NPASS Compound

Structure

CID47857 OpenBabel06191715382D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.4680 -3.6433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4969 -1.5313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7881 0.1326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3550 -3.7401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2349 -0.0105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2430 -3.1107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1398 -0.5329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1270 -2.5993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2058 -2.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7397 -0.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3798 -1.5382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 -2.8247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3509 -0.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3381 -2.5883 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3445 -1.5549 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0191 -3.0934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6989 -0.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1969 -0.8153 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1334 -1.5660 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.1606 -4.2015 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3278 0.6631 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3134 -0.8533 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 0.7217 -3.0081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 11 2 0 0 0 0 4 12 2 0 0 0 0 5 7 1 0 0 0 0 5 13 2 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 14 6 1 1 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 19 1 6 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 3 1 6 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	333.16
Volume:	335.98
LogP:	1.647
LogD:	1.753
LogS:	-2.573
# Rotatable Bonds:	0
TPSA:	76.07
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	5.131
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.63
MDCK Permeability:	4.63540964119602e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.829
30% Bioavailability (F30%):	0.428

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.865
Plasma Protein Binding (PPB):	47.043853759765625%
Volume Distribution (VD):	1.512
Pgp-substrate:	67.57642364501953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.139
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.604
CYP2C9-inhibitor:	0.105
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.119
CYP2D6-substrate:	0.254
CYP3A4-inhibitor:	0.53
CYP3A4-substrate:	0.525

ADMET: Excretion

Clearance (CL):	5.761
Half-life (T1/2):	0.769

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.883
AMES Toxicity:	0.809
Rat Oral Acute Toxicity:	0.954
Maximum Recommended Daily Dose:	0.867
Skin Sensitization:	0.713
Carcinogencity:	0.916
Eye Corrosion:	0.213
Eye Irritation:	0.204
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC47857

Natural Product ID:	NPC47857
*Common Name:**	FCEVNJIUIMLVML-GTXMFSIISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FCEVNJIUIMLVML-GTXMFSIISA-N
Standard InCHI:	InChI=1S/C18H23NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,14-15,22H,2,6-10H2,1,3H3/b12-4-/t14-,15+,18-/m1/s1
SMILES:	C/C=C1/CC(=C)[C@@](C)(O)C(=O)OCC2=CCN3[C@@H]2[C@H](OC1=O)CC3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1439490
PubChem CID:	6560199
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives

*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
NPO3251	Jacobaea maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3251	Jacobaea maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27092	0cardia vaccinii	Species	0cardiaceae	Bacteria	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
Potency	8

Activity Type	# Activity
Individual Protein	6
Others	1
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	39810.7	nM	PMID[449025]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	15848.9	nM	PMID[449026]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[449025]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[449025]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[449027]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	44668.4	nM	PMID[449027]
NPT2	Others	Unspecified		Potency	n.a.	1122.0	nM	PMID[449028]

