NPASS Compound

Structure

NPC471552 OpenBabel07101718312D 33 35 0 0 1 0 0 0 0 0999 V2000 2.9731 -10.8194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2405 1.2386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5664 -9.9058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1542 -9.0968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7475 -8.1833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3352 -7.3742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9285 -6.4607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5163 -5.6517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1096 -4.7381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6973 -3.9291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2906 -3.0156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2961 -2.9110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8893 -1.9975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4771 -1.1885 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 -1.0933 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 -0.9135 -0.5933 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 1.2569 1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8337 2.1521 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 0.4067 0.0000 C 0 0 3 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 4.4215 2.9611 0.0000 O 0 0 0 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 2.8392 2.2567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0759 -0.1704 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 3 1 0 0 0 0 2 23 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 13 14 1 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 27 1 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 0 0 0 0 21 25 1 0 0 0 0 21 26 1 0 0 0 0 22 26 1 0 0 0 0 22 28 1 0 0 0 0 23 29 2 0 0 0 0 23 31 1 0 0 0 0 24 30 2 0 0 0 0 25 14 1 1 0 0 0 25 32 1 0 0 0 0 26 31 1 6 0 0 0 27 33 1 0 0 0 0 28 20 1 6 0 0 0 28 32 1 0 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.32
Volume:	500.58
LogP:	6.804
LogD:	4.359
LogS:	-6.331
# Rotatable Bonds:	14
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.225
Synthetic Accessibility Score:	4.757
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.762
MDCK Permeability:	4.467631515581161e-05
Pgp-inhibitor:	0.747
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.648
30% Bioavailability (F30%):	0.433

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	99.79520416259766%
Volume Distribution (VD):	1.959
Pgp-substrate:	1.6434794664382935%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.193
CYP2C19-inhibitor:	0.727
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.418
CYP2C9-substrate:	0.337
CYP2D6-inhibitor:	0.839
CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.825
CYP3A4-substrate:	0.395

ADMET: Excretion

Clearance (CL):	5.87
Half-life (T1/2):	0.188

ADMET: Toxicity

hERG Blockers:	0.765
Human Hepatotoxicity (H-HT):	0.819
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.166
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.986
Carcinogencity:	0.869
Eye Corrosion:	0.105
Eye Irritation:	0.689
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: NPC471552

Natural Product ID:	NPC471552
*Common Name:**	[(2R,4R,6S)-11-Oxo-4-Tridecyl-5,7-Dioxadispiro[5.1.5^{8}.2^{6}]Pentadeca-9,12-Dien-2-Yl] Acetate
IUPAC Name:	[(2R,4R,6S)-11-oxo-4-tridecyl-5,7-dioxadispiro[5.1.5^{8}.2^{6}]pentadeca-9,12-dien-2-yl] acetate
Synonyms:
Standard InCHIKey:	YIZCHFZJRZOMJL-GTNKKZTPSA-N
Standard InCHI:	InChI=1S/C28H44O5/c1-3-4-5-6-7-8-9-10-11-12-13-14-25-21-26(31-23(2)29)22-28(32-25)20-19-27(33-28)17-15-24(30)16-18-27/h15-18,25-26H,3-14,19-22H2,1-2H3/t25-,26-,28+/m1/s1
SMILES:	CCCCCCCCCCCCCC1CC(CC2(O1)CCC3(O2)C=CC(=O)C=C3)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256501
PubChem CID:	24853672
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	=	5.7	uM	PMID[542558]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	2.2	uM	PMID[542558]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	3.5	uM	PMID[542558]

