NPASS Compound

Structure

NPC469718 OpenBabel07101718192D 24 26 0 0 1 0 0 0 0 0999 V2000 4.7662 -2.4045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0444 -5.8579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2879 -1.9824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8609 -0.6012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -4.2943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7941 -0.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6200 -3.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4743 -1.5237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1906 -4.7943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8632 -0.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -1.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7690 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1934 -4.8690 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7123 -2.8001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7124 -2.8151 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2626 -4.5037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4176 -3.7706 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.0355 -3.7464 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 -0.3008 -5.3299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9910 -4.0412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2353 -4.3463 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 12 1 0 0 0 0 3 14 2 0 0 0 0 5 7 1 0 0 0 0 5 9 1 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 7 12 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 10 20 1 0 0 0 0 11 16 1 0 0 0 0 13 2 1 1 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 11 1 6 0 0 0 15 18 1 0 0 0 0 16 20 1 1 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 23 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 4 1 1 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	353.422
LogP:	3.384
LogD:	1.393
LogS:	-3.362
# Rotatable Bonds:	0
TPSA:	55.9
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.293
Synthetic Accessibility Score:	4.978
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.683
MDCK Permeability:	2.1801084585604258e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.526
Plasma Protein Binding (PPB):	93.09362030029297%
Volume Distribution (VD):	1.208
Pgp-substrate:	3.9482903480529785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.112
CYP1A2-substrate:	0.474
CYP2C19-inhibitor:	0.392
CYP2C19-substrate:	0.413
CYP2C9-inhibitor:	0.579
CYP2C9-substrate:	0.129
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.261
CYP3A4-inhibitor:	0.59
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	8.367
Half-life (T1/2):	0.453

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.876
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.822
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.923
Carcinogencity:	0.183
Eye Corrosion:	0.962
Eye Irritation:	0.865
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC469718

Natural Product ID:	NPC469718
*Common Name:**	Succinolide
IUPAC Name:	n.a.
Synonyms:	Succinolide
Standard InCHIKey:	FGMVUGQMSRSYDL-BREQBSMRSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-12-7-5-9-13(2)17(21)18-15(14(3)19(22)23-18)11-16-20(4,24-16)10-6-8-12/h8,13,15-16,18H,3,5-7,9-11H2,1-2,4H3/b12-8+/t13-,15+,16-,18?,20-/m1/s1
SMILES:	C/C/1=CCC[C@@]2(C)O[C@@H]2C[C@@H]2C(C(=O)[C@@H](CCC1)C)OC(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1162993
