NPASS Compound

Structure

NPC474758 OpenBabel07101718232D 26 27 0 0 1 0 0 0 0 0999 V2000 -1.6759 2.1669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6759 -1.2106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3716 -2.3180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9809 -2.4461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1527 -1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4715 0.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0178 1.7871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 1.0135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 -0.0572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5621 1.7299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5027 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5621 -0.7736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0178 -0.8308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4715 0.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0361 1.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0361 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4153 -2.3180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9095 1.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5027 -0.6617 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9095 -0.2955 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9809 -1.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9371 -3.1462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5473 2.0804 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 1.9371 -1.4899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 15 2 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 14 18 2 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 21 1 0 0 0 0 19 20 1 0 0 0 0 19 22 1 0 0 0 0 20 14 1 1 0 0 0 20 25 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	393.934
LogP:	5.605
LogD:	4.293
LogS:	-3.852
# Rotatable Bonds:	3
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.534
Synthetic Accessibility Score:	5.089
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.886
MDCK Permeability:	2.6510799216339365e-05
Pgp-inhibitor:	0.651
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.148
30% Bioavailability (F30%):	0.399

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.207
Plasma Protein Binding (PPB):	96.88021087646484%
Volume Distribution (VD):	0.674
Pgp-substrate:	0.9944586157798767%

ADMET: Metabolism

CYP1A2-inhibitor:	0.2
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.258
CYP2C19-substrate:	0.148
CYP2C9-inhibitor:	0.536
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.232
CYP2D6-substrate:	0.605
CYP3A4-inhibitor:	0.139
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	2.739
Half-life (T1/2):	0.407

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.914
Drug-inuced Liver Injury (DILI):	0.156
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.835
Carcinogencity:	0.056
Eye Corrosion:	0.004
Eye Irritation:	0.022
Respiratory Toxicity:	0.553

Download Data

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

Natural Product: NPC474758

Natural Product ID:	NPC474758
*Common Name:**	Brassicolide Acetate
IUPAC Name:	2-[(1S,5E,9E)-5,9-dimethyl-14-oxo-15-oxabicyclo[11.2.1]hexadeca-5,9,13(16)-trien-2-yl]propan-2-yl acetate
Synonyms:	Brassicolide Acetate
Standard InCHIKey:	JRHSHBMAWLBQTD-YANDCLBWSA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-15-8-6-9-16(2)12-13-19(22(4,5)26-17(3)23)20-14-18(11-7-10-15)21(24)25-20/h9-10,14,19-20H,6-8,11-13H2,1-5H3/b15-10+,16-9+/t19?,20-/m0/s1
SMILES:	CC1=CCCC2=CC(C(CCC(=CCC1)C)C(C)(C)OC(=O)C)OC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481651
PubChem CID:	21775544
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene 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
NPO24464	Nephthea brassica	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[10579864]
NPO24464	Nephthea brassica	Species	Nephtheidae	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	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.2	ug ml-1	PMID[512823]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.03	ug ml-1	PMID[512823]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.81	ug ml-1	PMID[512823]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.72	ug ml-1	PMID[512823]

