NPASS Compound

Structure

NPC475316 OpenBabel07101718222D 48 55 0 0 1 0 0 0 0 0999 V2000 0.4338 -1.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6937 1.9748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9340 2.3342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6851 -0.8990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0702 0.0306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3974 -0.9351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3737 -3.2536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3009 -3.0052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6950 -2.5749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5493 -2.0781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3974 2.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2286 2.0269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9648 0.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3305 0.9617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5126 0.5783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0640 0.3457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1558 1.3155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0377 1.0787 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9435 -1.6478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6572 0.5667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8538 0.7731 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8706 -1.3994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0882 0.9029 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4338 2.0269 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0151 -0.1283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8859 0.2615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3824 0.1339 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3974 0.5871 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4120 0.1492 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5150 0.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5860 -0.2904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2692 0.3457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2286 1.0670 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5059 -0.0826 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4338 1.0670 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 -0.3974 0.0247 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1190 -0.4722 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2651 2.5068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8201 -0.6510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5564 0.2235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6589 -0.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6106 -1.0367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2688 -1.4406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0979 1.8627 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7356 -0.7586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2069 -0.3888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8345 0.6368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 3 45 1 0 0 0 0 4 46 1 0 0 0 0 5 47 1 0 0 0 0 6 37 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 19 2 0 0 0 0 10 22 2 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 33 1 0 0 0 0 13 18 1 0 0 0 0 13 25 1 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 15 34 1 0 0 0 0 16 33 1 0 0 0 0 16 37 1 0 0 0 0 17 48 1 0 0 0 0 18 2 1 6 0 0 0 18 30 1 0 0 0 0 19 22 1 0 0 0 0 19 31 1 0 0 0 0 20 14 1 1 0 0 0 20 23 1 0 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 21 35 1 6 0 0 0 22 38 1 0 0 0 0 23 45 1 6 0 0 0 24 35 1 6 0 0 0 24 39 1 0 0 0 0 25 38 1 0 0 0 0 25 40 2 0 0 0 0 26 27 1 0 0 0 0 26 34 1 6 0 0 0 27 46 1 6 0 0 0 28 29 1 0 0 0 0 28 33 1 6 0 0 0 28 35 1 0 0 0 0 29 36 1 1 0 0 0 29 47 1 0 0 0 0 30 38 1 0 0 0 0 30 41 2 0 0 0 0 31 42 2 0 0 0 0 31 48 1 0 0 0 0 32 35 1 1 0 0 0 32 36 1 0 0 0 0 32 37 1 0 0 0 0 33 17 1 1 0 0 0 34 36 1 1 0 0 0 34 43 1 0 0 0 0 36 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	668.33
Volume:	656.837
LogP:	1.84
LogD:	2.511
LogS:	-4.235
# Rotatable Bonds:	9
TPSA:	163.31
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	8
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.262
Synthetic Accessibility Score:	7.314
Fsp3:	0.694
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:	-5.961
MDCK Permeability:	2.5355811885674484e-05
Pgp-inhibitor:	0.118
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.966
20% Bioavailability (F20%):	0.317
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	67.9678726196289%
Volume Distribution (VD):	0.588
Pgp-substrate:	33.55842208862305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.178
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.223
CYP3A4-substrate:	0.565

ADMET: Excretion

Clearance (CL):	3.128
Half-life (T1/2):	0.739

ADMET: Toxicity

hERG Blockers:	0.281
Human Hepatotoxicity (H-HT):	0.345
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.82
Skin Sensitization:	0.473
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.912

