NPASS Compound

Structure

CID266842 OpenBabel06191716072D 31 33 0 0 1 0 0 0 0 0999 V2000 -10.0266 1.1112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6198 0.1976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6253 0.0931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2186 -0.8205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2240 -0.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8173 -1.8385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8228 -1.9431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4161 -2.8566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4215 -2.9611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0148 -3.8747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0203 -3.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4325 -3.1702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8392 -2.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6582 -0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0759 0.1704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 0.2749 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2514 -1.4476 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9135 0.5933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5116 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4771 1.1885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2569 -1.5522 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 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 19 24 1 0 0 0 0 20 22 1 0 0 0 0 20 26 1 0 0 0 0 21 27 2 0 0 0 0 22 28 1 1 0 0 0 23 13 1 6 0 0 0 23 30 1 0 0 0 0 24 25 1 1 0 0 0 24 29 1 0 0 0 0 25 15 1 1 0 0 0 25 31 1 0 0 0 0 26 17 1 1 0 0 0 26 30 1 0 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.32
Volume:	471.261
LogP:	5.38
LogD:	3.969
LogS:	-5.528
# Rotatable Bonds:	12
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.403
Synthetic Accessibility Score:	5.023
Fsp3:	0.885
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862
MDCK Permeability:	3.7042256735730916e-05
Pgp-inhibitor:	0.803
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.141
Plasma Protein Binding (PPB):	97.60002899169922%
Volume Distribution (VD):	1.606
Pgp-substrate:	2.6745450496673584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.309
CYP2C19-inhibitor:	0.512
CYP2C19-substrate:	0.744
CYP2C9-inhibitor:	0.436
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.025
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.305

ADMET: Excretion

Clearance (CL):	12.275
Half-life (T1/2):	0.194

ADMET: Toxicity

hERG Blockers:	0.55
Human Hepatotoxicity (H-HT):	0.794
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.493
Rat Oral Acute Toxicity:	0.408
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.98
Carcinogencity:	0.937
Eye Corrosion:	0.147
Eye Irritation:	0.706
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC266842

Natural Product ID:	NPC266842
*Common Name:**	Aculeatol E
IUPAC Name:	(2R,4R,6S,8R,9S)-2,9-dihydroxy-4-tridecyl-5,7-dioxadispiro[5.1.5^{8}.2^{6}]pentadec-12-en-11-one
Synonyms:	aculeatol E
Standard InCHIKey:	UBFNRKJKPNNCHD-JMTTVTNBSA-N
Standard InCHI:	InChI=1S/C26H44O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-23-18-22(28)20-26(30-23)17-16-25(31-26)15-14-21(27)19-24(25)29/h14-15,22-24,28-29H,2-13,16-20H2,1H3/t22-,23-,24+,25+,26+/m1/s1
SMILES:	CCCCCCCCCCCCC[C@@H]1C[C@H](C[C@@]2(CC[C@]3(C=CC(=O)C[C@@H]3O)O2)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL439056
PubChem CID:	24853674
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

*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
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	1.8	uM	PMID[511185]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	4.4	uM	PMID[511185]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	3.9	uM	PMID[511185]