☑ 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 NPC474758 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	190
0.1-0.2	1328
0.2-0.3	6502
0.3-0.4	16600
0.4-0.5	9046
0.5-0.6	5805
0.6-0.7	2665
0.7-0.8	521
0.8-0.85	30
0.85-0.9	4
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9296	High Similarity	NPC329852
0.9155	High Similarity	NPC294434
0.9155	High Similarity	NPC15499
0.9155	High Similarity	NPC259599
0.9155	High Similarity	NPC117746
0.8816	High Similarity	NPC471325
0.88	High Similarity	NPC178277
0.8784	High Similarity	NPC57744
0.8667	High Similarity	NPC128276
0.8571	High Similarity	NPC472266
0.8451	Intermediate Similarity	NPC276290
0.8429	Intermediate Similarity	NPC248125
0.84	Intermediate Similarity	NPC123360
0.8378	Intermediate Similarity	NPC476355
0.8378	Intermediate Similarity	NPC140287
0.8354	Intermediate Similarity	NPC475947
0.8333	Intermediate Similarity	NPC42470
0.8333	Intermediate Similarity	NPC265574
0.8333	Intermediate Similarity	NPC325031
0.831	Intermediate Similarity	NPC194871
0.8289	Intermediate Similarity	NPC97516
0.8286	Intermediate Similarity	NPC470688
0.8228	Intermediate Similarity	NPC35556
0.8219	Intermediate Similarity	NPC469660
0.8194	Intermediate Similarity	NPC470256
0.8108	Intermediate Similarity	NPC84038
0.8108	Intermediate Similarity	NPC257618
0.8108	Intermediate Similarity	NPC163003
0.8101	Intermediate Similarity	NPC141810
0.8095	Intermediate Similarity	NPC473448
0.8082	Intermediate Similarity	NPC88877
0.8082	Intermediate Similarity	NPC476591
0.8077	Intermediate Similarity	NPC270126
0.8077	Intermediate Similarity	NPC471299
0.8056	Intermediate Similarity	NPC203335
0.8052	Intermediate Similarity	NPC10572
0.8052	Intermediate Similarity	NPC141789
0.8052	Intermediate Similarity	NPC68156
0.8052	Intermediate Similarity	NPC476028
0.8052	Intermediate Similarity	NPC171204
0.8049	Intermediate Similarity	NPC469483
0.8026	Intermediate Similarity	NPC244166
0.8	Intermediate Similarity	NPC155849
0.8	Intermediate Similarity	NPC16349
0.8	Intermediate Similarity	NPC222244
0.8	Intermediate Similarity	NPC173609
0.8	Intermediate Similarity	NPC217940
0.8	Intermediate Similarity	NPC474705
0.7975	Intermediate Similarity	NPC281132
0.7973	Intermediate Similarity	NPC67183
0.7973	Intermediate Similarity	NPC64234
0.7973	Intermediate Similarity	NPC37929
0.7949	Intermediate Similarity	NPC93763
0.7949	Intermediate Similarity	NPC108816
0.7945	Intermediate Similarity	NPC218477
0.7927	Intermediate Similarity	NPC215364
0.7922	Intermediate Similarity	NPC27205
0.7901	Intermediate Similarity	NPC170377
0.7901	Intermediate Similarity	NPC53867
0.7901	Intermediate Similarity	NPC12283
0.7901	Intermediate Similarity	NPC474193
0.7895	Intermediate Similarity	NPC474551
0.7887	Intermediate Similarity	NPC34883
0.7875	Intermediate Similarity	NPC301477
0.7875	Intermediate Similarity	NPC25684
0.7875	Intermediate Similarity	NPC281949
0.7867	Intermediate Similarity	NPC129665
0.7857	Intermediate Similarity	NPC151648
0.7857	Intermediate Similarity	NPC471047
0.7857	Intermediate Similarity	NPC469631
0.7857	Intermediate Similarity	NPC475906
0.7857	Intermediate Similarity	NPC469628
0.7857	Intermediate Similarity	NPC469653
0.7848	Intermediate Similarity	NPC469620
0.7848	Intermediate Similarity	NPC469690
0.7848	Intermediate Similarity	NPC617
0.7838	Intermediate Similarity	NPC232812
0.7838	Intermediate Similarity	NPC470693
0.7831	Intermediate Similarity	NPC261253
0.7831	Intermediate Similarity	NPC107787
0.7831	Intermediate Similarity	NPC474045
0.7821	Intermediate Similarity	NPC471225
0.7821	Intermediate Similarity	NPC476794
0.7821	Intermediate Similarity	NPC470240
0.7821	Intermediate Similarity	NPC474760
0.7821	Intermediate Similarity	NPC187568
0.7821	Intermediate Similarity	NPC41780
0.7805	Intermediate Similarity	NPC474865
0.7805	Intermediate Similarity	NPC476804
0.7805	Intermediate Similarity	NPC149869
0.7792	Intermediate Similarity	NPC469414
0.7792	Intermediate Similarity	NPC329826
0.7778	Intermediate Similarity	NPC200513
0.7778	Intermediate Similarity	NPC85772
0.7778	Intermediate Similarity	NPC26624
0.7763	Intermediate Similarity	NPC58956
0.7763	Intermediate Similarity	NPC474543
