
0.6415	Remote Similarity	NPD5693	Phase 1
0.6415	Remote Similarity	NPD5281	Approved
0.6415	Remote Similarity	NPD5284	Approved
0.641	Remote Similarity	NPD6053	Discontinued
0.6408	Remote Similarity	NPD6422	Discontinued
0.64	Remote Similarity	NPD4692	Approved
0.64	Remote Similarity	NPD4139	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