☑ 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 NPC47857 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	106
0.1-0.2	790
0.2-0.3	5066
0.3-0.4	20501
0.4-0.5	11547
0.5-0.6	4007
0.6-0.7	650
0.7-0.8	13
0.8-0.85	7
0.85-0.9	2
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC168758
1.0	High Similarity	NPC181510
0.9619	High Similarity	NPC193471
0.9619	High Similarity	NPC130124
0.9266	High Similarity	NPC284656
0.9266	High Similarity	NPC201889
0.9266	High Similarity	NPC106791
0.8584	High Similarity	NPC235625
0.8545	High Similarity	NPC30911
0.8545	High Similarity	NPC316984
0.8522	High Similarity	NPC23963
0.8241	Intermediate Similarity	NPC6271
0.8165	Intermediate Similarity	NPC64168
0.8073	Intermediate Similarity	NPC279833
0.8073	Intermediate Similarity	NPC80439
0.8073	Intermediate Similarity	NPC173690
0.7982	Intermediate Similarity	NPC474497
0.7965	Intermediate Similarity	NPC196073
0.7965	Intermediate Similarity	NPC195435
0.7826	Intermediate Similarity	NPC275100
0.75	Intermediate Similarity	NPC200412
0.75	Intermediate Similarity	NPC120599
0.75	Intermediate Similarity	NPC156336
0.7179	Intermediate Similarity	NPC474099
0.713	Intermediate Similarity	NPC474827
0.713	Intermediate Similarity	NPC68001
0.713	Intermediate Similarity	NPC199831
0.713	Intermediate Similarity	NPC474828
0.7097	Intermediate Similarity	NPC230849
0.7009	Intermediate Similarity	NPC469861
0.7009	Intermediate Similarity	NPC130436
0.7009	Intermediate Similarity	NPC469860
0.6917	Remote Similarity	NPC469603
0.6911	Remote Similarity	NPC30196
0.6897	Remote Similarity	NPC473289
0.6897	Remote Similarity	NPC474244
0.687	Remote Similarity	NPC477988
0.6855	Remote Similarity	NPC6531
0.6842	Remote Similarity	NPC476344
0.6842	Remote Similarity	NPC52820
0.6814	Remote Similarity	NPC150041
0.6786	Remote Similarity	NPC81419
0.6786	Remote Similarity	NPC475912
0.6786	Remote Similarity	NPC179746
0.6783	Remote Similarity	NPC471144
0.6767	Remote Similarity	NPC133089
0.6757	Remote Similarity	NPC476004
0.6757	Remote Similarity	NPC474761
0.6757	Remote Similarity	NPC51004
0.6748	Remote Similarity	NPC469597
0.6726	Remote Similarity	NPC81386
0.6726	Remote Similarity	NPC474035
0.6697	Remote Similarity	NPC112685
0.6696	Remote Similarity	NPC30515
0.6696	Remote Similarity	NPC473321
0.6696	Remote Similarity	NPC208886
0.6696	Remote Similarity	NPC12172
0.6692	Remote Similarity	NPC329401
0.6692	Remote Similarity	NPC477987
0.6692	Remote Similarity	NPC316401
0.6667	Remote Similarity	NPC36954
0.6667	Remote Similarity	NPC307411
0.6667	Remote Similarity	NPC14961
0.6667	Remote Similarity	NPC316133
0.6667	Remote Similarity	NPC271562
0.6667	Remote Similarity	NPC60432
0.6667	Remote Similarity	NPC1111
0.6667	Remote Similarity	NPC295312
0.6667	Remote Similarity	NPC318445
0.6667	Remote Similarity	NPC261750
0.6667	Remote Similarity	NPC270013
0.6667	Remote Similarity	NPC477011
0.6639	Remote Similarity	NPC469604
0.6638	Remote Similarity	NPC473326
0.6637	Remote Similarity	NPC476300
0.6636	Remote Similarity	NPC160138
0.6615	Remote Similarity	NPC477985
0.6615	Remote Similarity	NPC326386
0.6615	Remote Similarity	NPC471087
0.661	Remote Similarity	NPC149371
0.6607	Remote Similarity	NPC473619
0.6606	Remote Similarity	NPC100921
0.6606	Remote Similarity	NPC477018
0.6606	Remote Similarity	NPC21469
0.6591	Remote Similarity	NPC471086
0.6587	Remote Similarity	NPC65045
0.6585	Remote Similarity	NPC474431
0.6585	Remote Similarity	NPC474411
0.6583	Remote Similarity	NPC93179
0.6581	Remote Similarity	NPC26597
0.6577	Remote Similarity	NPC202672
0.6577	Remote Similarity	NPC89001
0.6565	Remote Similarity	NPC474371
0.6562	Remote Similarity	NPC11379
0.6557	Remote Similarity	NPC38154
