NPASS Compound

Structure

NPC475902 OpenBabel07101719242D 25 27 0 0 1 0 0 0 0 0999 V2000 6.9024 0.0105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5170 -1.6781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -3.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4511 1.3110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2473 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8134 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 2.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8134 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2999 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2222 -0.7225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -2.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2473 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0316 2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 2.0245 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0316 -2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2999 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5441 1.1801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4655 -2.9254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5181 -2.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0441 0.3141 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5692 1.1801 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 11 2 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 10 20 1 0 0 0 0 12 16 1 0 0 0 0 13 11 1 1 0 0 0 14 19 1 0 0 0 0 15 8 1 1 0 0 0 15 24 1 0 0 0 0 16 21 2 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 20 1 1 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 4 1 1 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.16
Volume:	356.939
LogP:	2.927
LogD:	1.86
LogS:	-4.011
# Rotatable Bonds:	1
TPSA:	80.04
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.791
Synthetic Accessibility Score:	5.981
Fsp3:	0.5
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:	-4.743
MDCK Permeability:	2.7177877200301737e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	91.89241027832031%
Volume Distribution (VD):	0.994
Pgp-substrate:	5.3711466789245605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.623
CYP2C19-inhibitor:	0.287
CYP2C19-substrate:	0.652
CYP2C9-inhibitor:	0.636
CYP2C9-substrate:	0.548
CYP2D6-inhibitor:	0.08
CYP2D6-substrate:	0.815
CYP3A4-inhibitor:	0.085
CYP3A4-substrate:	0.331

ADMET: Excretion

Clearance (CL):	8.209
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.126
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.411
Maximum Recommended Daily Dose:	0.424
Skin Sensitization:	0.436
Carcinogencity:	0.82
Eye Corrosion:	0.003
Eye Irritation:	0.038
Respiratory Toxicity:	0.48

Download Data

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

Natural Product: NPC475902

Natural Product ID:	NPC475902
*Common Name:**	Isoepoxylophodione
IUPAC Name:	n.a.
Synonyms:	Isoepoxylophodione
Standard InCHIKey:	MFBDZEVCKCRBMW-VPBHPPPASA-N
Standard InCHI:	InChI=1S/C20H24O5/c1-11(2)13-5-6-14-8-15(24-19(14)23)10-20(4)18(25-20)17(22)7-12(3)16(21)9-13/h7-8,13,15,18H,1,5-6,9-10H2,2-4H3/b12-7+/t13-,15-,18-,20-/m1/s1
SMILES:	CC(=C)[C@@H]1CCC2=C[C@@H](OC2=O)C[C@@]2([C@@H](C(=O)/C=C(/C(=O)C1)C)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518220
PubChem CID:	16099477
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO32683	lophogorgia peruana	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190454]

☑ 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
GI50	3
Others	5

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	2700.0	nM	PMID[484566]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	TGI	=	3200.0	nM	PMID[484566]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	2900.0	nM	PMID[484566]
NPT81	Cell Line	A549	Homo sapiens	TGI	=	5500.0	nM	PMID[484566]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	4100.0	nM	PMID[484566]
NPT139	Cell Line	HT-29	Homo sapiens	TGI	=	4400.0	nM	PMID[484566]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	LC50	=	4100.0	nM	PMID[484566]
NPT139	Cell Line	HT-29	Homo sapiens	LC50	=	4900.0	nM	PMID[484566]

