NPASS Compound

Structure

NPC247060 OpenBabel07101719512D 32 35 0 0 1 0 0 0 0 0999 V2000 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5683 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9234 2.4135 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 -5.2301 4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9429 3.2953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5902 2.7601 0.0000 C 0 0 1 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 -3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9211 3.5032 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 17 1 0 0 0 0 6 30 1 0 0 0 0 7 30 1 0 0 0 0 8 17 2 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 11 12 1 0 0 0 0 11 21 2 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 14 27 1 0 0 0 0 15 19 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 16 28 1 0 0 0 0 17 26 1 0 0 0 0 18 3 1 6 0 0 0 18 21 1 0 0 0 0 18 30 1 0 0 0 0 19 28 1 0 0 0 0 20 10 1 1 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 27 1 0 0 0 0 22 27 1 6 0 0 0 23 28 1 6 0 0 0 24 25 1 0 0 0 0 24 29 1 6 0 0 0 25 31 1 1 0 0 0 26 29 2 3 0 0 0 26 32 1 0 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.34
Volume:	487.646
LogP:	4.248
LogD:	3.824
LogS:	-4.428
# Rotatable Bonds:	5
TPSA:	52.57
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.485
Synthetic Accessibility Score:	5.052
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.997
MDCK Permeability:	1.1459042070782743e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.489
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.104
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.351
Plasma Protein Binding (PPB):	74.03290557861328%
Volume Distribution (VD):	1.533
Pgp-substrate:	21.581398010253906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.83
CYP2C19-inhibitor:	0.345
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.369
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.587
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.916
CYP3A4-substrate:	0.673

ADMET: Excretion

Clearance (CL):	8.904
Half-life (T1/2):	0.249

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.311
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.132
Carcinogencity:	0.803
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC247060

Natural Product ID:	NPC247060
*Common Name:**	1N-[14-[1-Dimethylamino-(1S)-Ethyl]-4-Hydroxy-2,15-Dimethyl-(1S,2R,4R,5R,10S,11S,15S)-Tetracyclo[8.7.0.02,7.011,15]Heptadeca-6,13-Dien-5-Yl]-2-Methyl-(E)-2-Butenamide
IUPAC Name:	(E)-N-[(2R,3R,8R,9S,10R,13S,14S)-17-[(1S)-1-(dimethylamino)ethyl]-2-hydroxy-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl]-2-methylbut-2-enamide
Synonyms:
Standard InCHIKey:	SFKQLDFGZQMCLQ-QBHBXPQWSA-N
Standard InCHI:	InChI=1S/C28H44N2O2/c1-8-17(2)26(32)29-24-15-19-9-10-20-22-12-11-21(18(3)30(6)7)27(22,4)14-13-23(20)28(19,5)16-25(24)31/h8,11,15,18,20,22-25,31H,9-10,12-14,16H2,1-7H3,(H,29,32)/b17-8+/t18-,20-,22-,23-,24+,25+,27+,28-/m0/s1
SMILES:	C/C=C(/C(=N[C@@H]1C=C2CC[C@@H]3[C@@H]([C@]2(C[C@H]1O)C)CC[C@]1([C@H]3CC=C1[C@@H](N(C)C)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL146080
PubChem CID:	10906319
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids

*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
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14584959]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14643329]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548847]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27888	Sarcococca saligna	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
IC50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2668	Individual Protein	Acetylcholinesterase	Torpedo californica	IC50	=	185200.0	nM	PMID[542547]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	=	23780.0	nM	PMID[542547]

