NPASS Compound

Structure

NPC469631 OpenBabel07101718282D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.1502 2.4797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3814 1.4978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1095 -2.0356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2428 0.5119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3596 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4424 1.1502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8119 -1.3126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4442 0.9224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4442 -0.9224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3265 -0.2560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4823 1.6333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9154 0.9224 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2428 -0.5119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9173 1.1502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9173 -1.1502 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3265 0.2560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1168 0.5119 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6144 0.1453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1168 -0.5119 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7150 2.0367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1139 0.7106 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9392 1.9346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7952 -0.2492 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 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 12 1 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 9 19 1 0 0 0 0 10 16 1 0 0 0 0 10 19 1 0 0 0 0 12 11 1 6 0 0 0 13 18 1 0 0 0 0 14 20 2 0 0 0 0 15 7 1 1 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 8 1 6 0 0 0 17 24 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 3 1 1 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.16
Volume:	342.28
LogP:	2.401
LogD:	1.584
LogS:	-2.161
# Rotatable Bonds:	1
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.8
Synthetic Accessibility Score:	6.136
Fsp3:	0.579
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:	-4.726
MDCK Permeability:	2.438004048599396e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.225
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.692
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	62.388797760009766%
Volume Distribution (VD):	1.729
Pgp-substrate:	35.77249526977539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.465
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.575
CYP2C9-inhibitor:	0.094
CYP2C9-substrate:	0.331
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.851
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.305

ADMET: Excretion

Clearance (CL):	16.876
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.309
Drug-inuced Liver Injury (DILI):	0.606
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.746
Skin Sensitization:	0.244
Carcinogencity:	0.913
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.805

Download Data

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

Natural Product: NPC469631

Natural Product ID:	NPC469631
*Common Name:**	Gyrosanolide E
IUPAC Name:	n.a.
Synonyms:	Gyrosanolide E
Standard InCHIKey:	FDEJGIMXMYCYBJ-IQRRUJBNSA-N
Standard InCHI:	InChI=1S/C19H24O5/c1-11(2)12-4-5-13-7-15(23-18(13)22)9-19(3)10-16(21)17(24-19)8-14(20)6-12/h7,12,15,17H,1,4-6,8-10H2,2-3H3/t12-,15+,17+,19-/m0/s1
SMILES:	O=C1C[C@H](CCC2=C[C@H](C[C@@]3(O[C@H](C1)C(=O)C3)C)OC2=O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094877
PubChem CID:	46888448
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20430633]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20499851]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	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	4

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	>	20.0	ug ml-1	PMID[519242]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[519242]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[519242]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	ED50	>	50.0	ug ml-1	PMID[519242]