Download Data

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

Natural Product: NPC475316

Natural Product ID:	NPC475316
*Common Name:**	Grandiflorine
IUPAC Name:	n.a.
Synonyms:	Grandiflorine
Standard InCHIKey:	KPRGJDVXJLTFLK-KXAIAFPPSA-N
Standard InCHI:	InChI=1S/C36H48N2O10/c1-6-37-16-33(17-48-31(42)19-9-7-8-10-22(19)38-25(40)13-18(2)30(38)41)12-11-24(39)35-21-14-20-23(45-3)15-34(43,26(21)27(20)46-4)36(44,32(35)37)29(47-5)28(33)35/h7-10,18,20-21,23-24,26-29,32,39,43-44H,6,11-17H2,1-5H3/t18-,20+,21+,23-,24-,26+,27-,28+,29-,32-,33-,34+,35-,36-/m0/s1
SMILES:	CCN1CC2(CCC(C34C2C(C(C31)(C5(CC(C6CC4C5C6OC)OC)O)O)OC)O)COC(=O)C7=CC=CC=C7N8C(=O)CC(C8=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503364
PubChem CID:	44575472
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003788] Aconitane-type diterpenoid 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
NPO32441	delphinium sp.	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748371]

☑ 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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	8.3	mg.kg-1	PMID[542223]