☑ 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 NPC471552 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	169
0.1-0.2	1334
0.2-0.3	6044
0.3-0.4	14526
0.4-0.5	10476
0.5-0.6	7307
0.6-0.7	2671
0.7-0.8	160
0.8-0.85	1
0.85-0.9	2
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473339
0.9241	High Similarity	NPC263087
0.9241	High Similarity	NPC31019
0.9241	High Similarity	NPC106912
0.9241	High Similarity	NPC2379
0.9241	High Similarity	NPC27314
0.8929	High Similarity	NPC471569
0.878	High Similarity	NPC473353
0.8608	High Similarity	NPC326753
0.7935	Intermediate Similarity	NPC266842
0.7802	Intermediate Similarity	NPC256368
0.7727	Intermediate Similarity	NPC313658
0.7727	Intermediate Similarity	NPC316138
0.7667	Intermediate Similarity	NPC202886
0.7619	Intermediate Similarity	NPC139712
0.7582	Intermediate Similarity	NPC477749
0.7556	Intermediate Similarity	NPC477748
0.7556	Intermediate Similarity	NPC133450
0.75	Intermediate Similarity	NPC471494
0.7474	Intermediate Similarity	NPC203627
0.7473	Intermediate Similarity	NPC177668
0.7471	Intermediate Similarity	NPC170286
0.7442	Intermediate Similarity	NPC469469
0.7439	Intermediate Similarity	NPC477204
0.7416	Intermediate Similarity	NPC311163
0.7407	Intermediate Similarity	NPC475762
0.7386	Intermediate Similarity	NPC475035
0.7386	Intermediate Similarity	NPC266718
0.7356	Intermediate Similarity	NPC475690
0.734	Intermediate Similarity	NPC471362
0.734	Intermediate Similarity	NPC471372
0.734	Intermediate Similarity	NPC472189
0.7333	Intermediate Similarity	NPC199382
0.7317	Intermediate Similarity	NPC327383
0.7317	Intermediate Similarity	NPC185186
0.7312	Intermediate Similarity	NPC238090
0.7312	Intermediate Similarity	NPC472196
0.7312	Intermediate Similarity	NPC472195
0.7282	Intermediate Similarity	NPC471570
0.7263	Intermediate Similarity	NPC171598
0.7241	Intermediate Similarity	NPC8538
0.7241	Intermediate Similarity	NPC184208
0.7234	Intermediate Similarity	NPC159698
0.7234	Intermediate Similarity	NPC477722
0.7234	Intermediate Similarity	NPC88507
0.7222	Intermediate Similarity	NPC208473
0.7216	Intermediate Similarity	NPC13743
0.7216	Intermediate Similarity	NPC98813
0.7209	Intermediate Similarity	NPC473981
0.7209	Intermediate Similarity	NPC473980
0.72	Intermediate Similarity	NPC239961
0.7195	Intermediate Similarity	NPC477084
0.7188	Intermediate Similarity	NPC472188
0.7176	Intermediate Similarity	NPC477203
0.7174	Intermediate Similarity	NPC78008
0.716	Intermediate Similarity	NPC269841
0.7159	Intermediate Similarity	NPC10080
0.7159	Intermediate Similarity	NPC123908
0.7143	Intermediate Similarity	NPC2313
0.7143	Intermediate Similarity	NPC471056
0.7143	Intermediate Similarity	NPC327041
0.7143	Intermediate Similarity	NPC154132
0.7143	Intermediate Similarity	NPC475037
0.7143	Intermediate Similarity	NPC119467
0.7143	Intermediate Similarity	NPC471637
0.7143	Intermediate Similarity	NPC285840
0.7143	Intermediate Similarity	NPC57586
0.7143	Intermediate Similarity	NPC475157
0.7143	Intermediate Similarity	NPC475767
0.7143	Intermediate Similarity	NPC475655
0.7143	Intermediate Similarity	NPC471055
0.7129	Intermediate Similarity	NPC109376
0.7128	Intermediate Similarity	NPC471483
0.7125	Intermediate Similarity	NPC472266
0.7113	Intermediate Similarity	NPC476800
0.7113	Intermediate Similarity	NPC65700
0.7113	Intermediate Similarity	NPC472186
0.7113	Intermediate Similarity	NPC318917
0.7113	Intermediate Similarity	NPC471366
0.7111	Intermediate Similarity	NPC472442
0.7111	Intermediate Similarity	NPC155873
0.7108	Intermediate Similarity	NPC16349
0.7108	Intermediate Similarity	NPC329914
0.7108	Intermediate Similarity	NPC222244
0.7097	Intermediate Similarity	NPC144133
0.7097	Intermediate Similarity	NPC3952
0.7097	Intermediate Similarity	NPC179394
0.7097	Intermediate Similarity	NPC118078
0.7093	Intermediate Similarity	NPC248775
0.7093	Intermediate Similarity	NPC475699
0.7083	Intermediate Similarity	NPC311166
0.7083	Intermediate Similarity	NPC288350
0.7083	Intermediate Similarity	NPC173329
0.7079	Intermediate Similarity	NPC474809