☑ 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 NPC469631 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	224
0.1-0.2	1532
0.2-0.3	6104
0.3-0.4	12422
0.4-0.5	12331
0.5-0.6	6322
0.6-0.7	2913
0.7-0.8	783
0.8-0.85	54
0.85-0.9	2
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471047
1.0	High Similarity	NPC469653
1.0	High Similarity	NPC475906
1.0	High Similarity	NPC469628
0.9425	High Similarity	NPC469632
0.907	High Similarity	NPC475902
0.9059	High Similarity	NPC279859
0.9059	High Similarity	NPC38576
0.8621	High Similarity	NPC261721
0.8617	High Similarity	NPC46998
0.8617	High Similarity	NPC110443
0.8617	High Similarity	NPC133907
0.8617	High Similarity	NPC128733
0.8617	High Similarity	NPC185141
0.8556	High Similarity	NPC20713
0.8488	Intermediate Similarity	NPC475947
0.8478	Intermediate Similarity	NPC474490
0.8404	Intermediate Similarity	NPC54843
0.8372	Intermediate Similarity	NPC173609
0.837	Intermediate Similarity	NPC476267
0.837	Intermediate Similarity	NPC121825
0.837	Intermediate Similarity	NPC140543
0.8353	Intermediate Similarity	NPC223904
0.8352	Intermediate Similarity	NPC300312
0.8352	Intermediate Similarity	NPC111114
0.8352	Intermediate Similarity	NPC261607
0.8352	Intermediate Similarity	NPC284185
0.8333	Intermediate Similarity	NPC128276
0.8315	Intermediate Similarity	NPC471739
0.8315	Intermediate Similarity	NPC475703
0.8261	Intermediate Similarity	NPC469645
0.8261	Intermediate Similarity	NPC469692
0.8256	Intermediate Similarity	NPC471325
0.8242	Intermediate Similarity	NPC253144
0.8235	Intermediate Similarity	NPC178277
0.8214	Intermediate Similarity	NPC57744
0.8202	Intermediate Similarity	NPC284902
0.8191	Intermediate Similarity	NPC301596
0.8191	Intermediate Similarity	NPC299396
0.8191	Intermediate Similarity	NPC172998
0.8191	Intermediate Similarity	NPC476275
0.8172	Intermediate Similarity	NPC148463
0.8152	Intermediate Similarity	NPC70595
0.8152	Intermediate Similarity	NPC74103
0.8152	Intermediate Similarity	NPC150978
0.8152	Intermediate Similarity	NPC123177
0.8095	Intermediate Similarity	NPC123360
0.8085	Intermediate Similarity	NPC234339
0.8085	Intermediate Similarity	NPC273197
0.8068	Intermediate Similarity	NPC474703
0.8065	Intermediate Similarity	NPC475302
0.8065	Intermediate Similarity	NPC165383
0.8061	Intermediate Similarity	NPC472755
0.8046	Intermediate Similarity	NPC42470
0.8046	Intermediate Similarity	NPC25684
0.8046	Intermediate Similarity	NPC301477
0.8046	Intermediate Similarity	NPC281949
0.8046	Intermediate Similarity	NPC141810
0.8046	Intermediate Similarity	NPC286229
0.8043	Intermediate Similarity	NPC329857
0.8043	Intermediate Similarity	NPC469718
0.8043	Intermediate Similarity	NPC312042
0.8041	Intermediate Similarity	NPC474742
0.8041	Intermediate Similarity	NPC477511
0.8041	Intermediate Similarity	NPC472753
0.8041	Intermediate Similarity	NPC264477
0.8023	Intermediate Similarity	NPC471740
0.802	Intermediate Similarity	NPC38154
0.8	Intermediate Similarity	NPC17585
0.8	Intermediate Similarity	NPC107787
0.7979	Intermediate Similarity	NPC473316
0.7979	Intermediate Similarity	NPC473330
0.7978	Intermediate Similarity	NPC115786
0.7959	Intermediate Similarity	NPC472754
0.7959	Intermediate Similarity	NPC149371
0.7955	Intermediate Similarity	NPC471326
0.7955	Intermediate Similarity	NPC221231
0.7955	Intermediate Similarity	NPC85772
0.7938	Intermediate Similarity	NPC469551
0.7935	Intermediate Similarity	NPC295312
0.7935	Intermediate Similarity	NPC166919
0.7912	Intermediate Similarity	NPC266957
0.7895	Intermediate Similarity	NPC474947
0.7889	Intermediate Similarity	NPC215364
0.7889	Intermediate Similarity	NPC125290
0.7889	Intermediate Similarity	NPC261380
0.7889	Intermediate Similarity	NPC78089
0.7879	Intermediate Similarity	NPC475873
0.7879	Intermediate Similarity	NPC475945
0.7879	Intermediate Similarity	NPC475871
0.7865	Intermediate Similarity	NPC318468
0.7865	Intermediate Similarity	NPC39588
0.7857	Intermediate Similarity	NPC117746
0.7857	Intermediate Similarity	NPC476355
0.7857	Intermediate Similarity	NPC164598
0.7857	Intermediate Similarity	NPC47880
0.7857	Intermediate Similarity	NPC201718
0.7857	Intermediate Similarity	NPC15499
