NPASS Compound

Structure

NPC235460 OpenBabel07101719512D 45 50 0 0 1 0 0 0 0 0999 V2000 4.1225 -3.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6384 -4.8955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4495 1.9544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0141 -2.1381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1131 -2.5719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1285 -2.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 -1.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0932 -0.7670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4923 -4.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0584 -3.3019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4895 -4.2776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6217 -2.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0528 -3.4514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -3.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -3.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3201 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -2.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -0.3765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4533 -2.4612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0149 -4.1137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4467 1.8797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6189 -2.5504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -0.5990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -2.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7568 -2.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3173 0.1525 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1906 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7512 -0.7485 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1823 -1.7242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1878 -1.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7484 -0.8232 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7624 -1.5102 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0261 -4.2627 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0100 2.7059 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1795 -1.7989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3802 -3.1828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8806 0.9787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 34 1 0 0 0 0 5 34 1 0 0 0 0 6 35 1 0 0 0 0 8 39 1 0 0 0 0 9 39 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 24 2 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 35 1 0 0 0 0 17 25 2 0 0 0 0 17 28 1 0 0 0 0 18 27 1 0 0 0 0 18 29 1 0 0 0 0 19 25 1 0 0 0 0 20 30 1 0 0 0 0 20 36 1 0 0 0 0 21 1 1 1 0 0 0 21 26 1 0 0 0 0 21 39 1 0 0 0 0 22 40 2 0 0 0 0 22 43 1 0 0 0 0 23 41 2 0 0 0 0 23 44 1 0 0 0 0 24 33 1 0 0 0 0 26 36 1 1 0 0 0 27 31 1 0 0 0 0 27 43 1 6 0 0 0 28 32 1 0 0 0 0 28 44 1 6 0 0 0 29 35 1 6 0 0 0 29 37 1 0 0 0 0 30 37 1 1 0 0 0 30 45 1 0 0 0 0 31 25 1 1 0 0 0 31 34 1 0 0 0 0 32 34 1 0 0 0 0 32 38 1 1 0 0 0 33 38 2 3 0 0 0 33 42 1 0 0 0 0 35 36 1 6 0 0 0 36 7 1 1 0 0 0 37 19 1 6 0 0 0 37 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	620.38
Volume:	653.449
LogP:	5.479
LogD:	4.002
LogS:	-5.087
# Rotatable Bonds:	9
TPSA:	97.47
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.253
Synthetic Accessibility Score:	5.861
Fsp3:	0.703
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:	-5.273
MDCK Permeability:	2.8019732781103812e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.949