0.7073	Intermediate Similarity	NPC469660
0.7071	Intermediate Similarity	NPC201191
0.7071	Intermediate Similarity	NPC471993
0.7071	Intermediate Similarity	NPC150463
0.7065	Intermediate Similarity	NPC106332
0.7059	Intermediate Similarity	NPC469880
0.7059	Intermediate Similarity	NPC470024
0.7059	Intermediate Similarity	NPC477202
0.7059	Intermediate Similarity	NPC224660
0.7053	Intermediate Similarity	NPC304968
0.7053	Intermediate Similarity	NPC474338
0.7053	Intermediate Similarity	NPC128488
0.7053	Intermediate Similarity	NPC469491
0.7048	Intermediate Similarity	NPC287075
0.7045	Intermediate Similarity	NPC315731
0.7041	Intermediate Similarity	NPC473204
0.7041	Intermediate Similarity	NPC472187
0.7041	Intermediate Similarity	NPC470761
0.7041	Intermediate Similarity	NPC473219
0.7041	Intermediate Similarity	NPC79631
0.7041	Intermediate Similarity	NPC473545
0.7037	Intermediate Similarity	NPC475760
0.7033	Intermediate Similarity	NPC50637
0.7033	Intermediate Similarity	NPC471480
0.703	Intermediate Similarity	NPC172867
0.703	Intermediate Similarity	NPC218158
0.7024	Intermediate Similarity	NPC474758
0.7021	Intermediate Similarity	NPC206679
0.7021	Intermediate Similarity	NPC476084
0.7021	Intermediate Similarity	NPC114172
0.7021	Intermediate Similarity	NPC476075
0.7021	Intermediate Similarity	NPC473944
0.7021	Intermediate Similarity	NPC471324
0.7011	Intermediate Similarity	NPC226226
0.7011	Intermediate Similarity	NPC470149
0.7011	Intermediate Similarity	NPC55304
0.7011	Intermediate Similarity	NPC470148
0.7011	Intermediate Similarity	NPC180725
0.701	Intermediate Similarity	NPC96597
0.701	Intermediate Similarity	NPC239547
0.701	Intermediate Similarity	NPC125551
0.701	Intermediate Similarity	NPC91197
0.701	Intermediate Similarity	NPC309503
0.701	Intermediate Similarity	NPC155319
0.701	Intermediate Similarity	NPC98112
0.701	Intermediate Similarity	NPC91695
0.701	Intermediate Similarity	NPC70145
0.7	Intermediate Similarity	NPC120009
0.7	Intermediate Similarity	NPC78673
0.7	Intermediate Similarity	NPC163615
0.7	Intermediate Similarity	NPC472747
0.7	Intermediate Similarity	NPC160517
0.7	Intermediate Similarity	NPC472750
0.7	Intermediate Similarity	NPC186155
0.7	Intermediate Similarity	NPC197736
0.7	Intermediate Similarity	NPC38569
0.7	Intermediate Similarity	NPC473308
0.7	Intermediate Similarity	NPC471301
0.7	Intermediate Similarity	NPC473070
0.6989	Remote Similarity	NPC166919
0.6989	Remote Similarity	NPC64913
0.6989	Remote Similarity	NPC242877
0.6979	Remote Similarity	NPC281134
0.6977	Remote Similarity	NPC233071
0.6977	Remote Similarity	NPC474026
0.697	Remote Similarity	NPC198992
0.697	Remote Similarity	NPC280991
0.6966	Remote Similarity	NPC471298
0.6966	Remote Similarity	NPC251026
0.6947	Remote Similarity	NPC159092
0.6947	Remote Similarity	NPC320089
0.6947	Remote Similarity	NPC109406
0.6939	Remote Similarity	NPC308567
0.6939	Remote Similarity	NPC187761
0.6939	Remote Similarity	NPC255592
0.6939	Remote Similarity	NPC261377
0.6939	Remote Similarity	NPC83895
0.6932	Remote Similarity	NPC133226
0.6932	Remote Similarity	NPC470147
0.6932	Remote Similarity	NPC474739
0.6931	Remote Similarity	NPC473068
0.6931	Remote Similarity	NPC169843
0.6931	Remote Similarity	NPC472748
0.6923	Remote Similarity	NPC215364
0.6923	Remote Similarity	NPC475034
0.6923	Remote Similarity	NPC316708
0.6923	Remote Similarity	NPC163606
0.6915	Remote Similarity	NPC80875
0.6915	Remote Similarity	NPC475855
0.6915	Remote Similarity	NPC62815
0.6915	Remote Similarity	NPC475748
0.6915	Remote Similarity	NPC473311
0.6915	Remote Similarity	NPC473448
0.6907	Remote Similarity	NPC73858
0.6907	Remote Similarity	NPC209297
0.6907	Remote Similarity	NPC194132
0.6907	Remote Similarity	NPC94905
0.6907	Remote Similarity	NPC475380
0.6907	Remote Similarity	NPC143446
0.6907	Remote Similarity	NPC8954
0.6905	Remote Similarity	NPC329890
0.6905	Remote Similarity	NPC476489
0.6905	Remote Similarity	NPC476490
0.69	Remote Similarity	NPC238397
0.69	Remote Similarity	NPC471363
0.6897	Remote Similarity	NPC23187