0.7857	Intermediate Similarity	NPC474339
0.7857	Intermediate Similarity	NPC259599
0.7857	Intermediate Similarity	NPC474758
0.7857	Intermediate Similarity	NPC294434
0.7857	Intermediate Similarity	NPC469851
0.7849	Intermediate Similarity	NPC471818
0.7841	Intermediate Similarity	NPC35089
0.7841	Intermediate Similarity	NPC10276
0.7835	Intermediate Similarity	NPC208233
0.7835	Intermediate Similarity	NPC141191
0.7816	Intermediate Similarity	NPC617
0.7816	Intermediate Similarity	NPC276647
0.7816	Intermediate Similarity	NPC622
0.7816	Intermediate Similarity	NPC270126
0.7812	Intermediate Similarity	NPC185553
0.7812	Intermediate Similarity	NPC35498
0.7802	Intermediate Similarity	NPC70555
0.7802	Intermediate Similarity	NPC469483
0.7802	Intermediate Similarity	NPC70422
0.7802	Intermediate Similarity	NPC104961
0.78	Intermediate Similarity	NPC474741
0.78	Intermediate Similarity	NPC477510
0.78	Intermediate Similarity	NPC471143
0.7791	Intermediate Similarity	NPC65603
0.7791	Intermediate Similarity	NPC476794
0.7791	Intermediate Similarity	NPC180290
0.7791	Intermediate Similarity	NPC470240
0.7789	Intermediate Similarity	NPC167219
0.7789	Intermediate Similarity	NPC476596
0.7778	Intermediate Similarity	NPC140591
0.7778	Intermediate Similarity	NPC197835
0.7778	Intermediate Similarity	NPC120726
0.7778	Intermediate Similarity	NPC32565
0.7778	Intermediate Similarity	NPC303653
0.7778	Intermediate Similarity	NPC291500
0.7778	Intermediate Similarity	NPC474747
0.7778	Intermediate Similarity	NPC189609
0.7766	Intermediate Similarity	NPC219874
0.7766	Intermediate Similarity	NPC166110
0.7765	Intermediate Similarity	NPC244166
0.7755	Intermediate Similarity	NPC477512
0.7753	Intermediate Similarity	NPC475690
0.7732	Intermediate Similarity	NPC471140
0.7732	Intermediate Similarity	NPC169205
0.7727	Intermediate Similarity	NPC302426
0.7717	Intermediate Similarity	NPC197333
0.7717	Intermediate Similarity	NPC72513
0.7717	Intermediate Similarity	NPC478145
0.7717	Intermediate Similarity	NPC478144
0.7717	Intermediate Similarity	NPC471738
0.7717	Intermediate Similarity	NPC160138
0.7717	Intermediate Similarity	NPC231889
0.7708	Intermediate Similarity	NPC48803
0.7708	Intermediate Similarity	NPC470974
0.7708	Intermediate Similarity	NPC193645
0.7708	Intermediate Similarity	NPC275960
0.7708	Intermediate Similarity	NPC90121
0.7708	Intermediate Similarity	NPC470978
0.7701	Intermediate Similarity	NPC471220
0.7701	Intermediate Similarity	NPC299235
0.7692	Intermediate Similarity	NPC21471
0.7692	Intermediate Similarity	NPC161957
0.7692	Intermediate Similarity	NPC474547
0.7692	Intermediate Similarity	NPC33570
0.7692	Intermediate Similarity	NPC96621
0.7684	Intermediate Similarity	NPC476598
0.7684	Intermediate Similarity	NPC248193
0.7684	Intermediate Similarity	NPC476597
0.7677	Intermediate Similarity	NPC476270
0.7677	Intermediate Similarity	NPC477950
0.7674	Intermediate Similarity	NPC235906
0.7667	Intermediate Similarity	NPC215294
0.7667	Intermediate Similarity	NPC53867
0.7667	Intermediate Similarity	NPC128429
0.7667	Intermediate Similarity	NPC475989
0.7667	Intermediate Similarity	NPC272814
0.7667	Intermediate Similarity	NPC170377
0.766	Intermediate Similarity	NPC475748
0.766	Intermediate Similarity	NPC106510
0.766	Intermediate Similarity	NPC77337
0.766	Intermediate Similarity	NPC129419
0.766	Intermediate Similarity	NPC71533
0.766	Intermediate Similarity	NPC62815
0.7653	Intermediate Similarity	NPC471144
0.7647	Intermediate Similarity	NPC140287
0.7647	Intermediate Similarity	NPC477513
0.764	Intermediate Similarity	NPC325031
0.7634	Intermediate Similarity	NPC226863
0.7629	Intermediate Similarity	NPC184065
0.7624	Intermediate Similarity	NPC100487
0.7624	Intermediate Similarity	NPC472756
0.7619	Intermediate Similarity	NPC163003
0.7619	Intermediate Similarity	NPC84038
0.7614	Intermediate Similarity	NPC469620
0.7614	Intermediate Similarity	NPC469690
0.7609	Intermediate Similarity	NPC475491
0.7609	Intermediate Similarity	NPC305475
0.7609	Intermediate Similarity	NPC475461
0.7609	Intermediate Similarity	NPC50637
0.7609	Intermediate Similarity	NPC238593
0.7609	Intermediate Similarity	NPC469626
0.7604	Intermediate Similarity	NPC471147