☑ 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 NPC266842 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	176
0.1-0.2	1118
0.2-0.3	4313
0.3-0.4	7793
0.4-0.5	14402
0.5-0.6	8544
0.6-0.7	5225
0.7-0.8	1101
0.8-0.85	16
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8778	High Similarity	NPC473353
0.8556	High Similarity	NPC2379
0.8556	High Similarity	NPC31019
0.8556	High Similarity	NPC27314
0.8556	High Similarity	NPC106912
0.8556	High Similarity	NPC263087
0.8283	Intermediate Similarity	NPC187761
0.8283	Intermediate Similarity	NPC83895
0.8182	Intermediate Similarity	NPC40812
0.8125	Intermediate Similarity	NPC471569
0.81	Intermediate Similarity	NPC255592
0.81	Intermediate Similarity	NPC308567
0.81	Intermediate Similarity	NPC261377
0.8095	Intermediate Similarity	NPC313668
0.8095	Intermediate Similarity	NPC315836
0.8058	Intermediate Similarity	NPC474917
0.8043	Intermediate Similarity	NPC475690
0.8019	Intermediate Similarity	NPC235014
0.8	Intermediate Similarity	NPC475960
0.8	Intermediate Similarity	NPC326753
0.798	Intermediate Similarity	NPC227494
0.7961	Intermediate Similarity	NPC475945
0.7961	Intermediate Similarity	NPC472750
0.7961	Intermediate Similarity	NPC472747
0.7961	Intermediate Similarity	NPC475871
0.7961	Intermediate Similarity	NPC309398
0.7935	Intermediate Similarity	NPC473339
0.7935	Intermediate Similarity	NPC471552
0.7921	Intermediate Similarity	NPC187268
0.7921	Intermediate Similarity	NPC203627
0.79	Intermediate Similarity	NPC306041
0.7885	Intermediate Similarity	NPC296950
0.7885	Intermediate Similarity	NPC472748
0.7885	Intermediate Similarity	NPC146731
0.7879	Intermediate Similarity	NPC71589
0.7879	Intermediate Similarity	NPC256368
0.7864	Intermediate Similarity	NPC313569
0.7864	Intermediate Similarity	NPC149371
0.7864	Intermediate Similarity	NPC223834
0.7864	Intermediate Similarity	NPC474747
0.7857	Intermediate Similarity	NPC30515
0.7857	Intermediate Similarity	NPC184463
0.7857	Intermediate Similarity	NPC476705
0.785	Intermediate Similarity	NPC46407
0.783	Intermediate Similarity	NPC193765
0.7822	Intermediate Similarity	NPC278506
0.781	Intermediate Similarity	NPC476740
0.781	Intermediate Similarity	NPC472749
0.781	Intermediate Similarity	NPC476738
0.781	Intermediate Similarity	NPC472751
0.78	Intermediate Similarity	NPC36954
0.7788	Intermediate Similarity	NPC474581
0.7788	Intermediate Similarity	NPC473816
0.7788	Intermediate Similarity	NPC475367
0.7788	Intermediate Similarity	NPC4620
0.7778	Intermediate Similarity	NPC320089
0.7778	Intermediate Similarity	NPC476300
0.7778	Intermediate Similarity	NPC471483
0.7778	Intermediate Similarity	NPC475912
0.7767	Intermediate Similarity	NPC154127
0.7767	Intermediate Similarity	NPC474742
0.7767	Intermediate Similarity	NPC164598
0.7767	Intermediate Similarity	NPC474339
0.7767	Intermediate Similarity	NPC47880
0.7767	Intermediate Similarity	NPC472753
0.7766	Intermediate Similarity	NPC477786
0.7766	Intermediate Similarity	NPC477785
0.7766	Intermediate Similarity	NPC477784
0.7755	Intermediate Similarity	NPC473311
0.7755	Intermediate Similarity	NPC51004
0.7745	Intermediate Similarity	NPC307517
0.7745	Intermediate Similarity	NPC61630
0.7745	Intermediate Similarity	NPC81483
0.7745	Intermediate Similarity	NPC169468
0.7732	Intermediate Similarity	NPC476708
0.7732	Intermediate Similarity	NPC476706
0.7732	Intermediate Similarity	NPC476707
0.7723	Intermediate Similarity	NPC143446
0.7723	Intermediate Similarity	NPC473859
0.7723	Intermediate Similarity	NPC54731
0.7717	Intermediate Similarity	NPC473980
0.7717	Intermediate Similarity	NPC473981
0.7714	Intermediate Similarity	NPC220964
0.7714	Intermediate Similarity	NPC474741
0.7714	Intermediate Similarity	NPC475676
0.7714	Intermediate Similarity	NPC203659
0.7714	Intermediate Similarity	NPC472756
0.7714	Intermediate Similarity	NPC100487
0.7708	Intermediate Similarity	NPC47937
0.77	Intermediate Similarity	NPC2003
0.77	Intermediate Similarity	NPC25701
0.7692	Intermediate Similarity	NPC472754
0.7685	Intermediate Similarity	NPC89408
0.7677	Intermediate Similarity	NPC472010
0.7677	Intermediate Similarity	NPC477749
0.7677	Intermediate Similarity	NPC470379
0.7677	Intermediate Similarity	NPC470373