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.917

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	58.07597351074219%
Volume Distribution (VD):	2.247
Pgp-substrate:	31.293764114379883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.787
CYP2C9-inhibitor:	0.345
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.476
CYP2D6-substrate:	0.325
CYP3A4-inhibitor:	0.842
CYP3A4-substrate:	0.852

ADMET: Excretion

Clearance (CL):	2.911
Half-life (T1/2):	0.166

ADMET: Toxicity

hERG Blockers:	0.797
Human Hepatotoxicity (H-HT):	0.461
Drug-inuced Liver Injury (DILI):	0.469
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.808
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.197
Carcinogencity:	0.051
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC235460

Natural Product ID:	NPC235460
*Common Name:**	QRARTDSIPPBUHA-LAQXXDHZSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-Buxapapillinine
Standard InCHIKey:	QRARTDSIPPBUHA-LAQXXDHZSA-N
Standard InCHI:	InChI=1S/C37H52N2O6/c1-21(39(8)9)26-15-16-35(6)29-18-27(43-22(2)40)31-25(19-37(29)30(45-37)20-36(26,35)7)17-28(44-23(3)41)32(34(31,4)5)38-33(42)24-13-11-10-12-14-24/h10-14,17,21,26-32H,15-16,18-20H2,1-9H3,(H,38,42)/t21-,26+,27-,28+,29-,30-,31-,32-,35-,36+,37+/m0/s1
SMILES:	C[C@@H]([C@H]1CC[C@@]2(C)[C@@H]3C[C@@H]([C@@H]4C(=C[C@H]([C@@H](C4(C)C)N=C(c4ccccc4)O)OC(=O)C)C[C@@]43[C@H](C[C@]12C)O4)OC(=O)C)N(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508669
PubChem CID:	21591143
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346940]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19205	Buxus sempervirens	Species	Buxaceae	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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT822	Organism	Lemna minor	Lemna minor	Activity	=	86.0	%	PMID[530017]
NPT822	Organism	Lemna minor	Lemna minor	Activity	=	71.0	%	PMID[530017]
NPT822	Organism	Lemna minor	Lemna minor	Activity	=	57.0	%	PMID[530017]

☑ 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 NPC235460 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	193
0.1-0.2	982
0.2-0.3	2168
0.3-0.4	6701
0.4-0.5	21352
0.5-0.6	10094
0.6-0.7	1168
0.7-0.8	33
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC217801
0.8827	High Similarity	NPC203005
0.8636	High Similarity	NPC275839
0.8487	Intermediate Similarity	NPC328824
0.8477	Intermediate Similarity	NPC473922
0.8377	Intermediate Similarity	NPC476757
0.8247	Intermediate Similarity	NPC475578
0.8129	Intermediate Similarity	NPC44649
0.8121	Intermediate Similarity	NPC3202
0.8065	Intermediate Similarity	NPC262216
0.7947	Intermediate Similarity	NPC90693
0.7947	Intermediate Similarity	NPC64897
0.7829	Intermediate Similarity	NPC132847
0.7692	Intermediate Similarity	NPC239770
0.764	Intermediate Similarity	NPC201692
0.7625	Intermediate Similarity	NPC173934
0.7576	Intermediate Similarity	NPC93343
0.7562	Intermediate Similarity	NPC31171
0.7562	Intermediate Similarity	NPC237240
0.75	Intermediate Similarity	NPC476750
0.7485	Intermediate Similarity	NPC476749
0.7421	Intermediate Similarity	NPC261709
0.7421	Intermediate Similarity	NPC111586
0.7421	Intermediate Similarity	NPC108852
0.7378	Intermediate Similarity	NPC470274
0.7337	Intermediate Similarity	NPC156348
0.7333	Intermediate Similarity	NPC109151
0.7256	Intermediate Similarity	NPC94602
0.7244	Intermediate Similarity	NPC42423
0.7209	Intermediate Similarity	NPC15506
0.7134	Intermediate Similarity	NPC246079
0.7126	Intermediate Similarity	NPC4108
0.712	Intermediate Similarity	NPC40539