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 NPC469631 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	2087
0.2-0.3	3923
0.3-0.4	1982
0.4-0.5	609
0.5-0.6	240
0.6-0.7	99
0.7-0.8	5
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
0.7708	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5209	Approved
0.7128	Intermediate Similarity	NPD1694	Approved
0.701	Intermediate Similarity	NPD1695	Approved
0.6939	Remote Similarity	NPD5785	Approved
0.6905	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5282	Discontinued
0.6875	Remote Similarity	NPD5786	Approved
0.6869	Remote Similarity	NPD5693	Phase 1
0.6771	Remote Similarity	NPD5363	Approved
0.6735	Remote Similarity	NPD5737	Approved
0.6735	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD5697	Approved
0.6636	Remote Similarity	NPD6371	Approved
0.6635	Remote Similarity	NPD4225	Approved
0.6634	Remote Similarity	NPD5779	Approved
0.6634	Remote Similarity	NPD5778	Approved
0.6632	Remote Similarity	NPD6435	Approved
0.6632	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6881	Approved
0.6606	Remote Similarity	NPD6899	Approved
0.6606	Remote Similarity	NPD7320	Approved
0.66	Remote Similarity	NPD46	Approved
0.66	Remote Similarity	NPD6698	Approved
0.6577	Remote Similarity	NPD6650	Approved
0.6577	Remote Similarity	NPD6649	Approved
0.6574	Remote Similarity	NPD5739	Approved
0.6574	Remote Similarity	NPD7128	Approved
0.6574	Remote Similarity	NPD6402	Approved
0.6574	Remote Similarity	NPD6675	Approved
0.6562	Remote Similarity	NPD7154	Phase 3
0.6545	Remote Similarity	NPD6012	Approved
0.6545	Remote Similarity	NPD6373	Approved
0.6545	Remote Similarity	NPD6013	Approved
0.6545	Remote Similarity	NPD6372	Approved
0.6545	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6083	Phase 2
0.6538	Remote Similarity	NPD6084	Phase 2
0.6535	Remote Similarity	NPD7983	Approved
0.6526	Remote Similarity	NPD5369	Approved
0.6514	Remote Similarity	NPD5701	Approved
0.65	Remote Similarity	NPD6101	Approved
0.65	Remote Similarity	NPD6080	Approved
0.65	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6673	Approved
0.65	Remote Similarity	NPD6904	Approved
0.6486	Remote Similarity	NPD7102	Approved
0.6486	Remote Similarity	NPD7290	Approved
0.6486	Remote Similarity	NPD6883	Approved
0.6476	Remote Similarity	NPD5696	Approved
0.6458	Remote Similarity	NPD4269	Approved
0.6458	Remote Similarity	NPD4270	Approved
0.6455	Remote Similarity	NPD6011	Approved
0.6452	Remote Similarity	NPD4756	Discovery
0.6436	Remote Similarity	NPD5692	Phase 3
0.6429	Remote Similarity	NPD6617	Approved
0.6429	Remote Similarity	NPD8130	Phase 1
0.6429	Remote Similarity	NPD6869	Approved
0.6429	Remote Similarity	NPD6847	Approved
0.6421	Remote Similarity	NPD5368	Approved
0.6413	Remote Similarity	NPD8039	Approved
0.64	Remote Similarity	NPD6903	Approved
0.6392	Remote Similarity	NPD5362	Discontinued
0.6373	Remote Similarity	NPD6411	Approved
0.6373	Remote Similarity	NPD6050	Approved
0.6373	Remote Similarity	NPD5694	Approved
0.6372	Remote Similarity	NPD6053	Discontinued
0.6372	Remote Similarity	NPD8297	Approved
0.6372	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD6409	Approved
0.6364	Remote Similarity	NPD5330	Approved
0.6364	Remote Similarity	NPD7334	Approved
0.6364	Remote Similarity	NPD7521	Approved
0.6364	Remote Similarity	NPD7146	Approved
0.6364	Remote Similarity	NPD6684	Approved
0.6333	Remote Similarity	NPD7492	Approved
0.6306	Remote Similarity	NPD6686	Approved
0.63	Remote Similarity	NPD3573	Approved
0.6293	Remote Similarity	NPD7115	Discovery
0.6286	Remote Similarity	NPD7839	Suspended
0.6281	Remote Similarity	NPD6616	Approved
0.6275	Remote Similarity	NPD7838	Discovery
0.6273	Remote Similarity	NPD6008	Approved
0.6271	Remote Similarity	NPD6319	Approved
0.6271	Remote Similarity	NPD6054	Approved
0.6263	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7331	Phase 2
0.625	Remote Similarity	NPD4252	Approved