☑ 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 NPC247060 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	80
0.1-0.2	632
0.2-0.3	6688
0.3-0.4	18672
0.4-0.5	10966
0.5-0.6	4833
0.6-0.7	756
0.7-0.8	63
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC50815
0.9184	High Similarity	NPC471083
0.8911	High Similarity	NPC55462
0.875	High Similarity	NPC472359
0.8511	High Similarity	NPC166458
0.84	Intermediate Similarity	NPC140300
0.8333	Intermediate Similarity	NPC34754
0.8218	Intermediate Similarity	NPC240650
0.8173	Intermediate Similarity	NPC293299
0.8173	Intermediate Similarity	NPC45365
0.8119	Intermediate Similarity	NPC476903
0.8113	Intermediate Similarity	NPC25340
0.81	Intermediate Similarity	NPC280710
0.81	Intermediate Similarity	NPC243985
0.8073	Intermediate Similarity	NPC80834
0.8073	Intermediate Similarity	NPC469968
0.8021	Intermediate Similarity	NPC75810
0.8	Intermediate Similarity	NPC474583
0.8	Intermediate Similarity	NPC90538
0.8	Intermediate Similarity	NPC93027
0.7982	Intermediate Similarity	NPC242692
0.7913	Intermediate Similarity	NPC472458
0.7909	Intermediate Similarity	NPC56796
0.78	Intermediate Similarity	NPC84171
0.7788	Intermediate Similarity	NPC91604
0.7692	Intermediate Similarity	NPC474164
0.7664	Intermediate Similarity	NPC241879
0.7596	Intermediate Similarity	NPC289140
0.7579	Intermediate Similarity	NPC109546
0.7579	Intermediate Similarity	NPC143182
0.7579	Intermediate Similarity	NPC84694
0.7579	Intermediate Similarity	NPC28862
0.7579	Intermediate Similarity	NPC47982
0.7579	Intermediate Similarity	NPC81306
0.757	Intermediate Similarity	NPC176012
0.757	Intermediate Similarity	NPC226509
0.7563	Intermediate Similarity	NPC237286
0.7547	Intermediate Similarity	NPC135799
0.7547	Intermediate Similarity	NPC275686
0.7524	Intermediate Similarity	NPC4834
0.75	Intermediate Similarity	NPC272732
0.75	Intermediate Similarity	NPC311164
0.75	Intermediate Similarity	NPC234193
0.7475	Intermediate Similarity	NPC152684
0.7474	Intermediate Similarity	NPC474216
0.7455	Intermediate Similarity	NPC46981
0.7431	Intermediate Similarity	NPC212874
0.7423	Intermediate Similarity	NPC23852
0.7423	Intermediate Similarity	NPC264245
0.7423	Intermediate Similarity	NPC209620
0.7407	Intermediate Similarity	NPC152718
0.7396	Intermediate Similarity	NPC30986
0.7396	Intermediate Similarity	NPC209430
0.7391	Intermediate Similarity	NPC165396
0.7387	Intermediate Similarity	NPC159367
0.7364	Intermediate Similarity	NPC36497
0.7347	Intermediate Similarity	NPC224072
0.7347	Intermediate Similarity	NPC50964
0.7347	Intermediate Similarity	NPC101462
0.7347	Intermediate Similarity	NPC49964
0.7347	Intermediate Similarity	NPC39966
0.7347	Intermediate Similarity	NPC189972
0.732	Intermediate Similarity	NPC164840
0.732	Intermediate Similarity	NPC241290
0.732	Intermediate Similarity	NPC209944
0.7297	Intermediate Similarity	NPC169375
0.7292	Intermediate Similarity	NPC473943
0.7273	Intermediate Similarity	NPC469958
0.7273	Intermediate Similarity	NPC475789
0.7273	Intermediate Similarity	NPC317458
0.7273	Intermediate Similarity	NPC474634
0.7263	Intermediate Similarity	NPC321016
0.7263	Intermediate Similarity	NPC244488
0.7263	Intermediate Similarity	NPC247325
0.7263	Intermediate Similarity	NPC321381
0.7263	Intermediate Similarity	NPC107059
0.7257	Intermediate Similarity	NPC328052
0.7245	Intermediate Similarity	NPC82986
0.7245	Intermediate Similarity	NPC474683
0.7245	Intermediate Similarity	NPC7505
0.7245	Intermediate Similarity	NPC474731
0.7245	Intermediate Similarity	NPC474759
0.7245	Intermediate Similarity	NPC47761
0.7245	Intermediate Similarity	NPC474752
0.7238	Intermediate Similarity	NPC473314
0.7217	Intermediate Similarity	NPC478137
0.72	Intermediate Similarity	NPC185568
0.72	Intermediate Similarity	NPC205845
0.7193	Intermediate Similarity	NPC66862
0.7188	Intermediate Similarity	NPC155986
0.7188	Intermediate Similarity	NPC318495
0.7188	Intermediate Similarity	NPC198968
0.7167	Intermediate Similarity	NPC478138