0.7763	Intermediate Similarity	NPC472018
0.7763	Intermediate Similarity	NPC238425
0.7763	Intermediate Similarity	NPC269206
0.7763	Intermediate Similarity	NPC295633
0.7763	Intermediate Similarity	NPC287878
0.7738	Intermediate Similarity	NPC160138
0.7738	Intermediate Similarity	NPC475703
0.7733	Intermediate Similarity	NPC472017
0.7722	Intermediate Similarity	NPC471220
0.7722	Intermediate Similarity	NPC253749
0.7722	Intermediate Similarity	NPC474005
0.7722	Intermediate Similarity	NPC267231
0.7722	Intermediate Similarity	NPC299235
0.7711	Intermediate Similarity	NPC189311
0.7711	Intermediate Similarity	NPC78089
0.7711	Intermediate Similarity	NPC99395
0.7711	Intermediate Similarity	NPC474547
0.7711	Intermediate Similarity	NPC197903
0.7692	Intermediate Similarity	NPC235906
0.7692	Intermediate Similarity	NPC469880
0.7683	Intermediate Similarity	NPC169575
0.7683	Intermediate Similarity	NPC40746
0.7683	Intermediate Similarity	NPC474703
0.7683	Intermediate Similarity	NPC170286
0.7683	Intermediate Similarity	NPC475989
0.7683	Intermediate Similarity	NPC193198
0.7674	Intermediate Similarity	NPC471818
0.7674	Intermediate Similarity	NPC312042
0.7671	Intermediate Similarity	NPC191233
0.7662	Intermediate Similarity	NPC470686
0.7654	Intermediate Similarity	NPC475481
0.7654	Intermediate Similarity	NPC79277
0.7647	Intermediate Similarity	NPC226863
0.7647	Intermediate Similarity	NPC476805
0.7647	Intermediate Similarity	NPC475902
0.7632	Intermediate Similarity	NPC67076
0.7632	Intermediate Similarity	NPC477084
0.7632	Intermediate Similarity	NPC319163
0.7632	Intermediate Similarity	NPC186531
0.7619	Intermediate Similarity	NPC475461
0.7619	Intermediate Similarity	NPC305475
0.7619	Intermediate Similarity	NPC279859
0.7619	Intermediate Similarity	NPC261721
0.7619	Intermediate Similarity	NPC50637
0.7619	Intermediate Similarity	NPC38576
0.7619	Intermediate Similarity	NPC284902
0.7614	Intermediate Similarity	NPC476267
0.7614	Intermediate Similarity	NPC476596
0.76	Intermediate Similarity	NPC269841
0.76	Intermediate Similarity	NPC151481
0.76	Intermediate Similarity	NPC101622
0.76	Intermediate Similarity	NPC107130
0.7595	Intermediate Similarity	NPC320630
0.7595	Intermediate Similarity	NPC65603
0.7595	Intermediate Similarity	NPC7563
0.7595	Intermediate Similarity	NPC116177
0.759	Intermediate Similarity	NPC475100
0.759	Intermediate Similarity	NPC31086
0.759	Intermediate Similarity	NPC82297
0.759	Intermediate Similarity	NPC115786
0.759	Intermediate Similarity	NPC30486
0.7564	Intermediate Similarity	NPC193351
0.7564	Intermediate Similarity	NPC138408
0.7564	Intermediate Similarity	NPC155587
0.7564	Intermediate Similarity	NPC226669
0.7561	Intermediate Similarity	NPC10080
0.7561	Intermediate Similarity	NPC471218
0.7561	Intermediate Similarity	NPC123908
0.7561	Intermediate Similarity	NPC474291
0.7558	Intermediate Similarity	NPC166919
0.7558	Intermediate Similarity	NPC174342
0.7534	Intermediate Similarity	NPC220766
0.7531	Intermediate Similarity	NPC474510
0.7529	Intermediate Similarity	NPC476600
0.7529	Intermediate Similarity	NPC478144
0.7529	Intermediate Similarity	NPC478145
0.75	Intermediate Similarity	NPC476598
0.75	Intermediate Similarity	NPC69462
0.75	Intermediate Similarity	NPC261380
0.75	Intermediate Similarity	NPC474341
0.75	Intermediate Similarity	NPC474816
0.75	Intermediate Similarity	NPC68110
0.75	Intermediate Similarity	NPC255307
0.75	Intermediate Similarity	NPC209135
0.75	Intermediate Similarity	NPC139692
0.75	Intermediate Similarity	NPC4299
0.75	Intermediate Similarity	NPC184737
0.75	Intermediate Similarity	NPC470755
0.75	Intermediate Similarity	NPC476597
0.75	Intermediate Similarity	NPC192006
0.75	Intermediate Similarity	NPC65661
0.75	Intermediate Similarity	NPC474658
0.7471	Intermediate Similarity	NPC475748
0.7471	Intermediate Similarity	NPC144133
0.7471	Intermediate Similarity	NPC179394
0.7471	Intermediate Similarity	NPC475855
0.747	Intermediate Similarity	NPC318468
0.747	Intermediate Similarity	NPC475622
0.747	Intermediate Similarity	NPC59097
0.747	Intermediate Similarity	NPC108045
0.747	Intermediate Similarity	NPC44261
0.747	Intermediate Similarity	NPC131669
0.747	Intermediate Similarity	NPC473390