0.767	Intermediate Similarity	NPC288876
0.7664	Intermediate Similarity	NPC473807
0.7664	Intermediate Similarity	NPC10150
0.766	Intermediate Similarity	NPC474252
0.7653	Intermediate Similarity	NPC130359
0.7653	Intermediate Similarity	NPC205548
0.7653	Intermediate Similarity	NPC14901
0.7653	Intermediate Similarity	NPC307411
0.7653	Intermediate Similarity	NPC133450
0.7647	Intermediate Similarity	NPC476612
0.7647	Intermediate Similarity	NPC474194
0.7647	Intermediate Similarity	NPC476613
0.7647	Intermediate Similarity	NPC471462
0.7634	Intermediate Similarity	NPC472948
0.7632	Intermediate Similarity	NPC470829
0.7632	Intermediate Similarity	NPC473228
0.7629	Intermediate Similarity	NPC300779
0.7624	Intermediate Similarity	NPC108141
0.7624	Intermediate Similarity	NPC475659
0.7624	Intermediate Similarity	NPC471141
0.7624	Intermediate Similarity	NPC270013
0.7624	Intermediate Similarity	NPC14961
0.7624	Intermediate Similarity	NPC473334
0.7619	Intermediate Similarity	NPC474165
0.7619	Intermediate Similarity	NPC110989
0.7619	Intermediate Similarity	NPC472755
0.7619	Intermediate Similarity	NPC151516
0.7619	Intermediate Similarity	NPC69171
0.7615	Intermediate Similarity	NPC126897
0.7615	Intermediate Similarity	NPC297945
0.7609	Intermediate Similarity	NPC475699
0.7604	Intermediate Similarity	NPC471494
0.7604	Intermediate Similarity	NPC182383
0.76	Intermediate Similarity	NPC288240
0.76	Intermediate Similarity	NPC81419
0.76	Intermediate Similarity	NPC473663
0.76	Intermediate Similarity	NPC273579
0.76	Intermediate Similarity	NPC212486
0.76	Intermediate Similarity	NPC472195
0.76	Intermediate Similarity	NPC179746
0.76	Intermediate Similarity	NPC295204
0.76	Intermediate Similarity	NPC469692
0.76	Intermediate Similarity	NPC475173
0.76	Intermediate Similarity	NPC238090
0.76	Intermediate Similarity	NPC472196
0.76	Intermediate Similarity	NPC473723
0.76	Intermediate Similarity	NPC162205
0.76	Intermediate Similarity	NPC469645
0.76	Intermediate Similarity	NPC473561
0.7596	Intermediate Similarity	NPC473332
0.7596	Intermediate Similarity	NPC476611
0.7593	Intermediate Similarity	NPC187876
0.7589	Intermediate Similarity	NPC477116
0.7589	Intermediate Similarity	NPC27999
0.7582	Intermediate Similarity	NPC474197
0.7579	Intermediate Similarity	NPC284472
0.7579	Intermediate Similarity	NPC286770
0.7579	Intermediate Similarity	NPC229799
0.7576	Intermediate Similarity	NPC177668
0.7576	Intermediate Similarity	NPC473619
0.7576	Intermediate Similarity	NPC475855
0.7576	Intermediate Similarity	NPC473904
0.7576	Intermediate Similarity	NPC179394
0.7576	Intermediate Similarity	NPC474761
0.7576	Intermediate Similarity	NPC473448
0.7576	Intermediate Similarity	NPC202886
0.7576	Intermediate Similarity	NPC476004
0.7576	Intermediate Similarity	NPC144133
0.7573	Intermediate Similarity	NPC40182
0.7573	Intermediate Similarity	NPC472015
0.7573	Intermediate Similarity	NPC471144
0.7573	Intermediate Similarity	NPC161855
0.7573	Intermediate Similarity	NPC198422
0.757	Intermediate Similarity	NPC324327
0.757	Intermediate Similarity	NPC194620
0.757	Intermediate Similarity	NPC72813
0.757	Intermediate Similarity	NPC474421
0.757	Intermediate Similarity	NPC326994
0.7551	Intermediate Similarity	NPC233551
0.7551	Intermediate Similarity	NPC202672
0.7551	Intermediate Similarity	NPC20339
0.7551	Intermediate Similarity	NPC40376
0.7551	Intermediate Similarity	NPC48338
0.7551	Intermediate Similarity	NPC87189
0.7551	Intermediate Similarity	NPC21208
0.7551	Intermediate Similarity	NPC280621
0.7551	Intermediate Similarity	NPC228415
0.7549	Intermediate Similarity	NPC230800
0.7549	Intermediate Similarity	NPC256230
0.7549	Intermediate Similarity	NPC476315
0.7549	Intermediate Similarity	NPC477921
0.7549	Intermediate Similarity	NPC279621
0.7549	Intermediate Similarity	NPC473291
0.7547	Intermediate Similarity	NPC469869
0.7545	Intermediate Similarity	NPC269530
0.7544	Intermediate Similarity	NPC48692
0.7544	Intermediate Similarity	NPC473130
0.7526	Intermediate Similarity	NPC473687
0.7526	Intermediate Similarity	NPC308412
0.7526	Intermediate Similarity	NPC69082
0.7526	Intermediate Similarity	NPC62118
0.7526	Intermediate Similarity	NPC478112
0.7526	Intermediate Similarity	NPC311163