PubChem CID:	46905056
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO24786	Eunicea pinta	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350138]
NPO2321	Eunicea succinea	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8098735]
NPO2321	Eunicea succinea	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392882]
NPO24786	Eunicea pinta	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2321	Eunicea succinea	Species	Plexauridae	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	2.0	ug.mL-1	PMID[571416]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[571416]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	>=	50.0	ug.mL-1	PMID[571416]

☑ 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 NPC469718 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	241
0.1-0.2	1673
0.2-0.3	6173
0.3-0.4	13133
0.4-0.5	11771
0.5-0.6	6254
0.6-0.7	2680
0.7-0.8	651
0.8-0.85	98
0.85-0.9	13
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC329857
0.9545	High Similarity	NPC474947
0.9438	High Similarity	NPC476275
0.9425	High Similarity	NPC20713
0.9167	High Similarity	NPC272814
0.9032	High Similarity	NPC476270
0.8966	High Similarity	NPC231889
0.8764	High Similarity	NPC166919
0.8764	High Similarity	NPC151770
0.875	High Similarity	NPC475703
0.8667	High Similarity	NPC49342
0.8667	High Similarity	NPC475748
0.8667	High Similarity	NPC251385
0.8667	High Similarity	NPC62815
0.8636	High Similarity	NPC50637
0.8506	High Similarity	NPC128429
0.8488	Intermediate Similarity	NPC141810
0.8478	Intermediate Similarity	NPC212486
0.8471	Intermediate Similarity	NPC617
0.8444	Intermediate Similarity	NPC202672
0.8444	Intermediate Similarity	NPC475902
0.8438	Intermediate Similarity	NPC264477
0.8438	Intermediate Similarity	NPC477511
0.8427	Intermediate Similarity	NPC38576
0.8427	Intermediate Similarity	NPC279859
0.8404	Intermediate Similarity	NPC17585
0.8387	Intermediate Similarity	NPC140543
0.8387	Intermediate Similarity	NPC474035
0.8387	Intermediate Similarity	NPC81386
0.8387	Intermediate Similarity	NPC473316
0.8387	Intermediate Similarity	NPC473330
0.8352	Intermediate Similarity	NPC307411
0.8316	Intermediate Similarity	NPC471140
0.8315	Intermediate Similarity	NPC474547
0.8315	Intermediate Similarity	NPC38468
0.8315	Intermediate Similarity	NPC319795
0.8315	Intermediate Similarity	NPC50362
0.8298	Intermediate Similarity	NPC14961
0.8298	Intermediate Similarity	NPC273197
0.8298	Intermediate Similarity	NPC270013
0.8298	Intermediate Similarity	NPC234339
0.828	Intermediate Similarity	NPC165383
0.8261	Intermediate Similarity	NPC51004
0.8261	Intermediate Similarity	NPC312042
0.8247	Intermediate Similarity	NPC15993
0.8247	Intermediate Similarity	NPC201718
0.8247	Intermediate Similarity	NPC164598
0.8247	Intermediate Similarity	NPC474339
0.8222	Intermediate Similarity	NPC284902
0.8211	Intermediate Similarity	NPC31645
0.8211	Intermediate Similarity	NPC299396
0.8211	Intermediate Similarity	NPC172998
0.8211	Intermediate Similarity	NPC301596
0.8211	Intermediate Similarity	NPC476315
0.8202	Intermediate Similarity	NPC470238
0.8202	Intermediate Similarity	NPC138647
0.8191	Intermediate Similarity	NPC471147
0.8191	Intermediate Similarity	NPC476267
0.8182	Intermediate Similarity	NPC477510
0.8182	Intermediate Similarity	NPC471143
0.8182	Intermediate Similarity	NPC474741
0.8182	Intermediate Similarity	NPC173609
0.8172	Intermediate Similarity	NPC184463
0.8172	Intermediate Similarity	NPC30515