☑ 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 NPC475316 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	389
0.1-0.2	1668
0.2-0.3	3566
0.3-0.4	12023
0.4-0.5	19192
0.5-0.6	4703
0.6-0.7	1014
0.7-0.8	103
0.8-0.85	25
0.85-0.9	5
0.9-0.95	1
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473486
0.9951	High Similarity	NPC473781
0.9951	High Similarity	NPC470631
0.9951	High Similarity	NPC35390
0.9183	High Similarity	NPC223590
0.9052	High Similarity	NPC106593
0.9009	High Similarity	NPC473667
0.8868	High Similarity	NPC140311
0.8815	High Similarity	NPC473837
0.8252	Intermediate Similarity	NPC205
0.8252	Intermediate Similarity	NPC124690
0.8252	Intermediate Similarity	NPC184195
0.8252	Intermediate Similarity	NPC166521
0.8252	Intermediate Similarity	NPC172769
0.8252	Intermediate Similarity	NPC281470
0.8116	Intermediate Similarity	NPC108276
0.8116	Intermediate Similarity	NPC163578
0.8068	Intermediate Similarity	NPC40539
0.7778	Intermediate Similarity	NPC475223
0.7742	Intermediate Similarity	NPC246983
0.7742	Intermediate Similarity	NPC475448
0.7727	Intermediate Similarity	NPC476496
0.7685	Intermediate Similarity	NPC475489
0.7602	Intermediate Similarity	NPC106840
0.7602	Intermediate Similarity	NPC94687
0.7602	Intermediate Similarity	NPC476495
0.7557	Intermediate Similarity	NPC326895
0.75	Intermediate Similarity	NPC473458
0.7489	Intermediate Similarity	NPC471512
0.7404	Intermediate Similarity	NPC475427
0.7373	Intermediate Similarity	NPC221687
0.735	Intermediate Similarity	NPC471513
0.7348	Intermediate Similarity	NPC288110
0.7311	Intermediate Similarity	NPC170751
0.73	Intermediate Similarity	NPC30456
0.7294	Intermediate Similarity	NPC198205
0.7294	Intermediate Similarity	NPC21483
0.7273	Intermediate Similarity	NPC311054
0.7273	Intermediate Similarity	NPC112752
0.726	Intermediate Similarity	NPC97100
0.726	Intermediate Similarity	NPC473375
0.7257	Intermediate Similarity	NPC475303
0.7257	Intermediate Similarity	NPC475596
0.7252	Intermediate Similarity	NPC176371
0.7252	Intermediate Similarity	NPC136573
0.7246	Intermediate Similarity	NPC471190
0.7246	Intermediate Similarity	NPC471977
0.7246	Intermediate Similarity	NPC470486
0.7246	Intermediate Similarity	NPC475644
0.724	Intermediate Similarity	NPC90358
0.724	Intermediate Similarity	NPC107828
0.7238	Intermediate Similarity	NPC160113
0.7238	Intermediate Similarity	NPC476220
0.7234	Intermediate Similarity	NPC476436
0.7227	Intermediate Similarity	NPC198390
0.7227	Intermediate Similarity	NPC476429
0.7222	Intermediate Similarity	NPC471980
0.7215	Intermediate Similarity	NPC477397
0.7203	Intermediate Similarity	NPC475600
0.7203	Intermediate Similarity	NPC476110
0.7203	Intermediate Similarity	NPC87152
0.7203	Intermediate Similarity	NPC475631
0.7191	Intermediate Similarity	NPC475137
0.7191	Intermediate Similarity	NPC475498
0.719	Intermediate Similarity	NPC476258
0.719	Intermediate Similarity	NPC304837
0.7185	Intermediate Similarity	NPC316841
0.7179	Intermediate Similarity	NPC127026
0.7179	Intermediate Similarity	NPC127720
0.7167	Intermediate Similarity	NPC475406
0.7167	Intermediate Similarity	NPC327769
0.7161	Intermediate Similarity	NPC473506
0.7149	Intermediate Similarity	NPC76565
0.7149	Intermediate Similarity	NPC473441
0.7149	Intermediate Similarity	NPC131273
0.7137	Intermediate Similarity	NPC327904
0.7137	Intermediate Similarity	NPC38959
0.7131	Intermediate Similarity	NPC477787
0.7131	Intermediate Similarity	NPC328186
0.7131	Intermediate Similarity	NPC228377
0.7131	Intermediate Similarity	NPC122968
0.7125	Intermediate Similarity	NPC237702
0.7124	Intermediate Similarity	NPC301368
0.7124	Intermediate Similarity	NPC84815
0.7119	Intermediate Similarity	NPC471583
0.7119	Intermediate Similarity	NPC477394
0.7119	Intermediate Similarity	NPC473850
0.7119	Intermediate Similarity	NPC471782
0.7113	Intermediate Similarity	NPC473689
0.7113	Intermediate Similarity	NPC292416
0.711	Intermediate Similarity	NPC105055
0.711	Intermediate Similarity	NPC22689