0.7158	Intermediate Similarity	NPC230301
0.7158	Intermediate Similarity	NPC304309
0.7158	Intermediate Similarity	NPC288035
0.7158	Intermediate Similarity	NPC134847
0.7158	Intermediate Similarity	NPC22105
0.7158	Intermediate Similarity	NPC136188
0.7158	Intermediate Similarity	NPC162742
0.7158	Intermediate Similarity	NPC285893
0.7158	Intermediate Similarity	NPC28657
0.7156	Intermediate Similarity	NPC118275
0.7129	Intermediate Similarity	NPC266511
0.7129	Intermediate Similarity	NPC274448
0.7117	Intermediate Similarity	NPC475239
0.7113	Intermediate Similarity	NPC87604
0.7113	Intermediate Similarity	NPC83351
0.7113	Intermediate Similarity	NPC167891
0.7113	Intermediate Similarity	NPC477522
0.7109	Intermediate Similarity	NPC132847
0.7094	Intermediate Similarity	NPC28280
0.7094	Intermediate Similarity	NPC304646
0.7087	Intermediate Similarity	NPC324405
0.7083	Intermediate Similarity	NPC300324
0.7083	Intermediate Similarity	NPC240604
0.7083	Intermediate Similarity	NPC113733
0.7071	Intermediate Similarity	NPC257962
0.7059	Intermediate Similarity	NPC293287
0.7059	Intermediate Similarity	NPC6391
0.7059	Intermediate Similarity	NPC152808
0.7059	Intermediate Similarity	NPC261266
0.7054	Intermediate Similarity	NPC86906
0.7054	Intermediate Similarity	NPC477292
0.7054	Intermediate Similarity	NPC258130
0.7041	Intermediate Similarity	NPC328714
0.703	Intermediate Similarity	NPC238485
0.703	Intermediate Similarity	NPC474047
0.7025	Intermediate Similarity	NPC469943
0.7021	Intermediate Similarity	NPC265789
0.7018	Intermediate Similarity	NPC253645
0.7018	Intermediate Similarity	NPC85001
0.7018	Intermediate Similarity	NPC95920
0.7018	Intermediate Similarity	NPC147835
0.701	Intermediate Similarity	NPC91594
0.701	Intermediate Similarity	NPC34019
0.7	Intermediate Similarity	NPC296701
0.7	Intermediate Similarity	NPC248886
0.7	Intermediate Similarity	NPC218616
0.7	Intermediate Similarity	NPC470049
0.7	Intermediate Similarity	NPC202389
0.7	Intermediate Similarity	NPC87489
0.7	Intermediate Similarity	NPC77703
0.699	Remote Similarity	NPC149224
0.6979	Remote Similarity	NPC141071
0.6979	Remote Similarity	NPC257347
0.6979	Remote Similarity	NPC471723
0.697	Remote Similarity	NPC26117
0.6964	Remote Similarity	NPC119329
0.6961	Remote Similarity	NPC157257
0.6957	Remote Similarity	NPC476290
0.6957	Remote Similarity	NPC72753
0.6947	Remote Similarity	NPC471799
0.6947	Remote Similarity	NPC474743
0.6939	Remote Similarity	NPC76931
0.6939	Remote Similarity	NPC11908
0.6939	Remote Similarity	NPC307965
0.6939	Remote Similarity	NPC18603
0.6939	Remote Similarity	NPC275910
0.6939	Remote Similarity	NPC477514
0.6939	Remote Similarity	NPC476314
0.6931	Remote Similarity	NPC470384
0.6923	Remote Similarity	NPC316186
0.6923	Remote Similarity	NPC474668
0.6915	Remote Similarity	NPC34834
0.6907	Remote Similarity	NPC96319
0.6907	Remote Similarity	NPC129165
0.6907	Remote Similarity	NPC134330
0.6907	Remote Similarity	NPC189883
0.69	Remote Similarity	NPC476646
0.69	Remote Similarity	NPC474531
0.69	Remote Similarity	NPC470383
0.6875	Remote Similarity	NPC471797
0.6875	Remote Similarity	NPC469534
0.6875	Remote Similarity	NPC474563
0.6875	Remote Similarity	NPC469533
0.6875	Remote Similarity	NPC469593
0.6869	Remote Similarity	NPC472463
0.6869	Remote Similarity	NPC1319
0.6863	Remote Similarity	NPC231310
0.6863	Remote Similarity	NPC470077
0.6857	Remote Similarity	NPC470361
0.6857	Remote Similarity	NPC146554
0.6857	Remote Similarity	NPC477606
0.6838	Remote Similarity	NPC476269
0.6837	Remote Similarity	NPC470711
0.6837	Remote Similarity	NPC214570
0.6837	Remote Similarity	NPC470758
0.6832	Remote Similarity	NPC5985
0.6832	Remote Similarity	NPC1272
0.6832	Remote Similarity	NPC470614
0.681	Remote Similarity	NPC287764
0.68	Remote Similarity	NPC295131
0.68	Remote Similarity	NPC236112
0.68	Remote Similarity	NPC96362
0.6796	Remote Similarity	NPC470360
0.6796	Remote Similarity	NPC318390
0.6796	Remote Similarity	NPC471224
0.6792	Remote Similarity	NPC11216
0.6792	Remote Similarity	NPC204188