0.8172	Intermediate Similarity	NPC208886
0.8172	Intermediate Similarity	NPC12172
0.8163	Intermediate Similarity	NPC324017
0.8163	Intermediate Similarity	NPC320019
0.8144	Intermediate Similarity	NPC469551
0.8144	Intermediate Similarity	NPC477512
0.8132	Intermediate Similarity	NPC471739
0.8132	Intermediate Similarity	NPC5130
0.8125	Intermediate Similarity	NPC328562
0.8125	Intermediate Similarity	NPC323421
0.8105	Intermediate Similarity	NPC475659
0.809	Intermediate Similarity	NPC170377
0.809	Intermediate Similarity	NPC474472
0.809	Intermediate Similarity	NPC318468
0.809	Intermediate Similarity	NPC474703
0.809	Intermediate Similarity	NPC257358
0.8085	Intermediate Similarity	NPC179746
0.8085	Intermediate Similarity	NPC475302
0.8085	Intermediate Similarity	NPC125674
0.8085	Intermediate Similarity	NPC228451
0.8085	Intermediate Similarity	NPC475912
0.8085	Intermediate Similarity	NPC81419
0.8085	Intermediate Similarity	NPC476300
0.8085	Intermediate Similarity	NPC475838
0.8081	Intermediate Similarity	NPC475873
0.8068	Intermediate Similarity	NPC286229
0.8068	Intermediate Similarity	NPC25684
0.8068	Intermediate Similarity	NPC281949
0.8068	Intermediate Similarity	NPC301477
0.8061	Intermediate Similarity	NPC47880
0.8043	Intermediate Similarity	NPC469628
0.8043	Intermediate Similarity	NPC471047
0.8043	Intermediate Similarity	NPC469653
0.8043	Intermediate Similarity	NPC475906
0.8043	Intermediate Similarity	NPC469631
0.8041	Intermediate Similarity	NPC54843
0.8041	Intermediate Similarity	NPC279561
0.8023	Intermediate Similarity	NPC476794
0.8023	Intermediate Similarity	NPC470240
0.8022	Intermediate Similarity	NPC469676
0.8022	Intermediate Similarity	NPC470242
0.8021	Intermediate Similarity	NPC473859
0.802	Intermediate Similarity	NPC477513
0.8	Intermediate Similarity	NPC57405
0.8	Intermediate Similarity	NPC190294
0.8	Intermediate Similarity	NPC303942
0.8	Intermediate Similarity	NPC474247
0.798	Intermediate Similarity	NPC149371
0.798	Intermediate Similarity	NPC474747
0.798	Intermediate Similarity	NPC471148
0.7959	Intermediate Similarity	NPC475949
0.7959	Intermediate Similarity	NPC288876
0.7957	Intermediate Similarity	NPC4986
0.7957	Intermediate Similarity	NPC474951
0.7957	Intermediate Similarity	NPC295312
0.7957	Intermediate Similarity	NPC475971
0.7957	Intermediate Similarity	NPC173926
0.7955	Intermediate Similarity	NPC474510
0.7935	Intermediate Similarity	NPC266957
0.7917	Intermediate Similarity	NPC36954
0.7912	Intermediate Similarity	NPC47958
0.7912	Intermediate Similarity	NPC304509
0.7912	Intermediate Similarity	NPC235792
0.7912	Intermediate Similarity	NPC215364
0.7912	Intermediate Similarity	NPC149725
0.79	Intermediate Similarity	NPC475945
0.79	Intermediate Similarity	NPC475871
0.7895	Intermediate Similarity	NPC135776
0.7889	Intermediate Similarity	NPC250315
0.7889	Intermediate Similarity	NPC170286
0.7879	Intermediate Similarity	NPC474742
0.7872	Intermediate Similarity	NPC144133
0.7872	Intermediate Similarity	NPC474761
0.7872	Intermediate Similarity	NPC476004
0.7872	Intermediate Similarity	NPC179394
0.7857	Intermediate Similarity	NPC208233
0.7857	Intermediate Similarity	NPC473326
0.7849	Intermediate Similarity	NPC224652
0.7849	Intermediate Similarity	NPC281516
0.7843	Intermediate Similarity	NPC474716
0.7841	Intermediate Similarity	NPC276647
0.7841	Intermediate Similarity	NPC471740
0.7841	Intermediate Similarity	NPC622
0.7835	Intermediate Similarity	NPC35498