0.7101	Intermediate Similarity	NPC475362
0.7083	Intermediate Similarity	NPC319880
0.7083	Intermediate Similarity	NPC320324
0.7083	Intermediate Similarity	NPC322621
0.7083	Intermediate Similarity	NPC244839
0.7082	Intermediate Similarity	NPC294579
0.7082	Intermediate Similarity	NPC144779
0.7078	Intermediate Similarity	NPC278540
0.7076	Intermediate Similarity	NPC250807
0.7076	Intermediate Similarity	NPC57797
0.7072	Intermediate Similarity	NPC36607
0.7066	Intermediate Similarity	NPC17160
0.7066	Intermediate Similarity	NPC154922
0.7066	Intermediate Similarity	NPC313720
0.7061	Intermediate Similarity	NPC113455
0.7059	Intermediate Similarity	NPC146824
0.7059	Intermediate Similarity	NPC211920
0.7051	Intermediate Similarity	NPC222046
0.7048	Intermediate Similarity	NPC476500
0.7046	Intermediate Similarity	NPC477902
0.7045	Intermediate Similarity	NPC120239
0.7039	Intermediate Similarity	NPC471016
0.7039	Intermediate Similarity	NPC475408
0.7039	Intermediate Similarity	NPC471014
0.7039	Intermediate Similarity	NPC6981
0.7016	Intermediate Similarity	NPC477396
0.7009	Intermediate Similarity	NPC473089
0.7009	Intermediate Similarity	NPC62367
0.7009	Intermediate Similarity	NPC75600
0.7009	Intermediate Similarity	NPC473115
0.7009	Intermediate Similarity	NPC212768
0.7009	Intermediate Similarity	NPC6576
0.7009	Intermediate Similarity	NPC158020
0.7005	Intermediate Similarity	NPC73644
0.7004	Intermediate Similarity	NPC329932
0.7004	Intermediate Similarity	NPC311451
0.7004	Intermediate Similarity	NPC477393
0.6996	Remote Similarity	NPC475559
0.6996	Remote Similarity	NPC234772
0.6996	Remote Similarity	NPC470306
0.6995	Remote Similarity	NPC129624
0.6992	Remote Similarity	NPC477395
0.6992	Remote Similarity	NPC469452
0.6987	Remote Similarity	NPC124029
0.6979	Remote Similarity	NPC216428
0.6975	Remote Similarity	NPC328154
0.6967	Remote Similarity	NPC30171
0.6964	Remote Similarity	NPC475648
0.6962	Remote Similarity	NPC477788
0.6955	Remote Similarity	NPC475426
0.6953	Remote Similarity	NPC4421
0.694	Remote Similarity	NPC127996
0.693	Remote Similarity	NPC321211
0.6923	Remote Similarity	NPC469451
0.6923	Remote Similarity	NPC477907
0.6923	Remote Similarity	NPC477909
0.6923	Remote Similarity	NPC42678
0.692	Remote Similarity	NPC90967
0.692	Remote Similarity	NPC302548
0.692	Remote Similarity	NPC477912
0.6911	Remote Similarity	NPC469450
0.6911	Remote Similarity	NPC253482
0.6905	Remote Similarity	NPC253738
0.6901	Remote Similarity	NPC96801
0.6901	Remote Similarity	NPC477906
0.6901	Remote Similarity	NPC150698
0.6885	Remote Similarity	NPC35208
0.6875	Remote Similarity	NPC148860
0.687	Remote Similarity	NPC473565
0.6867	Remote Similarity	NPC472553
0.6867	Remote Similarity	NPC476467
0.6849	Remote Similarity	NPC477903
0.6847	Remote Similarity	NPC25401
0.6837	Remote Similarity	NPC476441
0.6835	Remote Similarity	NPC472555
0.6833	Remote Similarity	NPC477998
0.6825	Remote Similarity	NPC472574
0.682	Remote Similarity	NPC469312
0.682	Remote Similarity	NPC41318
0.681	Remote Similarity	NPC477160
0.6808	Remote Similarity	NPC469915
0.6807	Remote Similarity	NPC318525
0.6807	Remote Similarity	NPC10653
0.6803	Remote Similarity	NPC469748
0.6802	Remote Similarity	NPC301501
0.6802	Remote Similarity	NPC473298
0.6783	Remote Similarity	NPC329833
0.678	Remote Similarity	NPC477910
0.6777	Remote Similarity	NPC475601
0.6777	Remote Similarity	NPC313757
0.6776	Remote Similarity	NPC238278
0.6774	Remote Similarity	NPC475094
0.6773	Remote Similarity	NPC52262
0.6763	Remote Similarity	NPC477900
0.6763	Remote Similarity	NPC477899
0.6758	Remote Similarity	NPC477159
0.6757	Remote Similarity	NPC327699
0.6751	Remote Similarity	NPC206343
0.6751	Remote Similarity	NPC477908
0.675	Remote Similarity	NPC477911
0.675	Remote Similarity	NPC235364
0.6745	Remote Similarity	NPC472106
0.6744	Remote Similarity	NPC476425
0.6738	Remote Similarity	NPC472550
0.6738	Remote Similarity	NPC48042
0.6738	Remote Similarity	NPC304179
0.6737	Remote Similarity	NPC319128
0.6737	Remote Similarity	NPC264674