☑ 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 NPC475902 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	252
0.1-0.2	1722
0.2-0.3	6366
0.3-0.4	12293
0.4-0.5	12941
0.5-0.6	5893
0.6-0.7	2546
0.7-0.8	626
0.8-0.85	45
0.85-0.9	11
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.907	High Similarity	NPC475906
0.907	High Similarity	NPC469653
0.907	High Similarity	NPC469631
0.907	High Similarity	NPC469628
0.907	High Similarity	NPC471047
0.8977	High Similarity	NPC20713
0.8736	High Similarity	NPC471739
0.8667	High Similarity	NPC165383
0.8587	High Similarity	NPC17585
0.8587	High Similarity	NPC476275
0.8571	High Similarity	NPC469632
0.8571	High Similarity	NPC140543
0.8523	High Similarity	NPC266957
0.8511	High Similarity	NPC469551
0.8471	Intermediate Similarity	NPC141810
0.8471	Intermediate Similarity	NPC286229
0.8452	Intermediate Similarity	NPC471740
0.8444	Intermediate Similarity	NPC329857
0.8444	Intermediate Similarity	NPC469718
0.8421	Intermediate Similarity	NPC477511
0.8421	Intermediate Similarity	NPC264477
0.8409	Intermediate Similarity	NPC261721
0.8409	Intermediate Similarity	NPC279859
0.8409	Intermediate Similarity	NPC38576
0.837	Intermediate Similarity	NPC476267
0.8333	Intermediate Similarity	NPC166919
0.8316	Intermediate Similarity	NPC477512
0.8315	Intermediate Similarity	NPC471738
0.8315	Intermediate Similarity	NPC475703
0.828	Intermediate Similarity	NPC474947
0.8276	Intermediate Similarity	NPC474703
0.8235	Intermediate Similarity	NPC276647
0.8235	Intermediate Similarity	NPC622
0.8235	Intermediate Similarity	NPC617
0.8229	Intermediate Similarity	NPC128733
0.8229	Intermediate Similarity	NPC185141
0.8229	Intermediate Similarity	NPC474339
0.8229	Intermediate Similarity	NPC46998
0.8229	Intermediate Similarity	NPC133907
0.8229	Intermediate Similarity	NPC110443
0.8229	Intermediate Similarity	NPC164598
0.8229	Intermediate Similarity	NPC201718
0.8211	Intermediate Similarity	NPC54843
0.8172	Intermediate Similarity	NPC473316
0.8172	Intermediate Similarity	NPC473330
0.8163	Intermediate Similarity	NPC474741
0.8163	Intermediate Similarity	NPC471143
0.8163	Intermediate Similarity	NPC477510
0.8111	Intermediate Similarity	NPC197333
0.8111	Intermediate Similarity	NPC231889
0.8105	Intermediate Similarity	NPC471140
0.809	Intermediate Similarity	NPC96621
0.809	Intermediate Similarity	NPC474547
0.8085	Intermediate Similarity	NPC474490
0.8068	Intermediate Similarity	NPC475989
0.8068	Intermediate Similarity	NPC272814
0.8068	Intermediate Similarity	NPC53867
0.8065	Intermediate Similarity	NPC475302
0.8061	Intermediate Similarity	NPC472755
0.8046	Intermediate Similarity	NPC475481
0.8046	Intermediate Similarity	NPC25684
0.8046	Intermediate Similarity	NPC301477
0.8046	Intermediate Similarity	NPC281949
0.8046	Intermediate Similarity	NPC79277
0.8046	Intermediate Similarity	NPC471325
0.8043	Intermediate Similarity	NPC475748
0.8043	Intermediate Similarity	NPC62815
0.8043	Intermediate Similarity	NPC312042
0.8041	Intermediate Similarity	NPC476270
0.8041	Intermediate Similarity	NPC472753
0.8023	Intermediate Similarity	NPC178277
0.8023	Intermediate Similarity	NPC270126
0.8021	Intermediate Similarity	NPC208233
0.8	Intermediate Similarity	NPC35498
0.8	Intermediate Similarity	NPC172998
0.8	Intermediate Similarity	NPC301596
0.8	Intermediate Similarity	NPC477513
0.8	Intermediate Similarity	NPC50637
0.8	Intermediate Similarity	NPC474716
0.8	Intermediate Similarity	NPC299396
0.7979	Intermediate Similarity	NPC121825
0.7979	Intermediate Similarity	NPC148463
0.7979	Intermediate Similarity	NPC471147
0.7978	Intermediate Similarity	NPC120726
0.7978	Intermediate Similarity	NPC32565
0.7959	Intermediate Similarity	NPC472754
0.7959	Intermediate Similarity	NPC149371
0.7957	Intermediate Similarity	NPC70595
0.7957	Intermediate Similarity	NPC123177
0.7957	Intermediate Similarity	NPC111114
0.7957	Intermediate Similarity	NPC261607
0.7957	Intermediate Similarity	NPC300312
0.7957	Intermediate Similarity	NPC150978
0.7957	Intermediate Similarity	NPC284185
0.7957	Intermediate Similarity	NPC74103
0.7955	Intermediate Similarity	NPC173609
0.7955	Intermediate Similarity	NPC35556
0.7938	Intermediate Similarity	NPC475949