0.7081	Intermediate Similarity	NPC163578
0.7081	Intermediate Similarity	NPC262324
0.7081	Intermediate Similarity	NPC153007
0.7081	Intermediate Similarity	NPC108276
0.7081	Intermediate Similarity	NPC243893
0.7078	Intermediate Similarity	NPC472414
0.7055	Intermediate Similarity	NPC475128
0.7051	Intermediate Similarity	NPC295478
0.7051	Intermediate Similarity	NPC71271
0.7043	Intermediate Similarity	NPC166521
0.7043	Intermediate Similarity	NPC124690
0.7043	Intermediate Similarity	NPC184195
0.7043	Intermediate Similarity	NPC172769
0.7043	Intermediate Similarity	NPC281470
0.7043	Intermediate Similarity	NPC205
0.7032	Intermediate Similarity	NPC278097
0.703	Intermediate Similarity	NPC260194
0.6994	Remote Similarity	NPC79921
0.6987	Remote Similarity	NPC5486
0.6961	Remote Similarity	NPC475345
0.6957	Remote Similarity	NPC478140
0.6957	Remote Similarity	NPC175870
0.6957	Remote Similarity	NPC471864
0.6937	Remote Similarity	NPC228511
0.6933	Remote Similarity	NPC470820
0.6923	Remote Similarity	NPC475649
0.6923	Remote Similarity	NPC472761
0.6919	Remote Similarity	NPC327699
0.6903	Remote Similarity	NPC307139
0.6903	Remote Similarity	NPC472373
0.6903	Remote Similarity	NPC77691
0.6894	Remote Similarity	NPC113325
0.6894	Remote Similarity	NPC279045
0.6886	Remote Similarity	NPC473541
0.6883	Remote Similarity	NPC160493
0.6872	Remote Similarity	NPC120667
0.6872	Remote Similarity	NPC278272
0.6867	Remote Similarity	NPC49565
0.6863	Remote Similarity	NPC472458
0.6859	Remote Similarity	NPC284022
0.6851	Remote Similarity	NPC476113
0.6839	Remote Similarity	NPC273336
0.6839	Remote Similarity	NPC12016
0.6839	Remote Similarity	NPC182333
0.6835	Remote Similarity	NPC58061
0.6835	Remote Similarity	NPC230331
0.6833	Remote Similarity	NPC88378
0.6833	Remote Similarity	NPC211713
0.6815	Remote Similarity	NPC45821
0.68	Remote Similarity	NPC473869
0.6797	Remote Similarity	NPC242692
0.6795	Remote Similarity	NPC470815
0.6792	Remote Similarity	NPC93632
0.679	Remote Similarity	NPC48929
0.6778	Remote Similarity	NPC474953
0.6778	Remote Similarity	NPC476751
0.6774	Remote Similarity	NPC473889
0.677	Remote Similarity	NPC313663
0.6755	Remote Similarity	NPC475336
0.6755	Remote Similarity	NPC453583
0.6755	Remote Similarity	NPC473300
0.6753	Remote Similarity	NPC190663
0.6752	Remote Similarity	NPC4974
0.6752	Remote Similarity	NPC471758
0.6748	Remote Similarity	NPC208725
0.674	Remote Similarity	NPC477115
0.6739	Remote Similarity	NPC475794
0.6731	Remote Similarity	NPC472415
0.6731	Remote Similarity	NPC473871
0.6731	Remote Similarity	NPC473870
0.6726	Remote Similarity	NPC471139
0.6725	Remote Similarity	NPC475561
0.6725	Remote Similarity	NPC475417
0.6725	Remote Similarity	NPC125033
0.672	Remote Similarity	NPC67246
0.672	Remote Similarity	NPC33372
0.6719	Remote Similarity	NPC473558
0.6719	Remote Similarity	NPC473490
0.6716	Remote Similarity	NPC140311
0.671	Remote Similarity	NPC476184
0.671	Remote Similarity	NPC476281
0.6709	Remote Similarity	NPC470816
0.6708	Remote Similarity	NPC246913
0.6707	Remote Similarity	NPC472372
0.6707	Remote Similarity	NPC472374
0.6707	Remote Similarity	NPC192658
0.6703	Remote Similarity	NPC305847
0.6702	Remote Similarity	NPC321072
0.6702	Remote Similarity	NPC242662
0.6702	Remote Similarity	NPC215892
0.6702	Remote Similarity	NPC191193
0.6688	Remote Similarity	NPC476241
0.6688	Remote Similarity	NPC476260
0.6687	Remote Similarity	NPC203486
0.6687	Remote Similarity	NPC162613
0.6687	Remote Similarity	NPC87934
0.6687	Remote Similarity	NPC469360
0.6686	Remote Similarity	NPC62792
0.6686	Remote Similarity	NPC313414