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 NPC475316 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	615
0.2-0.3	895
0.3-0.4	2548
0.4-0.5	3574
0.5-0.6	1227
0.6-0.7	62
0.7-0.8	3
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
0.75	Intermediate Similarity	NPD7497	Discontinued
0.715	Intermediate Similarity	NPD8658	Clinical (unspecified phase)
0.7106	Intermediate Similarity	NPD6997	Phase 2
0.6773	Remote Similarity	NPD8468	Phase 2
0.6696	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7962	Phase 2
0.6578	Remote Similarity	NPD8435	Approved
0.6578	Remote Similarity	NPD8361	Approved
0.6578	Remote Similarity	NPD8360	Approved
0.6569	Remote Similarity	NPD7047	Phase 3
0.6562	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8485	Approved
0.6531	Remote Similarity	NPD7186	Phase 3
0.6506	Remote Similarity	NPD6625	Approved
0.65	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD5742	Approved
0.6493	Remote Similarity	NPD5741	Approved
0.6493	Remote Similarity	NPD5743	Approved
0.6466	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD3437	Discontinued
0.6445	Remote Similarity	NPD4121	Phase 3
0.6445	Remote Similarity	NPD4120	Approved
0.6426	Remote Similarity	NPD7688	Phase 1
0.6416	Remote Similarity	NPD6891	Phase 2
0.6416	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6659	Phase 2
0.6395	Remote Similarity	NPD6805	Discontinued
0.6382	Remote Similarity	NPD3912	Discontinued
0.6376	Remote Similarity	NPD8146	Phase 2
0.6376	Remote Similarity	NPD7570	Approved
0.6376	Remote Similarity	NPD7569	Approved
0.6375	Remote Similarity	NPD6723	Discontinued
0.6364	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7048	Phase 3
0.636	Remote Similarity	NPD5928	Phase 1
0.6352	Remote Similarity	NPD6874	Approved
0.6347	Remote Similarity	NPD7795	Phase 2
0.6341	Remote Similarity	NPD6995	Phase 1
0.6332	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD8407	Phase 2
0.6327	Remote Similarity	NPD8459	Approved
0.6327	Remote Similarity	NPD8460	Approved
0.6324	Remote Similarity	NPD5891	Approved
0.632	Remote Similarity	NPD8364	Approved
0.632	Remote Similarity	NPD8363	Approved
0.6314	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.63	Remote Similarity	NPD8466	Approved
0.63	Remote Similarity	NPD8467	Approved
0.63	Remote Similarity	NPD8465	Approved
0.6296	Remote Similarity	NPD8149	Discontinued
0.629	Remote Similarity	NPD5997	Discontinued
0.6279	Remote Similarity	NPD7921	Approved
0.6274	Remote Similarity	NPD7606	Phase 3
0.6273	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD7803	Approved
0.6268	Remote Similarity	NPD7295	Approved
0.625	Remote Similarity	NPD7560	Approved
0.6245	Remote Similarity	NPD7205	Discontinued
0.6245	Remote Similarity	NPD7906	Approved
0.6245	Remote Similarity	NPD7922	Phase 1
0.6241	Remote Similarity	NPD7708	Approved
0.6235	Remote Similarity	NPD7805	Phase 3
0.6235	Remote Similarity	NPD7907	Approved
0.623	Remote Similarity	NPD5025	Approved
0.6223	Remote Similarity	NPD5411	Discontinued
0.6223	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.622	Remote Similarity	NPD2899	Discontinued
0.622	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7487	Discontinued
0.6215	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5430	Discontinued
0.6209	Remote Similarity	NPD8426	Approved
0.6209	Remote Similarity	NPD8425	Approved
0.6204	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD7956	Approved
0.6203	Remote Similarity	NPD7955	Approved
0.6202	Remote Similarity	NPD6716	Phase 1
0.6197	Remote Similarity	NPD2973	Approved
0.6197	Remote Similarity	NPD2974	Approved
0.6197	Remote Similarity	NPD2975	Approved
0.6195	Remote Similarity	NPD8368	Discontinued
0.6192	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4580	Approved
0.6182	Remote Similarity	NPD8428	Approved
0.6182	Remote Similarity	NPD8429	Approved
0.6182	Remote Similarity	NPD8427	Approved
0.6179	Remote Similarity	NPD7878	Phase 2
0.6173	Remote Similarity	NPD8462	Phase 1
0.6172	Remote Similarity	NPD4846	Phase 2
0.6172	Remote Similarity	NPD2820	Phase 3
0.617	Remote Similarity	NPD4668	Phase 2
0.6165	Remote Similarity	NPD8461	Discontinued
0.6163	Remote Similarity	NPD7417	Discontinued