0.6555	Remote Similarity	NPC475945
0.6555	Remote Similarity	NPC475871
0.6555	Remote Similarity	NPC472755
0.6549	Remote Similarity	NPC184463
0.6545	Remote Similarity	NPC231096
0.6545	Remote Similarity	NPC477010
0.6545	Remote Similarity	NPC107717
0.6545	Remote Similarity	NPC142117
0.6545	Remote Similarity	NPC475581
0.6545	Remote Similarity	NPC240695
0.6545	Remote Similarity	NPC309211
0.6545	Remote Similarity	NPC171174
0.6545	Remote Similarity	NPC114694
0.6545	Remote Similarity	NPC232555
0.6545	Remote Similarity	NPC62118
0.6538	Remote Similarity	NPC111162
0.6538	Remote Similarity	NPC477990
0.6538	Remote Similarity	NPC323168
0.6538	Remote Similarity	NPC293550
0.6538	Remote Similarity	NPC477989
0.6535	Remote Similarity	NPC174463
0.6525	Remote Similarity	NPC133907
0.6525	Remote Similarity	NPC110443
0.6525	Remote Similarity	NPC185141
0.6525	Remote Similarity	NPC476270
0.6525	Remote Similarity	NPC47880
0.6525	Remote Similarity	NPC128733
0.6525	Remote Similarity	NPC188785
0.6525	Remote Similarity	NPC46998
0.6525	Remote Similarity	NPC474742
0.6522	Remote Similarity	NPC471142
0.6518	Remote Similarity	NPC477017
0.6518	Remote Similarity	NPC477016
0.6515	Remote Similarity	NPC204556
0.6515	Remote Similarity	NPC476951
0.6515	Remote Similarity	NPC314282
0.6514	Remote Similarity	NPC156804
0.65	Remote Similarity	NPC474741
0.65	Remote Similarity	NPC100487
0.65	Remote Similarity	NPC44514
0.6496	Remote Similarity	NPC187268
0.6496	Remote Similarity	NPC300584
0.6493	Remote Similarity	NPC307165
0.6491	Remote Similarity	NPC273579
0.6491	Remote Similarity	NPC212486
0.6491	Remote Similarity	NPC162205
0.6491	Remote Similarity	NPC11456
0.6491	Remote Similarity	NPC295204
0.6491	Remote Similarity	NPC288240
0.6489	Remote Similarity	NPC314451
0.6489	Remote Similarity	NPC313333
0.6489	Remote Similarity	NPC314512
0.6489	Remote Similarity	NPC313342
0.6486	Remote Similarity	NPC154097
0.6486	Remote Similarity	NPC470401
0.6486	Remote Similarity	NPC473649
0.6486	Remote Similarity	NPC159750
0.6471	Remote Similarity	NPC120420
0.6471	Remote Similarity	NPC474747
0.6466	Remote Similarity	NPC476315
0.6466	Remote Similarity	NPC477921
0.646	Remote Similarity	NPC473904
0.6455	Remote Similarity	NPC231009
0.6455	Remote Similarity	NPC471567
0.6455	Remote Similarity	NPC329838
0.6455	Remote Similarity	NPC286338
0.6455	Remote Similarity	NPC66346
0.6455	Remote Similarity	NPC82795
0.6455	Remote Similarity	NPC110710
0.6455	Remote Similarity	NPC103284
0.6455	Remote Similarity	NPC473478
0.6455	Remote Similarity	NPC1083
0.6455	Remote Similarity	NPC329615
0.6455	Remote Similarity	NPC132496
0.6455	Remote Similarity	NPC473669
0.6455	Remote Similarity	NPC107986
0.6455	Remote Similarity	NPC283085
0.6455	Remote Similarity	NPC223871
0.6455	Remote Similarity	NPC120398
0.6455	Remote Similarity	NPC322529
0.6455	Remote Similarity	NPC473651
0.6452	Remote Similarity	NPC58281
0.6446	Remote Similarity	NPC243998
0.6446	Remote Similarity	NPC223450
0.6444	Remote Similarity	NPC120335
0.6441	Remote Similarity	NPC288876
0.6441	Remote Similarity	NPC475949
0.6435	Remote Similarity	NPC473330
0.6435	Remote Similarity	NPC473316
0.6429	Remote Similarity	NPC151403
0.6429	Remote Similarity	NPC287164
0.6429	Remote Similarity	NPC274446
0.6429	Remote Similarity	NPC100454
0.6429	Remote Similarity	NPC233551
0.6429	Remote Similarity	NPC169511
0.6429	Remote Similarity	NPC473715
0.6429	Remote Similarity	NPC61257
0.6429	Remote Similarity	NPC153805
0.6429	Remote Similarity	NPC234077
0.6429	Remote Similarity	NPC81045
0.6429	Remote Similarity	NPC39754
0.6429	Remote Similarity	NPC191929
0.6429	Remote Similarity	NPC261952
0.6429	Remote Similarity	NPC320569
0.6429	Remote Similarity	NPC472536