0.6238	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7078	Approved
0.6218	Remote Similarity	NPD6015	Approved
0.6218	Remote Similarity	NPD6016	Approved
0.6211	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6274	Approved
0.62	Remote Similarity	NPD6098	Approved
0.619	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD7736	Approved
0.6172	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD5988	Approved
0.6167	Remote Similarity	NPD6370	Approved
0.6147	Remote Similarity	NPD5211	Phase 2
0.614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7341	Phase 2
0.6134	Remote Similarity	NPD6059	Approved
0.6117	Remote Similarity	NPD5207	Approved
0.6111	Remote Similarity	NPD5286	Approved
0.6111	Remote Similarity	NPD5285	Approved
0.6111	Remote Similarity	NPD4696	Approved
0.6098	Remote Similarity	NPD8293	Discontinued
0.6095	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7900	Approved
0.6082	Remote Similarity	NPD4820	Approved
0.6082	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4822	Approved
0.6082	Remote Similarity	NPD4821	Approved
0.6082	Remote Similarity	NPD4819	Approved
0.6075	Remote Similarity	NPD4755	Approved
0.6071	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD2067	Discontinued
0.605	Remote Similarity	NPD7101	Approved
0.605	Remote Similarity	NPD7100	Approved
0.604	Remote Similarity	NPD4249	Approved
0.6038	Remote Similarity	NPD5654	Approved
0.6036	Remote Similarity	NPD5141	Approved
0.6019	Remote Similarity	NPD7638	Approved
0.6019	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4753	Phase 2
0.6017	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD5224	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5981	Remote Similarity	NPD5221	Approved
0.5981	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4697	Phase 3
0.5981	Remote Similarity	NPD5222	Approved
0.598	Remote Similarity	NPD4250	Approved
0.598	Remote Similarity	NPD4251	Approved
0.5966	Remote Similarity	NPD6313	Approved
0.5966	Remote Similarity	NPD6335	Approved
0.5966	Remote Similarity	NPD6314	Approved
0.5963	Remote Similarity	NPD4700	Approved
0.5963	Remote Similarity	NPD7640	Approved
0.5963	Remote Similarity	NPD7639	Approved
0.595	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5175	Approved
0.5946	Remote Similarity	NPD5174	Approved
0.5943	Remote Similarity	NPD6001	Approved
0.5943	Remote Similarity	NPD7748	Approved
0.5932	Remote Similarity	NPD6868	Approved
0.5926	Remote Similarity	NPD5959	Approved
0.5926	Remote Similarity	NPD5173	Approved
0.5926	Remote Similarity	NPD7902	Approved
0.5922	Remote Similarity	NPD5208	Approved
0.5918	Remote Similarity	NPD4695	Discontinued
0.5913	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD4634	Approved
0.5909	Remote Similarity	NPD5223	Approved
0.59	Remote Similarity	NPD5332	Approved
0.59	Remote Similarity	NPD5331	Approved
0.5897	Remote Similarity	NPD4632	Approved
0.5888	Remote Similarity	NPD4629	Approved
0.5888	Remote Similarity	NPD5210	Approved
0.5887	Remote Similarity	NPD7507	Approved
0.5882	Remote Similarity	NPD5279	Phase 3
0.5882	Remote Similarity	NPD6422	Discontinued
0.5882	Remote Similarity	NPD6009	Approved
0.5877	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD4268	Approved
0.5876	Remote Similarity	NPD4271	Approved
0.5865	Remote Similarity	NPD5370	Suspended
0.5865	Remote Similarity	NPD6051	Approved
0.5862	Remote Similarity	NPD2204	Approved
0.5859	Remote Similarity	NPD4790	Discontinued
0.5826	Remote Similarity	NPD4061	Clinical (unspecified phase)
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	NPD6648	Approved
0.5789	Remote Similarity	NPD6614	Approved
0.5772	Remote Similarity	NPD8080	Discontinued
0.5766	Remote Similarity	NPD5344	Discontinued
0.5755	Remote Similarity	NPD7637	Suspended
0.5755	Remote Similarity	NPD6079	Approved
0.5755	Remote Similarity	NPD7515	Phase 2
0.5755	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6110	Phase 1

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