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 NPC247060 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	81
0.1-0.2	315
0.2-0.3	2254
0.3-0.4	4344
0.4-0.5	1761
0.5-0.6	351
0.6-0.7	43
0.7-0.8	1
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
0.7573	Intermediate Similarity	NPD5771	Approved
0.7158	Intermediate Similarity	NPD7339	Approved
0.7158	Intermediate Similarity	NPD6942	Approved
0.6907	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4786	Approved
0.6634	Remote Similarity	NPD7525	Registered
0.6609	Remote Similarity	NPD6640	Phase 3
0.6609	Remote Similarity	NPD7333	Discontinued
0.6604	Remote Similarity	NPD4723	Approved
0.6604	Remote Similarity	NPD4722	Approved
0.66	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6929	Approved
0.6531	Remote Similarity	NPD6924	Approved
0.6531	Remote Similarity	NPD6926	Approved
0.6505	Remote Similarity	NPD3667	Approved
0.6471	Remote Similarity	NPD6930	Phase 2
0.6471	Remote Similarity	NPD6931	Approved
0.6471	Remote Similarity	NPD7332	Phase 2
0.646	Remote Similarity	NPD6404	Discontinued
0.6455	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6933	Approved
0.6385	Remote Similarity	NPD6914	Discontinued
0.6373	Remote Similarity	NPD7645	Phase 2
0.6371	Remote Similarity	NPD7522	Discontinued
0.6364	Remote Similarity	NPD4785	Approved
0.6364	Remote Similarity	NPD4784	Approved
0.6339	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6925	Approved
0.6337	Remote Similarity	NPD5776	Phase 2
0.6327	Remote Similarity	NPD7151	Approved
0.6327	Remote Similarity	NPD7152	Approved
0.6327	Remote Similarity	NPD7150	Approved
0.6327	Remote Similarity	NPD4243	Approved
0.6311	Remote Similarity	NPD7509	Discontinued
0.6311	Remote Similarity	NPD7514	Phase 3
0.63	Remote Similarity	NPD8264	Approved
0.6289	Remote Similarity	NPD6922	Approved
0.6289	Remote Similarity	NPD6923	Approved
0.6286	Remote Similarity	NPD6695	Phase 3
0.6275	Remote Similarity	NPD7145	Approved
0.625	Remote Similarity	NPD6902	Approved
0.625	Remote Similarity	NPD6420	Discontinued
0.625	Remote Similarity	NPD6898	Phase 1
0.6239	Remote Similarity	NPD5328	Approved
0.6238	Remote Similarity	NPD1346	Approved
0.6226	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7144	Approved
0.6224	Remote Similarity	NPD7143	Approved
0.6168	Remote Similarity	NPD6893	Approved
0.6154	Remote Similarity	NPD4748	Discontinued
0.6126	Remote Similarity	NPD6079	Approved
0.6111	Remote Similarity	NPD3618	Phase 1
0.6075	Remote Similarity	NPD3133	Approved
0.6075	Remote Similarity	NPD3665	Phase 1
0.6075	Remote Similarity	NPD3666	Approved
0.6071	Remote Similarity	NPD6399	Phase 3
0.6061	Remote Similarity	NPD6939	Phase 2
0.6061	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7524	Approved
0.6055	Remote Similarity	NPD7750	Discontinued
0.6036	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6932	Approved
0.6018	Remote Similarity	NPD5707	Approved
0.6016	Remote Similarity	NPD7335	Phase 2
0.6016	Remote Similarity	NPD6909	Approved
0.6016	Remote Similarity	NPD7336	Phase 2
0.6016	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6908	Approved