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 NPC47857 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	89
0.1-0.2	676
0.2-0.3	3236
0.3-0.4	3801
0.4-0.5	1131
0.5-0.6	195
0.6-0.7	21
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8545	High Similarity	NPD2204	Approved
0.6667	Remote Similarity	NPD7642	Approved
0.6618	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD8080	Discontinued
0.6565	Remote Similarity	NPD8451	Approved
0.6535	Remote Similarity	NPD7641	Discontinued
0.6515	Remote Similarity	NPD8448	Approved
0.6512	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD8341	Approved
0.6489	Remote Similarity	NPD8340	Approved
0.6489	Remote Similarity	NPD8342	Approved
0.6489	Remote Similarity	NPD8299	Approved
0.6457	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD8415	Approved
0.6397	Remote Similarity	NPD6845	Suspended
0.637	Remote Similarity	NPD8391	Approved
0.637	Remote Similarity	NPD8392	Approved
0.637	Remote Similarity	NPD8390	Approved
0.6316	Remote Similarity	NPD8273	Phase 1
0.626	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7260	Phase 2
0.6164	Remote Similarity	NPD2575	Approved
0.6111	Remote Similarity	NPD6421	Discontinued
0.6094	Remote Similarity	NPD1376	Discontinued
0.6045	Remote Similarity	NPD7830	Approved
0.6045	Remote Similarity	NPD7829	Approved
0.6042	Remote Similarity	NPD8384	Approved
0.5981	Remote Similarity	NPD1452	Discontinued
0.5971	Remote Similarity	NPD3661	Approved
0.5971	Remote Similarity	NPD3664	Approved
0.5971	Remote Similarity	NPD3662	Phase 3
0.5971	Remote Similarity	NPD3663	Approved
0.592	Remote Similarity	NPD4211	Phase 1
0.5897	Remote Similarity	NPD6698	Approved
0.5897	Remote Similarity	NPD46	Approved
0.5887	Remote Similarity	NPD1407	Approved
0.5857	Remote Similarity	NPD5204	Approved
0.5845	Remote Similarity	NPD4621	Approved
0.5845	Remote Similarity	NPD4619	Approved
0.5844	Remote Similarity	NPD8414	Discontinued
0.5827	Remote Similarity	NPD2625	Approved
0.5827	Remote Similarity	NPD2159	Approved
0.5827	Remote Similarity	NPD2160	Approved
0.5827	Remote Similarity	NPD2627	Approved
0.5827	Remote Similarity	NPD2628	Approved
0.5827	Remote Similarity	NPD2626	Approved
0.5778	Remote Similarity	NPD8444	Approved
0.5763	Remote Similarity	NPD7838	Discovery
0.576	Remote Similarity	NPD2259	Approved
0.576	Remote Similarity	NPD2258	Approved
0.5755	Remote Similarity	NPD8336	Approved
0.5755	Remote Similarity	NPD8337	Approved
0.5752	Remote Similarity	NPD882	Phase 2
0.5752	Remote Similarity	NPD883	Phase 2
0.5739	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD6371	Approved
0.5714	Remote Similarity	NPD7983	Approved
0.5692	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD1773	Discontinued
0.5662	Remote Similarity	NPD6909	Approved
0.5662	Remote Similarity	NPD6908	Approved
0.5656	Remote Similarity	NPD4228	Discovery
0.5655	Remote Similarity	NPD6311	Approved
0.5655	Remote Similarity	NPD6310	Approved
0.5655	Remote Similarity	NPD6309	Approved
0.5649	Remote Similarity	NPD6430	Approved
0.5649	Remote Similarity	NPD6429	Approved
0.5625	Remote Similarity	NPD3494	Approved
0.5625	Remote Similarity	NPD3493	Approved
0.5625	Remote Similarity	NPD3492	Approved
0.562	Remote Similarity	NPD7623	Phase 3
0.562	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5615	Remote Similarity	NPD6420	Discontinued
0.5612	Remote Similarity	NPD4816	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