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 NPC474758 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1905
0.2-0.3	4177
0.3-0.4	2043
0.4-0.5	574
0.5-0.6	217
0.6-0.7	62
0.7-0.8	3
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
0.8028	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5209	Approved
0.7778	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4820	Approved
0.7108	Intermediate Similarity	NPD4819	Approved
0.7108	Intermediate Similarity	NPD4822	Approved
0.7108	Intermediate Similarity	NPD4821	Approved
0.7108	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1694	Approved
0.7079	Intermediate Similarity	NPD6698	Approved
0.7079	Intermediate Similarity	NPD5785	Approved
0.7079	Intermediate Similarity	NPD46	Approved
0.7059	Intermediate Similarity	NPD7154	Phase 3
0.6977	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1695	Approved
0.6914	Remote Similarity	NPD8039	Approved
0.6912	Remote Similarity	NPD6927	Phase 3
0.6897	Remote Similarity	NPD5363	Approved
0.6889	Remote Similarity	NPD7838	Discovery
0.6867	Remote Similarity	NPD4268	Approved
0.6867	Remote Similarity	NPD4271	Approved
0.6867	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5362	Discontinued
0.6774	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6435	Approved
0.6737	Remote Similarity	NPD7638	Approved
0.6737	Remote Similarity	NPD4225	Approved
0.67	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6629	Remote Similarity	NPD7521	Approved
0.6629	Remote Similarity	NPD6409	Approved
0.6629	Remote Similarity	NPD7334	Approved
0.6629	Remote Similarity	NPD6684	Approved
0.6629	Remote Similarity	NPD7146	Approved
0.6629	Remote Similarity	NPD5330	Approved
0.6628	Remote Similarity	NPD5369	Approved
0.6628	Remote Similarity	NPD4790	Discontinued
0.6593	Remote Similarity	NPD6051	Approved
0.6569	Remote Similarity	NPD6371	Approved
0.6562	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4251	Approved
0.6556	Remote Similarity	NPD4250	Approved
0.6552	Remote Similarity	NPD4269	Approved
0.6552	Remote Similarity	NPD4270	Approved
0.6512	Remote Similarity	NPD4252	Approved
0.6512	Remote Similarity	NPD5368	Approved
0.6495	Remote Similarity	NPD6648	Approved
0.6494	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6903	Approved
0.6484	Remote Similarity	NPD5737	Approved
0.6484	Remote Similarity	NPD6672	Approved
0.6452	Remote Similarity	NPD7637	Suspended
0.6452	Remote Similarity	NPD5693	Phase 1
0.6444	Remote Similarity	NPD4249	Approved
0.6444	Remote Similarity	NPD5786	Approved
0.6429	Remote Similarity	NPD5344	Discontinued
0.6383	Remote Similarity	NPD5779	Approved
0.6383	Remote Similarity	NPD5778	Approved
0.6316	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6084	Phase 2
0.6289	Remote Similarity	NPD6083	Phase 2
0.6286	Remote Similarity	NPD6053	Discontinued
0.6277	Remote Similarity	NPD7983	Approved
0.625	Remote Similarity	NPD5695	Phase 3
0.6237	Remote Similarity	NPD6904	Approved
0.6237	Remote Similarity	NPD6673	Approved
0.6237	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6080	Approved
0.6237	Remote Similarity	NPD6101	Approved
0.6232	Remote Similarity	NPD5343	Approved
0.6204	Remote Similarity	NPD7115	Discovery
0.6146	Remote Similarity	NPD7748	Approved
0.6146	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7900	Approved
0.6139	Remote Similarity	NPD6647	Phase 2
0.6125	Remote Similarity	NPD7331	Phase 2
0.6117	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6110	Phase 1
0.6105	Remote Similarity	NPD6050	Approved
0.6105	Remote Similarity	NPD6411	Approved
0.6082	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5696	Approved
0.6058	Remote Similarity	NPD6881	Approved