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 NPC266842 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1486
0.2-0.3	3809
0.3-0.4	2426
0.4-0.5	805
0.5-0.6	326
0.6-0.7	136
0.7-0.8	12
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
0.7755	Intermediate Similarity	NPD46	Approved
0.7755	Intermediate Similarity	NPD6698	Approved
0.7745	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6686	Approved
0.7478	Intermediate Similarity	NPD8513	Phase 3
0.7478	Intermediate Similarity	NPD8516	Approved
0.7478	Intermediate Similarity	NPD8515	Approved
0.7478	Intermediate Similarity	NPD8517	Approved
0.7407	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6371	Approved
0.735	Intermediate Similarity	NPD7642	Approved
0.7184	Intermediate Similarity	NPD5282	Discontinued
0.7167	Intermediate Similarity	NPD8074	Phase 3
0.7157	Intermediate Similarity	NPD7983	Approved
0.7091	Intermediate Similarity	NPD6412	Phase 2
0.7059	Intermediate Similarity	NPD7830	Approved
0.7059	Intermediate Similarity	NPD5785	Approved
0.7059	Intermediate Similarity	NPD7838	Discovery
0.7059	Intermediate Similarity	NPD7829	Approved
0.6983	Remote Similarity	NPD7115	Discovery
0.6952	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6054	Approved
0.6916	Remote Similarity	NPD4225	Approved
0.69	Remote Similarity	NPD5363	Approved
0.6833	Remote Similarity	NPD6370	Approved
0.6803	Remote Similarity	NPD8451	Approved
0.6797	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD5778	Approved
0.675	Remote Similarity	NPD8444	Approved
0.675	Remote Similarity	NPD6016	Approved
0.675	Remote Similarity	NPD6015	Approved
0.6748	Remote Similarity	NPD8448	Approved
0.6733	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7839	Suspended
0.6726	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7492	Approved
0.6695	Remote Similarity	NPD7500	Approved
0.6694	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.664	Remote Similarity	NPD7319	Approved
0.6639	Remote Similarity	NPD7641	Discontinued
0.6636	Remote Similarity	NPD5344	Discontinued
0.6613	Remote Similarity	NPD7078	Approved
0.66	Remote Similarity	NPD4269	Approved
0.66	Remote Similarity	NPD4270	Approved
0.6587	Remote Similarity	NPD8390	Approved
0.6587	Remote Similarity	NPD8392	Approved
0.6587	Remote Similarity	NPD8391	Approved
0.6585	Remote Similarity	NPD8342	Approved
0.6585	Remote Similarity	NPD8340	Approved
0.6585	Remote Similarity	NPD8299	Approved
0.6585	Remote Similarity	NPD8341	Approved
0.6569	Remote Similarity	NPD1694	Approved
0.656	Remote Similarity	NPD7736	Approved
0.6532	Remote Similarity	NPD7507	Approved
0.6522	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5786	Approved
0.6504	Remote Similarity	NPD8328	Phase 3
0.6496	Remote Similarity	NPD6053	Discontinued
0.6476	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6101	Approved
0.6475	Remote Similarity	NPD7503	Approved
0.6471	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4251	Approved
0.6442	Remote Similarity	NPD4250	Approved
0.6423	Remote Similarity	NPD8080	Discontinued
0.641	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4252	Approved
0.6393	Remote Similarity	NPD6319	Approved
0.6379	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6110	Phase 1
0.6373	Remote Similarity	NPD7154	Phase 3
0.6355	Remote Similarity	NPD6411	Approved
0.6349	Remote Similarity	NPD8293	Discontinued
0.6346	Remote Similarity	NPD4249	Approved
0.6341	Remote Similarity	NPD8268	Approved
0.6341	Remote Similarity	NPD8269	Approved
0.6341	Remote Similarity	NPD8266	Approved
0.6341	Remote Similarity	NPD8267	Approved
0.6328	Remote Similarity	NPD5956	Approved
0.6325	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD1695	Approved
0.6281	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6009	Approved
0.6275	Remote Similarity	NPD6435	Approved
0.625	Remote Similarity	NPD6648	Approved
0.6238	Remote Similarity	NPD4821	Approved
0.6238	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4819	Approved
0.6238	Remote Similarity	NPD4822	Approved
0.6238	Remote Similarity	NPD4820	Approved
0.623	Remote Similarity	NPD7328	Approved