0.6686	Remote Similarity	NPC478123
0.6685	Remote Similarity	NPC475962
0.6667	Remote Similarity	NPC317882
0.6667	Remote Similarity	NPC191387
0.6667	Remote Similarity	NPC471606
0.6667	Remote Similarity	NPC207675
0.6667	Remote Similarity	NPC474650
0.6667	Remote Similarity	NPC253681
0.6667	Remote Similarity	NPC208553
0.6667	Remote Similarity	NPC199738
0.6667	Remote Similarity	NPC471754
0.6667	Remote Similarity	NPC302449
0.6667	Remote Similarity	NPC84129
0.6667	Remote Similarity	NPC210950
0.6667	Remote Similarity	NPC131966
0.6667	Remote Similarity	NPC181964
0.6667	Remote Similarity	NPC212699
0.665	Remote Similarity	NPC106593
0.6649	Remote Similarity	NPC471395
0.6649	Remote Similarity	NPC99179
0.6647	Remote Similarity	NPC312393
0.6647	Remote Similarity	NPC473602
0.6647	Remote Similarity	NPC266374
0.6646	Remote Similarity	NPC476125
0.6646	Remote Similarity	NPC476179
0.6646	Remote Similarity	NPC11266
0.6645	Remote Similarity	NPC476183
0.6629	Remote Similarity	NPC253738
0.6627	Remote Similarity	NPC34943
0.6627	Remote Similarity	NPC197921
0.6627	Remote Similarity	NPC9905
0.6624	Remote Similarity	NPC476278
0.6623	Remote Similarity	NPC473860
0.6623	Remote Similarity	NPC89324
0.6618	Remote Similarity	NPC473667
0.6616	Remote Similarity	NPC326895
0.6613	Remote Similarity	NPC474607
0.6607	Remote Similarity	NPC140021
0.6606	Remote Similarity	NPC472551
0.6606	Remote Similarity	NPC472545
0.6605	Remote Similarity	NPC72915
0.6604	Remote Similarity	NPC470158
0.6604	Remote Similarity	NPC476970
0.6604	Remote Similarity	NPC475933
0.6603	Remote Similarity	NPC300827
0.6603	Remote Similarity	NPC473439
0.6601	Remote Similarity	NPC472862
0.6593	Remote Similarity	NPC476227
0.6592	Remote Similarity	NPC278887
0.659	Remote Similarity	NPC253591
0.659	Remote Similarity	NPC298072
0.6588	Remote Similarity	NPC125882
0.6588	Remote Similarity	NPC96447
0.6587	Remote Similarity	NPC91953
0.6587	Remote Similarity	NPC116742
0.6587	Remote Similarity	NPC472547
0.6587	Remote Similarity	NPC139243
0.6583	Remote Similarity	NPC94687
0.6583	Remote Similarity	NPC476495
0.6583	Remote Similarity	NPC106840
0.6581	Remote Similarity	NPC470814
0.6579	Remote Similarity	NPC324251
0.6579	Remote Similarity	NPC275170
0.6579	Remote Similarity	NPC471629
0.6579	Remote Similarity	NPC206211
0.6579	Remote Similarity	NPC473400
0.6579	Remote Similarity	NPC165396
0.6579	Remote Similarity	NPC306001

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 NPC235460 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	125
0.1-0.2	467
0.2-0.3	820
0.3-0.4	2029
0.4-0.5	3693
0.5-0.6	1757
0.6-0.7	257
0.7-0.8	2
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
0.7562	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2174	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7741	Discontinued
0.6826	Remote Similarity	NPD3692	Discontinued
0.6816	Remote Similarity	NPD4481	Phase 3
0.6786	Remote Similarity	NPD6667	Approved
0.6786	Remote Similarity	NPD6666	Approved
0.677	Remote Similarity	NPD7714	Approved
0.677	Remote Similarity	NPD7715	Approved
0.6728	Remote Similarity	NPD6346	Approved
0.6727	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7315	Approved
0.6703	Remote Similarity	NPD7312	Approved
0.6703	Remote Similarity	NPD7311	Approved
0.6703	Remote Similarity	NPD7313	Approved
0.6703	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7310	Approved
0.6667	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2575	Approved
0.6667	Remote Similarity	NPD8485	Approved
0.6667	Remote Similarity	NPD1753	Discontinued
0.6667	Remote Similarity	NPD2969	Approved