0.6161	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7799	Discontinued
0.616	Remote Similarity	NPD3452	Approved
0.616	Remote Similarity	NPD2494	Approved
0.616	Remote Similarity	NPD2493	Approved
0.616	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.616	Remote Similarity	NPD3450	Approved
0.6157	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD2836	Approved
0.6154	Remote Similarity	NPD5582	Discontinued
0.6151	Remote Similarity	NPD8319	Approved
0.6151	Remote Similarity	NPD4583	Approved
0.6151	Remote Similarity	NPD8320	Phase 1
0.6151	Remote Similarity	NPD4582	Approved
0.6151	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD5609	Approved
0.6144	Remote Similarity	NPD5608	Approved
0.6143	Remote Similarity	NPD7854	Phase 2
0.6141	Remote Similarity	NPD7302	Phase 3
0.6141	Remote Similarity	NPD7300	Phase 3
0.614	Remote Similarity	NPD5086	Approved
0.6138	Remote Similarity	NPD8404	Phase 2
0.6132	Remote Similarity	NPD7478	Approved
0.6129	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD8161	Suspended
0.6124	Remote Similarity	NPD2365	Approved
0.6121	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.612	Remote Similarity	NPD7820	Phase 3
0.6109	Remote Similarity	NPD4002	Approved
0.6109	Remote Similarity	NPD4004	Approved
0.6107	Remote Similarity	NPD7225	Discontinued
0.6104	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD7528	Approved
0.6102	Remote Similarity	NPD5197	Approved
0.6102	Remote Similarity	NPD5194	Approved
0.6102	Remote Similarity	NPD5196	Approved
0.609	Remote Similarity	NPD8492	Approved
0.6089	Remote Similarity	NPD4111	Phase 1
0.6089	Remote Similarity	NPD4665	Approved
0.6081	Remote Similarity	NPD6457	Approved
0.6079	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD7810	Phase 3
0.6076	Remote Similarity	NPD7811	Phase 3
0.6075	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD7600	Phase 2
0.6068	Remote Similarity	NPD5610	Approved
0.6067	Remote Similarity	NPD5005	Approved
0.6067	Remote Similarity	NPD5006	Approved
0.6066	Remote Similarity	NPD5676	Approved
0.6066	Remote Similarity	NPD1945	Phase 1
0.6063	Remote Similarity	NPD4981	Phase 2
0.6061	Remote Similarity	NPD4663	Approved
0.6058	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD7278	Phase 2
0.6056	Remote Similarity	NPD7279	Phase 2
0.6052	Remote Similarity	NPD5042	Phase 1
0.6052	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6445	Discontinued
0.6041	Remote Similarity	NPD7301	Phase 3
0.6038	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD4420	Approved
0.6033	Remote Similarity	NPD7583	Approved
0.6027	Remote Similarity	NPD7599	Phase 2
0.6026	Remote Similarity	NPD8281	Discontinued
0.6025	Remote Similarity	NPD6238	Discontinued
0.6025	Remote Similarity	NPD5860	Discontinued
0.6025	Remote Similarity	NPD6321	Discontinued
0.6024	Remote Similarity	NPD6770	Approved
0.6024	Remote Similarity	NPD5496	Approved
0.6022	Remote Similarity	NPD7181	Phase 3
0.6019	Remote Similarity	NPD7082	Approved
0.601	Remote Similarity	NPD2670	Approved
0.6009	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD4082	Approved
0.6008	Remote Similarity	NPD7585	Approved
0.6008	Remote Similarity	NPD7701	Phase 2
0.6	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3057	Approved
0.6	Remote Similarity	NPD4577	Approved
0.6	Remote Similarity	NPD4493	Discontinued
0.6	Remote Similarity	NPD4578	Approved
0.5993	Remote Similarity	NPD8463	Approved
0.5992	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD4946	Phase 2
0.5992	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD7683	Discontinued
0.5991	Remote Similarity	NPD7259	Approved
0.5984	Remote Similarity	NPD8059	Phase 3
0.5984	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4107	Approved
0.5982	Remote Similarity	NPD5186	Approved
0.5982	Remote Similarity	NPD5183	Approved
0.5981	Remote Similarity	NPD8165	Discontinued
0.5981	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD1802	Approved
0.5981	Remote Similarity	NPD1801	Approved
0.5976	Remote Similarity	NPD7827	Phase 1
0.5973	Remote Similarity	NPD3422	Phase 3
0.5973	Remote Similarity	NPD3423	Phase 2

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