0.6	Remote Similarity	NPD7755	Approved
0.6	Remote Similarity	NPD7754	Approved
0.598	Remote Similarity	NPD4190	Phase 3
0.598	Remote Similarity	NPD5275	Approved
0.5968	Remote Similarity	NPD8298	Phase 2
0.5929	Remote Similarity	NPD4202	Approved
0.5926	Remote Similarity	NPD8449	Approved
0.5926	Remote Similarity	NPD3668	Phase 3
0.5917	Remote Similarity	NPD5357	Phase 1
0.5905	Remote Similarity	NPD6683	Phase 2
0.5905	Remote Similarity	NPD4195	Approved
0.5897	Remote Similarity	NPD7640	Approved
0.5897	Remote Similarity	NPD8418	Phase 2
0.5897	Remote Similarity	NPD7639	Approved
0.5882	Remote Similarity	NPD8450	Suspended
0.5862	Remote Similarity	NPD7920	Phase 3
0.5862	Remote Similarity	NPD7919	Phase 3
0.5859	Remote Similarity	NPD6705	Phase 1
0.5847	Remote Similarity	NPD4159	Approved
0.5846	Remote Similarity	NPD7725	Approved
0.5841	Remote Similarity	NPD7087	Discontinued
0.5818	Remote Similarity	NPD4519	Discontinued
0.5818	Remote Similarity	NPD4623	Approved
0.5818	Remote Similarity	NPD5279	Phase 3
0.5812	Remote Similarity	NPD7638	Approved
0.5812	Remote Similarity	NPD8088	Phase 1
0.5804	Remote Similarity	NPD6051	Approved
0.5804	Remote Similarity	NPD4753	Phase 2
0.5802	Remote Similarity	NPD7122	Discontinued
0.58	Remote Similarity	NPD15	Approved
0.58	Remote Similarity	NPD791	Approved
0.5798	Remote Similarity	NPD4719	Phase 2
0.5798	Remote Similarity	NPD5211	Phase 2
0.5793	Remote Similarity	NPD8131	Suspended
0.5789	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD4697	Phase 3
0.5776	Remote Similarity	NPD5221	Approved
0.5776	Remote Similarity	NPD5222	Approved
0.5776	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6700	Approved
0.5752	Remote Similarity	NPD7136	Phase 2
0.5745	Remote Similarity	NPD8148	Approved
0.5745	Remote Similarity	NPD8147	Approved
0.5741	Remote Similarity	NPD4223	Phase 3
0.5741	Remote Similarity	NPD4221	Approved
0.5727	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD5329	Approved
0.5726	Remote Similarity	NPD4755	Approved
0.5726	Remote Similarity	NPD5173	Approved
0.5726	Remote Similarity	NPD6421	Discontinued
0.5725	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD7623	Phase 3
0.5702	Remote Similarity	NPD7515	Phase 2
0.5702	Remote Similarity	NPD5141	Approved
0.5702	Remote Similarity	NPD7637	Suspended
0.5692	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.5683	Remote Similarity	NPD8118	Discontinued
0.5659	Remote Similarity	NPD3123	Discovery
0.5656	Remote Similarity	NPD5717	Approved
0.5656	Remote Similarity	NPD6920	Discontinued
0.5655	Remote Similarity	NPD3638	Discontinued
0.5639	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.5639	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD4197	Approved
0.5635	Remote Similarity	NPD8078	Approved
0.5635	Remote Similarity	NPD8077	Approved
0.563	Remote Similarity	NPD5285	Approved
0.563	Remote Similarity	NPD4696	Approved
0.563	Remote Similarity	NPD4700	Approved
0.563	Remote Similarity	NPD5286	Approved
0.5625	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD6676	Phase 2
0.561	Remote Similarity	NPD7646	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