0.6667	Remote Similarity	NPD2970	Approved
0.6667	Remote Similarity	NPD7309	Approved
0.6645	Remote Similarity	NPD7725	Approved
0.663	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2238	Phase 2
0.6606	Remote Similarity	NPD8148	Approved
0.6606	Remote Similarity	NPD8147	Approved
0.6605	Remote Similarity	NPD4621	Approved
0.6605	Remote Similarity	NPD4619	Approved
0.6599	Remote Similarity	NPD5704	Approved
0.6599	Remote Similarity	NPD5706	Approved
0.6599	Remote Similarity	NPD5705	Approved
0.6596	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6025	Phase 1
0.6578	Remote Similarity	NPD8407	Phase 2
0.6576	Remote Similarity	NPD5190	Phase 2
0.6571	Remote Similarity	NPD6072	Discontinued
0.6564	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD2570	Approved
0.6564	Remote Similarity	NPD2574	Discontinued
0.6564	Remote Similarity	NPD2571	Approved
0.6564	Remote Similarity	NPD3087	Approved
0.6564	Remote Similarity	NPD3614	Approved
0.6564	Remote Similarity	NPD2573	Approved
0.6564	Remote Similarity	NPD3616	Approved
0.6564	Remote Similarity	NPD3615	Approved
0.6564	Remote Similarity	NPD2566	Approved
0.6564	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD3089	Approved
0.6564	Remote Similarity	NPD3090	Approved
0.6564	Remote Similarity	NPD3088	Approved
0.6564	Remote Similarity	NPD4746	Phase 3
0.6564	Remote Similarity	NPD4745	Approved
0.6561	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7906	Approved
0.6561	Remote Similarity	NPD5618	Discontinued
0.6558	Remote Similarity	NPD7522	Discontinued
0.6552	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7497	Discontinued
0.6538	Remote Similarity	NPD2489	Approved
0.6538	Remote Similarity	NPD27	Approved
0.6526	Remote Similarity	NPD8360	Approved
0.6526	Remote Similarity	NPD8361	Approved
0.6524	Remote Similarity	NPD4577	Approved
0.6524	Remote Similarity	NPD4578	Approved
0.6522	Remote Similarity	NPD6042	Phase 2
0.6522	Remote Similarity	NPD42	Phase 2
0.6522	Remote Similarity	NPD4603	Phase 2
0.6519	Remote Similarity	NPD3051	Approved
0.6519	Remote Similarity	NPD7249	Approved
0.6519	Remote Similarity	NPD7250	Approved
0.6516	Remote Similarity	NPD4479	Discontinued
0.6512	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3638	Discontinued
0.6505	Remote Similarity	NPD8368	Discontinued
0.6497	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3123	Discovery
0.6486	Remote Similarity	NPD5557	Phase 1
0.6485	Remote Similarity	NPD4685	Phase 3
0.6485	Remote Similarity	NPD4684	Phase 3
0.6485	Remote Similarity	NPD4686	Approved
0.6481	Remote Similarity	NPD5203	Approved
0.6481	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4620	Approved
0.6481	Remote Similarity	NPD4617	Approved
0.6481	Remote Similarity	NPD5201	Approved
0.648	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6676	Phase 2
0.6467	Remote Similarity	NPD5239	Approved
0.6467	Remote Similarity	NPD5235	Approved
0.6467	Remote Similarity	NPD3909	Discontinued
0.6467	Remote Similarity	NPD5240	Approved
0.6467	Remote Similarity	NPD5236	Approved
0.6467	Remote Similarity	NPD5237	Approved
0.644	Remote Similarity	NPD8435	Approved
0.6433	Remote Similarity	NPD8131	Suspended
0.6433	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD5120	Approved
0.6424	Remote Similarity	NPD5119	Approved
0.6424	Remote Similarity	NPD5121	Approved
0.6424	Remote Similarity	NPD8265	Approved
0.6421	Remote Similarity	NPD4663	Approved
0.6409	Remote Similarity	NPD6746	Phase 2
0.6404	Remote Similarity	NPD5772	Approved
0.6404	Remote Similarity	NPD5773	Approved
0.6395	Remote Similarity	NPD7236	Approved