0.7835	Intermediate Similarity	NPC230800
0.7835	Intermediate Similarity	NPC279621
0.7826	Intermediate Similarity	NPC261253
0.7826	Intermediate Similarity	NPC122502
0.7826	Intermediate Similarity	NPC474045
0.7826	Intermediate Similarity	NPC469626
0.7826	Intermediate Similarity	NPC475491
0.7822	Intermediate Similarity	NPC472756
0.7816	Intermediate Similarity	NPC65603
0.7802	Intermediate Similarity	NPC115786
0.78	Intermediate Similarity	NPC189609
0.78	Intermediate Similarity	NPC291500
0.78	Intermediate Similarity	NPC140591
0.78	Intermediate Similarity	NPC197835
0.78	Intermediate Similarity	NPC303653
0.7791	Intermediate Similarity	NPC138408
0.7791	Intermediate Similarity	NPC155587
0.7791	Intermediate Similarity	NPC226669
0.7791	Intermediate Similarity	NPC193351
0.7789	Intermediate Similarity	NPC221282
0.7789	Intermediate Similarity	NPC133698
0.7778	Intermediate Similarity	NPC471326
0.7778	Intermediate Similarity	NPC221231
0.7766	Intermediate Similarity	NPC474032
0.7766	Intermediate Similarity	NPC78008
0.7757	Intermediate Similarity	NPC270478
0.7753	Intermediate Similarity	NPC223904
0.7753	Intermediate Similarity	NPC474981
0.7742	Intermediate Similarity	NPC160138
0.7742	Intermediate Similarity	NPC186148
0.7742	Intermediate Similarity	NPC118601
0.7742	Intermediate Similarity	NPC270270
0.7732	Intermediate Similarity	NPC163228
0.7732	Intermediate Similarity	NPC475900
0.7732	Intermediate Similarity	NPC471141
0.7732	Intermediate Similarity	NPC474490
0.7723	Intermediate Similarity	NPC472755
0.7714	Intermediate Similarity	NPC475495
0.7701	Intermediate Similarity	NPC235906
0.77	Intermediate Similarity	NPC110443
0.77	Intermediate Similarity	NPC128733
0.77	Intermediate Similarity	NPC472753
0.77	Intermediate Similarity	NPC185141
0.77	Intermediate Similarity	NPC133907
0.77	Intermediate Similarity	NPC46998
0.7692	Intermediate Similarity	NPC39588
0.7692	Intermediate Similarity	NPC471934
0.7692	Intermediate Similarity	NPC38154
0.7692	Intermediate Similarity	NPC475842
0.7692	Intermediate Similarity	NPC11620
0.7692	Intermediate Similarity	NPC53867
0.7684	Intermediate Similarity	NPC471818

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 NPC469718 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	2230
0.2-0.3	3992
0.3-0.4	1837
0.4-0.5	571
0.5-0.6	222
0.6-0.7	70
0.7-0.8	1
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8315	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD1695	Approved
0.72	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD46	Approved
0.7143	Intermediate Similarity	NPD6698	Approved
0.7075	Intermediate Similarity	NPD6008	Approved
0.6931	Remote Similarity	NPD5282	Discontinued
0.6818	Remote Similarity	NPD6371	Approved
0.6804	Remote Similarity	NPD1694	Approved
0.68	Remote Similarity	NPD7838	Discovery
0.6744	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5693	Phase 1
0.6569	Remote Similarity	NPD7983	Approved
0.6509	Remote Similarity	NPD5696	Approved
0.6495	Remote Similarity	NPD6435	Approved
0.6495	Remote Similarity	NPD5209	Approved
0.6471	Remote Similarity	NPD5785	Approved
0.6436	Remote Similarity	NPD6672	Approved
0.6436	Remote Similarity	NPD5737	Approved
0.6404	Remote Similarity	NPD6053	Discontinued
0.64	Remote Similarity	NPD5786	Approved
0.6396	Remote Similarity	NPD5697	Approved
0.6392	Remote Similarity	NPD5369	Approved
0.6355	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5778	Approved
0.6346	Remote Similarity	NPD5779	Approved
0.6339	Remote Similarity	NPD6011	Approved