0.6058	Remote Similarity	NPD6899	Approved
0.6042	Remote Similarity	NPD6399	Phase 3
0.604	Remote Similarity	NPD7632	Discontinued
0.6026	Remote Similarity	NPD368	Approved
0.6022	Remote Similarity	NPD3573	Approved
0.602	Remote Similarity	NPD7839	Suspended
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5692	Phase 3
0.5979	Remote Similarity	NPD5282	Discontinued
0.5977	Remote Similarity	NPD4756	Discovery
0.5962	Remote Similarity	NPD5697	Approved
0.596	Remote Similarity	NPD7902	Approved
0.5957	Remote Similarity	NPD5208	Approved
0.5943	Remote Similarity	NPD7102	Approved
0.5943	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7290	Approved
0.5943	Remote Similarity	NPD6883	Approved
0.5938	Remote Similarity	NPD7515	Phase 2
0.5938	Remote Similarity	NPD5694	Approved
0.5914	Remote Similarity	NPD6098	Approved
0.5914	Remote Similarity	NPD6422	Discontinued
0.5905	Remote Similarity	NPD7320	Approved
0.5895	Remote Similarity	NPD5370	Suspended
0.5888	Remote Similarity	NPD8130	Phase 1
0.5888	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6847	Approved
0.5888	Remote Similarity	NPD6617	Approved
0.5888	Remote Similarity	NPD6649	Approved
0.5888	Remote Similarity	NPD6869	Approved
0.5888	Remote Similarity	NPD6650	Approved
0.5854	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6372	Approved
0.5849	Remote Similarity	NPD6014	Approved
0.5849	Remote Similarity	NPD6013	Approved
0.5849	Remote Similarity	NPD6012	Approved
0.5849	Remote Similarity	NPD6373	Approved
0.5833	Remote Similarity	NPD8297	Approved
0.5833	Remote Similarity	NPD6882	Approved
0.5833	Remote Similarity	NPD5207	Approved
0.581	Remote Similarity	NPD5701	Approved
0.5802	Remote Similarity	NPD7341	Phase 2
0.5797	Remote Similarity	NPD6096	Approved
0.5797	Remote Similarity	NPD6097	Approved
0.5794	Remote Similarity	NPD2067	Discontinued
0.5776	Remote Similarity	NPD7507	Approved
0.5773	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD6695	Phase 3
0.5755	Remote Similarity	NPD6011	Approved
0.5753	Remote Similarity	NPD29	Approved
0.5753	Remote Similarity	NPD28	Approved
0.5747	Remote Similarity	NPD1452	Discontinued
0.5741	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD2204	Approved
0.5732	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD7328	Approved
0.5714	Remote Similarity	NPD6008	Approved
0.5714	Remote Similarity	NPD4211	Phase 1
0.5714	Remote Similarity	NPD3174	Discontinued
0.5714	Remote Similarity	NPD7327	Approved
0.5714	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD3665	Phase 1
0.5699	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD3666	Approved
0.5699	Remote Similarity	NPD3133	Approved
0.5679	Remote Similarity	NPD3197	Phase 1
0.5664	Remote Similarity	NPD7516	Approved
0.5657	Remote Similarity	NPD6001	Approved
0.5652	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD4691	Approved
0.5641	Remote Similarity	NPD6109	Phase 1
0.5638	Remote Similarity	NPD1696	Phase 3
0.563	Remote Similarity	NPD7319	Approved
0.5625	Remote Similarity	NPD4193	Approved
0.5625	Remote Similarity	NPD4192	Approved
0.5625	Remote Similarity	NPD4194	Approved
0.5625	Remote Similarity	NPD4191	Approved
0.5614	Remote Similarity	NPD8294	Approved
0.5614	Remote Similarity	NPD8377	Approved
0.5612	Remote Similarity	NPD5284	Approved
0.5612	Remote Similarity	NPD6079	Approved
0.5612	Remote Similarity	NPD5281	Approved
0.5604	Remote Similarity	NPD7332	Phase 2
0.5604	Remote Similarity	NPD4695	Discontinued
0.5604	Remote Similarity	NPD7514	Phase 3
0.5604	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.56	Remote Similarity	NPD5210	Approved
0.56	Remote Similarity	NPD5654	Approved
0.56	Remote Similarity	NPD4629	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