0.7938	Intermediate Similarity	NPC288876
0.7935	Intermediate Similarity	NPC475971
0.7935	Intermediate Similarity	NPC151770
0.7931	Intermediate Similarity	NPC223904
0.7907	Intermediate Similarity	NPC128276
0.7895	Intermediate Similarity	NPC470978
0.7895	Intermediate Similarity	NPC234339
0.7895	Intermediate Similarity	NPC273197
0.7895	Intermediate Similarity	NPC470974
0.7895	Intermediate Similarity	NPC475659
0.7882	Intermediate Similarity	NPC123360
0.7879	Intermediate Similarity	NPC475945
0.7879	Intermediate Similarity	NPC475871
0.7872	Intermediate Similarity	NPC469692
0.7872	Intermediate Similarity	NPC469645
0.7865	Intermediate Similarity	NPC170377
0.7865	Intermediate Similarity	NPC475947
0.7864	Intermediate Similarity	NPC475495
0.7857	Intermediate Similarity	NPC476355
0.7857	Intermediate Similarity	NPC47880
0.7857	Intermediate Similarity	NPC474742
0.7857	Intermediate Similarity	NPC469851
0.7849	Intermediate Similarity	NPC253144
0.7843	Intermediate Similarity	NPC38154
0.7835	Intermediate Similarity	NPC471144
0.7812	Intermediate Similarity	NPC477354
0.7812	Intermediate Similarity	NPC473859
0.7812	Intermediate Similarity	NPC230800
0.7802	Intermediate Similarity	NPC284902
0.7802	Intermediate Similarity	NPC469483
0.7802	Intermediate Similarity	NPC107787
0.7802	Intermediate Similarity	NPC204048
0.7791	Intermediate Similarity	NPC97516
0.7791	Intermediate Similarity	NPC171204
0.7791	Intermediate Similarity	NPC57744
0.7791	Intermediate Similarity	NPC141789
0.7791	Intermediate Similarity	NPC476028
0.7789	Intermediate Similarity	NPC476596
0.7788	Intermediate Similarity	NPC475277
0.7788	Intermediate Similarity	NPC477093
0.7788	Intermediate Similarity	NPC473522
0.7778	Intermediate Similarity	NPC115786
0.7778	Intermediate Similarity	NPC471148
0.7778	Intermediate Similarity	NPC474747
0.7766	Intermediate Similarity	NPC32944
0.7766	Intermediate Similarity	NPC193396
0.7766	Intermediate Similarity	NPC219874
0.7766	Intermediate Similarity	NPC166110
0.7753	Intermediate Similarity	NPC85772
0.7753	Intermediate Similarity	NPC471326
0.7753	Intermediate Similarity	NPC221231
0.7753	Intermediate Similarity	NPC475690
0.7742	Intermediate Similarity	NPC95364
0.7742	Intermediate Similarity	NPC142159
0.7727	Intermediate Similarity	NPC474510
0.7727	Intermediate Similarity	NPC281132
0.7717	Intermediate Similarity	NPC72513
0.7708	Intermediate Similarity	NPC14961
0.7708	Intermediate Similarity	NPC270013
0.7692	Intermediate Similarity	NPC78089
0.7692	Intermediate Similarity	NPC470755
0.7692	Intermediate Similarity	NPC130030
0.7692	Intermediate Similarity	NPC261380
0.7684	Intermediate Similarity	NPC476598
0.7684	Intermediate Similarity	NPC202824
0.7684	Intermediate Similarity	NPC228451
0.7684	Intermediate Similarity	NPC125674
0.7684	Intermediate Similarity	NPC477361
0.7684	Intermediate Similarity	NPC476597
0.7684	Intermediate Similarity	NPC475838
0.7684	Intermediate Similarity	NPC212486
0.7684	Intermediate Similarity	NPC248193
0.767	Intermediate Similarity	NPC471934
0.7667	Intermediate Similarity	NPC128429
0.7667	Intermediate Similarity	NPC318468
0.766	Intermediate Similarity	NPC49342
0.766	Intermediate Similarity	NPC471818
0.766	Intermediate Similarity	NPC251385
0.766	Intermediate Similarity	NPC51653
0.7653	Intermediate Similarity	NPC264378
0.7653	Intermediate Similarity	NPC279561
0.7653	Intermediate Similarity	NPC473326
0.7653	Intermediate Similarity	NPC141191
0.7647	Intermediate Similarity	NPC469558
0.7647	Intermediate Similarity	NPC474758
0.7647	Intermediate Similarity	NPC140287
0.764	Intermediate Similarity	NPC325031
0.764	Intermediate Similarity	NPC42470
0.7629	Intermediate Similarity	NPC476315
0.7629	Intermediate Similarity	NPC473291
0.7624	Intermediate Similarity	NPC472756
0.7619	Intermediate Similarity	NPC163003
0.7619	Intermediate Similarity	NPC471933
0.7609	Intermediate Similarity	NPC305475
0.7609	Intermediate Similarity	NPC474045
0.7609	Intermediate Similarity	NPC261253
0.7609	Intermediate Similarity	NPC122502
0.7609	Intermediate Similarity	NPC469676
0.7609	Intermediate Similarity	NPC475461
0.7604	Intermediate Similarity	NPC81386
0.7604	Intermediate Similarity	NPC474247
0.7604	Intermediate Similarity	NPC474035