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 NPC471552 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1683
0.2-0.3	4402
0.3-0.4	2116
0.4-0.5	490
0.5-0.6	277
0.6-0.7	32
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
0.7292	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1694	Approved
0.6737	Remote Similarity	NPD7838	Discovery
0.6737	Remote Similarity	NPD46	Approved
0.6737	Remote Similarity	NPD6698	Approved
0.6731	Remote Similarity	NPD6686	Approved
0.6542	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6648	Approved
0.6471	Remote Similarity	NPD5344	Discontinued
0.646	Remote Similarity	NPD7503	Approved
0.6383	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD1695	Approved
0.625	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD4251	Approved
0.6237	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD5209	Approved
0.6195	Remote Similarity	NPD7328	Approved
0.6195	Remote Similarity	NPD7327	Approved
0.618	Remote Similarity	NPD8039	Approved
0.6174	Remote Similarity	NPD8513	Phase 3
0.6174	Remote Similarity	NPD8516	Approved
0.6174	Remote Similarity	NPD8517	Approved
0.6174	Remote Similarity	NPD8515	Approved
0.6168	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4249	Approved
0.6145	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7516	Approved
0.6122	Remote Similarity	NPD6051	Approved
0.6117	Remote Similarity	NPD7638	Approved
0.6087	Remote Similarity	NPD8294	Approved
0.6087	Remote Similarity	NPD8377	Approved
0.6075	Remote Similarity	NPD4211	Phase 1
0.6068	Remote Similarity	NPD7642	Approved
0.6061	Remote Similarity	NPD5785	Approved
0.6058	Remote Similarity	NPD7639	Approved
0.6058	Remote Similarity	NPD7640	Approved
0.604	Remote Similarity	NPD5282	Discontinued
0.6036	Remote Similarity	NPD6053	Discontinued
0.6034	Remote Similarity	NPD8378	Approved
0.6034	Remote Similarity	NPD8033	Approved
0.6034	Remote Similarity	NPD8296	Approved
0.6034	Remote Similarity	NPD8380	Approved
0.6034	Remote Similarity	NPD8335	Approved
0.6034	Remote Similarity	NPD8379	Approved
0.6022	Remote Similarity	NPD4822	Approved
0.6022	Remote Similarity	NPD4821	Approved
0.6022	Remote Similarity	NPD4820	Approved
0.6022	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD4819	Approved
0.6019	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD6371	Approved
0.598	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4225	Approved
0.5941	Remote Similarity	NPD5778	Approved
0.5941	Remote Similarity	NPD5779	Approved
0.5932	Remote Similarity	NPD7829	Approved
0.5932	Remote Similarity	NPD7830	Approved
0.5922	Remote Similarity	NPD7839	Suspended
0.5917	Remote Similarity	NPD8074	Phase 3
0.5895	Remote Similarity	NPD6435	Approved
0.5893	Remote Similarity	NPD6882	Approved
0.5882	Remote Similarity	NPD7492	Approved
0.5876	Remote Similarity	NPD5363	Approved
0.5876	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7637	Suspended
0.5842	Remote Similarity	NPD7983	Approved
0.5833	Remote Similarity	NPD7507	Approved
0.5833	Remote Similarity	NPD6616	Approved
0.5833	Remote Similarity	NPD7154	Phase 3
0.5816	Remote Similarity	NPD6684	Approved
0.5816	Remote Similarity	NPD7334	Approved
0.5816	Remote Similarity	NPD7146	Approved
0.5816	Remote Similarity	NPD5330	Approved
0.5816	Remote Similarity	NPD7521	Approved
0.5816	Remote Similarity	NPD6409	Approved
0.5812	Remote Similarity	NPD6054	Approved
0.5806	Remote Similarity	NPD4271	Approved
0.5806	Remote Similarity	NPD4268	Approved
0.5785	Remote Similarity	NPD7078	Approved
0.578	Remote Similarity	NPD6008	Approved
0.5766	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD7736	Approved
0.5714	Remote Similarity	NPD6370	Approved
0.5714	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5737	Approved
0.57	Remote Similarity	NPD6672	Approved
0.57	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.57	Remote Similarity	NPD6903	Approved
0.5691	Remote Similarity	NPD7319	Approved
0.569	Remote Similarity	NPD7115	Discovery
0.569	Remote Similarity	NPD6009	Approved
0.5686	Remote Similarity	NPD5693	Phase 1
0.5684	Remote Similarity	NPD5368	Approved
0.5676	Remote Similarity	NPD6881	Approved
0.5676	Remote Similarity	NPD6899	Approved
0.5648	Remote Similarity	NPD7632	Discontinued
0.5644	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6101	Approved
0.5641	Remote Similarity	NPD7641	Discontinued
0.5638	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.563	Remote Similarity	NPD8444	Approved
0.563	Remote Similarity	NPD6015	Approved
0.563	Remote Similarity	NPD6016	Approved
0.5625	Remote Similarity	NPD5369	Approved
0.5612	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.56	Remote Similarity	NPD3573	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