0.6339	Remote Similarity	NPD6881	Approved
0.6339	Remote Similarity	NPD6899	Approved
0.632	Remote Similarity	NPD7260	Phase 2
0.6316	Remote Similarity	NPD6649	Approved
0.6316	Remote Similarity	NPD6650	Approved
0.6306	Remote Similarity	NPD5739	Approved
0.6306	Remote Similarity	NPD6402	Approved
0.6306	Remote Similarity	NPD6675	Approved
0.6306	Remote Similarity	NPD7128	Approved
0.63	Remote Similarity	NPD5363	Approved
0.6296	Remote Similarity	NPD6648	Approved
0.6289	Remote Similarity	NPD5368	Approved
0.6283	Remote Similarity	NPD6014	Approved
0.6283	Remote Similarity	NPD6372	Approved
0.6283	Remote Similarity	NPD6013	Approved
0.6283	Remote Similarity	NPD6373	Approved
0.6283	Remote Similarity	NPD6012	Approved
0.6263	Remote Similarity	NPD7154	Phase 3
0.625	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5344	Discontinued
0.6238	Remote Similarity	NPD4249	Approved
0.6228	Remote Similarity	NPD7102	Approved
0.6228	Remote Similarity	NPD7290	Approved
0.6228	Remote Similarity	NPD6883	Approved
0.6226	Remote Similarity	NPD5695	Phase 3
0.6214	Remote Similarity	NPD6673	Approved
0.6214	Remote Similarity	NPD6080	Approved
0.6214	Remote Similarity	NPD6904	Approved
0.6207	Remote Similarity	NPD4632	Approved
0.6195	Remote Similarity	NPD7320	Approved
0.6195	Remote Similarity	NPD6686	Approved
0.619	Remote Similarity	NPD6399	Phase 3
0.6186	Remote Similarity	NPD6009	Approved
0.6176	Remote Similarity	NPD4250	Approved
0.6176	Remote Similarity	NPD4251	Approved
0.6174	Remote Similarity	NPD8130	Phase 1
0.6174	Remote Similarity	NPD6617	Approved
0.6174	Remote Similarity	NPD6869	Approved
0.6174	Remote Similarity	NPD6847	Approved
0.6167	Remote Similarity	NPD6319	Approved
0.6162	Remote Similarity	NPD4270	Approved
0.6162	Remote Similarity	NPD4269	Approved
0.6154	Remote Similarity	NPD5692	Phase 3
0.6148	Remote Similarity	NPD7604	Phase 2
0.6146	Remote Similarity	NPD4756	Discovery
0.6142	Remote Similarity	NPD6845	Suspended
0.6139	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6882	Approved
0.6121	Remote Similarity	NPD8297	Approved
0.6116	Remote Similarity	NPD5983	Phase 2
0.6111	Remote Similarity	NPD6083	Phase 2
0.6111	Remote Similarity	NPD6084	Phase 2
0.6105	Remote Similarity	NPD8039	Approved
0.61	Remote Similarity	NPD5362	Discontinued
0.6098	Remote Similarity	NPD7492	Approved
0.6095	Remote Similarity	NPD5694	Approved
0.6095	Remote Similarity	NPD6050	Approved
0.6087	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6684	Approved
0.6078	Remote Similarity	NPD7521	Approved
0.6078	Remote Similarity	NPD5330	Approved
0.6078	Remote Similarity	NPD6409	Approved
0.6078	Remote Similarity	NPD6098	Approved
0.6078	Remote Similarity	NPD7146	Approved
0.6078	Remote Similarity	NPD7334	Approved
0.6077	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6101	Approved
0.6055	Remote Similarity	NPD4225	Approved
0.6055	Remote Similarity	NPD7638	Approved
0.6053	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.605	Remote Similarity	NPD7115	Discovery
0.6048	Remote Similarity	NPD6616	Approved
0.6034	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6054	Approved
0.6019	Remote Similarity	NPD7839	Suspended
0.6019	Remote Similarity	NPD3573	Approved
0.6016	Remote Similarity	NPD7642	Approved
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD7078	Approved
0.5984	Remote Similarity	NPD6015	Approved
0.5984	Remote Similarity	NPD8517	Approved
0.5984	Remote Similarity	NPD8516	Approved
0.5984	Remote Similarity	NPD8515	Approved