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 NPC475902 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	2289
0.2-0.3	3792
0.3-0.4	1923
0.4-0.5	615
0.5-0.6	233
0.6-0.7	52
0.7-0.8	6
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
0.7526	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5209	Approved
0.7188	Intermediate Similarity	NPD1695	Approved
0.7174	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6698	Approved
0.7113	Intermediate Similarity	NPD46	Approved
0.7108	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6371	Approved
0.6939	Remote Similarity	NPD5785	Approved
0.6771	Remote Similarity	NPD5363	Approved
0.6771	Remote Similarity	NPD1694	Approved
0.6768	Remote Similarity	NPD7838	Discovery
0.6733	Remote Similarity	NPD5282	Discontinued
0.6701	Remote Similarity	NPD5786	Approved
0.67	Remote Similarity	NPD5693	Phase 1
0.67	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6634	Remote Similarity	NPD5778	Approved
0.6634	Remote Similarity	NPD5779	Approved
0.6632	Remote Similarity	NPD6435	Approved
0.663	Remote Similarity	NPD4756	Discovery
0.6606	Remote Similarity	NPD6899	Approved
0.6606	Remote Similarity	NPD6881	Approved
0.6579	Remote Similarity	NPD7115	Discovery
0.6574	Remote Similarity	NPD5739	Approved
0.6574	Remote Similarity	NPD7128	Approved
0.6574	Remote Similarity	NPD6675	Approved
0.6574	Remote Similarity	NPD6402	Approved
0.6566	Remote Similarity	NPD5737	Approved
0.6566	Remote Similarity	NPD6672	Approved
0.6562	Remote Similarity	NPD7154	Phase 3
0.6545	Remote Similarity	NPD6012	Approved
0.6545	Remote Similarity	NPD6013	Approved
0.6545	Remote Similarity	NPD6014	Approved
0.6526	Remote Similarity	NPD5369	Approved
0.6514	Remote Similarity	NPD5701	Approved
0.6505	Remote Similarity	NPD5695	Phase 3
0.65	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6101	Approved
0.6486	Remote Similarity	NPD7102	Approved
0.6486	Remote Similarity	NPD7290	Approved
0.6486	Remote Similarity	NPD6883	Approved
0.6476	Remote Similarity	NPD4225	Approved
0.6458	Remote Similarity	NPD4269	Approved
0.6458	Remote Similarity	NPD4270	Approved
0.6455	Remote Similarity	NPD7320	Approved
0.6455	Remote Similarity	NPD6011	Approved
0.6429	Remote Similarity	NPD6617	Approved
0.6429	Remote Similarity	NPD8130	Phase 1
0.6429	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6649	Approved
0.6429	Remote Similarity	NPD6869	Approved
0.6429	Remote Similarity	NPD6847	Approved
0.6422	Remote Similarity	NPD6008	Approved
0.6421	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4252	Approved
0.6421	Remote Similarity	NPD5368	Approved
0.6396	Remote Similarity	NPD6373	Approved
0.6396	Remote Similarity	NPD6372	Approved
0.6381	Remote Similarity	NPD6083	Phase 2
0.6381	Remote Similarity	NPD6084	Phase 2
0.6373	Remote Similarity	NPD6411	Approved
0.6372	Remote Similarity	NPD6053	Discontinued
0.6372	Remote Similarity	NPD8297	Approved
0.6372	Remote Similarity	NPD6882	Approved
0.6337	Remote Similarity	NPD6904	Approved
0.6337	Remote Similarity	NPD6673	Approved
0.6337	Remote Similarity	NPD6080	Approved
0.6321	Remote Similarity	NPD5696	Approved
0.6306	Remote Similarity	NPD6686	Approved
0.6289	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7839	Suspended
0.6275	Remote Similarity	NPD5692	Phase 3
0.6271	Remote Similarity	NPD6319	Approved
0.6262	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4819	Approved
0.6237	Remote Similarity	NPD8039	Approved
0.6224	Remote Similarity	NPD5362	Discontinued
0.6216	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5694	Approved
0.6214	Remote Similarity	NPD6050	Approved
0.6211	Remote Similarity	NPD4268	Approved
0.6211	Remote Similarity	NPD4271	Approved
0.6207	Remote Similarity	NPD6274	Approved
0.6204	Remote Similarity	NPD5344	Discontinued
0.62	Remote Similarity	NPD7146	Approved
0.62	Remote Similarity	NPD6409	Approved
0.62	Remote Similarity	NPD7334	Approved
0.62	Remote Similarity	NPD7521	Approved
0.62	Remote Similarity	NPD5330	Approved
0.62	Remote Similarity	NPD6684	Approved