0.6391	Remote Similarity	NPD4725	Approved
0.6391	Remote Similarity	NPD4726	Approved
0.6391	Remote Similarity	NPD4721	Approved
0.6391	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7833	Phase 2
0.6389	Remote Similarity	NPD7831	Phase 2
0.6389	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.638	Remote Similarity	NPD2613	Approved
0.6379	Remote Similarity	NPD6222	Approved
0.6379	Remote Similarity	NPD6221	Approved
0.6378	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7253	Phase 3
0.6368	Remote Similarity	NPD5036	Approved
0.6352	Remote Similarity	NPD3381	Discontinued
0.6352	Remote Similarity	NPD4806	Approved
0.6352	Remote Similarity	NPD4480	Approved
0.6352	Remote Similarity	NPD4807	Approved
0.6352	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7565	Approved
0.6343	Remote Similarity	NPD3033	Phase 2
0.6337	Remote Similarity	NPD8323	Discontinued
0.6335	Remote Similarity	NPD3125	Approved
0.6335	Remote Similarity	NPD5037	Approved
0.6335	Remote Similarity	NPD5038	Approved
0.6323	Remote Similarity	NPD4032	Approved
0.6323	Remote Similarity	NPD4031	Approved
0.6322	Remote Similarity	NPD7020	Approved
0.6322	Remote Similarity	NPD7019	Approved
0.6322	Remote Similarity	NPD4123	Phase 3
0.6319	Remote Similarity	NPD5736	Approved
0.6319	Remote Similarity	NPD5204	Approved
0.6319	Remote Similarity	NPD3664	Approved
0.6319	Remote Similarity	NPD3661	Approved
0.6319	Remote Similarity	NPD3662	Phase 3
0.6319	Remote Similarity	NPD3663	Approved
0.6316	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2201	Approved
0.6316	Remote Similarity	NPD7179	Phase 2
0.6313	Remote Similarity	NPD4580	Approved
0.6312	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD2232	Approved
0.6312	Remote Similarity	NPD2230	Approved
0.6312	Remote Similarity	NPD2233	Approved
0.6307	Remote Similarity	NPD7239	Suspended
0.6286	Remote Similarity	NPD7613	Discontinued
0.6279	Remote Similarity	NPD3400	Discontinued
0.6279	Remote Similarity	NPD5754	Discontinued
0.6269	Remote Similarity	NPD4583	Approved
0.6269	Remote Similarity	NPD6836	Approved
0.6269	Remote Similarity	NPD4582	Approved
0.6266	Remote Similarity	NPD5981	Approved
0.6264	Remote Similarity	NPD5709	Phase 3
0.625	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6071	Discontinued
0.625	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2157	Approved
0.625	Remote Similarity	NPD3529	Phase 2
0.6244	Remote Similarity	NPD2973	Approved
0.6244	Remote Similarity	NPD7282	Approved
0.6244	Remote Similarity	NPD2974	Approved
0.6244	Remote Similarity	NPD2975	Approved
0.6243	Remote Similarity	NPD5029	Approved
0.6243	Remote Similarity	NPD5031	Approved
0.6243	Remote Similarity	NPD5027	Approved
0.6243	Remote Similarity	NPD7773	Phase 2
0.6242	Remote Similarity	NPD4738	Phase 2
0.6242	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4172	Approved
0.6235	Remote Similarity	NPD4173	Approved
0.623	Remote Similarity	NPD4666	Phase 3
0.6229	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD3645	Discontinued
0.6228	Remote Similarity	NPD6311	Approved
0.6228	Remote Similarity	NPD6310	Approved
0.6228	Remote Similarity	NPD6309	Approved
0.622	Remote Similarity	NPD3636	Approved
0.622	Remote Similarity	NPD3637	Approved
0.622	Remote Similarity	NPD3635	Approved
0.6219	Remote Similarity	NPD4004	Approved
0.6219	Remote Similarity	NPD4002	Approved
0.6218	Remote Similarity	NPD4198	Discontinued
0.6216	Remote Similarity	NPD4817	Approved
0.6216	Remote Similarity	NPD4719	Phase 2
0.6216	Remote Similarity	NPD4818	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