0.5984	Remote Similarity	NPD6016	Approved
0.5984	Remote Similarity	NPD8513	Phase 3
0.5981	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7900	Approved
0.5966	Remote Similarity	NPD6274	Approved
0.5965	Remote Similarity	NPD6614	Approved
0.5962	Remote Similarity	NPD6903	Approved
0.5962	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4252	Approved
0.596	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4819	Approved
0.596	Remote Similarity	NPD4820	Approved
0.596	Remote Similarity	NPD4822	Approved
0.596	Remote Similarity	NPD4821	Approved
0.5952	Remote Similarity	NPD7736	Approved
0.5948	Remote Similarity	NPD2067	Discontinued
0.5943	Remote Similarity	NPD6411	Approved
0.5941	Remote Similarity	NPD6110	Phase 1
0.5935	Remote Similarity	NPD6370	Approved
0.5935	Remote Similarity	NPD5988	Approved
0.5934	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD7331	Phase 2
0.5926	Remote Similarity	NPD5210	Approved
0.5926	Remote Similarity	NPD4629	Approved
0.5922	Remote Similarity	NPD6422	Discontinued
0.592	Remote Similarity	NPD6336	Discontinued
0.5918	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6317	Approved
0.5902	Remote Similarity	NPD6059	Approved
0.5893	Remote Similarity	NPD5211	Phase 2
0.5873	Remote Similarity	NPD8293	Discontinued
0.5868	Remote Similarity	NPD6314	Approved
0.5868	Remote Similarity	NPD6313	Approved
0.5868	Remote Similarity	NPD6335	Approved
0.5856	Remote Similarity	NPD5285	Approved
0.5856	Remote Similarity	NPD5286	Approved
0.5856	Remote Similarity	NPD4696	Approved
0.5854	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5207	Approved
0.5842	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6001	Approved
0.5824	Remote Similarity	NPD7341	Phase 2
0.582	Remote Similarity	NPD7100	Approved
0.582	Remote Similarity	NPD7101	Approved
0.5818	Remote Similarity	NPD5959	Approved
0.5818	Remote Similarity	NPD7902	Approved
0.5818	Remote Similarity	NPD4755	Approved
0.5804	Remote Similarity	NPD5223	Approved
0.58	Remote Similarity	NPD4695	Discontinued
0.5789	Remote Similarity	NPD5141	Approved
0.578	Remote Similarity	NPD5654	Approved
0.5763	Remote Similarity	NPD2204	Approved
0.576	Remote Similarity	NPD7830	Approved
0.576	Remote Similarity	NPD8328	Phase 3
0.576	Remote Similarity	NPD7829	Approved
0.5758	Remote Similarity	NPD4271	Approved
0.5758	Remote Similarity	NPD4268	Approved
0.5752	Remote Similarity	NPD5226	Approved
0.5752	Remote Similarity	NPD4633	Approved
0.5752	Remote Similarity	NPD5224	Approved
0.5752	Remote Similarity	NPD5225	Approved
0.5748	Remote Similarity	NPD8074	Phase 3
0.5738	Remote Similarity	NPD7641	Discontinued
0.5727	Remote Similarity	NPD4697	Phase 3
0.5727	Remote Similarity	NPD5221	Approved
0.5727	Remote Similarity	NPD5222	Approved
0.5727	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8444	Approved
0.5714	Remote Similarity	NPD4700	Approved
0.5702	Remote Similarity	NPD5174	Approved
0.5702	Remote Similarity	NPD5175	Approved
0.5702	Remote Similarity	NPD6868	Approved
0.5688	Remote Similarity	NPD7748	Approved
0.568	Remote Similarity	NPD8080	Discontinued
0.5678	Remote Similarity	NPD4634	Approved
0.5676	Remote Similarity	NPD5173	Approved
0.5669	Remote Similarity	NPD7507	Approved
0.566	Remote Similarity	NPD5208	Approved
0.5648	Remote Similarity	NPD5281	Approved
0.5648	Remote Similarity	NPD5284	Approved
0.5631	Remote Similarity	NPD5332	Approved
0.5631	Remote Similarity	NPD5331	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