0.6195	Remote Similarity	NPD2067	Discontinued
0.6147	Remote Similarity	NPD5211	Phase 2
0.614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD3573	Approved
0.6116	Remote Similarity	NPD7642	Approved
0.6111	Remote Similarity	NPD5286	Approved
0.6111	Remote Similarity	NPD4696	Approved
0.6111	Remote Similarity	NPD5285	Approved
0.6106	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6903	Approved
0.6078	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD4755	Approved
0.6067	Remote Similarity	NPD7331	Phase 2
0.6066	Remote Similarity	NPD7492	Approved
0.6053	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.605	Remote Similarity	NPD7101	Approved
0.605	Remote Similarity	NPD7100	Approved
0.6042	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4249	Approved
0.604	Remote Similarity	NPD6422	Discontinued
0.604	Remote Similarity	NPD6098	Approved
0.6036	Remote Similarity	NPD5141	Approved
0.6019	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5370	Suspended
0.6017	Remote Similarity	NPD6317	Approved
0.6016	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD5224	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5984	Remote Similarity	NPD7830	Approved
0.5984	Remote Similarity	NPD7829	Approved
0.598	Remote Similarity	NPD4250	Approved
0.598	Remote Similarity	NPD4251	Approved
0.5968	Remote Similarity	NPD7078	Approved
0.5966	Remote Similarity	NPD6313	Approved
0.5966	Remote Similarity	NPD6314	Approved
0.5966	Remote Similarity	NPD6335	Approved
0.5963	Remote Similarity	NPD4700	Approved
0.5955	Remote Similarity	NPD7341	Phase 2
0.595	Remote Similarity	NPD6016	Approved
0.595	Remote Similarity	NPD6015	Approved
0.5946	Remote Similarity	NPD5174	Approved
0.5946	Remote Similarity	NPD5175	Approved
0.5943	Remote Similarity	NPD7900	Approved
0.5943	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5959	Approved
0.5923	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.592	Remote Similarity	NPD7736	Approved
0.5918	Remote Similarity	NPD4695	Discontinued
0.5913	Remote Similarity	NPD4634	Approved
0.5909	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5223	Approved
0.5905	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5988	Approved
0.5902	Remote Similarity	NPD8080	Discontinued
0.5902	Remote Similarity	NPD6370	Approved
0.5897	Remote Similarity	NPD4632	Approved
0.5889	Remote Similarity	NPD3704	Approved
0.5888	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5654	Approved
0.5882	Remote Similarity	NPD6009	Approved
0.5877	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7319	Approved
0.5872	Remote Similarity	NPD7638	Approved
0.5868	Remote Similarity	NPD6059	Approved
0.5865	Remote Similarity	NPD4753	Phase 2
0.5862	Remote Similarity	NPD2204	Approved
0.5854	Remote Similarity	NPD7604	Phase 2
0.584	Remote Similarity	NPD8293	Discontinued
0.5833	Remote Similarity	NPD5222	Approved
0.5833	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5221	Approved
0.582	Remote Similarity	NPD8513	Phase 3
0.582	Remote Similarity	NPD8516	Approved
0.582	Remote Similarity	NPD6909	Approved
0.582	Remote Similarity	NPD5983	Phase 2
0.582	Remote Similarity	NPD8515	Approved
0.582	Remote Similarity	NPD8517	Approved
0.582	Remote Similarity	NPD6908	Approved
0.5818	Remote Similarity	NPD7639	Approved
0.5818	Remote Similarity	NPD7640	Approved
0.5798	Remote Similarity	NPD6868	Approved
0.5794	Remote Similarity	NPD7748	Approved
0.5784	Remote Similarity	NPD1696	Phase 3
0.5781	Remote Similarity	NPD7260	Phase 2
0.578	Remote Similarity	NPD5173	Approved
0.578	Remote Similarity	NPD7902	Approved
0.5769	Remote Similarity	NPD5208	Approved
0.576	Remote Similarity	NPD7507	Approved
0.5755	Remote Similarity	NPD7637	Suspended
0.5743	Remote Similarity	NPD5331	Approved
0.5743	Remote Similarity	NPD6110	Phase 1
0.5743	Remote Similarity	NPD5332	Approved
0.5741	Remote Similarity	NPD5210	Approved
0.5741	Remote Similarity	NPD4629	Approved
0.5739	Remote Similarity	NPD4729	Approved
0.5739	Remote Similarity	NPD4730	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