0.623	Remote Similarity	NPD7327	Approved
0.6218	Remote Similarity	NPD6882	Approved
0.621	Remote Similarity	NPD8033	Approved
0.621	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7637	Suspended
0.6186	Remote Similarity	NPD4634	Approved
0.6179	Remote Similarity	NPD7516	Approved
0.6172	Remote Similarity	NPD6033	Approved
0.6167	Remote Similarity	NPD8133	Approved
0.6167	Remote Similarity	NPD4632	Approved
0.6161	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD7260	Phase 2
0.6142	Remote Similarity	NPD8273	Phase 1
0.6129	Remote Similarity	NPD8377	Approved
0.6129	Remote Similarity	NPD8294	Approved
0.6106	Remote Similarity	NPD7639	Approved
0.6106	Remote Similarity	NPD7640	Approved
0.6083	Remote Similarity	NPD8297	Approved
0.608	Remote Similarity	NPD8379	Approved
0.608	Remote Similarity	NPD8335	Approved
0.608	Remote Similarity	NPD8380	Approved
0.608	Remote Similarity	NPD8378	Approved
0.608	Remote Similarity	NPD8296	Approved
0.608	Remote Similarity	NPD6921	Approved
0.6078	Remote Similarity	NPD5368	Approved
0.6068	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD7331	Phase 2
0.6058	Remote Similarity	NPD5362	Discontinued
0.6055	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4271	Approved
0.604	Remote Similarity	NPD4268	Approved
0.604	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5370	Suspended
0.6017	Remote Similarity	NPD6899	Approved
0.6017	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5985	Remote Similarity	NPD6845	Suspended
0.5984	Remote Similarity	NPD6067	Discontinued
0.5962	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5209	Approved
0.5943	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD5697	Approved
0.5929	Remote Similarity	NPD6084	Phase 2
0.5929	Remote Similarity	NPD6083	Phase 2
0.5922	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6883	Approved
0.5917	Remote Similarity	NPD7102	Approved
0.5917	Remote Similarity	NPD7290	Approved
0.5906	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7623	Phase 3
0.59	Remote Similarity	NPD8039	Approved
0.5896	Remote Similarity	NPD8415	Approved
0.5893	Remote Similarity	NPD4629	Approved
0.5893	Remote Similarity	NPD5210	Approved
0.5888	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD8130	Phase 1
0.5868	Remote Similarity	NPD6617	Approved
0.5868	Remote Similarity	NPD6847	Approved
0.5868	Remote Similarity	NPD6869	Approved
0.5862	Remote Similarity	NPD8138	Approved
0.5862	Remote Similarity	NPD8086	Approved
0.5862	Remote Similarity	NPD8085	Approved
0.5862	Remote Similarity	NPD8082	Approved
0.5862	Remote Similarity	NPD5211	Phase 2
0.5862	Remote Similarity	NPD8083	Approved
0.5862	Remote Similarity	NPD8084	Approved
0.5862	Remote Similarity	NPD8139	Approved
0.5859	Remote Similarity	NPD7604	Phase 2
0.5852	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6402	Approved
0.5847	Remote Similarity	NPD6008	Approved
0.5847	Remote Similarity	NPD7128	Approved
0.5847	Remote Similarity	NPD6675	Approved
0.5847	Remote Similarity	NPD5739	Approved
0.5833	Remote Similarity	NPD6372	Approved
0.5833	Remote Similarity	NPD6013	Approved
0.5833	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD6014	Approved
0.5833	Remote Similarity	NPD6373	Approved
0.5833	Remote Similarity	NPD7524	Approved
0.5827	Remote Similarity	NPD5983	Phase 2
0.5826	Remote Similarity	NPD5286	Approved
0.5826	Remote Similarity	NPD4696	Approved
0.5826	Remote Similarity	NPD5285	Approved
0.5812	Remote Similarity	NPD8275	Approved
0.5812	Remote Similarity	NPD8276	Approved
0.5802	Remote Similarity	NPD8336	Approved
0.5802	Remote Similarity	NPD8337	Approved
0.5794	Remote Similarity	NPD4522	Approved
0.5789	Remote Similarity	NPD7902	Approved
0.5789	Remote Similarity	NPD7341	Phase 2
0.5785	Remote Similarity	NPD6421	Discontinued
0.5784	Remote Similarity	NPD4756	Discovery
0.5769	Remote Similarity	NPD6336	Discontinued
0.5766	Remote Similarity	NPD6079	Approved
0.5763	Remote Similarity	NPD5141	Approved
0.5763	Remote Similarity	NPD8081	Approved
0.5752	Remote Similarity	NPD5695	Phase 3
0.575	Remote Similarity	NPD6011	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